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Let Them Struggle a Little

2 minutes ago
3 min read

I don't remember my dad making everything easy for me.


I remember him teaching me.


There’s a difference.


Whether we were hunting, fishing, working with our hands, or figuring something out outdoors, Dad would show me enough to get started and then expect me to do something with what he had taught me.


Sometimes that meant struggling with it for a while.


Later, the Army reinforced that lesson in a much more demanding environment. Training wasn't designed to make you comfortable. It was designed to prepare you for the moment when someone wouldn't be standing beside you telling you what to do.


You learned. You practiced. You struggled. You adjusted.


Eventually, you became capable.


I've been thinking about that because one of the hardest things for an experienced leader to do is watch someone struggle with something you already know how to do.


You see the answer. You know the shortcut. You could probably solve the problem in five minutes.


And everything in you wants to jump in.


Sometimes we should.


But sometimes we need to let them struggle a little.


Don't Steal the Struggle


I'm not talking about abandoning people or allowing preventable failures with serious consequences.


I'm talking about productive struggle—the kind that happens when someone is stretching beyond what they already know how to do.


I've caught myself stepping in too quickly.


Someone is wrestling with a decision, a difficult conversation, or a project. I can see them struggling, and because I want them to succeed, my instinct is to help.


But I'm trying to ask myself:


Am I helping them—or am I taking the learning away from them?


Sometimes what looks like good leadership is actually rescuing.


The problem gets solved. Everyone moves on.

But who grew?


If I took over, I got another repetition at solving a problem I already knew how to solve.


They didn't.


There's a quote often attributed to Henry Ford:


“Failure is simply the opportunity to begin again, this time more intelligently.”


We shouldn't manufacture failure for people. But we shouldn't eliminate every opportunity for them to wrestle with something, make a manageable mistake, adjust, and try again.


If we remove every obstacle from someone's path, we may make their journey easier. We probably haven't made them stronger.


Know When to Step In


Leadership still requires judgment.


Safety, ethics, legal requirements, significant financial exposure, and someone's well-being aren't places to experiment with failure.


But plenty of everyday situations aren't catastrophic.


A presentation could have been better. A meeting could have been handled differently. A project needs revision. A decision wasn't the one I would have made.


Those moments may not require rescue.


They may require reflection.


“What happened?”


“What would you do differently?”


And most importantly:


“What did you learn?”


James 1:2–4 reminds us that trials produce perseverance and that perseverance develops maturity.


Difficulty can produce something.


When I look back at my own life, some of my greatest lessons didn't come when someone handed me the answer. They came when I had to work through uncertainty, make a decision, get something wrong, adjust, and keep going.


I wouldn't want to remove those experiences from my story.


So I need to be careful about removing them from someone else's.


A Question for Leaders


The next time someone on your team is struggling, ask yourself:


Do they need my intervention—or my confidence in them?


Maybe they need guidance.


Maybe they need another question.


Maybe they need a guardrail.


Or maybe they just need to hear:


“You've got this. Keep working through it.”


Then give them some room.


Be close enough to help, but far enough away that the accomplishment belongs to them.


Because eventually, leadership development should produce someone who doesn't need you standing beside them.


Sometimes helping people grow means resisting our instinct to rescue them.


Don't steal the struggle that might make them stronger.


Don't just solve the problem. Grow the person.


Go Be The Reason.


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Core Values

 

Five values shape every engagement, every piece of writing, and every trail. They are not aspirational—they are inherited.

​

  • Hard Work. Effort is not optional. The work gets done because it is worth doing, not because it is easy.

  • Authenticity. Leaders are most credible when they show up as themselves—imperfections, convictions, and all.

  • Integrity. What we say in the boardroom, on the trail, and at home is the same. Reputation is built one quiet decision at a time.

  • Service. Service to God, to family, to country, and to those in need. Every engagement is measured by whether it lifts the people the client serves.

  • Wisdom from Both Worlds. The clarity of the boardroom and the grit of the backroads are not in tension. The best leaders carry both.

 

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