8 min read

When and How to Trust Your Gut

When and How to Trust Your Gut

Daniel Kahneman is a Nobel prize winner in economics for his work on human judgment and decision-making. He proposed that we have two different thought systems:

  1. A faster system that relies on intuition
  2. A slower system that relies on analytical reasoning.

When you’re making a snap decision based on experience or emotion, you’re relying on intuition. And when you methodically solve an objective problem, you’re using analytical reasoning.

But what about big life decisions that are subjective yet capable of irreversibly altering our life trajectories? When should we use intuition and when should we use reasoning?

For these decisions, we shouldn’t underestimate intuition or blindly follow it. Let’s discuss insights around when and how to leverage your intuition.


First, let’s define what makes a good life decision

Some behavioral or economic researchers define a “good” decision by the one that makes the most money or gains the most utility. And for their purposes, that’s fine.

But we’re here to tackle decision making for subjective, consequential life decisions such as what career to pursue, where to live, who to marry and whether to have kids. Done correctly, these decisions are the ones that lead to greater feelings of purpose, meaning and fulfillment, and ultimately enable you to craft a “life well-lived.”

And here’s our first insight: a “life well-lived” is not an objective criteria. It’s not a set of checkboxes you can satisfy. Someone else cannot look at your life and measure whether it was well-lived. A “life well-lived” is a feeling. And I’ve found that for most people, it’s a feeling of having no regrets; you’ve done what you need to do and said everything you want to say.

So for our purposes, a good decision is a decision that minimizes regret.


The relationship between regret and intuition

Think of a time you made a life decision you later regretted. What role did intuition play? If you’re like me or the many others I’ve talked to, you’ve experienced regret from both disregarding your inner voice and trusting it blindly.

Examples of disregarding your intuition and internal desires:

  • Giving up on a dream career for a “safer” career path.
  • Choosing to study a safe major with more job prospects, rather a major that truly interests you.
  • Working at a large, bureaucratic company with great benefits instead of at a smaller, scrappier company with a mission or product that resonates with you more.

Examples of blindly following intuition:

  • Clouded judgement.
  • Susceptibility to biases.

Now think of a decision you made that greatly improved your life, either through greater satisfaction, excitement or meaning. What role did intuition play? Typically, the life decisions we think of most positively involve taking a risk and making a change, rather than staying stagnant. And often times after rationally deliberating a decision, our intuition gives us the final nudge to commit to taking that risk and making that change. Rewarding decisions are often made with a mix of analytical reason and intuition.

Examples of rewarding decisions:

  • Choosing to move to a new city (for college or work) as opposed to staying near your hometown despite its familiarity.
  • Joining a new organization or community out of your comfort zone that you’re curious about or interested in.

These examples should begin to motivate that intuition plays an important role in minimizing regret and maximizing flourishing. Let’s dig deeper and discover how to tactically incorporate intuition to make fulfilling choices in subjective, consequential life decisions.


How inspiring people use intuition to make life decisions

Chase Jarvis (CEO of CreativeLive) was recently asked by Tim Ferris how he decides whether to quit or persist.

Chase replied that he always starts with intuition, because "intuition is the most powerful tool that we have as humans.” Like many cognitive scientists, he is optimistic that lots of knowledge and experience is stored in the brain and body beyond the reach of our conscious working memory, and intuition is a powerful way to access this data when making decisions.

“Intuition is both that feeling you have in your gut. And then, for the folks that are a little less woo-woo and a little more scientific, I believe we’ll see a lot of science that’s in the near future and is just starting to emerge around the data that is stored in the body that we have a slower ability to recall, or it’s recalled in a different way than just in the mindfulness. That’s one of the reasons that intuition feels like a gut feeling.”

As the CEO of CreativeLive, Chase interacts with many inspiring people who successfully make a living doing what they love. He’s found they similarly rely heavily on intuition.

“Every creator that I know who has made really successful things, not all successes, but that you would look up to and say that person is a badass, every time I’ve talked to them, there’s been a really strong element of intuition.”

He points out that intuition helps identify the decision we want to make; “You know in your gut deeply around intuition whether something is worth pursuing or not.” However, we need to rely on our conscious working memory to explicitly rationalize and justify the decision to ourselves. So in addition, he applies a simple sniff test by asking the following two questions:

  1. Is this something that brings me joy, and/or is this working? Am I making progress, and if so, is this internal progress or external progress?
  2. Do I still care about this? Do I believe deeply in the mission or the vision of what I’m talking about doing such that I’m willing to endure?

