Photo by Rostyslav Savchyn on Unsplash

4 Ways to Minimize Regret

Regret sucks. Let’s talk about some ways to make it suck less.

What You’ll Learn

  1. The Regret Minimization Framework
  2. Any Unasked Question is a No
  3. Make Mistakes of Ambition, not Sloth
  4. The Only Question

The Regret Minimization Framework

The Regret Minimization Framework is a fantastic tool. It is similar to an algorithm in Computer Science called Hill Climbing. Hill climbing is focused on finding local maxima (a fancy term for finding the highest point close to you.

Math is Fun Maxima Graph
thanks to math is fun

Given multiple choices, we want to take the option that results in the least amount of regret after it’s over.


You have 3 options that will take you one hour to complete. Doing one prohibits you from doing the others, adding an opportunity cost to all the choices.

Option A: Exercise (Regret score: 15)
Option B: Hanging out with your friends (Regret score: 20)
Option C: Watching Netflix (Regret score: 45)

In this case, it is best to spend the hour exercising. It incurs a cost of missing conversation with friends, and not getting ahead in our show, but minimizes the guilt felt at the end of the hour.

Hill climbing and regret minimization is not a perfect science. By focusing on local maxima, we miss chances to find optimal routes. But the ones we do find are good enough.

Any Unasked Question is a No

Anxiety is the sibling of regret. Regret criticizes choices made, and anxiety criticizes thoughts about choices. Anxiety is useful in doses. It prevents stupid decision making, for individuals and societies.

The sucky part is that if anxiety wins, regret will also win later.

Let’s say you want to ask your boss for a promotion. You’re anxious because you don’t want a light shined on the work you’ve done. So you don’t ask. 3 months later, your coworker is promoted to the role, and you regret not asking.

You’ve felt and acted on both the negative feelings of anxiety and regret. Ouch.

Any unasked question is a no, so go ahead and ask!

Make Mistakes of Ambition, not Sloth

“All courses of action are risky, so prudence is not in avoiding danger (it’s impossible), but calculating risk and acting decisively. Make mistakes of ambition and not mistakes of sloth. Develop the strength to do bold things, not the strength to suffer.”
– The Prince, Machiavelli

The quote sums it up. There is no such thing as “no risk”. Make bold plays.

The Only Question

The final and easiest way to minimize regret is to ask yourself:

When I’m looking back at the end of my life, did I do everything I wanted?

Think in the long term. The short term has too many variables that pollute thinking. Long term thinking is values based, and since you can’t see how your plans play out, you’ll only have your values to guide you.

Join My Mailing List for Tips About Life, Code, and Writing

Analysis of Panic Room by Silent Planet

I’ve been listening to this song for a few days now, and I love it. I love the lyricism. There are a ton of clever metaphors. I wanted to take a deeper look into some of my favorite lines.

Selected lyric analysis below:

Lustrous lines obscured by opaque blinds
Frozen metacarpals tap tap tap the window glass

A person afraid of going to sleep, because they are afraid of what they’ll find when they close their eyes. The person in the song is suffering from PTSD from their time serving in the military.

The tap tap tap on the window glass is a vivid descriptor. You can imagine lying in bed, hiding under the covers, while your demons are right outside.

Syncopated staccatos with the broken clock
Synchronized with my post-traumatic ticks ticks

Phenomenal use of alliteration. I’m no English major, but damn, I appreciate this lyric. With every clock tick the person shudders, reminded of a time where every second could have been their last.

We’ve all lay in bed late at night, our eyes glued open at the ceiling. Each second feeling longer than eternity itself.

In my endless dance with entropy
I must rescind my sentience

We all have coping mechanisms. Defense responses to our internal struggles. Some drink, others watch too much TV, others eat. They all serve the same deeper end goal. To silence the voices that are telling us things we don’t want to hear, or remind us of things we do not want to see.

In the endless dance with the internal chaos, we cede our control.

