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When Do You Shut It Down and When Do You Keep Going?

February 15, 2019

Is there a project or idea you’re working on right now that you feel you’re at a crossroads with?

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 “software startup founder.” 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, whatever… it’s 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 don’t 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 here’s the real-talk for you…

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.

Take ofCourseBooks, for example. It was (and still is) a very simple embeddable workbook product.

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 didn’t take a ton of continuous effort on our parts, we had certainly hoped it would generate more revenue. We didn’t even have wildly ambitious financial goals, we simply hoped we’d get to $10,000 MRR.

This is a similar story for me with almost every software product I’ve built. They are able to generate some monthly revenue but it’s never enough for one of them to earn the majority of my focus. And there’s another problem…

I’m not sure I’m cut-out to only work on ONE product for an extended period of time. I’m tired of beating myself up about that.

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:

  • Hosting live demos of the product
  • Having 1-on-1 calls to make the sale
  • Doing customer service
  • Creating ongoing content around the problem the software solves
  • Building and sharing case studies from customers
  • Having some sort of referral program and managing that
  • Constantly fighting the battle of churn
  • Knowing what features are most important to spend time building
  • Etc etc

There are probably 20 more bullet points I could list out and that’s precisely why I don’t think I’ll ever run a software company as my sole gig.


What Happens When Your Identity Is Tied To Your Work?

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.

What happens when a project becomes part of who we are?

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.

I’m not willing to stay trapped working on one thing or one idea for the fear of what other people might think of me. I don’t think you should stay trapped either.

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.


Do You Always Feel Like You’re On The Edge Of Success Or Failure?

No matter what type of product or idea you’re building, it can feel like you’re always on the edge of success or failure.

The Edge of Business

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 it’s 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.”

We need to quit projects that aren’t serving us any longer to create space for new things.

Or, you know, just create space and NOT IMMEDIATELY FILL IT. (That’s as much a note to you, dear reader, as it is to future Jason).

For me, and maybe for you, it’s important to sit down and really weigh the options with whatever you’re currently working on that isn’t bringing you the value you’d hoped.

Value = Revenue + Enjoyment

During the past year, I’ve decided that I’m not going to keep dragging projects along if they aren’t bringing me value. The revenue isn’t the most important indicator, in fact, it’s 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.

Where do you REALLY want to be spending your (work) time?

That’s 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 I’m constantly chasing after growth, even a small amount of it.

I’m in my “zone of genius” when I’m doing weird things. When I’m 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.

So how do you find the balance? What’s the answer?

I’m 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 you’re 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.

Give yourself permission to gracefully exit a project (whether that means making some money or $0.00).

A special thank you to Reed and J.P. who are the owners of two web apps I co-founded.

Slowly but surely I’ve realized that I can’t manage and run five different software companies.

It’s actually not even the marketing and time investment that’s the issue, it’s 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 “exits,” as they say in this business. Those exit amounts won’t impress you, and truthfully, that’s not really the point of this article. I do want to acknowledge that I’m grateful to have a community around me that believes in the products I’ve built and are willing to invest their money and continue working on those ideas.

Removing projects from my virtual plate is not only creating more time for new ideas (or existing neglected ideas) but shutting down projects is also helping to create mental space I didn’t even know I was missing.

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?

Why and When You Should Make a Business Pivot

January 20, 2019

Don’t Need Video? Listen Now

Episode Summary

Is your current business not quite serving you? Making a business pivot can look like many things:

  • Switching from one type of business to another
  • Scrapping all your current offerings and changing it up to something else
  • Getting rid of a bunch of features and try a slew of new ones
  • Or quitting a business completely! (which you shouldn’t feel bad about!)

We go through all these different types of business pivots and share stories from our various business ventures since 2007.

We’ve had our fair share of business transitions and believe it’s 100% okay to make a change but it can be hard to know when and how. Hopefully, our experience and advice in this episode will help you if you ‘re in a position where you want to make a change!

