From GQ Design Director To Free Agent

I’ve become the pre-imminent poster boy for the world’s worst career strategy, which some may call voluntary self-demotion. At the height of my managerial career, I was leading a team of 21 across multiple publications and was likely one of the highest earning editorial creative directors in the industry. Years into this role, I was tapped to be GQ’s design director. This not only meant accepting a lower title that would absolve my oversight of the photography department, but also taking a nearly six figure pay cut, and reducing my team to three. What drove my decision was not money or authority—it was a desire for a new challenge and a deep personal interest in the subject matter, fashion, which wasn’t the case before. This job felt more aligned with what I seek and who I am.

The job was almost everything I could have wanted. I was thrilled to be surrounded by brilliant people across every department. I hand picked a small but formidable team, and amid the chaos of logistical challenges and rapidly evolving corporate initiatives, we created a safe space to experiment and explore ideas freely. We made work we were proud of, we won awards (meaningless, but good for morale), and most importantly, we had fun.

I learned to appreciate being a manager, specifically when it came to the bonds you form with your team, but it also required far less idyllic responsibilities: endless slacks, meetings, and emails, not involving the creative work itself but everything concerning the planning, production, and the multitude of mundane processes around it. Being a manager also means that you adopt everyone else’s needs and priorities as your own. You must be willing to spend countless hours supporting a team member if necessary. With any achievements, credit should be given wholeheartedly, and any missteps, responsibility taken immediately. Then there’s talent retention in an industry with limited upward mobility. As soon as a team starts running like a well oiled machine, a better opportunity elsewhere can appear. I’ve always felt genuine pride when someone moves their career forward, but the frustration is also undeniable, and the cycle gets repetitive.

The strongest motive behind my second self-demotion, when I left the aforementioned job, was ultimately very personal. It was the feeling that I wasn’t creating enough, and therefore, also not reaching my full creative potential. I made time for it where I could, mostly off-hours. I would spend Saturdays and Sundays gleeful to not hear the anxiety-inducing knock-knock of a slack alert every few minutes, and my life was temporarily distilled to just listening to music and drawing. For better or worse, I’m wired so that being obligated to reply to one inconsequential email will drain my will to live, while spending 12 uninterrupted hours on an illustration will have the opposite effect. The meaning and fulfillment those weekends held was telling to a point I could no longer ignore.

Quitting without a back-up plan was one of the most terrifying things I have ever done. The night before my public announcement, the gravity of what was about to happen hit me, and I spontaneously started sobbing into the arms of someone I had recently started seeing. I spent years living alone in a spacious two bedroom, spending my disposable income on art and furniture to make it the home I had dreamed of. Knowing my steady pay checks would evaporate, I had a choice. I could either make a significant downgrade or get a roommate. I decided to stay and meticulously rearranged my apartment so that I could live almost entirely out of one bedroom, including placing my mattress in a storage area above my desk. Then I put out a listing, nervously hoping for a kind stranger to materialize.

There were many other ways my life would change, such as when a Raya date admitted she went out with me because of my job title. This decision was also a final act of defiance against what my family raised me to worship, namely money. I grew up in a lower income household, a child of Latino immigrants who landed in Brooklyn with a few hundred dollars, minimal education, and no ability to speak English. My sister went to medical school, so choosing art school crushed them to say the least. Before my dad accepted that I wasn’t going to change my mind, he ridiculed me ruthlessly for it. Now I was leaving a rare, lucrative position to prioritize something that would make his brain combust: to have more time to draw stuff. I spared him many of the details, and for the sake of our tenuous relationship, he’ll never know the full story.

You, like my dad, may be thinking I’ve made a terrible mistake. You may be wondering what the deeper impetus behind “less slacks and more drawing” actually is to make such a dramatic change. It may be a little surprising that it’s only been a few years since I’ve fully accepted myself as a creative. Despite a not insignificant amount of therapy, I’ve carried shame around this career since I started. Even when my lifestyle became more excessive than I could have imagined—spending on everything from a $6,000 Saint Laurent jacket to Michelin-starred tasting menus to traveling the world and only getting around in black cars—I never talked about work with a sense of pride outside the office. I would brush it off as something frivolous, meaningless, unnecessary. “I’m not saving lives,” would be my response to shut down anyone that was impressed.

I eventually sought out volunteer work to feel less worthless, showing up at the Red Cross and being disillusioned after getting assigned the only task I could do with my limited skill set: installing smoke detectors in the apartments of people who gave every indication they didn’t want us there.

My breaking point began after the pandemic, when I experienced the painful losses of a failed long term relationship and close friends who fled the city. The subsequent solitude caused an acceleration of the lifelong process of figuring out and accepting who I am.

I arrived at a conclusion that was always right in front of me but that I hesitated to fully embrace: I fucking love to make shit. When I make something I think is good, it fulfills me. Spending more time making shit means it’s likelier that I’ll make things I think are good. If it matters to me and no one else, if it connects me to a mysterious intangible force in a way nothing else can replicate, it makes it important. Protecting and nurturing something that is important to me is worth the hardship it may require.

Just fourteen months into my new life as a freelancer during the worst economy for creatives in generations, there is the question of whether the risk was worth it. The answer isn’t simple. Financially, I’ve earned a little more than what I made my first year out of college (if you’ve seen the social content from some indulgent dinners, know that I still live somewhat recklessly off my previous earnings). I still have a roommate, and she’s the best. My strengthened sense of self has brought me closer to old friends that have stayed, and brought new people into my life who I love and that inspire me.

Occasionally, an amazing person will agree to date me despite my lack of a bed frame or any clout to speak of. Above all, I no longer spend a majority of my life doing every creative task other than actually creating. Now I just make shit. I remain in wildly unpredictable territory. I still have no idea whether this is sustainable. In time, I may begin to crave the security and camaraderie of a corporate environment again, or I’ll be taking orders at your local coffee shop (don’t forget to tip). There is one thing that’s irrefutable: this challenge, with all its extreme highs and lows, this choice I had the privilege of making, is the most committed step I’ve taken toward being the most true to who I am. In this precious, fleeting life, it’s an extraordinary feeling.