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Hey There!

We are
Wandering Aimfully—

UN-boring business coaches 👨🏻‍🦲👩🏻‍🦰 who help online business owners like you earn more so you can live more.

We share free resources in the form of 📃 articles, 📜 guides, 🎬 YouTube videos, and 🎙 podcast episodes. We offer a 🦄 monthly coaching program (that's un-boring) called WAIM Unlimited that includes COURSES, SOFTWARE PRODUCTS, WORKSHOPS, and a thriving Slack COMMUNITY.

WHO RUNS THIS SHIP? 🚢
Glad you asked. That would be us— Jason 👨🏻‍🦲 and Caroline 👩🏻‍🦰 Zook!
Very nice to virtually meet you! Here’s a quick silly video from us so you can decide if we’re cool enough to be your friends. (Spoiler alert: we’re not…but we hope you decide to hang around anyway!)

We believe…

...in working to LIVE, not living to work.
...in rejecting the norm and carving our own paths.
...embracing your uniqueness is the key to running an authentic business.
...we are better together and helping each other will allow us all to succeed.

If this lines up with what you believe too, keep reading!

Our Story

Hello again! It's us, Jason and Caroline.

We’re creative business owners 🤓, best friends 👫, and oh yeah, as of March 2017, we’re also married or whatever 🥂.

Since we got together in 2010, we’ve made things in a slew of different ways, both together and apart. Caroline was first employed by Jason’s crazy t-shirt marketing company, getting her first taste of work-from-home-life (AKA: wearing a robe to work). After that we had separate businesses for a few years. Caroline created Made Vibrant, which started off as a client business doing brand design and transitioned into a digital product business. Jason got even weirder by selling his last name, writing a fully-sponsored book, and then selling his future. We’ve also built software products and sold physical goods.

Between the two of us, we've just about done 👏 it 👏 all 👏.

Now we’ve teamed up again to create Wandering Aimfully, an un-boring coach program that embodies what we hope to bring to the world. We want to encourage more people to create meaningful work they love, earn a good living doing it, and live a life that feels successful on THEIR terms, not the terms laid out by society.

Through every twist and turn though, the thing that has stayed constant is our desire to evolve our businesses to fit our personal values, rather than compromise our values to chase “success” with our businesses.

Our Core Values

If these things resonate with you, you’re definitely in the right place!

TRANSPARENCY

Most business owners only want to show you perfect moments. Not us. We share the good, the bad, the ugly.

AUTHENTICITY

We’ve gotten where we are by being 100% ourselves and we feel the best when we lean into who WE are.

HUMOR

There were two peanuts walking down a dark alley, one was assaulted. (Get it?? Nut puns!)

POSITIVITY

We don’t play the negativity game around here and sure, life isn’t easy, but we love focusing on the good stuff.

ORIGINALITY

The way we measure success is by putting our original ideas out into the world and standing by them.

INTENTION

This is the “aimfully” part of what we do and we’re pretty serious about doing the things that really matter to us.

CURIOSITY

We looooove trying new things, having new experiences, and stretching our comfort zones.

ACTION

A bias toward getting things done is in our DNA and crossing off to-do lists makes our hearts happy.

SPINDRIFT

Former fans of LaCroix, our fizzy water of choice is Spindrift. Same as Kristen Bell. So… besties??

DONUTS

You can’t live a good life if you aren’t eating delicious vegan donuts. ALL THE DONUTS PLEASE.

Some things you might find interesting about us…

🗺 Travel
We’re strong believers in having unique experiences and seeing different parts of this big world! However… we’re not backpacking, hostel-staying travelers. We love a great boutique hotel, with comfy robes, and lots of locally-sourced food. Oh, also, we currently live in Portugal 🇵🇹.
✨ Minimalism
In 2013 we discovered minimalism and it changed our lives forever. We emptied our closets and eventually sold all our belongings and moved on from a former life/place that wasn’t serving us. Being a minimalist doesn’t mean you own only one chair, it’s about only owning things that truly bring you value.
😬 Balance

We aren’t going to pretend we have the perfect work/life balance. In fact, we call it work/life blend. However, we’ve spent years figuring out how to have our work fit into the lives we want to live (not the other way around). Also, Jason somehow has better balance at 6’4 than Caroline. 🤷🏻‍♂️🤷🏻‍♀️

🐶 Plaxico
October 6, 2006 - March 6, 2020 🥺🌈🐶. Our 'Staffy' Plaxico brought us so many amazing memories during his 13.5 years of life. He snuggled with us during meetings on the couch and often let us know when we were working too late and needed to take a break to give him scratches and love. He will be missed terribly but was SUCH A GOOD BOY!

Things we've made 🛠...

Below you’ll find a list of nearly every project we’ve worked on during our time as entrepreneurs. We chose to share Active, Past, and Failed projects because it would have been easy to just show the highlight reel of successes, but that’s not the full and true story. With exception to a few projects, everything we’ve created is exclusively available in our Wandering Aimfully Unlimited program.

