On Leaving My Day Job

January 11 was my last day at Tighten.

Tighten was supposed to be my dream job. Turns out, dream jobs are still jobs. There are people who expect things of you, they reward you if you perform well, and you’re held accountable if you don’t. It’s a dance. You have to navigate projects, productivity, and expectations. There are things the bosses are looking for.

This should come as no surprise. It’s the nature of employment. Someone is not only hiring you to do something, they are hiring you to be someone.

Fortunately Tighten is a self-aware company, and there is plenty of room for constructive discourse, but at the end of the day, like gravity, there are natural laws at play. And resisting those laws is not easy, it’s work.

I think deep down I wanted to escape the laws. For me, they weighed on me daily. There were voices in my head. Expectations I wanted to live up to. Culture I wanted to fit in to. Politics I wanted to pander to. People I wanted to be respected by.

Again, this should come as no surprise. It’s an ecosystem like any other. There is hierarchy. There are dynamics. There are conceptions. There are, did I mention, expectations.

There is a great reward awaiting the navigator of this system. Consistent W2, salaried income. Health care. Employee perks. 401(k) matching. Meals and trips paid for. But lest we not forget. This system nets someone else profit. That someone is not you. You are employed because someone else is making more money off you than you are taking home. Otherwise, it wouldn’t be employment. It would be partnership.

At some point, that realization, coupled with an increasing sense of personal strain, creates potential energy inside of you, building up to the day you make the call. The day you get the boss men on a Zoom call and break the news. The news that you’re moving on.

Ok, so I’m moving on. But to what? To another W2 job? Maybe. To client work? Maybe. To an increasingly long sabbatical? Maybe. It doesn’t really matter, it just matters that I made the move. That I answered the question my bones were begging me to ask: What happens if I break the flow? What happens if I interrupt the continuum? What happens if I strike out on my own?

Well, 3 months later, I can say. Not much. But at the same time, I can say: A whole damn lot.

The weight of employment has been lifted. I’m not waking up each day with the mental load of having to clock at minimum 8 hours. That’s freeing. I also wake up each day with the weight of what could be. What I could accomplish and achieve. That’s a different kind of weight. In some senses heavier. In other senses light as a feather.

Being the sole issuer of my mental stress, and not the recipient of someone else’s has made all the difference. Maybe I’m just wired that way. Maybe other people are better off in the shelter of the W2.

I still haven’t done any client work. I have enough of a cash stash to ride the Livewire/blogging/podcasting/personal-health wave, so take my words with a grain of salt.

But this is how I feel for now. Free. Grateful. Light. Adventurous.

I’ll let you know when that changes. I’d be a fool to say it won’t.

This has been a continuously typed, un-edited reflection. Directly from my mind and into these words. I have to believe there’s some value in that.

Much Love,
Caleb