A long time ago, in a cubicle not that far, far away… we all harbored secret work fantasies. F.I.R.E. (Financial Independence, Retire Early) is one of these fantasies: the daydream of having enough money to retire early. But another work fantasy for me took the top escapism spot throughout my entire 30 year career. A concept I called “Plan B.”
In my younger years, sitting with work friends around the lunch table, we would inevitably talk about a “Plan B”—the dream of running our own business and becoming entrepreneurs. Jobs in tech in the early 2000s were often shaky, which made the idea of having our own company a potential way to escape the insecurity. Or at other times thoughts of Plan B was a way to escape boredom.
We would sit around at times brainstorming businesses we could start. Most times it was just for fun and it died out quickly. I remember one time we focussed on identifying a waste stream that we could potentially turn into a new product. The waste would be free and make an input to our new product. Recycling at it’s best.
In the end any waste product we thought of someone else had already discovered a new use for:
- Grocery store Food waste – being turned into commercial compost.
- Cherry Pits – microwavable heating bag.
- Chicken feathers – pressed into a type of sound deadening insulation in auto door panels.
The list was endless. Yes we were bored manufacturing engineers with time to do research.
Even on my own, I explored two Plan B’s in depth. One of them was a consulting company I started. It turned into the most financially rewarding year I ever had. Funny enough that Plan B wasn’t a well-thought-out strategy at all. It was purely opportunistic—a classic right-place-right-time scenario with a limited shelf life.
My 2nd Plan B I was more serious about. I researched for almost two years until I realized the risk of capital was beyond my capacity. I never launched it. But I really enjoyed the mental gymnastics of the research and the “What If”.
The beauty of these early Plan Bs was that they were fun to think about. They filled the space with positives when the actual job was bogged down by negatives. The Plan B fantasy was always worth indulging in.
The New Plan B: Purpose Over Profit
Perhaps, as I approach retirement, I should dust off this “Plan B muscle” and start exercising it again. But the intention has completely changed. It’s no longer about starting a business from scratch. It’s about finding a topic to research as a hobby. To enjoy the “What if” process.
It could be starting a social network for age 50+ early retirees. It could be discovering what charity I truly care about or creating my own.
The new intent of Plan B is not to trade a 40-hour-a-week high-paying job for a 40-hour-a-week no-paying job that I don’t like. It’s no longer primarily about making money. Crucially, however, it is still definitely about not losing money!
When I have fun at work, it’s talking and working with people I genuinely want to be with. The work goal is almost secondary to the collaboration. The goal just gives us a commonality to work together on.
In the past, Plan B was a shared fantasy of riches. Now, at this age, it needs to focus entirely on the people aspect. It’s no longer about the big goal or the final outcome; it’s about time well spent with friends and people I choose to be with. The goal simply provides the common thread, just like work does.
It would be a Master Mind with a common purpose of bringing the people I like together or with new people with similar interests. The Master Min would give us a common goal to strive for. With the side benefit of hanging out with great people.
Redefining Pursuit
One true goal in retirement is to spend as much time as you can with people you like. It can also be a way to spend time without feeling like you’re wasting it. While drinking beer or golfing is fun, a purpose-driven Plan B offers more. Why not start or join a:
- Early Retiree Dog walking service
- Tree planting for community spaces
- Food Drives
- Death Star painters
- Etc..
A friend has always thought about brewing beer or whiskey in retirement. Opening a craft brewery has been a popular fantasy over the last two decade. But when I think through it, I realize the fun part is drinking the beer—not sourcing materials, buying capital equipment, perfecting recipes through trial and error, canning the beer, and chasing sales. The appealing part is the social side—the community you’d build and the people you’d meet.
A craft brewery is a nice fantasy and a great way to spend time with like-minded friends, but as a commercial venture it fails the “don’t lose money” test. If the beer is brewed just for a small group of friends to enjoy, with no intention to sell, then Plan B works perfectly. If the intention is to sell to the masses, the financial risk is likely too high to qualify as a fun, low-pressure Plan B.
My main takeaway here is Plan B could be used to start a new retirement project. To do some good in the world, to hang out with good friends, or to even meet new interesting people.
A perfect example is the story captured in Freedom For Fido – A Story Of Finding Purpose In Retirement – The Retirement Manifesto. Fritz Gilbert’s wife’s runs a charity named Freedom for Fido. They get together to build chain link fences so dogs no longer have to be chained outside. The dogs go from a short, heavy chain to a yard to run around in. Fritz and his wife help dogs and get to meet a bunch of good people. It checks all the boxes for a great retirement project.

So start thinking of your Plan B. It really could be what you need to retire to. It will allow you to meet like minded people and to make new friends. Which is one my goals in retirement.
If you ever had your own Plan B fantasy let me know what it is in the comments









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