chapter neXt - Issue 3
Self-Employment For The Over 50 Set
In 2000, there were 3 million self employed people in the over 50 set. In 2025, there are about 7 million over 50 entrepreneurs. And self employment is growing the fastest in the over 65 set.
Self-employment means a lot of things - for instance, all Uber & Lyft drivers are self-employed, most insurance agents and many lawyers are self employed…it doesn’t mean that you have to be doing some cutting edge tech thing to be part of this wave of people who are taking the opportunity to either start a second career, make a little cash (because putting those munchkins through college is EXPENSIVE) or you realize that your retirement next egg isn’t quite generous enough, you don’t have to be a serial “entrepreneur” to be part of the wave of seniorpreneurs.
And being an older entrepreneur doesn’t mean that you have to learn the Walter Huston old coot prospector dance either:
Self Employment Is Taking Charge of Your Financial Destiny
Your 401(k) goes up, and it goes down - any you have no control over that. But your own business - part time or full time can be amazing.
For instance, I’ve driven for Uber & Lyft to add some cash when we needed it. My wife started tutoring as a way to make extra money (and it turned into a vocation - need some executive function coaching for you, your kids, or grandkids - Julia is AWESOME.)
For some of us, starting a business after our first career has been a lifelong dream. I think that we’d be bereft of local florists, bed & breakfasts, art galleries and gift shops without those who took the leap into entrepreneurial living in their second act.
Much of the desire to start a business after 50 (or to become entrepreneurial) is often driven by a desire to do something that matters and is connected deeply to the work that perhaps your heart always wanted to do, but your career ambitions (and your mortgage payments) may have dictated otherwise.
But for many of us, the reason to become a seniorpreneur is FINANCIAL - being able to scale income without necessarily investing more hours, or perhaps wanting to build something that can be sold - entrepreneurship isn’t easy. But it is the best way to grow your earning power in the least amount of time. (Unlike some folks, we don’t have a family fortune to fall back on, nor do we have a long lost rich uncle that has mysteriously reappeared bearing a trust fund with our names on it.)
So if you are thinking about entrepreneurship as a financial vehicle, my advice is to go slow and test things out before you make a decision about your entrepreneurial direction. Here are my requirements for an entrepreneurial “test”:
Low To No Investment Needed: Even if you have substantive assets, doing something like renting a office or a commercial kitchen or whatever probably isn’t the best place to use your resources in the early stages.
Short Feedback Loop: You don’t want to invest too much time, energy, love or money into something before you know if it loves you too. For your testing phase make sure that you are thinking about feedback loops - how quickly can I know if this is a good idea or not.
Not Advertising Dependent: There are some kind of ventures that DEMAND that you spend money on advertising to see if they are going to work - ecommerce comes to mind - I’d avoid those.
No 1 Way Decisions: A 1 way decision is one that is hard to reverse. Committing to long contracts, large inventory buys, long-term leases and the like before you know your business is the right one for you is seriously risky - regardless of your assets.
Here are some ways to think about ways to test the waters before you decide what you are going to build.
Gig Work: Places like Uber, Lyft, DoorDash, UpWork, etc. aren’t going to make you rich, but they can provide steady cashflow and are incredibly flexible. This isn’t being an entrepreneur per se, it is being entrepreneurial - so you get to try on the idea of freedom and flexibility to adapt to it (harder than you think if you’ve spent 30 years commuting to an office…). This has a short feedback loop and is zero cost - but it is closer to a job than starting your own business. Good for testing out how you adapt to infinite flexibility & zero accountability, though.
Consulting: When you are an entrepreneur, you are hurtling into something that has no frameworks or guardrails. There are no existing processes or systems. It takes time to discover those on your own - so doing consulting in an industry that is familiar to you is a great first step - and you probably have some kind of network you can draw on - and this has a short feedback loop. Highly recommended as a starting point.
Volunteering (Commercial): This is weird, TBH, asking to volunteer in a business. Over the years, I have had people come to me (mostly younger) and ask if they could volunteer in my business so they can see if they want to work in that industry. I have rarely (if ever) said yes. However, more than one of my clients has taken on a senior (both in age and industry experience) volunteer who have been interested in starting a similar business to the one they volunteer for…they have been really successful engagements for both the volunteer and the business.
Volunteering (Charitable): Non-profits and community organizations are full of volunteers - and many of those volunteers are older. (That isn’t a reflection on the virtue of us GenXers - but we do kick ass.) Volunteering can be a great way to learn new skills - marketing, negotiating, management and more. Part of the joy of your neXt chapter is that it isn’t defined by all the chapters you’ve had before.
Want To Start Reading Up On Becoming An Entrepreneur?
All of these books are perfect for those of us who want to start - are afraid we don’t have the skills to start, but have too much GenX cynicism to believe in unicorns and defined benefit retirement plans.
The E-Myth: Michael Garber says if you are being a hoser and not paying attention, you’re building a job you’ll resent. That is unless you systematize the hell out of it. Gerber’s basically saying to make systems that allow for delegation & accountability - even if you are the only employee.
Company of One - Why Staying Small Is The Next Big Thing In Business: Paul Jarvis tells you it’s okay not to become the next unicorn founder hopped up on Red Bull and VC pixie dust. Build a chill, profitable business and skip the startup trauma cosplay. Who has time for that shit anyways?
Die With Zero: Bill Perkins hot take: hoarding money for a retirement you may not enjoy is dumb. This is the Gen X anthem of “we’re not here for a long time, we’re here for a good time” but with spreadsheets.
Essentialism: Greg McKeown’s basic vibe is this: You spent decades people-pleasing and chasing shiny objects. It’s time to Marie Kondo your to-do list and give a middle finger to anything that doesn’t move the needle or spark joy.
The War of Art: Stephen Pressfield says “Resistance is that voice in your head saying, “Maybe I’ll start Monday.” He dope slaps it out of you like your old man did when you threw that baseball through the school window. Do the work. No one’s coming to save you.
GenX News & Notes
Signing Off of WKRP: RIP to THE reason teenage boys watched WKRP in Cincinnati: Lonnie Anderson died earlier in the week at the age of 79. Dr. Johnny Fever may have been cooler - but Lonnie Anderson was reason enough to tune in. (And her subsequent tabloid divorce from Burt Reynolds confirmed what I always suspected - he was an a-hole.
I Want My MT-rivia: Everyone knows that “Video Killed the Radio Star” was the 1st video played on MTV. What was the second? Stumped? I was - find the answer on the other side of this link - and I promise that this song will be in your head all afternoon.
The “Forgotten” Generation Gets an Apology?: About f’ng time. Emily Stewart writes in Business Insider that FINALLY we might be getting our moment in the sun politically, culturally, etc. Whatever. I’m down for finally being culturally relevant if there are snacks, and the music isn’t so loud that you can’t have a conversation.
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chapter neXt is a newsletter/community/guide for entrepreneurial folks in their 50s and beyond. It is published by Julia Kelahan (check her out on LinkedIn, her amazing strength-based learning center & her ADHD & Executive Function coaching business) and Tim Kilroy (check him out on LinkedIn & his agency growth business & his agency-focused newsletter). They are the proud parents to 5 kids, they live near Boston & their dog’s name is Fred. Our ads are ads - duh. But some of the publishers that we link to in our content may offer us a commission if you buy something from them - that doesn’t influence what we link to, nor does it influence what we say about it.