Regret Not Required – Weekly Letters

This letter is dedicated to my friend Scott who lost his Mom this week. Her last words? “Too soon.” I can’t shake this feeling and it inspired my letter this week. Here it goes.

You’re in a car on your way to heaven. Your life ends in 30 minutes. What would you regret not doing? What would you regret not saying? Who do you want to talk to?

Don’t tell me. Write it down. It’s a prompt for journaling, but it’s a prompt for a reality check, too. Face it. You won’t get 30 minutes to process and ponder at the end, knowing everything is wrapping up. You won’t get to make a last phone call or pick out your favorite meal – assuming you leave this world without a death sentence and a jumpsuit on, of course.

I wonder if I’d worry about the same things that keep me up at night – the things I said wrong or never said at all, the moments that didn’t quite feel right, the not knowing. I know I would be wondering why I didn’t live this life a little more if I jumped in that car today.

I think about the people I know that carry great regret. The people who never spoke to family members again. The 20-year friendship that longed for a kiss. The love left lingering because no one would understand. I think we all know a story or two like that. What would they think about on the road? I wonder if they would regret lost connections. If their drive would leave them thinking about soulmates.

Surely, I have to believe they wouldn’t be worrying about what everyone else thinks.

That’s the foundation of so much regret – the perceived threat of losing it all based on everyone else’s perceptions. Perceptions created by anticipation and our insistence on controlling what others think about us. All the while following rules made up by people we don’t even know, rules we made up in our minds. Rules that dictate our lives and reward these deep regrets with more of what we never wanted. Things that are good on paper but don’t sit well with our souls.

Until you start saying hell yes to yourself. 

As I prepare for the next chapter of my life (big update I will share this month, promise), hell yes is the vibe. For the first time in my 30+ years on this planet, I am rewarding myself with a life that holds no regret. Probably a few wrong turns and a lot of “oh shit, what now?” but no regret.

Just wonder and a lot more hell yes.

Do the prompt. What do you need to say hell yes to? I know it’s not more regrets.


Regret is why I stayed in the closet at work for so long – the fear of finding out. That if they knew who I was, it would make them feel like they knew nothing about me all along. Mostly because of how I thought they would react. My fear played out at least 70% of the time when I was younger, so it wasn’t just projection. It was reality.

Now, it has been a few years since I came out at work. More than I want to admit right now. But the reactions haven’t changed. So, this week, I wrote about how straight people should respond when their co-workers come out.

Short advice: be cool.

You can read the longer version of that advice here.

Until next week,


Weekly Letters

Kat Kibben View All →

Kat Kibben [they/them] is a keynote speaker, writing expert, and LGBTQIA+ advocate who teaches hiring teams how to write inclusive job postings that will get the right person to apply faster.

Before founding Three Ears Media, Katrina was a CMO, Technical Copywriter, and Managing Editor for leading companies like Monster,, and Randstad Worldwide. With 15+ years of recruitment marketing and training experience, Katrina knows how to turn talented recruiting teams into talented writers who write for people, not about work.

Today, Katrina is frequently featured as an HR and recruiting expert in publications like The New York Times, Chicago Tribune, and Forbes. They’ve been named to numerous lists, including LinkedIn’s Top Voices in Job Search & Careers. When not speaking, writing, or training, you’ll find Katrina traveling the country in their van or spending some much needed downtime with the dogs that inspired the name Three Ears Media.

2 Comments Leave a comment

  1. This is great Katrina — and particularly in dedication to Scott and his mom. While I’m certain that the spectrum of circumstances are wide and varied, there are nevertheless far too many of us following paths that “reward these deep regrets with more of what we never wanted” and “are good on paper but don’t sit well with our souls.” Thank you for capturing this sentiment so powerfully and sharing so poignantly.

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