Playing It Safe Doesn’t Protect You From Failure

You can fail at something you never wanted in the first place. So why not give yourself a chance to succeed at something you truly believe in?

31 August 2026 - Last updated: 2 September 2026 -

If failure is possible either way, why not fail doing something you love?

“You can fail at what you don’t want, so you might as well take a chance on doing what you love.”

Jim Carrey learned that lesson from his father.

His father could have been a great comedian. He was talented, funny and creative.

But instead of chasing that dream, he chose what seemed like the safer path.

He became an accountant.

Then, when Jim was 12 years old, he watched his father lose that job anyway.

That story has always stayed with me.

Because it exposes one of the biggest illusions we have in life and in business:

That playing it safe somehow protects us from failure.

It doesn’t.

You can choose the secure job and still lose it.

You can choose the conservative business strategy and still fail.

You can avoid taking risks.

Avoid posting.

Avoid starting the company.

Avoid making the call.

Avoid changing direction.

And still end up disappointed.

So if failure is possible either way…

Why not at least give yourself a chance to succeed at something you actually want?

Of course, you need responsibility, discipline and a plan.

Especially when other people depend on you.

But there’s a difference between being responsible and spending your entire life being afraid.

Build something you believe in.

Do work you genuinely care about.

Take the shot.

Because failing while chasing someone else’s definition of security might just be the biggest risk of all.

Show me the magic in real life 🪄

More cases

View all cases