Feel like you wasted years of your life? First check what's left of them

Five years in a relationship that ended. Five years building a business that's closing now. Five years chasing a goal that doesn't excite you anymore. Your brain files all of it under one line: five wasted years.

If you feel like you wasted years of your life, check two things: what you have today that you didn't have back then, and whether each attempt changed after the one before it. If your attempts changed, you cleared a level, even if the project closed and the money is gone. If the same attempt went around in circles for years, with no numbers and no lessons, that time really was lost, and it's better to say so out loud. Either way the years aren't coming back. What this check decides is how the next ones go.

I've been through a company collapse and $380,000 of debt to investors, so I'm not here to comfort you. I've spent twenty years in business and, since 2012, I've been doing research and teaching, with more than 2,000 interviews with entrepreneurs. Everything below comes from there.

One caveat. If this thought comes with weeks of apathy and insomnia, or a sense that there's no point in living, put this article down and talk to a doctor or therapist. If it's hard right now, this directory lists free helplines by country. This article is about regret, and depression is treated differently.

Why it feels like you wasted years of your life

I remember how this feeling switched on for me, and it came out of nowhere. I was in my twenties and had spent roughly five years working toward my convertible, the same Mustang I've already written about. I bought it and went to show it off to my mentor, a man I deeply respected and still consider one of the best experts I've ever seen. He said one sentence: "You do understand it's not about the car." It hit me hard, because it felt like he had just wiped out all five years. And I had reached the goal. So the thought "those years were wasted" shows up after failure and after victory, whenever a goal suddenly stops being the main thing.

I think the habit of judging ourselves this way starts in school, where a mistake meant criticism and a verdict on all your effort. You flunk a test, so all your work was worth nothing. That's why an adult sees a project ending and feels like they got an F for five years of life. A mistake is really just an attempt that showed a specific mechanism doesn't work.

Psychologists Thomas Gilovich and Victoria Medvec, pulling together the data on regret, found a pattern over time: in the short run what you did hurts more, and in the long run what you didn't do hurts more. That's an average across people and it can't predict your story, and it cuts both ways. If you tried and got burned, the sharp pain usually fades. If you spent years not daring to leave or start, this data gives you no reason to expect it to pass on its own.

Wasted years or a level you cleared: how to tell

A cleared level is a period that gave you a skill, connections, or understanding you couldn't have taken the next step without, even if the period itself ended in failure. Wasted years look different: time went by and the person is doing exactly what they did at the start.

I won't tell you that "everything happens for a reason," because that isn't true. A man once came to me and said, "I've been in network marketing for five and a half years, I have three people on my team, Igor, help me." I asked one question: how many meetings did you hold last week? Three people don't mean much by themselves. In two years at Amway I signed up two. What matters is the answer about last week. There's a popular line: if you can't walk toward your goal, crawl, and if you can't crawl, at least lie down facing it. It sounds motivating, and it's exactly how years get lost. You haven't given up, the hope is still alive, you can't call yourself a quitter, and in fact you aren't moving.

	A cleared level	Wasted years
Attempts	Each one differs from the last	The same attempt on repeat
Numbers	You have them: meetings, deals, clients	Nobody counted
Mistakes	You can name three and what came of them	"Bad luck," "that's the market"
Today	You do what you couldn't have done five years ago	You do the same thing at the same speed

The best study I know on this ran in Nature in 2019. Yin, Wang, Evans, and Wang tracked repeated attempts in three very different fields: NIH grant applications, startups, and attacks by terrorist organizations. People who eventually succeeded and people who didn't look alike at first, and they start to diverge as early as the second attempt. What separates them is how much the next attempt uses the lessons from the last one. This is data about specific attempts and not about years of life, and it only covers those who tried again, so applying it to your life is my step. As a working rule it beats "how many years did I waste," because you can answer "how was my second attempt different from my first" with facts.

So here's my benchmark. If you've been training for two years and the weight isn't coming off, you go to a specialist. Same with wasted years on your business: if your numbers haven't moved in two years and you never changed your approach, find an entrepreneur in your city who's ahead of you and ask for advice. The time span alone proves nothing. My first club took exactly two years to reach decent money, but it did reach it. Sitting there three more years to be completely sure is how you actually lose them.

What you can't get back: an honest count

I'll start with the unpleasant part. The years won't come back. If a closed project cost you money, your health, evenings with your kids, or an opportunity that won't open again, that's a real loss, and grieving it is normal. My number is public: GrafSpace ended in February 2018 with $380,000 of debt, and I wrote separately about how I got out of it. No amount of rethinking the past cancels sums like that.

That's why I suggest keeping two accounts. The first holds the price: time, money, what you missed. It's closed, and it shouldn't influence decisions about the future. The second holds what moves with you: skills, people who'll pick up the phone, understanding of the market and of yourself. The confusion starts when these two get mixed, and then you either pretend there was no price or the price blinds you to what you took away.

What's left of those years: my own account

Here's the second account in my own numbers. I spent about two years at Amway. In all that time, two people joined my organization, and I didn't miss a single seminar. There's not much money to count there, but that's where I learned how to learn and how to sell when it isn't working, and that skill still feeds me today. By the table above that's a level, even though from the inside it looked like failure.

