We (hello, weāre Jason and Caroline Zook š©š»āš¦°šØš»āš¦² by the way) know how tough it is to start a business, run a business, or simply create a new product or service.
The number of to-dos and tasks get piled higher than all the stacks of pancakes š„ at IHOP on a busy Saturday morning. But it’s not actually the project to-dos themselves that bring us stress; itās all the mindset hurdles we have to navigate in accomplishing those tasks that bring our projects to a screeching halt.
We have personal experience with this entire cast of lovely charactersā¦
Fear not, though! Over the years we’ve acquired some tools to shift these mindsets and we want to share them with you. Weāll go over a bunch of these “mindset poisons” in this article AND give you the “mindset antidotes” to deal with them!
We want you to know you are NOT ALONE, and dealing with these mindset hurdles as a business owner is completely normal š.
We all have voices and thoughts in our heads that are not helpful. Some voices are louder than others and can keep us from reaching our goals.
š§ “My work isnāt as good as theirs, so why try?”
š§ “Who cares what I have to say?”
š§ “Iām an imposter and totally unqualified to do this!”
These are just a few examples of mindset poisons. They are thoughts and ideas that run rampant in our minds, kind of like a kid getting let loose at a Chuck E. Cheese šš§š for the first time. (Gosh, remember those simpler times??)
Our goal with the rest of this article is to identify a handful of these mindset poisons and offer you mindset antidotes that have been critically helpful for us and our Wandering Aimfully members over the years.
Weāve created a ā”ļø 5-step process ā”ļø to help cure ANY mindset poison you might encounter! This simple process will be the guiding force moving forward (kind of like a giant mouse was the guiding force at Chuck E. Cheese*).
Extremely random and silly fact: From 1977 to 1992 the Chuck E. Cheese mascot was an anthropomorphic rat, then it was changed to a mouse in 1993. In 2012, the mascot was rebranded into a smaller, “hipper” mouse-version in an attempt to increase sales. (Thank you Wikipedia!)
The first step to changing anything is becoming AWARE of what you wish to change.
What is the poison when we break it down into its most basic fear? What moment from our childhood or a previous time in our lives is this fear grabbing onto?
What thoughts and actions can you intentionally shift in order to offset the effect of the “poison”? What is an opposite action (antidote) you can take?
Imagine your mindset shifting from negative to positive. How would a specific situation be different using a different outlook?
Identify 3 tangible habits, practices, or processes to ACTIVATE that antidote and see it play out in your work and life.
Don’t worry, we’ll go over specific examples throughout this article, but now that you have a clear process for working through your own toxic mindsets, you will be able to identify your own antidotes any time you encounter an unhelpful mindset in the future.
Okay, let’s get into a few specifics, shall we!
When Perfectionism holds you back:
š Projects or tasks drag on because you always see how they can be 1% better.
š You abandon an idea or project before sharing it because you donāt want people to see what you consider an imperfect product.
š You wonāt try a new endeavor because you already know you wonāt be able to execute to your perfect standards.
š You donāt allow yourself to be vulnerable or authentic because the real parts of you feel imperfect.
The question to ask yourself: “What fear does my perfectionism really stem from?”
Potential answer: “Iām afraid of feeling not good enough.”
Ways this root fear can impact you…
š “Iām afraid people will judge me if I put out something less than perfect.”
š “I learned as a kid that I wasnāt worthy of love unless I was perfect so feeling not good enough feels like Iām worthless.” (This one goes out to all our fellow over-achievers!)
Let’s go with: “Iām afraid of feeling not good enough.”
š¤ What are some thoughts you can repeat to yourself that can assuage that fear?
š” “I am already āgood enoughā as a person because my worth is inherent.”
š” “I have the power to decide what āgood enoughā means in my work, which is separate from my worth.”
š” “My skillset may not be perfect, but Iāll never improve if I donāt continue making and sharing things.”
Basicallyā¦learn to be your own best friend and lean into some self-love (you deserve it)!
š Perfectionism (poison) says: “Iām afraid of feeling not good enough.”
šŖ Completion (antidote) says: “I’m the one who gets to define ahead of time what is good enough in my work and that will help me keep creating.”
Constraints help you pre-define “good enough” and completion helps you focus on finishing (not perfecting) so you can make more awesome stuff.
The goal is no longer to make something perfect; itās to COMPLETE something in the time allotted to the standards you already set.
There is a snowball effectāthe more you complete, the more you will see that things donāt have to be perfect for them to get you results.
You practice overcoming the fear of feeling not good enough by reframing good enough as something YOU determine, not anyone else.
Previous you: Posting 1 or 2 “perfect” things on social media and continuing to feel stuck.
Antidote you: Posting consistently according to your constraints, knowing youāre planting seeds of audience growth every time you publish!
š Try a daily challenge: Here’s an idea. For the next 2 weeks, publishing something daily thatās imperfect but still helps move the needle forward for your business. Thereās nothing like a daily challenge to desensitize you to imperfection.
ā³ Constrain your time: You only get ONE hour to do X task. Once the time is up, you are done and you move on. No extra time. No perfecting for hours.
š Write a “good enough” list: Before you start a project or share your work, try making a checklist for yourself for what Good Enough means in your eyes.
Constraints help you fight perfectionism by pre-defining “good enough” and completion helps you make more awesome stuff with less pressure.
When Self-Doubt holds you back:
š© You say no to opportunities because you doubt your abilities or donāt think youāre qualified.
š© You feel paralyzed before you get started on a new idea because you donāt believe youāre capable of figuring it out.
š© Youāre afraid to raise your prices or charge more for your product because you doubt people will pay it.
š© You feel a general sense of Imposter Syndrome which affects the confidence you bring to situations.
The question to ask yourself: “What fear does my self-doubt really stem from?”
Potential answer: “Iām afraid of being exposed as a āfraudā.”
š¤ What are some thoughts that can assuage that fear?
š” “I know that Iām conscientious and I will give my best to every opportunity.”
š” “I have taken on opportunities before when I felt fearful and it turned out okay.”
š” “Iām not ādefraudingā anyone! If Iām clear about my strengths and honest about my skills, I can set the expectations of those I fear letting down.”
š© Self-Doubt (poison) says: “Iām afraid of being exposed as a fraud.”
š¤ Self-Trust (antidote) says: “Giving myself the opportunity to grow does not make me a fraud. I trust myself that I can handle the discomfort of growth and I will bring my best to any opportunity.”
You think you need confidence first in order to trust in yourself, but you actually need to trust yourself before you can build confidence.
Self-doubt counts you out before you even begin; self-trust deals you in so you can continue to grow.
Self-trust is a muscle. The more you can trust yourself and practice sitting with the discomfort of feeling “out of your depth” the more you will grow and the less uncertain youāll feel.
Previous you: You say NO to speaking or podcast opportunities because you doubt in your ability to deliver.
Antidote you: You say YES to opportunities, even if they scare you, and you grow your brand awareness and improve your speaking skillset.
š Create a “trustworthy” list: Sit down and make a running list of all the things youāre good at and the things you know how to doāall the reasons big and small that make you trustworthy. Go back to this list when you doubt yourself.
šŖ Intentionally practice a skill: Building self-trust takes EXPERIENCE. But you donāt have to wait for an opportunity to grow. If you want to get better at something, set time aside to practice which will improve your confidence.
šÆ Set a “rep goal”: 50 speaking engagements. 20 podcast interviews. 50 art pieces. Focus on a clear goal to get the experience and this will help you establish building self-trust as the goal, not the outcome.
Overcome self-doubt with self-trust. You think you need confidence first in order to trust in yourself, but you actually need to trust yourself before you can build confidence.
When Need For Validation holds you back:
š¬ You let the thoughts and opinions of your audience steer your content in a direction that doesnāt feel authentic.
š¬ A negative comment or email sends you into a self-doubt spiral.
š¬ You try to be everything to everyone so you donāt turn anyone off your brand, but for this you end up being vanilla.
The question to ask yourself: “What fear does my need for validation really stem from?”
Potential answer: “I’m afraid of not being liked.”
š¤ What are some thoughts that can assuage that fear?
š” “Not being liked might feel crappy in the short-term but stifling my own wants or needs in the long-term will have much more severe consequences.”
š” “I canāt make everyone happy anyway, so I might as well be true to myself.”
š” “Relying on other people for my source of happiness or validation puts way too much power in the hands of other people.”
š¬ Need For Validation (poison) says: “Iām afraid of not being liked.”
š Intrinsic Motivation (antidote) says: “Being liked is not my primary objectiveābeing MYSELF is. Iām not chasing acceptance, Iām fueled by my own deeper purpose.”
Intrinsic motivation is about finding a WHY and a purpose that has nothing to do with the opinions of other people.
It requires that you prioritize your opinion of yourself above the opinion of others.
You have to be willing to be misunderstood, not liked, or ignored in order to try something new.
You can be motivated by the desire to develop a skill; the desire to be creative; the desire to impact other people positivelyā¦anything but “I am motivated by the desire to be liked.”
You have to learn to prefer the free feeling of being true to yourself above the fleeting feeling of being patted on the back or liked
Previous you: You water down your content to please everyone and feed the algorithm, but start to feel uninspired.
Antidote you: You allow yourself to experiment, you feel free, you stumble upon a new area you want to explore.
š Write down your why: When you embark on a project or endeavor, be sure to take time to write down your deeper why. This will help you stay connected to your motivation even if people donāt “get it.”
š Donāt wait for the response: If youāre putting your work out there or hitting publish on something, donāt just wait with bated breath to see the reaction. Once you release it, let that be enough.
