Heartwood Agency

Why I’ve stopped chasing confidence

For a while, I thought confidence was the key to overcoming imposter syndrome. If I could just feel more confident, everything else would fall into place.

Then I saw a post from Gary Vaynerchuk that stuck with me:

“Impostor syndrome is just a...

“Welcome to leadership — we’re all making it up.” I remember telling my former boss, “I feel like I have no idea what I’m doing. Like I’m just making it up every day.” He smiled and said, “Welcome to leadership. We all feel like we’re making it up every day.” This week, I saw...

I thought 25 years in tech had prepared me to be a founder. I was wrong.

For 15+ years, I managed teams and led projects. I thought I understood how businesses worked. But stepping into the founder role changed my perspective.

- As an individual contributor, I solved technical...

Chaotic. Anxiety-inducing. Exciting. That’s what the first 90 days of Heartwood Agency felt like.

When I was suddenly out of a job, I did the only thing I knew: kept showing up. The next morning I went to the office like it was a normal day. No plan—just momentum.

Those early...