To make the most rational decisions, use your gut
I recently made the decision to leave my comfortable, stable job to join a pre-revenue startup as the first employee. With the economic uncertainty going on in the world, it was a hard decision to make.
Being a left-brained tech person, I agonized for weeks on how to tackle the decision making process as rationally as possible. I looked up mental models and read as much as possible about how to make decisions without biases. I listed out all objective criteria I could think of then gave weight to each criterion. However, as time went on, I had more criteria to add, and the weights I’ve given for the criteria even changed depending on my mood. That’s when I realized I needed a different approach.
Intuition to the rescue
Intuition is a certain feeling you have towards something that you cannot put into words. Unlike popular belief, intuition is not a snap judgment but a result of accumulation of experiences you have throughout your life. Intuition is in every decision that you make, even when you think otherwise.
Gerd Gigerenzer, a psychologist who studies rationality in decision making, asked executives in some of the largest companies to think about the last 10 important decisions they made and assess how many of them were a gut decision at the end. The answer was 50%. So even for people in consequential positions, every other decision is at the end a gut session. Intuition is widely used, but people don’t want to admit that it factored in their decisions in fear or being seen as irrational.
It is common to think of intuition as irrational since it manifests as unexplainable feelings and emotions you have towards certain things. The truth is, emotions are not the opposite of rationality. Marvin Minsky, the father of the field of artificial intelligence, argued in his book The Emotion Machine that emotions are not distinct from thinking, but in fact one of the “ways to think.” Furthermore, when incorporating emotions into your decision making process, you can increase your understanding more:
“If you “understand' something in only one way, then you scarcely understand it at all—because when you get stuck, you'll have nowhere to go. But if you represent something in several ways, then when you get frustrated enough, you can switch among different points of view, until you find one that works for you!” (Minsky)
When should you use intuition?
Is there a situation where it’s better to use intuition than another? Gigerenzer explains that when thinking about using intuition, you should distinguish between situations of risk and uncertainties. In situations of risk, like playing a roulette or lottery, all possible outcomes and consequences are known, it’s better to use calculations. In situations of uncertainties, like investing or deciding who to marry, it’s better to use intuition.
In my case, deciding whether to make the jump for startups is certainly (ha!) a situation of a lot of uncertainties. Leaning into intuition is therefore a no-brainer. Below are the steps I took to come to my decision.
How do you use intuition in decision making?
From Judgment in Management Decision Making, a common framework for decision making goes like this:
Define the problem
Identify the criteria
Weigh the criteria
Generate alternatives
Rate alternatives on each criterion
Compute the optimal decision
I went through a similar process modified to incorporate more intuition with the help of Luca Rade, a decision coach. I’d recommend that you go through this process with another person as a sounding board -- this will help you clarify your thought process, and the person doesn’t need to be a professional or a person at all! (see rubber duck debugging)
Step 1: Understand how you feel about each of your choices
First, look at your choices. Write down how you feel about each of them in bullet points, in terms of values and disvalues to you. For each bullet point, write down all the reasons for why you feel that way. For each reason, ask why 5 times and write down each reason as a nested bullet point.
This might seem like a pros/cons list, but the difference is that you are looking at how the choices add or subtract value to you specifically. The reason I had so much trouble with the pros/cons list before is because I kept listing out values that didn’t matter to me. For example, a pro of my stable job is awesome benefits, which include tuition reimbursement, employee assistance program, etc. The value looks good on paper, but I’ve never used it. So listing out how you feel is a more accurate way to assess the values and disvalues each choice has to you.
5 Why’s is a method for problem solving invented by Sakichi Toyoda, the founder of Toyota Industries. The method helps you unpack the root cause of a problem. Similarly, using the method in this exercise will help you understand the intuition and assumptions underlying the values and disvalues you listed.
For instance, when thinking about the startup option, one of the values I wrote down was:
I feel like the startup will set me up on a better path career-wise because:
I have more control over my destiny
I am more mission-aligned with the startup
etc.
For the first reason, I expanded the why 5 times:
I have more control over my destiny
Because I feel confident in my ability to influence the company to go to the right direction
Because I believe I have and will learn the right skill sets to produce good results
Because I’ve frequently done well on things I set out to do
Because those things were hackable and I persevered
Similarly, one of the disvalues I wrote down was:
I feel scared of taking the startup option because:
The startup might not work out
COVID-19’s economic uncertainties might limit my options afterwards
etc.
