Real stories. Real lessons. No filter.
This isn't a blog. It's the part most people leave out — the jobs that shaped the thinking, the mistakes that cost real money, the moments that changed everything. These are the stories behind Headway, told the way they actually happened.
Every lesson on this site came from somewhere. The Founder's Journal is where those somewhere stories live. New entries publish as they're ready — not on a schedule, but when a story is worth telling.
I walked into my first mortgage client meeting with six or seven proposals, every scenario mapped out, ready to impress. I left without the sale. The lesson that followed changed the way I sell everything.
He was the kind of man you wanted to learn from. Successful, well-spoken, respected. And one afternoon he told me that money was dirty. I've been unpacking that conversation ever since.
The Founder's Journal is one person's road. But the road looks different for everyone. If you have a story — a turning point, a lesson that cost you something, a moment that changed how you see money or work or yourself — we want to hear it.
Submit Your Story →Subscribe and get a free e-book that proves what we believe — that investing in yourself is the most powerful economic decision you will ever make.