Book: Solopreneur

“The Solopreneur Life” – A Compilation of Wisdom from Solo Business Owners

Date: October 26, 2023 Source: “The Solopreneur Life: 42 Solo-Business Owners” edited by Larry Keltto (2011)

Executive Summary:

This book compiles Q&A interviews with 42 solopreneurs from diverse backgrounds and industries. It offers a practical and insightful snapshot of the solopreneurial experience in the early 2010s. Key themes revolve around the motivations for starting a solo business, the best and worst decisions made, lifestyle changes required, strategies for competitiveness, current challenges, future aspirations, and advice for aspiring solopreneurs. The overall sentiment is overwhelmingly positive, with many expressing immense satisfaction with the freedom and control that solopreneurship provides.

Key Themes and Ideas:

1. Motivations for Starting a Solo Business:

• Desire for Independence and Control: Many solopreneurs were driven by a desire to “do things the way I wanted” (David Billings) and make their own decisions. Bob Andelman emphasized having “a stubborn independent streak.”
• Dissatisfaction with Corporate Culture: A significant number left traditional employment due to dissatisfaction with corporate culture, politics, and a lack of personal fulfillment. Andy Hayes stated, “I was depressed and had a lot of health issues because of it. I finally had had enough.”
• Need for Flexibility and Work-Life Balance: Several individuals sought a more flexible schedule and location independence. Laurie Gay wanted “a career that is location independent, meaning it permits me to live anywhere and still be earning a living.”
• Pursuit of Passion and Purpose: Some individuals, like Jim Sheard, started a business as an “avocation” and a way to occupy their time and mind after early retirement. Others wanted to escape from careers they hated.

1. Best Decisions Made When Starting a Business:

• Focusing on a Niche and Being Unique: Many emphasized the importance of specializing in a specific area and differentiating themselves from competitors. David Billings stated, “My only strategy is being completely unique. That way I don’t have to compete.” Patrick Curtis advised, “Become an expert in a very narrow niche and serve that niche better than anyone else.”
• Building a Network and Seeking Support: Solopreneurs highlighted the value of connecting with other entrepreneurs, joining forums, and seeking mentorship. Laura Petrolino emphasized that “it takes a village.” Tzaddi Gordon benefited greatly from an “informal mentorship” with a friend.
• Starting Slowly and Keeping Overhead Low: Several individuals advised starting small, avoiding debt, and maintaining low overhead. Cari Redondo “did not go into debt, and kept my overhead low.” Deb Howard Greenleaf took on “only a few new clients at a time” to develop systems.
• Embracing Flexibility and Adaptability: Barbara Milgram found that not having a “master plan” allowed her to remain flexible and adjust to changing market realities.
• Using social media: Amy Pryor said “I think the best thing so far has been getting involved in social media.”

1. Mistakes Made and Lessons Learned:

• Trying to Be Everything to Everyone: Several solopreneurs warned against trying to appeal to too broad an audience. David Billings said, “Trying to appeal to everyone…Things got really messy, scattered, and depressing.”
• Discounting Services and Not Requiring Deposits: Amy Harrison cautioned against “discounting too much and not taking a deposit,” as it devalues your work.
• Neglecting Customer Relationships: Burton Kelso learned the hard way that “you have to stay in constant contact with your customer base” to foster loyalty.
• Comparing Yourself to Others: Nichole Bazemore realized that “comparing myself to every copywriter in the world…is a recipe for disaster.”
• Over-Promising and Not Setting Clear Deadlines: Deb Howard Greenleaf said her “biggest mistakes have all involved over-promising.”
• Failing to Filter Potential Clients: Revka Stearns advised to “filter potential clients, not taking every project that comes my way.”
• Waiting Too Long to Launch Products: Kelly Kingman says she “waited a very long time before creating my first product.”
• Being too trusting: Laura Petrolino was “too trusting” and now has “stricter contracts and payment terms.”
• Growing too fast and going into debt: Tricia Lawrence said growing too fast and going into debt was the “worst decision hands down.”