Machines of air looking down on us
The beasts of dust as we grapple heel and hand,
Mud and sand, (blood red oil)
The chaff of the harvest
Converted to currencies of wealthy means
Stepping stones cut from our perforated bones
Riches are reaped beside our bodies sown just to be thrown back again
And forgotten if we stumble in
Laid inside a homeless nest,
Stuck with eager dirty needles,
Shipped to an early steeple
where boxes close
Descend with grace as you defend yourself
Both charitable and chaste
Praise me for my valor, lay me on a crimson tower
Justify my endless terror as my finest hour

Treat me as a token to deceive the child
Whom we fatten for this scapegoat slaughter

emphasis mine

Wow, just wow. This bit is quite political (which I don’t like to get into), but it made me so unbelievably sad. It gets the listener to question who is profiting from war, why we idolize the system that encourages young people to go and die for valor, to come back home and be mistreated and forgotten.

The homeless nest refers to the many veterans who turn to drugs to deal with PTSD, and then get shamed by their communities for trying to deal with their demons in the only way that they could find.

I learned to fight I learned to kill
I learned to steal I learned that none of this is real
None of this is real
None of this is real
None of this is real
But there’s a war inside my head

Another extremely heavy lyric. What is real? Does war end when you return to your family and friends? How do veterans use the skills they’ve learned? What about the millions of people who never fully come home?

tabula rasa

Two Sentence Paragraphs are the Future

Attention spans are slim, folks. This is no surprise.

In order to keep readers/listeners/users/watchers engaged, introduce new concepts.

A lot of blogs on the internet, they’re much too long.

They spend word upon word elaborating, elucidating, compounding, expanding upon.

Let’s make things simple. Simpler than they were in school.

Say what you need to say, nothing more. And use spacing, damn it! No one likes walls of text!

Silence is a virtue.

4 sentences per paragraph is much too many.
Stick to two.

what this piece looks like as one paragraph, I challenge you to try and stay focused the whole way through!

Attention spans are slim, folks. This is no surprise. In order to keep readers/listeners/users/watchers engaged, introduce new concepts. A lot of blogs on the internet, they’re much too long. They spend word upon word elaborating, elucidating, compounding, expanding upon. Let’s make things simple. Simpler than they were in school. Say what you need to say, nothing more. And use spacing, damn it! No one likes walls of text! Silence is a virtue. 4 sentences per paragraph is much too many. Stick to two.

wow queue time smh

Week 1 – Regret Minimization Framework: Choosing a WoW Main

What you’ll be reading:

  • class choice regret
  • too many options
  • minimizing regret by optimizing variables

When you look back at the end of your life, would you do it all over again?

Heroes of Azeroth, WoW Classic is upon us.

It is time to retrieve our weapons, don our armor, and sound the horns of war.

After your 4 hour wait in the queue, you finally see it. The character creation screen.

You pick a Tauren Shaman, and grind tooth and nail killing wolves, accepting quests and learning new combat abilities to level 10. You decide to become an Enhancement shaman.

You continue your journey, entering a PvP zone. You get ganked by a rogue. Multiple times. You get upset. Why can his class turn invisible? Yours can’t.

You decide to enter a dungeon. You whisper a group looking for a DPS. They ask you to heal. Wait, you say. I don’t want to heal. That’s why I chose Enhancement. Tough butts, they reply, they’re not looking for your role. Better luck next time.

You head back to the character screen and select Undead rogue. You grind to level 10. You head into a PvP zone. A warlock fears and DoTs you. You die. You get frustrated. Repeat.

There are many different ways to approach WoW, from casual to hardcore. And while there isn’t one correct choice, there are many wrong ones. Let me clarify that point. A bad choice means you chose a class or a role that is considered “bad”. At its core, WoW is a group game. If groups don’t want you, you’ll have a lot less fun.

Barking up the wrong tree costs time, and time is an invaluable asset. If you get to level 30 and decide that you hate your class, you’ll have to start a new one at level 1.

Regret Minimization Framework to the Rescue

Instead of considering all potential variables for a class choice (and there are a lot), let’s instead ask one question:

In one year, will you regret picking your class?

Go through the selection screen, through all of the races and classes you may want to play and ask yourself this question.

As for me, I’m going druid. Or maybe rogue. Hunter? Damn, still some choices to be made. See you in game.

