June 26, 2026
3
 minute read

Hand On The Tiller

A small boat resting on misty water, with trees fading into the fog nearby
Written by
Jeremy Askew

We can't know what comes next. That's not a gap in the plan. It's the condition the plan has to live in.

What I do know is that whatever we put together will get buffeted. Day to day, week to week, month to month. Something always blows in. So the plan can't be a straight line drawn in calm water. It has to be built to take weather.

That means sensible assumptions. Margins. A bit of leeway for the things we know we don't know, and a bit more for the things we don't even know to worry about yet. Sorting one from the other is most of the skill, and it's closer to an art than a science.

People tell me things they believe are certain. Interest rates are definitely going up. I tend to say: we don't know. We almost never do. The honest truth is we know a great deal less than we think we do, and a plan that pretends otherwise is the fragile kind.

Sailing is the picture I keep coming back to. In a strong wind you don't hold the sails rigid. You trim them. You adjust to the conditions you've actually got, not the ones you forecast. The plan works the same way. It bends with the weather instead of snapping in it.

And here's the part that matters most when it's blowing hard. We keep our hand on the tiller. We know roughly where we're heading. We're ready to change tack when the weather shifts, whether it's against us or with us.

What we don't do is jump overboard. When it's rough, the strongest urge is to abandon the boat. Sell everything, go to cash, wait on the shore until it looks calmer. But the boat is the only thing with any chance of getting you to the other side. Leaping into the water in a storm has never once been the safe option, however much it feels like it in the moment.

Most of what unsettles people in those moments isn't the weather itself. It's what they're telling themselves about it. We can't flatten the sea. We can help with the thinking, keep a steady hand on the tiller, and hold the course that was always the point.

We'll be buffeted. That was always going to happen. Staying in the boat is the whole job.