The Fail-Safe Solopreneur Revisited – How I’d Tweak this Solopreneur Survival Guide 4 Years Later

Almost four years ago (April 11, 2021), I published a book about managing your well-being as a solopreneur. It was a deeply personal account about my struggles working independently for 10 years. Now, I’m almost at the 15 year mark!

The pandemic, higher costs of living, and new technology has only accelerated the movement toward solo and freelance work, along with social isolation. Freelancers now make up 38% of the American workforce.¹

I wrote the book to help this new wave of solopreneurs, creators and freelancers, to let them know their business and emotional struggles are normal, despite what they might read or hear online. 

If you know a friend or community who could benefit from the book, please share it with them! And if you have any suggestions for who I could contact to reach more solo business owners with this message, please let me know.

What would I change? 

Not much. I still believe the 6 practices are essential. They remind me of what I can do when I feel unsure, stuck or small.

Nevertheless, after 4 more years on this path, I would have emphasized three messages:

The Priceless, Non-Monetary Benefits of Controlling Where and How You Work

I would have told more stories highlighting the priceless, non-monetary benefits of solopreneurship. Like how I was able to take a trip of lifetime to Cuba and study AfroCuban folklore for one month interrupted. Or be with my father the last 4 months of his life.

What we desire most as solopreneurs is work flexibility paired with a steady income. While we often have to sacrifice some of one for more of the other, we work towards this goal not only for ourselves, but to support our loved ones. When I wrote The Fail-Safe Solopreneur, I didn’t totally realize how much simply being available for others could mean. After my Dad passed, I was able to be with my Mom for 6 months, and we traveled together to Croatia and Hong Kong to distract ourselves and heal.

Protect Your Imagination

For Chapter 2: Stuck? Seek Outsight, I would have proposed more exercises to unleash readers’ imaginations. I wrote:

“Through play, I’ve discovered a wealth of potential, personality, and resourcefulness. We just need to use our atrophied muscle of imagination. Play helps us discover our total, full-set of capabilities. And it’s a hell of a lot more fun than working hard.” 

In fact, my theme this year is “the imagination game.”  

I’ve struggled the past year to evolve my career. I know I want to do something different but have crawled at a snail’s pace. It’s all so damn serious, so heavy, so slow.

What has helped me most is attending events and taking a light, playful approach to career experiments:

• Joining a local co-working space and attending a day-long Entrepreneur’s Organization event. This gave me a burst of energy to do a sales push for my business, Touch MBA. 
• Writing an essay about my Croatia trip for Princeton Alumni Weekly. This gave me a taste of being a freelance writer. I realized how much I missed writing, and reading great fiction.
• Acting as if I had accomplished my goals. If I was HIM, how would I dress? Who would I spend time with? What would my home office look like? What type of problems would I be working on? It’s fun to let my imagination run free, and incredibly, more helpful and clarifying to prepare for a role (rather than working hard, doing more of what I’ve always done, and getting the same results). 

The Three Vital Components of Social Connection

For Chapter 6: Who Are You Grooming?, I would have used the US Surgeon General’s recent 3-pronged definition of social connection: structure, function and quality.³ I hinted at this with my diagram about “investing in friends,” but I think this framework makes the dynamic nature of connection more clear.

• Structure: the number and variety of relationships and frequency of interactions (examples: household size, friend circle size, marital/partnership status)
• Function: the degree to which relationships serve various needs (examples: emotional support, mentorship, support in a crisis)
• Quality: the positive and negative aspects of relationships and interactions (examples: relationship satisfaction, relationship strain, social inclusion/exclusion)

So, I would keep my spreadsheet listing an inner circle (3-5 people), superfamily (15 people), clan (50 people) and tribe (150 people) and associated contact rhythm, but also include a column to keep notes for relationship satisfaction.

I’ve realized it’s okay – and natural – to let people fall or even drop off your list, as the seasons of life change. Maybe we’re at different stages or places, or people just don’t have time anymore. And my interests and affiliations change as I do. 

I’ve found that the most effective step to combat social isolation is to proactively water your inner circle and superfamily – your two closest circles. As Kevin Kelly says in his Excellent Advice for Living, “Cultivate 12 people who love you, because they are worth more than 12 million people who like you.”

Over the past year, I’ve lost my father and three uncles. I’ve watched my mom, who is comfortably retired and financially secure, struggle with depression and social isolation. It’s very clear to me how essential relationships are to one’s quality of life. All the money in the world can’t solve this very human need. Social isolation can be as harmful to our health as smoking up to 15 cigarettes a day!³ So while working independently elevates our need for social connection, we should all monitor this part of life.

Finally, I would have put much more thought into the marketing and packaging of the book. But, that deserves a separate post. Let’s see if I can sell more books first!

We Can Learn from Our Past Selves

I remember having the strangest sensation the day I saw The Fail-Safe Solopreneur on Amazon. I remember feeling that I was no longer the person who wrote the book, that I had already graduated from that chapter of my life. And here I was about to announce it to the world! 

Now, four years later, I admire the courage and wisdom of my earlier self, and think wow, that guy had some useful stuff to say. The words, stories and packaging could be polished but overall, I still find myself emotionally connected to and reliving the lessons of The Fail-Safe Solopreneur.

I hope the book helps others survive the emotional rollercoaster of working alone so they can live out their dreams while giving their best to family, friends, and the world.

Footnotes

¹ Upwork Freelance Forward Research Report 2023

² Intuit QuickBooks Small Business Index Annual Report 2023

³ Our Epidemic of Loneliness & Isolation 2023: The U.S. Surgeon General’s Advisory on the Healing Effects of Social Connection and Community

My summary of the studies above, which came after I published my book in 2021:

• Remote and freelance work are now normal
  • 52% of all Gen Z professionals and 44% of all Millennial professionals performed freelance work; freelancers now make up 38% of the American workforce¹

• Technology, including AI, makes it easier for solopreneurs to build their businesses
  • 1 in 2 solopreneurs say digital technology made starting a business possible²
  • 20% of freelancers use AI compared to 9% of non-freelance professionals²
  • Yet, solopreneurs report higher stress and lower satisfaction than business owners with employees²
• Americans are spending more time alone than ever
  • Almost half of Americans (49%) in 2021 reported having three or fewer close friends—only about a quarter (27%) reported the same in 1990³
  • Loneliness and social isolation increase the risk for premature death by 26% and 29% respectively – and both are on the rise in the US³
  • Lacking social connection is as dangerous as smoking up to 15 cigarettes a day³