Trying Out Mental Models

I’ve been hearing a lot about mental models. How they improve decision making, and can supplant heuristics we use day to day in our brains.

Over the next 30 days, I plan to use them to help me make decisions and see if I become happier, more productive, have a positive overall ROI.


The Rules

Focus on one per week, try and make at least one major decision and two minor decisions based off the model of the week. First up, regret minimization.

The Models

  1. Regret Minimization Framework
  2. ICE

Make short-term decisions using this model: When facing many options needing prioritization, score each on a scale of 1-10 using three variables.

The positive impact it would have if it succeeds.
The confidence you have that it will succeed if you try it.
How easy it would be to try it.
For each option, average its three numbers to get its ICE score. Then order all your options by their ICE scores. Options at the top of your list will have the highest expected value and should be given priority.

  1. Pareto Principle
  2. Eisenhower Matrix
wall niche

The Niche Myth

Small Holes

When you think of a niche, an image of a penguin might come to mind. Penguins have mastered their frigid environment, huddling together in the cold, and sliding on their bellies doing badass backflips off of glaciers. An ecological niche is when an organism is well adapted for its environment.

“If you put a gun to my head and said, ‘You have to come up with a story for Happy Feet Three,’ I’d say shoot me.” – George Miller

Or, for you architecture buffs out there, you may think of niches’ second, and less commonly used definition, a shallow recess in a wall. I don’t know how frequently this applies to anyone, tbh.

Today however, we will be discussing the third definition of niche:

(n.) a comfortable or suitable position in life of employment

** N.B.: the English language loves to overload definitions

Comfortable or Suitable Position? The Heck?

To be fair, that definition is pretty sucky.

Organisms in general, prefer comfort over conflict. People are no different. So, let’s just define comfort as being in a comfortable state most of the time.

Ok, how about suitable? That word is well…suitable. It acknowledges that no situation will ever be entirely ideal, but it can be suitable. In other words, “Meh, I’m ok right now.”

this is fine

Environment Envy

Arguably, one of the reasons the human species is so successful on Earth is how quickly we adapt to new environments. Hot, cold, mountainous, desert, or rainforest, you will find people all over the surface of the planet.

According to natural selection, success is determined by survival and continuation of the genes of an organism.

In business, success is defined as making more money than you’re losing. Whether you sell shoes, technology, or insurance, the goal is survival and growth.

The environment is an always changing system. The larger the environment, the harder it is to predict change.

Big businesses are harder to operate because they are less adaptive. For a real life example of this, decide what you’re going to have for dinner tonight. Now, ask a friend and decide together. Now, ask another. For every friend you add, the more complex the decision becomes.

Much like an environment, the market must be worked with, not against.

Success in a market is a combination of timing, a solid product, and the ability to sell. Without all three of these being present in some shape or form, a venture will be dead in the water. For a real life example of this, try to open a lemonade stand in December.

The Common Advice

People argue the importance of finding a niche, a hyper-specific use case for your skills/product/juggling talent. This advice is well founded. Many successful businesses we see in our day to day lives do something well enough to get people to part with their money. Even in a sea of competition, they continue to generate value and capture a percentage of that value.

However, I’d argue that the way most people go about finding their niche is flawed.

Better Advice

When choosing a niche to work in, set out to find your particular competitive advantage. If you don’t think you’re good at anything, what do you suck the least at?


Examine the competition. Monitor what makes the Taco Bell franchise successful, or why Apple has so many raving fans.

After you examine businesses you admire, throw out your findings. You are not Taco Bell. You are not Apple. Imitation will only get you so far.

Great artists steal, but their personality isn’t run over by the stuff they stole.

The Benefit of Staying Small

The smaller the better! Right? Well, kinda. Being small can actually be a bad thing, if you’re small in the wrong thing. For example, if your niche is making boots that are for moon walking, your audience is going to be pretty small, if not zero. Not that many people have been to the moon.

So I should go broad?

On the other hand, if your audience is too broad, it’s likely that your product won’t be good enough at solving a specific problem and you’ll disappear into the noise. For a real life example, look at most YouTube channels.

