Way Out #5: From Corporate Art Director to Watercolor Artist with Ken Stanek
Ken Stanek doesn’t have a "career path" in the traditional sense. He has a series of experiments, pivots, and intuitive leaps that eventually landed him exactly where he belongs.
From shivering as a bike messenger in NYC winters to designing PowerPoints for pharmaceutical giants, Ken spent two decades trying to fit his creative square peg into a corporate round hole. Today, he is a full-time artist, muralist, and illustrator who has finally stopped pretending.
But as he told me on the 101 Ways Out podcast, this wasn't a master plan. It was a process of "throwing pasta at the wall" to see what stuck.
Here is how Ken Stanek manifested his layoff, embraced the suck, and built a creative life from scratch.
Why Ken’s Story Stuck With Me
I first met Ken when we were both working at DIRECTV. To be honest, I was a little in awe of him.
It wasn't just because he was a genuinely cool guy who loved Lady Gaga (which immediately intrigued me). It was because of what he had done before I met him. He had quit his corporate job to ride a bike across the country, and then he came back.
At the time, that concept totally confused me. I didn't know you were allowed to pause the corporate treadmill. I didn't know you could choose adventure over security and simply return when you were done. I remember thinking, Wait, people can actually do that?
Ken was the first person who showed me that the "rules" of our career paths were actually just suggestions. He was already living with a sense of freedom that I was desperate to find. So when he finally left the corporate world for good to become an artist, I wasn't surprised. So it’s no surprise Ken was literally the first person I reached out to when I started doing my research for 101 Ways Out.
The "Safety Net" of Misery
Like many of us, Ken spent years in jobs that looked good on paper but felt wrong in practice. He worked in motion graphics, at Martha Stewart, and eventually at a pharmaceutical ad agency.
"It paid very well," Ken admits. "But I disliked it from the very beginning."
He describes the corporate experience as "sucking a lot out of his soul." He felt like he was wearing a mask every day, feigning enthusiasm for corporate designs and feeling terrible at faking it.
Knowing he wouldn’t last long, Ken didn’t quit immediately. Instead, he quietly prepared. He treated his time there as a runway, scrubbing his website of corporate design work and replacing it with his personal art. He calls it "manifesting a layoff."
"I was like, 'This is the last job I'm ever gonna have,'" he told me. "And as soon as they laid me off... I was like, 'Yes! This is the best thing that's ever happened to me.'"
The Spark: When the Body Knows
Ken’s transition to art wasn't intellectual; it was physical.
He tried different mediums from acrylics to oils, but nothing clicked. Then, one day, he whipped out a set of watercolors he hadn’t touched in 15 years to paint a portrait of his dog. It immediately felt right in his body.
That physical intuition turned into a side hustle. He started a Slack channel at work called "Paw Patrol" to annoy his coworkers with photos of dogs, which turned into commissions. He charged $80 for his first portrait. Today, that side hustle is his main hustle.
The Philosophy of "Type Two Fun"
One of the most profound things Ken shared was the concept of "Type Two Fun."
Type One Fun is fun while you’re doing it (eating cake, riding a rollercoaster).
Type Two Fun is miserable while you’re doing it, but fun in retrospect.
Ken learned this working as a bike messenger in New York City. "It’s raining, it’s snowing, you’re freezing, you’re risking your life," he recalls. But you look back on it with a sense of accomplishment.
Leaving your job is Type Two Fun. The uncertainty, the financial terror, and the rejection suck in the moment. But they are necessary ingredients for the life you actually want to live.
The Strategy: "F*ck Around and Find Out"
When asked for his advice on building a business, Ken offers a mantra that is equal parts reckless and brilliant: "F*ck around and find out in the best of ways."
Ken didn’t have a business plan. He had a willingness to try things, fail, and iterate.
He tried "Paint and Sip" classes: He pitched a local brewery and cheese shop to create a unique still-life painting event. It worked.
He tried 10-Minute Dog Portraits: An influencer challenged him to do rapid-fire sketches. He was terrified, but he did it. It blew up, and now it's a consistent revenue stream.
He tried Dance Party Portraits: He set up an easel at a loud party. Nobody wanted to sit still. It was a total failure.
He Co-Founded an Art Fair (While "Making it Up"): More recently, Ken helped build a market from scratch as an organizer for the SOMA Affordable Art Fair. It became a massive success, but in true Ken fashion, he refuses to pretend he has it all figured out. He named the group chat for the organizers, “five kids stacked in a trenchcoat," Ken told me, “because we're just making it all up as we go until we get caught."
"If it doesn't work, don't do that again," Ken says. "But even if you screw up... that's the only way to learn."
The Reality Check: It’s Not All Sunshine
Ken is refreshingly honest about the non-glamorous side of leaving corporate life.
The "Exhilaration and Terror" Mix: He describes his current emotional state as "equal bits exhilaration and terror all the time." There is no guaranteed paycheck. Some weeks he makes $4,000; some weeks he makes nothing.
The Tax Bill Reality: "One big thing that is a gigantic black hole for me is finances," Ken admits. He learned the hard way about self-employment taxes, getting hit with a massive bill one April. His advice? "Pay your quarterly taxes. It sucks so much more when you have a huge bill in April."
The Work Behind the Art: People think being an artist means painting all day. Ken corrects that assumption: "16 hours a day I'm emailing... and working on my website calendar... and like two hours a day I'm sketching."
Redefining Success
A year into his journey, a friend told him, "Kenny, you did it."
Ken’s internal reaction was, No, I didn't. I'm just getting started. But he realized his friend was right. He had done it. He had left the corporate world and survived.
"I’m working so much more now and getting paid so much less," Ken laughs. "But... I was miserable in that job even though it was paying me super well."
Today, Ken measures success by happiness. He has traded the safety of a salary for the thrill of the unknown (and the occasional Type Two Fun), and for him, that trade was worth it.
Ken’s Advice for Wayfinders
If you are standing on the edge of your own exit, waiting for a sign, here is Ken’s permission slip for you:
Make Stuff Happen: Don't wait for the gallery to call you. Pitch the idea. Send the email. Host the event. Rejection is temporary, but stagnation is forever.
Embrace "Type Two Fun": Accept that the journey will be uncomfortable, scary, and sometimes miserable in the moment. That doesn't mean you're failing; it means you're doing something worth writing about later.
Listen to Your Body: Your brain will talk you out of things to keep you safe. Your body—the pit in your stomach or the excitement in your chest—will tell you the truth. Follow the physical pull.
Ken’s Final Advice: "Just do it. 'Follow your gut' seems so trite and easy, but... if you're really feeling that thing, you gotta try to do it."
This post is part of the 101 Ways Out series: stories of people who found the courage to exit the status quo and build a life of purpose, freedom, and joy.
