In early 2025, I left my 9 to 5 (More like 5am to 7pm) work life. I wasn’t pushed.
Like the F.I.R.E theme of this site, it was part of a plan I’d put in place years ago. In fact, for anyone in my life, except my employers, my plan to retire early was the biggest open secret.
Didn’t hate my job or what I do. I got into my original career (advertising) in my 20s, knowing that less than 2% remain in the business after 50. To that end, I’ve always worked as if my career would be short and tried to save based on an accelerated timeline in order to be financially ready. I’d planned for the worst case, but due to some smart career pivots, I was able to beat the odds in my industry.
Yet while in my 50s working and still feeling at the top of my game, one day, my brain tapped me on the shoulder to say, it didn’t want to play this game anymore. My body didn’t give out or got old – I just realized the game did. The game of winning an accumulation of perks and wins didn’t interest me anymore. Money stopped being a scorecard for success, something to spend my valuable time to acquire.
I now saw it as a resource to buy freedom. Freedom of speech, time, nodding at corporate Bullsh*t, and to enjoy personal pursuits. To help teach lessons to a next generation after a career of learning them. To work in order to please myself-not a balance sheet.
In March of 2025, I pulled the trigger. Now, looking at my life in corporate America slowly getting smaller in my rear view mirror, I can see a lot of work and life lessons. A viewpoint that illustrates the often chaotic mix of challenges, uncertainty, frustrations and exhilaration that make up a career.
A lot of lessons I often learned the hard way. I share them with you in a note I posted when I announced my F.I.R.E. moment to friends. Maybe one or two might resonate with you, help you skip a few hard-learned lessons in your own career and remind you why you, too, also need to think about an exit plan.
What’s In a Career? 36 Years in 120 Seconds.
Experiences for me as I purposely choose to move on, maybe lessons for others:
Hired the same day I interviewed. Moving a lot. Smiling too much. Meeting shockingly brilliant people. Watching others do meetings better than their jobs. Realizing THAT’s the real path to most executive positions. Feeling you’ll be outed as a hack. Finding you may not be one after all. Mistakes, lucky breaks and good mentors.
Feeling you don’t get paid enough. Thought it’d take a compromising photo of the CFO to get paid this much. All-nighters. Endless hotels stays and using planes like Ubers. Free, but realizing the real cost was valuable time with family and loved ones. Learning how to say F*ck you in corporate speak and that smiles hide swords. Learning the best skill in business: good storytelling.
Mistaking busy for important. That if you’re married to your career, your partner is probably your mistress. Learning that passive aggressive people are just shy a-holes and corporate America is just high school with money.
Realizing corporate culture’s job is to seduce you to deliver more than your employment contract specifies and loyalty to employer ruins your career’s pricing power in the long term. No number of awards or who gives them out can ever replace hearing your dad say he’s proud of you.
Seeing the writing on the wall in my industry after the .com bust, pivoting to tech and watching peers ignore changes, then struggle moving from ad men to math men. Winning an Oscar (For technical achievement. For Acting? God no. They gave one to Suicide Squad, but they’re not THAT crazy). Starting and holding a business together across two market crashes sometimes wondering how to make payroll along the way. Selling a product I created to Apple.
A virus telling me I can live life differently and learning that my best work skills were driven by my worst flaws. Watching some being a D*ck in business to get ahead is like the Dark Side of the Force (easier, more seductive). It’s a harder path to be good to, care about and support good people on the way to success.
Age beliefs make your career life more like Logan’s Run and seeing Gen Z on my staff and looking at them the same way Bruce Willis looks at his younger self at the airport in 12 Monkeys. Watching Linkedin slowly become Facebook. Realizing graveyards are filled with irreplaceable people, nice cars rust, and it’s not a flex to be the richest person at the assisted living facility.
Even though it doesn’t sound like it, I enjoyed the ride (perverted, right?). And now, remembering Roy Batty from the movie Blade Runner, “All these moments will be lost in time…like tears in rain.” And, you know what?, they should be. Time laughs at you and people pity you for holding on to the past too long until one day you become a museum piece, a static container of history.
My recent obsession watching YouTube videos of musicians and actors getting old and seeing both my parents hit health quality of life walls at 75 brings that home.
Looking back, a career is just a mix of skill, luck and a few people who said “yes” to you at the right time.
Blessed to have had all three. So…anyone know if The Gap is hiring?