“WHAT IS UP YOU GUYS THIS IS ** insert channel name here ** !”

Strike a balance. Build something brand new, but make sure it’s something people actually want. People may say they want a live-action remake of Hey Arnold, but they probably don’t need it.

How do I find my niche?

Unfortunately, I haven’t found one answer. I spent weeks trying to narrow down into a niche for my YouTube Channel. I’ve tried podcasts, comedy styles, how-tos, video diaries and more.

I do have tips to share though.

The first thing is to make content that you enjoy. If you don’t enjoy the process, you’ll eventually burn out.

The second thing is that the content worth creating will signal back to you. People will come up to you and ask you about it. They love your neon chair lights, or your charisma on stage, or the way you make that dank soufflé. This shows genuine interest, and is a sign from “nature” that you’re on the right path.

Specialize in Adaptation

If you must specialize, specialize in adaptation. The environment isn’t static, so specializing in the traditional sense can cause more harm than good! If your soufflé business is going under, utilize your baking skills and pivot to the hot new dessert!


When I first wrote this article, I wanted to examine the relationship between niche and handedness. It didn’t end up fitting the vibe, but damn it, I’m gonna address it anyway!

I’m left-handed. About ~10% of the human population are left handed.

Why is this important? Well, almost by definition, left handed people are more adaptive to the environment. We have to be. Tools, cars, written language; are all made for right handed people.

For a real life example of this, ask a left-hander to write anything with a pencil and have their hand not look like this when they finish.

the struggle is real

Unfortunately, we also don’t get to complain about it. The environment very clearly signals that righties are dominant. Lefties must find their small hole as it was. Sitting on the left side of dinner tables as to not bump any elbows. Using notebooks with rings on top, etc.

Embrace your inner lefty. Adapt and utilize your strengths in any environment.

to each their own

to each their own
or so I’ve been told

some will stand
others will fold

the apple; doesn’t fall far from the tree
golden or rotten, it’s all the same to me

a person manifests their destiny by taking action
the universe responds with an equal and opposite reaction


“A man without a plan will quickly become banned/canned/overly tanned.”

I hate planning. I also love planning. I love feeling like I can control the outcomes of things, that a plan I’ve written down is exactly how it will play out in reality.

In the tech world, everyone loves “sprinting”. A sprint is a two-week period of a project, with a planning session at the beginning, and a retrospective session at the end.

Most of the time, in my experience, the “value added” hierarchy to the project goes:

doing the hard stuff > talking about what broke / what was learned from doing the hard stuff last time > planning the best way to do hard stuff.

Ideally, a plan is a document that will illuminate problems before they occur, so they can be safely avoided. Some plans are skeletons, others are so full bodied, they take more time to do than the project itself.

The problem is, plans never play out like they should. At best, plans save an equal amount of time on doing the hard thing that they cost to formulate. At worst, the time is entirely sunk because the plan is a steaming pile of garbage.

Whether you are writing a book, learning to fly a plane, or just how to make a burger; get to it. The less thinking and planning, the better, or so I’ve found.

First Month Retrospective


It’s been one month since I started working on my side projects full time. I’ve learned some things in this month. I’m not sure if any of these will be helpful to anyone since everyone has their own situation, but I hope something will be helpful to someone, somewhere.


Having all your time back isn’t all it’s cracked up to be

I thought that regaining back my hours of the work day (9-5) would allow me to feel that time is abundant. I was wrong. While it’s true that I get to decide what my hours are spent on, that doesn’t mean that they are spent better. A lot less time spent at a desk, but a lot more time on Netflix.

Night ?== Day

One of my friends asked me how my days are structured. I replied: “It’s like summer vacation, but worse.” For those of us who haven’t had a summer vacation, it basically means that all the days and hours blend into each other with no one hour being more important than any other.

I attempted to set up a schedule with Google Calendar, but I found that it was much too rigid. Next month, I’m experimenting with a more fluid schedule that enforces the number of hours worked, not when the hours are worked.



