Don’t Minimize Regrets. Maximize Your Anti-Regrets.

Anti-regrets are the opposite of regrets: things you do that have a lasting benefit on your life. Here are some examples.


What’s the opposite of regret? 

Like, if you wanted to say the reverse of “My life is full of regrets,” what word would you use in the place of “regrets”?

  • Fulfilling actions? (Fullfillers?)
  • Adventures?
  • Pumps?  
  • Satisfaction?
  • Anti-regrets?

I’ll go with anti-regrets for now. And here’s my definition:

Anti-regret: (noun) Something you’ve done that has had a lasting benefit on your life.

The reason I want to talk with you about anti-regrets is because something crazy happened to me yesterday.

It helped me realize three things:

  1. I’m grateful to have lots of anti-regrets. Even though I’ve underachieved professionally, I feel good about the progress I’ve made overall.
  2. Rather than try to minimize regrets, maybe it’s better to maximize anti-regrets.
  3. What am I waiting for? I want to do more anti-regretful things.

To help you consider the same, here’s my best recollection of yesterday’s events, followed by examples of anti-regretful activities you might want to try.

The Story of My Anti-Regretful Conversation

Yesterday, I was sitting at my coffee table typing away at my next masterpiece on my laptop, like this…

Chris at his computer, where his anti-regretful conversation started.
The usual, before the unusual.

…when, all of a sudden, a pop-up took over my screen.

“Malware?” I thought. Serves me right for pirating Succession and Dave

Except this pop-up wasn’g an ad about gambling or sex. It was a video chat. And there, staring at me from my screen, was… me!

But this version of me had a slightly more crooked nose, smoother skin, and more optimism.

It was younger me!

Then he started talking…

Chris's 10-year-youngers self on his computer screen.

[Note: I’ve bolded my biggest anti-regrets and listed a bunch more ideas afterward.]

Younger Chris: Hey Chris. It’s me. You.

Me: No way. [Thinking, “AI’s officially out of control.”]

YC: Yes way. Let me prove it to you. [He proceeds to tell me secrets from my past that no AI could possibly know, and you don’t need to know either.]

M: Holy $%&… Where are you? When are you?

YC: I’m in Panama. 2013. Just pretired from P&G

M: Buy NVIDIA stock! Buy NVIDIA stock! Buy NVIDIA! Ticker NVDA!

YC: I wish, but they tell me they’re wiping this chat from my brain, Men In Black style, after we’re done.

M: Who’s “they”?

YC: If I tell you, they’ll wipe your memory, too.

M: So what’s the point of us talking? 

YC: They also tell me I’m the only one allowed to ask questions. 

M: [Waves hands in exasperation.]

YC: Given your desperate pleas for me to invest in that NV-whatever stock, I take it you didn’t succeed at becoming a wealthy, game-changing entrepreneur.

M: [Solemn head shake.]

YC: Dang.

M: But hey, at least I tried a bunch of businesses. I had lots of adventures and learned a lot.

And I’m far from bankrupt because I finally got my savings working for me. Even though I didn’t buy NVIDIA in 2013, my investments have compounded to give me a decent financial cushion. My biggest regret is not investing earlier. 

YC: Hmm. So if you failed as an entrepreneur, what are you doing? Back to corporate? Won the lottery? Married into wealth?

M: Ha, no. I married Kim—you know, Sarah’s sister. 

YC: WHAT THE F*&$?!?!?!?!?!

M: [Big smile.] She’s not at all like you remember from that one time years ago when you met her in Mexico. You’ll see. Soon, actually—in December 2013, at a restaurant. The next day, in maybe my best decision ever, I booked a flight to join her trip to Jordan in March then hang out with her after in Dubai, where she’s studying. 

Chris in Jordan with Kim, maybe his biggest anti-regret.
Jordan 2014. My #1 anti-regret.

YC: [Shaking head in disbelief]

M: The rest is history. (My history, your future.) We have a 2-year-old son, Zac, and another coming in August. Family life is going great, which I guess is the most important “start-up” to not fail at.

YC: Holy moly. So many questions. Are you a stay-at-home dad, then? Or what are you doing for work?

M: Writing, mostly.

YC: Seriously? But I don’t even like writing. 

M: Like with Kim, you’re going to fall head over heels for it. Writing helps you remember, learn, process, plan, brainstorm, and more. I write:

YC: What about books?

M: Not yet.

YC: Lame. 

M: [Sighs.] I don’t have a book idea anyone would want to read yet. 

YC: Then what do you [clears throat] “blog” about?

M: Well, I started with travel

YC: Oh yeah? Been to some cool places? 

M: Tons. The Philippines, Jordan, Japan, Sri Lanka, Peru, Mexico, Kenya, Namibia. But I mostly wrote about the places I’ve lived in: Medellin…

YC: Nice.

M: Very. And Valencia; Vancouver, of course; Essaouira, Morocco; and Cape Town, our second home for the past five years. 

YC: Cape Town? Random. What’s there to do there, other than write?

M: Mostly the same as in Vancouver: Hang out with friends, hike, explore, play beach volleyball

YC: Beach volleyball? 

