Working Solo, for a new generation

In the world of solopreneurship, let’s focus on what's still important after 30 years.

Some memories are time transporters. You close your eyes and zap — you’re right back in that moment.

The summer of 1993 hummed with those moments of making. I recall the 2 a.m. writing marathons, Labrador at my feet (Cooper Black, named after the typeface that mimicked his pudgy profile). The hot, sticky Hudson Valley nights in my 100-square-foot porch office, with the nocturnal calls of frog peepers in the yard and coyotes in the distance.

I was pushing to make a deadline for my first book, Working Solo, so it could be on press for the mid-October publication date. I completed the final edits as I laid out the 400 pages using PageMaker software, making sure each page was visually inviting and had no gremlins like weird spacing or errant hyphenations.

I was driven by the unquestioning belief that my book could be the guide I had longed for when I started my solo business journey more than a decade earlier. I was also naive about the financial risk I was taking by self-publishing 30,000 copies. Yet I plowed on throughout those steamy summer nights.

Time for a 3rd edition, made in public

It’s now a summer 30 years on, and more late nights await me as I create the third edition of Working Solo. The first edition was created in a world of landlines, fax machines, and a new technology called the World Wide Web. A Seattle startup called Amazon was selling books online and expanding into music CDs. The cloud was still something for the evening weather report.

This new edition enters an environment of companies that didn’t exist in 1993 — Google, Facebook, Twitter, and so many more. It’s also fueled by the power of AI and the new kid on the technology block, Chat GPT. In a world of stronger social connections than decades ago, there’s new meaning to my original mantra: Working solo is not working alone.

These connections also extend to the “build in public” philosophy. Makers gain inspiration, feedback, and encouragement from a global community of interested supporters. It’s an approach I look forward to exploring, particularly since it contrasts so starkly with my earlier writer-in-a-cave experiences.

A new adventure

I embark upon this newsletter journey with you in tandem with the new edition. My aim is to share a bit of what’s changed – but with a greater focus on the principles that remain at the heart of solopreneurship. So many questions persist. 

• How do you build a meaningful, profitable solo venture in the 21st century? 

• Who are the key players in a solopreneur’s life? 

• Which ideas are worth pursuing when you have so many?

• When do you hold onto an idea and when do you quit? 

• What does it take to create sustainable solopreneurship that lasts decades? 

I’ll share my thoughts on these issues and many more in the weeks ahead.

Thirty years ago, I had little idea that Working Solo would turn into a global phenomenon and become the chosen lifestyle of so many. Similarly, I embark upon this adventure with you, not knowing what’s ahead but ready to explore a new version of Working Solo and a fresh version of solopreneurship.

As in those decades ago, we’re all making it up as we go along. However, there are many more of us these days, and we’re connected by email, Zoom, and online communities, by wires and satellites, and yes, even face-to-face meetups.

My goal is to streamline the journey for a new generation of solopreneurs so that you can go far beyond what I dreamed possible during those humid late nights of the summer of 1993. 

Thanks for coming along on this new adventure and spreading the word.