I’m not a fan of the word “unemployed”. First of all, it’s come to imply that the default state is “employed”, meaning to be an employee, meaning to have an employer. I am not a fan of the conventional employer-employee relationship – I don’t think it’s good for me, even when I have a great boss (which I was very blessed to have for 5+ years in my 20s.)
Social class interacts with “unemployed” in an interesting way. Hardly anybody describes wealthy people as unemployed, even if they don’t have an employer. They might be described as investors, asset owners, landlords and so on. “Unemployed” is a bit of a dirty word for the underclasses. Sometimes you might hear a wealthy person joke that they’re “funemployed”, which is something that a poor person couldn’t possibly describe themselves as, because there’s nothing fun about being unemployed when you can’t pay your bills.
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I don’t really like the word “freelancer”, either. It originally meant “hired mercenary”, and now to me the word brings up the image of someone who’s doing small jobs for other people. I find it too… provincial. It doesn’t really inspire you to dream big. While it’s not quite as clearly “underclass-coded” as “unemployed”, you would never hear a wealthy person describe themselves as a freelancer. In fiction, The Witcher could be described as a freelancer. Because he doesn’t have a lot of money himself, and he lives from gig to gig.
I’m moderately comfortable describing myself as an “entrepreneur”, which was once kind of a hoity-toity way of saying “a person who does stuff”. But this word too has accumulated connotations that I’m not a huge fan of. What do you think of when you think of an entrepreneur? I think of restauranteurs, business owners, fitness instructors, hairdressers and so on. If you’re starting a company that’s meant to be growing, you might describe yourself as a founder/CEO. I don’t really like any of those words. They’re all a little too “rigid” for my liking.
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Through trial and error I’ve found myself describing myself as a “feral free agent”. If I find myself needing to navigate a corporate environment for some reason, I might describe myself as a marketing consultant. Casually, I like to think of myself as a busker, a street preacher…
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(Original thread, oct 2021) My relationship with employment has always been kind of funny. My parents ran their own business all my life, so I always took for granted how free and independent-spirited they were. Thinking on it more now, school was such a bizarre contrast to that.
my parents never had to do homework or study or pass tests. they also never worried about vacations or days off or promotions or what their bosses or colleagues would think. they basically did whatever tf they wanted. my dad would come home for lunch all the time and take a nap.
I mean they did have work to do. And they were kinda stressed all the time, I think more than strictly necessary. But there was such a direct relationship between the work they did, the $ they made, the quality of their life. And… I absolutely cannot imagine my dad having a boss
the dominant frame in school, at least in Singapore, is the assumption that you’re going to keep doing tests, keeping jumping through hoops, keep acquiring certificates, wear a tie, go for interviews, compete for a job in some prestigious company where you sit in meetings
and, yknow, like… where in that do I have lunch with my wife and then take a nap? 😂
The dissonance was overwhelming for me in a way I couldn’t quite articulate at the time, and I basically tried to live my own feral independent life in books and on the Internet. I hung out on forums, made my own website, organised rock concerts, criticised the government.
My bet paid off: even though I never went to university, my writing got good enough that people started sharing it around. I got hired to do marketing for a startup, which paid well and had a work environment so relaxed, open & flexible that my schoolmates were shocked to hear it.
On one hand, I will say that I was very lucky and privileged to get such a great boss. On the other hand, I also had put in the work to have a reputation that preceded me. This wasn’t a one-time lottery event. I recurringly get fantastic opportunities, recognise them, follow thru.
I worked 5.5 years at the startup, helped 100x the blog traffic from ~1,000/mo to 100,000+/mo. It was intense work, I had a lot of freedom to do what I thought was right, I learned a lot. I wrote hundreds of articles for work, and I also wrote hundreds of essays on my commutes.
Looking back I think that was the most Bad Motherfucker thing about me in my 20s. I used to have a blog that regularly went viral (you can still find old tweets of people sharing my stuff from a decade ago) but eventually I got sick of it and walked away… and wrote for myself.
I watched Hamilton recently and the idea of “writing one’s way out” really stuck with me. Other writers have said similar things too, eg Jeanette Winterson. “Mere” writing is still powerful technology. You can write your way out. You can literally rewrite your life. I did.
Anyway so! I’ve always had many irons in the fire. While I was working I also accidentally ended up starting a T-shirt business on the side. While I was writing I was also building an audience. And when I left my job in 2018 I had enough saved up to give me at least 1 year runway.
this was me reviewing and revisiting my plan a month after I left work. in retrospect I can say with even more confidence: this is a good fucken plan.
anyway so here I am now, aged 31, doing whatever tf I like, which right now is mainly working on writing a book that I find intellectually and spiritually challenging. If I need money I can do marketing consulting for clients. And if I want, I can take a nap. Whenever tf i like.
to be continued