š Celebrate yourself: Become your biggest fan. When you push the envelope or try something new, celebrate it. Congratulate yourself. Learn to value your opinion of yourself in the highest regard.
Avoid the constant need for validation by focusing solely on intrinsic motivation. Intrinsic motivation is about finding a WHY that has nothing to do with the opinions of other people.
When Comparison holds you back:
š You use the talent or success of others to put yourself down or feel negative about where you are.
š You follow others so closely that you lose your unique voice and start to copy their blueprint instead.
š You compare your beginning to someone elseās middle so you think something isnāt worth doing because you donāt have the skills of someone whoās further along.
š You see how someone else does things and it makes you question your instincts.
The question to ask yourself: “What fear does my comparison really stem from?”
Potential answer: “Iām afraid of being judged as inadequate.”
š¤ What are some thoughts that can assuage that fear?
š” “Inadequate according to whom?! I canāt let the opinions of other people stop me from making progress toward my goals.”
š” “Comparison is relative, so why do I only use comparison as a means to discourage myself, rather than comparing myself to where I was a year ago?”
š” “I canāt compare my journey to anyone elseās because they arenāt me. They donāt have the same strengths, values, skills, etc. that I do so I have to make decisions that are right for no one else but me.”
š Comparison (poison) says: “Iām afraid of being judged as inadequate.”
š¬ Owning Your Story (antidote) says: “My story is mine alone. I canāt look to the path of others to set my standard of adequacy; only I can do that for myself.”
Owning your story will help you focus on the strengths within your own experience/self instead of chasing the story of others.
Comparison is about looking outward at others for cues on how youāre doing; owning your story is about looking inward instead.
Once you realize that everyone’s path is 100% unique to them, you realize that comparison is futile.
Previous you: I want to start a travel vlog but compare my video editing skills to the popular channels and feel discouraged and paralyzed.
Antidote you: I know I have a unique creative voice to bring to the table so I start anyway and one year from now my travel vlogs feel polished and unique to me.
š Limit your consumption: One easy way to stop comparing yourself is to limit your exposure to what other people are up to. If you find yourself comparing, unfollow. Spend more time creating than consuming.
š§ Make a core values list: Remember, those you are comparing yourself to are not operating with your same core values. Write down what YOU care about, what your guiding list of values is, and this will help you own your unique path/story.
šŗ Write down your journey: Write down a timeline of all the pivotal moments that led you to where you are now. This will help you focus in on YOUR journey, no one elseās, and remind you how far youāve come.
Steer clear of comparison traps by leaning heavily into your story. Owning your story will help you focus on the strengths within your own experience/self instead of chasing the story of others.
When Procrastination holds you back:
ā± You put off getting started on projects because you donāt know where to begin.
ā± You donāt get back to clients or other business connections in a timely manner.
The question to ask yourself: “What fear does my procrastination really stem from?”
Potential answer: “Iām afraid of feeling overwhelmed and like I’m not capable.”
š¤ What are some thoughts that can assuage that fear?
š” “The most overwhelmed Iāll be during a project is likely at the beginning, so the sooner I get started, the sooner I can get through that feeling.”
š” “Overwhelm is something I feel if I focus on the WHOLE project instead of just the first step.”
š” “Not knowing how to get started or what to do is a natural part of figuring anything out.”
ā± Procrastination (poison) says: “Iām afraid of feeling overwhelmed.”
āļø Permission to Start Ugly (antidote) says: “I embrace feeling overwhelmed or inept at the beginning of every project because I know itās a part of the process.”
Giving yourself “permission to start ugly” will help lower the stakes for getting started.
By focusing on “starting” rather than the whole project, you can reduce that overwhelm just a tad and find the discipline just to tackle step 1 instead of steps 1-100.
Keep your expectations super low to get started and with that first action, youāll notice you build momentum, requiring less effort to continue moving the ball forward.
Youāll make yourself feel like whatever crappy version you start with was done on purpose!
Previous you: Waiting until the week of a deadline to start a project, getting stressed out and working long hours all week.
Antidote you: Starting the moment you got the project, and working in increments to slowly complete/improve the project.
š¦¢ Make “ugly” part of your process: Not everything starts out as a swan! Whatever your process is for your work, make step 1 something that is VERY low barrier and easy to accomplish. Ex) coaching slides
ā³ Set a “Getting Started” timer: Constraints for the win again! If you have trouble feeling overwhelmed when you start, try setting a timer for just 15 minutes to “start ugly.” You can do anything for 15 minutes!
š Do the 5-minute task first: Title the Google Doc, even if you don’t start it yet. Import your footage. Write bullets for the blog post. Choose one maddeningly simple place to start.
If youāre constantly procrastinating, giving yourself “permission to start ugly” will help lower the stakes for getting started.
When People-Pleasing holds you back:
š„ You say yes to too many opportunities because you donāt want to say no or let people down.
š„ You let clients take advantage of you and project scopes creep because you have trouble putting your foot down.
š„ You donāt speak up for yourself when a situation feels out of integrity or inauthentic because you donāt want to seem “difficult.”
The question to ask yourself: “What fear does my people-pleasing really stem from?”
Potential answer: “Iām afraid of letting other people down.”
š¤ What are some thoughts that can assuage that fear?
š” “My responsibility is to myself first. I have to put on my own oxygen mask first.”
š” If people are not okay with me standing up for my own needs, they are not people I want to let into my circle anyway.”
š” As long as Iām clear and up front about what my feelings/needs are, most people will respect that.”
š„ People-Pleasing (poison): “Iām afraid of letting people down.”
ā Boundaries (antidote): “When I take on too much or donāt speak up for myself, I let myself down. I have a right to protect my energy and be honest about what I can and canāt take on.”
Boundaries are how you articulateāto yourself and othersāwhat does and doesnāt feel authentic to you.
When you are clear about your boundaries, you limit your resentment toward other people or the feeling that theyāre taking advantage of you.
Every time you enforce a boundary, youāre choosing to “love yourself, even if you risk disappointing others” (credit: BrenĆ© Brown).
Previous you: You say yes to every request a client makes because you donāt want to disappoint them but you end up spending twice as long on a project for half the money.
Antidote you: You establish clear boundaries and scope with your clients upfront, and because you’re sticking to timelines you can take on more clients while being happier.
š Know your limits: Hard to enforce boundaries if you donāt know what they are. Decide where your limits are. How much are you willing to work? How many opportunities are you willing to take on?
š Write down your “no scripts”: Saying “no” sometimes feels awkward because weāre so trained to say yes. If you need to practice, write out thoughtful responses to some requests that have crossed your boundaries before.
š Create a “not okay” list: Boundaries arenāt just about what youāre willing to take on, they’re about what behavior youāre willing to accept. Make a list of things that are not okay with you so that if they come up, you can speak up.
If youāre constantly procrastinating, giving yourself “permission to start ugly” will help lower the stakes for getting started.
In this section, we wanted to give some quicker antidotes to additional poisons that can affect our mental fortitude as entrepreneurs.
Over-Thinking (poison): “Iām afraid of making the wrong decision.”
Embracing Experimentation (antidote): “Itās impossible to know the ārightā or āwrongā decision. I canāt think my way to an answer; I have to ACT my way to an answer and learn by doing.”
Need For Control (poison): “Iām afraid of putting my fate in someone elseās hands.”
Collaboration (antidote): “I recognize that there are also positive things gained from combining forces with someone else.”
Disappointment (poison): “Iām afraid Iām not cut out for this.”
An Attitude of Service (antidote): “One setback doesnāt define me. Instead of focusing on one lackluster launch or project, I choose to focus on helping/serving others and how good that makes me feel.”
Over-Committing(poison): “Iām afraid of losing out on an opportunity.”
Prioritization (antidote): “My next opportunity is not my last opportunity. I can only be effective if I choose where to place my focus carefully.”
Giving Up Easily(poison): “Iām afraid of trying and failing so I give up before I can feel disappointed.”
Patience, Persistence, and Practice (antidote): “I know anything worth pursuing will have setbacks and I need to offer myself time to work through those setbacks to get to where I want to be.ā
Unworthiness (poison): “Iām afraid Iām not worthy of good things.”
Self-Love (antidote): “Every single human is worthy of good things, including me. I will practice loving myself out loud until I believe that in my bones.”
Much like learning how to sell, market, grow an audience, or even creating a great product or service, mending your mindset is a business skill.
Without the tools (antidotes) to deal with mindset hurdles (poisons) we all face, none of the practical business skills are enough. You know, just like going to Chuck E. Cheese isnāt fun if you only eat pizza and never play whack-a-mole!
Our hope is weāve given you a process to work through whatever mindset poisons might be affecting you or that you might run into in the future. Just remember, your fears and your mental roadblocks are normal and we all go through them!
Now, grab your antidote and kick those poisons to the curb.
A few years ago I loved the idea of creating small software products. In fact, I remember when I started thinking about leaving the 9-5 world in 2005 and dreamed of being a āsoftware startup founder.ā The stories of successful venture-funded startups and crazy monthly revenue seemed otherworldly to me.
Fast forward to 2013 and I started working on my first web application (I am going to interchangeably call them web applications, software products, web apps, whateverā¦ itās all the same to me!) Then in 2015, I had a second web app. In 2016 a third. In 2017 a fourth and a fifth.
Uh oh, you can probably see where this might be headed?
Truthfully, I donāt have any regrets about starting too many software products. I was able to partner with great, talented co-founders, and I enjoyed working on each project.
