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In 2015, I hired my first ever assistant, the wonderful and talented Laura. We worked together for three years, and I still consider hiring her one of the best decisions I ever made for my business. I want to share with you a bit about what the process of hiring was like for me, and how I managed to overcome the big fear I had that the magic and mission of what I’ve built might become diluted with the addition of a new person.
The first two years of growing Made Vibrant was general such an enjoyable experience. I had the freedom and flexibility to experiment with different revenue models, and I had the luxury of teaching myself everything on my own time without having to worry about anyone else. For a while it felt like maybe I might always want things to remain that way, operating a business solo. Maximum simplicity, minimum responsibility to anyone else but myself.
That is until the end of 2015, when I looked up and realized running the day to day of the business was starting to make me feel a bit like one of those circus performers spinning plates on broomsticks.
Slowly I had been adding each new spinning plate—an Instagram challenge here, another new product there, a blog strategy, a creative practice, a Slack community. The list went on.
And all of those things were wonderful and helpful additions to my business, Made Vibrant. They brought me joy, they brought my business profit and they brought my audience value.
But I’d be lying if I said it wasn’t exhausting, what with all the constant running around and trying to keep all the plates from falling.
That’s when I started considering the notion that an assistant might be the right way to go.
I remember the exact moment it dawned on me that something had to change. I was sitting at my computer literally just staring blankly at my calendar, almost on the verge of tears because the minutia of all the spinning plates I had in the air felt virtually paralyzing. I had no energy to even tackle my to-do list because the weight of the whole thing had me in a chokehold.
That’s when I asked myself these two simple questions: 1) Is my business making enough money that I can afford to pay someone part-time? and 2) Am I willing to let go of some aspects of my business in order to make room for more of what I value in my life (creativity, curiosity, ease)?
The answer to both questions was yes.
The first thing I did was ask my close business peers about their experience with virtual assistants/hiring just so I could get a baseline understanding of what I was getting myself into.
I’ll be honest though, while getting outside feedback helped warm me up to the idea that this could be a great and helpful thing, it also actually made the process feel a bit more overwhelming than it needed to be because I realized there is no uniform way that people go about hiring assistants.
Every business is different and every business owner is different, so it’s no surprise that there isn’t a one-size-fits-all solution.
But the more people I talked to, the more I realized I just needed to figure out what worked for me:
Once I realized it was my business and I could run it how I wanted to, the process felt less overwhelming because I realized I was free to just be myself.
Now, before we move on to the process of actually finding my assistant, let’s wade together through some of the big fears that came up for me once I decided to dive in.
Ahhh yes. That all-terrifying, unpredictable, sneaky little booger called The Unknown. As with all things that I’ve never done before, my assembly of what-ifs received their call to arms and started showing up in record numbers once I decided to finally hire someone.
As in all cases of the great fear of the unknown, I simply had to remind myself to, hello, breathe, but then also to accept that I don’t know what the future holds and that’s okay. I’m a big girl and I can trust myself to know that I’ll figure out whatever gets hurled at me.
Yes, all of those big scary things are what-ifs, but there’s also a great number of what-ifs that could mean wonderful things too:
Basically, my tip for silencing the fear of the unknown is simply to say, “Hey fear, yeah I know we’re flying blind here but I’m a pretty seasoned pilot by this point so just trust me, I got this. Now sit back and enjoy the flight.”
This is probably going to seem like a weird one, but I was literally afraid of being required to talk to another human on a regular basis.
Now, before you internalize how bizarre that sounds, just know that I am in fact an introvert. I enjoy the deep thought that comes with being alone, in my own head, and while I can definitely enjoy connecting with people under the right circumstances, sometimes interacting at all can leave me feeling a bit… drained.
So, I think a part of me was a bit apprehensive about the whole communication part of the process. Would it drain me to be in constant contact with someone? Would it leave me feeling overwhelmed?
Again, though, once I realized that it was my business and I could mold the relationship to reflect my introverted self, the fear subsided. (Also, I’ve found in recent weeks that if you’re just honest with people in telling them what you need and how you work best, they’re usually pretty cool with being accommodating.)
Okay, so here’s the biggest fear of all. Somewhere in the back of my mind, I had to acknowledge:
How arrogant is that?! The truth is, I’m not the magic. Maybe I’m an instrument of it, maybe I help the magic get out into the world, but it’s not me or even the business itself; the magic is in what the business stands for. It’s in the honesty of telling one’s story, the beauty of listening when inspiration calls, the connection that comes from supporting other soulful creatives worlds away from you.
And that means that someone else out there can be an instrument of all that too.
If the right person shares my same values and can get behind the mission of my business, then if anything, the magic of the business becomes stronger.
Which brings me to…
Based on the fact that my biggest fear was diluting the core of Made Vibrant, the single most important thing that I was looking for in the assistant applications was a deep understanding and whole-hearted commitment to the mission of my business.
I mean it when I say: everything else was secondary to this priority.
Because even if someone was the most organized, most detail-oriented, most effective assistant ever, if what I’m doing doesn’t resonate with them in their bones, then I don’t think I would fully trust them to interact with the Made Vibrant community and pour that passion into whatever task they’re doing.
As an aside, my favorite and most unexpected part about hiring someone who believes in your mission? They can actually help ground you in your own WHY.
After simply interviewing Laura and chatting about Made Vibrant, she reminded me of the fact that among the various personal and professional development sites across the web, to her Made Vibrant stood out as a resource rooted in authenticity and relatability. When she said that, it actually served as a powerful reminder that I need to be doubling down on those things. It effectively helped me find my way back to the heart of why I started my own business.
Which is to say:
“If you hire the right person, they have the ability to strengthen your core purpose, not to dilute it.”
Here are the simple steps I went through to find the right assistant for me.
I went to my audience FIRST. If I’m going to find someone that is aligned my core mission, there is no group better qualified than my own audience. That’s why I started from the inside. I listed out the basic requirements of the position, what I was looking for and how to apply.
(Note: I included instructions to submit an email as an application rather than to simply fill out the form because I wanted to immediately be able to tell if people could follow instructions. You want to look for ways to further qualify your candidates so the actual process of submitting an application is one way to do that.)
Things you definitely want to include:
I made it a point to read and give my full attention to every email that came through. If the email followed instructions, the candidate had the skills/experience that I required and if the email was well-written with strong communication, I immediately whittled the stack down to those candidates.