If both answers are "Yes," he persists. If both "No," he quits. If one is "Yes" and another is "No," he dives deeper. He learned this framework from Chris Guillebeau's book Born For This, where Guillebeau studied all kinds of people who had gone through the process of trying to make a living and a life doing what they loved.

“Remembering I'll be dead soon is the most important tool I've ever encountered to make the big choices in life. Because almost everything – all external expectations, all pride, all fear of embarrassment or failure – these things just fall away in the face of death, leaving only what is truly important. Remembering you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked, there is no reason to not follow your heart.” – Steve Jobs, 2005

From my own conversations with startup founders, content creators and other inspirational people paving their own unique life paths, I’ve gained the insight that being able to incorporate a strong element of intuition into decision making is a delineating trait of people living purposeful, meaningful and fulfilling lives. And luckily this skill can be trained.


How can we train our intuitive skills?

Some cognitive scientists believe intuition is neither irrational nor the opposite of logic. Rather it is a quicker and more automatic process that plumbs the many deep resources of experience and knowledge that people have gathered over the course of their lives.

Intuition is an ability that can be trained and can play a constructive role in decision-making. I’ve found that there are different dimensions to intuition – different ways we’re able to tap the knowledge outside the reach of our conscious working memory – and my insights for how to develop and use intuition differs by each dimension.

We’ll discuss three core dimensions to intuition in this essay:

  • Emotional intuition – “I was not completely sure how to decide, so I decided based on my gut feeling”
  • Experience-based intuition – “I did not have time to decide analytically, so I relied on my experience”
  • Instinctual intuition – ”I was stressed out by having to decide, so I relied on my instincts and went with the proven option that other people also chose.”

Emotional intuition is derived by the unconscious, emotional side of your mind.

Disregarding your emotional intuition when making a decision can lead to regret, but over-relying on emotional intuition can cloud judgement. A promising way to incorporate emotional intuition into big life decisions is learning to be aware of and lead with your emotional intuition as Chase Jarvis suggests above.


Experience-based intuition on the other hand relies on our ability to efficiently pattern match.

This type of intuition emerges and improves as you live through more and more experiences relevant to that decision, just as experienced drivers frequently experience the phenomenon known as "highway hypnosis,” which occurs when a driver travels for miles without a conscious thought about the activity of driving the car. With enough of the right experiences, experiential intuition can arrive faster at the same decisions you’d make with an analytical approach.

In a study of several managers at a company of varying seniority, upper-level managers tended more towards intuition than rational analyses. The key insight here is not that trusting your intuition makes you a better decision maker, but rather people with more experience making good decisions through rational analysis earn the ability to rely more heavily on their experiential intuition.

Thus, seek out opportunities to make the types of decisions you’d like to eventually make quickly and intuitively.


Instinctual intuition is driven by our biological wiring to stay alive, in order to reproduce.

The human mind is fundamentally wired for survival, not for fulfillment, because humans that stay alive have a better chance at reproducing than humans that find happiness.

”If you think the stick is a snake every time, you’ll be alive. If you think the snake is a stick one time, you could die.”

And these instincts still reside within us, pushing us towards safe, proven paths. And they have merit, because doing what others have done without dying or suffering is a great way to avoid poor outcomes for yourself.

Luckily, in modern times, we aren’t often in that kind of danger when making decisions. Choosing what major to study, what career path to pursue, where to live and what relationships to prioritize aren’t likely to result in life or death outcomes.

But these decisions aren’t easy or objective, and as people grow more and more stressed, confused and apprehensive about making a big life decision, their survival instincts are more likely to be triggered even though they aren’t needed.

A good way to manage your survival instincts is to recognize whenever your intuition is coming from a place of fear – specifically fear of making a bad decision with devastating consequences. It’s well known that humans tend to inflate future pain or pleasure in their imaginations, so by challenging your fear and articulating what exact outcomes you’re afraid of, you will most likely find that you can easily identify and exclude obviously bad choices. This should alleviate the narrow-minded pressure of your survival instincts. However, having such a level of self-awareness can be difficult; both therapy and mindfulness practices can help.


In his 2005 commencement speech at Stanford, Steve jobs shared his story of following his gut and dropping out of Reed College after 6 months only to sit in on classes for 18 more months, including a calligraphy course. At the time it wasn't clear how dropping out of college to sit in on classes such classes would be useful, but 10 years, when Apple launched the Macintosh with beautiful typography, it became clear.

It’s Impossible to connect the dots looking forward, you can only connect them looking backwards. So you have to trust in something – your gut, destiny, life, karma, etc. Believing that the dots will connect down the road will give you the confidence to follow your heart even when it leads you off the well worn path, and that will make all the difference.” – Steve Jobs, 2005

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