How to Use Your Gut (When Logic Fails)

I initially felt stupid for turning it down.

In front of me was the biggest offer of my life. Better title. More pay.

It was what I wanted, right? So why did I feel a massive wave of relief after turning it down?

If you’ve ever faced a hard fork in the road, this is my story of deciding between two career paths. After talking to friends, I realized that the process I went through was beneficial in helping them solve a number of dilemmas, like…

  • Evaluating job offers
  • Choosing to date someone versus staying single
  • Making a choice between two (or more) attractive options.

If there’s a dilemma waging war inside your head, you’ve come to the right place.

The Dilemma: Entrepreneurship vs Office Job

One road was taking the job offer in front of me.

The other road was continuing on a confusing path of entrepreneurship and internet marketing.

So I did what every nerd does: use an excel spreadsheet to analyze my decision.

I did a side by side comparison with variables like freedom and compensation.

And after analyzing the situation to death…it came out to a tie

  • While I would earn more money by taking regular job in the short term, I have enough savings and am generating some income from entrepreneurial efforts.
  • I’m willing to sacrifice some freedom for work experience…and I was also willing to sacrifice having a “good resume” to maintain my level of freedom
  • The job will make me more money, and more consistently, compared to my own efforts… at least in the beginning. But there was the promise of making more money, on my terms.

I ended up back at square one. What to do?

Turning to my gut

Special shout out to my friends Lauren and Jeremy, who asked me the question: are you making a decision from a place of courage or fear?

This question gave me a visceral reaction. Emotions like fear, shame, and exuberance came rushing in.

This strong reaction made me realize that I was ignoring my gut – my emotions – in the decision making process.

The question is, how do I use my gut?

By feeding it the right questions. Ones that elicit an emotional response, rather than a completely logical one.

by Gerd Leonhard

Of all the questions I asked myself, these three gave me the most clarity – and helped me turn that fork in the road into a honest decision. Here goes:

1) Measuring by Regret


“What decision would you regret more in the future?”
“Which path would lead to less regret?”

The unexpected value of regret was that it forced me to think long term. It brought me out of the false urgency of the present dilemma, and made me question what outcome would be best for my future self.

Example: I thought of myself old and gray in some hospital bed, and I find an ancient Google Drive file containing my bucket list items. I knew I would be full of regret if I didn’t travel the world, developed meaningful relationships or lived my life according to someone else’s values.

2) Measuring by Relief


“What outcome would make you feel relieved, and why?”
“Which decision would give you more or less stress?”

The feeling of relief can be a proxy to clarity. If giving up one option provides massive relief, then that means there’s an emotional attachment to some outcome that begs examining.

Example: there’s a message you want to tell a loved one, but you can’t bring yourself to do it. Imagine – would you feel massive relief after sending the message? That should tell you something.

Measuring by relief doesn’t mean choosing options that stress you out less (stress is essential for growth). Rather, it’s the start of an inquiry – why would I feel such massive relief after choosing one option or another?

3) Measuring by Honesty


“Which decision feels more honest?”
“Which decision feels more forced, or not true to yourself?”

We all know the feeling of forcing something. It feels fake. It doesn’t feel genuine. It’s different from the discomfort of going outside your comfort zone. Rather, it’s the feeling of violating your values.

Example: Someone’s really into you, but you’re not attracted to them. But you don’t want to reject them by hurting their feelings, so you continue spending time with this person – or consider ghostin’. Would you feel more honest if you communicated how you really felt?

Measuring by honesty helps me reconnect with my values: What do I care about in this world, am and I upholding that with this decision? Because if it doesn’t feel honest, then it probably violates my values and I should explore alternatives.

Finally landing on a decision

By asking myself different questions, I got answers that were worlds apart from the output of my Excel spreadsheet.

I realized that lining up the variables and comparing the pros & cons worked with tangibles like choosing which car to buy, how to allocate investments.

Intangibles involve matters of the heart like changing careers or navigating romance. These issues are deeply rooted in emotion.

And at the root of it all, my decision making was steeped in fear.

I was making decisions based on how I felt about my self worth, which was low at that moment.

If you find yourself in a similar spot, consider this…

Make a decision with your whole heart; not with the hole in your heart.

And just for fun, I replaced some of the variables on the original spreadsheet with “emotional” factors. Here’s what I got:

Factoring in variables like regret and honesty, one decision beat out another by a factor of 2 to 1.

The Value of Good Questions

Personal growth is all about asking yourself the right questions. These questions have, and continue to serve me tremendously at major life decision points, forks-in-the-road.

I used to separate logic and emotions at different scales:

Now I’m starting to appreciate how they can intertwine on the same spectrum of decision making:

The takeaway? Incorporate emotionally-based self questioning for major decisions.

Extra credit: mo’ good questions I like

  • If you won the lottery, how would you spend your day? Which action now gets you closer to that?
  • What would the bravest, most courageous version of you do?
  • What would a future you wish you did right now?
  • You’re old and on your deathbed. What would be your biggest regrets?

Got a great question to share? Please comment – I’d love to know.

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