From there, I went back through again and made note of those that felt particularly invested in Made Vibrant’s mission. I opened the door on this a bit when I asked applicants to include why they felt they were right for the position, but those that stood out to me were the ones that took that opportunity to communicate why their values were deeply aligned with those of the business.
Lastly, I knew that I wanted to narrow the field down to just a handful of applicants for live interviews. I simply didn’t have time to interview more than two or three candidates, so to get my list down to those few, I sent the top applicants some last final questions to dive a bit deeper. Some were skills-based, some were scenario-based to get a sense of how they’d respond to different situations, and others were simply to get an idea of how the relationship could grow in the future. Here are the exact questions I asked:
The answers to these types of specific questions actually made it fairly easy to identify three top candidates. Once they responded, we set up a time for a Skype interview the following day.
This step for me was more about finding the best personality fit. I knew going into it that I didn’t need to find a best friend, someone JUST like me, but I did want someone that I would enjoy communicating with on a regular basis and I wanted to make that personal connection before agreeing to set up the professional relationship.
This is when the choice became really clear for me. I think even in a virtual interview, you can get a sense of how you click with someone, where the conversation goes, how enthusiastic they are about working with you, etc.
My conversation with Laura flowed naturally and I got off the call feeling not only like she was the right fit, but I actually felt re-energized about my own business. I knew that was the kind of energy that was worth risking all the scary unknowns for!
Once I contacted Laura to tell her she got the gig, we got to work right away! I sent over a contract with payment terms, “termination” terms (ie. what happens if either of you want to end the relationship, and the basis agreement that she’d be acting as a contractor rather than an employee.) **Note: I’m not a lawyer so if you are going to draw up a contract, I recommend at least consulting with a lawyer.
Then we set up a kick-off call to bring her up to speed on what was going on with Made Vibrant and I trained her on some tasks. As we moved along, we updated and evolved the tools/processes that we used to manage our workflow. In general, though, we used a combination of Slack, Google Docs, and Asana to manage tasks, which worked very well.
Growing a team can be unsettling if you’ve never done it before, but after three years I can say it was MORE than worth it to feel like I had someone on my team rooting me on and who was invested in seeing the Made Vibrant vision come to life.
What if instead of walking the paths of other people, you created your own paths? What if boundaries actually became opportunities?
During the recession of 2008, when companies were cutting back all spending, I decided it would be a good idea to ask people to pay me to wear a t-shirt every day. Nearly everyone on this planet has purchased a shirt from a company and then walked around promoting that company without even really realizing it. I could have seen the recession as a boundary. I could have seen my lack of knowledge of social media or content creation (I didn’t even own a digital camera at the time) as a boundary. Heck, I probably should have seen the fact that I was a complete nobody living in a small relatively unknown town in Florida as a boundary.
But I refused to see any of those things as boundaries. I didn’t let any of them stop me in my pursuit of doing something that felt right to me.
You know the ones:
In 2008 I let those feelings start guiding my decisions. I stopped worrying about the fears and limitations set by other human beings (who are intrinsically no different than me). I started to give myself permission to chase down opportunities that I created for myself and that I alone had the audacity to try.
(Well, unless you’re a divorce lawyer I guess, then you are actually the only person on this planet that wants to hear about divorces). When my Mom went through a divorce a few years ago, it left me with a last name I no longer wanted. What do you do when you have to carry a name that doesn’t give you any meaning or sense of identity? During a difficult family conversation, I remember trying to add a little levity and said, “what if I sold my last name??” A pretty outlandish thing to say, right? Well, it’s an even crazier thing to think that it could ever become a profitable business idea.
When I finally mustered up the courage to write my first book, I asked people who had already written books for their advice. Almost every single one of them said some variation of: “Jason, you won’t make money with a book as first-time author, just use it as a marketing tool.” Even when I made the decision to try to get 204 companies to sponsor my book, I was selling something intangible that was difficult to explain (because it hadn’t been done before).
My point to these various stories is this:
You can accept boundaries and let them stop you from doing what you want to do, or you can look beyond them and see opportunities.
The phrase “this is how it’s always done” is not how things always have to be done. The first time I decided to look past a set of boundaries and trust my instincts, it was scary. It’s not easy doing things differently. It’s not easy standing out from the crowd. And it’s certainly not easy to execute unique ideas.
I am not an artist. I am not a musician. I don’t consider myself to have a skill set that is easily explained and confined in an easy-to-understand box. But I’ve come to embrace my un-confine-ability as one of, if not the strongest asset I have.
This is not a “How To” article. I don’t have 17 easy-to-do steps that can make you successful or better understand who you are as a person. However, I hope this article creates a small spark for you. I hope that it triggers something in you that helps you see opportunities beyond boundaries that are currently sitting in front of you.
No one is going to hand you a set of clearly defined directions that guide you to a successful future. The most fulfilling path in life is the one you create for yourself.
Give your internal voice a shot. In fact, give it multiple shots. Trust yourself and see what happens. You won’t get it right every time by listening to your gut, but believe me when I say that the validation you get from trusting yourself is incredible.
Fear is manifested. Unless you are trying to something you’ve already done before (with the exact same set of circumstances), you should do everything in your power to ignore fear. Understand that it exists in your mind, but don’t let it control you.
Instead, search for all the magic bullets: Search for better people to surround yourself with. Search for inspirational moments. Search for the steps that lead you to a business and life that feels congruent to who you are. Search within yourself to figure out what really matters to you.
When was the last time you actually invested in yourself? Whether that was a financial investment in helping you overcome a boundary in your life or a personal investment that increased your happiness and well-being?
If you give yourself the chances (and you’ll need more than one) to look beyond boundaries and see potential opportunities, the rewards will come. It may take time and effort, but things worth having always require time and effort.
There I was, sitting in my cubicle, photoshopping reflections off of a cellophane package. A meaningful task, worthy of the graphic design degree I was seeking at the time. I got asked to go into my boss’s boss’s office and was promptly fired due to company restructuring.
This was the first moment it occurred to me that working for someone else might not be for me.
Let’s rewind the tape a bit. It was 2002. I had just turned 20 years old. I was going to college to get a degree in graphic design.
