The Truth About Working for Myself


I’m getting REAL real about what my life has looked like since I became my own boss.


This isn’t one of those articles that’s gonna tell you how to make $200K a year or how to bag the biggest clients.

I’m not going to try to convince you that working for yourself is the only path to true freedom, or that going it alone is a superior choice to working for someone else’s company. I’m not going to tell you I’m making more than I ever have before, or that my life’s trajectory is all-so-clear to me now.

Because none of that would be true.

Instead, I want to share my super honest experience of what working for myself has actually been like—the good and the bad—in hopes that it will resonate with those of you who are either in a similar spot, or who are considering starting your own business but aren’t sure if you want to take that step.

Plus, the interwebs could use a little dose of authenticity, don’t you think?


In 2017, I left my job as an art director at a small advertising agency to develop a paper goods business. I didn’t leave because I was making bank off selling art prints or anything. In fact, I was making maybe $2K a year on Etsy off the few products I had already created.

I left because I was not feeling fully fulfilled, and I was ready to take a bit of a calculated risk in the hopes it would push my life in the right direction. I had been planning and researching and saving up for years, and I had backup plans for my backup plans. I had an actual 37-page business plan that was color-coded and 3-hole-punched in a binder. Does this give you some insight into the kind of person that I am?

The carefully outlined plan gave me a month and a half to design and produce a full collection of art prints and greeting cards, and anything else I decided to make after running it through my 45-point system for determining what products would be the most viable. I’m serious. Somebody help me.

And I did it, just like the plan told me to. I created the collection of designs (they were more pattern and illustration focused at this point, as I hadn’t fully realized my love for lettering). I created the packaging, I made my own online shop, I followed all the steps to market my new business. And then I launched it all into the world!


Well, it wasn’t a total flop. Many supportive friends and family members, and a few friends of friends, bought some stuff. But I had read how Anna Bond and her husband launched Rifle Paper Co. and immediately got so much traffic that their website crashed, and I think I secretly hoped some internet fairy would shepherd folks in my direction and I’d be an overnight sensation.

But not to worry. The logical part of my brain had prepared for this, and had already baked it into the plan. There were additional phases to complete, like preparing my wholesale catalog and continuing my marketing efforts, as well as applying to craft fairs. I tried to push my disappointment down, and I kept on keeping on.

I created a very professional wholesale catalog and line sheet that I was really proud of and started sending it out to shops in hopes they’d stock my prints and cards. I found some stockists who wanted to carry my work and was encouraged by their interest. However, wholesale is incredibly time consuming, and searching for shops and contact info and personalizing every email is super draining and simply not what I wanted to be doing with my time all day every day. So, slowly, the major wholesale outreach died down.

In the meantime, I was getting into the craft fair circuit. I designed my own booth and learned how to stuff it all into my Honda Civic and load it into venues in the pouring rain. I learned what shows I did well at, and I learned what shows were flops for me (I literally made -$35 at one tiny craft fair that was 4 hours in unshaded 100 degree weather…because the booth fee was $25, and I bought a $10 tie-die cat shirt from the vendor across the aisle).

I received a few grunt-work freelance requests during all of this, which I took, because money. But it was tough going back to doing some of the work I had resented at previous jobs. It wasn’t stimulating, and I was frustrated at myself for being in a position financially where I felt like I couldn’t say no.

I was frustrated in general.

I hadn’t found a clear direction or rhythm for my business yet, and I wasn’t confident I would. I was trying to stuff my feels down…way down…and distract myself by moving from task to task. I didn’t want to stop and really evaluate where I was at, because I was too afraid of feeling afraid.

Around this time, I got engaged to the absolute most wonderful Canadian (who, by the way, has been supporting the crap out of me and my business since the beginning). We planned a really small, simple wedding on the shores of a lake in Banff National Park in Alberta. I had (and have!) all the love for him and just wanted to celebrate and frolic in the majestic landscape of Banff without a care in the world!

But, apparently, my brain had some different ideas about how much frolicking I’d be able to do.

