For those of you not really interested in my path from in-house designer to self-employed creative director, I should warn you: this is a pretty lengthy prologue that has little to do with the apprenticeship program itself. For the rest of you: buckle up.

Breaking into brand design

In 2019, I began casually looking around at job openings despite having a comfortable senior design position at one of the coolest companies on the planet. I made it really far in the interview process for an equally cool company, and even though I didn't get the job it helped confirm that I was ready for something new.

<aside> 🎯 The job I didn't get was at Target HQ. I don't mind sharing, because of how validating it was to be that close. Actually, when I told my wife that I wanted to be a designer (mid-2014?), she asked what companies I would consider working for and without hesitation I said ESPN and Target. To be considered by one of these organizations, and hired by the other, still makes me extremely proud.

</aside>

Truthfully, I was crushed when I didn't receive the "we'd like to hire you" phone call I'd been expecting. I was extremely confident and it took my by surprise. I carried my frustration to work and it showed. Within a few days of the news, I yelled at a colleague in front of the entire department. The next morning, I was privately reprimanded and asked to take Emotional Intelligence training. Was my immaturity a sign that I wasn't as good a hire as I thought? Clearly I had some growing up to do, but I wasn't sure what the plan was after that.

I'd gone from being happy at work to feeling unfulfilled and imagining life in other places. I started applying for jobs wherever I saw a "we're hiring" sign and ended up going on some pretty ridiculous interviews. After a few obvious mismatches, I decided to hone in my search and look for a job at a branding studio, or somewhere I could learn more about identity design.

To this point, I'd only ever done logos for friends or small businesses without much strategy (or budget). I think my work shows a natural progression from those early freelance projects to the more recent ones, but I was convinced what I'd picked up from friends, online tutorials and conferences would be dwarfed by the collective knowledge at an in-house agency. After all, before I got to ESPN I didn't know much about code, editorial illustration or web design. Branding would be much easier to pick up if I was surrounded by people that did it 24/7 — right? Right???

The thought was logical, but impractical. I just couldn't get my foot too far in the door anywhere. I interviewed at small shops, big agencies and everything in-between. More than once I was told, "You're a little too senior for what we're looking for," which made me feel old and lagging behind. I would think to myself, I wish they'd just give me a chance. I'd work for way less than I make now. I'll never get anywhere without the experience. Not wanting to seem desperate, I would always respond with, "I understand," and talks would awkwardly end.

<aside> 🙄 Employers: if someone seems "too senior" then don't bring them in for an interview. Or better yet, state your suspicion in an email and ask the candidate about their situation. I might be a rare case, but just because I'd been working in-house for five years didn't mean I was looking for a step up or expecting a competitive salary. This was always so frustrating for me and wasted time for all parties involved.

</aside>

The most exciting prospects all fizzled out and I ended up taking a senior level design position at an advertising agency in Kansas City. The location was the biggest driving factor and I jumped at the chance to move home, even if it didn't seem like the perfect fit (it definitely wasn't).

<aside> 😥 One of those exciting prospects verbally committed to hiring me and the owner shook my hand as if it were a done deal. I knew to be hesitant, but was crushed when the job eventually disappeared. Looking back, had I been hired and moved for that job, COVID likely would have taken it away. It turned out to be a blessing and I'm so grateful the way everything has worked out for me and my family since leaving ESPN.

</aside>

Finding the courage to quit

I was grateful to have a job and the pandemic put a lot of things into perspective for me. As long as I could take on the occasional freelance client and pick up some brand strategy, copywriting or general marketing tips from my in-house gig, I figured it would all be worth it in the end. While working from home for the ad agency, I realized there were several hours a day I was just waiting on feedback. I decided to fill those pockets of time with video calls to other designers — half branding and identity specialists I admired (but hadn't met), and half friends who I hadn't seen since our regular conferences and scheduled meetups had been canceled. I averaged around 4 calls a week and for the entire duration of my time in advertising (~6 months) they were the highlights of my day. They also ended up being the motivating factor in my decision to strike out on my own.

<aside> 📆 I still have regular meetings with some of those people who were so influential to my decision. There are plenty I need to catch up with, but even just causal check-ins via email or DM have become extremely helpful. I definitely recommend hitting up your favorite designers — whether you're already buddies or not — and asking for their time. Most are generous enough to schedule something, just remember to be patient and have an attitude of giving. You might be surprised who's available (and what it will do for you).

</aside>

I probably should have seen it coming. Between my interests shifting from editorial to branding and those smaller brand studios balking at my candidacy*, it feels obvious now. Maybe, subconsciously, I'd just been delaying the inevitable. I definitely lacked courage before connecting with my peers, but I like to think that deep down I knew it would happen all along

<aside> *️⃣ I prolly harp on studios not being willing to hire me a little too much in this article. But I get it: asking someone to relocate and commit to a role that's objectively lower than their current position is quite a risk (for both parties). I still admire and respect the studios that passed on me and would jump at the chance to contract for them now.

</aside>

More to come

Thanks for sticking with me. This was a longer entry, but provides helpful context. Stay tuned for insight on starting the program and my takeaways from interviewing, hiring and managing designer(s) as apprentices. I'm hopeful this series breaks things down in a helpful way so others feel empowered to start similar programs and/or make time to mentor designers. It's a pretty heavy commitment, but extremely beneficial.


If you have more specific questions about the apprenticeship program, you can email me or leave a comment (if you're a Notion user).