The job was a part-time design internship at an Internet coffee company. You did read that correctly, somehow I’d found a part-time internship AND probably one of the very first Internet coffee companies. I was, at least, paid for the hours I spent airbrushing gray smudges off of clear plastic photos of coffee gift bags. Oh, and I also worked some real design magic when I whipped up the weekly email newsletter with the “Coffee of the week!” I can still remember the halloween edition and how proud I was of the clip art bats I carefully placed around the Pumpkin Spiced Dark Roast.
After six-ish months of photoshopping coffee beans, mugs, clear plastic bags, and clip art bats, my fruitful design career was coming to an end. I sat in a chair and listened to a man twice my age tell me, “it’s not you or your skill set, it’s that we’re going through growing pains” and “don’t worry, you’ll land on your feet” and “thanks for your time, grab a coffee bag of your choice on the way out.”
I was only 20 years old, I was barely making $200 per week, and this was the first and last time I ever got fired from a job.
But alas, I was just a kid. I was still in college. I didn’t have big hopes and dreams at the time. I didn’t have a ton of ideas. I didn’t have any entrepreneurial friends. All I had was the path that sat in front of me, a path that felt like it was the only thing available.
We’ve all felt this way. Like there’s only one path. Like there’s only one “right” way to do something. But what I’ve learned over the years is that there are more paths than we think and it’s up to us to invent our own path when the one laid out in front of us doesn’t feel right.
I couldn’t have imagined the life I have today back when I was 20 years old and getting fired from my part-time design internship photoshopping clip art bats. But I’m certain I wouldn’t have the life I have today without the experience of being fired from that less-than-amazing job.
A few years after that experience, I found myself sitting in another cubicle, yet again faced with the path that sat in front of me. I was at another design job, working for another company, running the very same rat race. I remember feeling completely unfulfilled, like I was simply in the wrong place. There were so many moments sitting in my second cubicle design job when I was reminded of that first coffee gig. I was constantly confronted with the same environment I had sworn to avoid at all cost. I remember thinking to myself: “There has to be more than this.”
But I didn’t get fired from my second design job. Instead, I created a plan to fire myself from that job. I created a 6-month plan after multiple meetings with a friend who was also fed up with the 9-5 world. We continued to commute and work for the companies that paid us a consistent salary, but we spent hours every evening building our first company. A company where people wouldn’t be able to tell us what to do. A company where we called all the shots. And a company where we could actually reap the rewards of hard work and effort.
After 6-months of double duty, I was able to leave the 9-5 world forever. I had no clue what my life would look like from that point forward, but at least I had learned that the 9-5 world was not the life for me.
Looking back now, it’s clear to me that in 2002, I had no well-defined values. How could I? I was 20 years old and just doing everything I thought I was supposed to be doing in life. In 2007 when I left my second (and final) cubicle job, I still didn’t have a clear set of values, but it was at that time that I started to really take a look at what I wanted out of life. That was the point I realized that just because other people did things a certain way (or had certain values), that didn’t mean I had to do them the same way.
That new path I started to create for myself in 2007 has taken many different diversions over the years. Just when you think you’re on one path, yet another one another appears. Then when you start going down that path, oops, here pops up another one. But, throughout those twists and turns, I’ve discovered what my values are, which continues to help guide me down the paths that appear before me.
As it relates to my life and business, control is my highest value. It would be easy to say I’m a control freak and leave it at that. But it’s much deeper than that. Control means that I am solely responsible for my daily decisions. No one can dictate the time I spend working, not working, traveling, watching hours of Netflix on end (Daredevil was soooo good), or anything else in my life.
But it hasn’t always been easy to take control of my life and my business. Just a few years ago I ran a business (IWearYourShirt) that I thought gave me full control, but really took almost all my control away. I certainly didn’t have a “boss” who could fire me at any moment, but without realizing it, I had built an unhealthy business that I couldn’t find my way out of.
The second value that’s important to me is flexibility. At a moment’s notice, I love being able to change my plans. If I start working on a new business idea and I don’t like it, I can stop. If an opportunity lands in my inbox that I never saw coming, I want the ability to be able to drop everything I’m doing and chase down that opportunity.
My schedule at my previous cubicle jobs was incredibly inflexible. I never realized how much of an impact that had on me until I created a lifestyle that allowed me to do whatever I wanted with my schedule. If I want to book a flight to Iceland tomorrow and spend the next week there, I have the flexibility to do that. I don’t have to ask anyone permission. I don’t have to use vacation time. I can make arrangements for someone to watch my dog Plaxico and I’d be on my way.
Everything I do now goes through my value filters of control and flexibility.
When a new business idea pops in my head, I make sure that it gives me full control at nearly every angle and continues to provide me the level of flexibility I’ve come to enjoy.
When a life decision appears in front of me, I ask myself: “Does this give someone else control over my life? Does this hinder my ability to live a completely flexible life?” If the answer is even a smidgen “no” to those questions, I don’t do it. Because, no matter how great the opportunity may look, if it doesn’t align with my values, it won’t be good for me in the long run.
I’ve been spending a lot of time thinking back to that moment in 2002 when I got fired from airbrushing clip art bats. I wonder how I ever allowed myself to be stuck on that path. How I ever lived or moved forward without having core values to filter my life and business decisions through. But I understand now that it’s necessary to go down the wrong paths.
You can’t recognize the right paths in life if you don’t know what the wrong paths look like.
I would encourage you to take a look at the path sitting in front of you. Is it the direction you want to be going? Do you have values that you can check your path against? You might not find the right path for years (it took me 13 years), but that’s okay. If you can take one step in the right direction today, the path you may not have ever seen coming will appear before you know it. But you have to be willing to take the step. You have to be willing to take a chance.
Your path and your values won’t just land in your lap. You have to go out and find them.
We’ve reached peak Hustle Porn. It seems if you aren’t working incredibly long hours, you simply aren’t working hard enough on your idea. If you aren’t constantly “grinding” and “putting in work” then you’re destined to fail.
Your business isn’t making enough money? You obviously aren’t hustling enough.
Do you know where trying to constantly hustle led me?
I had to stop working like I thought I should (and saw others doing). I had to redefine what hustling meant to me.
And yes, I completely made up the term “hustle bro.”
