Let’s get a pretty ginormous stat out in the open, straight away:
When asked the question “How often do you look back on your life and wish you had done things differently?”, 82.4% of survey respondents indicated they’d like some kind of do-over. That’s a lot of regret in the system, isn’t it?
Here is my doodle of the survey results, because I know how much you like stats:

And here is a chart because I know how much you like nachos:

I just visited my dad for his 89th birthday (I’ll pass on your belated HB message; thank you), and at some point our chat turned to our respective careers. Our conversations these days more often have to do with the ins and outs of his catheter (hahaha—get it?—ins and outs?), so this girl perked up at the promise of body-part-free banter.
He asked this great question: “If you could go back and do any part of your career over again, would you do anything differently?”
I am generally a “wouldn’t change a thing” kind of person. I believe that shit sandwiches have a place on the buffet table of life—mostly because they steer us towards better choices into the future. “Improved decision hygiene” is the chief benefit of regrets (I am going to obnoxiously quote myself from my book here): “Regrets can spiff up our future decisions because of the ‘once bitten, twice shy’ effect; being burned from a previous regret slows us down and broadens our perspectives, so we don’t make the same mistake twice.”
And yet.
It took me a minute but I had an answer for my dad. I didn’t regret any of the choices I made; I regret that it took me so long to take action on the decisions I had made along the way.
I stayed in my Fancy Corporate job for a full three years (156 Mondays, *sigh*) after I knew I wanted something different. But that was okay. I was learning a lesson. I was learning to “jump and the net will appear” and all that jazz. (For the record there was no net. I just had to be okay with starting over from where I splatted on the pavement, and thankfully it was totally worth it in the end.)

The Scrunchy Face of Learning a Lesson Again and Again.
I have had three big career conundrums since then and you can’t see me but I am making a scrunchy face about how I didn’t take swift action on the decisions I knew I needed to make.
For example, I had been executive coaching for ten plus years, and I wasn’t feeling it anymore. I kept telling myself I was going to stop doing it—focus only on speaking and writing—but you know what I did? A whole lot of coaching. It was eerily reminiscent of how I found myself stuck ten years prior, except I was my own boss this time. It took me at least a year to go from “I don’t think I want to do this coaching thing anymore” to no longer offering it as a service (except sometimes for one friend I love and if you’re reading this, hi N!).
So that I regret—not moving on faster.
What sorts of things would you do over if you had a chance to do so—in and out of your career? Some things might still sting. You might regret having embezzled from your company and serving all that time in prison, for example. I bet you’re making that scrunchy face right now.
Most of us have an opportunity to learn from the coulda, shoulda, woulda do-overs, though. Realizing I tend to linger too long helps me look a little clearer in the mirror. I’m now asking myself, “is there anything I’m dilly-dallying when I’ve already made the decision I’m going to move on anyways?” This little pre-gret exercise helps me live better, knowing I don’t want to make the same mistakes again.
Maybe your do-over would be that you’d have been bolder with your assertions at work. Well good news Sweet Cheeks, you’re not dead yet and you still have a chance to be bold—starting this afternoon.
Maybe your do-over would be that you’d have pursued the career you’d always dreamt of rather than joining the family business. Guess what? Colleges accept applications from people of all ages.
Maybe your do-over would be that you’d have been a little less competitive and more collegial in your job. Well, phew (for you and them)—you can start acting like the kind of colleague people don’t complain to their spouses about.
Maybe your do-over would be that you’d have spent more time with your kids instead of your laptop. You know where this is going.
I could give you more examples but let’s be honest: you get the point and I would just regret making this article even longer. Ask yourself the question my dear dad asked me and start using the intel to shape your Mondays moving forward.
Now let’s go get some nachos?

P.S.: I can guarantee you won’t want a do-over after reading my book, You Only Die Once: How to Make It to the End with No Regrets!
P.P.S.: Let’s connect on Instagram!
P.P.P.S.: Oh and just in case you missed it… I’d love you forever if you took 16 minutes out of your life to watch my TEDx talk!





