A woodworker’s lesson about thinking ahead — and leading the same way.
There’s a lesson I learned in my workshop that has shaped the way I think about leadership: sometimes you can’t drill a hole after the project is assembled.
I learned this the hard way building a new workbench. I had a narrow opening where I wanted to install an adjustable shelf — the kind held up by shelf pins in a line of holes that let you set the shelf at different heights. Drilling those holes is simple work, especially with a dedicated jig. Unless, of course, you forget to drill them before assembling the unit, and then discover the narrow opening won’t fit a drill. That’s when you get to choose between two equally painful options: take the whole thing apart, or live with a shelf that doesn’t adjust.
When you build with wood, you have to think in three dimensions — and more importantly, you have to think ahead. Before your first cut, you need to know where every joint, every fastener, and every detail will land. Miss one step and you’re not just fixing a mistake; you’re dismantling everything you’ve built. Leadership works exactly the same way.
Linear Thinking Is a Trap
It feels natural to move in a straight line: finish step one, move to step two, deal with step three when you get there. But real leadership doesn’t work that way. The decisions and groundwork you’ll need at step four have to be set in motion back at step one — or you’ll find yourself tearing everything apart just to drill a hole you should have drilled at the start.
Hiring is a perfect example. You’re busy. You’re overwhelmed. Writing a job description feels like a luxury you can’t afford right now. So you tell yourself you’ll get to it when things settle down. But if you’re thinking in three dimensions, you can already see what’s coming: the moment things get busier — and they will — you’re going to desperately need someone in that role. The time to plan is now, not then.
Woodworkers Call It Mental Rehearsal. Leaders Call It Strategy.
Experienced craftspeople build their projects in their heads before they ever pick up a tool. They run through every step, visualize how the pieces fit, and catch problems before a single board is cut. They draw on experience without assuming that what worked on the last project will automatically work on this one. That mental rehearsal is the difference between a project that comes together cleanly and one that falls apart halfway through.
As a leader, making time to visualize the team and work you’re responsible for will tell you how the pieces fit together, what’s missing, and whether you have the right people in place. Sometimes this is as simple as scheduling uninterrupted time to think — to let your mind wander through the possibilities. Done regularly, it helps you find blind spots and recognize what needs to happen today to create success weeks or months from now.
When You Need to Get It Out of Your Head
Sometimes visualization alone isn’t enough. When I’m not confident enough to cut into that perfect piece of walnut, I make a sketch, or build a 3D CAD drawing. I get the project out of my head and let it live in the open where it can mature and grow.
In leadership, the equivalent is structured strategic planning such as a SWOT analysis — the strategic “CAD drawing” that maps how your strengths and weaknesses fit together, identifies gaps in your plan, and forces you to design contingencies before you need them. The risk, of course, is analysis paralysis: spending so much time fretting over the drawings that you drive yourself and your team to the edge of exhaustion before anything gets built. The goal of the analysis is to move toward clarity, not to chase certainty.
Sometimes You Just Need to Touch It
Even experienced woodworkers hit a point where the project won’t fully resolve in their heads. The joinery gets tricky. The dimensions seem off. At some point, you stop reworking the drawing and pull out a piece of scrap wood to test whether the pieces will fit the way you visualized — and whether the piece just feels right.
That’s not a failure of planning. That’s experimentation, and it’s a critical part of the process. The same is true in leadership. Sometimes you’ve done all the abstract thinking you can, and the only way forward is to prototype — test the idea with a small team, run a pilot, pressure-test your assumptions before you commit fully. The goal isn’t to have every answer before you begin. It’s to find the problems early, while they’re still cheap to fix.
So Where Is the Balance?
The best leaders I’ve encountered aren’t the ones with the perfect plan. They’re the ones who think far enough ahead to anticipate where the plan will break down — and prepare for it. They don’t over-engineer the risk analysis, but they don’t wait until they’re mid-project to realize they forgot to drill the hole either.
They think in three dimensions. They plan at step one for what they’ll need at step four. And they stay ready to shift when the plan meets reality.
Like woodworking, leadership is messy. There is no single right way to build something great. You can’t let the fear of mistakes keep you from moving forward. Create your best plan, keep your goal in sight, stay willing to pivot, and accept that the mess you make along the way isn’t a sign of failure — it’s a sign of growth.
(As a woodworker, I’ve learned to channel Bob Ross and call my mistakes Happy Little Accidents. How that mindset translates to leadership? That’s a story for another article.)
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