Listen, I love Gary Vaynerchuk as much as the next entrepreneur. I’d even call Gary a friend. But that guy plays on a different level than we do. He also has huge teams of people at his side. Gary can do what he does (constant hustle) because of a lot of behind-the-scenes factors. Oh, and let’s also not forget his DNA, which he openly admits is unique to him. Gary is the type of guy who has been wired for hustle since he was a little kid.
You and I are not Gary Vaynerchuk. We shouldn’t aspire to work like him. We should find our own version of hustle and work in a way that feels congruent with who we are as people.
There are so many inspirational quotes about working hard and hustling and making sacrifices and blah blah blah. Yes, some of this stuff can be helpful at certain times. But make sure you’re running your business (or your life) your way. Just because you work 90 hours a week doesn’t mean you’re going to be successful. Even if you model your work off of someone else who is successful, there are too many other factors at play that you can’t replicate.
Absolutely not. Most businesses require a lot of extra hours to reach certain milestones and desired levels of success. But there must be a balance. You simply can’t keep burning the candle at both ends and working until your fingers bleed (if you’re reading this and bleeding, please call a doctor immediately).
What I’m advocating is counteracting the time you overwork with time to underwork. I know exactly how it feels to see a never-ending to-do list. I know what the financial crunch feels like. I know how it can feel to think that just a few more hours of hustle will get you where you need to be.
You can’t pay your mortgage with hard work. You can’t buy groceries with a few extra hours of effort. You aren’t going to be happy with your business (or life) if you’re constantly working.
Hustling can provide you with experience. It can help you learn lessons. It will open doors that might otherwise be closed. But again, you have to hustle in a way that makes you feel like you aren’t overextending yourself and going to an unhealthy place.
Last year I took a break from social media for 30 days. During that time I found a new sense of clarity on my personal (and business) values. I slept better than I had in a long time. I started appreciating things in my life more that weren’t on a digital screen. Oh, and I came up with a business idea that brought in more than $40,000 in revenue. Not too shabby.
With a break in 2015, I stumbled into what could be labeled as my biggest and craziest idea ever, (buymyfuture).
Rarely does anyone come up with a great idea while pulling an all-nighter or after 14 straight hours of staring at a computer screen. All of my great ideas have come at times when I haven’t been working myself over time. I’ve just shared two examples, and I could go on. I never have groundbreaking ideas when I’m stressed to the max and overstimulated.
I believe in the hustle, but I also believe in balancing out the hustle with rest. Listen to your mind and body. Take breaks. Enjoy life. Realize that you don’t have to work every hour of every day just because some people think that’s a cool thing to do.
Take a moment to define what hustle means to you, then hustle that way.
“You can’t sustain this.”
“You need to take a break.”
“Eventually, you will burnout.”
Those were things that were told to me again and again in 2009 as I embarked on a business that operated 365 days out of the year. My inexperienced and naive self scoffed at the thought that my youthful invincibility would be tested.
Boy, was I wrong.
I felt stress and pressure, sure, but those didn’t inhibit my ability to do creative work. Yes, they added a tinge of difficulty, but they certainly weren’t insurmountable.
Out of nowhere, I felt like my creative spark was gone. I felt like I couldn’t come up with any new or interesting ideas. And I wanted absolutely nothing to do with my camera or my laptop thanks to filming more than 1,500 daily videos from 2009 to 2012. It’s now three years later, and I’m not exaggerating when I say that I’m only now feeling like I’ve overcome the disdain for my video camera.
I don’t bring up this topic so you’ll pity me. I also hope I don’t sound like a drama queen. I bring this topic up because I feel that many business owners, creative folks, and entrepreneurs are going to get blindsided by the evil bitch that is burnout, and I want to help you try to avoid that.
The other evening I had a discussion with friends who were both feeling burned out. I could see it on them, like a dingy, dirty, wet trench coat. They looked weighed down and tired.
I want to share a bit of context about these friends. They have two businesses they’re running. One business is established, is a well-oiled machine, and is profitable, but takes multiple hours every day to keep going. Their second business is a brand new business that they’ve been working on for months, but is just starting to see the light of day. The second business has a lot of technical details involved, customer support issues, and is all-around a bigger project.
As a group of us sat chatting in a circle on the floor of our living room, I could see it in their faces. A familiar look that I remember all too well. In most scenarios, I try to hold back a bit on being brutally honest (it gets me in trouble sometimes) but this time I recognized my former self in them and I wanted to get really honest about that.
What I shared with them (and what I’d like to impart upon you) is that burnout is not something you can simply work through.
There’s a difference between working long hours to get the job done and overworking yourself to the point of no return (that last one is burnout).
As soon as you see the signs of burnout, you have to attack it. And the best way to attack it? Take breaks. I know that sounds incredibly counterintuitive, but I honestly feel burnout is like an infection. The longer you ignore it and just let it fester, the worse it is going to get and the harder it is going to get rid of.
If you start to feel burnout creeping in, you have to take a step back. That doesn’t mean taking a week off to go to the Bahamas, but it does mean establishing time away from your work.
Your schedule could be a specific time, like the hours between 9 to 5 (especially if you work from home). Or it could only be a certain number of hours per day (and you stop, no matter what, when those hours are up). The important part is just that you create a schedule and then stick to it. I’d recommend starting with one schedule, trying it out for a week, and seeing how it feels.
It could also be very helpful for you to keep a journal of how you’re feeling. This might sound a bit “woo woo,” but if doing something that’s a bit “woo woo” helps you avoid an epic meltdown, then I think it’s worth doing. If you’re going to try a new schedule for a week, write in the journal every morning and evening. You don’t have to write a novel, just write a few sentences of how you’re feeling.
If you’re going to try journaling, I’d recommend doing it for a week with your current schedule and then another week with a schedule that allows you some breaks. After those two weeks, read through and see the differences between them. You may still have a feeling of overwhelming, but it might not be as daunting and you may not feel as stressed out.
In 2012, I pivoted my IWearYourShirt business to a new model and it was going well enough. I wasn’t swimming in money, Scrooge McDuck style, but things were looking a bit better. Looking back now, I can see that even the shift in my business didn’t help get rid of the burnout. Surprisingly, it actually seemed to continue to get worse.
We tend to think money is going to fix all our problems. But if you have problems before money comes along, and the problems don’t get solved, they’re only going to get worse with the stresses that get brought on by money (more customers to deal with, more employees, higher output of work, more pressure, etc).
