Want to Quit Your Cushy Job?

You’re not crazy. You just want to get paid to learn new stuff.

Sending off a premeditated resignation letter was the best decision of my life.

No job lined up, only one freelance gig to fall back on, and just enough savings to survive a few months without a stable income. It went against most conventional wisdom and voices of reason among friends and family.

If you don't like your job but are able and willing to learn new skills, here’s the sign you’ve been waiting for. It’s time to find better ways of spending the time between 9AM and 5PM.

Be prepared to ask yourself some hard questions.

What the heck was I doing?

I was letting my first “director role” and $130K salary go for…nothing.

But what seemed like nothing was actually a lot of somethings. My brain was craving to learn new skills, preserve my mental health, and surround myself with people who didn’t want to work their lives away.

“It may be that when we no longer know what to do we have come to our real work, and that when we no longer know which way to go we have come to our real journey.” — Wendell Berry

Catchphrases would appear as giant red flags behind faces on Zoom meetings, reminding me of the stark contrast between the team’s culture and my ambitions.

• “Feel free to call or text me on PTO!”
• “What’s the purpose of this meeting again?”
• “Let’s just throw it in a PowerPoint deck”

At first, I blamed utopian headlines and stories popping up in my LinkedIn feed. The Great Resignation and Passion Economy had painted a vivid picture in my head. I could just leave my job and ride off into the sunset, right? Passive income would find its way into my life.

Wrong.

Eventually, but there would be famine before the feast. It was time to take risks, but small and calculated ones. Not ones that would return me to a life of couch surfing. So I started ideating and prototyping by asking myself:

1. Why do you want to leave your job?
2. What would you do if money wasn’t an issue?
3. Do you have a clear vision for what you want to do?
4. Are you confident that you have the resources and skills to go out alone?

Find answers that reconcile your past and present.

The hamster wheel suddenly flung me out of the cage.

I had been flirting with setting up a 1-on-1 with my manager for weeks now. Every time, seemingly rational thoughts would swoop in and force me to delete the calendar invite.

Until self-examination revealed I wasn’t crazy.

I wanted to quit because my learning curve had stagnated. I thought the director's title would usher me into a new world of learning and growth. I thought managing others full-time would be an insurmountable task, but quickly realized it wasn’t rocket science. This wasn’t my first rodeo — I had hired and managed plenty of freelance talent, along with a few interns.

It also felt like office politics had become a part of the job. Maybe this was due to working at an agency or on a book of business in New York. Every project transformed into a client appeasement roadshow. It felt like a chokehold. We had no visibility into what was working and were receiving instructions from people who didn’t know what they were doing.

There was no ownership over results.

The final straw was when I stumbled upon the field of product marketing. Having been a freelance writer and marketer for B2B tech startups since college, I felt like I had the experience and skill set to succeed in this world.

“Anyone who stops learning is old, whether at twenty or eighty. Anyone who keeps learning stays young.” — Henry Ford

Most importantly, I was excited to fill any gaps and learn new stuff. My previous jobs at startups had set me on fire, put my skills to the test, and introduced me to awesome people.

People who loved their work, but didn’t want to work all the time.

Remote work forced us to realize what matters.

And that’s a good thing.

Life is too short to commute two hours every day. It’s too short to spend it with people that have different value structures. It’s too short to stagnate and stand idle when you could be learning new skills and earning at new levels.

You want an asymmetric return on your time. No one wants to rent their time for a paycheck — as Naval puts it, “you don’t get wealthy renting out your time”.

So that’s what I set out to get.

Within two weeks of having put in my notice, I found that opportunity. As a Senior Product Marketing Manager at Chili Piper. They offered a similar income threshold, along with some serious equity.

This wasn’t the big break I had originally envisioned, but damn if it didn’t feel close. I start in two weeks — and I’m excited to put in more work. Call it eustress.

“One of the secret benefits of using remote workers is that the work itself becomes the yardstick to judge someone’s performance.” — Jason Fried

Our relationship with work is fundamentally changing. It’s no longer about paying the bills. It’s about loving what you do, feeling valued, and believing that you’re making a difference. A positive dent in the world.

I’m not a financial advisor.

But I can tell you that if you have the will to learn and save, you’re never trapped in a job.

“You have to do what you dream of doing even while you’re afraid.” — Arianna Huffington

Feeling stuck? Here’s how you can carve your path to freedom:

1. “Prototype” what your vision looks like by taking small steps and asking tough questions. Can you spend a day working for yourself? Try it.
2. Don’t chase titles. They may help others take you more seriously, but in the long run it won’t matter. Prioritize learning over status.
3. Reflect on your experiences thus far and get your story straight. Look for clues telling you what you enjoy doing most (and can get paid for).
4. Mental health dictates overall wealth. Preserve it at all costs.
5. Look for asymmetric returns on your time by taking calculated risks.
6. Surround yourself with people that you look up to. People that will level you up.

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