It’s hard to articulate how much reality shifts when you move from full-time work to self-employed work.
It still sort of amazes me how different almost every aspect of my life is compared to five years ago. Routines, work, time, money, relationships, desires, travel…
A big driver of people not “going back” probably has to do with the fact that the degree of difficulty of going from long-term self-employed to full-time work is a lot harder than the opposite shift. A lot is simply allocating more time to other people for more predictable cash.
When I had a job almost all moments of life were some sort of preparing for work, being at work, recovering from work, planning breaks from work and so on.
Now I wake up and sort of decide what’s most interesting most days.
For me, this is a dramatic life upgrade. Your mileage may vary.
Full-time work indirectly solves a lot of other problems
Full-time work indirectly solves a lot of other problems and one of the challenges of leaving is you don’t know they’re being solved. Identity, money fear, existential fear, status needs, desires, feeling loved and respected.
Step outside of this and you need a plan for those.
So in this new reality I spend a lot more time thinking about how to solve those “problems” directly and/or how to experiment with setting up my life in different ways to deal with them. For me this is sort of fun and is worth the cost of admission.
I’ve made new friends on similar life paths
One weird thing about this new path is that at the same time I’ve made new friends on similar life paths it’s coincided with the time in life in which you drift away from friends due to life circumstances.
I sort of created that distance by moving abroad and embracing solitude.
Of people that read and responded to my book the ratio has been 99/1 of people in my life after I left my job to friends and family before I left my job.
This is the opportunity of the internet - you can serve a niche outside your village - so not complaining. It’s just weird.
One thing that makes me excited about staying on this path is that I’ve made so many good friends trying or doing similar things and we all sort of have a similar reality.
I don’t have desire to escape work anymore
Another big difference is that I have almost zero desire for short-term trips, vacations, weekend getaways, or fancy stuff like that.
I sense it’s because I don’t have desire to escape work anymore. Also just don’t get as much joy out of “partying,” drinking, etc.
As I’m optimizing for life I want to live, I mostly want to be where I am with the people I’m already surrounded by.
Vacations are fine. I’d definitely go with other people. But if it’s up to me I’d rather live somewhere new for 1-3 months.
Fears are just part of the journey
When I talk to people who have different fears and insecurities than me it’s often a painful conversation if they want to talk about those insecurities. It’s very hard to convey to them that I don’t experience those things the same way they do.
When you’re on an uncertain path I find that fears are brought to the surface of awareness but also are sort of sprinkled more uniformly throughout day-to-day and month-to-month life. They are just part of the journey rather than things you seek to muffle or numb.
I ramp up and down with ambition
An interesting thing about the work side is that ambition shifts from something constrained by job moves and employers to something you decide on a spectrum all the time.
Some people love pushing it to the max all the time (burnout is common too) while others ramp up and down.
I sort of ramp up and down with ambition but I anchor to trying to build things that I like doing and might make money independent of time.
I also have the “free option” of ramping up ambition at any time. My general approach is to ramp up and down throughout the year.
Time wealth is real and amazing.
Given my mediocre ambition, it also means I’ve disconnected from my former peers and friends in terms of life accomplishments. This coupled with the crazy housing market means that I’m not going to be owning a home unless I get lucky with my work, scale ambition, or get a job.
This is totally fine. A home has too much busywork and cost, and I’ve sort of mentally committed to not thinking about it for five years, which is freeing. This really stresses a lot of my full-timer friends though because it’s such a central milestone.
People don’t want to quit their jobs
I wish more people could experience this alternative reality. This is sort of what I tried to let people sample in my book and writing in general.
But I also am hesitant to recommend a full leap. I wish more people took sabbaticals or “freelance years” though.
People don’t want to quit their jobs, they want a safe way to see if other realities are possible.
Full-time jobs and the default path constrain imagination without you knowing it. But the costs of “finding out” are high.
New remote and hybrid flavors of work make this easier! The pandemic made a lot of people realize they are essentially freelancers with a single client.
I first wrote this as a thread on Twitter in April 2022.