Success is simply a byproduct of hard work. Success doesn’t fix problems. It doesn’t heal wounds. It’s merely an outcome.
The first part of asking for help is difficult. Trust me, I once waited eight entire months to send someone an email who I completely believed could help me out. Pride is a dangerous beast. But it’s the second part that comes along with asking for help that can really cause complications: actually taking the advice you get and doing something with it.
You aren’t doing yourself any favors if you muster up the courage to ask for help and then remain set in your old ways. Whatever you were doing up until the point of asking for help was leading to burnout, so it’s time to make a change. You certainly don’t have to take someone’s full advice, but maybe there’s one small thing you can start doing right away. That one thing might lead to another, which leads to another, etc.
For folks who own their own businesses, burnout is very likely to rear its ugly head at some point or another. You might not be dealing with burnout right now, and in that case, it’s my hope that this article gives you some semblance of preparation when you start to see some signs of it.
I don’t think we as entrepreneurs talk enough about the dangers of overworking ourselves or the negative feelings that can come with running our businesses, feelings like burnout. I hope this article reminds you that your business is not the only thing in your world. If you don’t take time and attention to care for yourself as you continue to follow your dreams, all the success you’re working so hard to achieve won’t be worth what you had to sacrifice to get it.
Take care of yourself and your business will follow.
Maybe you want to get sponsorships and have tried before without success. Maybe you want to get companies to support your blog, business, or idea, but don’t have experience landing deals. Getting a business to sponsor your next thing doesn’t have to be sleazy and is much easier than you think.
Since 2008 I’ve landed over 2,000 sponsorships with various projects. I’ve worn sponsored t-shirts, I’ve had a sponsored car, my trip to SXSW in 2011 was completely paid for by a sponsor, I even turned a 90-day fitness challenge into an opportunity to get paid to get in shape (yeah, that was awesome).
It took me years of trial and error to develop a system that works. I certainly made tons of mistakes, but I’ve also had some great successes. In 2013 I launched a sponsored book project that generated $75,000 in revenue (before the book was written!)
Getting paying sponsorships isn’t luck. It’s putting in effort and using techniques that actually work.
Below you’ll find the seven step process I’ve used time and time again to land sponsors for my various projects. This isn’t rocket science and you don’t need any experience. You just need to do the work and believe in what you are selling.
Your value proposition is a paragraph or two that clearly explains the thing you are trying to get sponsors for. For years I struggled to write a concise value proposition. What I found was that most businesses I reached out to asked a similar set of questions:
Answering these questions will help you create your value proposition. Your answers should range from 1-2 sentences and should focus on the specific benefits you will provide. Take a sentence from each answer and massage it into one 4-6 sentence paragraph. Here’s an example value proposition I made for a conference I was hosting:
The Amazingly Awesome Conference will focus on teaching people how to do marketing more efficiently and with better results. We’re inviting people who are passionate about marketing to join us in Jacksonville, FL on May 6, 2015. The conference will cap at 300 attendees and tickets go on sale to the pre-sale list on our website first (January 1, 2015). Our conference organizers have worked with companies like Starbucks, Nissan, Jockey, and are flying in some of the best speakers in the world including Name Drop, Name Drop, and Name Drop. We’re excited to make a dent in the marketing world and have our attendees learn new information and about new products.
This value proposition should be used in upcoming steps I’ll be sharing, on your website, to your email list, on social media, etc. Use the heck out of this thing!
Your existing network is one of your most powerful assets. Whether you have 100 contacts in your address book or 10,000, these people are your starting point. Here are four things to realize about this list of people:
Build a Google Spreadsheet (or Excel) with your contacts in it. I recommend column headings of Name, Email, Business, How You Know Them, Contact Date, Response?, Introductions?, and Notes. There are probably CRMs out there that you can pay for, but I like the simplicity of Google. We’ll talk about what to do with this list in Step 3…
A little trick of the trade for you: Don’t know where to find your existing contacts? Go to your email inbox or your text messages on your phone. The last 20-30 people you emailed/texted with are your first contacts. Boom!
There are some very important things to remember when you’re sending an email to your contacts about the thing you want to get sponsorships for.
Here’s an example email I would write to someone on my contact list for the conference I mentioned in Step 1:
Hey FRIEND NAME,
Hope all is well with you! Thanks again for dinner last week it was a blast. [IMPORTANT: You want to show these aren’t mass emails]
If you haven’t heard, I’m running an awesome conference on May 15, 2015 in Jacksonville called The Amazingly Awesome Conference. I’m super excited about it and I’d love to ask for your help on two things. It’ll only take you a minute or two, I promise!
1. We’re looking to secure sponsors for the conference. I was wondering if you can think of businesses owners that might be a good fit for me to pass along some information? If you do, I’d love a really quick email introduction! I’ll do the hard work from there ☺
2. Aside from those introductions, do you have any thoughts for me or feedback? Have you been to any conferences and remembered things you loved or hated? If you want, feel free to check out our website at amazinglyawesomeconference.com.
Really really appreciate your time and help with a couple introductions!
Chat soon,
YOUR NAME
Monitor the responses you receive from these personalized emails. I guarantee you’ll be surprised at how many paying sponsors show up if you’re offering something they think might be valuable to them. Be diligent in updating your Google Spreadsheet!
Landing a paying sponsor doesn’t have to be hard work! In this 2-course bundle, you’ll learn my specific 10-step process for getting over 2,000 paying sponsors. All the email scripts, spreadsheets, and sponsor pitches I’ve used that have worked time and time again. Grab the Sponsorships Course Bundle (now only $99!) and stop feeling overwhelmed when it comes to getting paying sponsors!
Pitch emails are different from emails to your contact list. Unlike your contact list, the people you send pitch emails to probably won’t have any context with you (or established trust). Because of that, keep a couple things in mind:
You can use a similar version of the email template in Step 3, but you’ll want to make sure you put your value proposition in the email. You can read more about sending pitch emails in this article.
Follow up emails are EXTREMELY important in closing deals.
Follow up emails work well because people are busy, especially people you’ve never emailed before. I, personally, tend not to respond to the first pitch emails I receive and wait for people who actually put in effort and follow up with me.