But hereās the real-talk for youā¦
Starting anything from scratch, no matter how much experience you have in another area (or in that same field) is always going to be its own unique uphill climb.
The idea was to mesh Typeform and note-taking together and to help online course owners give their students a more effective way to consume their teachings.
My co-founder Paul Jarvis and I had a combined audience of over 100,000 people between our email lists and social media followings. We also had a popular podcast (3,000 downloads per episode) where we publicly built the app and found our technical co-founder (hi, Zack!) Paul and I have had solid success selling online courses and other products over the years.
Yet, the best we could do was get ofCourseBooks to around $2,000 monthly recurring revenue (MRR). And we pushed it pretty hard for a few months.
While we were happy to have a side project that didnāt take a ton of continuous effort on our parts, we had certainly hoped it would generate more revenue. We didnāt even have wildly ambitious financial goals, we simply hoped weād get to $10,000 MRR.
This is a similar story for me with almost every software product Iāve built. They are able to generate some monthly revenue but itās never enough for one of them to earn the majority of my focus. And thereās another problemā¦
I understand the blueprint of how to make a software product successful. The issue is that I know it’s not the type of work I want to be doing all the time:
There are probably 20 more bullet points I could list out and thatās precisely why I donāt think Iāll ever run a software company as my sole gig.
It gets even more challenging to shut down a project or keep going when your identity is tied to it in some way.
If you’re reading this article then your work is probably tied to your identity in some way. Your name is associated with your product or you ARE the product (hello designers, artists, developers, any freelancers).
It’s especially tough to make a decision about moving forward or shutting down an idea when you feel a strong connection to it.
There’s a certain amount of fear that comes along with shutting down a project that isn’t serving us. Kristen Yates, a member of our Wandering Aimfully community talked about it like this:
When I tap into this fear of letting go of a project there’s often something around an identity I’ve attached myself with around it in addition to the time/resources/energy sunk in. It makes me curious to explore what that fear is about? What it means to let go of something that we may have attached with beyond it simply being an income source or even a passion project? What about when it becomes a part of who we are?
Kristen is totally right and brings up some really valid questions. This has been a struggle for me with many of my projects over the years.
If you quit something that’s fundamentally tied to who you position yourself as to the outside world you can feel trapped. If you say you’re a designer, but stop being a designer, will everything think you’re a fraud? Will they question what you “pivot” to next because it’s unfamiliar and different?
There’s no easy answer when it comes to dealing with the fear and the identity crisis that can come with pouring ourselves so deeply into our work.
If people don’t respect change and don’t see it as necessary, they’re not people I want to surround myself with. And sure, we can’t control what people say or think about us, but we shouldn’t be focusing on that anyway. You have to focus on what you can control and if that’s making a big change in your life or business, then that’s a perfectly acceptable decision.
No matter what type of product or idea youāre building, it can feel like youāre always on the edge of success or failure.
Does this edge feel like success or failure to you right now?
We, as business owners, have this thing when it comes to our creations. They always feel like they might be on the cusp of taking off and therefore itās so much harder to let go of them.
And then there’s the other side. Things could crumble at any moment. Yet, we’ll hang on for too long due to sunk cost bias. You know, spending countless hours, days, weeks, months, and even years on an idea and not wanting to throw all of that away for fear of “failing.”
Or, you know, just create space and NOT IMMEDIATELY FILL IT. (Thatās as much a note to you, dear reader, as it is to future Jason).
For me, and maybe for you, itās important to sit down and really weigh the options with whatever youāre currently working on that isnāt bringing you the value youād hoped.
During the past year, Iāve decided that Iām not going to keep dragging projects along if they arenāt bringing me value. The revenue isnāt the most important indicator, in fact, itās probably a dead-tie with enjoyment.
And let’s be honest, we all probably have a project or two that sucks our time and attention away, while not returning much value back.
Thatās the question I keep coming back to. I love the thrill of creating a new software product. I love working with talented people and bringing an idea to life. I enjoy a little bit, the challenge of getting people to make the initial purchase. But things start to fall short for me when I feel Iām constantly chasing after growth, even a small amount of it.
Iām in my āzone of geniusā when Iām doing weird things. When Iām creating projects that make people tilt their heads and sharing ideas that feel completely unique to me. The problem is, not all of those weird projects can pay the bills on a consistent basis.
Iām sorry to be the bearer of bad news, but it feels like there is no ONE answer (to rule them all). It feels more like we all need to understand working for ourselves is an ongoing and ever-changing process.
You might be reading this and have found your ONE thing and youāre kicking major ass with it. Awesome! If working on your idea brings you value and you don’t feel trapped by it, you should absolutely keep going. You should acknowledge the path to success will be a winding one and you may never reach an actual finish line. Enjoy the bumps along the way, they’re only going to provide invaluable lessons and moments where you can improve and get better.
However, for a lot of us, the answer may not be to keep going, it may be time to shut a project down.
A special thank you to Reed and J.P. who are the owners of two web apps I co-founded.
Slowly but surely Iāve realized that I canāt manage and run five different software companies.
Itās actually not even the marketing and time investment thatās the issue, itās the mental toll it takes to keep track of all of them (shocker, I know).
I’ve started giving myself permission to sell-off or shut down projects that aren’t bringing me value.
I had two successful āexits,ā as they say in this business. Those exit amounts wonāt impress you, and truthfully, thatās not really the point of this article. I do want to acknowledge that Iām grateful to have a community around me that believes in the products Iāve built and are willing to invest their money and continue working on those ideas.
There’s an underlying layer of stress when we continue to carry projects along and not make a decision to move on from them.
My hope is that this article helps you move on from an idea you may feel stuck with. Some app or thing that you feel you can’t stop working on because it was so close to finally being worth all the time and energy.
So, what will it be for you? Are you shutting down or pushing forward?
Did I ever tell you about the time I ran a $1,000,000 business? I think most of you are familiar with my time as the IWearYourShirt guy, and if youāre not, you can read the whole story in my first book. In a nutshell, I came up with a crazy idea in 2008, ran my butt off for five years to grow it and scale it, made seven figures in revenue, accumulated six figures in debt, hit my breaking point, and then shut the whole thing down and walked away.
My first failure in business. Womp womp.
But now that you know the end of the IWearYourShirt story, letās back up half a sentence to that breaking point I mentioned. What was it, how did I realized Iād hit it, and what triggers should you be watching out for in your own business?
When IWearYourShirt was growing, so were the dollar signs in my eyes. THIS WAS THE NEXT BIG THING! (I told myself.) I made nearly $90,000 the first year, and it was loads of fun. I was getting press and media attention around the world. I had big-name companies reaching out to me. I had āfans,ā which was really odd.
(A hilariously awkward walk down memory lane: The first “photoshoot” I did for IWearYourShirt promo photos.)
During the first year of IWearYourShirt, I received more external validation than I had had in my entire life. Up until that point, I was a nobody. Iād done nothing worth talking about. This was my moment to shine. The external validation showed up in many ways:
I read stories about startup founders getting venture capital funding, and I wanted that. I heard about companies hiring lots of employees and that sounded like something I should be doing. I heard all the multi-million dollar valuations and assumed thatās what I should be striving for. Everything I was thinking was growth-focused, and if youāre a smart cookie, you might know where that train was heading.
In 2011, I saw my first glimpse that there might be an issue with the IWearYourShirt business model, and the business itself. The way IWearYourShirt made money was by putting an incremental price on each day of the calendar year. This meant that the early months of the year didnāt bring in a ton of revenue. Add on top of that I was trying to grow the amount of shirt wearers (employees) in IWearYourShirt (who all required a standard monthly salary).
While IWearYourShirt had a decent cushion of money in the bank from the first two years, I still lived off that money. When January 2011 rolled around and I needed to pay $25,000 in employee salaries and business expenses, the shirt-wearing calendar had only generated $2,500 in sales. I knew we were in trouble. The cash-flow of IWearYourShirt just didnāt make sense, neither did me trying to take on ALL the roles in the company: CEO, CMO, CFO, COO, any Cās and any Oās, I was doing it. Oh, and I was also still the head shirt wearer, donning a shirt, creating content on social media sites, filming a YouTube video, hosting a 1-hour live video show, managing customers, and answering upwards of 300 emails per day.
You can hear that disaster train screaming down the tracks, canāt you?
I was able to juggle money, rob Peter to pay Paul, and borrow money from family, but all of that only lasted until early 2012 (when I tried to continue growing, without fixing the actual flaws in my business model).
By the summer of 2012, for the first time in my life, I had accrued business debt. And it wasnāt just a few thousand dollars. I was in the hole over $75,000.
I can distinctly remember those summer months in 2012. Asking myself: How the hell did this happen!? Everything was going so great??
IWearYourShirt was being talked about everywhere. I was living the so-called entrepreneurial dream. Yet, here I was, in debt, completely stressed out, insanely over-worked, and not seeing the writing on the wall. Something had to change. Something had to give. The disaster train was continuing to bear down the tracks toward me.
In 2013 I attended a conference in Fargo, North Dakota, where I was a featured speaker for a small, but awesome, group of fellow āmisfitsā (entrepreneurs, doers, thinkers, artists, musicians, etc). The event was appropriately called Misfit Conference.
When I took the stage, everyone expected to hear my story of t-shirt wearing success. Many folks in attendance had heard of āthe t-shirt guyā and were ready to listen to all my business victories and triumphs. But something in me just couldnāt do it anymore. Something in me couldnāt pretend everything was okay. I was in debt. I hadnāt had a good night of sleep in months. I gained nearly 50 pounds. I had just let go of a few employees to be able to afford to pay our bills.
