Why I Created Dear Solopreneur

There’s a gap on the bookshelf. On one side, the weighty business tomes full of frameworks, financials, and five-year plans. On the other, the self-help titles promising calm, clarity, and confidence. But what about the messy middle? The sleepless nights. The 2 a.m. cold sweats. The loneliness of building a business when the world’s asleep and the bills don’t stop coming. That’s where Dear Solopreneur was born.

The Problem No One Talks About

Entrepreneurship can be exhilarating. It can also be exhausting, isolating, and downright terrifying. You can have all the spreadsheets and strategy documents in the world, but they won’t sit with you at 2 a.m. when you’re asking yourself:

• Am I really cut out for this?
• What if I fail and everyone sees?
• Why does this feel so lonely when I thought freedom would feel amazing?

Business books rarely go there. They’ll tell you about KPIs, ROI, and market positioning, but they won’t whisper in your ear when doubt creeps in. Self-help books, on the other hand, might soothe your spirit but rarely give you the grounded, practical advice to fix the cashflow or deal with a difficult client.

The truth? Solopreneurs need both.

From Book Concept to Newsletter

When I first dreamed up Dear Solopreneur, it was a simple idea: a book of 99 letters, each written as if to a friend, tackling the real moments entrepreneurs face. Some letters are gentle, some are fiery, all are honest.

But as the idea grew, I realised something important. The need could only ever be partly addressed by 99 letters. This is a movement that can’t be constrained in a book. It needs to be flexible, adaptable, and responsive to the questions the community asks of me.

That’s why I’m starting here — with the Dear Solopreneur newsletter. Launching mid-October, it’s the living, breathing version of the book: every week, a new letter, fresh from me to you, shaped by the realities of running a business today.

The book will come, but the newsletter is where it starts. And you can be part of it from day one.

Why It Matters

I created Dear Solopreneur because no one should have to walk this road alone. The highs are higher when shared, and the lows feel less crushing when you know someone has your back.

This isn’t about handing you yet another checklist or productivity hack. It’s about sitting down together and saying, “Yes, it’s tough. Yes, you can do this. And yes, here’s how.”

Through the letters and the community around them, my mission is to bridge the gap — to give you the insight of a business book with the heart of a self-help title, so you feel both equipped and encouraged to keep going.

A Cornerstone for Coaching

The proposition behind Dear Solopreneur — blending business strategy with emotional support — has become the heartbeat of my coaching practice. Whether I’m helping someone map out their systems, rediscover their confidence, or simply remember why they started in the first place, the DNA of Dear Solopreneur is there.

And it doesn’t stop with me. My goal is to equip the wider business community with the same tools, encouragement, and perspective — to make sure solopreneurs everywhere know that they don’t have to do it alone.

What You Need to Know

If you take just one thing from this, let it be this:

You don’t need to have all the answers. You don’t need to be bulletproof. You just need to know that you’re not alone.

That’s why I created Dear Solopreneur.

Your friend, coach, and business buddy,
Simon

P.S. The Dear Solopreneur newsletter launches mid-October. Subscribe now to be the first to receive weekly letters and lock in exclusive “first class” bonuses.