At twenty I raised $32,000 from an investor for a PlayStation club, and reaching $3,000–4,000 a month took exactly two years: a young kid with no knowledge, no courses, and no mentor. I sold the chain in 2012 for $125,000. That same year I started selling elite kittens and made $4,400 clear in the first three weeks, from zero, from idea to money. I started a video production company and got $3,000 in the first month.

It's a rough comparison. The businesses are different, and the club earned every month while these were first orders. The gap in timing is still plain: two years to the first decent money and three weeks to similar money. Once you know how to do business, you get there fast. That's how the bill for past years arrives, at your next launch, and you can't see it from inside a project that's closing. In my failed 2018 I earned money using a start-from-zero business strategy, which is what those earlier launches had taught me.

Is it too late to start over if the years went to a job or a relationship?

The same questions work outside business, and they're how I'd handle career regret too. Ten years in a job: did your responsibilities and your price grow, or did you live the same year ten times? A marriage that ended: did the conversation change or did one fight go in circles, and what would you notice sooner now? A dropped PhD: the method and the discipline stay with you, and so does knowing that this work isn't for you. Nobody can answer these for you, but the answers have to be facts all the same.

About age. People assume it's too late after forty. Pierre Azoulay and his coauthors studied US Census Bureau data: the average founder of the fastest-growing new companies, the top one in a thousand, was 45. That number doesn't erase your health or your obligations to your family, and at fifty your reserve of money and energy is different, so your attempts have to be cheaper. But the data doesn't support the idea that everything gets decided before thirty.

Why your old approach stopped working even though it brought you here

When I was creating PERL, my pyramid of the stages of personal development, one thing surprised me: some tools work only in their own period and stop working in the next. What saves a company at one stage can wreck it at another. So when an adult entrepreneur looks back five years and says, "What an idiot I was, I should have built a system right away," he's often wrong. With that team and that money, a system could have killed his business. There are also plain mistakes with a price at any stage, and the table above separates those out.

Back in 1972 Larry Greiner described something similar for companies: a growing organization goes through five phases, calm growth in each one ends in a management crisis, and a major solution from one period becomes a major problem in the next. He wrote about organizations, and applying it to a person is my analogy.

Here's the second trap: looking at a millionaire and deciding you should have done what he does from day one. You're looking at the final version, and success is a series of stages. Take someone carrying a lot of extra weight, with bad joints, and make them train like a world bodybuilding champion right away. You'll kill them. They should be walking and doing squats, and even then it's an open question whether the joints will hold. In business, for some reason, we want to train with millionaires right away, and then we beat ourselves up over years that were really our squats. That route through the stages is why we built Freeman's Alliance.

How to stop regretting wasted years: look at them like an electrician

Push a little more voltage through a circuit and a fuse blows, and right away you can see the weak spots in the wiring. That's what you pay an electrician to find. I'm at a stage now where I'd pay good money to have someone show me where I'm shorting out. But when we find a spot like that in our own lives, a limit around money, sales, recognition, we get upset, even though it's the most valuable thing we could find: now it's clear which wall to open and which cable to replace. Years that ended badly are almost always a test like this under load, and they're worth taking apart like a wiring diagram.

Five steps, for one evening with a sheet of paper:

1. Name the period in one line. No judgments: "2019–2024, design studio, two partners, closed." As long as it's "five wasted years," there's nothing to work with.
2. Write down what you have now that you didn't have then. Skills, people who'll pick up the phone, numbers you now know, mistakes you won't repeat. If you get stuck, ask someone who knew you at the start of that period to write it for you, because in this state we rate ourselves worst of all.
3. Run the second-attempt test. How was your second try different from the first, and your third from the second? If it wasn't, you've found the real problem, and it lives in the present tense.
4. Find where it shorts out. One line: what did everything keep running into? Sales, money, partners, fear of being seen, a conversation you keep avoiding. That's your theme for next year.
5. Within seven days, take one step on that cable. A talk with someone a level above you, ten meetings, going through your numbers, booking a specialist. After action, regret turns into a plan.

If the question is whether to quit your business now, after all those years, remember what psychologists Arkes and Blumer called the sunk cost effect: the more money, effort, and time you've put in, the stronger the pull to keep going. Ask yourself: if I walked in here today, without those five years behind me, would I start this? I go deeper on these forks in how to make hard decisions without regret.

How many failures before success: 35 in a row and Marvel

There's no honest number, and 35 is just an image I use. Movies with hundreds of millions of dollars behind them, the best stars, and the best marketers flop every year at the strongest studios. The question is how many failures you can afford: you can make 35 in a row, run out of money, and go bankrupt. So what you count is your budget for mistakes, how many attempts your money and your head can take, and you make each next one cheaper and smarter. I have a separate piece on that, and it's also why I always show my own screwups: I lose money, get back up, and make mistakes again.

Marvel filed for bankruptcy in December 1996, and in 2005 it took a $525 million loan against the rights to ten characters so it could make movies itself. In 2008 Iron Man grossed about $585 million on a $186 million budget. Take the comparison with a grain of salt: this is survivorship bias, Marvel had characters the whole world knew, and the ones that didn't make it don't get articles. I bring it up for one reason: the new attempt was different from the earlier ones, and it came twelve years after the bankruptcy, years when nobody could see how it would end.

What I finally understood about those five years

My mentor was right, it isn't about the car. That didn't wipe out the road. The road brought me to the point where the car stopped being the main thing, and the skills from that game stay useful, while the next game puts others in first place. Without those five years I couldn't have heard that sentence at all.