QUESTION FOR YOU: Is your business currently in a state of flux and feeling like you need to switch things up? (Feel free to comment with your answer on YouTube).


Episode “Sponsor”

Wandering Aimfully Memberships

Our show will remain sponsor/ad-free and you can support us by becoming a Wandering Aimfully Member. Our monthly membership program offers our brand new program Build Without Burnout as well as “The Vault” (all the courses, workshops, and software you’ll need to run your online business) and you get access to an amazing community of creative small business owners to help inspire, motivate and support you. Learn more about our membership here.

Why I Stopped Running A $1,000,000 Business and How To Know If You Should Quit Your Business

January 10, 2018

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 you’re 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, let’s back up half a sentence to that breaking point I mentioned. What was it, how did I realized I’d hit it, and what triggers should you be watching out for in your own business?

After generating $1,200,000 in revenue in five years, I decided to shut down my IWearYourShirt business and completely walk away from it.

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 “fans,” which was really odd.

Jason Zook IWearYourShirt in 2008

(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. I’d done nothing worth talking about. This was my moment to shine. The external validation showed up in many ways:

  • Money
  • Emails
  • Press/Media
  • Social media followers/conversations
  • Website traffic
  • Letters in the mail (no joke)
  • Additional money
  • Requests for interviews with famous entrepreneurs
  • Requests to speak at events
  • Pats on the back from friends
  • Phone calls, text messages, etc etc etc

As time went on with IWearYourShirt, I craved more. More validation. More growth. I saw other entrepreneurs becoming successful at the same time and I wanted to be on the same “level” as them.

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 that’s what I should be striving for. Everything I was thinking was growth-focused, and if you’re 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 didn’t 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).

Here comes the not-so-delicious recipe for business disaster and when you know it might be time to quit your business…

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 didn’t make sense, neither did me trying to take on ALL the roles in the company: CEO, CMO, CFO, COO, any C’s and any O’s, 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, can’t 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 wasn’t 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.

When everything is crumbling down around you with your business, you will reach a breaking point.

In 2013 I attended a conference in Fargo, North Dakota, where I was a featured speaker for a small, but awesome, group of fellow “misfits” (entrepreneurs, doers, thinkers, artists, musicians, etc). The event was appropriately called Misfit Conference.

Jason Zook at Misfit Conference 2013

When I took the stage, everyone expected to hear my story of t-shirt wearing success. Many folks in attendance had heard of “the t-shirt guy” and were ready to listen to all my business victories and triumphs. But something in me just couldn’t do it anymore. Something in me couldn’t pretend everything was okay. I was in debt. I hadn’t 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.

Instead of telling my story of success (which I’d told countless times from countless stages before that) I shared my failure-ridden behind the scenes of IWearYourShirt.

I don’t 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 people’s ideas of success. And then I remember the end of my talk, seeing tears in some of the audience member’s 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 to know if you should quit a business?

How did I go about quitting my business and how can you decide if you need to quit running a business that’s 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:

  • What matters to YOU?
  • What do you ACTUALLY value in your life?
  • What do YOU want a typical day to look like?
  • And maybe most importantly, how much is ENOUGH? How much money? How many customers? How much time spent working?

Every decision I’d 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 weren’t 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 didn’t need tons of people to see those things or give me praise for them.

Drawing a line in the sand is the first step to walking away from a business that needs to be shut down.

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 we’d used. $100,000 was my line in the sand and I didn’t 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 didn’t have a plan of attack moving forward, but I knew I had to make a drastic change if I was ever going to get my life back and enjoy working for myself again.

I hope, for your sake, your line in the sand doesn’t have to be $100,000 in debt, being 50 pounds overweight, or feeling like your life is completely out of your control. I hope you’ve made the realization that your business model is broken or that you’re running a business that you don’t truly believe in any longer.

You don’t need to know what to do next to make a difficult decision.

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, you’ll 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 didn’t have a next step. I didn’t have another business idea. But I had built something. For five years I’d 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 I’d done during that time was wasted effort, and I could use the lessons I’d 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:

“Jason, what do people ask you about the most? Would could you teach from your years of experience?”