While following up can seem like a daunting task, you can actually streamline the process greatly by using FollowUp.cc. It’s a completely free service that let’s you put a time you want to follow up directly in the Bcc field of the first pitch email (ex: 6days@followup.cc would send you a follow up reminder 6 days after sending your first email).
If you’ve created a separate Google Spreadsheet for your email pitches (which you should), make sure to include a Follow Up column. Again, be diligent about updating this spreadsheet.
Want more info on follow up emails? Here’s a full article on it!
Let’s be honest. If you’re sending pitch emails, you will probably get some “Nos.” I’ve received plenty of them, but I don’t let them discourage me. Don’t get offended when someone says no and realize that people aren’t saying no because you’re a bad person, they’re saying no because:
As crazy as it may sound, I’ve turned multiple “No” emails into sales. This isn’t because I’m an amazing salesman, it’s because if I really wanted to land the deal, I’d try again a different way. Just sending a pitch email isn’t always the answer. Often times you need to get creative and think outside the box.
Read an additional article about not saying “no” for other people.
This one is simple. Don’t offer everything and deliver crap. You should plan to “wow” your sponsor with extra stuff they didn’t expect.
A quick example of this is the company Headsets.com:
For whatever thing you are trying to get sponsors for, make sure your pitch doesn’t sell a 2014 Mercedes Benz and deliver a 1982 Ford Taurus. You want sponsors to be happy enough that they come to you asking to give you more money.
We are all creative, but the folks who are known for it have spent time cultivating it, failing at it, and working at it.
It’s easy to look at any famous creative person and think that they’re naturally creative. It’s easy to assume their work just appeared and didn’t take hours/months/years of painstaking dedication. Much like the idea of “overnight success,” creativity is viewed as something that just happens. Well, I’m here to tell you that’s not the case. I’m here to share some examples of how anyone can cultivate and grow their creativity muscle.
Not an actual muscle like the ones bodybuilders sculpt and tone, but a muscle in the metaphorical sense. Some of us are born with the ability to barely workout yet look like a Greek god (assuming that we all view Greek gods as muscular genetic freaks). But alas, the majority of us aren’t so lucky and have to work incredibly hard to build muscle.
The important thing is that the potential is there inside of all of us. You just have to really want it.
None of these will cost you a single penny and all of them can be done right now. These are the exact things I’ve done to help create my crazy ideas: IWearYourShirt, BuyMyLastName, SponsorMyBook, BuyMyFuture, and WatchMeWrite.
I’m not just the president of hair club for men… oh wait, that’s a different article. Onto the 3 ways!
One way to work the creative muscle is to do an exercise I like to call “No Bad Ideas Brainstorming.” I break this exercise down in detail here, but I’ll briefly explain how you can do it right now with minimal effort.
Much like exercise, if you were to put in the work and do “No Bad Ideas Brainstorming” often, you’d come up with lots of creative ideas.
When it comes to being creative, you need to get out of your own way.
Let’s stick with the muscle metaphor and talk about getting in shape or losing weight. Yes, you have the option to eat a delicious cheeseburger with all the toppings, a large order of french fries, and a sugar-filled beverage, but consuming those things won’t get you in shape. By eating a poor diet, you’re limiting your own ability to get in shape. We all know that it’s possible to use willpower to overcome poor lifestyle habits but when it comes to being creative things get a bit more nebulous. There isn’t a real cheeseburger, fried potato stick, or soft drink staring you in the face.
You need to discover what is getting in your way of being creative and actively avoid it. You don’t expect six-pack abs to just show up with no effort, so why would you expect creativity to do the same? Trusting the process and putting in the work is the easiest way to keep you from putting up roadblocks in front of your creativity.
Too often we stay where we’re comfortable.
Don’t feel bad, as human beings we’re pre-wired with a pack mentality. We consume content from the same people on the same platforms. We steer clear of topics we deem controversial. We simply go through the motions and try to avoid discomfort like it’s the Bubonic plague.
Well I’m here to tell you that merely going through the motions will never help you become more creative or generate your next amazing idea. I’m also here to tell you that you absolutely cannot catch the Bubonic plague just by venturing beyond your invisible line of comfort.
To be truly creative you must push yourself beyond your comfort zone. You have to move into uncharted territory.
Lucky for you, we live in a time when information is unbelievably accessible.
We used to have to seek out inspiration. If you wanted to see priceless art, you had to go to a gallery or look at books filled with photos. Nowadays you can slide your phone out of your pocket, tap a glass screen, and you have images of all of the world’s greatest art just a few clicks away. How can you possibly be impressed and inspired by things that take almost zero effort to seek out?
You may find a bit of overlap, but something tells me you’ll find a lot of new resources that you never would have thought to read or investigate. And I know it may sound crazy, but read books! Especially non-fiction (although fiction can be a good source of inspiration, too). Just consume new and different content than you normally wouldn’t, even if it’s only 30 minutes per day.
It’s no secret that we’re over-inundated with notifications, pop-ups, alerts, unread icons, blah blah blah. Everyone knows we live in a society with too much information being thrown at us. Yet people don’t realize you can do things the same way you’ve always done them, especially as it relates to creative thinking and coming up with new ideas.
Think about this for a moment: When was the last time you had a great idea, thought, or revelation while you were elbows deep in scrolling through your inbox or newsfeed on Facebook?
It doesn’t happen. Random ideas occur in the shower, in the bathroom, on a walk, in deep conversation with someone, right before bed, right when you wake up, or any area in your life where you give your brain a little bit of space to do what it does best.
We’re not talking about Neil deGrasse Tyson here, although, he could be a great source of information for #2 if you’re looking to get inspired. Not planetary space, but mental space.
If it’s as easy as just giving your brain some mental space, why aren’t all of us coming up with the next printing press, light bulb, or iPhone? Because it takes more space than most of us are willing to allow. An uncomfortable amount, in fact.
A few years ago, I ran a business that was fueled by creative ideas. The amount of content created in that business on a day-to-day basis was overwhelming, but there seemed to be an endless amount of ideas. Looking back, I now realize why there were always ideas to be had—I allowed for space to fill up my creativity bucket.
On days when I would feel myself getting low on creative energy or ideas, I’d take a walk on the beach with my dog or my wife. I wouldn’t bring technology and I’d just let my brain wander. I wouldn’t always come up with great ideas while on the walk, but what did happen was that it set my brain in motion. The creativity muscle was put to work behind the scenes. It could have been days, weeks, or even months later, but a great idea would pop in my mind. These ideas didn’t come out of nowhere, they came out of the process of allowing for space.
