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Living Well

How to Avoid Regret Better Than 99% Of People

March 18, 2026

I’m Kim.
I’m an M.D.-turned-entrepreneur and I’m dedicated to helping you build your dream career + lifestyle. Welcome to my blog, where I write (and podcast) about wellness, business + success!
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Most people don’t end up with a life they regret because of one big mistake. Rather, it’s the thousand tiny moments when they chose comfort over courage.

And the scary part? Most of these choices happen without us even realizing it.

You see, our brain is constantly convincing us to choose comfort over growth. So we avoid risks and take the easy path, convinced that it’s the right decision. 

But then one day we look around and think, “How did I end up HERE?”

If you’ve ever worried that you might wake up one day filled with regret, read on. I’m breaking down where regret actually comes from, what happens when we choose comfort over risk, and how we can learn to say yes to what we truly want, even when it’s uncomfortable and scary. 


Understand Where Regret Actually Comes From

Studies on regret have found that people don’t regret the things they tried and failed at nearly as much as the things that they never tried at all.

What does this show us? 

That regret doesn’t come from failure. It comes from inaction.

Regret is an accumulation of all the times you:

  • Talked yourself out of an idea
  • Postponed something you wanted to do
  • Avoided a difficult conversation
  • Stayed silent when you wanted to speak up

But the problem with inaction is that it’s not always obvious. Inaction doesn’t feel like fear; it feels like being “reasonable” and responsible. For example, we want to start a new project, but we tell ourselves it’s not the right time or we don’t yet have the right skills.

We think we are being smart, but what we’re actually doing is setting ourselves up for regret.  

Comfort Isn’t Neutral

Inaction feels comfortable, but comfort isn’t neutral.

Choosing not to do something doesn’t keep you in the same spot; it actually moves you backwards.

Here’s why…

Every time you choose comfort, your brain learns that the way you handle discomfort is to avoid it.

And because your brain HATES discomfort, it rewards you every time you avoid it by taking away your anxiety and making you feel calm. 

So, when you don’t send that difficult email you’ve been pondering over, or when you don’t speak up about something, you get a wave of relaxation, which makes you think you did the right thing. 

But while relief feels great in the moment, it quietly trains you to shrink your life. 

Every time you choose relief over growth, even when it feels completely justifiable, you set yourself up for regret. And that’s exactly why comfort is not neutral.

Regret Is an Identity Problem (Not a Time Problem)

Many people tell themselves their regret is the result of not having enough time, or the right opportunity, or better circumstances.

Regret isn’t really about what you DIDN’T DO. It’s about who you didn’t become.

When you really dissect regret, you see that at its core, regret is the gap between:

  1. Who were you living as
  2. Who you knew (deep down) you were capable of becoming

And that shows us that regret isn’t a time problem but an identity issue.

If you don’t close that identity gap, you will keep waiting to take action, telling yourself you’re not ready. 

But the key to closing the gap is to take action anyway. Yes, even if you lack confidence, even if you’re not sure, even if you don’t feel ready.

Because when you act before you feel confident, you prove to your brain that you’re becoming the person you’re capable of becoming. Every time you choose growth over comfort, you create a new identity, one that aligns with the person you know deep down you can be.

But… every time you decide to wait, every time you tell yourself you’re not ready, every time you choose comfort over growth, you reinforce your old identity.

That’s why regret cuts so deeply. Because it’s not about the missed opportunity, it’s about the version of you that never got practiced into existence.

How To Avoid Regret (Without Taking Life-Changing Risks)

Now that you understand where regret comes from, why comfort isn’t neutral, and that regret is an identity issue, you might assume that to avoid regret, you need to do something massive, like quit your job or move countries.

That’s not the case at all. In fact, I’ve got two simple techniques you can use, which don’t require any dramatic action.

  1. Use Future Regret as a Compass

The first tool is one I use all the time, and it’s called the Future Regret Test.

When you’re standing at a fork in the road, trying to decide between something that feels comfortable and something that feels scary, ask yourself this:

If you were to take the option that feels scary, would future-you feel relieved or disappointed?

That question cuts through a lot of noise because it aligns you with the identity you’re working towards rather than your current self.

It reframes the usual question we ask ourselves, “Will this work?” into “Will I respect myself for this?”

I use this strategy all the time, such as when I’m debating whether to have a conversation I’d rather avoid or when I’m tempted to stay quiet instead of saying the thing that matters.

If I ask myself this question, and I know future-me would be disappointed, the answer is simple… I have to do the scary thing, even if I don’t feel ready.

Most growth decisions don’t come with guarantees. But avoiding regret doesn’t require certainty; it requires alignment. 

And most of the time, you already know the answer. You just have to ask the question.

  1. Make One Daily “Anti-Comfort” Choice

The second strategy I use is called the “anti-comfort choice.”

It’s about taking one small, daily act of courage — making one decision a day where you intentionally choose growth over relief.

Think about something small you normally avoid doing, like:

  • Turning off the show after one episode
  • Hitting publish instead of saving it as a draft
  • Choosing the workout when the couch is calling your name

What would happen if every day, you did one of these small things instead of avoiding them?

I’ll tell you what happens… You start to trust yourself again.

You start to see yourself as someone who follows through, someone who listens to that quiet nudge, and someone who doesn’t abandon themself when things feel inconvenient.

And when that identity starts to form, regret loses its power. 

You don’t avoid regret by being fearless. You avoid regret by being deliberate. By choosing growth just often enough that your life starts to move in the direction you actually care about.

Final Thoughts

In this week’s YouTube video, I dive deeper into these strategies and share my personal experiences with regret. 

Here’s where you can watch:


And if you’re ready to start making your life feel intentional again, I invite you to join The Reset. It’s a free, short, structured challenge designed to interrupt the default patterns that keep you choosing comfort when you actually want growth.

Resources:


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