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 I’d 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, “Jason, please call me and let’s chat.” (I’m sure there was much more said, but that’s what stuck in my mind.)

Now, it’s worth mentioning, because I want to let you know it’s okay if you don’t ask for help right away. It took 8 months for me to gather the courage to call Pam. I’m 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 didn’t 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 who’s written a book you’ve read. They may be some sort of business coach you’ve heard about. Heck, they could simply be a family member who’s had business experience.

The important thing is that you talk to someone and don’t try to figure everything out on your own.

Another tip here: Read the book The Obstacle is the Way. I wrote an article entirely about this book as I think it’s the most important book I’ve ever read. I highly highly HIGHLY recommend that book!

Only you can decide to quit your business

It’s 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 I’ve ever made.

Looking back, it’s 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 wouldn’t 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 learned so much about how to NOT run a business. But more importantly, I learned how to measure success through internal validation first.

I continue to learn lessons every day from those five years. I know they’ll 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 there’s a tough decision you need to make about a business that’s no longer serving you.


Thanks to Caleb Campbell for asking me to write this article originally for Why I Stopped.

Celebrating Our Beautiful Failures In Business

January 30, 2017

In business and in life, we talk a lot about the topic of “failure.”

The fear of failing keeps so many of us from taking risks (or trying anything at all) and it’s responsible for keeping people stuck in jobs they don’t like or businesses that aren’t working.

In response to this, a new conversation around failure has been forming in the entrepreneurial ecosystem, one that says: “If you’re not failing, you’re not trying something different…” or “Failure teaches us more than success ever will…” or “Fail forward.”

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 showing you their failures? Not just brushing them under the rug but REALLY shining a light on them and celebrating them?

I know I’m guilty of this. I can write newsletters about experimentation or my processes for making tough decisions in my business, but I admit there’s a part of me that always tries to spin these moves in such a way that avoids calling them what they really are: failures.

Honest question: did your heart sink just a bit when you read that word… “FAILURE.” It has quite a specter to it, doesn’t it? It feels almost taboo when you’re 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 isn’t just talk. I want to gloriously and openly share with you all the experiments I undertake in my business that DON’T 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, let’s talk about my most beautiful failure to date: Color Your Soul.

If you’re a member, you’ve already been alerted to this, but for those of you who don’t know yet, unfortunately I’ve come to the decision that January’s issue of Color Your Soul will be its last.

I can’t 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.

The Time Cost

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 can’t 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 week’s email, and this is definitely a case where the time efficiencies of the product itself really hurt the product’s viability.

Fragmenting My Attention

The original vision for Color Your Soul, aside from being a soulful answer to all the strictly business related resources out there, 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, I’ve 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 I’m 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 I’m 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.

I’ve always said that there’s 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.

Taking my own creative business medicine

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 week’s newsletter and being reinvigorated by the concepts in the Make Money Making workshop, I’ve realized that I need to take my own medicine. I need to let go of what’s 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 week’s process was this: Start by acting on your Big Brick Wall and your Big Cracked Door. As much as I didn’t 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 that’s either to try and improve what’s not working or to simply let it go. In this case, letting it go is the right (but hard) choice.

Living the Made Vibrant ethos

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 now… it’s not a pretty sight!)

If I’m honest with myself, these past few months 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, as much as you WANT to sell what is true over what is easy, you also have to accept the reality of what you’re sacrificing to bring that idea to life, and for me, it’s just too much.

What I learned

Though every business and every person is different, there are a few practical lessons I learned from this experiment and I’d 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. That’s 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 that’s great, but in practice it feels incredibly restraining. In the future, I’ll go back to embracing ideas with a more flexible structure so I can uphold that value of flexibility.

Selling (and explaining) something that hasn’t been sold before is not easy. If the product itself didn’t 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.

What I hope you’ll take away from this

You’ve heard me talk about this in theoretical terms before but right now you are seeing it play out. We have ideas and they don’t always work out the way we envision them. That is OKAY — Experiment anyway. Experience anyway. And check back in with yourself often so you can learn firsthand what lights you up and what drains you.

