Why We Miss the Summit

I was thinking about a backcountry trip last season — a small group of us skinning up to a bowl we’d heard was worth the climb. It had snowed the night before, so we were motivated.

We had maps. We had a GPS. We had a plan.

We still got it wrong.

Somewhere on the way up we drifted off our intended line. By the time we figured it out we’d already put in a significant climb, and backtracking cost us the bowl entirely. We ended up somewhere decent — but not where we were trying to go.

Here’s the thing: the information we needed was available the whole time. The terrain was right there. We just couldn’t see it properly from where we were standing. Head down, working hard, making reasonable decisions with what was in front of us.

It wasn’t until we got to higher ground that we could see exactly where we’d gone wrong — and how obvious the right line would have been from up there.

I think about that day a lot when I’m sitting across from a founder.

Most of the founders I work with are exceptional at running their businesses. They make good decisions under pressure, they manage complexity, they know how to execute.

But when it comes to their personal financial picture, most of them are doing the same thing we did on that skin track — head down, working hard, making reasonable decisions with whatever’s in front of them.

They’ve got a lawyer who set up their corporation. An accountant who files their returns. Maybe a banker, an insurance advisor, an investment person they ended up with somewhere along the way. Everyone is doing their job.

But nobody is looking at the whole terrain.

The lawyer built the structure for where the business was at the time. The accountant is focused on compliance and this year’s tax bill. The investment person is managing the portfolio. Nobody is standing at the top of the ridge asking: given where this person is actually going, is any of this set up right?

That’s the gap. And it’s more expensive than most people realize — not because anyone is doing anything wrong, but because good work in isolation isn’t the same as good work coordinated.

Not who is doing each piece of it. Who is looking at the whole map — your business structure, your personal finances, your tax exposure, your estate, your plans for what comes next — and making sure the pieces are talking to each other?

If the honest answer is “me, when I have time” — that’s worth paying attention to.