✅ Active Projects
Wandering Aimfully Unlimited
This is the big kuhana! Our BUY IT ALL NOW option that gives access to EVERYTHING we’ve ever created or will create for one low monthly price. All the tools and support you’ll need to realize your creative dreams.
Ready to join?
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Teachery
Launched in 2013 as a simple WordPress theme, Teachery eventually brought on an awesome co-founder and due to popular demand, was turned into a legitimate piece of online course software. Simple to use and plans start at $49 per month.
This is included with Wandering Aimfully Unlimited!
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Your Brightest Life
Your Brightest Life is a guided creative journal, traditionally published by Chronicle Books, designed to introduce you to yourself and discover how you can bring more YOU to your life via fun prompts, exercises, and more!
Get Your Brightest Life on Amazon.com
Buy Now
Own Your Weird
Jason's second book took nearly 3 years to release but it's finally here! If you want to figure out how to own your unique traits and live a life that feels more congruent to WHO YOU ARE, Own Your Weird is for you!
Buy Own Your Weird
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👋 Past Projects
IWearYourShirt
In 2008 Jason saw an opportunity to leverage growing social media platforms and connect brands and people. Over $1m later, Jason had worn over 1,600 shirts, hired a handful of employees, and then had to shut it all down.
Creativity For Sale
In 2014 Jason set out to share a bunch of never-before-told stories of what it took to create IWearYourShirt and (hard) lessons learned working for yourself and getting caught up chasing success. Over 120 5-star reviews can’t be wrong!
Get Creativity For Sale on Amazon.com
Buy Now
Better Branding Course
With 4 modules and 26 lessons, this course will take you through the step-by-step process of uncovering what makes YOU unique and baking that into a visual presence that cuts through the clutter!
This course is included inside Wandering Aimfully Unlimited!
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Better Lettering Course
Learn the basics of hand-lettering and how to create beautiful hand-lettered sketches from start to finish. This fundamental course has helped thousands of people start their own hand-lettering journey.
This course is included inside Wandering Aimfully Unlimited!
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iPad Lettering For Beginners
Take hand-lettered graphics to a whole new level with your iPad! Learn what the iPad Pro and Apple Pencil can do to spark your creativity, create custom art, or add one-of-a-kind lettering to your online presence.
This course is included inside Wandering Aimfully Unlimited!
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Podcast Like A Boss
Jason, Paul Jarvis, Kathleen Shannon, and Emily Thompson team up to bring you a fun and education online course that walks you through creating, launching, and running a successful podcast that helps your biz grow.
This course is included inside Wandering Aimfully Unlimited!
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ofCourseBooks
Created alongside Paul Jarvis and Zack Gilbert over the course of a 12-week podcast season, ofCourseBooks is a simple workbook software that was sold to a Wandering Aimfully member in 2017.
Bumpsale
Based on the incremental pricing structure that launched Jason’s IWearYourShirt business, Bumpsale is the fastest way to create a for sale button that you can put on your website and sell anything with fun and exciting “bump pricing.”
Build Your Digital Brand
In this online class exclusively available through Brit + Co, you’ll learn how to get your blog or brand VISIBLE online. We talk about identifying your ideal audience, designing a unique brand identity and establishing a content strategy.
BuyMyLastName
In 2012 Jason found himself with a last name he no longer wanted due to a family divorce. Having worked with hundreds of sponsors by this time, Jason decided to auction of his last name (twice!) generating over $100,000.
How To Get Sponsorships For Anything
Jason’s first foray into the online course world. Using the years of experience and lessons learned, this comprehensive course about landing sponsorships for blogs, events, etc, was created.
ONLY available in Wandering Aimfully Unlimited!
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Your First E-Course
Everyone has something to teach, and this beginner’s level course will show you how to turn your knowledge and experience into an online product you can be proud of (and one that makes you money too!)
ONLY available in Wandering Aimfully Unlimited!
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Finish Your Damn Book
Paul Jarvis and Jason teamed up to create a step-by-step process to help nonfiction authors finally finish their damn books! With six books between them, they have no trouble teaching people how to finish their writing.
ONLY available in Wandering Aimfully Unlimited!
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How To Get Sponsorships For Podcasts
At the demand of his audience, Jason created a second course about sponsorships, this time focused solely on the popular medium of podcasting. This is the most in-depth course and making money with podcasts.
ONLY available in Wandering Aimfully Unlimited!
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Draw Your Memories
In this drawing class, Caroline shows you 30 days worth of drawing prompts designed to conjure up joyful memories from your past, spark your inspiration and improve your illustration skills!
ONLY available in Wandering Aimfully Unlimited!
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Acrylic Explorations
Explore your own creativity and learn the basics of making abstract art with acrylic paint! You’ll learn three different techniques you can use to create your own one-of-a-kind abstract art!
