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- #120: Book your regret
#120: Book your regret
Shem Opolot
May 09, 2025
Hi! Welcome to The Friday Fix! You’re reading this because you probably stumbled upon this post somewhere on the internet instead of where it should be—in your inbox. But no worries; we can fix that.
Who am I? I’m Shem Opolot, a health professional turned content creator, passionate about helping people be their best selves in life and work.
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I have over ten years of work experience in healthcare, program management, and data analytics on two continents. So, I know a little about helping you work smarter
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Hi! I'm Shem Opolot, and this is The Friday Fix, my weekly newsletter. If you've received it, you’re either subscribed or someone forwarded it to you. If you fit into the latter (yes, I’m the kind of person who uses words like “latter”) camp and want to subscribe, then click on the shiny button below:
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***
I’ve spent all week at my desk, completing the comprehensive exam for my doctorate. My hair is overgrown, and I have the beginnings of carpal tunnel, but this is me showing up for you anyway. This will be the last exam I ever have to take in my life.
LIFE.
Book your regret
Regret piles up around us like books we have never read
My friend started an OnlyFans, and I’m so proud of them.
The muddling murmurs of the morality mob in my mind notwithstanding, I’m proud of them for taking a risk. A risk that’s earning them close to $10,000 a month.
You see, risk and regret are—what I like to call—chicken-and-egg relatives with bidirectional causality. You can experience regret if you don’t take a risk, but you can also take a risk so that you don’t experience regret.
I started writing consistently about 2 years ago, inspired by one of my favorite YouTube creators. But even as the creator reached through my laptop screen, grabbed my shirt collar, and demanded I write, they still added—in some twisted self-fulfilling prophecy and masterful manipulation—that whenever I started writing, I’d begin with a deficit in my writing bank account. That I’d regret not writing earlier.
Two years later, with thousands of you reading this, I regret not writing earlier.
Frozen by fear and people’s perceptions, I postponed this great thing that has opened up my world in vast and varied ways. That has given me many new friends I’ve never met and afforded me a discount on therapy by allowing me to process my thoughts.
A while back, I stumbled upon a trite, properly search engine optimized Harvard Business Review (HBR) listicle piece titled The Top Five Career Regrets.
Can you guess those top 5 regrets? Indulge me—hold at least 2 guesses in your mind for later.
Also a while back, curious about the pervasiveness of these career regrets, I asked my Instagram followers what their worst regrets in life were, and most people…
…ignored me.
Of course. In fact, the main lesson I learned from that paltry poll was that when people say, “A lot of you have been asking…” the call is often coming from inside the house.
But some people responded:
“Not coloring my hair when I was younger”
“Fear of other people’s opinions cost me some good deals”
“Not trusting myself sooner”
“Procrastination and letting fear lead instead of courage”
“Not saying no on time and wasting my time with people who didn’t care about me”
“Being afraid to take risks”
“Ignoring the red flags in people and being a people pleaser”
and my personal favorite:
”Waiting too long to lose my virginity.”
Most people’s regrets fell into three categories: 1) how they chose to spend their time in the past, 2) failure to act because of the fear of what other people might think, and 3) not taking risks.
Remember Harvard’s Top Five Career Regrets from earlier? They were:
I wish I hadn’t taken the job for money — risk
I wish I’d quit earlier — risk
I wish I had the confidence to start my own business — risk
I wish I’d used my time in school more productively — time
I wish I’d acted on my career hunches — risk
My Instagram followers and the people HBR interviewed share essentially the same regrets.
So yes—regret piles up like books we’ve never read, but also, it seems, we all want to read the same books.
You want to spend more time doing what you love with those you love. You want to take more risks. You want to do what makes you happy without worrying about what others think.
Your regret runs on your skewed perception of time. You think you don’t have enough time to make changes or do certain things, and sometimes you’re right. But often, you’re wrong.
The cream and cruelty of life is you don’t know how much time you have, so obsessing over time is pointless. Time is always on your side as long as you’re alive, so take that risk, if anything, because, as they say, you can’t be late to your life.
THINGS.
A quote.
I apologize if the NSFW-ness of this quote offends you, but it’s a damn good quote from one of my faves. Plus, I agree.
People wanna be fuckable more than they wanna fuck…fucking is labor, fuckability is capital
A picture.
I visited a botanical garden last week, and the experience did wonders for my spirit. Plus, there are sections of the estate that could be ideal sets for Season 3 of Bridgerton.
Dumbarton Oaks Garden in Georgetown, Washington, D.C.
WORK.
Sometimes you need fake emails
No, the irony isn’t lost on me.
But if you want to sign up for something without opening yourself to spam later, use this site.
FUN.
The Friday Fix playlist
Shem’s picks
✅ If you want to get better at drawing, this is for you
✅ How to cut the most common vegetables
✅ What if money expired?
✅ Elizabeth Gilbert on Hobbies, Jobs, Careers, And Vocations
✅ How to fix your stuff?
Have a great weekend,
— Shem
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