Regret is one of the worst feelings to live with. It sneaks up when you realize that the choices you made—or didn’t make—led you somewhere you never wanted to be.
The truth is, that unsuccessful people don’t end up that way overnight. It’s often a series of habits, mindsets, and decisions that slowly push them toward a life they later wish they had lived differently.
Psychology shows us that certain behaviors almost guarantee regret down the road. The good news? Once you recognize them, you can avoid making the same mistakes.
Here are 10 things unsuccessful people do that lead to regret later in life—and how you can steer clear of them.
1) They wait for the “right time” to start
A lot of people have big dreams, but unsuccessful people tend to spend their lives waiting for the “perfect moment” to begin. The problem? That moment never comes.
Psychologist William James once said, “Nothing is so fatiguing as the eternal hanging on of an uncompleted task.” And he was right—procrastination doesn’t just delay success; it drains your motivation and confidence over time.
People who look back with regret often realize they spent too much time hesitating, overthinking, or making excuses instead of taking action. Life doesn’t wait, and neither should you.
If you want to avoid this mistake, stop waiting for the stars to align. Start where you are, with what you have, and figure things out along the way.
2) They let fear of failure hold them back
I used to be someone who avoided anything that felt like a risk. If there was a chance I might fail, I’d find a reason not to try at all. I told myself I was being “smart” or “practical,” but deep down, I knew the truth—I was just scared.
Looking back, I regret the opportunities I let slip away because I was too afraid of things not working out. And the irony? Avoiding failure didn’t protect me—it just kept me stuck.
Psychologist Carl Jung once said, “I am not what happened to me, I am what I choose to become.” That quote changed the way I saw failure. It made me realize that setbacks don’t define you—your response to them does.
Unsuccessful people let fear make their decisions for them. But the people who live without regret? They take risks, make mistakes, and keep moving forward anyway.
3) They surround themselves with the wrong people
It’s harsh but true: the people you spend the most time with will either push you forward or hold you back. And unsuccessful people often don’t realize how much their environment is shaping them until it’s too late.
I’ve been there. I’ve stayed in friendships that drained me, listened to advice from people who had no idea what they were talking about, and ignored my gut when it told me I was in the wrong crowd. Looking back, I regret every moment I spent trying to fit in with people who weren’t growing.
If you surround yourself with negativity, doubt, or small-minded thinking, that’s exactly what your life will reflect.
Unsuccessful people don’t cut ties when they should. They hold on to toxic relationships, stay in unfulfilling circles, and let other people’s limitations become their own.
If you don’t want to regret where you end up, take a hard look at who’s walking that path with you.
4) They ignore their own potential
For a long time, I downplayed my own abilities. I’d have ideas but assume they weren’t good enough. I’d see opportunities but convince myself someone else was more qualified.
The truth? I was holding myself back more than anyone else ever could.
Unsuccessful people do this all the time. They underestimate themselves, settle for less, and never push beyond their comfort zones.
And the worst part is, they don’t even realize the damage they’re doing until years later—when regret starts creeping in.
If you don’t want to end up looking back and wondering what could have been, start believing in yourself now. Take the risk, develop your skills, and stop waiting for permission to go after what you really want.
5) They chase happiness instead of meaning
It sounds strange, but one of the biggest mistakes unsuccessful people make is prioritizing happiness over meaning. We’re told to “do what makes us happy,” but the truth is, happiness is fleeting—what really keeps people fulfilled in the long run is having a sense of purpose.
I’ve had moments in life where I chased short-term happiness—avoiding discomfort, seeking instant gratification, and thinking that an easy life would be a satisfying one.
But the times I’ve felt the most fulfilled? Those were the moments when I was challenged, pushing through struggles, and working toward something bigger than myself.
Unsuccessful people often regret spending too much time chasing pleasure instead of purpose. They avoid difficulty, only to realize later that the real joy in life comes from struggle, growth, and contribution.
If you want to look back without regrets, stop asking, “What will make me happy right now?” and start asking, “What will make my life meaningful?”