I donāt remember exactly what I said. I remember the beginning as I held nothing back and shared how I was chasing all of these growth metrics and other peopleās ideas of success. And then I remember the end of my talk, seeing tears in some of the audience memberās eyes as they stood and clapped. It was a complete blur for me, but apparently sharing all my mistakes and failures really resonated with my fellow misfits.
As my wife, Caroline, and I flew home from that conference, we sat on the plane and had a tough conversation about how we were living our lives and how IWearYourShirt was impacting us (my wife worked for my company for the last two years). After listening to other speakers at the Misfit Conference share stories of minimalism, avoiding the trappings of society, and carving out your own path and definition of success, all the light bulbs seemed to go off for us. For five years IWearYourShirt had been an incredible ride, but the time had come to step off that ride and get on a new, less bumpy, rickety, unpredictable, and soul-sucking ride.
How did I go about quitting my business and how can you decide if you need to quit running a business thatās no longer serving you?
Something I did, and that we should all do more often, is to check in with ourselves. To answer questions like these:
Every decision Iād been making with my IWearYourShirt business was based on external ideas of success: More customers. More employees. More money. More attention. More, more, more.
But when I really sat down to think about it, those werenāt the things that made me happy. What made me happy was having a comfortable amount of money, but not gobs of it. I enjoyed the personal validation of sharing my crazy ideas and antics, but I didnāt need tons of people to see those things or give me praise for them.
In the Spring of 2013, shortly after attending the Misfit Conference, my total amount of business debt hit $100,000. This debt was owed to family, spread across multiple credit cards (7 of them), and was bills outstanding to vendors weād used. $100,000 was my line in the sand and I didnāt know it until it happened (please let you number be WAY lower!).
By this point I knew my business had to be shut down. It was limping along, barely supporting us financially, and sucking every last ounce of money, creativity, and energy I had.
On May 6, 2013, I closed the virtual doors of IWearYourShirt. I let my remaining employees go, including myself and my wife.
I hope, for your sake, your line in the sand doesnāt have to be $100,000 in debt, being 50 pounds overweight, or feeling like your life is completely out of your control. I hope youāve made the realization that your business model is broken or that youāre running a business that you donāt truly believe in any longer.
When your business starts trending in the wrong direction it can feel like all the walls are crumbling down around you. Without a clear path laid out in front of you, youāll want to stick to the only (broken) path you do have. But the longer you stay on a broken path, the longer it takes to find your next path.
For me, in 2013, I didnāt have a next step. I didnāt have another business idea. But I had built something. For five years Iād run a company that brought in a substantial amount of revenue and provided jobs for a handful of creative people (as well as opened a ton of doors for me). Not everything Iād done during that time was wasted effort, and I could use the lessons Iād learn to move forward.
Similar to how IWearYourShirt got off the ground, I started emailing a few entrepreneurial friends for advice. It was only 10ish people in my trust circle, but one person wrote back with a really helpful question. He said something to the effect of:
āJason, what do people ask you about the most? Would could you teach from your years of experience?ā
That was actually an easy question for me to answer: People emailed me constantly asking how they could go about getting a paid sponsorship for their blog, event, etc, since Iād been able to secure so many t-shirt sponsors (and others) during my IWearYourShirt run. The answer to that question led to creating my first online course, How To Get Sponsorships For Anything. The initial launch of that course brought in $32,000 and has gone on to generate over $150,000 in total revenue (plus help me create my first software product: Teachery). Sure, there was a ton of hard work to do all of that, but it was an entire new path I never saw coming.
One of the most important things you can do if your business is struggling, or if you feel lost, is to reach out to someone with experience and talk to them.
After my talk at Misfit Conference, a woman named Pam Slim walked up and gave me a huge hug. Pam and I had chatted on Twitter a few times, and even seen each other at other events, but this was different. She looked me in the eyes and said, āJason, please call me and letās chat.ā (Iām sure there was much more said, but thatās what stuck in my mind.)
Now, itās worth mentioning, because I want to let you know itās okay if you donāt ask for help right away. It took 8 months for me to gather the courage to call Pam. Iām not joking. I thought about her offer nearly every day, but I was scared. I was embarrassed at what she would think. And I had convinced myself that I could figure everything out on my own (stupid male pride!) Getting on an hour-long call with Pam was one of the best things I ever did after shutting down my business. The thing that stood at the most during out chat, and has continued to resonate with me for years, is that Pam explained that IWearYourShirt being a failure didnāt mean I was a failure as a person. Businesses fail every day and I should take the lessons (good and bad) that I learned from IWearYourShirt and move on to whatever was next.
I implore you to find the Pam Slim in your life. They may be an email connection away. They may be someone whoās written a book youāve read. They may be some sort of business coach youāve heard about. Heck, they could simply be a family member whoās had business experience.
Another tip here: Read the book The Obstacle is the Way. I wrote an article entirely about this book as I think itās the most important book Iāve ever read. I highly highly HIGHLY recommend that book!
Itās up to you to decide if you should walk away from your business, but walking away from my business was one of the best decisions Iāve ever made.
Looking back, itās easy to see ALL the writing on ALL the walls. I was obsessed with external success metrics and thought I could feel better by constantly striving for more.
I never took the time to establish my core values. To actually write down what things would make me happy. Instead I just picked things I read about in articles, saw on TV, or heard friends gushing about.
I wouldnāt go back and change anything during my IWearYourShirt experience from 2008-2013. The ups, the downs, riding the disaster train, all of it shaped me into the person I am today.
I continue to learn lessons every day from those five years. I know theyāll continue to provide me immense value, and I hope my story might inspire you to take a hard look at where you get your validation and if thereās a tough decision you need to make about a business thatās no longer serving you.
**
Thanks to Caleb Campbell for asking me to write this article originally for Why I Stopped.
In business and in life, we talk a lot about the topic of āfailure.ā
The fear of failing keeps so many of us from taking risks (or trying anything at all) and itās responsible for keeping people stuck in jobs they donāt like or businesses that arenāt working.
In response to this, a new conversation around failure has been forming in the entrepreneurial ecosystem, one that says: āIf youāre not failing, youāre not trying something differentā¦ā or āFailure teaches us more than success ever willā¦ā or āFail forward.ā
These aphorisms can be motivating, and I love that they aim to re-frame the negative feelings we have toward failure, but more often than not they represent only TALK.
How many business owners or creatives do you see actually showingĀ you their failures? Not just brushing them under the rug but REALLY shining a light on them and celebrating them?
I know Iām guilty of this. I can write newsletters about experimentationĀ or my processes for making tough decisions in my business, but I admit thereās a part of me that always tries to spin these moves in such a way that avoids calling them what they really are:Ā failures.
Honest question: did your heart sink just a bit when you read that wordā¦ āFAILURE.ā It has quite a specter to it, doesnāt it? It feels almost taboo when youāre highlighting it so directly like that, not side skirting or spinning it to make yourself feel more comfortable with it.
Which is exactly why I want to join in this reframing conversation around failure but in a way that isnāt just talk. I want to gloriously and openly share with you all the experiments I undertake in my business that DONāT work out, and I want to do so without shame.
Maybe then it will encourage us all to be a tiny bit braver in pushing our own creativity and exploring new territory in our businesses.
So, today, letās talk about my most beautiful failure to date: Color Your Soul.
If youāre a member, youāve already been alerted to this, but for those of you who donāt know yet,Ā unfortunately Iāve come to the decision that Januaryās issue of Color Your Soul will be its last.
I canāt say ending the subscription hasn’t crossed my mind the past few months as the product never truly gained the numbers I needed it to in order to be financially viable. However, I loved creating it SO much and loved the community within it so much that I truly think I was blind to the toll it was really taking on me. Until last week.
There are so many reasons I arrived recently at this difficult (but right-for-me) decision, and I want to share those with you guys so that you might be able to learn from my own experience.
I don’t think I ever fully expressed just how much time and effort goes into the creation of the monthly Color Your Soul issue AND the creation of each new monthly workshop or course.
Between selecting the theme, gathering inspiration and resources, creating the art pieces and preparing them for the issue, formatting everything into the magazine and the website, each issue easily took me over 40 hours to put together.
I was happy to invest that time so that each element of the issue would be personal and heartfelt, but when I compare the time investment to the financial return, as a business owner I just canāt justify it.
Admittedly, the bar that I set for each issue from the beginning was a bit ambitious, and while I’m proud of the quality and heart in each issue, I’m sure I could have been much more diligent about projecting out the time I set aside to complete each issue every month. I shared my thoughts on the importance of time management in last weekās email, and this is definitely a case where the time efficiencies of the product itself really hurt the productās viability.
The original vision for Color Your Soul,Ā aside from being a soulful answer to all the strictly business related resources out there,Ā was actually intended to be a way to consolidate my various courses and projects under one roof.
Ironically, this project has actually done quite the opposite for me. In an effort to promote and boost subscriptions, Iāve done my best to deliver new and interesting instructional content each month, basically doubling my amount of offerings and products in the process. Even if Iām not actively working on or promoting each of these courses/workshops, they take up mental space for me. I have to admit that keeping up that level of mental rigor and stamina has finally caught up with me and Iām ready to once again commit to curtailing my offerings so that I can focus on the few that bring me the greatest joy AND the most significant financial impact.
Iāve always said that thereās a rhythm to running a creative business, one that is like breathing. There is a time for expansion and time for contraction. Expansion is always more comfortable for me, but I look forward to learning how to get comfortable with contraction too.
