Let Me Tell You a Story About a Man With a Plan
A letter to my 30-year-old self — and to anyone trying to outrun their own life plan.
Let me tell you a story.
It’s London, early 2000. A Wednesday night that’s technically Thursday morning now. You’re in a narrow room at the Tower Thistle Hotel, staring at an IBM ThinkPad 240, willing a PowerPoint deck into clarity before your 8 a.m. with the regional CEO and CIO. The hotel internet feels like it’s running through damp string. Outlook won’t sync. Your Ericsson T28 is blinking — a missed call, two messages, a text.
You don’t check them yet.
The room smells like black coffee and burnt nerves. You’ve been living out of a suitcase since Monday — meetings in Canary Wharf, dinner with the regional execs, and now a final pitch to wrap the week. You’re here running a critical integration for a European acquisition. You were told it’s urgent. You were also told you’re the only one who can do it.
There’s a burp cloth folded into the side pocket of your laptop bag. Your daughter is three months old.
She’s at home in Chicago. You left Sunday evening, just after rocking her to sleep. Her mother hasn’t slept much since. Neither have you.
This was the plan.
You’re thirty-two. You’ve got a full-time executive role, a new mortgage, a new baby, and an MBA from the University of Chicago in full swing. Classes on Fridays, Saturdays, and Sundays. Sometimes Mondays, too. Most people take three to four years to finish the program. You gave yourself two, maybe two and a half.
You’re also still the guy who hosts dinner parties, sends birthday gifts, and organizes weekend brunches. You like people. They like you back. There’s a kind of choreography to it all — social, intellectual, professional — and you’re proud of how well you dance through it.
Except lately, it doesn’t feel like dancing. It feels like running next to your life instead of inside it.
You rub your eyes. The clock says 12:41 a.m.
You click through one last slide and then — maybe it’s curiosity or guilt — finally flip open the phone. The message is from your wife. It’s a series of texts. Your daughter, in her pink onesie, grinned wide enough to swallow the room. Her first real smile. And apparently, she smiles when Mom says the word “Daddy”.
You hadn’t known that moment was coming. And now, it’s already gone.
You stare at the texts for a while, then tuck the phone under your notebook and go back to formatting bullet points. Because the meeting is still happening in the morning. Because you’re still the one they’re counting on. Because the plan doesn’t stop for feelings.
You tell yourself you’ll make it up on Sunday.
You built the plan to win.
Graduate. Work. MBA. Promotion. Legacy.
Be admired. Be needed.
Then — maybe — rest.
You believed in the plan like people believe in physics. Not because it’s emotional, but because it’s logical. Repeat the steps, and life unfolds. Stay on schedule. Don’t miss the train.
But here’s what the plan didn’t account for.
It didn’t account for a baby’s smile breaking you open in a hotel room across the world.
It didn’t account for the silence on the other end of the phone when your wife says she’s “fine,” and you know it means she’s overwhelmed, exhausted, and trying not to say something you’ll carry into your meeting.
It didn’t account for the quiet hollowness you started to feel even while excelling. The kind that shows up between applause, when the room clears and your heart whispers: This isn’t quite it, is it?
The promotion came the next year.
A massive role. San Francisco. Your dream city. A real shot at a Level 2 enterprise post — more influence, more money, more visibility.
And more absence.
It would have meant commuting between Chicago and San Francisco weekly for a year. Five or six days away from your daughter and your wife. Watching her grow up through voicemail and Outlook reminders. You ran the math. You even visited the apartment building. You imagined the split-level office. The title on the door.
And then you said no.
Your boss was stunned. Maybe disappointed. He stopped advocating for you after that. You noticed. So did the people around you. The momentum slowed. You were no longer “next.”
But your life? It opened.
Your daughter learned to walk, and you were home to cheer her down the hallway. You picked her up from daycare. You made dinner on Mondays. No one wrote headlines about it. But something in you softened — not your ambition, just your sense of what it was for.
And then, in 2006, it happened again. You were at another fast-growing Fintech by then.
You were told the path to the executive suite required full sacrifice. Be available always. No vacations. No personal distractions. The culture demanded it.
You said no.
You still performed. Still delivered. Still led with integrity and earned trust the old-fashioned way — by showing up, not just logging in. You were promoted anyway. Quietly. Without spectacle.
You built high-performing teams. Created trust. Fostered growth. You didn’t burn out — you lit up the people around you.
But in 2015, it all came to a stop.
The leadership changed. The climate shifted. Suddenly, you were told again to be someone else. Someone you weren’t willing to become.
They called it culture. You called it misalignment.
And you stepped out. Again.
Now, in your 50s, you look back at that week in London often.
Not because of what happened in the boardroom, but because of what broke open in the quiet.
Those texts. That smile they put on your face.
That question: What if I’m getting all of this right and still missing everything that matters?
You remember the weight of the burp cloth in your bag.
The way the cab smelled like warm leather and rain.
The way your wife didn’t say she needed help — she just kept going.
And the way you decided: I’m not going to let this plan swallow the person I love becoming.
There are days — rare, flickering days — when you wonder what would’ve happened if you had said yes to San Francisco. If you had played the game harder, leaned in sharper, and nodded faster.
But those thoughts disappear quickly.
Because you know:
Had you followed the plan,
You might have become celebrated.
But you would not have become yourself.
So here’s what I want you to remember — you, at 30, or you, at 33, or 36, or wherever you are right now:
Your life isn’t late.
It’s just not linear.
It’s not about keeping pace.
It’s about keeping presence.
The plan is a map.
But your heart is the compass.
And when in doubt — when the promotion dazzles or the voice on the phone says she’s “fine” — look at the texts.
Then smile.
And ask: Will this version of me still feel like home when the meeting ends?
If not, you know what to do.
Enjoy your loved ones and the rest of your Sunday!
And thank you for spending some of it with me.
Warm regards,
Adi