If you can’t remember the last time you felt proud of yourself, it might be time to say goodbye to these 7 habits

Cole Matheson by Cole Matheson | April 3, 2025, 8:56 pm

If you’ve reached a point where you can’t remember the last time you felt genuinely proud of yourself, you’re not alone. 

Losing that sense of pride can sneak up on us. One day, you’re fired up, working toward your goals, and feeling confident about your choices. 

The next, you realize weeks (maybe even months) have passed without a single moment where you thought, “Hey, I’m actually doing okay.”

If that sounds like you, it might be time to ditch some habits that have been chipping away at your self-esteem. 

Today, we dig into seven of them.

1. Chasing external validation

Ever posted a selfie just for the likes or walked into a meeting hoping someone would say, “Wow, you’re brilliant”? Be honest with yourself here.  

Sure, it feels nice in the moment, but depending solely on the outside world to confirm your worth is a fast track to feeling empty. If that external praise doesn’t come—or it doesn’t come in the way you expect—you’re left deflated and questioning your capabilities. 

I used to do this a lot when I was still in my corporate job. I wanted a promotion or an award or even a simple “good job” to prove that I was valuable. 

But even when I did get a nod of recognition, the feeling was fleeting. I found myself always searching for the next thumbs-up, like an endless hamster wheel of approval.

Here’s the thing: when you anchor your self-worth to your own values, accomplishments, and ethical code, you develop an inner compass that’s more reliable. Relying too much on others to tell you you’re enough will only leave you constantly waiting for applause that might never come.

2. Sticking around toxic influences

This is a big one. Whether it’s the friend who loves to poke holes in every idea you have, the colleague who finds subtle ways to undermine you, or even an online community that thrives on gossip—these forces wear you down over time.

I know this firsthand. There was a phase in my life when I realized that certain people in my life seemed to enjoy highlighting my mistakes more than celebrating my wins. 

It might have been small jabs or sarcastic comments, but they stuck with me. Over time, that negativity seeped into my own self-talk. I’d catch myself thinking, “Maybe I’m not actually cut out for this,” or “They’re right—I probably should just give up.”

The mind has a way of internalizing the voice it hears most often. If the loudest voices around you are telling you that you’re not good enough, it’s only a matter of time before you believe it. Sometimes, distancing yourself from these influences is the first major step to protecting your sense of self-worth.

3. Setting unreasonably high standards

At first glance, aiming for excellence sounds like a good thing. Who wouldn’t want to strive for the best? But when you set the bar so high that it’s impossible to meet, you guarantee dissatisfaction.

Ever stayed up all night redoing a project because you spotted one tiny flaw? Or maybe you’d rather not start at all if you suspect you can’t do it perfectly. This pattern doesn’t just kill your mood; it robs you of the chance to feel proud. How can you celebrate successes if nothing you do is ever quite “good enough”?

This is a tough one to break. For me, the turning point came when I took Rudá Iandê’s “Free Your Mind” masterclass. I wasn’t big on self-development courses before, but I was desperate to break out of my perfectionist mindset. And the course was free, so I thought, why not?

Anyway, the guidance helped me see that I was paralyzing myself by demanding perfection in everything I touched. It was like building a huge wall between myself and any sense of achievement. Once I recognized that, it was easier to let go of my perfectionism, and guess what? I felt a newfound freedom to be proud of the progress I made—even if it wasn’t flawless.

4. Downplaying your successes

How often do you blow off compliments like they don’t mean anything? Maybe you say things like, “Oh, it was nothing,” or “Anyone could do it.” This might seem humble, but it’s often a subtle way of dismissing your own efforts.

If you keep discounting the stuff you do well, you’re basically teaching your brain that your successes don’t matter.

There’s a difference between being humble and being dismissive of your own hard work. Accepting a “Well done!” doesn’t have to turn you into an egomaniac. It’s just acknowledging reality: you did something worth recognizing.

5. Overthinking and self-criticism

If there were Olympic medals for overthinking, I’d have snagged gold multiple times. It’s easy to slip into a headspace where every action or decision is second-guessed. “Could I have worded that differently?” “Did that person interpret my text the wrong way?” “Should I have chosen a different path altogether?”

A little introspection is healthy, but endless rumination is draining. The more you poke holes in your own decisions, the less likely you are to feel proud of anything. You start seeing your life as a series of what-ifs and regrets instead of accomplishments and growth.

It reminds me of a line from the Stoic philosopher Seneca: “We suffer more often in imagination than in reality.” Overthinking is the perfect example of this. You can create problems and negativity in your mind that weren’t even there to begin with. The habit of constant self-criticism piles on top of that, making it next to impossible to feel good about anything you do.

6. Comparing yourself obsessively to others

It’s so easy to look at someone else’s seemingly perfect life and think, “I’m not doing enough” or “I’ll never measure up”, right? But that constant comparison is toxic. You’re essentially comparing your behind-the-scenes footage to someone else’s final cut.

Comparing yourself to others can drive you to forget that you’re on your own unique path, with a timeline that doesn’t have to match anyone else’s. Every time you measure your progress against someone else’s success, you rob yourself of the pride you could be feeling in your own journey.

7. Avoiding challenges and growth

Let’s finish on a big one! It might seem safe to stay in your comfort zone, but that’s exactly where ambition and pride go to die. 

If you never try new things or stretch your boundaries, you miss the opportunity to prove to yourself that you can do hard stuff. Pride often grows when you tackle something tricky, confront your fears, and come out stronger on the other side.

You see, facing a challenge—big or small—is like earning a mental badge of honor. Even if you don’t get perfect results, just surviving the experience can be enough to spark some self-respect. Avoiding tough situations, on the other hand, keeps you from discovering new skills, forging resilience, and feeling that rush of “I did it!” that can fuel a genuine sense of pride.

Stepping outside your comfort zone doesn’t mean you have to go bungee-jumping or spontaneously quit your job. It could be as simple as starting a new hobby, having a difficult conversation you’ve been putting off, or going after a promotion you’ve been too scared to attempt. Whatever the scale, it’s in the act of pushing boundaries that we find the most memorable and proud moments.

Rounding things off

All in all, recognizing these habits—and gently phasing them out of your life—can be a huge game-changer if you’ve been struggling to feel proud of yourself. Sure, it takes consistent effort, and sometimes it’s downright uncomfortable. But shedding the patterns that hold you back is like clearing the path so you can finally move forward.

Remember, pride isn’t about having the biggest trophy or being the loudest in the room. It’s about having an internal sense of worth—knowing you’ve earned respect in your own eyes. It’s totally possible to reclaim that feeling, one step at a time.

So if you can’t remember the last time you felt proud of yourself, it might be time to do a little life-editing. Walk away from toxic influences, compare yourself less, appreciate your wins a whole lot more, and embrace those challenges that scare you just enough to get your heart pumping. 

You might be surprised at how quickly your sense of pride makes a comeback. And when it does, trust me, it’ll be worth all the effort in the world.