“Our ideas don’t always work out the way we envision them. That is OKAY. Experiment anyway. ”

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 wouldn’t go back. I have learned a lot these past few months about what brings me joy and what doesn’t, what people are willing to pay for and what they’re 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: We won’t 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 — and I keep sharing these pursuits with you all honestly because I want to inspire you to do the same.

I’ve 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 didn’t work. Now.. onto the next.

Behind the Scenes of Building a Product in 1 Day: Emojibombs

June 6, 2016

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 “Rat People” after this article). I told Paul I couldn’t stop thinking about these emoji stories and that we should make it happen. He said he was also thinking about them.

Emojibombs Slack Conversation

The longer we chatted in Slack to more decisions we made:

  • We’d call the daily emails “Emojibombs”
  • We’d build the product of Emojibombs in 1 day
  • We’d let the Internet watch us do it and submit their own emoji origin stories
  • It would be cheap to buy
  • It would be a fun idea, something super silly

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, let’s 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 I’ll have in all of 2016 (no joke). Nonetheless, we picked a date and committed to it.

Our plan of attack to build Emojibombs in just 1 day

  • We’d set up a kick-off Crowdcast (live video event) for June 1 at 9am* PDT
  • Paul would include a mention to the Crowdcast in his May 29 Sunday Dispatches (his weekly newsletter)
  • I would include a mention to the Crowdcast in my May 30 Action Army newsletter
  • We’d share the link to the Crowdcast on both of our Twitter accounts
  • Everything** would be done live on June 1***!

*: Paul and I both wake up fairly early. When I woke up at 6am on June 1, I’d already received a message from Paul saying he wished we’d 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. We’ll start earlier the next time we do this. Hah.

**: “Everything” 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. We’d created plenty of things in the past, but building anything in one day presents a ton of challenges. I’d 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.

Sunday Dispatches and Action Army

After our emails went out to our lists, we had 335 people registered for the live event. We pitched it as a “mysterious” and “silly” event.

Setting up Crowdcast for Emojibombs

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…

DJ Waldow Text

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. We’ve done at least 10 Crowdcasts together, and I’ve 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 couldn’t see Paul’s video. Then I could see him, but I couldn’t hear him. Then he could see me, but he couldn’t hear. It was a terrible game of “who’s on first,” but some of the time you couldn’t hear/see the other person. Luckily one of the founders from Crowdcast was in the chat and quickly jumped in to help us out. I’m 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:

Crowdcast for Emojibombs

Another quick aside: I share the technical hiccup here, not to criticize Crowdcast. I’m actually a very happy paying customer of Crowdcast (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, it’s 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 “mysterious” and “silly” emoji-related project would be. I remember a few things happened right as we explained what Emojibombs would become:

  • About 30-40 people immediately left the Crowdcast (to be expected, some people hate emojis – weird, I know!)
  • About 10-20 people had no clue what we were talking about
  • A handful of people wanted to pay us money right then and there
  • A handful of people had lots of idea for how we should do things, what we should charge, and other feedback that would derail us

It’s an interesting thing to announce a project to a group of people and then say you’re 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 we’d 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 “I don’t like this idea.” But, as Paul and I have both learned over the years, seeing those people leave is a good thing. They weren’t interested in Emojibombs and we’d 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.

As we wrapped up the Crowdcast, we wrote down a list of the immediate next steps:

  1. Paul would install his Nada WordPress theme on Emojibombs so we could start writing updates on a 1-page blog for people to read.
  2. Paul would put an email capture somewhere on Emojibombs so folks could get updates emailed to them throughout the day.
  3. Paul would work on the branding and logo.
  4. Paul would create the initial automation sequences and subscriber groups in Mailchimp.
  5. I would setup the Stripe account so we could accept money from people who thought Emojibombs would be fun to get each day. (We decided on a price point of $11.)
  6. I would start organizing all the screenshots and conversations we were having so we could share updates throughout the day.
  7. I would try to keep us on some semblance of a schedule (11am for the next email, 1pm for launch. Both deadlines we failed to make… haha).

