Not Done Yet
Setbacks, comebacks, and lessons in between
There is a moment in life when the ground drops out from under you. One day, you're standing firm; the next, you're free-falling. It might happen at 25, at 40, or at 65. For me, it happened at 35. Then again, in my late 40s. Then in my early 50s. And, because life has a sense of humor, once more, right now.
I have restarted so many times that I should get frequent flyer miles for comebacks.
For years, I bought into the idea that life follows a steady arc. Work hard, build something lasting, and eventually, you get to kick back. But life doesn’t care about your plans. It twists, flips, and sometimes sucker-punches you at 2 a.m. with a single phone call.
The Call to Change (Or, the Call That Wrecked Me)
I was 35, running Asia operations for a mid-market global company. For someone so young, I felt like I had cracked the code. I had made it. Six months in, they added me to the global executive team, validation that I was on the fast track. I was working across time zones, making big decisions, and soaking up every bit of the thrill that came with it.
Then, on a regular Tuesday, my phone rang. In one breath, they told me I was out. No warning. No severance. No soft landing. Just... gone.
By Thursday, I was on a plane back to Chicago, and everything I had worked for vanished. I landed at O’Hare with the proverbial two suitcases. No job and a bank account that suddenly felt a lot smaller. I had left behind my strength (my wife) and pieces of my heart (our two little ones at the time) until I could get back on my feet. If there was a neon sign flashing Welcome to Rock Bottom, I had just walked right under it.
So, I started again. New job. New city. A new professional identity. And for a while, it worked. Until it didn’t.
The Late-40s Reality Check
In my late 40s, I had climbed the corporate ladder again. I nailed some big wins, efficiency overhauls that saved the company millions, and restructuring operations that made teams hum. And my reward? Another gut punch.
Apparently, when you make operations too efficient, you can optimize yourself right out of a job. Who knew?
This time, it felt different. There was a sinking realization: I had played the game, done everything right, and still ended up in the same place, having to start over. Again.
“Beginnings are usually scary, and endings are usually sad… but it’s everything in between that makes it all worth living.” — Bob Marley
The hardest part of starting over isn’t the work. It’s the fear. The discomfort of stepping into the unknown, of not having a safety net. But the truth is, being unsettled is where growth happens. It’s where we shed what no longer fits and make space for what’s next.
“It is never too late to be what you might have been.” — George Eliot
The Turn (A.K.A. If They Can Do It, So Can I)
I started looking at others who had reinvented themselves, not in some far-off past but now.
Sarah Blakely built Spanx from nothing in her late 30s. Jeff Bezos left a cushy finance job to start Amazon at 31, and now he’s... well, whatever the bald, rocket-loving version of himself is now. Vera Wang didn’t design her first dress until 40. Heck, even Steve Jobs had to start over at 45 after being booted from Apple.
And in my industry, Fintech? Jack Dorsey left Twitter and started Block in his 40s. Anne Boden founded Starling Bank in her mid-50s. Howard Schultz came back to Starbucks after stepping away. These aren’t stories from history books. They’re happening now. If they could pivot, so could I.
Starting over in midlife isn’t just possible. It’s always happened all around us. More proof. Julia Child was 49 when she launched her first TV show. Ray Kroc bought McDonald's at 52. Arianna Huffington started The Huffington Post at 55. Colonel Sanders? He didn’t franchise KFC until he was 62. Every one of them faced setbacks, doubters, and moments of uncertainty. But they kept going, proving that reinvention isn’t just for the young; it’s for the determined.
So, I took small steps. I tried. I failed. I tried again. And with each attempt, something unexpected happened: the fear started fading.
Hope started creeping in.
Climb One More Time
Hope isn’t some fluffy, feel-good thing. It’s a fight. It’s standing up when you’re dead tired and still swinging.
I started embracing the uncertainty instead of fearing it. Life isn’t a straight climb to success. It’s a series of summits and ass-over-teakettle descents, each restart an invitation to discover something new.
I let go of the fear of wasted time. Every past failure had been a lesson, not a loss. Every setback? Just another rep in the gym of life.
I built my own thing. A business that scaled to seven figures in annual revenue. I exited successfully. Victory, right? Cue the confetti and easy retirement brochures. Not quite. Because my next move, the one I thought would be my legacy project, flopped.
I bootstrapped it. Poured my own money in. Watched as, month by month, my liquidity drained and my confidence with it. The terrifying realization set in: I had nothing solid beneath me. It looked like I had run out of moves.
But if there’s this thing I’ve learned. When life shoves you into a corner, you fight your way out. I wasn’t done. I wasn’t out of options. I just had to find the right one.
The Arrival (For Now)
So now, I’m doing it again. But this time, I’m using everything I’ve learned to build an accelerator to help emerging leaders become phenomenal corporate executives or solopreneurs. Because if there’s one thing I know, it’s how to start over. And I want to make sure others don’t have to do it alone.
I don’t know where this chapter will lead. None of us do. But here’s what I know.
It’s never too late to begin again.
Not at 20. Not at 50. Not at 80. The only true ending is the one we refuse to rewrite.
So here I stand, once again at the threshold. The page is blank, the road unwritten. And for the first time in a long time, I’m not afraid.
Because starting over doesn’t mean going back.
It means stepping forward into something new, into something possible, into something that might just be the best damn chapter yet.
And you, my readers, keep my hope alive every week between Sundays. Thank you!
And remember ~ Always Assume Positive Intent!
Warm regards, and I hope you enjoy the rest of your Sunday.
Adi