You have heard me talk about this on workshops and in recent newsletters. The challenge of being a person who wants to make 100% of their income from creative pursuits is that you have to constantly balance the desire to follow your ideas with the practicality of what brings your business money. That’s the puzzle.
After writing the very practical steps in last weekās newsletter and being reinvigorated by the concepts in the Make Money Making workshop, Iāve realized thatĀ I need to take my own medicine. I need to let go of whatās not working (CYS only brings my business about $600/month right now) and I need to restructure things so that I can use my gifts in a way that is sustainable for me and beneficial for you. Otherwise, nobody wins.
Step 4 of last weekās process was this:Ā Start by acting on your Big Brick Wall and your Big Cracked Door.Ā As much as I didnāt want to admit it, Color Your Soul is my Big Brick Wall. I never found a process that allowed me to maintain the vision of the product AND nurture the community AND promote it to new audiences AND have time left over to sustain my other business channels. As I said before, there are two ways to act on a Brick Wall, and thatās either to try and improve whatās not working or to simply let it go. In this case, letting it go is the right (but hard) choice.
Ultimately it comes down to this VERY important and very simple fact. Without realizing it, pouring my time and attention into this project without a healthy, stable return has left me feeling stretched thin and without time and attention for the other things that keep me centered in life.
Things like painting, and getting outside, and connecting 1-on-1 with Made Vibrant community members like you. (You should see my inbox right nowā¦ itās not a pretty sight!)
If I’m honest with myself, these past few monthsĀ I’ve not been living my best and brightest life. It was hard for me to see before, but I can see that now.
As much as you love and believe in an idea,Ā as much as you WANT to sell what is true over what is easy, you also have to accept the reality of what youāre sacrificing to bring that idea to life, and for me, itās just too much.
Though every business and every person is different, there are a few practical lessons I learned from this experiment and Iād like to share those with you.
First, answering to a monthly recurring offering felt inflexible and confining at times, like it was looming over my head and it was a deadline I could never get out in front of. Thatās not the way I want my business to feel, and that’s a lesson I’ll take forward with me when developing new offerings. The allure of recurring revenue was in its ability to provide somewhat predictable (read: stable) income. In theory thatās great, but in practice it feels incredibly restraining. In the future, Iāll go back to embracing ideas with a more flexible structure so I can uphold that value of flexibility.
Selling (and explaining) something that hasnāt been sold before is not easy. If the product itself didnāt take so much time to produce, I would have invested more time in communicating what Color Your Soul was and the value it provides. The lack of time efficiencies never allowed me to do that well, which can account partially for the slow trickle in of subscriptions.
Start small! If you have an idea for a product, fight the urge to apply all the bells and whistles you envision from the outset. Had I started with a version of the product that was more stripped down, I could have been more intentional and efficient with the time it took to produce, and I could have grown it slowly and steadily as subscriptions increased.
Youāve heard me talk about this in theoretical terms before but right now you are seeing it play out. We have ideas and they donāt always work out the way we envision them.Ā That is OKAY āĀ Experiment anyway.Ā ExperienceĀ anyway. And check back in with yourself often so you can learn firsthand what lights you up and what drains you.
Color Your Soul was a beautiful dream of mine that I got to see turn into a reality. Maybe there are things I could have done differently to make it successful and sustainable, but I wouldnāt go back. I have learned a lot these past few months about what brings me joy and what doesnāt, what people are willing to pay for and what theyāre not, what my strengths are and what my weaknesses are. That insight is invaluable to me.
It hurt to close the chapter on Color Your Soul as I know it. It hurt to send emails and refunds and to feel like I was disappointing people. But with everything in me, I will fight the instinct to feel shame or self-doubt around making this decision.
Failures can be beautiful and glorious and valuable. We could use a few more failures, in fact, because it highlights two truths I believe dearly:Ā We wonāt ever know unless we try AND living a vibrant life demands the courage to let go of things that no longer align with our values.
To me, the principal metric of success is that I keep growing and keep stretching myself ā and I keep sharing these pursuits with you all honestly because I want to inspire you to do the same.
Iāve always told you guys that I want to bend my business to my life, not the other way around.
I want to keep molding my offerings as I grow and evolve, and I want to keep experimenting until I find the right mix for the life that feels most vibrant to me.
That thing I tried? Yeah, it didnāt work. Now.. onto the next.
Update: We had a ton of fun building Emojibombs in 2016, but after a few weeks of trying to sell it we didn’t gain much traction and shut it down. I guess you’d call this a “failure” in the business sense, but it was a crapload of fun! Below is the live blog I wrote about this experiment…
I was a Skype call with my buddy Paul when the conversation shifted from whatever topic we were supposed to be focused on over to emojis. (You know, as most Skype conversations naturally transition.)
While joking around, we landed on a silly idea: What if we created fictional origin stories for emojis and asked the Internet to pay to receive one of these stories every day for a year?
We both laughed at the idea and moved on from it. But then the idea pestered us. A few days later I woke up thinking about how fun it would be to read an emoji origin story amidst all the other emails in my inbox. I hopped in the Slack channel Paul and I have (called āRat Peopleā after this article). I told Paul I couldnāt stop thinking about these emoji stories and that we should make it happen. He said he was also thinking about them.
The longer we chatted in Slack to more decisions we made:
Quick aside here: We, as a collective group of makers/creators/entrepreneurs, get very caught up in business. Meaning, we base decisions on outcomes that increase the bottom line and that have concrete ROI. But what about fun? What about doing things just to scratch an itch and to stretch our creativity? Fun was the biggest reason we decided Emojibombs had to be created. Read more about fun and business here. Okay, letās get back to the journey…
We decided June 1 (a Wednesday) would be a good day to build and launch Emojibombs. At the time we put it on our calendars, it was a relatively quiet week. Unbeknownst to me, it ended being one of the busiest weeks Iāll have in all of 2016 (no joke). Nonetheless, we picked a date and committed to it.
*: Paul and I both wake up fairly early. When I woke up at 6am on June 1, Iād already received a message from Paul saying he wished weād set the kick-off call for way earlier. We spent the hours of 6am – 9am twiddling our thumbs and being super antsy to get started. Weāll start earlier the next time we do this. Hah.
**: āEverythingā meant almost everything. With experience, we knew that registering a domain name and getting all the DNS/SSL stuff done ahead of time would help us avoid any dreaded domain propagation issues. Paul did this stuff a few weeks in advance.
***: Neither of us had done a 1-day project before. Weād created plenty of things in the past, but building anything in one day presents a ton of challenges. Iād say we were both a little nervous, but we were also confident that we could get it done based on the scope of the project.
After our emails went out to our lists, we had 335 people registered for the live event. We pitched it as a āmysteriousā and āsillyā event.
On the morning of June 1 our Slack was buzzing with ideas for Emojibombs. Especially in the 3+ hours when we were awake waiting for our own Crowdcast to start. It was hard for us not to start doing things, but even harder when people started messaging us in anticipation…
9am PDT FINALLY rolled around, and we were ready to kick things off… or so we thought. Paul and I have used Crowdcast for almost all our projects in the past year. Weāve done at least 10 Crowdcasts together, and Iāve done another 10 on my own (yes, I can do things without Paul!). But on this day, the launch day for Emojibombs, Crowdcast did not want to cooperate.
At first, I couldnāt see Paulās video. Then I could see him, but I couldnāt hear him. Then he could see me, but he couldnāt hear. It was a terrible game of āwhoās on first,ā but some of the time you couldnāt hear/see the other person. Luckily one of the founders from Crowdcast was in the chat and quickly jumped in to help us out. Iām not sure if he power-cycled the Crowdcast modem or if he pulled out the cartridge and blew on it Nintendo style, but after a few minutes of panic, things finally started working correctly and we were on our way. Of course I grabbed a screenshot amidst all the technical troubles:
Another quick aside: I share the technical hiccup here, not to criticize Crowdcast. Iām actually a very happy paying customer of CrowdcastĀ (that’s my affiliate link) and think they have a fantastic live video/webinar platform. I share this because things will always go wrong. Something will break. Something will not work properly. Some cartridge will need to be pulled out and blown on (that sounded dirty, but stop it, itās a Nintendo reference!). Plan for the technical glitches and allow yourself to take a deep breath in the moment and figure out how to overcome the obstacle staring you in the face.
Anyhoodle, we Crowdcasted. Over 100 people were watching us live as we finally told the world what this āmysteriousā and āsillyā emoji-related project would be. I remember a few things happened right as we explained what Emojibombs would become:
Itās an interesting thing to announce a project to a group of people and then say youāre going to go build it in 1 day. While we appreciated the advice and thoughts of the people on the live call, we also knew weād never get Emojibombs created and launched if we tried to make everyone happy. We had an initial plan (an idea for an MVP, if you will) and were going to stick to that plan.
It was also interesting to watch people leave a live event, essentially saying āI donāt like this idea.ā But, as Paul and I have both learned over the years, seeing those people leave is a good thing. They werenāt interested in Emojibombs and weād rather not spend time trying to convince them otherwise. There were also plenty of other people who were watching and excited about it. I had to avoid worrying about people not liking the idea to focus on the larger number of people who were ready to support us.
Paul and I have worked on a bunch of projects together now. Weāre both acutely aware of our strengths. Paul handles most of the technical and design aspects. I handle the administrative and organizational aspects. If this was our first project together, it would probably have been a complete disaster. But, because weāve worked together so many times before, we knew exactly what the other person would be doing and we trusted each other. Plus, (and this is one of the most important parts of creating a project in 1 day) we have a dedicated Slack channel where we over-communicate with each other. I canāt imagine trying to do this project, or any other project we work on together, without Slack.
