I’ve been wasting my 20s on trying to please everyone — here’s what I’d do differently today

I used to believe I could make everyone around me happy.

It felt like a kind of mission: if I could keep the peace, avoid conflict, and always present myself as agreeable, then life would run smoothly.

That approach seemed noble at first, but I didn’t realize how much of my own identity I was giving up.

All those years of politely saying “yes,” grinning through disagreements, and bending over backward chipped away at my sense of self.

I’m in my mid-40s now, and the more I look back on my 20s, the more I see how being a people pleaser became my default mode. It drained me emotionally, left me confused about who I was, and created a pattern where I felt responsible for everyone’s comfort but my own.

Let me be clear: wanting to be kind isn’t a problem. It’s when kindness morphs into relentless self-sacrifice that it becomes toxic to your own growth.

There was a moment in my late 20s when I realized I’d become the guy who would rearrange his entire schedule for a vague “maybe” from a friend.

That’s when I started to question if I had any boundaries left.

Today, I’m sharing my story because it’s easy to fall into the trap of seeking validation from everybody, especially in your 20s. I’d like to walk you through the lessons I’ve learned and what I would do if I could rewind the clock.

How it all started

When I was growing up in Australia, mealtime conversations often revolved around big questions.

My father, a philosophy professor, would encourage us to question everything, while my mother, a therapist, emphasized empathy.

That combination made me curious about human nature, so I was always reading psychology books and studying the ways people interact.

But ironically, this same interest made me hyper-aware of other people’s emotions, to the point where I felt like I had to fix them.

In my 20s, I began to equate love and acceptance with compliance. If someone was upset, I would drop my own needs and do whatever it took to relieve their discomfort.

Looking back, I see that my behavior was rooted in fear: I worried that if I didn’t please people, they’d walk away. That fear was never explicitly stated, but it lingered in the background of my interactions.

This was the start of a pattern that would define my entire decade.

I said “yes” to dinner invites I couldn’t afford, volunteered for tasks at work that weren’t mine to handle, and adjusted my personality to fit every crowd.

Why this pattern was so destructive

The trouble with trying to please everyone is that you can never fully succeed. There will always be someone who disapproves or wants more from you.

Over time, I noticed my self-worth was tied directly to external feedback.

If friends or colleagues were happy, I felt accomplished. If they expressed even slight disappointment, I took it personally.

Psychologist Carl Jung spoke about the concept of the “persona,” the face we show to the world.

In my 20s, my persona was that of an ever-smiling, ever-accommodating person, but behind that façade, I felt drained and increasingly unsure of who I actually was.

The biggest blow came when I realized I was chasing approval without considering my own values. I had set aside things I cared about—philosophy, creativity, and exploring new ideas—to maintain a perfect social scorecard.

Eventually, I grew resentful.

There were nights I’d come home and wonder if anyone truly knew me or if they only knew the version of me who was so eager to please.

Recognizing the hidden cost

It took a long time to see that I was neglecting myself.

In the short term, giving people what they wanted created a sense of harmony, but in the long run, it was suffocating.

I wasn’t just losing time — I was losing myself.

I compromised on my ambitions and relationships that didn’t align with my core values.

When I started traveling as a digital nomad, I saw how deeply ingrained my pattern was. I’d be in a new country, yet I’d still fall into the same routines—putting everyone else first, even total strangers I had just met.

It hit me that location changes nothing if you don’t shift your mindset. You can’t outrun your own tendency to say “yes” at your own expense.

I realized I wasn’t just trying to make people happy; I was also avoiding the discomfort of saying “no.”

That discomfort, I discovered, was necessary for establishing a genuine sense of self.

The moment of truth

I reached a point where I was tired of hearing myself agree to things I didn’t care about. It was a real wake-up call to notice how often I spoke and acted purely to blend in.

I remember turning down a job opportunity that looked good on paper but went against everything I believed in. Even though it felt scary, that decision was a small but significant step toward authenticity.

Philosopher Søren Kierkegaard once said, “Once you label me, you negate me.”

I think of that quote often because I felt labeled as the “nice guy,” the person who would do anything to keep the peace.

Learning to reject that label meant facing my own discomfort. I had to practice setting boundaries and risk being seen as difficult or self-centered.