I started a budget last year. It’s been a phenomenal help to me. This month I spent what I considered to be “very little”, but I was still surprised by how much I spent at the end of the month. When moving your side projects into full time gigs, you need to calculate “runway”. I know mine, but let’s just say I’ll be eating rice and beans for the next…while.

my spending in june vs july

Spending in June vs my spending in July; still higher than I would have liked.

No Paycheck

My first month without a paycheck was interesting. One gets used to a certain standard of living when every two weeks money magically hits your bank account. I’ve really been able to reflect on what I need, and what’s worth abandoning. This quote from Nassim Taleb sums it up beautifully:

‘The three most harmful addictions are heroin, carbohydrates, and a monthly salary.’ – Nassim Taleb

Making Money from…something?

My initial goal was to work on my YouTube presence until I started being visible to sponsors. The goal would be to continue putting out content I enjoy creating, and live off of ad revenue and partner opportunities. If this month has taught me anything, that is a long way off from happening. In the meantime, I’m considering freelance opportunities and keeping my ear on the ground for opportunities that are remote and part time.

Inspiration and Motivation

It’s tempting to just “wait” until you feel so inspired to be productive. Unfortunately, inspiration rarely follows any logical schedule.

Cognitive Dissonce Hurts

I recently learned a new word! Akrasia. Akrasia is a Greek term for “the state of mind in which someone acts against their better judgment through weakness of will”. Basically, Akrasia is when you have a feeling that you should be doing something, but you’re not. You should be mowing the lawn, but you’re on Reddit. You should be working on that React Native app, but you’re watching The Office again.

Akrasia: “the state of mind in which someone acts against their better judgment through weakness of will”

When you have a boss, you have performance reviews, you have entire teams of people tracking your output. When you’re on your own, you become the manager and the managed. The only way to get something done is to do it. Simple as that.


Showing up every day. Compound interest. Garbage in, garbage out. Don’t skip leg day. Building a business is a marathon, not a sprint (or at least, that’s what I’m telling myself).

compund interest

Compound interest doing its thing! Snapshot of July from my Youtube analytics page.


I’ve always been a closet nerd. I own six Hunter x Hunter shirts. I spend a lot of my days on YouTube watching One Punch Man and DBZ reruns.

But since I’ve always “disliked” that side of my personality, I haven’t been able to integrate that into my work. I hope to change this next month, to be able to release content that is true to my soul; and non apologetic.



This one is huge. Exercise truly is what it’s cracked up to be. Stressed? Jog for a bit. Tired? Knock out 15 pushups. Need a morning routine? Head to the gym.

Exercise feels like a Swiss army knife and has become a core part in my routine, and helping me maintain a level head and getting me swolleeee.

Omega 3

The science isn’t conclusive, but I can say that taking omega-3 supplements have helped me feel less lethargic and more motivated when I would normally fall into patterns of depression.

(I’m willing to acknowledge that maybe it’s a placebo effect ¯ \ (ツ)/¯)


My sleep hasn’t been great. I’ve been able to sleep in, but I’ve been getting to bed too late. It’s incredible how an entire day can go by without a single good idea, but then 2am hits and the mind becomes a F-35.


I’ve been able to read a lot more, which is awesome. My favorite reads this month were Skin in the Game by Nassim Taleb and Hitchhikers Guide to the Galaxy, for entirely different reasons.


Still none…well no major ones, at least. I do miss the snacks in the office.


  1. Podcast with Max Hertan
  2. Finished my portfolio
  3. First stream on Mixer
  4. 24 subscribers (small, but a big deal to me!)
  5. Daily* conversations with my friend Ulrik, keeping me both grounded and motivated

*okay, maybe every other day


  1. Still no solid niche idea for YouTube
  2. Still spent more money than I would prefer to
  3. Too much time spent unfocused, neither resting nor working; just upset and unfocused

Plans for Next Month

  1. Find a monetization strategy to help propel business (profit first!)
  2. Find a mentor


I like the feeling of control. This world has so many incalculable variables, it’s a fool’s errand to try and control everything. But there are some things I can control. My time, how I spend my money, appreciating who I have and what I have.

This month has taught me a lot about self-reliance. I’m excited for the next one.