1. Lifestyle Changes Required:

• Lowering Standard of Living: Some solopreneurs experienced a temporary decrease in income and had to adjust their lifestyle accordingly. David Billings had to “significantly lower our standard of living.”
• Sacrificing Time and Social Life: Many acknowledged that being your own boss is demanding and requires sacrifices in social life and personal time. Caroline Colóm Vásquez stated, “Being your own boss is the most difficult job you will ever have.”
• Prioritizing Health: Jim Sheard regretted not prioritizing exercise and healthy eating earlier.
• Health Insurance Struggles: Sherice Jacob pointed out that “Health insurance is a royal pain for solo business owners.”
• Spending time with positive people: Amy Harrison said you must look “for people who will support that and encourage you.”

1. Strategies for Staying Competitive:

• Being Unique and Authentic: Many emphasized the importance of differentiating themselves from the competition by being true to themselves. David Billings said his “only strategy is being completely unique.”
• Focusing on a Niche Market: Laurie Gay advised “growing really clear on who you are serving” and solving their specific problems.
• Providing Excellent Service and Building Relationships: Dawn Svenson Holland focused on “deliver[ing] service that reflects the deep and abiding respect” she has for her clients. Amy Harrison looked for “a long-term relationship with my clients.”
• Continuous Learning and Professional Development: Solopreneurs stressed the need to stay updated on industry trends and acquire new skills. Shayna Walker pursued “as many educational opportunities” as possible.
• Embracing Social Media: Burton Kelso embraced social media to keep in contact with his customer base.
• Never settling: Tricia Lawrence said to “never settle.”

1. Biggest Current Challenges:

• Balancing Client Work with Business Development: Barbara Milgram found it challenging to “fill the pipeline for new business while juggling the demands of current projects.”
• Managing Overwhelm: Kelly Kingman struggled with “managing overwhelm” and prioritized self-care.
• Finding the Right Business Model and Scaling: Matt Mansfield focused on “building a scalable mentoring practice.”
• Feast or famine: Deb Howard Greenleaf was “still trying to find the sweet spot where I’m hitting my monthly profit goals but not working extra hours after the kids are in bed.”
• Being oversaturated by competition: Burton Kelso said the “business market is oversaturated with Solo-Geeks and Mass Market Geeks who are all making the same promises.”
• Finding time for projects that grow your business: Sherice Jacob wanted to set “aside a couple of hours a day just for my own projects.”
• Dealing with people who have had bad experiences with competitors: Tommy Walker says his biggest challenge is “dealing with people’s hurt from working with snake-oil companies that took their money and ran.”

1. Five-Year Aspirations:

• Growing and Expanding the Business: Many wanted to expand their offerings, increase their client base, and hire employees.
• Creating a Sustainable and Scalable Business: Melissa Dinwiddie wanted “a true business that I can leave for a month or two at a time, knowing it will run just fine without me.” Sherice Jacob wished to have “much of the routine work is more automated or managed without my direct intervention or supervision.”
• Achieving Financial Goals: Dawn Svenson Holland aimed at “exceeding the income of the position I left for this new venture.”
• Making a Difference and Leaving a Legacy: Jim Sheard wanted to be “well-known and appreciated for the things I have written and the products I have developed.” Angelique Rewers envisioned her “business being a true change agent in the small-business world.”
• Achieving a healthy work/life balance: Tricia Lawrence wanted “to not worry about where the money will come from next month so that I can focus on how I feel and what I want to do each morning.”

1. Fallback Plans (or Lack Thereof):

• Many rejected the concept of a “fallback plan,” viewing it as a lack of commitment and focus. Amy Harrison stated, “I don’t have one because I can’t really focus on making this work if there’s an alternative in the back of my head.” Shannon Reece is on a “no option to fail” mission.
• Others had alternative skills and experience they could fall back on, such as previous careers, education, or consulting work. Patrick Curtis “could always go back into finance.”
• Some would just start another business: Helen Robinett’s fallback plan is to “Start another business!”
• Adapting and Evolving: Tzaddi Gordon’s only failure was failing “to evolve the business.”