The night of my bachelorette party (which was very chill, by the way…I had like 2 drinks and a coffee) I was trying to sleep and woke up with numbness and tingling all over my arms that wouldn’t go away. I jolted upward and started to breathe heavily. I instantly knew something was incredibly wrong with my body. I rushed to the bathroom and threw water on my face…and then I fainted. My fiancee rushed me to the emergency room while I was shivering uncontrollably. I started forgetting the names of people closest to me and thought, with a good bit of certainty, that I was actually going to die.

After hours of tests, I got sent home with some potassium supplements. While my potassium was low, it was concluded later that I’d had a panic attack, which is something I’d only heard about on TV. It’s always thrown around so lightly in funny dialogue and moments of banter…I had no idea it would feel like YOU’RE 100% GOING TO DIE.

Thus began my awareness and journey with managing my anxiety and mental health.

I had put such an insane amount of pressure on myself—pressure not even a 3-ring binder filled with color-coded plans could alleviate. I hadn’t taken time to address my feelings and my fears as they came up, so they built into this huge and unmanageable thing. And on top of all that, I’d been unknowingly beating myself up in a way that was just so unhealthy.

When you work for yourself, you are doubly responsible for your successes or failures. You’re responsible as the boss who makes the orders, and you’re responsible as the employee who carries out the orders. That’s a lot of pressure. Think about it this way: If you’ve got a demanding jerk boss who expects nothing but perfection because his butt is on the line, as an employee, you’re gonna get real peeved real quick. And if you’re a peeved-off employee that’s grumbling under your breath and feeling unappreciated, your definitely not going feel motivated to perform your best. Let’s just say those are the makings for a pretty crappy work environment.


Immediately after my Anxiety Awakening (which sounds appropriately epic), I had a really tough time. My husband and I did get married at the lake in Banff, and our friends and family were there and it was beautiful, but I was also struggling a lot. When we got home from our honeymoon in the Canadian Rockies, I started going to therapy and have continued ever since. Slowly but surely, and definitely not in a perfectly straight, upward trajectory, I’ve been learning to be kinder and more understanding with myself, and more accepting of the uncertainty in life.

In the midst of navigating all of that craziness with my anxiety, I had still been trying to grow my business and find a clearer direction for my career. I was trying to post on Instagram almost daily and engage with the design community, and, in that process, I found HOMwork—a weekly Instagram lettering challenge run by Lauren Hom. I had always enjoyed dipping my toes into lettering, and had admired many letterers for years, but I thought it was an arena I wasn’t “qualified” to get into full time. Nevertheless, I decided to try the first HOMwork challenge when it was released, and then the next, and the next…and I got hooked.

Rediscovering lettering as something that was not only within my reach, but something I seemed to have a bit of a knack for, was really exciting. I felt reinvigorated, and my anxiety lessened a little bit with the discovery of this new focus. I started working on lettering every day. I created a new collection of greeting cards and art prints for my shop that were lettering-driven, and they were received in a much bigger way than the original launch. People started really responding to my work, and telling me how they could pick out my style and voice. I began to connect with other letterers online and at events like LetterWest, and felt I was really, finally starting to find my place.

I started taking on more interesting freelance projects and getting design requests from greeting card companies who had seen the cards I’d created for my own line. Working on those projects led me to the world of art licensing, which led to more work, and, eventually, acquiring a licensing agent! Now, I’m busy creating an e-course on licensing while preparing my portfolio for my first debut at the licensing trade show Blue Print.

I am in no way finished growing as an artist and a business owner, nor is my business fully settled and figured out. But I’m feeling a little more comfortable with the uncomfortable these days, which is really big. I’m feeling very lucky to be able get up and draw letters every day! And, with our recent move into our first house, I’m also enjoying getting to spend some time working on projects outside of work.

Getting to choose how your day, and your life, is set up is the ultimate perk of being your own boss, and it’s really worth fighting for if that’s something you want. While fear and anxiety will inevitably show up whenever you choose the unknown, facing those challenges will make you grow and learn about yourself in ways you never expected. Whether you choose to go solo or to work for someone else, do your best to push yourself toward the life you want and the things that make you happy, even when it’s hard!

I’m going to leave you with this, because it’s beautiful and eloquent, and really sums up the parts of this article that I hope you’ll take away…

Life shrinks or expands in proportion to one’s courage.
— Anais Nin
Katie Johnson5 Comments