9-5 to 5-9 to All The Time
A regular path through chapterneXt is this:
You work a 9-5 for someone else
You feel the shift & start a 5-9
5-9 turns into all the time
It’s a good shift, honestly. It makes sense. It’s practical.
But there is another shift that happens:
At a 9-5, you shape yourself to the needs of the job
At a 5-9, you shape yourself to the needs of the dream and the time available
Full on entrepreneurship must be shaped around YOU
Human nature is like water. It takes the shape of its container.
When you take the journey, you are constantly “re-identifying” yourself and “rearticulating” your terms of engagement. Post-50 entrepreneurship doesn’t look the same on everyone. Let’s walk through some structures:
Build A Business
You build a 9-5 & change from your 9-5 identity into the CEO of your new thing.
This could be a “big” business (you want to scale) or it could be a smaller thing (you are a fractional exec or consultant)
→ You are building something that has a familiar shape.
Buy A Business
You find a business that you like & buy it. You become the CEO of something you didn’t build.
You find a franchise and buy a license. You aren’t building the process or the product, but you are building a business.
→ You are building something on top of an already defined shape.
Some Other Thing
You want to write a book, or turn bowls, or paint and want to turn it into an income stream.
You focus on cash-flowing investments like AirBnB properties, high-yield dividend investing, or similar.
→ You are building a businesses that have less shape - the structure is yours to create.
Let’s Dig A Little Deeper (and start generating ideas…)
Build A Business
What you did in your old life, but you do it better. This is a very popular entrepreneurial path.
Consult to other businesses as a fractional exec. This is a place where experience is your advantage.
Build a better mouse trap - classic entrepreneurship.
Buy A Business
There are marketplaces like Acquire.com & Flippa to buy an existing business. This requires capital and time, but it's actually a pretty low-risk way to go.
There are franchises for everything from McDonald's to Pickleball. This is a very popular neXt chapter option. Check out the FTC’s guide to franchises.
Something Else
Write a book and sell it.
Create some art and sell it.
Create a course and sell it.
Tutor somebody.
Invest in real estate.
Start a B&B (just like Lorelai Gilmore)
Try your hand at stand-up comedy.
Support a small, independent film.
Become a travel guide and lead trips all over the world.
There’s an endless array of choices (seriously) for your chapterneXt. The most important thing to remember here is that this isn't about creating a VC-funded rocket ship or a company that's going to have 500 employees - unless that's what you want. All of the ideas ought to make you happy when you think about it. Because entrepreneurship is hard and it does require the investment of your soul in a completely different way than a job did. You are going to be taking the shape of your endeavors - make them worthy of you. (Read more Wallace Stevens - I bet you like it more now than when you had to read it in 11th grade.)
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You just read about the various neXt chapter possibilities, and now your brain is zapped up like you are rocking down Electric Avenue. You feel inspired and jazzed and ready to roll. Eye of the Tiger is suddenly your background track. But how do you actually decide which route to pursue? Are you a solopreneur? A business creator? An investor? A craftsperson? How to know? It’s like standing at a choose-your-own-adventure crossroad where every page looks tempting. So - which one to flip to?
Well, here is where you dig back to those lists you made to find your clues. Study them carefully, because they tell you about how you naturally operate. They weren’t just busywork - they are the clues to follow (you know I want to talk about Scooby and the Gang right now, but I am trying to avoid overkill - thank me later). If you have a list full of solitary pursuits, that is probably a good indicator that you want to be doing a solo thing, rather than trying to start a business that involves other people. Good with numbers and enjoy finance? Dig into creative ways to invest. Has art been a hobby for years? Now might be the time to figure out how to make it the gold egg of your Golden Years (whop whop whop).
Take advantage of all the strengths being a Gen Xer has given you. We all know the stereotype of “latchkey kids” - we know it because many of us did actually experience it. That means we know how to figure stuff out and make things happen. We’ve got battle tested street smarts. We know how to get scrappy - and scrappy is vital as an entrepreneur. We are creative, adaptable, and independent with a can-do work ethic. Use these abilities to let your imagination roam and really see yourself in the different options. Create your own little Fantasy Island scenario in your brain to see what it feels like on each path. When Tattoo and Mr. Roarke greet you after you get off “da plane”, what is the new adventure being built, and does it feel like an “oh yeah!” or an “oh, no”?
This is like a mixtape for your brain, just the good tracks that actually get you moving. Think less “woo-woo vision board” and more “here’s how your brain can get shit done” Bottom line: whether you’ve got ADHD, executive dysfunction, or just too much life, this kit helps you finally do the stuff that matters. Check it out.
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.