Use The Fear Of Regret To Make Better Career Decisions

Readtime: 3 minutes

Most people’s biggest fear is fear of failure.

And most people’s biggest regret is missed opportunity.

But fear of failure directly causes missed opportunity.

In today’s newsletter, I set out how to avoid this trap.

Fear of failure

Worrying about failing at something is normal. It’s our brain’s way of keeping us safe.

But fear of failure often stops us from doing things we might love.

Or from building what could be a better life.

It means we often make poor decisions.

It causes us to miss out.

It means we settle.

However, by shifting our focus to the fear of regret, we can overcome the paralysis caused by fear of failure.

The fear of regret

When we look back, what really bothers us isn't when we tried and failed, it's the chances we didn’t take.

When deciding to do or not to do something, it can be helpful to imagine a time in the future where both main options have played out.

For example, the status quo scenario when we decided not to do something, and the scenario where we did something and it turned out positively.

We can imagine how we would feel in each scenario.

If we feel regret at the opportunity not taken, that is a good sign that perhaps we should say yes to it.

The lessor known Icarus story

You’re probably familiar with the Icarus story where Icarus flew too close to the sun with his wings made of feathers and wax. The sun melted his wings, causing him to fall into the sea and drown.

The moral of the story is about not overreaching.

I only recently heard about the other part of the Icarus story, where Icarus’s father also told him not to fly too close to the sea, as the dampness would weigh down the wings.

The moral of this part of the story is to not set your sights too low.

Striking the right balance between ambition and caution is essential when setting our career goals.

Unfulfilled ambition at work

You may be familiar with these views about work:

  • When people are dying they don’t normally say they wish they had spent more time at work.

  • In twenty years the only people who will remember that you worked late are your children.

I don’t disagree with these, but they’re not the full story.

Because unfulfilled ambition can be as disappointing as looking back and thinking we’ve worked too hard.

Yes, it’s easy to play it safe. But when we set our sights too low, we’re also guaranteed to not reach our full potential.

My view is that if we’re after happiness and fulfilment at work, we need some relatively big ambitions. And to achieve those, we’re going to have to work quite hard.

This doesn’t necessarily mean long hours, but it does mean ensuring our working hours are actually contributing to our ambitions.

And we can use the fear of regret to help us go for those bigger ambitions.

That’s it!

In summary

Congratulations, you now know how to use the fear of regret to set your ambitions:

  1. Reflect on the future: Consider how future you will view today’s decisions. Will you regret not taking more significant risks?

  2. Adjust your goals: If your goals feel too modest, it’s time to aim higher. Challenge yourself – you only progress when you step out of your comfort zone.

  3. Find your own balance: Like Icarus, maybe there is a middle path that is right for you. Not aiming too high to risk everything recklessly, but also not aiming so low that you sell yourself short.

On a personal note

It took me two years to decide to leave KPMG to build an executive coaching and professional development business. My main fear was around what I was giving up from a financial perspective. But when I thought about the decision in terms of missed opportunity, rather than fear of failure, the decision was easy.

I decided that I didn’t want to be in a situation in 10 / 15 years’ time where I regretted not having had a go at doing this. And I’m now very confident that I’ve made a great decision.

But, importantly, even if things weren’t going so well, the decision at the time would still have been the right one, i.e. to not live a life of fear and regret.

One quote to get you going

Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbour. Catch the trade winds in your sails. Explore. Dream. Discover.
— Mark Twain

What’s your take on this? Let us know here.

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