Just One More Year

You are sixty-one when you finally decide to retire. Nobody really believes you. Your wife doesn’t. Your partners don’t. Your assistant quietly leaves the recurring Monday pipeline meeting on your calendar. Someone jokes at dinner that you’ll be back within six months. You laugh because that's easier than admitting you aren’t completely sure they’re wrong.

You tell yourself this really is it. You have enough money, kids are grown, your mortgage disappeared years ago. You have a house you barely use, a golf club you barely enjoy, and a calendar that has controlled your life for four decades. There is nothing left to prove. One of your partners asks if you’ll at least stay through year-end. One more year won't hurt and you've said this before.

You are twenty-three and sitting in a conference room at 2:07 AM when the associate next to you asks what you’re doing after banking. Private equity, obviously. Everyone is going to private equity. Two years in banking, then buy-side. You already have a headhunter spreadsheet open on your personal laptop. You know which funds recruit earliest, which ones have the best carry, which ones place into HBS. You hate banking. You also check your phone every ten minutes to see whether the VP replied to the deck you sent at 1:14.

When the A2A offer comes, you laugh at first. Staying was never the plan. Then the group head calls and tells you people really like working with you. Says you have a path. Says another year would be good for you. You think about the PE offer. The fund is fine. Not amazing. You tell yourself there will always be other funds. You stay for just one more year.

At twenty-seven, you are an associate and finally understand why associates become assholes. You promised yourself you wouldn’t. You would protect weekends, give clear comments, remember what it felt like to be junior. Then you get staffed on three live deals at once and discover empathy has a capacity constraint. An analyst sends you a deck at 11:46 PM with three pages that are still wrong. You type “pls fix before morning” and don’t think about it again. He does.

Your girlfriend asks if you’re still thinking about leaving banking. Of course. You tell her associate was never supposed to be permanent. You want to get through one bonus cycle and see what opportunities are out there. She asks whether that means another year. Maybe…

You are thirty-two when you make VP. The title feels incredible for approximately three weeks. Then you realize the reward for no longer being an analyst is becoming responsible for analysts. Clients now know your name. Senior bankers start asking your opinion. You get copied on fewer meaningless emails and more terrifying ones. You tell yourself VP is the ideal time to leave. You finally have credibility, experience, savings. Corporate development would take you. A portfolio company would take you. Maybe one of the clients.

Then your MD takes you to dinner and tells you he thinks you can make Managing Director.

Nobody spends ten years climbing a mountain and turns around when he can see the summit.

You get married. You miss half the cocktail hour at your own rehearsal dinner because a client is considering moving the announcement. Your wife is furious and the announcement gets pushed anyway. A few months later you tell her things will be different once you make MD. She has heard versions of this sentence before, but neither of you points that out.

Your first child arrives. You take a week off and spend two days of it responding to emails from the hospital. Nobody asks you to do this. In fact, several people tell you not to. You do it anyway. There is something comforting about being needed. Your wife notices but you do not.

At thirty-eight, you don't make MD.

This is the first time in your career that working harder has not produced the next thing. You take it badly and your wife suggests maybe it's a sign to leave. You almost agree but the group head tells you next year looks very good.

At thirty-nine, you make it.

The email comes while you are in the back of an Uber. You read it three times. You screenshot it and send it to your wife. She sends back four hearts and “proud of you.” You look out the window and try to feel what you imagined this would feel like when you were twenty-three. It feels good, but not good enough.

MD turns out to be another beginning. Now you need clients, revenue and relationships. The coverage bankers you spent your twenties making fun of suddenly look smarter than you remember. You start taking CEOs to dinner and playing golf seriously. You become good at remembering spouses’ names, children’s schools, who is fighting with their board, who secretly wants to sell. You tell yourself you will do this for five years, bank some real money, then step away while you are still young enough to enjoy it.

Five years becomes seven because the market is weak. Seven becomes nine because the market comes back and you have finally built momentum.

At forty-eight, you have your best year ever. Leaving now would be insane, you may as well stay one more year.

Your daughter is thirteen when she stops asking whether you can come to things. She just sends the schedule to your wife. You discover this accidentally when you ask what time her game is and your wife says, “She didn’t think you’d make it.”

You make the game, but on your phone for most of the second half.

Afterward your daughter says she’s glad you came.

You decide you need to slow down. Not quit, necessarily. Just create boundaries. Fewer dinners, fewer weekends. You tell yourself after this current deal closes you’ll start doing that properly. Then the deal closes, but another one starts.

You are fifty-four when a first-year analyst asks how long you’ve been at the firm. You tell him, he looks genuinely shocked. He says he could never do banking that long and you laugh.

Your son graduates from college and has no interest in finance. Secretly, you're relieved. At dinner, someone asks him what he wants to do and he says he cares more about having an interesting life than making a lot of money.

You look at your wife, she looks down at her plate.

At fifty-eight, retirement becomes a real conversation. You have enough, but one of your biggest clients tells you he is considering a transformational acquisition and wants you personally involved. It could be the largest deal of your career, and shouldn't take no more than a year.

At sixty, the deal signs.

There is a photograph of you shaking the CEO’s hand. It gets framed and put in your office. People congratulate you. Someone says it is a hell of a way to finish.

You like the sound of that.

Then your partner asks if you can help transition the relationship. No more than six months. You built this client over twenty years, it would be irresponsible to just disappear.

Now you are sixty-one, sitting at your retirement dinner, and someone asks how you managed to stay in banking for nearly forty years.

You think about the question and you never decided to.

Nobody ever chooses forty years, they choose one year forty times.

The next morning you wake up before six without an alarm. Your phone is quiet. No overnight comments. No client emails. No analyst asking whether you have five minutes.

You make coffee and sit in the kitchen.

Your wife comes downstairs and looks surprised to see you there.

“What are you doing today?” she asks.

You don’t know.

For the first time since you were twenty-two, there is no next promotion, no bonus cycle, no live deal, no client to win, no reason to stay until next year.

You look at your phone anyway and it rings.

Headhunter.

A private equity firm is looking for a senior advisor on one of their largest portfolio transactions. Twelve-month contract. Limited travel. Flexible schedule.

You laugh.

Your wife asks who it is, and you tell her. 

She stares at you.

You tell the headhunter you’re retired, and he tells you that's exactly why he called.

You look out the window and take a sip of coffee.

“Send me the details.”

Just one more year.