6) They avoid difficult conversations
Nobody likes uncomfortable conversations. Confrontation is awkward, setting boundaries feels harsh, and telling the truth—especially when it’s not what someone wants to hear—can be terrifying. But avoiding these conversations? That’s a guaranteed path to regret.
Unsuccessful people often stay silent when they should speak up. They tolerate bad relationships, accept unfair treatment, or let resentment build just to keep the peace. But in the long run, avoiding tough conversations doesn’t prevent problems—it just makes them worse.
Psychologist Brené Brown put it perfectly: “Clear is kind. Unclear is unkind.” It’s easy to think that sparing someone’s feelings or ignoring an issue is the “kind” thing to do, but in reality, honesty—delivered with respect—is real kindness.
The people who live without regret are the ones who say what needs to be said, even when it’s hard. They ask for what they deserve, set boundaries without guilt, and have the courage to face uncomfortable truths.
If you don’t want to look back wishing you had spoken up, start practicing tough conversations now—you’ll be glad you did.
7) They prioritize comfort over growth
For a long time, I thought success meant finding a place where everything felt stable and easy. I avoided challenges, stuck to what I knew, and told myself that as long as I wasn’t struggling, I was doing fine. But over time, “fine” started to feel frustrating. I wasn’t failing—but I wasn’t growing, either.
Unsuccessful people often make this mistake. They choose the path of least resistance, avoiding anything that feels uncomfortable or uncertain. But here’s the problem: growth only happens outside your comfort zone.
Psychologist Carol Dweck, known for her work on mindset, once said, “Becoming is better than being.” In other words, the process of learning, evolving, and pushing yourself is far more fulfilling than simply staying where you are.
The people who look back with regret aren’t the ones who tried and failed—they’re the ones who never tried at all. If you want to avoid that feeling, start embracing discomfort now.
Lean into challenges, take on things that scare you, and remind yourself that real success isn’t about staying comfortable—it’s about becoming more than you were yesterday.
8) They let past mistakes define them
I’ve made mistakes that kept me up at night. Bad decisions, missed opportunities, moments where I knew I could have done better—but didn’t. For a long time, I let those mistakes weigh me down, convincing myself that they were proof I wasn’t good enough or capable enough to move forward.
Unsuccessful people do this all the time. They dwell on past failures, replay their worst moments, and let shame keep them stuck. But here’s the truth: Regret only has power over you if you let it.
The people who succeed aren’t the ones who never mess up—they’re the ones who refuse to let failure define them.
If you don’t want to look back on a life filled with regret, stop carrying mistakes that no longer serve you. Learn from them, own them, and then let them go.
9) They focus too much on goals and not enough on systems
We’re always told to set big goals—land the dream job, make a certain amount of money, hit a major milestone. But here’s the counterintuitive truth: unsuccessful people often focus too much on goals and not enough on the daily systems that actually create success.
I used to obsess over big-picture achievements, thinking that if I just set the right goal, everything else would fall into place.
But over time, I realized that goals are useless without consistent habits. You don’t rise to the level of your ambitions—you fall to the level of your systems.
Unsuccessful people regret spending years chasing goals without creating the structure to support them. If you want real progress, stop fixating on the outcome and start focusing on the process. The small habits you build today will determine where you end up tomorrow.
10) They ignore their mental and emotional health
For a long time, I thought pushing through stress and burnout was just part of life. I ignored the signs that I was mentally drained, told myself to “tough it out,” and believed that slowing down meant falling behind.
But in the end, neglecting my mental health didn’t make me stronger—it made everything harder.
Unsuccessful people often make this mistake. They prioritize work over well-being, suppress their emotions instead of dealing with them, and convince themselves they don’t have time to take care of their minds.
But here’s the truth: ignoring your mental and emotional health doesn’t just affect you—it affects everything you do.
Psychologist Carl Rogers once said, “The curious paradox is that when I accept myself just as I am, then I can change.” True growth doesn’t come from beating yourself up or pushing yourself past your limits—it comes from self-awareness, self-care, and the willingness to acknowledge what you need.
If you don’t want to look back with regret, start taking your mental health seriously now. Rest when you need to, seek help when necessary, and remember that success is meaningless if you’re too burned out to enjoy it.