M: Yeah. Kim got us started with trainings in Cape Town. It’s replaced basketball as my favorite sport. Easier on my knees. More social. On the beach. Bikinis.

Chris' son Zac holding a volleyball in Cape Town.
Three anti-regrets in one photo: Zac, beach volleyball, and Cape Town.

YC: Are you any good?

M: Not amazing. But solid for a guy who started at 32. I read this book, The Inner Game of Tennis, which changed my approach to learning skills

YC: Interesting. What other skills have you picked up? A new language? An instrument? Cooking?

M: Not enough, now that you mention it. Writing is the big one.

YC: Yeah, yeah. That’s it?

M: No. Also, umm… making websites… 

Oh! I got one: photography. Daryl taught me. Knowing how to take a semi-decent photo preserves memories better and gets me looking at the world from a different, well, lens—even when I’m not taking pictures. 

Speaking of perceiving the world differently, another skill I’ve improved on is my sense of taste.

During COVID…


M: Never mind. Anyway, I read a book on the science of taste and one quote, “Why would anyone who learns to appreciate flavor ever turn the clock back?” convinced me to train my palate

“Why would anyone who learns to appreciate flavor ever turn the clock back?”
– Bob Holmes, Flavor: The Science of Our Most Neglected Sense

YC: So you’re a food snob now? 

M: Not even close. Nachos and Blizzards are still my faves. But I used what I learned to teach myself to acquire the taste of black licorice, which was fun if useless. Most importantly, I trained myself to appreciate good food more. Wine, too, though I’m not sure that’s a good thing.

YC: [Shaking head.] Wine’s such a money-suck.

M: Yeah, but in South Africa I couldn’t help but get sucked in. Speaking of sucking. See my nose?

YC: How could I not? Still big and bent.

M: But not as bent as yours because I finally got around to getting surgery on my deviated septum. Now it works! I smell stuff. And I re-trained myself to breathe through it!

Chris stopping to smell the flowers
My nose doesn’t look great, but it works!

YC: Nice. Too bad the doctor didn’t do a better job on aesthetics.

M: Yeah. Still, nose-breathing had been surprisingly beneficial. No more seasonal allergies. Better sleep. 

You’ll think this is funny: I tape my mouth shut every night to force myself to nose breathe. By the way, I also sleep on the floor, Japanese style.

YC: Wild. 

M: Another wild change: I gave up snacks. Now I only eat once or twice a day and occasionally fast for multiple days

YC: Sounds miserable. 

M: [Shakes head.] Snacking was a hard habit to break, but as they say, “Once you break snacks, you never go back.”

YC: That’s a saying in the future?

M: I don’t think so. 

“Once you break snacks, you never go back.”
– Nobody (But it’s true.)

YC: At least you don’t look emaciated.

M: I still eat a ton, just less frequently. And I still work out too, though entirely outside nowsprinting, calisthenics, jumping, throwing rocks, etcetera. 

YC: You can’t even afford a gym anymore?

M: Nah. I love the fresh air. I even do computer work outside on picnic tables.

YC: What a hippy. Do you wear hemp, do psychedelics, meditate, and live in a commune, too?

M: No. Merino instead of hemp. It’s all I wear now, along with the same Lululemon shorts you do. 

As for meditation, I tried, but I prefer walking or writing. Still not into drugs, either.

The commune idea’s interesting, though. Living in the same block or neighborhood as close friends and family would be awesome. Ideally, somewhere warm and walkable. 

YC: So why don’t you make it happen?


With those words, the magical video chat window with 27-year-old Chris disappeared from my screen. No goodbyes or anything. Sad.

But then another weird thing happened

I can’t remember it exactly. All I have is a hazy, dreamlike memory of another window opening up, this time with an older guy. I remember asking him questions, but I can’t remember what he said.

I believe it was cool. 

Your future self cover image of me and future me smiling and high-fiving
What can you do that’s likely to earn you a huge high-five from your future self?

What Are Your Biggest Anti-Regrets?

What progress would you be proud to report to your 10-year-younger self?

And what about the coming ten years? What could you do/learn/develop to have a lasting benefit on your life? 

Potential Anti-Regrets:

  • New skills. E.g., languages, photography, instruments, cooking, crafting. 
  • Improved skills. E.g., lessons, coaching, deliberate practice.
  • Remove recurring issues. E.g., getting surgery on my nose, changing jobs, getting organized. 
  • Better tools. E.g., merino, an excellent knife, repaired phone screen, a good computer. 
  • Learning. E.g., understanding psychology, learning how to learn, gaining a deeper knowledge of the world around you.
  • Improved physical health. E.g., eating habits, enjoyable fitness lifestyle. 
  • Mental health: E.g., taking breaks, fresh air, meditating, writing. 
  • Adventures: E.g., travel, trying new businesses, 30-day challenges.
  • Relationships: E.g., kids, social events, meeting new people, time with family and friends.
About the author

👋 I'm Chris. Everything you read on is my fault. This site is like a gym for your comfort zone, full of challenges to make your status quo sexier. Join my 'Consider This' newsletter for a fun new challenge every 10 days. Try it!

Leave a Comment

Latest Articles


The Zag shares my adventures off of the boring beaten paths of life and ideas for finding your own unfollowable path.