Hey mate,
About 6 years ago, I went through a breakup that absolutely wrecked me.
She left, and I found out she’d been cheating.
It was brutal.
But what hurt the most wasn’t just the betrayal—it was the realization that I had completely lost myself in that relationship.
I wasn’t leading.
I wasn’t asserting my needs.
I wasn’t grounded in who I was.
I was people-pleasing, seeking approval, bending over backward to keep the peace… and it hit me: I had been living as a boy, not as a man.
That moment kicked off what I now call a Masculine Awakening—a process of shedding the Nice Guy patterns, stepping into confidence, and finally living with self-respect.
And if you’re feeling shifts in your life right now, you might be going through it too.
Here are five signs you’re in the middle of a Masculine Awakening:
1) You crave female validation less. You’re no longer chasing approval or playing the “nice guy” act to get women to like you. Instead of thinking, How can I impress her? you start asking, Is she the kind of woman I want in my life?
2) You take radical responsibility. The victim mindset fades. You see that your life—your relationships, your career, your happiness—is 100% in your hands. It’s painful, but it’s powerful.
3) You choose growth over comfort. Video games, porn, endless scrolling—they start to feel empty. You crave challenge, purpose, depth. You start asking bigger questions: Why am I here? What impact am I making?
4) You feel anxiety… but with an undercurrent of peace. Instead of running from uncomfortable emotions, you face them head-on. You stop numbing, stop escaping. And in doing so, you start trusting yourself in a way you never have before.
5) You become more decisive. No more overthinking. No more waiting for permission. You start making decisions, leading, and owning the outcomes—whether in dating, friendships, or your career.
If you’re experiencing any of these, mate, know this:
You’re not breaking down—you’re breaking through.
The Masculine Awakening is a rough ride, but it leads to an incredible life: authentic confidence, deeper relationships, and unshakable self-respect.
If you’re ready to fully step into this transformation, I guide men through this exact process inside my Pleaser to Leader program. It’s a 12-week private coaching experience where we take everything we’ve talked about today and apply it to your life in a way that actually sticks.
If that sounds like something you’re ready for, check out the details here.
You in?
Stay courageous,
Oliver
P.S. I’m about to grab a cup of tea and chill for a bit before my next coaching session. If this email resonated with you, hit reply and let me know—where are you in your Masculine Awakening?