CEO Coaching: Leading in the 4th Quarter of Your Career

Being a CEO has always been hard—but never harder than the stretch that started with COVID, slogged through the “WFH or not” chaos (still unresolved), and got sucker-punched by the 17-times-rebooted tariff debacle. It’s been a perfect storm of instability—like a tornado in a trailer park.

As one seasoned (and successful) CEO told me, “The challenges of this period have exceeded the cumulative crap of the entire rest of my career.”

While getting promoted into the CEO role during this mess is its own kind of shock therapy, today I want to talk to the seasoned vets—the Tom Bradys and Aaron Rodgerses of the business world. (Minus the supermodel exes and ayahuasca trips.) You’re in the fourth quarter of your career: banged up, not as fast, maybe questioning if you’ve still got it, but still in the game trying to lead your team to the playoffs.

Here are a few thoughts for that group:

It’s OK to feel worn out.
Really. You’ve been asked to do superhuman things—navigate a pandemic, motivate remote teams, cut costs while investing in innovation, and manage culture, customers, and capital… simultaneously. (As my daughter’s boss once said, “I feel like a one-legged man in an ass-kicking contest.”) Don’t make it worse by beating yourself up for feeling exhausted.

Don’t head for the bench just because you’re tired.
Unless your physical or mental health is at stake, staying in the game might actually feel better than quitting. No, you might not go out on top, champagne-drenched in the boardroom, but you can go out swinging—knowing you gave it your best when it counted most. That pride matters. And your team will feel it too.

That said… if it really is time to go, do it with joy.
If the plan was to be on a beach somewhere—go! Your team will miss you, sure, but your obligations to your family and yourself matter just as much. “Leave it all on the field” is a nice phrase, but let’s be honest: no one wants to hobble off that field, broken and bitter. You still need energy for whatever’s next.

Don’t stop learning just because you’ve been around the block.
The surest way to get benched in the fourth quarter? Coasting. Just because you could play the game on muscle memory doesn’t mean you should. The best leaders I know stay hungry and curious. Don’t assume your fire’s gone out—maybe it just needs a poke.

The great game of business needs savvy veterans and ambitious rookies. So if you’re in the fourth quarter, ask yourself: what would reignite your drive? If you don’t know the answer, get some help—or grab a beach chair.