Whether you have a beach, a path by your house, a hiking trail, or a forest, find a quiet place without noise or distractions. Personally, I’ve found that actually moving around and being outdoors allows the most mental space.
Remember, allowing for space doesn’t mean you have to lock yourself in a cabin in the woods for weeks on end. It could be as simple as a 10 minute walk every day. Or maybe even some (prepare for a dirty, over-and-incorrectly used word) meditation.
Simply having ideas doesn’t make you creative. We don’t remember famous inventors for all the inventions they thought of but never brought to life (they do have a ton of those though). We remember famous inventors for the things they actually built and created.
Give yourself the space, practice, and daily intention to become more creative.
Remember the fortune teller Ms. Cleo? She had a bunch of infomercials a decade or two ago and in a deep Jamaican accent would say “Call me now…” Well I’m putting on my Ms. Cleo fortune telling hat and making a prediction that you think you’re doing something well that you probably aren’t. What is that thing? Time management.
For starters, because I used to suck at it. And, if you’re like the majority of people I’ve ever talked to, then you don’t quite have your working hours and your schedule locked in either.
When people say “time is money” it’s absolutely true, especially when we’re talking about our businesses.
It doesn’t matter what industry you are in, what many entrepreneurs and small business owners don’t realize, is that our time is extremely valuable and limited. That may not be news to you, but what might be news to you is how much money you could be leaving on the table if you aren’t diligent about your hours.
Let’s all hop in the car and take a virtual road trip to Case Study Land…
My wife Caroline used to run a design and branding company called Made Vibrant. Her schedule was completely her own, which meant she not only had to manage her clients and work output but had to understand how to manage her time.
One afternoon Caroline was really frustrated. She told me she felt like her schedule was completely full, yet she wasn’t making nearly as much money as she’d hoped (a feeling we can all relate to). Having had experience owning a web design company, I asked her to do a simple hourly evaluation exercise with me…
We opened up her Google Calendar and I asked her how many hours she really wanted to spend on client work per week. Her answer was 5 hours per day (she would be at her computer for much more than that, but she knew she wanted to work on personal projects and other things as well). At 5 hours per day, I told her she should have 25 billable hours per week or 100 billable hours per month. If we took the hourly rate she was comfortable charging ($75 per hour), she should be able to make $7,500 per month.
Caroline was already working a full schedule and certainly wasn’t making $7,500 per month. Coming to a realization like this can be a punch right in the gut but that’s not always a bad thing. Uncomfortability can lead to change, which we absolutely saw with Caroline’s business!
This exercise showed her that there were inefficiencies in how she was managing her working hours. She realized she had been resistant to blocking off time slots on her calendar because it brought back memories of scheduling meetings and calls at a previous 9-5 job she didn’t enjoy. Our chat peeled back that layer and helped her understand she controlled her schedule now and could do it however she wanted. (This was critical!)
Hearing that she should be able to make $7,500 per month by working 25 hour weeks opened her eyes to the fact that she was wasting lots of hours every day in Internet blackholes (YouTube, Hulu, Netflix, social media sites, etc).
When she thought about increasing her hourly rate to $100 per hour, her potential monthly income would raise to $10,000. That was incredibly inspiring for her because it was absolutely achievable.
I’m happy to report that shortly thereafter Caroline invested heavily in scheduling her working hours throughout her day. She didn’t use any fancy apps or tools, she simply used Google Calendar and Google Spreadsheets.
Caroline doubled the amount of client work she could take on and doubled her revenue!
Caroline’s investment into her schedule greatly paid off in just a few short weeks. She went from making $1,500 – $2,000 per month in client work (and feeling stressed out) to double that number at $4,000 per month (and feeling in control)!
Was there still room for improvement? Of course. There always will be. But she increased her profits by 50% just by taking a hard look at how she was managing her working hours throughout her day/week.
Whether you own a business where you get paid by the hour or not, your time is money. You must understand that having an inefficient schedule is sucking the profits out of your business. All the hours you spend consuming content on the Internet (or doing things offline) could be invested in your business and help increase your profits.
It doesn’t matter if you’re a salaried employee or you get paid by the hour. I’d like you to take a VERY hard look at your schedule and write down a few numbers (not in your head, actually write these numbers down):
When you have that total number take a look at it. Are you currently making that much money? If you are, great! Keep doing what you’re doing (although I think there’s always room for improvement, myself included). If you aren’t, don’t get upset or frustrated. Now’s the time to take look at your daily schedule and see how you can remove distractions and create more efficient working hours.
1. Take a break from social media sites. If you feel like it’s hard to take a break from social media sites, or other Internet blackholes, download the (free) Self Control App and block those sites for a few hours each day. It won’t kill you to take a break from them and you’d be surprised how much work you can get done if you focus for a few uninterrupted hours.
2. Track your time. Use a fun (and free) time tracking tool like Toggl. If you have a project that you think will take 1 hour, use Toggl to see if your task really takes 1 hour. If it doesn’t, then you need to reassess your time estimation and workflow.
3. Record your screen for a full workday. This sound really weird, and I promise you don’t have to watch it back. But what this exercise can do is keep you honest about how often you’re drifting away from work into distractions. Think of this like a self-imposed big brother!
4. Go analog with your to-do lists. I used to love using the newest and best to-do list app. But what I realized is that I’m much more efficient at to-do lists when I write them down in a notebook and can physically scratch them off. Here’s an article I wrote that goes more in-depth on this topic.
All of us have profits hidden in our daily/weekly/monthly schedule. We can all be better workers. Take some time today to reflect on your working schedule and find all the areas for improvement (and profit!).
I want you to get better at completing tasks, managing multiple projects, and enjoying the feeling of accomplishment on a daily basis.
To-do lists are essential to getting things done. Lots of people ask me how I juggle so many projects, businesses, and ideas at one time. The answer: I’m a huge believer in to-do lists.
I think I’ve tried every to-do list app in existence, and I always come back to physically writing out my to-do lists. Here’s why:
When I used slick to-do list apps, I always found myself getting distracted and ending up on Facebook, Instagram, Twitter, or heading off to some other catacomb of the Internet. Unless you create and update to-do lists with all other programs closed and WiFi turned off, you will get distracted. It’s a fact of life.