Paul and I have worked on a bunch of projects together now. We’re 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 we’ve 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 can’t imagine trying to do this project, or any other project we work on together, without Slack.

Within the first hour, we were off to the races…

Mailchimp had been setup. Stripe had been activated. People were sitting on the website refreshing incessantly.

Mailchimp Groups for Emojibombs

Emojibombs Stripe Account

Gosquared for Emojibombs

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).

Slack promo

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:

Jason Zook Heart Rate Fitbit Charge

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 didn’t believe him (and since he couldn’t send me a photo of proof, we’ll 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.

< Insert Building a Product in 1 Day Project Drama >

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…

Mailchimp Compliance Jail


Now, why is this such a big deal? Well, if I haven’t cleared explained it, Emojibombs is completely driven by email. It’s a daily emoji origin story sent to someone’s inbox. Mailchimp is the company that would be handling that sending for us. If Mailchimp flagged our account for something and we couldn’t 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 didn’t understand why we were being flagged for compliance. We did have a few thoughts as to why it might have happened:

  1. The speed at which he created an account, made a list, made groups, created an automation, designed an email template, and imported our 350+ Crowdcast attendees emails could look robotic (because speed = robots).
  2. We were using the word “bombs.” (Paul didn’t think this was actually a problem and while I agreed with him, a small part of me was skeptical).

Before I share whether we got out of Mailchimp Jail or not, I’ll 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 freakin’ 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 didn’t 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 you aren’t familiar with them, ConvertKit is actually the email marketing provider I switched to earlier this year (from Mailchimp). I’m a very happy ConvertKit customer and the only reason we didn’t 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 didn’t release us from their compliance clutches.

And then we got an email…

Mailchimp Jail Escape

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 hadn’t 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:

Emojibombs Homepage Mockup

Emojibombs Mailchimp 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, I’m excited to get these Emojibombs too!

Emojibombs Stripe Purchase

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 people’s emoji stories, and it’s nice to be able to give another one of our products some exposure while we have people’s attention.

Emojibombs on ofCourseBooks

ofCourseBooks for Emojibombs

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 idea…)

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 we’re 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 you’re interested in hearing about all the stuff we were working on in that moment.

And another aside: When it comes to any project, it’s important to set milestones and time constraints. You don’t have to go crazy, but we’ve found that if you don’t put limitations on things, they can tend to drag on and on. On the flip side, when you set milestones and don’t hit them, you have to understand that the majority of milestones are completely arbitrary and made up. You don’t 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:

  • Paul was working on the website (design and code)
  • I was (finally) writing the first update email to our list of 350ish people
  • I was editing our video updates
  • We were both tweeting (which doesn’t sound like much, but takes time)
  • I was monitoring the emoji story submissions through ofCourseBooks
  • I wrote copy for the Emojibombs about page
  • I created a Google Doc where we’d keep/organize the actual daily Emojibombs
  • We both needed to take a break to eat some food and keep our sanity
  • We set a new launch time to 3:30pm

Paul being a level 12 wizard

Emojibombs About Page

Emojibombs Google Doc


After we returned from our short break (probably 15 minutes), Paul sent me a message and told me he’d “made it rain emojis!”

It was at this moment I did a little happy dance. The idea for Emojibombs didn’t 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.

From there, we had a bunch of loose ends to tie up.

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 “social intent” 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!

Emojibombs Social Intent

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 don’t 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.

Mailchimp Automations

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 “Hrm… how do I make this live?” I started to type a response, nothing that would have actually been helpful (because I’m not a Level 12 wizard like Paul). And then before I could send my message, he wrote back “I got it!” 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!

Emojibombs Homepage

Hitting SEND on our first sales email to all the folks who subscribed today: I wrote our “sales” 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.

Mailchimp Sales Email

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). Here’s 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!

