The Mentor Nobody Offered Me — and the One I'm Trying to Be

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For most of my early career, I was doing it alone.

Not literally alone — I had colleagues, supervisors, even some good friends at work. But I was navigating the hard questions without anyone ahead of me who seemed interested in helping me figure them out. Questions like: Am I in the right role? Is this growing me or just consuming me? How do I lead people without losing myself? How do I stay grounded in what matters when the system keeps rewarding what doesn't?

I watched other people who seemed to have a person in their corner — someone who believed in them, challenged them, and gave them honest feedback from a place of experience. I wanted that. I waited for it longer than I should have.

In my late thirties, a man named Harold started showing up in my life in that way. I didn't recognize it as mentoring at first. We just had lunch occasionally. He asked me good questions. He'd been a principal, a pastor, a school administrator. He'd seen more than me. He was direct without being harsh. And somewhere in the third or fourth year of those conversations, I realized: this is what I've been missing.

Harold died a few years later. I was more affected than I expected to be. And in the grief, something clarified: the thing he gave me, I wanted to give to someone else. Not because I have it figured out — I clearly don't — but because the absence of a good mentor is one of the most common and least-acknowledged sources of drift in the lives of people who are genuinely trying to grow.

What Most Mentoring Gets Wrong

The word "mentoring" has been so thoroughly institutionalized that it's lost much of its meaning. We use it to describe formal programs, assigned relationships, quarterly check-ins with people who aren't sure why they're meeting. That version of mentoring produces paperwork, not transformation.

Real mentoring is messier and more personal. It requires genuine affection — the mentor actually cares about the person, not the program. It requires honesty that sometimes stings. And it requires time — not big blocks of structured time, but consistent, unhurried presence over years.

Robert Clinton, who spent decades studying the life trajectories of Christian leaders, found that one of the key factors distinguishing those who finished well from those who didn't was the presence of significant mentoring relationships. Not one mentor — several, at different stages, offering different things. The leaders who flourished had people in their lives who knew them deeply and told them the truth.

The leaders who derailed often had plenty of admirers and very few people willing to say, "I'm worried about what I'm seeing in you right now."

The Two Directions

What I've come to believe — and what Harold modeled for me, though he never would have described it this way — is that we each need to be intentional in two directions simultaneously. We need to be actively receiving mentoring from those who are further along, and actively offering it to those who are earlier in the journey. Both relationships do something different to you.

Receiving mentoring keeps you humble and curious. It keeps the student alive in you. I try to have at least one person in my life who is ahead of me in some meaningful way — not just older, but further along in wisdom, in health, in the kind of person they've become. Their presence stretches me in a way nothing else does.

Offering mentoring keeps you honest. There's something about trying to help a younger person navigate the same mistakes you made that forces you to look at them clearly. You can't encourage someone toward self-awareness while hiding from your own blind spots — at least not for long. The person you're mentoring will see through you fast.

What I Try to Bring to the Mentoring Relationships I'm In

I meet regularly with a small number of people — mostly men in their thirties and forties who are navigating the questions I was stumbling through twenty years ago. Here's what I've found actually matters in those conversations:

Presence over performance. The goal isn't to impress them with how much I know or how well things turned out. The goal is to be genuinely curious about their situation — to ask questions that help them think more clearly, not to deliver wisdom I've already prepared.

Honest feedback, carefully delivered. This is the hardest part. Mentoring without honesty is just flattery with a spiritual coating. But honesty without relationship is just criticism. I try to earn the right to say the hard thing by being consistently present in the ordinary moments first.

My failure stories are as useful as my success stories. Maybe more. The times I got it wrong, the decisions I wish I could undo, the patterns I didn't recognize until they cost me — these are often more instructive than the wins. People don't need a highlight reel. They need a real person who's been where they're going.

I stay in my lane. I'm not their therapist. I'm not their boss. I'm not their pastor (unless I am, in which case that's its own thing). I try to be clear about what role I'm playing and what I can and can't offer. Good mentoring isn't trying to be everything to someone.

The Hole Harold Left

I still miss Harold. I think I always will. But one of the gifts he gave me — without ever saying this explicitly — was the understanding that the way you honor the people who invested in you is by paying it forward. Not as a transaction. Not as obligation. But because you know how much it mattered, and you've seen how rarely it happens, and you have something you can give.

If you're in a season of life where you have some experience, some scar tissue, and some capacity — I'd ask you to consider who might be waiting for someone like you. Not a perfect mentor. Not someone who has everything figured out. Just an honest presence. A person who shows up and asks good questions and doesn't walk away when things get complicated.

That's what Harold was for me. It's what I'm trying to be for the people in front of me now.

And it's one of the most meaningful things I do.

Is there someone in your life right now who's earlier in the journey than you are — someone who might benefit from what you know? What's stopping you from reaching out?