Employment vs entrepreneurship

jasonleow • 12 Feb 2025 •
The promise of employment is the stability and security of a monthly paycheck. The promise of entrepreneurship is freedom to do whatever tf you want.
But it’s funny how over a long enough timeline, all those promises break down.
Be employed long enough and more likely you’ll experience getting retrenched. Solopreneur long enough and the freedom fades (due to hiring, getting bigger, more demanding customers etc).
Is there a sweet spot somewhere between a long-term job and calm entrepreneurship?
I believe there is, yes, in both.
Rare, but possible.
Employed but remote, pays well in a strong currency (USD), digital nomading in a low cost location, having side gigs to for diversify – perfect.
Running 2-3 profitable SaaS or products, solo but mostly automated, no heavy customer support, $10-20k per month – awesome.
Very non-traditional paths.
Long term risks remain.
But mitigated or prepared for.
The folly is to expect long term promises, in both employment AND entrepreneurship.
The best we can do is to evolve and iterate on said promises.
Comments
@haideralmosawi Yeah agree. If I ever hire it would be for tasks I absolutely hate. Avoiding pain is a great reason haha

I recently listened to Brandon Sanderson’s interview with Tim Ferriss. I absolutely love that:
1- Sanderson is insanely prolific
2- He keeps a schedule he enjoys (which includes ample time with his family)
3- He has a team who takes care of the work he doesn’t want to handle (consisting of family members and friends, which probably made the hiring a lot easier)
I’m reluctant to hire people now because I don’t want the headache and sense of responsibility, but I would definitely want to have lots of money I can spend to hire the right support that won’t feel like an added stress (if I’m pinching pennies AND I hire someone that will feel like a mental burden, not liberation).