ONLY available in Wandering Aimfully Unlimited!
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Connecting With Your Core
In this guide, you’ll find that elusive but oh-so-important voice in your heart -- your intuition! You’ll start speaking the language of your intuition, uncover your core values, and put those values into action in your life and business.
ONLY available in Wandering Aimfully Unlimited!
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YourPack
If you manage a community of any kind and want a simple way to be able to organize and search your members, Your Pack has you covered. A straightforward social directory tool that takes minutes to set up.
This is included with Wandering Aimfully Unlimited!
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SponsorMyBook
When Jason set out to write Creativity For Sale he knew he didn’t want to be a first-time author that made no money. Instead, 200+ sponsor messages were sold at the bottom of each page of the book, netting $75,000!
WatchMeWrite
For Jason’s second book, he had a public-facing live view of his writing document created so anyone could watch him create the first draft of his second book. What author wants anyone to see their first draft?? Jason. That’s who.
Product To Profit
Nathan Barry, Paul Jarvis, and Jason strip away all the nonsense when it comes to building and selling your first digital product. This masterclass also helped teach how to grow and audience and how to launch again and again.
This course is included inside Wandering Aimfully Unlimited!
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EasyCourse
Jason partnered up with his fellow tall entrepreneur Omar Zenhom (host of the Best of iTunes podcast $100 MBA) and created a no-brainer online course that gets people through each step of the online course creation process.
This course is included inside Wandering Aimfully Unlimited!
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Imperfect Writer
This is the course Jason wish he’d had when he started writing many years ago. His amazing editor Chantel Hamilton provides actual wisdom, while Jason shares tips on how to hone your voice and write non-sleazy sales copy.
ONLY available in Wandering Aimfully Unlimited!
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One Week To Profit
A 7-step, 7-day guide that uncovers hidden profits in your existing business. There are no silver bullets, but there are absolutely dollars waiting to be found if you know where to look for them.
ONLY available in Wandering Aimfully Unlimited!
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BuyMyFuture/BuyOurFuture
Jason sold access to his future in 2015 and 2016, then Jason and Caroline sold their combine future in 2017 and 2018. This project morphed into the Wandering Aimfully Membership and had the same awesome value.
Sleeping With The Boss Podcast
What’s it like to be in a relationship when you work for your spouse? What happens when you have to fire your spouse? How do you work and live together? Those questions were answers in a short podcast we hosted in 2015.
Dear Book Publisher
Not willing to do anything by the books (hey, get it!?), Jason created an open letter to traditional book publishers and agents in hopes of landing a deal for his second book. And guess what? It worked!
JasonDoesStuff
Jason’s digital man-cave from 2013 - 2018. Hundreds of articles written, countless projects created, and one easy to remember domain. Jason still does a lot of stuff, it just now lives here at Wandering Aimfully.
Made Vibrant
Caroline’s virtual home from 2013 - 2018. Following her heart, she created a community of soulful creatives that she helped with her art, her writing, and her experiences. Made Vibrant still exists as an editorial arm of Wandering Aimfully.
🙅🏻‍♀️🙅🏻‍♂️ Failed Projects!
Emojibombs
Not necessarily a total failure, since the goal Paul Jarvis and Jason set for Emojibombs was just to have some fun and create a project in 24-hours. This daily emoji story (sent by email) was quickly shut down, but was fun to build!
Spruce Metrics
We gave Spruce a REALLY strong try but just couldn't get the app and partnership to work. Maybe in the future something like Spruce will come back around? For now, it's a failed project.
Color Your Soul
Caroline’s first membership community! Color Your Soul was part digital magazine, part learning community, part art gallery... all centering around one mindfulness theme every month.
1MillionShirts
In 2010 Jason set out to make a difference with a lofty goal of getting 1,000,000 t-shirts donated that could be given to people in need around the world. Unfortunately, Jason didn’t know anything about NGOs and shut this down.
Only Human
Jason’s very first “startup.” Co-created with his design partner Dennis Eusebio in 2006, Only Human was a place to share stories and lessons learned from those stories. It didn’t take off, but it generated a ton of design clients for them.
Saddles for Corgis
This is a fictitious project that Jason has joked about on his /now page for years. Wouldn’t it be fun to see corgis wearing little saddles!? Jason thought so too! But truthfully, this business won’t ever exist… or will it??
Unicorn.pizza
The idea was to create an online store that ONLY sold unicorn or pizza themed products. That’s it. What, you’re surprised this project is in the failed section? Well, that’s just mean of you.
Dawn App
Do you remember the Sunrise calendar app? Jason adored it and when it shut down he was sad. He cobbled a team together to build a similar calendar app, but couldn’t get early customer support so the project was tabled. #RIPsunrise
T-shirts For Entrepreneurs
Caroline put her hand-lettering talents to work creating t-shirts that would be motivating and inspiring for entrepreneurs. We ran this little online t-shirt store for a year before realizing how low the margins are on t-shirts. Oh well!
Want to get ALL of our active, past, and future projects? Grab Wandering Aimfully Unlimited now...
YAASSSSSS!