Why You Built the Business You're Afraid to Enjoy

Have you noticed that no matter how high your numbers go, in your bank account and in your business, it's still really hard to relax, enjoy it and feel safe?

When we start our businesses, we think: if I hit 10K, I'll feel safe. When I hit six figures. When I hit an eight-figure business. But I keep hearing the same thing from founders, CEOs and executives, and I saw it in my own practice, first as a psychotherapist in Moscow and later in mental health services in the US. Higher numbers don't bring safety.

The insecure overachiever

There's a name for this type: the insecure overachiever. Highly functional, very successful, and still unable to get to the point where he can relax and enjoy the fruits of his labor. He tells himself he just likes working. Maybe there's something underneath that.

High-functioning anxiety is real. So is an anxious attachment to your business. And for gay and bisexual men who run businesses, there's another layer.

What it costs

We started out building a dream, freedom and joy. Then we built ourselves a machine that keeps demanding more and more and more from us, and we don't have a real way to regulate our nervous system. If we keep overfunctioning, we burn out. It spills into our relationships. Our sex life isn't the way we want it.

So here's my question. When your numbers are high and you're not in survival mode, but your brain still can't shut off, what support do you actually have for your nervous system?

The support gap

When I look for support, I want two things.

First, someone who has run a business. I don't care how much money they make. I care that they've been through the high highs and the low lows and know what it's like to be an entrepreneur, whether they're a therapist, a coach or a hypnotherapist.

Second, help from us. I'm tired of coaches and providers whose votes go against our rights while their marketing says they're for everybody. They will never understand the level of anxiety we carry as gay men who are out and building businesses in a political climate this divided.

A rainbow label on a Psychology Today profile isn't the same as expertise. I just earned my SUDPT, a substance use disorder professional trainee credential. You don't need a personal history with addiction to be good at that work. You need real expertise with the people you serve. The same goes for gay men. Somebody feeling aligned with us doesn't mean they're for us.

Money isn't the enemy

We chase leaders for their money, their house, their Instagram. Just because they got there doesn't mean they're the right fit to support you.

And inside our own community, even in the mental health world, we hear that money is bad and CEOs are evil. Some are. But you're a heart-centered entrepreneur who made money. You're not evil. You want to help people. And yet, say "I don't struggle financially" in our community and you may not feel accepted.

Why I opened Good Hypnotherapy

That gap is why I opened Good Hypnotherapy: a practice where gay men who run businesses can learn to regulate. I'm in this too. I'm actively looking for a therapist, a mentor and a coach myself, and with all the parts of my identity, it's hard.

You earned your success. You earned the right to enjoy it.

Tell me in the comments: how do you support yourself? What helps you regulate?

If you want to talk about what support could look like for you, send an appointment request at goodhypnotherapy.org.

This first went out as a letter on my Substack on September 23, 2026. If you would rather get these by email, subscribe there.