Around 5pm we had completed and launched Emojibombs!

After a solid 8 hours of work, we had a living, breathing, purchasable product that didn’t 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.

Let’s take a look at the numbers since launch day (now about 5 days after)

Total traffic to Emojibombs:

  • On June 1, the day we built it: 1,345 visitors
  • June 1 – June 5: 3,295 total visitors
  • 47% of traffic has come from direct sources (our emails and people typing the domain)
  • 28% of traffic has come from social media (85% of that is Twitter)
  • 23% of traffic has come from other websites (Product Hunt and Designer News being the highest referrers)
  • 1 single person came from, which I just find funny and random

Gosquared Emojibombs To Date

Here are our running expenses:

  • Fonts $93.10 (classic Paul, spending the majority of our money on fonts!)
  • MC4WP plugin $49.00
  • MailChimp $9.00 (this will be monthly)
  • Hover for the domain $13.83
  • Digital Ocean for hosting $50.00 (this will last us 5 months)
  • Total: $214.93

And our total sales numbers to date:

  • 25 paying customers
  • $217.98 revenue (after Stripe fees)

Total profit: $3.05 (we’re profitable!!!)

Now, final thoughts to wrap things up…

Doing a 1-day project is stressful. But truthfully, it’s 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. That’s extremely powerful. Sure, we’ve 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. There’s no telling what the long-term positive affect might be for our future projects based on what we did with Emojibombs. And that’s very intriguing.

I want to touch on the fact that a 1-day project is a great promotion tool. Not only for the project you’re creating, that’s obvious, but also for all your other projects. Doing this project reminded me of the quote:

“A rising tide lifts all boats.”

And it’s 100% true. Emojibombs was the tide that gave us a platform to promote ourselves, but also our other project (boat) ofCourseBooks. Sure, it’s 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. It’s not going to solve a huge problem that creative professionals and freelancers have. But it is a slice of fun sent to people’s inboxes every day. It’s a message of weirdness and hilarity amongst all the to-dos, tasks, and customer service issues that tend to plague our email inboxes. We’re 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.

I’m not sure what our next 1-day project will be, but we’ll definitely be doing this again. I hope you’ve enjoyed seeing behind all the curtains with Emojibombs. Now excuse me while I go write some silly emoji origin stories.

Understand That Quitting Isn’t Failing

October 18, 2015

Does your workday spiral out of control from the moment you wake up? Is there a relationship in your life that feels toxic? Are you feeling overwhelmed?

You might not want to hear this, but it’s time to quit.

There’s a lot of advice out there saying “Don’t give up!” and “Push through the tough times!” 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?

Just because you quit something doesn’t mean you’ve failed.

The added time and freedom you’ll feel from quitting are well worth the struggle of making the call to let go and move on.

Whether it’s a short-term quit or a long-term quit, it’s time to take control. It’s time for you to take the necessary steps to get yourself out of situations that aren’t bringing you value.

Making temporary space through short-term quitting

When it comes to freeing up your time you don’t 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 break—one that can help you figure out if you want to quit completely or continue on.

Let’s talk about quitting social media

In 2014 I got really frustrated with social media. I wasn’t seeing the interaction that I’d seen in years prior and felt myself getting angry when reading tweets and posts from people about topics I didn’t 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 wasn’t 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 wasn’t 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 I’d like to admit staring at a completely blank page in my web browser, all the while thinking “where do I go on the Internet now?”

The life-altering power of a social media detox

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 not 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.

The power of long-term quitting

There are times when a short-term break just won’t 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).

Quitting something that has momentum

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 you’re thinking “why the heck would they do that, this sounds like a great idea!” 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 didn’t 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 I’d 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.

There’s a lot more context and layers of conversations to share, but it was apparent to me that I needed to quit 1MillionShirts. It wasn’t just that I, personally, needed to walk away. It’s that I needed to shut it down (especially since over 12,000 t-shirts were donated within the first few weeks).

Confusion and quitting will often hold hands

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.

