The Hidden Cost of Playing It Safe

Why fear of regret, not failure, is the real threat to your future

During COVID, one of my closest friends was laid off.

Two kids. A mortgage. A wife. Gone. The company he worked for had been doing well. Big brand, stable paycheck, loyal staff. Until it wasn’t.

We supported him financially for months. Because that’s what friends do. But it changed something in me.

At the same time, I was working in the medicolegal world, managing rehab for people with catastrophic injuries. That job relied entirely on contracts with insurers and solicitors. And when one major contract was lost? Good people were let go. No warning. No ceremony.

I kept my seat because I was a high fee earner. But the message was loud and clear:

The “safe” path isn’t safe. It’s fragile.

I wasn’t panicked. I was numb.

There was no crisis, just a quiet, gnawing boredom. I was trading time for money and building someone else’s dream. Lining their pockets, not mine.

Worse, I was missing out on life. Time with my son was always rushed. Chores, errands, distractions. My mind never stopped. I was consumed by work tasks, bills, and noise.

No space to think. No margin to create. Just fog.

I used to be described as "the funny one." That faded. I became irritable, joyless. People started walking on eggshells around me. I noticed.

So did my family.

Anxiety showed up in my body. Tight gums. Poor sleep. Short fuse. But I pushed through. Because that’s what we’re taught, right? Just keep grinding.

Until I couldn’t anymore.

My marriage, on paper, was perfect. My wife was a successful doctor. We had a nice house, good holidays, stability. But I knew deep down we were misaligned. I had dreams. She had her own. I felt like the admin assistant to someone else’s vision.

I stayed too long. In my marriage. In my job. In a version of life that looked good but felt wrong.

I’ve always feared failure. It’s what kept me stuck.

But eventually, regret started to scare me more.

The Realisation That Changed My Life

I realised: if I don’t want my life to look like theirs, why am I letting their opinions hold me back? That voice in my head, fear of being judged, misunderstood, seen as selfish, wasn’t mine. It belonged to people who didn’t understand the life I wanted to build.

And if I let that voice control me?

They owned my life. Not me.

It took me 36 years to make the switch. To choose myself. To accept that discomfort now is better than regret later.

Dan Pink’s research backs this up. Our deepest regrets aren’t from what we tried and failed, but from what we never had the courage to try.

I knew that if I stayed where I was, I’d spend the next decade with a slow-burning ache, wondering what if.

Failure Taught Me This

I’ve failed before. In my 20s, I launched a female-focused supplement company. I was naive. No strategy. No support. But I did it. And it showed me that I could create something from nothing. I just needed better tools next time.

Failure taught me. Regret would have crushed me.

The shift didn’t start with quitting my job or launching a business.

It started with one honest conversation with myself.

Then another with the people who loved me.

I was scared. I felt guilty. Especially for my son. But I knew I couldn’t keep pretending. Not for another year. Not for one more Sunday filled with dread.

So I walked.

I got divorced. I went solo in my work. I started writing online, building a personal brand, sharing what I knew. My thoughts. My values. My lessons.

And I realised I wasn’t alone.

People resonated. They replied. They hired me. My income doubled. My hours halved. And most importantly, I got my life back.

That first small move, just speaking my truth, gave me back control.

It was freeing. Powerful. Peaceful. Like I finally stepped into who I was always meant to be.

Today, I don’t fear failure.

I fear going back to the man I was before. Stressed. Stuck. Misaligned. Shrinking.

Now I live with clarity. Direction. Autonomy.

I know what I want.
Freedom of time.
Freedom of choice.
Freedom of finances.
A personal brand that lets me serve others, on my terms.

And I know who I want to be.
A present father.
A thought leader.
A builder of real, leveraged freedom.

If you’re still stuck in the loop, waking up tired, walking through days that feel dull, staying in the “safe” seat...

Ask Yourself This

What scares you more — failing, or regretting that you never tried?

Because failure is temporary. You’ll learn. You’ll grow. You’ll come back stronger.

But regret?
Regret is quiet.
It hides.
And then one day, it roars.

Don’t let that be your story.

You already have the skills. The resourcefulness. The desire. You’re not too late.

But you might be too comfortable.

And that comfort has a cost.

Your turn.

Answer This To Change

What regret will you carry if nothing changes?
And what truth do you need to speak to start your next chapter?

Unitl next time,

David