When Sensible Decisions Become Expensive

One of the phrases I hear most often in conversations with people building businesses is:

“I wish we’d had this conversation earlier.”

It’s a comment that has stayed with me because it almost always comes at the same point. Not when a business is struggling, but when it’s succeeding.

The decisions that helped the business survive are beginning to shape what success looks like.

That isn’t because anyone made a bad decision. Quite the opposite. Most of the time they were making the best decision they could with the information, resources and time they had available.

There wasn’t enough money to pay everyone helping to build the business, so a software developer was offered a share of future value instead of a full commercial fee. An accountant suggested bringing family members into the shareholding because it seemed like a sensible and tax-efficient thing to do. A customer offered the security of a long-term commitment but wanted a say in how the product or service would develop.

None of those decisions are unusual. In fact, most are entirely understandable.

When you’re trying to win customers, build a product and make payroll, thinking five years ahead can feel like a luxury. Survival has a way of dominating almost every decision.

That’s why one of the hardest parts of my work is asking tomorrow’s questions when today’s pressures are demanding almost all of someone’s attention. Not because people don’t care about the future, but because the pressures they’re dealing with today are completely real.

Over the years I’ve come to realise that some decisions don’t simply solve today’s problem. They quietly shape tomorrow’s options.

Sometimes that means a little more cost and complexity later on. Occasionally it’s much more significant and makes an investment, a partnership or even the sale of the business much harder than it needed to be. Not because the business isn’t valuable, but because decisions made under the pressure of survival have become difficult to revisit once success has arrived.

The conversations people remember aren’t usually the ones where somebody gave them a brilliant answer. They’re the ones where somebody asked a question that changed the way they looked at the decision they were about to make.

“If this works, will this arrangement still make sense?”

“If this relationship changes, what happens next?”

“How might this look to someone approaching it from a completely different perspective?”

Those questions rarely produce immediate answers. What they do create is a little more space to think while there are still choices to make.

That’s why I love conversations with people who’ve built a business that’s gone beyond the survival perspective. Not because they’ve discovered a secret formula, or because experience somehow makes them better than everyone else. It’s simply that they’ve seen which decisions have a habit of becoming important later.

The encouraging lesson I’ve learned that you don’t need twenty years of experience to benefit from that perspective.

You don’t need to think about everything, and you certainly don’t need to anticipate every possible future. But there are a handful of decisions that are worth slowing down for because, if survival turns into success, they’re much harder to revisit.

My favourite conversations end with someone saying:

“I’m so glad we thought about that when we did.”

For me, that’s usually the sign that the conversation happened at exactly the right time.