I quit my dream job. Here's why.

Anyone can follow this advice

I was the 5th employee at a Series A tech startup with over $25m in funding and a $100m valuation.

It was the ideal situation.

• Good Equity? Check

• Tier A investors? Check

• Company growth? Check

I left because I finally took my own advice.

It’s advice anyone can follow, but few people actually do.

It’s why most people are upset with their lives.

First, what I learned.

• Cold calling. Must have skill for any non-technical person. I averaged 45 calls/day for 10 months. 30 days/month x 10 months = 300 days — 100 weekend&holiday days = 200 days x 45 calls ≈ 9000 calls. They say doing something 10,000 times makes a master. I was damn close.

• Built playbook and strategy for marketing, sales, and customer success. If you are an early startup employee, please document things. Mercedes Bent told me this in my first month and it was essential in onboarding new employees. Document messaging, what works vs. what doesn’t work, meetings, product strategy.

• Closed a 6 figure deal. Getting big wins is important to validate your hard work.

• U.S. public education needs work. It isn’t one party’s fault. The system is broken. The people running the system are misaligned. Parents are misinformed. Our kids live with the results.

I was a 23-year-old cold-calling superintendent to sell them on our little startup’s vision. Our vision? Change online high school education.

Superintendents average age is 55. They are highly educated and answer to taxpayers. These are high-stress individuals making million-dollar decisions every day. 

Superintendents are not risk-takers. Their job rewards them for playing it safe; not taking a chance on a venture-backed startup disrupting the online education space.

Convincing superintendents to believe in our vision was hard, but it felt impactful. We were disrupting a system that needed disruption. But, something was missing. 

The first few months at the startup were exciting. It was a few people trying to figure shit out. There was one goal → grow. As the company grew the company changed. My role changed. I didn’t have the autonomy I once had. I had quotas, arbitrary deadlines, and hierarchies. It wasn’t working for me.

I started in May. By October my mind was elsewhere. Why?

I downloaded a metamask and went DEEP down the crypto rabbithole.

• Minting and collecting nfts

• Participating in DAOs

• Going to crypto networking events

• “Investing” in fungible tokens

• Reading crypto newsletters and blogs

• Listening crypto podcasts

The other part of my free time was writing and tweeting. I never really had time to focus on both. My writing was half-baked and I wasn’t a full crypto participant.

Time went by faster when I was down the crypto rabbithole or writing a twitter thread 4 people read.

I wasn’t fully bought into the startup. I wasn’t happy with my day job and it made me unhappy. I started to doubt my purpose. I felt trapped. 

You do not have to be good. You do not have to walk on your knees for a hundred miles through the desert repenting. You only have to let the soft animal of your body love what it loves.

This quote is from Mary Oliver’s Wild Geese.

You know someone that’s not satisfied with their life (maybe it’s you). They hate their boss and want to do something different. Everyday they make the decision to stay. Everyday people fight their true nature. Why?

Because they don’t follow Mary Oliver’s advice.

DO WHAT YOU LOVE. 

Do what your heart is telling you to do. It’s simple in theory, but hard in practice. 

We like a comfy salary. The certainty a job brings. Name dropping our employer at the dinner table.

But, if you… 

Have a hobby you are passionate about. Love writing in your free time. Have a side gig is bringing you more energy than your full-time job. Feel your true calling tugging on your heart. Do yourself a favor.

Say, ‘FUCK IT’ and quit.

What’s the worse case? You fail and are right back in the same spot you were a few months ago. 

Sometimes, when we’re terrified of embracing our true calling, we’ll pursue a shadow calling instead. The shadow career is a metaphor for our real career. Its shape is similar, its contours feel tantalizingly the same. But a shadow career entails no real risk. If we fail at a shadow career, the consequences are meaningless to us. Are you pursuing a shadow career?

Are you getting your Ph.D. in Elizabethan Studies because you’re afraid to write the tragedies and comedies you know you have inside you? Are you living the drugs-and-booze half of the musician’s life, without actually writing the music? Are you working in a support capacity for an innovator because you’re afraid to risk being an innovator yourself?

If you’re dissatisfied with your current life, ask yourself what your current life is a metaphor for. That metaphor will point you toward your true calling.

I was working in the support capacity. I thought this was how my career was supposed to be. I was avoiding the real work.

That’s bullshit. There is never a good time to quit. Remember that.

If you don’t like the way things are going, change the way you do things.

Here are my goals in the next few months:

• Make my first dollar online. I created a newsletter on web3 + sports called 3SPN. Sign up here to receive the first issue. It’s free.

• Launch an NFT project. In the film space... let me know if you want to learn more.

• Left my parents home. I am crashing on friends’ couches right now. My goal? Don’t go back.

• Stay consistent in writing content and producing TikTok’s. Follow my Substack to stay up to date. 

• Oh yeah, and if anyone wants to hire me to write for them → woxley99@gmail.com

Don’t follow the shadow career.