How to Make Hard Decisions Without Regret

Spring 2007, second year at Odessa Polytechnic. I'm walking down four flights of stairs with an F in electrical engineering stamped in my record book. The hallways are empty, everyone's in class, and I'm walking through the sunlight, past the trees outside the windows, feeling exactly one thing: I'm free.

That walk down the stairs was the answer, though I didn't understand it for years. A hard decision stops living in your head and becomes real the moment you stop waiting for total certainty and start living, for just one day, one step, as if you'd already made it. Certainty almost never comes first, it shows up at the end, after a small reversible step, not before it. Wait for it first and you'll wait forever: the mind can weigh the same arguments on a loop and never once get tired.

I've been in business more than twenty years, and I sit across from people making hard calls almost every week, so I hear one line hundreds of times: "I get it logically, I just can't pull the trigger." Making my own call back then cost me my scholarship, my military exemption, and almost a year of silence with my mother, and I'd never call that decision safe. But it's exactly what taught me the two questions that now check any thought that's holding me back, instead of running the same pros and cons in circles.

Why a Decision in Your Head Doesn't Decide Anything

By the time I got that F, I'd already done the math: keep going down the path my parents and the system had picked for me, and by sixty I wouldn't even have basic financial security, a normal apartment, a car, the ability to support kids. The reasons to stay outnumbered the reasons to leave by a mile. Straight-A students didn't get expelled, and staying meant keeping my military exemption, my scholarship (my only steady income at the time), and a status that meant a lot to my family. Logically, everything pointed to finishing school.

And still I doubted, for a long time, right up to the exam. The professor, whose name I honestly don't remember, asked me a couple of questions, I answered them, and then he asked what I actually wanted to do with my life. I said I planned to become an entrepreneur. He asked what I was doing in his classroom, then. I said I needed to finish my degree. He failed me anyway, even though I'd answered everything correctly, and I walked out having lost my scholarship and everything it protected.

Here's the detail nobody mentions in stories like this: that F wasn't my decision. The decision still lived only in my head, someone else's will had just been imposed on me from the outside. The real decision started the second I was walking down those stairs and realized I wasn't going back to argue my case, wasn't going to ask for a retake. I was just walking outside. My head could have doubted for months, running the same math over and over. My feet had already walked out the door.

Two Questions That Test the Fear, Not the Decision

A few years later, once I'd walked dozens of people, not just myself, through decisions like this, I landed on two questions I now ask any thought that's keeping me stuck, before I let it count as real. First: is this a fact or my opinion? Second: does this thought help me or hurt me?

The example that made it click for me: "it's hard to make money in this country." Fact or opinion? I checked where it came from, people told me that, I'd never tested it myself. So: opinion. Does it help or hurt? It hurts, it writes off the attempt before it even starts. If it hurts and it's not a proven fact, I get to stop believing it, even if people have been repeating it around me for twenty years.

The same pair of questions works on doubt before a hard decision, just with a different thought. "I'm not ready yet." Fact or opinion? Usually opinion, readiness is rarely measurable, you either feel it or you don't, and that feeling shifts by the day. It's the same feeling that keeps a perfectionist stuck for years, I wrote about that separately in an article on perfectionism in business. Does it help or hurt? Almost always hurts, because it keeps you exactly where you're already standing. If a thought hurts you and isn't a proven fact, you get to stop listening to it right now, without waiting for it to go away on its own.

How the Decision Became Real, Not Just a Convenient Thought

A week after that F, the dean's office called and asked me to come back. They said I was one of the best in my class, no outstanding debts, why quit over one grade. The dean personally changed my F to a B. I came back Monday for class.

And here's what I usually leave out when I tell this story: I didn't leave right away. I came back, sat through another day, then went about my normal routine for a few more weeks, until one perfectly ordinary Monday, a two-hour block of advanced math, me resting my cheek on my hand, staring out the window, classmates around me asking where I'd disappeared to, and at the break between classes I just walked out and never came back. No drama, no note to explain myself, no second conversation with the dean.

If I'd written this story by the rules of drama, I'd have cut the part where I came back, it ruins the clean line of "made the call and never looked back." What actually happened was the opposite: I came back because the decision wasn't real yet, it only lived in that one free week, not in my everyday life. I needed to sit at that desk one more time, feel that same empty-hallway air from inside a school day, to understand this wasn't about one bad grade or one hurt feeling. The decision became real not the moment I walked out after the exam, but on that boring Monday weeks later, when, with no drama left to fuel it, I simply stood up and walked out.

If you're sitting on an important decision, and you already tried to move once and then backed off like you'd changed your mind, that doesn't make you weak or inconsistent. Often it just means the decision isn't ready yet, and you need one more pass on boring, ordinary material, without the adrenaline of the first attempt — I tell people stuck for this exact reason that laziness, in this sense, doesn't exist, there's only an unchecked thought getting in the way.

What Happened Next, and Why I Haven't Regretted It in Nineteen Years

My paperwork, my diploma, my record book are still sitting in that university. My father had already died by then, never knowing I hadn't given up on the business, only on the degree. A year later, once I was officially expelled, a draft notice showed up instead of an expulsion letter, and that's how my mother found out I wasn't studying anymore. She called it a betrayal. I asked her: if your parents had forbidden you from seeing my father, would you have kept seeing him anyway? She went quiet. Then she forgave me.

At the draft office, I got an exemption as the family's sole provider, my father was gone, and my mother and younger sister were on me now. The exemption turned out to be a side effect of a decision I'd made long before I knew it would change anything with the army.

Nineteen years have passed. I've never once regretted dropping out of that university, even though the logic for staying was real, not invented. It didn't come together perfectly from day one, either: it took roughly two more years, no days off, eight-hour days, before I earned my first thousand dollars, I wrote more about what that grinding stretch actually looked like in an article on discipline. What tested the decision wasn't a conversation with myself, it was what I actually lived day after day, and living it, I never once felt the urge to turn back.

Science Is Mostly on Your Side Here

There's a common belief that the longer you weigh a decision, the less you'll regret it later. Research by psychologist Thomas Gilovich from the 1990s shows the opposite: in the moment, people regret failed actions more, but over the long run, they regret inaction far more, the decisions they postponed and never made(Psyche). A postponed decision doesn't fade painlessly from memory, it builds up and weighs heavier than a failed attempt.

There's also research by psychologists Andrew Parker, Wändi Bruine de Bruin, and Baruch Fischhoff on people called maximizers: instead of a "good enough" decision, they search for the objectively best option available, comparing endlessly and asking everyone for advice.

It turns out maximizers report more regret and end up with worse life outcomes on average than people who settle for a decision that simply works, without spending months hunting for the perfect one(Judgment and Decision Making). It's not about having higher standards for life, the endless comparing itself makes maximizers less satisfied with any option, even the one that objectively turned out better than their neighbor's.

None of this means deciding blindly, with zero analysis. It means the moment to stop analyzing and try the action arrives earlier than your head thinks it does, and the longer you put it off, the more it ends up costing.

The Technology: Two Questions Instead of a Thousand Doubts

These same two questions later closed out my first club, the sale of a company, my exit from projects that had long outlived their purpose.

Nineteen years have passed since that F. My paperwork is still sitting in the university archive. Nobody's ever come to claim it, and I stopped needing anyone to.