I really want you to give writing out your to-do lists a shot because it’s proven to be so incredibly beneficial for me. There’s just something about physically drawing a thick line through a completed item on a to-do list. You can feel the accomplishment. You get to physically enjoy checking an item off your list. It’s just not the same when you highlight an item on a screen and hit the delete key (or format the text to strikethrough).
One thing that really helps me tear through my to-do lists is to rewrite them each day. That means I have to go back to the previous day’s list and rewrite all the to-dos I have not finished yet. It creates a built-in accountability mechanism to just get things done so you don’t have to keep rewriting them over and over again. When you type out your to-do lists you can copy and paste (that’s easy and effortless). But actually rewriting a list of things from the previous day is cumbersome and annoying. It keeps you very in tune with your progress.
My tools of choice for writing out my daily to-dos are:
I looooove using post-it notes for my most important daily to-dos. You can’t fit too many things on a post-it note and you can keep it in front of you at all times.
My go-to notebook is the Panobook created by Dan and Tom from StudioNeat. It’s a dot grid notebook, so if you’re a lined notebook fan, you’ll have to search elsewhere. There’s just something about the versatility of the Panobook that I really love.
This is one of the biggest problems with to-do lists: We don’t write specific small tasks, we write big picture items.
If you want to get the website up for your next business or project you do not want to put “get the website up” on your to-do list. That’s too big of an item. Instead, you need to boil it down into the smallest steps possible. Here’s an example:
That’s 16 individual tasks and there are probably 16 more that would be added in the process. You’d write this entire list in your notebook and then each day you’d write 3-4 tasks on a post-it note and knock them out. Rinse and repeat until you finish the project!
When each to-do item is something simple and achievable you can get it done and move onto the next one. Plus, this process of breaking down bigger tasks into smaller to-dos helps you avoid mistakes and forgotten steps.
Besides breaking to-do list items into smaller tasks, I also like having multiple to-do lists. As I mentioned, I use post-it notes and a journal to keep track of my written to-dos. Another thing I like to do is break to-dos into daily, weekly, and monthly lists.
The daily to-dos are on, you guessed it, post-it notes and are tasks I need to get done immediately. Once a to-do item is completed I cross it off with a nice fat Sharpie marker. Once all the to-do items on the post-it note are finished I can crumple the small yellow piece of paper up and throw it away (feels so good!).
The weekly to-dos in my notebook keep me on schedule for whatever project(s) I’m working on and give me a place to look back on how much I have (or have not) accomplished. I typically write out my weekly to-dos every Monday morning and refer back to them multiple times each week.
My monthly to-do list is almost always one 8.5 x 11 sheet of plain white paper that I tape to the wall in front of my desk is a constant reminder of everything I’m working on. These are the bigger picture items I need to stay focused on and seeing them in front of my face every day really helps!
This may seem like a lot of work for to-do lists, but it’s really only 5–10 minutes per day and well worth the effort.
To-do lists are my secret weapon to being able to launch a lot of projects. I want you to get better at taking action and accomplishing your work, which is why I’m sharing this simple to-do process with you.
If you constantly find yourself trying new to-do apps but never sticking with them (or worse, not actually getting your work done), switch to pen and paper and see how it goes. I have a hunch it might work better.
My grandfather told me something that his father told him. I had already heard this exact story, but as a theory of Albert Einstein’s. It turns out, it was actually a theory created by Sakichi Toyoda* in the early 1900s called the 5 Whys.
(*Yes, the car manufacturer Toyota. Why isn’t it Toyoda today? No clue!)
Mr. Toyoda’s original theory is great, but for the sake of progress, let’s assume by asking better questions you can reduce 5 Whys to 3 Whys.
The 3 Whys is precisely what you think it is–asking the question “why?” three times to get to the real root of a question or problem.
John Smith (JS) talking to his boss: “I think I need to quit, I really don’t like my job.”
John’s Boss: “Why don’t you like your job?”
JS: “The atmosphere isn’t what it used to be when I started. It feels toxic and I never used to hate showing up for work, but now I do.”
Boss: “Why do you hate showing up for work?”
JS: “The culture that existed when I started working here has changed. It’s just not the same.”
Boss: “Why do think the culture has changed?”
JS: “Well, it’s that new guy, Tom. He’s so negative. He has a comment for everything. He’s frustrating to be around and really hurts our team’s dynamic.”
BOOM! In this fictitious, but incredibly realistic scenario, you can see how asking the question “why?” three times revealed a much deeper and more specific issue. If John Smith’s Boss had just accepted John’s distain for his job without asking why, he could have lost an important employee. Instead, by digging to the core of the issue, he found that John didn’t hate his job at all, he actually had an issue with another employee.
This theory doesn’t just work in fictitious scenarios. I use it fairly often to vet my projects and new business ideas. Here’s an example from when I was co-creating the online learning platform Teachery:
Me: “I want to create an easy-to-use online learning platform.”
My Brain: “Why do you want to create that?”
Me: “Because I’ve looked at other platforms and they all seem too complex and overpriced.”
My Brain: “Why do think other platforms are overpriced and complex?”
Me: “Because they’re not doing things simply enough.”
My Brain: “Why aren’t they doing things simply enough?”
Me: “Because doing things simply is difficult!”
From this little back-and-forth with myself I discovered the crux of how I wanted to build Teachery (simplicity for the end user!).
I’m 100% sure that other online learning platforms have said they wanted to create a simple online learning tool, but I know for a fact most of them (maybe with exception to Teachable) got lost along the way. Maybe lost isn’t the right word. They got distracted along the way with new features and requests.
A few years ago, I read the book Insanely Simple: The Obsession That Drives Apple’s Success. At the time I was just starting to build Teachery with my co-founder Gerlando.
It’s not a coincidence that “why?” is a very simple question. It’s an important realization that we all need to go a few layers deeper before doing important things. Whether it’s creating a new business, adding a new feature to a product, hiring a new employee, buying something expensive, having a tough conversation with a loved one, etc.
Disclaimer: please don’t act like a parrot and just say “why, why, why” when having a conversation with someone else, especially a loved one! I don’t want to get in trouble for that. Also, if you want to follow Mr. Toyoda’s original theory, feel free to ask 5 Whys or however many more it takes.