Mailchimp had been setup. Stripe had been activated. People were sitting on the website refreshing incessantly.
Me, refreshing https://t.co/hM9G02UXL3, @jasondoesstuff Twitter feed, and @pjrvs feed… #emojibombs pic.twitter.com/JSyS1kE7jJ
— Zach Holloway (@zgholloway) June 1, 2016
We even started to do some marketing. Which, for us, just meant sharing sarcastic updates on social media and other places we already have attention (like other Slack channels).
I remember taking a moment to realize my brain was zooming around a mile-a-minute, and I thought I should take a look at my heart rate on my Fitbit to see if my heart rate matched my mind rate. It did:
Note: Paul would have shared his Fitbit heart rate too, but his wife Lisa had taken his phone with her to go run some errands. He said his heart rate was in the 60s, but I didnāt believe him (and since he couldnāt send me a photo of proof, weāll never know…).
Paul had just finished creating an initial logo and we hopped on Skype to check in with one another and record a short video. Here is that video:
Almost immediately after we finished filming that video we hit our first bump in the road. And by bump, I mean flipped over semi-truck that was carrying 20,000 tons of glue and covered the entire build-a-project-in-1-day highway we were driving down.
You know Mailchimp, right? That email service provider Paul and I both love? Paul has an entire course about how to use Mailchimp! Well, our beloved Mailchimp flagged our brand new account for compliance issues…
Now, why is this such a big deal? Well, if I havenāt cleared explained it, Emojibombs is completely driven by email. Itās a daily emoji origin story sent to someoneās inbox. Mailchimp is the company that would be handling that sending for us. If Mailchimp flagged our account for something and we couldnāt get the compliance issue resolved quickly, it would be almost impossible to launch this project in 1 day.
Paul reached out to Mailchimp through their support form and explained what we were doing and that we didnāt understand why we were being flagged for compliance. We did have a few thoughts as to why it might have happened:
Before I share whether we got out of Mailchimp Jail or not, Iāll pause to take a moment to share what it feels like when you have a vision for your idea and something out of your control yanks the rug out from under your ideating feet.
It freakinā sucks. But, any time you work with another provider or service (Mailchimp, Stripe, etc), you are always at their mercy. This is just a known fact that you have to consider and deal with. While we were upset, we also knew this was a possibility and had to come up with other possible solutions if things didnāt work out in our favor (read: escape Mailchimp Jail with only a dull spork, our wits, and a map made from potato skins).
A funny thing happened when we posted that Mailchimp had put us in temporary jail. Someone from the ConvertKit team sent me a tweet:
if only there was another way! š
— ConvertKit (@ConvertKit) June 1, 2016
If you arenāt familiar with them, ConvertKit is actually the email marketing provider I switched to earlier this year (from Mailchimp). Iām a very happy ConvertKit customer and the only reason we didnāt use them is because Paul is a Mailchimp Wizard (like, Level 12 wizard). While their tweet was funny, it was also a good backup plan if Mailchimp didnāt release us from their compliance clutches.
And then we got an email…
PHEW! Talk about a sigh of relief.
We took a moment to enjoy our victorious escape and immediately got back to work. Truthfully though, we hadnāt just been twiddling our thumbs while we waited anxiously to hear back from Mailchimp. Paul finished the Emojibombs logo and put together a mockup for the homepage. He also finished up the Emojibombs email template:
Paul got Stripe hooked up and we made our first sale! Kind of… I completed a test sale with a live form and my actual credit card. Hey, Iām excited to get these Emojibombs too!
During that time I decided to tackle our user submitted emoji stories. Paul and I had discussed using TypeForm, but then we realized, why not use our own product ofCourseBooks? It could totally work to collect peopleās emoji stories, and itās nice to be able to give another one of our products some exposure while we have peopleās attention.
Once the ofCourseBooks emoji workbook was completed (which took a matter of minutes), I wrote a post asking for emoji stories. (If your story was chosen, you received credit and a link in the body of the Emojibomb, so it was actually not a bad marketing ideaā¦)
At this point in the day, it was about 1pm PDT. Originally we planned to have an email out to our Crowdcast attendees with an update at 11am (whoops!). We also planned to have launched Emojibombs for sale by this time. Two strikes, but weāre not out!
We decided to hop on video and record another quick chat. At the 3-minute mark we talk about missing our initial time goals. But, the entire video is worth a watch if youāre interested in hearing about all the stuff we were working on in that moment.
And another aside: When it comes to any project, itās important to set milestones and time constraints. You donāt have to go crazy, but weāve found that if you donāt put limitations on things, they can tend to drag on and on. On the flip side, when you set milestones and donāt hit them, you have to understand that the majority of milestones are completely arbitrary and made up. You donāt want to get down on yourself just because you missed a self-imposed deadline. You just re-configure the deadline, maybe try to understand why you missed it (so you can learn going forward), and you push on.
At around 2pm, we became professional product-jugglers (which is way less dangerous than chainsaw-jugglers). This was the point in the project when a ton of things were being tossed around and worked on at one time:
After we returned from our short break (probably 15 minutes), Paul sent me a message and told me heād āmade it rain emojis!ā
It was at this moment I did a little happy dance. The idea for Emojibombs didnāt exist in the world a few weeks prior. The actual website was nothing just a few hours before. And yet here we were and Paul had just designed and coded up a super fun homepage, something to really reflect the silliness and side-projectness of Emojibombs.
Creating success page redirects on purchases or freebie signups: This gives the user a nice experience after they purchased or signed for a free Emojibomb (instead of just a green check mark in the Stripe modal or short 1-line success message). Plus, we always add āsocial intentā to our thank you pages. The people who buy your stuff are the most willing to share, you have to make it easy for them!
Adding in the first few emoji origin stories to Mailchimp automations: We knew we only needed one story for the buyers list and one story for the freebie list. Some people may have thought we intended on writing all 365 emoji stories in 24 hours. I donāt think 20 stories would have be possible, let alone those stories plus building the product itself. Getting these first two done was a moral victory.
Flipping the buy page live (which Paul had to think on, but quickly figured out): There was a funny moment in Slack when Paul said āHrm… how do I make this live?ā I started to type a response, nothing that would have actually been helpful (because Iām not a Level 12 wizard like Paul). And then before I could send my message, he wrote back āI got it!ā He had created a private page to build the actual homepage, then he had to set it as the front page in WordPress (which would move the blog off the current homepage). Emojibombs was live!
Hitting SEND on our first sales email to all the folks who subscribed today: I wrote our āsalesā email to our entire list (since no one had purchased at this point). 373 people would get our initial sales email saying that you could buy Emojibombs for $11.
Cleaning up the mess we made on our desktops (so many screenshots!): Hahah. Yeah. Building something in 1 day is hard, but sharing all the steps in the process is an undertaking in itself. At one point I counted 72 screenshots on my desktop. I like to keep the amount of screenshots on my desktop under 10 at all times so there was some serious desktop anxiety going on.
We actually tied up these loose ends on video, so we could capture the moment we pushed Emojibombs live and (hopefully) got our first sale (or two). Hereās our final video:
And you may have heard us mention it in the video above, but we wanted to give some extra love to Zach Holloway who was our first Emojibombs buyer (after me, of course). You rock Zach!
After a solid 8 hours of work, we had a living, breathing, purchasable product that didnāt exist before. I know I can speak for Paul when I say that we were happy, but that our brains also felt a bit like mush. Focusing on anything as intensely as we did for 8 hours will leave you a little brain-fried and ready for a break.
Total traffic to Emojibombs:
Here are our running expenses:
And our total sales numbers to date:
Doing a 1-day project is stressful. But truthfully, itās 100% self-imposed stress, so we had to look at it differently. While we had a few hiccups, things pretty much went to plan. Yes, our brains were a pile of gruel (delicious vegan gruel) at the end of the day, but we had a ton of fun building Emojibombs and sharing the process.
Building Emojibombs showed us how great a 1-day project can be for stretching our creativity, capturing the attention of our audiences, and giving us the opportunity to promote our other projects.
All day on June 1 we were able to captivate the attention of 1,000 of our true fans/subscribers/friends/rat people. Thatās extremely powerful. Sure, weāve only made a measly $3, but this project was not about money. We do plenty of other things to make money. This project was about having fun and including our audiences in the process. Thereās no telling what the long-term positive affect might be for our future projects based on what we did with Emojibombs. And thatās very intriguing.
I want to touch on the fact that a 1-day project is a great promotion tool. Not only for the project youāre creating, thatās obvious, but also for all your other projects. Doing this project reminded me of the quote:
And itās 100% true. Emojibombs was the tide that gave us a platform to promote ourselves, but also our other project (boat) ofCourseBooks. Sure, itās not promoting to a highly targeted audience for that product, but a percentage of marketing is always un-targeted and like casting a wide net. All the boating metaphors!
Emojibombs is not going to end world hunger. Itās not going to solve a huge problem that creative professionals and freelancers have. But it is a slice of fun sent to peopleās inboxes every day. Itās a message of weirdness and hilarity amongst all the to-dos, tasks, and customer service issues that tend to plague our email inboxes. Weāre happy to have created something that will bring people joy for $11 for the next 365 days of their life. Sounds like a pretty good deal to us.