At first, it felt like I was letting everyone down.

But gradually, I discovered that people who genuinely cared about me respected those boundaries.

Building genuine connections

Once I started being honest about my opinions and desires, the quality of my relationships changed. Old friends who had been taking advantage of my people-pleasing tendencies faded away.

The friends who remained were the ones who valued me for who I was, not for my ability to keep them happy.

It’s amazing how much lighter life becomes when you don’t have to maintain a persona.

I also noticed that my professional life improved. When I chose projects that resonated with my values, I did better work, and I was more enthusiastic.

If I could re-live my 20s, I’d invest that decade in learning to connect with people on an honest level. Instead of “pleasing” them, I’d aim for genuine understanding, even if it meant occasional disagreements.

Practical steps I wish I had taken

It’s one thing to say “stop pleasing everyone,” but another to know how to pivot. I wish I had dedicated time to figure out my non-negotiables—those values I wasn’t willing to compromise on.

I’d encourage anyone in their 20s to write down five core values and refer to them whenever a decision comes up.

No need to overcomplicate: it could be creativity, independence, loyalty, or anything that truly matters to you.

Brené Brown’s work on vulnerability taught me that authenticity requires a level of risk.

Admitting I wasn’t always okay or that I had different interests from my social circle felt risky at first.

If I had known how liberating it is to admit I don’t have everything figured out, I would’ve done it earlier. There’s tremendous freedom in letting people see the real you—flaws and all.

Standing up for yourself without guilt

Another skill I wish I’d developed sooner is learning to say “no” without remorse. I used to dread turning people down because I assumed they would think less of me.

But saying “no” to others often means saying “yes” to your own priorities.

That’s where real self-confidence begins to form.

A friend once told me, “When you say no, you’re honoring the moments in your life.” That phrase stuck with me and helped me see that boundaries protect both my time and my sense of purpose.

The guilt started to fade when I realized that the right people will respect a well-placed “no.” It’s the ones who react negatively that reveal they might only value what you can do for them.

Trusting the process of self-discovery

Being genuine isn’t always comfortable, especially if you’re used to pleasing people. It might feel awkward to express an unpopular opinion or to speak up when you disagree.

But every time you stand your ground, you build a deeper relationship with yourself.

You start to trust your instincts and realize you have an inner compass worth following.

In my 20s, I kept looking outward for approval, thinking I needed others to confirm my worth. If I could do it again, I’d spend more time doing things like journaling, meditating, and reflecting.

That inner work doesn’t have to be complicated.

Even just taking a walk alone and asking yourself, “What do I really want today?” can open up a new layer of self-awareness.

Nurturing authentic self-worth

True self-worth doesn’t come from external applause.

It grows when you learn to be proud of who you are and the choices you make, independent of external validation.

When I first launched Ideapod, it was a response to what I saw as a lack of meaningful conversation in mainstream media. That drive was authentic, fueled by curiosity and a desire to spark insightful dialogues.

But in other areas of my life, I was still playing the old role of people pleaser.

I discovered that you can be bold in one area—like starting a new venture—and still hide behind a facade in your personal relationships.

Merging those two aspects meant accepting that I can’t be everything to everyone. I had to be okay with the fact that some people won’t connect with my views, and that’s perfectly fine.

Conclusion

I look back on my 20s with a mix of regret and gratitude.

Regret because I sacrificed so much of my own identity to gain approval, and gratitude because I now see how crucial those years were for my growth.

If I could whisper advice to my younger self, I’d say:

• Define what truly matters to you early on.
• Stand firm in your beliefs, even if they conflict with what everyone around you thinks you should do.
• Focus on building real connections rather than artificial harmony.

Disagreements and disappointments are inevitable, but genuine friendships will survive those rough patches.

So, give yourself permission to say “no” when something doesn’t align with your values. Don’t be afraid to walk away from people who refuse to respect your boundaries.

Take the time to explore your inner world instead of constantly seeking external validation.

The only way to find your voice is to hear it first, before letting the outside noise shape it.

In the end, living authentically is worth every uncomfortable conversation. It frees you from the burden of meeting everyone else’s expectations and opens the door to deeper self-awareness and true fulfillment.