It’s more complicated than ever at the same time as being the same as it ever was.
Where your cash flow will come from now and, maybe more importantly, in relative old age and beyond. If you’re just joining us or missed it, go here to see what I mean when I refer to relative old age.
Same as it ever was because Generation Z and millennials sometimes act like they came up with the idea of a side hustle and, more broadly, being self-employed. (They do the same with food trucks!). My Dad had a side hustle—at times more than one—since before I was born. And I’m 48 years old. He’s coming up on 89 later this year.
The difference between my Dad’s version of a side hustle early in the adult iteration of his working life—(he started working at a very young age)—and today’s is that my Dad did it out of a mix of work ethic and what he, at least, perceived as necessity. It was only later on in life—once he paid off our house—that the side hustle was a way to keep busy and generate additional cash flow when he finally retired from his full-time job.
The other big difference is that my Dad didn’t conduct his side hustles on the computer or with the help of technology.
His three side hustles were:
Painting houses. This was a constant from when I was a child until he fully retired roughly 10-15 years ago. I’m convinced my Dad could have turned this side hustle into full-blown self-employment. However, he enjoyed the perceived security and benefits that came along with a traditional job. This approach served him well.
Part-time work in a liquor store owned by a family friend. He did this mostly when I was younger then, on and off, as needed. I think he liked the social aspect of the job and being out of the house a couple to a few nights a week.
Helping a local sports bookmaker. A bookie. Sounds crazy. But it’s really not. At a very young age, I even helped my Dad help the bookie! I’ll tell you the story one day.
At some points, he did all three side hustles at once in addition to his full-time day job!
How is this any different from anything anybody is doing now outside of the natural technological advances and shifting lifestyle preferences we expect to see in society?
The guy who owned the liquor store was—actually he is, because he still owns it!—self-employed. An independent small business owner.
More complicated than ever because, particularly from a cost of living standpoint, everything is more expensive now. And—related to this—because the idea of a traditional retirement for large swaths of pretty much every demographic younger than my Dad has become next to, if not impossible. So, for some baby boomers and much of Gen X, the millennial generation and Gen Z.
That’s what we tend to discuss a lot around here. Alternatives to traditional retirement because you have no choice or simply because you want to live life differently.
So—
If you’re going to live the semi-retired life …
If you’ll Never Retire out of choice or necessity …
If you choose to work less now so you can work less longer …
If you decide to live more evenly across the lifespan …
Where is the money going to come from?