There’s a chair I’ve sat in more times than I can count. It’s across the table from a leader — sometimes a CEO, sometimes a pastor, sometimes a young executive who just got the promotion they’d been chasing for years. Thirty-some years of mentoring leaders has taught me a lot of things, but one has stayed with me longer than the rest: the leaders who worry me most aren’t the ones just starting out. They’re the ones eighteen, twenty, thirty years in. The ones who started with fire and are now coasting on fumes, or worse, quietly making decisions they never would have made at year five.

Starting strong is common. Finishing well is not.

Here’s a number that ought to stop every leader in their tracks. Dr. J. Robert Clinton, who spent decades studying leadership in the Bible, once catalogued around a thousand leaders mentioned in Scripture. Of those, he could find enough biographical detail on about a hundred to actually study how their leadership played out. And of that hundred, only about a third finished well.

One third.

Read that again. ONE THIRD!

These aren’t obscure names, either. Clinton’s list of leaders who finished poorly includes Gideon, Samson, Saul, and — this one always lands hard — Solomon. The wisest man who ever lived started with a temple and ended with a thousand wives pulling his heart toward other gods. Meanwhile the ones Clinton identifies as finishing well include Joseph, Caleb, Daniel, and Paul. Same Bible. Same God. Wildly different endings.

What’s the difference? It’s almost never talent. Every name on that “finished poorly” list was gifted. Gideon led an army of three hundred to a wild victory. Saul stood a head taller than everyone and started well enough that Samuel anointed him with genuine hope. Solomon built one of the wonders of the ancient world. Talent was never the problem. Character was.

Six Things that Sink Leaders

Clinton names six things that quietly sink leaders in the back half of their lives: money, power, pride, sexual sin, family neglect, and plateauing — that slow settling into coasting where you stop growing and start just occupying a title. Notice that none of these are dramatic character collapses. They’re erosion. A little compromise here, a little neglect there, a little pride that goes unchecked because nobody close enough to you has permission to name it.

And here’s what struck me studying the leaders who did finish well, like Daniel: it wasn’t one big decision late in life that saved them. It was a handful of ordinary habits, kept up over decades. Daniel kept praying three times a day even when it became illegal and could have gotten him killed — and that was in his eighties. He kept learning, still poring over Jeremiah’s scrolls near the end of his life, still hungry to understand what God was doing. His walk with God in chapter nine reads like a young man’s, not an old statesman’s. Paul, near the end of his own life, sitting in a cold Roman cell, still asked Timothy to bring him his books and his scrolls. Still learning. Still growing. Right up to the end.

What About You?

So what do you actually do with this if you’re the leader in the chair across from me right now? First, get honest about which of Clinton’s six barriers has your name on it. Not your neighbour’s. Yours. Most of us know, if we’re willing to look. Second, find people, plural, who have permission to tell you the truth before it costs you your legacy. Clinton’s research found that leaders who finish well typically had ten to fifteen people who spoke into their lives at key moments. Not one wise mentor. A whole cast of them, appearing at the right seasons. Third, build in seasons of renewal on purpose. Don’t wait for a crisis to force you into stillness with God. And fourth, guard your learning posture. The moment you decide you’ve arrived is roughly the moment you start to drift.

Here’s my question for you today: if someone did Clinton’s kind of research on your life twenty years from now, which list would they put you on?

I can’t answer that for you. Neither can your resume, your platform, or your last performance review. It gets answered in the small, unglamorous choices you’re making this week, the ones nobody’s watching.

I’ve watched enough leaders finish both ways to tell you this much: it’s never too late to change direction. Gideon and Solomon didn’t get a do-over, but you might still have decades left. Begin again with the end in mind. Ask God to search you, keep the people around you who’ll tell you the truth, and keep choosing, day after ordinary day, to finish well.

That’s the whole challenge. Not one dramatic finish line, but ten thousand small ones.

Reflection: Of the six barriers, finances, power, pride, sexual sin, family neglect, or plateauing, which one would the people closest to you say you’re most vulnerable to right now? And who has permission to tell you the truth about it? That is what a good mentor can do.

Grace and courage to you as you keep going,