Growing up, I was a good kid.
I got good grades. I followed the rules. I didn’t rock the boat. I did what I was supposed to do.
After all, I knew that being good got me praise, approval, and affection. But somewhere along the way, the lines blurred between what I achieved on the outside and how I felt about myself on the inside.
The Good Boy Becomes an Overachiever
Like a lot of ambitious gay men, I became pretty good at achieving things.
I spent 13 years working in corporate leadership before eventually building my own coaching business. It makes sense. I'm responsible, driven, independent, and always looking for ways to improve.
All good qualities, right?
Well, yes. Until they're not.
There's a difference between pursuing something because you genuinely want it and pursuing it because you think achieving it will finally make you feel good enough.
And for a long time, I wasn't clear on which one was driving me.
Back in my corporate days, I remember wanting so badly to get that Senior Manager role. It would mean being the youngest person with that title in my department, and that little tidbit filled me with pride.
So I worked hard, made sacrifices in my personal life, and eventually, I did it. I got the promotion, the raise, and the recognition I wanted so badly.
For a few weeks, I was on top of the world.
But slowly, things started to slide back to normal. The excitement wore off, the new title became old news, and before long, I was already thinking about what I wanted next.
And just like that, the goalposts moved again.
When Success Becomes a Moving Target
Here's something I've noticed about myself, and in many of the men I coach.
We can be incredibly good at recognizing what's missing from our lives while being surprisingly bad at appreciating what's already there.
We get the promotion. Then we want the next one.
We work on our bodies to standards most straight men would kill for. Then we find something else we don't like about them that needs to be “improved.”
Even after everything we’ve done, we’re still convinced that happiness is waiting on the other side of the next accomplishment. It's exhausting.
And the tricky part is that, from the outside, it can look like everything is going great.
I once coached a client who, by almost every measure, had an incredible life.
He lived in a beautiful home he described as his “dream home.” He'd been with his husband for over a decade, and he was at the top of his career. He was in great shape, constantly told he looked years younger than he was, and had friends and family who loved him.
But week after week, he kept coming back to the same thing: he hadn't received a prestigious award in his industry. He was so fixated on this one thing he didn't have that he was barely appreciating everything he did have.
It wasn't that he didn't recognize how fortunate he was. Intellectually, he knew he had a great life. But knowing it and actually enjoying it were two very different things.
The point isn't that he shouldn't pursue the award. It's about why it mattered so much, and what winning it (or not) would mean about his worth.
What Does Being Gay Have to Do With It?
Not every gay man is an overachiever, obviously.
But for some of us, growing up feeling different, inadequate, or afraid of rejection creates an interesting relationship with achievement.
Maybe we couldn't control whether people accepted our sexuality, but we could control our grades, our careers, our bodies, or how successful we became.
Achievement gave us something to feel good about. Something to be recognized for. And sometimes, they compensate for the parts of ourselves we didn't feel so good about.
The problem is that no amount of external success can permanently resolve an internal belief that you're not enough.
You can spend your entire life collecting evidence that you're worthy and still struggle to believe it.
Learning to Enjoy It
One of the biggest shifts in my own life has been learning that I don't have to stop being ambitious to start being content.
I still have goals. I still want to grow. I still get excited about what's next.
But I'm getting better at recognizing when I'm pursuing something because I genuinely want it versus when I'm trying to prove something to myself.
This is actually something we work on at Wellismo through a life skill called Joy & Presence. It's about learning to slow down, appreciate what you already have, and allow yourself to enjoy life without feeling like you have to accomplish something first.
It's also one of the 10 life skills you can explore in my 360° Self-Review, a free tool that helps you recognize what's working in your life and what genuinely needs your attention.
One of the reasons I left the corporate world to start my own coaching business was to have more freedom, flexibility, and independence.
But somewhere along the way, I found myself working just as hard, pushing myself just as much, and putting the same pressure on myself that I'd wanted to escape in the first place.
At times, it felt like I’d built myself another prison. Except this time, I was the boss AND the prisoner.
So a couple of summers ago, I made a deliberate decision to scale back to part-time hours for the summer months. I stripped my work down to the essentials: coaching my clients and writing my weekly newsletter. Everything else, including social media and content creation, went on the back burner.
I could have easily kept growing, building, launching, and improving. Every year, there's a part of me that says, “Keep up or you'll fall behind!” As if I'm in a race to some imaginary finish line. And what exactly does the winner get?
I already know how that story goes…
Now I know that what truly makes my life enjoyable is obligation-free days, spending time in nature, at the beach, on my bike, and soaking up the Canadian summer.
Instead of constantly chasing more, I decided to enjoy the life I'd already worked so hard to create.
Because what's the point of building a life you never actually stop to enjoy?
You Don't Have to Earn Your Own Approval
What if your next accomplishment isn't the thing that's going to make you happier?
What if the work isn't about achieving more, but examining why what you've already achieved never seems to be enough?
That's a big part of the work I do with gay men through Wellismo Coaching. It’s not about helping them become more impressive versions of themselves, but helping them build lives they actually enjoy living… on their own terms.
You've built a successful life. But does it actually feel successful to you?
If you're tired of constantly chasing the next thing and want to figure out what genuinely matters to you, that's the kind of work we do at Wellismo.
Book a free discovery call here: www.wellismo.com/discovery