Stepping off a Rocketship. Strapping on a Jetpack.

Why I’m “going independent” for the next phase of my career

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A few weeks ago, I made what some will see as a strange career decision – I left my full-time role at Guild to “go independent.”

Leaving a steady job three months after having a baby is admittedly pretty insane. It’s even crazier when the company you are leaving is a rocketship that is hitting escape velocity.

If this were any other newsletter I might just leave it there, but many of you subscribe to The Jungle Gym for strategic career advice, and you deserve to know whether the person you are taking advice from is unhinged.

I don’t think I am, but that’s for you to decide.

Joining Guild

Those of you who have been reading this newsletter for a while may remember a post I wrote last spring about conducting a job search at the beginning of the pandemic.

Despite my job pipeline exploding (in a bad way), I was lucky enough to land at the company I was most excited about – Guild.

As it turns out, working for Guild was even better than I imagined. The company has strong product/market fit, fast growth, amazing leaders, and a business model that incentivizes doing good. While no employer is perfect, Guild has been as close to an ideal place to work as one can find. I couldn’t be prouder of everything our team has accomplished and the economic opportunity we’ve created for America’s frontline workers.

This begs the obvious question– why am I leaving?

The clock starts ticking

Going into paternity leave, I had no intention of making a career change. But, having a baby does funny things to your head. It limits the number of hours you can focus on work and reminds you that your time on earth is finite. Having Cooper caused me to start considering how I wanted to spend the next few decades of my career.

It was around then that I read Packy’s article: The Great Online Game. It lit a fire in me.

The Great Online Game, as Packy describes it, offers something of an alternative to traditional employment. Rather than relying on a single employer for money, relationships, and professional development opportunities, ambitious knowledge workers can get their needs filled by working for the internet. Unlike most jobs where your trajectory is constrained by the operating system of a single employer, working for the internet offers the promise of uncapped upside.

By publishing this newsletter I had started been playing the online game. This newsletter has served as a magnet for new friends, speaking gigs, and even investment opportunities. For the next phase of my career, I decided that I wanted to get serious about playing.

Building a plan

While that sounded nice, in reality, we had a new baby who needed diapers and childcare. While my wife has always been supportive of my career choices, I didn’t think she’d be particularly excited to hear that I was stepping off a rocketship to drift aimlessly off into space.

So I hatched a plan.

I started dreaming up side hustles that could replace my income from Guild. 

  • Courses. 

  • A talent matching service. 

  • SaaS products.

I needed something I could build on nights and weekends that wouldn’t impact my performance at work, or as a new dad.  I calculated that if everything went well, it would take me at least a year to build something that could replace my income.

Serendipity strikes

When the higher powers of the universe condone your plans, they sometimes send help to accelerate you in the right direction.

For me, help came in the form of a few Web3 investments that exploded (in a good way). By the end of the summer, I suddenly found myself with a crypto portfolio that dwarfed my annual compensation.

While the investment winnings were a boost of confidence, I didn’t want to depend on the volatile crypto markets to pay for diapers. Fortunately, a good friend from Eclipse Ventures reached out to offer me a part-time opportunity to help the firm incubate a new business idea. It was exactly the type of work that felt like a fit for the next phase of my career.

The successful investments combined with the ideal launch opportunity gave me the courage I needed to make the leap into independence.

So, what exactly am I doing?

The short answer is too many things. But below are the main ones:

  • Incubating a business idea with Eclipse

  • Advising/consulting for a few startups (including Guild!)

  • Continuing to publish this newsletter

  • Launching a talent matching service 

  • Collaborating with some friends on a Web3 education idea

  • Managing a budding portfolio of startup and crypto investments

It feels too early to put a label on all this, so, for now, I’m going to say that I’m strapping on a jetpack to go exploring.

What this all will look like in three to six months is still anyone’s guess, but that’s what makes it so exciting. Working for a single employer, my career had a constrained set of outcomes. Now the opportunities feel endless.

Guiding Principles

While I’m not sure exactly what I will be doing, I do have a handful of principles that I’m using to guide my choices during this next phase of my career.

1. Optimize for energy – As someone who writes a newsletter for fun, I tend to get energy from activities that feel like “work” to others. That said, I have a pretty low tolerance for work that doesn’t feel energizing. In this next phase of my career, I aspire to spend as many hours as possible in a state of focused excitement.

2. Work in my “Zone of Genius – When I reflect back on my peak work experiences most of them involved three things:

  • Lots of creative Ideation

  • Executing strategy that I played a role in crafting

  • Collaborating with people I admire

I find that whenever I’m working on projects that combine these three elements I tend to maximize the value that I create for myself and others.

3. Win together – One of the best artifacts of my career is a professional network full of kind and talented people. One of the things I’m most excited about in this next phase is collaborating with more of them on projects.

4. Build high-leverage income streams – While I have never been particularly motivated by money, I do want to ensure that the people I care about have enough freedom and financial security to pursue meaningful lives. The best way to create those conditions, without sacrificing my other principles, is to build a few high leverage income streams where the output of money isn’t entirely dependent on the input of my time.

5. Keep work in its place – One of the biggest challenges of independence is putting boundaries on work. Because I love what I’m working on, it’s easy to let work creep into time with family and friends. At the end of the day, that’s not the person I aspire to be. Going forward, I plan to give myself plenty of three-day weekends and vacation days to spend time with the people I care about.

Should you take the leap?

Going independent is not for everyone. Companies offer lots of opportunities to grow your skills and scale your impact. If you aspire to manage large organizations or just want the safety of a steady income and benefits, then working for a single employer makes a lot of sense.

That said, if you are interested in strapping on a jetpack of your own, I don’t think it’s as scary as it seems. For those who are curious, stay tuned! I’ll be sharing learnings from my interplanetary adventures in the months to come.

In the last issue, I announced The Jungle Gym Talent Collective, a service that matches talented people with interesting opportunities at fast-growing companies.

So far, the response has been amazing– we’ve had over 150 people sign up to recieve intro requests to our 130+ fast-growing partner companies like:

  • Shopify

  • Figma

  • Patreon

If you’re hiring or looking for your next job, here are a few ways you can get involved:

  1. Get intro requests – Regardless of whether you are actively looking for a job right now, you can fill out your information to get intro requests from our fast-growing partner companies.

  2. Get talent drops – Is your company hiring? Tell us what roles you are looking to hire for and we’ll send you a monthly drop of candidates who are open to new opportunities. Companies just play a small bounty when a successful hire is made.

  3. Recommend a friend – Do you have any talented friends who are looking to make a career change in the coming months? It would be amazing if you could send them over the sign-up form (if you recommend someone, please let me know, so I can say thanks!)

If you have any questions, please don’t hesitate to drop me a note.

If you enjoyed this issue of the newsletter, I'd really appreciate it if you could forward it to a friend, family member, or colleague who you think might like it too.

Or, if you'd like to share it on one of your social networks, that’s always great as well.


Until next time,


Thanks to those who provided feedback on early drafts like: Araminta Robertson, Ashley deWilde, Daniel Sisson, Stacey King Gordon, Stew Fortier and Tom White.