Let me start with a quick story from my childhood.

I had a plastic rugby ball that I was rarely without. In my mind I was destined to be an All Black (New Zealand's national rugby team) obviously.

One afternoon I was meant to be helping take washing off the line. Instead I was out the back practising my drop kicks. One particularly glorious kick sailed beautifully through the air and straight through the kitchen window.

Glass everywhere.

Two weeks later it happened again.

Same washing line. Same rugby ball. Same recently replaced window. My stepfather happened to be walking past at the exact moment the ball smashed through for the second time. He used to call me the Boy Wonder not just because Batman was my favourite TV show but also because I never ceased to amaze him.

So why bring up this childhood memory?

Because it’s a perfect example of something that trips up a lot of smart people, especially when it comes to careers.

The sunk cost fallacy.

Here’s how the sunk cost fallacy usually shows up in real life.

Someone is thinking about making a change. Maybe a career pivot. Maybe starting something new. Maybe leaving a role that no longer excites them.

But then the internal voice kicks in.

"I’ve spent twenty years building this expertise."

"I can’t just throw all that away."

"I’ve invested too much to start again."

Sound familiar?

The problem is that sunk costs are exactly that. Sunk. Gone. Already spent. Time, energy and effort that you cannot recover.

Yet we keep making decisions as if we can somehow claw it back by staying the course.

Most people ask the wrong question.

They ask:

“Have I already invested too much to quit?”

The better question is this:

“If I was starting today, knowing what I know now, would I choose this path again?”

If the answer is no, that’s worth paying attention to.

Write down the main thing you feel stuck in right now. A job, a project, a direction you’ve been following.

Then ask yourself one simple question.

If this opportunity appeared today, with zero history attached, would I choose it?

Be brutally honest.

This is especially powerful for people in midlife.

By this stage you’ve usually built real expertise. You’re competent. You’re known for something. Walking away can feel irresponsible.

But here’s the twist.

Your skills rarely disappear. They transfer.

Communication skills transfer. Leadership transfers. Problem solving transfers. Industry knowledge transfers in surprising ways.

You are not starting from zero. You’re starting from experience.

And that is a very different thing.

There’s also a flip side to this.

Sometimes people assume they must learn every possible new skill before moving forward.

PowerPoint mastery. Excel wizardry. Coding. Marketing automation. Graphic design.

You can lose months trying to become competent at everything.

And often it’s completely unnecessary.

Look at the new direction you’re considering and ask:

Which skills genuinely unlock opportunity?

Which skills are just nice to have?

Focus your time only on the first group.

Ignore the rest for now.

One of the most useful ideas I’ve come across is the concept of Who Not How.

Instead of asking how you personally learn every skill required, you ask who already does that brilliantly.

Accountants exist for a reason. Designers exist for a reason. Virtual assistants exist for a reason.

Your time is finite.

Spending six months learning something you’ll only use occasionally might not be the smartest move.

Looking back, the lesson from my childhood rugby career is pretty obvious.

Just because you’ve already kicked the ball once doesn’t mean you should keep aiming at the same window.

Sometimes the smartest move is to stop, reassess, and aim somewhere completely different.

And if you’re reading this while quietly wondering whether it might be time to shift gears in your own life, take that feeling seriously.

Your past effort built the person you are today.

But it does not have to dictate where you go next.