Again, for the first reason, I expanded the why 5 times:
The startup might not work out
Because we might run out of money before finding product-market fit
Because we might not have allocated our capital correctly
Because we over-invested in certain things
Because of sunk cost fallacy
What this exercise does is bringing out my immediate excitement and concerns about my options and helping me understand why I feel that way. Take the value and disvalue above. From doing the 5 Why’s, I realize that I am excited to be in control of my destiny in the startup, but scared that I will make the wrong move at the same time -- because while I have generally succeeded in what I do, those things were more structured than a startup. Therefore, I feel both excited and scared because taking the startup option means taking a bet on myself that I will be able to adapt in an unstructured environment.
Step 2: Zoom out and think about your overall values
After you have a picture of why you feel certain ways about your choices, think about your current values. One way to start is to list out all values you have, which you can start by choosing from James Clear’s list.
Another list I found helpful is what values to think about when choosing what to work on:
Knowledge — Do you become more knowledgeable and skilled when doing it?
Adventure — Do you accrue novel, memorable experiences?
Fame — Do you build an audience you can later leverage?
Power — Do you acquire resources and connections?
Money — Do you increase your financial wealth?
Exercising Talent — Do you leverage your skill and creativity?
Human Connection — Do you bond with others?
I believe that time is the most precious asset, so when I’m young, I want to invest in things that will compound while enjoying the process. So these are my current values in descending order:
Human Connection
Knowledge
Adventure
Exercising Talent
Power
For me, getting to know other people is one of the most enjoyable things, and I also believe that I learn the most when interacting with others. That’s why Human Connection is ranked first.
Knowledge, Adventure, and Exercising Talent are next because while my brain is still developing, I want to accumulate as much knowledge and novel experiences as possible and practice them. Power should come naturally as a result of doing the first four.
By defining my current values, I know that I should choose the option where I feel that I could maximize them in the shortest time frame.
Step 3: Modify your choices
Now look at your list from step 2 and 3 and ask yourself: is there anything besides the choices you currently have that will allow you to achieve the values you want?
Two possibilities emerged for me:
Starting my own thing
Working at a more stable startup (post-Series A)
Then look at your original choices, ask yourself: what can you do to increase the values and reduce the disvalues for each choice? This is where having an outside perspective can be helpful.
Lastly, ask yourself: is there anything else that is nagging you? When that happens, you can do the 5 Why’s exercise again and examine the reasons against your values. One that came to my mind was getting a job at a FAANG-like company. The possibility appealed to me because of the money. But money is not on my list of values because I believe that investing in myself now with the other 5 values would give me a bigger return than making a lot of money and putting them in an index fund for 7% return. That helped me quickly eliminate the option.
At this point, my viable options are:
Go with the startup
Modify my current job to increase my learning
Stay at my current job while working on a side project
Stay at my current job while hunting for a job at a post-Series A startup
Step 4: Simulation
In Seeing What Others Don’t, psychologist Gary Klein suggested mental simulation as a tool for making decisions with intuition. If you have done the above steps, it should be easy to imagine what your life is like if you have gone with one of the options.
Over four days, for each day, I imagined the future possibilities for each of my options. Keeping these two questions in mind during the exercise was helpful for me:
What am I afraid of?
What regrets do I have for choosing this option?
Comparing your fears and regrets against your values will also help steer you towards the option that works for you.
Step 5: Go with your gut :)
After going through all these steps, it will be clear to your intuition what decision you should make. Now you just have to go for it!
In the end, I chose to go with the startup. It was clear to me that I would regret not choosing it the most, and it was also the most aligned with my values.
The benefit of intuition is that it doesn’t fool you into thinking that you have all the answers. Your values will change over time, and it’s okay to change your mind later. That’s why there’s also another step:
Step 5+: Reassess every once in a while
Remember the lists you have from making your decisions? Keep them somewhere safe and set a reminder to go back to them at least every quarter. Repeat all the above steps if necessary, and have the courage to listen to your intuition if you change your mind.
All animals have feelings and intuition. What is uniquely human is our ability to connect our emotions, intuition, and intellectual processes together to create a whole new world around us -- after all, how would we have arts without feelings? Hard decisions are complex, messy, and decidedly human. You can’t make them without intuition.