7 brutal signs someone will probably regret how they spent their working years

Remember that moment when you realize you've been climbing the wrong ladder?

I spent fourteen years in finance, chasing promotions and bonuses, before I finally understood that success without fulfillment is just well-dressed emptiness. At 37, I walked away from a six-figure salary to become a writer, and while my bank account took a hit, my soul started breathing again.

Looking back, there were warning signs everywhere that I was on the wrong path. I just chose to ignore them, telling myself that sacrifice was noble and that happiness would come later. Spoiler alert: it doesn't work that way.

If you're wondering whether you'll look back on your working years with satisfaction or regret, here are seven signs that might suggest you're heading toward the latter. And trust me, recognizing these signs now is infinitely better than waking up at 65 wondering where your life went.

1. You constantly say "just until..."

"Just until I get promoted."
"Just until I save enough."
"Just until the kids are older."

I lived in the land of "just until" for over a decade. When I started as a junior analyst at 23, I told myself the 70-hour weeks were temporary. Just until I proved myself. But each milestone brought a new "just until," and temporary became my permanent reality.

The psychologist Tal Ben-Shahar calls this the "arrival fallacy" - the belief that reaching some future goal will bring lasting satisfaction. But when you're always postponing fulfillment for some imaginary finish line, you're essentially telling yourself that your present life isn't worth enjoying.

Ask yourself: what exactly are you waiting for? Because if you can't be at least somewhat content during the journey, the destination probably won't fix that.

2. Sunday nights fill you with dread

That sinking feeling in your stomach every Sunday evening? That's your body trying to tell you something.

When I was deep in my corporate years, I'd spend Sunday afternoons getting increasingly anxious about Monday morning. By evening, I'd be stress-eating ice cream and scrolling through job listings I'd never actually apply to. Sound familiar?

While some nervousness about the week ahead is normal, chronic Sunday dread is a red flag.

If you spend 52 Sundays a year feeling miserable about Monday, that's 52 days of your life consumed by dread. Multiply that by decades, and you've lost years to anticipatory anxiety.

3. You've become someone you don't recognize

A colleague once told me, "You used to laugh more." That comment hit me like a freight train.

When work requires you to suppress your values, personality, or authentic self, you're not just doing a job. You're performing an exhausting daily act. Maybe you've become more cynical, more aggressive, or more withdrawn. Perhaps you find yourself doing things that make you uncomfortable, justifying behaviors you once would have condemned.

I remember sitting in meetings, hearing myself speak in corporate jargon that meant nothing, pushing strategies I didn't believe in. Who was this person wearing my face?

The philosopher Søren Kierkegaard wrote about "sickness unto death" - the despair that comes from not willing to be oneself. When your work forces you to abandon who you are, you're not building a career. You're dismantling your identity.

4. Your relationships are suffering

"Sorry, I have to work late again."
"Can we reschedule? Something came up at the office."
"I'm too tired to go out tonight."

These became my catchphrases. Friends stopped inviting me places because they assumed I'd cancel. Family gatherings happened without me. Romantic relationships crumbled under the weight of my absence.

Harvard's Grant Study, which followed subjects for over 80 years, found that relationship quality is the strongest predictor of happiness and health. Not career success, not money, but relationships. Yet how many of us sacrifice our connections for jobs that won't remember our names five years after we leave?

When work consistently takes priority over people, you're not being dedicated. You're making a choice about what matters, and someday, you'll have to live with that choice.

5. You're chasing money at the expense of meaning

There's nothing wrong with wanting financial security. But when money becomes the only metric of success, you've entered dangerous territory.

At 36, burned out and in therapy, I had to confront an uncomfortable truth: I was using my salary to justify a job that was eating me alive. The money had become golden handcuffs, keeping me trapped in a life I didn't want.

Research by psychologist Daniel Kahneman found that beyond meeting basic needs and some comfort, increased income has minimal impact on day-to-day happiness. Yet we sacrifice decades chasing diminishing returns.

When my father had a heart attack at 68, one of the first things he said to me was how grateful he was that I'd left the corporate world. "That stress would have killed you too," he said. No salary is worth your health, your happiness, or your life.

6. You have no energy for anything outside work

Remember hobbies? Remember passion projects? Remember having energy to do something other than collapse on the couch after work?

When your job leaves you too exhausted to live your actual life, you're not working to live. You're barely surviving. During my finance years, I stopped running, stopped reading for pleasure, stopped doing anything that wasn't work or recovering from work.

The tragic irony is that the things we sacrifice for work - creativity, physical health, personal interests - are often what make us better at our jobs in the first place. We become less effective employees by giving everything to employment.

If your job requires all of you, leaving nothing for the rest of your life, what exactly are you working for?

7. You keep waiting for permission to change

"What will people think?"
"It's too late to start over."
"I should be grateful for what I have."

These thoughts kept me stuck for years. I waited for someone to give me permission to want something different, for the universe to send me a sign, for the "right time" to make a change.

Here's what I learned after finally taking the leap: no one else can give you permission to live your life. The right time doesn't announce itself. And being grateful for what you have doesn't mean you have to settle for what makes you miserable.

Bronnie Ware, who worked in palliative care, found that the number one regret of the dying was "I wish I'd had the courage to live a life true to myself, not the life others expected of me."

Final thoughts

If you recognized yourself in these signs, you're not alone. Most of us have been conditioned to believe that work should be hard, that sacrifice equals virtue, that someday it will all be worth it.

But someday isn't guaranteed. What is guaranteed is that you'll spend roughly 90,000 hours of your life at work. That's too much time to spend being miserable, waiting for real life to begin.

Changing course isn't easy. It might mean less money, uncomfortable conversations, or facing fears you've been avoiding. But the alternative is reaching the end of your working years with a retirement account full of money and a life empty of meaning.

You don't need permission to want more from your career than a paycheck. You don't need to wait for the perfect moment to make a change. You just need to decide that your working years should add to your life, not subtract from it.

The question isn't whether you can afford to make a change. It's whether you can afford not to.