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5 Things You Will Never Regret

Dec 24, 2023

Read Time: 4.5 minutes

Many people struggle with regret in varying degrees, and depending on how severe the incidents are, this feeling can linger much longer than expected or we would prefer. Of course, we all cope with guilt or blame in different ways.

Growing up, my dad often shared simple yet powerful statements with my brother and I. Here’s a good one:

“Guilt will take you further than you want to go. Keep you longer than you want to stay and cost you more than you want to pay.”

And it is because of this teaching that I believe regret is not only conquerable but also avoidable.

Thanks dad!

So, in today’s issue of the Clarity Club, I want to share five things you will never regret.

But before I do, it’s best to first talk about the one question we’re all asking ourselves.

How do I deal with the regret(s) I already have?

I’m curious if you’ve had a conversation with yourself before that’s similar to the following.

If so, raise your hand to yourself or hit reply and let me know.

That conversation may have gone something like this:

“How do I stop regretting my past decisions? I can’t stop thinking about how my life could have been if only I did XYZ things… or if I wouldn’t have done this or that.”

You see, our insecurities can stop us from doing what we want. And to add fuel to the fire, those same insecurities can cloud our judgment and guide us to knowingly or unknowingly make decisions that we will later regret.

But the good news is that:

  • You’re not alone if this is how you feel
  • Moving past previous regrets is doable with the right strategy

Consider this short checklist.

✓ Let yourself feel it — when experiencing any regret, it’s tempting to squish down the feeling or dismiss it altogether. Doing so can make things worse. Instead, acknowledge your feelings and look for common triggers that dig up those memories. Make note of What, When, Where, and How.

You can then use this knowledge to become more aware of these triggers as they occur or before they happen and immediately begin to reshape your thinking around those regrets.

Like any life skill, this will take practice, but with perseverance, you’ll soon be a pro.

(Consider integrating this into your journaling routine if you have one)

✓ Draw something positive from the experience — in many cases, regret can hold one or many valuable lessons for us to learn. Using the new skill you picked up from the first point I mentioned, start observing your feelings and extract the lesson(s) from it.

✓ Try to avoid what-ifs — it’s tempting to run through all the possibilities and alternative outcomes in your head. I get it! I’ve done it. But it can get exhausting very quickly.

Again, using the new skill you picked up from above, take a step back and try to recognize when you’re engaging in thought patterns that aren’t productive or helpful.

Here’s a great question to ask yourself:

“Is this thought helping me or hurting me?”

More than likely, it’s the latter. So it’s in our best interest not to go down that rabbit hole.

How to avoid regret

I can’t talk about moving past regret without quickly touching on how to avoid it altogether.

After all, at the beginning of this email, I confidently stated, “I believe regret is not only conquerable but avoidable.”

So here it goes.

Avoiding regret begins with implementing a better decision-making process. Something that is easily repeatable, reliable, and flexible enough to adjust to any decision we’re making regardless of the circumstances.

My decision-making process consists of seven simple steps.

  • Values
  • Impact
  • Effort
  • Gut Check
  • Knowledge Check
  • Vision
  • Score

Each step is an additional layer/filter to push my decisions through.

This process doesn’t make the final decision for me, but it creates a map guiding me toward my best decision.

I used this to help me finalize my decision to quit my corporate job, and I also used it to help me declutter with more confidence.

You can steal my decision-making process here.

I also wrote up an entire article detailing each step. Please give it a read for more context.

But at the very least, I challenge you to develop a better decision-making process so you won’t regret it later.

5 things you will never regret

Alright, now let’s get to the meat of what this issue of the Clarity Club is about.

Here are five things you will never regret.

  1. Decluttering the excess in your life
  2. Gaining clarity
  3. Prioritizing your core values
  4. Pursuing a meaningful career
  5. Taking a step back to celebrate who you’ve become and the life you created

Your next steps

Build your system for conquering existing regrets and avoiding any potential future regrets. Think about the steps you need to take to reshape non-helpful thought patterns and make confident decisions effectively.

Once you have that system in place, don’t divert from it. It’s a lot harder than you think, and because you’re human, it can be tempting to revert to what’s already familiar. But it’s worth it to create the habit.

You’ll be glad you did.



Whenever you’re ready, here’s how I can help you:

 The Decluttering Starter Kit: Skip the overwhelm and jumpstart your decluttering journey. This comprehensive course will teach and guide you through my multi-step action plan for decluttering with less overwhelm and more progress each week. Get access here.

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