The Ripcord

Nobody exits well by accident.

Two things are certain in this life, and one of them is that you’re leaving your business.

I mean that in the widest sense. If you own the business, you’re leaving it. If you work for the business, you’re leaving it. The only questions are when, on whose terms, and whether the guy who eventually walks out the door is grateful for the decisions the guy sitting in the chair is making right now.

The exit conversations have typically come up around me in two flavors, and when you pay attention, you realize they’re the same conversation.

The business owner flavor arrives with a timeline stapled to it. “We’re building this for ten years, then we sell.” Sell to private equity, maybe a competitor. It’s ambitious and it writes cleanly on the whiteboard. And my first question is: why ten? A lot of ten-year plans are really a polite way of saying “I don’t want to think about this yet,” and others are pure “I get rich and walk away”, and sometimes it might just be a partnership that has that uncertainty in the back of their minds if they can actually stay together past 10 years, so they need to build it big and fast and offload it in order to secure individual freedom.

The executive flavor sounds different, but it’s the same species. “Good gig, great comp, I’ll retire out of here.” Also clean on the whiteboard. Also, from what I watched across twenty years inside big companies, rarely how it goes. Careers at that altitude don’t usually end on the schedule the executive drew at forty. They end because the organization turned, or a leadership change put a new name above yours, or somebody in HR noticed you just became pension-eligible at fifty-five and found that interesting. (hmmmm kind of smells like a business owner partnership that can fade.)

Both stories sound like they’re about timelines. They’re actually about the same thing, and after a lot of years, one name keeps floating up for this: optionality. The whole game is whether you get to choose.

For an owner, the first five years of decisions are either building optionality or spending it. Systems somebody else could run, or a chair only you can sit in. Client relationships that belong to the company, or a book of business that lives in your phone. A team that could carry the thing through a transition, or a company that folds if you take six months off. None of that has to be answered in year one, but it does get answered by year five whether you meant to answer it or not.

Same math on the executive side, different line items. Savings that would let you walk if you had to. A real understanding of what your equity compensation does on the way out; when it vests, what it can trigger at tax time, what it actually turns into. Skills that travel, or fifteen years spent becoming irreplaceable inside one specific org chart. A network that exists somewhere other than the company directory. Building it or spending it, year by year, and the balance rarely gets checked.

Here’s the uncomfortable part: people don’t usually notice they’ve been spending optionality until the day they reach for it and it’s gone.

I recently read a post from an NFL player named Logan Ryan, a two-time Super Bowl champion, where he states that he made about eighty million dollars in his career and touched almost none of it. His explanation was simple: he played the whole time knowing the league could pull the ripcord on him any day, and he wanted to be able to walk away with a big stack and live. That’s the entire framework in one sentence. Whatever your number is, the question is the same: are you building the version of your life where the ripcord gets pulled and you’re fine?

Now the softer half, because I can’t be writing this like it’s doomsday. Optionality isn’t pessimism and it’s not bracing for the worst. It’s building for the choice, so that whichever way it breaks, you’re the one choosing.

For an owner, that might mean building the business to the point where it could be sold, passed to family, handed to the employees, run for cash flow indefinitely, or wound down cleanly; not because you’ve picked one, but precisely because you haven’t, and you want the pick to still be yours when it matters. The path you end up taking might be one you couldn’t have named in year three. That’s cool, my friend. What matters is that you actually had paths.

For an executive, it might mean enough cushion to survive a change, enough understanding of your equity to not get blindsided in April, enough of a reputation that the next thing finds you, and enough clarity about what you actually want that you’d recognize the right exit when it came knocking.

And about the fifty-five-year-old getting the “early retirement” nudge: that story is not the ending it feels like. Companies move senior people out for reasons that are structural far more often than personal. It’s like a relationship where the other person realized a year ago they wanted different things; it’s a mismatch, not a rejection. The question for the person on the receiving end isn’t “what did I do wrong.” Usually, nothing. The question is “did I build a life that survives this well from this moment forward.”

Some did. Some didn’t. The ones who did tend to say some version of “I knew this could happen, so I built like it was already on the calendar.” The ones who didn’t say “I didn’t think it would happen to me.” Same event, two different exits, and the difference was built years earlier.

There’s a version of this piece that turns into a lecture about savings rates and vesting schedules and succession documents. It’s been written a thousand times and it lands as advice, which is the wrong frame and not my job in this piece. This isn’t about what to do. It’s about what to build for.

Build for the choice. Build for the day the ripcord gets pulled, or the day you decide to pull it yourself. Build so that when the exit shows up, in whatever costume, you’re the one setting the terms.

Because the exit is coming, for the owner and the executive both. The only question is whether it finds the version of you with options, or the version who used to have them.

Two weeks’ notice is amateur hour on the way out. But the real work was not going to happen in those two weeks anyway. The real work is the ten years before them.

— Travis

P.S. If you’re inside a career or a business right now and haven’t thought about the exit, that’s the tell. The people standing upright when it happens started building long before it looked necessary. Send this to somebody who’s playing like the ripcord doesn’t exist.