Quitting is essential to starting

Removing yourself from the quitting = failure mindset shows you just how much more can be accomplished when you free up time in your life.

Letting go of something puts you in control. If a project or relationship isn’t bringing you value and isn’t working the way you want, quit it.

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 don’t have to quit big things either. If you’re trying to get healthier, start doing yoga. If you hate it, quit it and try something else. If you’re 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.

Quitting shouldn’t be looked at as the end

It’s 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 can’t control, while quitting means you’re taking control of the situation.

Think of all the successful people you look up to right now. I doubt you can name anything they’ve quit. People don’t 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.

The First Helpful Thing Failure Teaches Us

September 29, 2015

I’m going to let you in on a few secrets this week.

These are stats and stories that I’ve 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 “failure teaches us lessons that lead to success” song and dance.

That is until now.

As you may well know by now, last week I was busy devouring page after page of (my spirit animal) Elizabeth Gilbert’s latest treasure, 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. It’s part mystical and intriguing, part practical and actionable.

In the book, Liz shares a quote about failure that stopped me dead in my tracks:

“Failure has a function. It asks you whether you really want to go on making things.”
– 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 “worst-case scenario” of sorts so that we can honestly ask ourselves: 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.

In the spirit of that context, I want to share with you a failure of mine.

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.

That’s when the idea for Connecting With Your Core 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 wasn’t 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:



17 people purchased the book for a total of $392 made.

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 I’m never going to write another book again, I’m never going to sell another product again?

Heck no. Why?

Because that was a book I HAD to write.

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. It’s still one of the things I’m most proud of that I’ve ever created, so much so that I spent even more time re-vamping it and hand-illustrating it for the latest shop launch.

(I’d 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 “failure” of my first product asked me that all important question: 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 that’s why I hope you create to. Because you have to. Because even the possibility of failure can’t 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.

So my challenge to you this week is just that:

What is one thing you would feel compelled to do even if you knew you were going to fail? Even if you knew it wouldn’t bring you money or sales or success, what would you need to go on creating?

Now what’s one promise you can make to yourself in order to do more of THAT.

On Wednesday I’m flying to Brookings, South Dakota because Jason and I have each been invited to present a TEDx talk. I’ve 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 “right” or not doesn’t really matter. Because even if I were to fail, even if not a single person in that theatre felt moved or touched, it’s 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:

Failure is a gift. It’s how you know you can go on creating from a place of joy and not a place of recognition.

“Failure is a gift. It’s how you know you can go on creating from a place of joy and not a place of recognition.”

View it as a tool to get you closer to the work that will light you up to your core.

Thanks as always for reading, and I’m wishing you a fantastic week!

I Failed P90x and Here’s What You Can Learn From My Experience

November 17, 2014

A few years ago I spent about $150 on the entire P90x DVD set. This included all the DVDs, nutrition guide, the official protein powder and a set of workout resistance bands. The late night informercials finally convinced me 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 amazing shape and become a much healthier person.

I only made it to P33x.

For those of you who might not be familiar with P90x, it’s a set of workout videos and a nutrition plan all guided by this ridiculously in-shape personal trainer named Tony Horton. You may notice the “90″ in the name, and that’s because it’s supposed to get you ripped and in “beach body shape,” in just 90 days.


The P90x workout schedule isn’t for everyone

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 the end of the warmup I was drenched in sweat and I felt like my heart was going to explode (not a good sign).

I 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 was not.

I will give credit to Tony Horton. Throughout every single workout video, he tells you to “do your best and forget the rest.” He shows you exercises you can do if you can’t do pull-ups, push-ups, whatever. It seems like he tries 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 did my “best” and tried my hardest to “forgot the rest.”

Only, my best never got to be good enough. And during every single punishing minute of every workout all I could think about was the rest.

I spent 33 days trying my hardest to keep up with Tony and the other people in his workout videos, only to feel like I wasn’t good enough every single day. After that 33rd day, I finally gave up. It was after the stupid “Ab Ripper X” workout. I remember it like it was yesterday. I stopped mid “Crunchy Frog,” turned off my TV, tossed my 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’re just getting started and you feel completely overwhelmed or you’re an existing business and you feel like you’re stuck climbing never-ending uphill battles.