1. Advice for Aspiring Solopreneurs:

• Just Start: Angelique Rewers advised, “Do it. And do it now, not later. It doesn’t get easier if you wait.” Melissa Dinwiddie said to “Start. Just start. Take one step toward your goal, now.”
• Believe in Yourself: Bob Andelman said to “Believe in yourself and pursue your dreams.”
• Don’t listen to other peoples advice: Koldo Barroso said to “Don’t listen to other people’s advice too much, not even mine.”
• Know Your Strengths: Shannon Reece: “Really make sure that you are pursuing a business option that taps into your greatest strengths, and is not an area where you will be daily working to overcome your weaknesses.”
• Be Prepared to Fail: Bill Dwight: “Be determined to succeed, but be prepared to fail.” Koldo Barroso said to “To me, success means learning to fail. So if I fail again, I will always be me and pull myself together and keep going on.”
• Do Your Homework: Deb Howard Greenleaf: “Do your homework! Understand what client problem you’re trying to solve. What’s their pain?”
• Don’t Get Overwhelmed: Natalia Sylvester: “Don’t let yourself get overwhelmed by the big picture. Focus on the small steps, put everything you’ve got into them, and they’ll turn into something bigger before you know it.”
• Love It, Learn It: Jill Chivers: “Love it, learn it. You must be passionate about your area because you’ll need that fire to keep you going during the tougher times.”
• Test Your Ideas: Kelly Kingman: “Start testing your ideas right now.”
• Don’t Quit: Tommy Walker: “Don’t ever quit!”
• Love the fact that success and failure rest squarely on your own shoulders: Barbara Milgram: “To learn to love the fact that both success and failure rests squarely on your own shoulders.”
• Read, Network, Try and Fail: Shayna Walker: “Read, network, try and fail; it amounts to seeking as much education in your field and in business as you can, developing more connections than you could possibly ever conceive of needing, being open to new experiences and banishing a fear of failure.”
• Build a network to act as a board room: Helen Robinett said to “Build a network that will become your board room to thrash out the issues that you need serious assistance with.”
• Become an expert in a narrow niche and serve that niche better than anyone else: Patrick Curtis: “Become an expert in a very narrow niche and serve that niche better than anyone else.”
• Give yourself permission to succeed: Linda Lopeke says to “Before you do anything else, give yourself permission to succeed.”
• Practice persistence and build resilience: Linda Lopeke says to “Practice persistence; build resilience.”
• There will be conflicting advice but its about what works for you: Andy Hayes: “If you spend enough time, you’ll soon realise that most gurus have conflicting advice. But most of these people are successful, so if they say it worked, it worked for them. The real magic is figuring out what will work for YOU.”

1. If Starting Over, What Would They Do Differently?

• Network Sooner: Several solopreneurs said that if they were starting over, they would network much sooner. Sherice Jacob “would have probably started networking with people a lot sooner.”
• Not Worry About Fitting In: David Billings: “I wouldn’t have worried so much about trying to fit in. I would have rocked the boat more, earlier on.”
• Trust Things Will be OK: Amy Harrison: “I’d have told myself not to worry so much and to trust that by working hard for my clients and working hard to build relationships, things would be O.K. and evolve at their own happy pace.”
• Focus on a Small Niche: Ted Prodromu: “I would focus on a small niche, work on PR to get my name/expertise out there and build recurring revenue into my business model.”
• Have more systems in place more quickly: Helen Robinett: “Have more systems in place more quickly.”

1. Are You Glad You Became a Solopreneur?

• Overwhelmingly Yes! The resounding answer to this question was a resounding “YES!” Solopreneurs expressed immense satisfaction with the freedom, control, and personal fulfillment that comes with being their own boss. They appreciate the ability to set their own hours, choose their clients, and pursue their passions. Many feel empowered and in control of their own destiny. Bill Dwight called it “ecstatic.” David Billings said, “It’s the best thing I ever did in my career. It’s also the hardest thing I’ve ever done.” Natalia Sylvester said, “Becoming a solopreneur was one of the best decisions I ever made because it made me realize that I’m in charge of my life.”
• Jill Salzman said explaining the joys of solopreneurship are akin to trying to explain why one likes chocolate: “Because.”

Conclusion:

“The Solopreneur Life” offers a valuable glimpse into the rewards and challenges of solo business ownership. While the specific circumstances and industries vary, common themes emerge around the desire for independence, the importance of building a network, the need for adaptability, and the overall satisfaction derived from pursuing one’s own path. The book serves as an encouraging and practical guide for anyone considering the solopreneurial journey.

RYT Podcast is a passion product of Tyler Smith, an EOS® Implementer (more at IssueSolving.com). All Podcasts are derivative works created by AI from publicly available sources. Copyright 2025 All Rights Reserved.