This is a Tough Pill to Swallow

Estimated reading time: 3 minutes, 50 seconds

Failure stings, but it passes.

On the other hand, regret lingers, because you will never know what could have been.

Better to try and fall than to never leap at all.

Here’s an illustration to help you understand this principle more:

The pain of failure can be a tough pill to swallow, but it is nothing in comparison to the discomfort you will experience from regret.

Neither is pleasant, but one of them will stay with you forever.

I know which I’d rather. Do you?

Regret is the long burn — the ache of what if?

Failure might bruise your ego, but regret bruises your spirit.

You can recover from falling, but you can’t recover the moment you didn’t take.

It’s easy to fear failure — the sting of messing up, being seen slipping up, or the disappointment of falling short.

So we wait. We hesitate. We stall.

But here’s the truth: failure hurts less than regret.

Failure gives you feedback. It teaches you. It moves you forward.

Regret just lingers. It’s the pain of not knowing, the ache of wondering what could have been.

Courage isn’t about confidence — it’s about choosing growth over comfort.

You don’t have to be fearless. You just have to be willing.

Here are 3 ways to choose action over avoidance:

1. Shrink the Risk.
   You don’t have to go all in.
   A small step is still a step.
   Tiny attempts beat endless planning.

2. Focus on the Cost of Not Acting.

   Instead of asking, “What if I fail?” try asking, “What will I miss if I don’t even try?”

   Regret often comes from staying safe, not from falling short.

3. Redefine what success means.

   I share this idea regularly, and that’s largely because society’s definition of success is often wrong.

   Trying is succeeding.

   When you focus on progress over perfection, failure becomes part of the reward.

Let’s dive deeper into today’s wisdom with these 3 journal prompts:

• What’s something I’ve been putting off because I’m afraid to fail?

• What would I lose if I never tried?

• What would I gain simply from giving it an honest shot?

Want to learn more about journaling? Join Journal Wiser today!

This conversation between then aspiring writer Jenny Wood and NYT Bestselling author Dan Pink explores what people regret most and how understanding our regrets can help us live more boldly and wisely.

A powerful reminder that it’s not our failures we remember most… it’s our inactions.

You can enjoy this conversation here:

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Catch you in the next issue!

Thanks,
Michael