Better Judgement = Better Decisions


Couple weeks ago I was presented with a major decision. That got me thinking, how do people go about making huge decisions that affect the rest of their lives. I’m accustomed to making decisions at work, which are usually done in big meetings where all the data and analysis are presented, facilitating a discussion, and making a decision based on priorities.

But when it comes to our personal life, these decisions could be deeply emotional, with no clear right or wrongs. In this article, I’ll give some tips on how to make better decisions.

Biggest Decisions of Your Life

Here are 3 tips that you should consider:

  • Accept short term risk for long term gains. Mark Manson, author of The Subtle Art of Not Giving a F*ck, states it like, “the sweet spot… is to find the short-term failures that enable the huge long-term successes… Because this is what most people are bad at. And because people are bad at it, this is where most of the opportunity lies.” [5] In our survey 73% of Venture Out readers said they think long term. Takeaway: Say yes to small risks with big gains.
  • Intentional listening to your gut. Engineering decisions should be based on calculations and analysis. Therefore, emotional decisions should be based on how you feel. This 2005 study concluded that, “Contrary to conventional wisdom, it is not always advantageous to engage in thorough conscious deliberation before choosing.” Our survey, 87% of Venture Out readers say they overthink their decisions. Takeaway: Make that decision and then sit with it for awhile. Gauge how you feel.
  • Own your decision. When I was faced with my major decision, I asked a lady I’ve worked with and known for over a decade. She’s been happily married for over 30 years with kids, and grandkids, all of whom have great family values. Her advice: once you make a decision, really own it. There will be times of doubt and everybody has them, but you have to live with your decisions. Takeaway: Once you’ve made a decision, don’t go back, only forward.

Why Drama Is Following You

Movies That I Love: It Follows

In the 2014 movie, It Follows, a scary supernatural force follows a young woman after she had a sexual encounter. Turns out, this deadly creepy thing gets passed down like a bad heirloom to the next sexual partner. So the only way to get rid of it, is to have sex with someone and have it latch onto that poor sucker.

Okay, probably a horrible analogy, but that reminds of people who tend to have drama follow them. And why is that? Poor decision-making? No, it’s something deeper than that — judgement.

“Here’s one thing I’ve noticed over the years: shitty dogs almost always have shitty owners. The dog’s level of discipline is reflected in the owner’s emotional maturity and self-discipline. It’s very rare to see a dog that’s wrecking the house, eating all the toilet paper and pooping all over the couch and the owner has their own shit together.” — Mark Manson

Judgement is making a decision that is sensible, considered, careful. That sounds good, but how do the heck do we get better at it! I’d venture to say folks who have drama follow them would attest they do try to be sensible.

Here are two tips on how to improve your judgement:

  1. Past Performance Matters — Be honest with your past. Maybe you’ve made bad decisions when it comes to money or relationship choices. If so, don’t trust yourself and instead take the advice of someone who is good at it. Be like Jim Carrey in Yes, Man, and just do what they say. Over time, you’ll calibrate to better judgement. Another analogy, when someone plays tennis for the first time, they usually can’t control where they aim yet. So if all their shots are landing 20 feet to the right of the court, I coach them to aim 40 feet to the left. By over-compensating, they’ll get closer to their aim. Over time, with muscle memory, they’ll self-calibrate and know what feels accurate.
  2. Learn Probability — “Research has shown that even relatively basic training in probability makes people better forecasters and helps them avoid certain cognitive biases.” That’s according to this HBR article, that goes on to recommend the a Khan Academy class. It’s kinda dry, so try this 5 min YouTube video by Mathematician Lily Serna and learn the 37% rule in making decisions. Or, if you’re really intense, here’s a 1 hr Stanford class lecture.

Who Will You Vote for in the 2020 Election?

I’ll admit, this headline was meant to get you all riled up! And why did it? Why has the topic of politics seem to be more polarizing than ever. I actually don’t want to talk about politics! Rather, let’s understand why our minds are made-up, and explore how flexible or rigid we are to entertain different ideas.

This reminds me of that bestseller, Team of Rivals: The Political Genius of Abraham Lincoln. The author asserts, Lincoln, “won because he possessed an extraordinary ability to put himself in the place of other men, to experience what they were feeling, to understand their motives and desires.”

PS. 77% of Venture Out readers said they already know who they’re voting for.

Be Less Certain — That’s rule #1 from this HBR article on how to make better decisions. According to Nobel prize winning Daniel Kahneman, an economist notable for his work on the psychology of judgment and decision-making, “overconfidence is the bias he’d eliminate first if he had a magic wand.”[8]

It seems counter-intuitive. All our lives we desire to gain confidence. Confidence allows us to be more sure of ourselves, improve our self-esteem, and just go through life with more certainty. Yet, this advice is telling us be more doubtful. It’s like a Yoda reverse logic!

The takeaway is, to achieve better judgement, detach from your decision both intellectually and emotionally. We are constantly biased (tricked!) into thinking a certain way because of tactics like anchoring, confirmation-bias, and risk preference. Therefore, practice, practice, practice… but don’t lose your confidence.

Essentials for Making Better Decisions


How many times have you gotten frustrated with a coworker, replied with a snarky email that’ll put them in their place, and then immediately regret it? Just the other day I was feeling stressed at work, so I wrote this message venting to my boss… but then I let it sit there for hours. By the end of the day, it wasn’t worth sending anymore.

Doesn’t matter how big the decision, if it’s deeply emotional, or how small and trivial it may seem, we need to have great judgement.

To me, judgement is like experience — people say you need more of it. But how do you magically get more of it? The world doesn’t slow down while we’re off getting “experience” or practicing “judgement” in safe places. That’s why I like to talking to old people, so I can data mine them for experience. Haha.

Here’s what I do to speed up that process, and ultimately, have better judgement.

  • Before making a decision, ask myself when was the last time I made a similar decision, and how did it turn out. If it worked out good last time, press on! But if it sucked last time, maybe I should try something different.
  • Get advice from someone who’s good at that topic. For example, if you had a friend who’s good with finances but horrible at relationships, then you know obviously what to do. You ask them for cheap date ideas. Just kidding.
  • Listen and don’t think. You’ve heard it a billion times but it helps with judgement too. IN any conversation, listen and STOP yourself from thinking of a response, or how it remind you about something, etc. Just listen. This helps because you’ll pick up so much more info (including body language), which helps with judgement.
  • Read more. This is the area that I actually don’t do nearly enough of. Besides reading comics and listening to podcasts, reading books is a great way to ‘consume’ the knowledge of others, which in effect increases your experience set.
  • If all else fails, watch Terminator 2: Judgement Day.


  1. The Five Decisions that People Regret the Most by Travis Bradberry
  2. Here’s How to Feel Satisfied With Your Life Decisions: Modern psychology offers three ways to make peace with your decisions.
  3. On the benefits of thinking unconsciously: Unconscious thought can increase post-choice satisfaction by Ap Dijksterhuis and Zegervan Olden
  4. How To Make Difficult Decisions (And Live With The Consequences) by Chris Myers
  5. How to Make Important Life Decisions by Mark Manson
  6. The Elements of Good Judgment by Sir Andrew Likierman
  7. How Systems Support (or Undermine) Good Decision-Making by Ron Carucci
  8. 3 Ways to Improve Your Decision Making by Walter Frick

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