How to Make a Big Career Decision (When Every Option Looks Reasonable)

Here is a confession most smart people never make out loud.

The hardest career decisions are not the ones where one option is terrible. Those are easy. You leave the toxic boss. You turn down the job that pays half.

The hard ones are the ones where everything looks fine. The promotion at the company you know. The offer abroad. The start-up with the charismatic founder. The quiet idea of going on your own. You build the spreadsheet, you weigh the columns, you ask six friends, and the numbers come out almost even. So you build another spreadsheet.

I was trained as an engineer at ITU, so believe me, I know the comfort of a spreadsheet. I also know the exact moment it stops helping.

When every option looks reasonable, the problem is not missing information. The problem is that you are asking the wrong question.

Why are career decisions so hard when all the options are good?

The philosopher Ruth Chang has a beautiful answer to this, and she gave it in one of the most watched TED talks on the subject, "How to Make Hard Choices" (2014).

Chang argues that we carry a hidden assumption into every decision. We assume that one option must be better, worse, or equal to the other, the way two numbers on a scale are. If that were true, a hard choice would just mean we haven't measured carefully enough yet. More data, more pros and cons, and the answer would appear.

But in a hard choice, she says, the options are often on a par. Neither is better. They are not exactly equal either. They are good in genuinely different ways. A career in finance and a career in philosophy are not two weights on the same scale.

And here is the part I love. Chang suggests that hard choices are not a failure of reason. They are the place where you get to decide who you are. When the reasons run out, you don't flip into randomness. You commit. You put yourself behind one of the options, and by doing so you create a reason that did not exist before.

Read that again, slowly, if you are stuck right now. The spreadsheet is not broken. It was never meant to make this decision for you.

Is it smarter to keep my options open?

This is where the research gets uncomfortable, because the instinct to keep options open feels intelligent. It feels like strategy.

In 2002, Daniel Gilbert and Jane Ebert published a study in the Journal of Personality and Social Psychology called "Decisions and Revisions: The Affective Forecasting of Changeable Outcomes." Participants chose between photographs they had taken. Some were told their choice was final. Others were told they could swap later.

People strongly preferred having the option to change their minds. And yet those whose choices were reversible ended up less satisfied with what they chose than those whose choices were final. The psychological immune system, as Gilbert calls it, gets to work making peace with a decision only once the decision is actually made. Leave the door open and your mind keeps standing in the doorway.

This is very relevant if you are the kind of person who takes the new job "just to see," while secretly keeping the recruiter warm and the old manager on speed dial.

A half-made decision costs you the benefits of both options and the peace of neither.

I see this often in people with fast, many-sided minds. In FOG OFF, I built the daily pages around exactly this trap. One prompt asks you to name the single decision you keep reopening, then write what you would do if you had to choose by tonight. Fast minds rarely lack options; they lack a place to put the ones they are not choosing today.

What if I choose wrong and regret it?

Fear of regret is the engine behind most stuck career decisions. So let's look at what regret actually does over time.

Thomas Gilovich and Victoria Husted Medvec reviewed the evidence in "The Experience of Regret: What, When, and Why," published in Psychological Review in 1995. Their finding, now widely cited and debated, is that in the short term people tend to regret their actions more, the thing they did that went wrong. Over the long run, the regrets that linger are more often about inactions: the thing they never tried, the door they never knocked on.

Later research has shown this pattern is not universal, and it depends on the kind of decision and the person. Still, it is worth holding in mind. The option that feels safest today is not automatically the option you will feel safest about in ten years.

Then there is my favorite piece of evidence, because it is so delightfully absurd.

The economist Steven Levitt (yes, the Freakonomics one) ran a study published in the Review of Economic Studies in 2021, "Heads or Tails: The Impact of a Coin Toss on Major Life Decisions and Subsequent Happiness." People who were genuinely stuck on a big decision, including whether to quit their job, visited a website and flipped a virtual coin. Heads meant make the change. Tails meant stay.