Iām not sure what our next 1-day project will be, but weāll definitely be doing this again. I hope youāve enjoyed seeing behind all the curtains with Emojibombs. Now excuse me while I go write some silly emoji origin stories.
Does your workday spiral out of control from the moment you wake up? Is there a relationship in your life that feels toxic?Ā Are you feeling overwhelmed?
You might not want to hear this, but itās time to quit.
Thereās a lot of advice out there saying āDonāt give up!ā and āPush through the tough times!ā But those statements come with lots of caveats. What if you hate what you are doing? What if the tough times are putting your health at risk? What if giving up frees up time for new opportunities?
The added time and freedom youāll feel from quitting are well worth the struggle of making the call to let go and move on.
Whether itās a short-term quit or a long-term quit, itās time to take control. Itās time for you to take the necessary steps to get yourself out of situations that arenāt bringing you value.
When it comes to freeing up your time you donāt necessarily have to quit something completely.
Short-term quitting (or taking a pause) is a great way to create mental space and give yourself a breakāone that can help you figure out if you want to quit completely or continue on.
In 2014Ā I got really frustrated with social media. I wasnāt seeing the interaction that Iād seen in years prior and felt myself getting angry when reading tweets and posts from people about topics I didnāt want to read.
I realized it was time for a break (short-term quit).
For 30 days I quit social media. I deleted the apps from my phone (Twitter, Facebook, YouTube, etc) and I removed all associated bookmarks and browsing history. I wasnāt going to read or post anything for a month and see how I felt at the end.
Would I want to get back on social media? Would I want to quit forever? Only 30 days would tell.
During the social media hiatus, I felt a wave of emotions. I was sad that I wasnāt able to interact with people I genuinely enjoyed talking with on a daily basis. I was frustrated that my iPhone started to feel like a worthless brick of technology. I realized I had built addictive tendencies (upon unlocking my phone, I felt my thumb reach for a space where the Facebook app no longer existed).
I also spent more time during the 30-day break than Iād like to admit staring at a completely blank page in my web browser, all the while thinking āwhere do I go on the Internet now?ā
I wrote a detailed article about my social media detox here, but at the end of those 30 days I decided not to completely quit all of social media. I did, however, not re-install the Facebook app on my phone (and later quit Facebook). I did notĀ add Facebook and Twitter back to my browser bookmarks. And I created a new structure for my usage of social media, which included visiting sites once in the morning and once in the afternoon.
If I just went back to it, was it worth quitting social media at all?
During that 30-day break I came up with multiple new business ideas, one of which brought in over $40,000 in revenue. The months prior to that I felt like I would never come up with a new idea again. My thoughts were always cloudy and jumbled.
After my 30-day social media break, I had a newfound sense of clarity and energy. I honestly felt like a different person. A happier person.
There are times when a short-term break just wonāt cut it and you need to make the call whether or not to drop something for good. Long-term quitting can be the hardest kind of quitting, but arguably the most necessary (and rewarding).
In 2010 my IWearYourShirt business was doing very well. It was profitable, it had a very devoted fan-base, and everything seemed to be humming along perfectly. Because of all those things I decided I wanted to give back and create my own charity or non-profit organization with a focus on something I was passionate about: t-shirts.
After multiple daily live brainstorming sessions with friends and fans of IWearYourShirt, I decided to try to achieve something big and get 1,000,000 t-shirts donated to people in impoverished areas of the world.
As this idea started to come together the support for it grew like a weed.
A local design and development company wanted to do all the branding and web work and an existing non-profit organization wanted to help handle all of the logistics (receiving shirts and finding rural villages around the world to take them to). Everything was clicking into place.
But then the backlash started. The company, called 1MillionShirts, found its way onto the laps of non-profit and charity activists and bloggers. They ripped the idea to shreds.
If youāre thinking āwhy the heck would they do that, this sounds like a great idea!ā you are not alone. I lashed out at some of these people, defending my idea with vigor.
I felt my intentions were in the right place and there were people all over the world who didnāt have clothing (specifically t-shirts). This was my chance to make a tiny impact with something I had an influence on.
But then a few non-profit folks explained the situation on the ground in these countries and areas where Iād never been but wanted to drop stockpiles of free t-shirts on.
They explained that by dumping loads of free clothing on people it would crush any micro-economies that existed where people were trying to make a living by selling their own t-shirts. It would also perpetuate the handout mentality that only reinforces the behavior of waiting for good things to come instead of making them happen on your own.
In short, I would be doing way more harm than good.
Thereās a lot more context and layers of conversations to share, but it was apparent to me that I needed to quit 1MillionShirts. It wasnāt just that I, personally, needed to walk away. Itās that I needed to shut it down (especially since over 12,000 t-shirts were donated within the first few weeks).
Did I think about pivoting 1MillionShirts into a direction that would provide the right value to people in need? Absolutely. I even spent hours on various Skype calls with non-profit organizers around the world trying to find the right answer.
But the stress, the anguish, the misaligned good intentions were too much. I was still trying to run a growing (and profitable) business which was getting the negative effects of also trying to build, pivot, and learn about non-profit organizations.
So I shut down 1MillionShirts a month and a half after it was announced to the world. After thousands of people reached out to support it. After I (and many other people) poured countless hours into it. I was extremely passionate about doing some good for the world, but I was doing it the wrong way and without enough knowledge of the space I was trying to get into.
Removing yourself from the quitting = failure mindset shows you just how much more can be accomplished when you free up time in your life.
Stop doing that thing right now. Take a deep breath, step back, and reflect on the time you spent doing what you were doing so you can apply it to your next big idea.
You donāt have to quit big things either. If youāre trying to get healthier, start doing yoga. If you hate it, quit it and try something else. If youāre trying to become a better writer, experiment with a completely different writing style for one week. If you hate that style, quit it and try another one.
Itās simply a step in the process. A step that should always be pushing you forward, not backwards.
Too often quitting gets lumped in with failure. But we all need to understand that these are two completely separate situations. Failure is typically something you canāt control, while quitting means youāre taking control of the situation.
Think of all the successful people you look up to right now. I doubt you can name anything theyāve quit. People donāt remember or dwell on the things you let go of. They care about all the amazing things that happened because you were strong enough to quit and move on.
These are stats and stories that Iāve never shared publicly before, not because I necessarily wanted to hide them, but because I had yet to come across an interesting perspective on failure beyond the whole āfailure teaches us lessons that lead to successā song and dance.
As you may well know by now, last week I was busy devouring page after page of (my spirit animal) Elizabeth Gilbertās latest treasure,Ā Big Magic.
To say I had a few ah-ha moments is an understatement. I feel like this book should be ordained the official spell book for creativity. Itās part mystical and intriguing, part practical and actionable.
In the book, Liz shares a quote about failure that stopped me dead in my tracks:
āFailure has a function. It asks you whether you really want to go on making things.ā
– Clive James
So often I feel like we hear about failure in the context of what it teaches us for the “next time” we try something. That failure makes us more prepared and experienced as we go on. I totally agree with that sentiment, however…
There is an underlying assumption with that advice that we WILL go on, that we will keep making, that we will try again.
What I love about the Clive James quote is that it takes one step back and points out that the FIRST helpful thing that failure has to offer us is the sometimes jarring confrontation of whether we even want to dust ourselves off and try again.
Failure presents us with a āworst-case scenarioā of sorts so that we can honestly ask ourselves:Ā Is the joy of making worth the pain of failure?
And if the answer is YES, well then we have a pretty strong clue as to the kind of work we feel called to do.
And if the answer is NO, well then we have a pretty strong clue as the kind of work we feel isn’t worth it to pursue.
In other words, failure is the most powerful and valuable kind of creativity litmus test there is.
Last year, when I was just a few months into building Made Vibrant, I could feel this idea for a book brewing in my mind. I was starting to experience the true joy that comes with unfolding a business based on my intuition, but I was a bit frustrated with the lack of practical advice on how others could tap into their own inner voice.
Thatās when the idea for Connecting With Your CoreĀ hit me. I wanted to share my personal journey to authenticity and provide practical, actionable steps for people to find their own core values and apply them to their lives.
So, I put my head down and I worked on this book for weeks. At the time, my design client inquiries had dried up a bit, I wasnāt making much money, and so financially it was definitely a gamble to shift my focus away from finding clients and into bring this e-book to life.
Finally, I launched it on June 24, 2014, and do you know what happened?
This happened:
Financially speaking, my first e-product was a failure. It cost me more money in time and missed clients than the revenue it brought in. BY FAR.
But, do I regret writing it for one second? Did it disappoint me so badly that I said Iām never going to write another book again, Iām never going to sell another product again?
Heck no. Why?
It called to me like a nagging whisper deep in my core and it would have been a shame to let it waste away still buried inside. Itās still one of the things Iām most proud of that Iāve ever created, so much so that I spent even more time re-vamping it and hand-illustrating it for the latest shop launch.
(Iād also like to point out that my next e-product after that book was my lettering e-course that has brought me over $45,000 to date. Just a reminder that you never know what’s waiting for you on the other side of failure.)
The āfailureā of my first product asked me that all important question:Ā do you still want to keep doing this?
The fact that my answer was a resounding yes told me that I create things and I teach and I express myself first and foremost for the deep joy that it brings me.
And thatās why I hope you create to. Because you have to. Because even the possibility of failure canāt deter you from bringing your ideas to life.
There are so many more of those stories that I could tell you about. Like the time I tried selling prints of my lettering work and just ONE person purchased. (Spoiler alert: I have not stopped creating art.)
