The unemployment fund

One of the best career decisions I've made over the past decade is saving up a large cash position to allow me to take on more career risk.

I've been extremely privileged to have worked at every job I've ever held. Save for a few pre-teen years where I quickly realized physical labor was not what I wanted to be doing, I've always worked remotely.

Better yet, every single job I've worked has allowed me to set my own hours within reason (at worst) or been completely async (at best).

Trying to sculpt work you like into a job you love isn't easy.

Asking for a raise is scary. Asking not to be included in meetings anymore is scary. No matter how much value you're able to deliver, these non-traditional asks are often new territory for even the most understanding and progressive bosses.

Managing employees is difficult. I respect that. But early on in my "career"(probably during high school, when I hard committed to working online) I decided that I wasn't going to settle for jobs that didn't afford me control over how and when I work.

My work life has been 100% async for the past ~5 years and I don't think I can ever go back. Naturally, this makes finding work 10x more difficult.

That's where the unemployment fund comes in.

The unemployment fund exists to buy me time and courage. It affords me X months of fully covered lifestyle expenses, so I can risk losing a good job when I'm trying to find a great job.

It would have my back if I were to wake up tomorrow to an email from my boss, informing me of a new company-wide initiative to have a daily standup call. Or if budget cuts butchered my effective hourly rate.

When your life is prepaid 6 months/9 months/12 months++ in advance, you have the option to be bold and ask for the things you really want.

Is it still scary? Yes.

Does it suck if you don't get the outcome you want? Yes.

Watching your unemployment fund burn down as you email founders to ask them if they'd be open to an async work environment is about as fun as chewing sand.

I want to form longterm relationships with people who not only appreciate the quality of my work, but who get excited about watching me level up while I'm doing it, on my own schedule.

The unemployment fund, miraculously, has allowed me to pass up on good jobs that check most of my boxes to pursue great ones that check them all.