I've been a freelancer longer than any other thing in my life

The longest job I've ever had, minus maybe my paper route (?) was 3 years and 8 months.

It was my first "real job" out of design school and really now the only one. I worked retail in high school, I had a summer day job between school years, but this one job was my first 8:00 - 4:30 commuting, office desk having, coworker chatting, yearly salary paying, infinite timeline void staring day job.

3 years and 8 months.

And that was, as of writing this here in july of 2019, 3 years and 8 months ago.

Which means that I've officially been freelancing longer than any other thing in my life.

Technically high school was 4 years, okay, whatever, but I mostly slept through that so it barely counts.

It's wild even to think that the "longest thing" is that short, too. Like maybe we should count the 12 grades + kindergarten + college as some sort of 15 year stint so it sounds more cohesive. But really: it's like your life actually starts after graduating so in some sense I'm only 7 years old here, and this represents the doubling point of the first thing.

And it's going good!

So I wanted to sort of reflect and think about it all here in this weird not-quite-anniversary journal.

Outside of Time

I think there's some fundamental paradigm shift - real or imagined - that happens in the transition where the entire world's rhythms change for you.

When I worked at my job I didn't really leave my desk except at 10:00, noon for lunch and 2:30. The two breaks I quickly turned to walking in a loop around the yard because there really wasn't anywhere to go from a quiet factory in the middle of a light industrial park, and I surely didn't want to sit in my awful chair any longer than I needed to.

There was a Tim Hortons a parking lot away. I ate a cinnamon raisin bagel every morning. They'd see me walk in and start preparing it.

Like school, there's this clear division between free hours and inside time, be it a classroom or office, such that any time you're out in the opposite place / time it feels substantially weird.

Being at school at night for plays or parent teacher interviews is bizarre. The lighting is all different, each hallway an uncanny version of itself that we see every day. The same people, but in different clothes. Everything just feels off somehow.

You ever run into your teacher at the grocery store on a weekend or something? When you're a kid, I guess you just assume they live at the school and shut down for night or something. They eat pop tarts too?

Being out in the world for a doctors appointment while you should be in school / work is similar. There's so many cars out in traffic! Don't they also know that it's officially Work Time and the streets should be empty?

It always felt like I was doing something illegal, like someone should stop me or something.

But the world exists outside of that dichotomy, and now I'm one of those others.

And it's great to get groceries at 10:37 on a tuesday morning, or go to the gym in the afternoon, I schedule dentist appointments for whenever it's silent, but it is a palpable shift to be outside of those clocks.

I've gotten used to it now, but I still remember the feeling of the before.

It's funny how substantial it felt then.

Outside of Money

This one isn't necessarily a freelance specific shift, but it is a shift in my macro life from growing up and advancing the now-metaphysical career ladder: money had changed so much over these years.

I talk about my money story a lot so I won't repeat it, but the main thing is that, at a certain point, your money also experiences the shift that your time does: it gets abstract, and abstract feels infinite.

And that's not to say it's literally infinite - there is a number in those accounts and it is decidedly finite - but at a certain point it becomes a flow more than a value: I don't really care what the number is, and it will go up and down by itself over time even if I do nothing, but I do care about the swings in my income and my spending as a ratio of each other.

That relationship also changes when you don't have a salary: a slow drip of steady, constant, counted upon, future plannable money.

It feels like a bicycle or something: you're pedaling and each pedal gets you X amount down the road, and you just hold that pace forever, maybe someday each pedal will get you slightly more distance per turn.

The career ladder is that couple percent raise every year: a little bit faster, a little bit further. Steady steady.

Freelancing is erratic: you're pedaling and each pedal is a different distance, there's hills both up and down where you pedal harder or not at all, sometimes random stuff happens and it feels like a rocket boost totally unrelated to your biking but you never know when it'll cut out suddenly. Flat tires. Rain clouds.

The career ladder is wild self-made modifications to the bike. You figure out a weird chain for yourself and now you pedal once and can glide for miles. Will that work next year? Who knows, but it does right now.

I go months sometimes without any income at all, either because I'm not working (by choice or otherwise) or because I am working and waiting for the money to come in.

But the bills are always monthly.

I've been extremely fortunate that I've never really been close to those things colliding, but ask any of my close friends during some of those eras and you'd learn just how obsessed I was about runway.

Even before, while in the job, I was slowly planning an escape to quit / try this anyway and was just so worried about failing, not making ends meet and that spiraled into all sorts of worst case scenarios that are obviously irrationally silly.

But they were real at the time.

It's funny how substantial it felt then.

Outside of the World

There's a quote that's something like "a bird doesn't need confidence in the branch, a bird has confidence in its ability to fly if it breaks."

Maybe that's nonsense, who knows, but I do think I feel more like that bird now.

I don't have confidence in jobs or bosses or careers - I had a job one monday morning and then didn't that monday afternoon, in what way are jobs secure? - but I do have confidence in my ability to make money and be valuable to people and figure out ways to keep fighting forward.

Which I have to imagine in the end is a much more stable, satisfied, unfragile position to be in.

If you're entrusting your entire stable existence to the hands of some manager - effectively an acquaintance with no real vested interest in you - how much do you trust them? Maybe you do, maybe that's great, but I feel like most folks wouldn't / shouldn't / don't.

I'm not even against employment, there's lots of good reasons for it that get overlooked, but I think having confidence in your wings is useful no matter what branch you're resting on. I think everyone seeing themselves as a perpetual freelancer, even if gigs are true employment, is beneficial. Constantly be moving and looking upwards. Constantly be UNFINISHED