Let’s talk about regret, baby …

Let’s talk about all the good things and the bad things that may be … let’s talk about regret …

If you’re my age, plus or minus 5 years, the Salt n Pepa song is rolling though your head.

  • You’re welcome.

For the last seven weeks I have been experiencing what it means to be ‘semi-retired‘ at the age of 36.

The business I was working for as the HR Director shut it’s doors and I have found myself reinventing myself and leveraging my consulting and coaching skills in a very interesting market up here in the subarctic.

This has been one of the easier endings I have experienced in the past few years; yet it is still incredibly difficult to navigate. Glancing in the rearview mirror, it is easy to listen to the voice that apparently knows everything and is superior and haughty in their assessment of my work and what I should have done differently.

Enter a microcosm of regrets.

  • I should have never changed jobs.
  • Why didn’t I take bigger risks in the executive meetings?
  • If only I had stuck to my guns and didn’t back down …
  • What if I had died on that hill? Apparently it WAS worth dying on …
  • Why didn’t I spend more time growing my consulting business rather than thinking about work?!
  • Maybe I should have been more mouthy and less self-protective …

And this is only a snippet of my personal regrets … corporately, there are many more.

  • The idea that you can live a life without regrets is ridiculous.

Of course you are going to have regrets; the only way to not regret anything is to be dead. And even then I am not 100% certain regrets won’t find their way into our dreams while we take the giant dirt nap.

Regret is part of life; what you do with it is what matters.

Some of the most painful regrets are the ones which are a result of trying to avoid regret in the first place.

  • I call this the Regret Circle of Death.

Regret Circle of Death – Oh I can’t do that. I won’t do that … I might regret it. Or should I do it? I should have done it. Maybe I should do it now? Maybe not? If only I had done it then. Is it too late now? Maybe I still have time. Its too late. If only I had done it … but I thought I would regret it. Now I regret not doing it. SIGH. What now?



Next thing you know, five years have passed and you’re still not doing what you want to do because it carries with it the potential risk of hurt and regret. Suddenly you find yourself full of regrets about not living the life you wanted to live; not living your life in a way that is true to who you are.

I think somehow we learn who we really are and then live with that decision.
~ Eleanor Roosevelt

Don’t strive to live a life without regrets. Learn to deal.

Should of …
Could of …
Would of …
If only …

In order to not crash while navigating life, you need to spend most of your time looking out the windshield while only glancing in the rearview mirror every now and again.

  • After all, as human beings, we are made to go forward.


Regrets will haunt you unless you deal with them and learn from them. Either they are something which fill you with shame every time you glance in the rearview mirror or they become an important lesson which shapes you to be an incredible human being and able to live a full, big life.

When the painful endings in life come, instead of berating yourself, ask good questions.

  • What am I most proud of?
  • What would I do different next time?
  • Who am I now?
  • Where didn’t I show up? Why?
  • Where did I hold back?
  • What would I do again? Not do again?
  • What hurts? Why?
  • What do I want now?
  • Where to from here?

Accept the fact that you will have regrets – just make them worthwhile and choose to risk regret by loving, living and losing.

And when you lose, lose well by learning from the regrets which haunt your dreams so you can start dreaming about an amazing future once again.

When dealt with, regret can become an intimate teacher which reveals things to you about yourself and the world, helping you expand and grow to be able to do and be more. Accepting and learning from regret gives you the ability to not fear living a full life and reminds you of how far you’ve come and what you’re capable of.

Moving through regret has taught me that showing up, grabbing onto life every single day, giving what and who is in front of me my whole heart and being fully present where I am is always worth it.

  • And it has taught me to dance, even when life continually rains on me.
If it is raining, put on the rain coat and get out there. There is life to be lived!

If it continually rains, put the raincoat on and get out there and dance even if you look ridiculous. There is life to be lived!

How has moving through regret taught you to live a better life?

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