The point is, I believe it would be a great gift to the world if we were all doing the kind of work that would continue to call to us whether we found ourselves in the pit of failure or not.
What is one thing you would feel compelled to do even if you knew you were going to fail? Even if you knew it wouldnāt bring you money or sales or success, what would you need to go on creating?
Now whatās one promise you can make to yourself in order to do more of THAT.
On Wednesday Iām flying to Brookings, South Dakota because Jason and I have each been invited to present a TEDx talk. Iāve been practicing and obsessing over whether it will be just right, if it will be TEDx-worthy, but just now as I type this I realized something:
Whether I do it ārightā or not doesnāt really matter. Because even if I were to fail, even if not a single person in that theatre felt moved or touched, itās okay. I will have shared the story that I feel I must share, and I will be happy that I got a chance to dance with my own inner muse on that stage.
So, this week, I want you to remember this:
View it as a tool to get you closer to the work that will light you up to your core.
A few years ago I spent about $150 on the entire P90x DVD set. This included all the DVDs, nutrition guide, theĀ official protein powder and a set of workout resistance bands. The late night informercials finally convinced meĀ that I was going to look like Tony Horton and all the successful “beach body” people in just 90 days. Spoiler alert: I failed P90x.
Once my package of death (I mean, P90x package) arrived I had all the tools at my fingertips to get in amazingĀ shape and become a much healthier person.
For those of you who might not be familiar with P90x, it’s a set of workout videos and a nutrition plan all guidedĀ by this ridiculously in-shape personal trainer named Tony Horton. You may notice the “90ā³ in the name, and that’sĀ because it’s supposed to get you ripped and in “beach body shape,” in just 90 days.
When I popped the first DVD in, starting my P90x workout schedule, I expected to start at P1X; Day one.
Something really simple and really doable on Day One, right?? Instead, I was met with a full-blown 52 minute chest and back workout, that included a 6 minute warmup. By theĀ end of the warmup I was drenched in sweat and I felt like my heart was going to explode (not a good sign).
IĀ knew at that moment, on just Day One, I was out of shape and was going to be fighting a painfully impossible up-hill battle.
While Tony Horton and all the other incredibly beautiful people in his workout videos were in great shape, I wasĀ not.
I will give credit to Tony Horton. Throughout every single workout video, he tells you toĀ “do your best and forgetĀ the rest.”Ā He shows you exercises you can do if you can’t do pull-ups, push-ups, whatever. It seems like he triesĀ to talk to people who are incredibly out of shape and give them hope and inspiration.
So I stuck with Tony and his P90x workout schedule. For 33 grueling days, I shoved DVD after DVD into the black box on my TV stand, and I didĀ my “best” and tried my hardest to “forgot the rest.”
Only,Ā my bestĀ never got to be good enough. And during every single punishing minute of every workout all I couldĀ think about wasĀ the rest.
I spent 33 days trying my hardest to keep up with Tony and the other people in his workout videos, only to feelĀ like I wasn’t good enough every single day. After that 33rd day, I finally gave up. It was after the stupid “Ab RipperĀ X” workout. I remember it like it was yesterday. I stopped mid “Crunchy Frog,” turned off my TV, tossed myĀ remote aside in disgust, collapsed on the floor and threw in my sweaty towel on P90x.
For many of us, this is the same experience we have with things associated with our businesses.
Maybe you’reĀ just getting started and you feel completely overwhelmed or you’re an existing business and you feel like you’reĀ stuck climbing never-ending uphill battles.
One thing that always killed me with P90x was that I felt like I was constantly behind. I was never doing enoughĀ reps of an exercise. I had to take frequent breaks while Tony and his crew moved on to another exercise I couldĀ barely do. Eventually I skipped large portions of the workouts because I felt so defeated. I don’t think the pauseĀ button on my remote ever got so much use.
In business you can feel the same way. Maybe you’ve laid out a specific launch plan or marketing strategy? AsĀ soon as you dive in (P1X) you find yourself overwhelmed, intimidated and hating the experience.Ā All you want toĀ do is quit.
This is the problem with trying to work at someone else’s pace, using someone else’s tips, tactics and whatnot.Ā You need to understand who you are and in what environment you work the best. Just because somethingĀ worked for another business doesn’t mean it will work for you.
Does it have the chance to? Sure. But if you’re not comfortable with the pace of whatever it is you’re working on,Ā you’re never going to stick with it.
Just because another business or person can do something the P90x way, doesn’t mean that’s the only way itĀ can be done. Take the bits and pieces you like, if any, and apply them to your own work. You definitely don’t wantĀ to get discouraged and give up.
As I mentioned, I only ended up doing P33x of P90x. I realized I could do much easier (and less timeĀ consuming) workouts and still see results. The process of starting P90x, while not my favorite experience ever,Ā did lead me to successfully getting back in shape in my own way and at my own pace.
I’m not even a baseball fan, but I completely understand the sport, and I know players won’t always hit home runsĀ (maybe if they did, I’d actually like it?).
Sometimes they only hit triples. Sometimes they only hit doubles. Sometimes they only hit singles. Heck,Ā sometimes they even bunt the ball. Triples, doubles, singles, and bunts are perfectly acceptable outcomes whenĀ a batter stands at home plate. The only thing they need to avoid is striking out (or never stepping up to bat at all).
When I watched the P90x videos, and I certainly did a lot of watching while catching what seemed like my lastĀ dying breath, it felt like I was watching a bunch of home run hitters. No one struggled like me. I simply couldn’tĀ relate to the people on screen that were supposed to inspire me.
What you don’t want to do with your business, the promotion of your next product or service, or your nextĀ marketing strategy is strike out.
Yes, you might swing and miss on a few things here and there, but you should beĀ able to learn from your mistakes without moving so quickly in the process that you’re bound to repeat them.
I completely understand the structure of P90x and how it works. The problem is that not everyone is wired likeĀ Tony Horton and his band of merry fitness freaks (er… merry men and women).
Because I felt so discouraged in the beginning and still felt discouraged on Day 33, I didn’t think 90 days wouldĀ be realistic for me and I gave up. In business, it’s easy to set goals and milestones, but it’s nearly impossible toĀ hit them perfectly. There willĀ ALWAYSĀ be things that come up and delay the process. Knowing this ahead of timeĀ and not handcuffing yourself to these things will keep you sane and able to deal with adversity whenĀ (not if)Ā itĀ comes.
I also never felt like I was celebrating the small victories in P90x. I only ever felt behind. With your business, youĀ should appreciate and enjoy the small successes that come your way. You should embrace the journey to reachĀ your bigger goals and not loathe every single sweaty moment of the process.
Doing P90x led me to creating my own workout and nutrition plan that worked for me.
I guess I do have toĀ thank Tony Horton’s abs for that.
We all have fears and feelings of resistance when it comes to our businesses. The key is trying to mitigate thoseĀ thoughts and feelings. To understand that they exist in our minds and to push past them and at least doĀ something.
Whether you’re just getting started or have a huge plan of attack, the best thing to do is start. From there you canĀ analyze and adjustĀ as you go. You will make mistakes, hit bumps in the road and eventually start to see success.
If thereās one thing Iāve learned about myself over the years, itās that Iām not afraid to put myself and my ideas out there. For some of you reading this, youāre the complete opposite (and thatās okay!).
Fear is something we learn over time. Whether itās from the people around us or the circumstances we live in. However, fear is also something we can overcome with effort.
When I graduated college I was getting ready to find my first ārealā job as a graphic designer. Iād done some freelance design work before graduating, but nothing substantial and nothing long-term. I remember a friend showing me a job listing for a graphic design job at a major sports agency. Immediately doubt and fear crept in. My portfolio didnāt contain any sports-related work. I didnāt have other sports-related experience. How could I land a job at a world-renowned company with almost no worthwhile credentials?
I remember asking myself all these āwhat ifā questions but decided what the heck and submitted my resume and portfolio (none of which fit the criteria of what they were looking for). A few days later I received an email and was asked to come in for an interview. Fear set in again, because now I had my foot in the door, but couldnāt hide behind technology. I had to sit in front of accomplished people and pretend I could do this job I applied for.
I took the interview and decided I wouldnāt pretend to be something I wasnāt. They asked questions about previous experience in the sports industry, knowing anything about that sport (which was tennis), and why I thought I was the right fit. I didnāt have great answers to any of those questions, but instead, I tried to be honest. I told them I was eager to learn and that it seemed like an environment Iād thrive in. I stood behind the work I had done and explained my processes and how I worked.
I distinctly remember being scared when they asked me to name five active tennis players and I couldnāt. But instead of letting fear paralyze me, I flipped the question back to them and asked them to name five principles used in graphic design. Just like I couldnāt name tennis players, they couldnāt name design principles.
The interview finished and a few days later I was offered the job. Had I let my fear of the unknown take over, I would never have gotten the job. A job that led me to meet a fellow designer, which led to my first entrepreneurial venture, which led to the idea of IWearYourShirt, which led to me doing more writing, which led to you reading this blog post (and many other things).
There are many moments in our lives when we have decisions that need to be made. Those decisions typically bring about fear and can seem daunting. One way I overcome fear is to ask myself āwhatās the worst thing that will happen if I do this?ā More often than not, there is no āworst thing.ā Thereās no outcome that I canāt survive.
Whatever the thing is that youāre afraid of doing right now just ask yourself:
Iām willing to bet if you answer that question honestly and really drill down, the fear you have wonāt be so paralyzing. In fact, the fear you once had might seem trivial.
If I can help you overcome a current fear you have, please reach out on twitter or email.