A surprising number of people actually followed the coin. And six months later, those who had made a change, on important decisions like quitting a job, reported being substantially happier than those who stayed with the status quo.

Levitt is careful about the limits of his sample, and so should we be. These were people who had already been agonizing, which is not everyone. But his conclusion is gently provocative. When we are truly on the fence, we may be systematically biased toward not changing.

If you have been "about to decide" for a year, the status quo is not neutral. It is a choice you keep making by default.

How do I make a career decision without overthinking it?

I have a soft spot for people who overthink. Many of my clients are brilliant, international, multi-talented people, the kind who could succeed in three different careers. That is exactly what makes choosing so painful.

Barry Schwartz and colleagues, in a 2002 paper in the Journal of Personality and Social Psychology, distinguished between "maximizers," who try to find the best possible option, and "satisficers," who look for one that is good enough by their own standards. In their studies, maximizers reported lower satisfaction, more regret and more second-guessing.

So overthinking is not a sign that you care more. Sometimes it is a sign that you have left your thinking alone in a room for too long.

I have a name for this. I call it the Unopposed Mind: a brilliant mind with no one left to disagree with it. It can argue for option A at breakfast and option B by dinner, and both arguments will be excellent. It is not short of intelligence. It is short of friction.

"Life can only be understood backwards; but it must be lived forwards." Søren Kierkegaard, from his journals (1843)

Kierkegaard saw this almost two centuries ago. No amount of analysis will give you the backwards view before you've lived the forwards part.

What about asking AI to decide for me?

Plenty of people now paste their entire career dilemma into ChatGPT at midnight. Honestly, it can be useful. It is a tireless sparring partner, it can lay out scenarios, it can stress-test a plan.

But notice what it does. It gives you answers, beautifully structured ones, on demand. And if you ask it the same question three different ways, it will often give you three reasonable answers. That is not a bug. It is a mirror of your situation. Your options are on a par.

The machine gives answers. The human chooses the question.

Should I take the job in Amsterdam? is a question an algorithm can analyze. Who do I want to become in the next five years, and which of these options asks more of that person? is a question only you can hold.

So how do you actually decide?

Let me give you not a checklist but a few small experiments. Try them on paper, out loud, or on a long walk.

1. Change the question from "which is better" to "which am I willing to be for." Following Chang, ask yourself which option you could commit to with your whole self, knowing it is not objectively superior. Notice which one you start defending when someone criticizes it.

2. Flip a coin, then watch your face. I don't mean let the coin decide (though Levitt's data suggests it would not be the worst thing). Flip it and notice the half-second of relief or disappointment when it lands. That flicker is information your spreadsheet cannot give you.

3. Run the ten-year regret test. Imagine yourself ten years from now, telling the story of this moment to someone you love. Which version of the story makes you wince: "I tried and it was hard," or "I almost did, but"?

4. Set a deadline and close the door. Given Gilbert and Ebert's findings, give yourself a real decision date. After it, stop reopening the file. Let your mind do its quiet work of making peace with the choice.

5. Find someone who will disagree with you. Not someone who will tell you what to do. Someone who will push back on your favorite argument. An Unopposed Mind needs a worthy opponent, whether that is a mentor, a coach or a brutally honest friend.

6. Define "good enough" before you look again. Write three conditions that would make an option good enough for you. If more than one option meets all three, you are no longer choosing between right and wrong. You are choosing between two good lives. That is a privilege, not a crisis.

The question beneath the question

I spent ten years in corporate life before starting my own practice in 2014. Leaving was not a leap; it was a series of small rehearsals, which is the whole spirit of Creative Solutions for Ordinary Problems. I treat a big career question like an experiment you can run on a Tuesday afternoon: try a slice of the new life before you buy the whole thing. The decision gets lighter once it has some evidence in it.

That is the quiet secret of big career decisions. You will not find certainty at the bottom of the analysis. You will find yourself there, waiting for you to decide what kind of reasons you want to live by.

So, here is the question I'd like to leave with you.

If none of your options is objectively better, which one would you choose because of who it would ask you to become?

With love,

Gizem

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