Top 40 Reasons To Start A One-Person Business Over Age 40

A list of reasons why you should consider starting a one-person business in your 40s.

The other day I was thinking….

What would I tell someone if they asked me why they should start a one-person business?

Especially when there are an endless amount of opportunities in the world.

You could go back to school, look for your dream job, buy into a franchise, marry a rich sugar momma (if you are single or newly divorced of course), etc.

Why a one-person business?

And what if this person was in their 40s, 50s, or 60s?

Isn’t the Solopreneur path a bit risky? Wouldn’t it suck to have to start ALLLL over again?

Well, I dug in, started racking my brain, and consulted with some experts, past and present (via books, blogs, and podcasts).

I found way more reasons than I expected, and today I will share them with you.

I list 40 reasons why you should start a one-person business in your 40s, 50s, and beyond.

But first, I need to give credit where credit is due…

One-Person Business Mentors

I didn’t invent the concept of the one-person business. And, even though I’ve experienced many of the following reasons first-hand over the past ten years, I didn’t invent them either.

I was introduced to the idea in the mid-2000s when I started considering a career change.

Here is a list of people who have convinced me, and continue to reinforce the idea, that being a Solopreneur and running a one-person business is a viable, lucrative, and future-proof option;

Tim Ferris - His book The “4-hour Work Week” showed everyone what was possible. It should be on every aspiring entrepreneur's must-read list. He is likely the one person who’s influence many future solopreneurs.

Perry Marshall - Not a one-person business expert per se’, but someone who has led by example. I and thousands of others started following him when he was THE go-to Google AdWords expert. But his name (personal brand). represents so much more these days. He’s is one of the world's most expensive business strategists and now is a recognized name in science. Plus, he is a shining example of career change (e.i. second acts), having gone from engineer to self-employed businessman (all while having young kids and bills to pay btw).

Paul Jarvis - Read his book “Company of One,” He might be the first person who started openly discussing this idea of a one-person business.

James Altucher - He has a bunch of great books, but his first one, “Choose Yourself,” really got my juices flowing. He also has a great podcast and is great at asking questions that nobody else asks in interviews.

Brian Clark - One of the OG’s of content marketing who founded CopyBlogger way back in the early days of social media. His current solopreneur-focused projects are Unemployable and the 7-Figures Small podcast. Refers to a One-person business as a “personal enterprise.”

Naval Ravikant - I’ve shared his quotes multiple times. His Joe Rogan interview is a classic and a great intro to his thinking. You can also check out the book “The Almanack of Naval Ravikant: A Guide to Wealth and Happiness.” it is one of those books I keep coming back to when I need a hit of wisdom.

Dan Koe - I just started following him early this year. He is sort of the next generation of Solopreneur (in his late 20’s I believe). Dan speaks to my artist-philosopher brain. As a singer-songwriter, I appreciate the emphasis on practicing the principles in the pursuit of authenticity and 100% originality. Reminds me of how an artist studies and performs covers to practice but ultimately aims to forge their own sound.

Justin Welsh - Another of the newer generation of Solopreneur teachers. Justin speaks to my engineering brain. As a former draftsman & guy in charge of standard product documentation, I admire his approach.

Those are just a few, and I could list dozens more but I had to cut it off somewhere.

To keep a running list of Solopreneurs and One-person business advocates, I’ve been compiling a Twitter list that you can check out here; Solopreneur Twitter List.

So, for those reasons…

39 Reasons To Start A One-Person Business

You could probably find similar lists on the web. But I made sure to include reasons that were more specific to us 40 - 60 years olds who have different wants, needs, and experiences.

Also, after hours of brainstorming and reading through content from some of the mentors mentioned above, I did use ChatGPT to help me fill out this list. That’s just me wanting to be thorough mixed with a bit of OCD.

Here’s your list, and buckle up cuz its a long one;

  1. Freedom and Autonomy: Enjoy the freedom to work on your own terms and make decisions independently.

  2. Flexibility: Set your own schedule and prioritize your work-life balance.

  3. Pursue Your Interests and Curiosity: Follow your true interests and curiosity to engage in work that aligns with your values.

  4. Capitalize on Experience: Leverage the wealth of experience gained over the years in your industry.

  5. Embrace Agility: Adapt quickly to market changes and capitalize on new opportunities.

  6. Focus on Your Best Skills: Prioritize the tasks and projects that align with your unique skills and expertise.

  7. Creative Expression: Embrace the opportunity to express your creativity and innovate in your chosen field.

  8. Maintain a Strong Personal Brand: Cultivate a personal brand that showcases your expertise and attracts clients.

  9. Control Over Direction: Have complete control over the direction and vision of your business.

  10. Job Security: Most people have this backward because they think a “job” is security. But it is only one income source and you are in less control of your fate. Create your job security by diversifying your income streams and building a resilient business.

  11. Fulfillment and Satisfaction: Experience a sense of fulfillment and satisfaction from pursuing work that truly matters to you.

  12. Intellectual Stimulation: Continuously learn and challenge yourself intellectually through entrepreneurial pursuits.

  13. Create Meaningful Impact: Make a difference by providing valuable products or services to your target audience.

  14. Work-Life Integration: Integrate work and personal life in a way that aligns with your priorities and values.

  15. Personal Growth: Experience personal growth and self-discovery as you navigate the challenges and successes of entrepreneurship.

