My Biggest Mistake
It’s impossible to share our mistakes without talking about regret or pain or loss. But it’s also possible to talk about them as lessons learned, facts found, and truths revealed…. In 2019, I was invited to share my “biggest mistake” in front of 275 people as part of a special engagement for Chicago Ideas Week. Below is the essay I read on stage:
There are 3 moments in my life where I made remarkable mistakes:
- The first mistake was at 13 when I missed my opportunity to say goodbye to my grandfather before the cancer won. For months, I bared witness to his chemo treatments, endless cans of chocolate Ensure, and the disease’s aggressive victories. I sat alone by his bedside, listening to his labored breaths waiting for the perfect stillness to tell him how much I loved him. Eventually, my mom and I changed guard and I went back to reading Nintendo Power magazine in the spare bedroom. My mom’s wails rang out like a siren. My grandfather died in the arms of his wife and his daughter while I just stood at the foot of the bed — and waited.
- The second mistake lasted 8 years—even though it really should’ve only lasted 8 weeks—because I was addicted to a toxic relationship that dragged out across high school, college, and an entire year after graduation. I let her manipulate me, lie to me, cheat on me (several times) all while waiting for the final dealbreaker — the last straw — to tell her it was over for good. Missing out on years of youthful exploration, experimentation and self-discovery, I endured a gnarly long-term, long-distance mindfuck — and waited.
- The third mistake was a gradual, slow-drip failing spanning two my decades in the design industry. Somewhere along the way, (almost imperceptibly) I began trading creative fulfillment and meaningful work for upward mobility and job security — subverting my passions and wait-listing an ever-growing collection of personal projects. And this waiting filled me with resentment and frustration and angst. And it made me really possessive of my time. In fact it kept me from starting a family for fear my children would consume what little time I felt I had left to realize my dreams. And instead of giving myself permission to reprioritize life and work, I let these ugly, angry feelings compound — and I waited.
So you see, my biggest mistake wasn’t an exact moment. My biggest mistake was waiting too long for the exact moment.
This year I turned 40, we had our second child, and I quit everything. I quit my job. I quit my freelance clients. I quit waiting. After 20 years of building other people’s dreams for a living, I decided to take an entire year off and build my own. I launched Dadwell & Co., a podcast at the intersection of creativity and fatherhood as an excuse to interview men I admire to better understand how they reconcile their dual identities of entrepreneurial creative and present, engaged dad.
The last 6 months have been the most humbling and rewarding of my entire career. The reset fundamentally changed how I think about life and work and my wife and kids. And the show gives men space to share their feelings, work through relationships, and sort out their careers. In a beautiful way it’s addressing all my biggest mistakes.
Now none of this makes any sense—especially financially—I’m married, with a mortgage, two kids in Montessori, and I’m supposed to be settling into my career and entering my “earning years”. It actually feels like the worst possible time to take a year-long sabbatical and work on a project that generates zero revenue.
But when I look back at those 3 moments, the “mistake” was the waiting. Waiting for the perfect time: when the stars align, or god sends a sign, or your calendar is finally clear, or your to-do list is done, or your student loans are paid off, or you have enough in your bank account, or you get enough experience, or earn that title, or get that raise, or when you have enough vacation stockpiled, or your kids are out of the house, or you finally retire…. But it’s never enough.
And so you find yourself waiting. Waiting to say what’s in your heart. Waiting to leave your abusive relationship. Waiting to reset your life. Waiting to care for yourself. Waiting to take the time. Waiting to lose weight. Waiting to start a family. Waiting to start that project. Waiting to change jobs or careers. Waiting to go back to school. Waiting to take that holiday. Waiting to make moves. Waiting to live.
Sometimes, it feels right to wait. To be patient and deliberate. To avoid rash decisions or rushing into things. To be prudent, pragmatic. Sit down and figure out when’s the best time to do this. But the great cosmic joke is: the “best” time doesn’t exist. It’s a myth. It’s a red herring. It’s a distraction from right now. The reality is it’s actually always the “worst” time — especially the bigger, bolder, riskier the call-to-action is. But this isn’t really about taking risks. This is about the stories we tell ourselves until they become true. Until we script ourselves into plot lines of quiet inaction, waiting for the magical moment… but the chapters just keep turning and turning and turning without climax.