From Corporate to Creative: Five Lessons I Still Use Every Day
I entered the corporate workforce at 22 and stayed until I left Amazon in late 2024. If you’re doing the math, that means nearly my entire adult life - and all of my professional experience - took place in corporate environments.
When I started working as a full-time artist and writer last year, I found it unsettling to be the only person in the room without an MFA in creative writing or ten years of animation experience with Disney. For a few months, I carried the anxiety of “starting over” at this stage of life.
As the months ticked by, it became apparent that some things were actually easier for me because of my past career. I realized that there is no such thing as truly starting from scratch with this much life experience in hand. I had assumed that all of those years in corporate roles would both help and haunt me in this next chapter. Unsurprisingly, that turned out to be true. What did surprise me was which experiences proved most helpful.
My brain has done a lot of necessary rewiring over the last eighteen months, but these are the lessons I’m holding onto:
#1: Fly the Plane While Building It
Over my corporate career, I held at least a dozen roles across multiple functions at four companies, not including stretch projects and temporary assignments. That meant spending a lot of time learning while doing, and later, learning while leading. Repeating that cycle made me comfortable with this familiar corporate turn of phrase: “flying the plane while building it.”
Time and again, I learned that persistence moves you up the learning curve toward competence and, eventually, mastery. I now find myself in that environment again on a much larger scale, and my corporate experience keeps me calm and steady. The discomfort of being a newbie isn’t a trigger for panic or despair; it’s a cue to study, practice, seek feedback, buckle up, and build.
#2: Focus on Inputs, not Outputs
I have to thank Amazon for making this a daily mantra for over seven years. The idea is simple. If I set a goal to run the New York City Marathon, I can’t directly control that outcome from where I am on the couch. What I can control is getting the right shoes, starting a training plan, sticking with it, tracking progress, eating well, and sleeping enough.
My focus is on lacing up my shoes and putting one foot in front of the other.
Those controllable actions are the inputs - the small, daily decisions that move me toward the desired output. What I appreciate most about this mindset is how it protects me from being overwhelmed by the distance between where I am today and my long-term goals. It keeps me grounded in what I can do right now. I may have Grete Waitz in mind, but my focus is on lacing up my shoes and putting one foot in front of the other.
#3: Make Peace with the Cutting Room Floor
One of the great privileges of working in corporate retail was collaborating with extraordinarily talented designers. My role required selecting a small number of designs from hundreds of thoughtful, beautiful options to move into mass production. The rest landed on the cutting room floor.
It was a creative business - but a business all the same - operating within finite resources, constraints, and considerations beyond the standalone merits of any one design. I’m grateful for that experience now. Not every line of prose I write will make it into the final draft. Not every character I draw will get to tell their story. Many beautiful things will end on my cutting room floor, or that of a publisher or retailer, and that’s part of the process.
Not every line of prose I write will make it into the final draft. Not every character I draw will get to tell their story.
It may hurt. It may hurt a lot. But the creative act has value on its own, and some days that has to be enough.
#4: Choose Collaborators Consciously
In corporate life - as in life - we don’t always get to choose our collaborators. When that’s the case, the challenge becomes navigating different styles, priorities, and personalities in service of a shared goal.
But sometimes, you do get to choose, and when you do, that decision matters enormously. Whose perspective will be helpful? Whose skills fill the gap? Who understands not just the work, but the why behind it?
Building teams and task forces taught me these lessons through both success and failure. I’ve seen firsthand that what’s created through conscious collaboration can exceed the sum of its parts. At this stage of working for myself, I get to pick my collaborators. These individuals understand my vision and want me to succeed, but will challenge me, ask hard questions, and hold me to high standards. I believe my work is better for it. Choosing collaborators carefully has become one of the most important strategic decisions in my creative journey so far.
#5: Be Willing to Be Misunderstood
I also owe this lesson to my time at Amazon, where taking bold, calculated risks wasn’t just encouraged, it was expected. Trying something truly new often meant being misunderstood, at least at first. Learning to tolerate that discomfort was part of the work.
I think of this now as an invitation to leave my ego at the door. I’m doing something new, risky, and long-term. I stepped away from a clearly defined path into one that’s more ambiguous and harder to explain. It isn’t going to make sense to everyone and that has to be okay.
Creative work requires tolerance for ambiguity, not only in the work itself but in how it’s perceived. Being willing to be misunderstood frees up the energy needed to keep going and stay focused rather than seek immediate validation.
My corporate career didn’t disappear when I stepped away to build my creative one. All those years came with me and have helped me stay grounded, focused, and resilient as I build something of my own.
The totality of a life can’t fit into a single blog post. If you have a past-career experience that’s shaped your creative path, I’d love to hear it. Drop me a note.