  16. Fairer Pay: If you want a raise at a job, you need to ask. As a solopreneur, you have greater control over your income. If you want to make more money, you can learn a new skill, start a higher-value project, or at the very least, negotiate a higher fee if you’re doing client work. It is in your control.

  17. Financial Independence: Build financial independence and generate income based on your own efforts and abilities.

  18. Work at Your Own Pace: Set a pace that suits your energy levels and preferences, avoiding burnout.

  19. Legacy Building: Create a lasting legacy through the impact and influence of your business.

  20. Experience and Expertise: By this age, you've likely developed substantial expertise in your field, which can serve as a solid foundation for your business.

  21. Established Network: You've likely built a strong network of contacts over the years, which can be beneficial for customer acquisition, partnerships, and mentorship.

  22. Financial Stability: You may be in a more secure financial position, enabling you to take calculated risks in starting a business.

  23. Greater Confidence: Years of experience can bring greater confidence in decision-making and problem-solving.

  24. Reinvention and Renewal: Embrace the opportunity to reinvent yourself and find renewed purpose in your later career years.

  25. Work-Life Balance: Solopreneurship allows for flexibility, which can help maintain a healthier work-life balance, especially important as one grows older.

  26. Self-reliance: Being your own boss reduces reliance on others for income, fostering a sense of independence and self-reliance.

  27. Niche Markets: With your deep understanding of your field, you're well-positioned to serve niche markets that younger or less-experienced entrepreneurs may overlook.

  28. Adaptability: Life experience often equips individuals with the ability to adapt to changes and obstacles more easily.

  29. Mentorship Opportunities: You can use your knowledge and experience to mentor younger entrepreneurs, contributing to the entrepreneurial ecosystem.

  30. Personal Fulfillment: Starting a business can provide a sense of accomplishment and fulfillment as you're building something of your own.

  31. Reducing Employment Discrimination: Starting your own business can bypass potential age discrimination in hiring, providing a viable career alternative.

  32. No More Resumes or Interviews: In a one-person business, you often do the work in public, even if it is a small niche. Your work is proof you know what you are doing. No more typing up a resume that ends up in a pile of 50 others.

  33. Leveraging Technology: With the growth of technology, starting and running a business has never been easier, regardless of age.

  34. Building Personal Brand: As a solopreneur, you can build a personal brand, something that might come naturally with years of experience and expertise.

  35. Lifelong Learning: Running a business encourages continuous learning and personal growth.

  36. Flexibility to Travel: As a solopreneur, you can often work from anywhere, which could allow for more travel and new experiences.

  37. Resilience: Years of experience can increase resilience, an invaluable quality in entrepreneurship.

  38. Your future self will thank you: most of the people I’ve helped transition from employment to self-employment say the same thing after they took the leap: I wish I would’ve started sooner.

  39. Second Career: Solopreneurship can be a fulfilling second career… err… Second Act 😉 for those looking for a change or a new challenge.


40. It’s More Future-Proof

I’ve discussed this in previous posts, AI and robots are going to wipe out a lot of jobs. But it is also going to create a ton of opportunity.

Having the flexibility of having a one-person business gives you a huge advantage over 9-5 employees. You can dedicate parts of your days to learning new things and stay ahead of the game.

Meanwhile, the 9-5er will be busy working in a job that might be on the brink of elimination.

A one-person business gives you the flexibility a job likely will not.

…what’s difficult to automate is exactly what makes a company of one great: the ability to creatively solve problems in new and unique ways without throwing “more” at the problem. Whereas workers in “doing” roles can be replaced by robots or even by other workers, the role of creatively solving difficult problems is more dependent on an irreplaceable individual. Regardless of the rise of the so-called robot overlords, this is where the strength of a company of one lies.

Paul Jarvis

And we are seeing a lot of people are starting to realize this.

Check out this Google Trends chart.

Since I became a full-time solopreneur in July 2013, searches for “one-person business” have steadily increased. And solopreneur as a topic (red line) is also starting to get some traction.

Just as the tools and resources are improving and making it easier for employers to replace employees, they’re at the same getting better and more accessible for solopreneurs to replace less lucrative, more time-consuming tasks.

Which part of that equation would you rather be on?

Next Steps

So there you go.

In a nutshell, when you have a one-person business, you have a business that is unique to you; you call the shots and are much more in control.

And when you’re in your 40s, 50s, and beyond and have been in the workforce for years, you have everything you need to get started. In fact, you have a head start.

You can leverage current skills, interests, and experiences to start a one-person business while at the same time learning new skills, pursuing new interests, and gaining new experiences to grow that or any other business.

So, when you are ready to rock, start mapping out your skills as I did here.

And, if you want some help figuring out your next move, I am offering a free Kickstart Consultation to the first five people who take advantage of my Annual subscription.

In a few days from right now, you’ll have a clearer vision of what your second act will look like.

Ride The Lightning

I always try connecting the music to the theme of the article.

But it doesn’t always work out, and I end up spending WAY too much time trying to connect the dots.

So today’s tune doesn’t totally match, but it’s a damn good song.

Check it out…

I think I’ve listened to that tune 100 times in the last couple of months. Love it!

So, that should do it.

Remember to check out my offer. If you’re ready, I would love to work with you.

Have a good one,


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