July 28, 2026
3
 minute read

The Way You've Always Done It

A golf bag and trolley beside the course, representing familiar habits that keep going because they have always been there
Written by
Jeremy Askew

Every golf club has a member with a swing like a deckchair collapsing. It works, more or less. It's worked for thirty years. The pro could sort it in three lessons, and everyone knows it, including the member. He's never had the lessons. Three weeks of getting worse before getting better is a price he won't pay, not for a lifetime of better golf, not for anything. The swing stays. It's his.

Nobody decides to keep a flaw. They just keep playing the way they've always played.

Money runs on the same sentence. The savings account opened in another decade, still holding serious cash because it's “safe.” The pension from two jobs ago, never once looked at. The insurance renewed each year out of pure momentum. The investment approach inherited from a parent whose world had different rules. Ask why, and the answer is nearly always some version of: this is the way I've always done it.

It sounds like a reason. It's actually just a history.

In business, that sentence is famous as a death knell. Companies die of it all the time, comfortably, right up to the end. The personal finance version is slower and more private. No bill ever arrives for default thinking. The cost turns up as things that quietly didn't happen. Growth you didn't get. Cover that stopped fitting years ago. Nobody sends a statement for those.

Here's what I'd say the fix is not. It's not becoming a maverick. Whatever the posters say, you don't need to think different. Most people who set out to think differently about money end up poorer and interesting. You need something much smaller. One question, asked every so often, about each thing you do: knowing what I know now, would I choose this today?

Most things survive the question. That's fine. The point was never change for its own sake. The point is that “I chose this” and “I've always done this” feel identical from the inside, and only one of them is a decision.

The member with the deckchair swing shot 92 on Saturday. Perfectly content. And honestly, that's allowed. He knows what the swing costs him and he's decided to pay it.