We all need to work at our own pace and that may not be the P90x schedule.

One thing that always killed me with P90x was that I felt like I was constantly behind. I was never doing enough reps of an exercise. I had to take frequent breaks while Tony and his crew moved on to another exercise I could barely do. Eventually I skipped large portions of the workouts because I felt so defeated. I don’t think the pause 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? As soon as you dive in (P1X) you find yourself overwhelmed, intimidated and hating the experience. All you want to do is quit.

If you’re trying to model your business after a successful business in your space, it can feel impossible. If you’re just trying to keep your current business afloat with new approaches or strategies, it often feels like nothing is working.

This is the problem with trying to work at someone else’s pace, using someone else’s tips, tactics and whatnot. You need to understand who you are and in what environment you work the best. Just because something 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, 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 it can be done. Take the bits and pieces you like, if any, and apply them to your own work. You definitely don’t want 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 time consuming) workouts and still see results. The process of starting P90x, while not my favorite experience ever, did lead me to successfully getting back in shape in my own way and at my own pace.


You won’t always hit a home run

I’m not even a baseball fan, but I completely understand the sport, and I know players won’t always hit home runs (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, sometimes they even bunt the ball. Triples, doubles, singles, and bunts are perfectly acceptable outcomes when 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 last dying breath, it felt like I was watching a bunch of home run hitters. No one struggled like me. I simply couldn’t 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 next marketing strategy is strike out.

Yes, you might swing and miss on a few things here and there, but you should be able to learn from your mistakes without moving so quickly in the process that you’re bound to repeat them.

Timelines will change and that’s okay.

I completely understand the structure of P90x and how it works. The problem is that not everyone is wired like 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 would be realistic for me and I gave up. In business, it’s easy to set goals and milestones, but it’s nearly impossible to hit them perfectly. There will ALWAYS be things that come up and delay the process. Knowing this ahead of time and not handcuffing yourself to these things will keep you sane and able to deal with adversity when (not if) it comes.

I also never felt like I was celebrating the small victories in P90x. I only ever felt behind. With your business, you should appreciate and enjoy the small successes that come your way. You should embrace the journey to reach your bigger goals and not loathe every single sweaty moment of the process.

Taking some action is better than taking no action.

Doing P90x led me to creating my own workout and nutrition plan that worked for me.

Had I not made the commitment to at least try P90x, I never would have given up at it and tried something else.

I guess I do have to 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 those thoughts and feelings. To understand that they exist in our minds and to push past them and at least do something.

Whether you’re just getting started or have a huge plan of attack, the best thing to do is start. From there you can analyze and adjust as you go. You will make mistakes, hit bumps in the road and eventually start to see success.

Fear Doesn’t Have to Paralyze You

June 17, 2014

The crazy thing about fear is that we aren’t born with it.

If there’s one thing I’ve learned about myself over the years, it’s that I’m not afraid to put myself and my ideas out there. For some of you reading this, you’re the complete opposite (and that’s okay!).

Fear is something we learn over time. Whether it’s from the people around us or the circumstances we live in. However, fear is also something we can overcome with effort.


I want to share a quick story with you about overcoming fear…

When I graduated college I was getting ready to find my first “real” job as a graphic designer. I’d 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 didn’t contain any sports-related work. I didn’t 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 “what if” 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 couldn’t 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 wouldn’t pretend to be something I wasn’t. 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 didn’t 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 I’d 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 couldn’t. 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 couldn’t name tennis players, they couldn’t 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 “what’s the worst thing that will happen if I do this?” More often than not, there is no “worst thing.” There’s no outcome that I can’t survive.
Whatever the thing is that you’re afraid of doing right now just ask yourself:

What’s the worst thing that will happen if I do this?

I’m willing to bet if you answer that question honestly and really drill down, the fear you have won’t 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.