Lately people have been telling me that I've been giving off "Quit Your Day Job" energy when I talk with them.
That's to say, after people talk to me, they start to think, "...Should I quit? Is there a better way to get it all done? One that I'm not seeing?"
What's interesting is, in most of these conversations I am not selling people on the glossy promise and potential of fractional work. Quite the opposite, actually. Most of the time, I'm lamenting something.
I'm throwing shade about a project gone sideways, or about too many things too do with too little time, how stretched I feel with a lack of money or resources to get the work done, all with a sheepish acknowledgement that yes, indeed, I just can't seem to stop myself from picking up new projects (and project teams) like Pokemon cards.
And of course also the near-constant nagging dread of, "Am I spending my time and energy on the right things? Is this it?" Not to mention the perpetually present seeds of doubt reinforced by every risk-averse person in your life. Seriously, when I called my brother yesterday to ask about what to get his kid for Christmas, is response was:
"Oh. That's why you're calling? I thought you were going to tell me you finally got a job."
"Nope!" I continued along brightly. "I'm still just...doing all the things, all the time."
But despite all of the sticky cinnamon roll twistiness of the cost of carrying a portfolio career, people keep getting curious anyway. They keep wanting to know more about how to try it on for size themselves.
That people are feeling compelled–inspired, even–to want to quit, even while actively listening to my litany of problems with my side quest life, is an indication to me that these single quest, 9-to-5 jobs are not enough.
In other words, maybe, we all need side quests.
Converting tech trauma into viral content
One of my favorite things to see is when someone successfully converts one of their side quests into their main quest.
Back in 2017, I got to know someone named Alexis Gay when she was deeply embedded in the throes of tech company monoculture in San Francisco. At the time, when I was on a work trip out West, I didn't have a ton of near-peers in my weird niche of VC portfolio building work, and I was just grateful that anybody wanted to take a little bit of their time to show me a little bit of the city.
We swapped battle stories from our respective times in sales in tech, and troubleshooted a few strategies for professional growth and development. But we also bonded over Broadway musicals, and how she carried skills as a performer from her college-led upbringing as an entertainment and media aficionado into her role in tech.
I remember thinking at the time, "Wow. What an interesting example of how you can literally apply skills from any domain, into any other specialization area."
A few months later, I got an email from her that she was leaving that job, at a company she now refers to only as [REDACTED], to pursue a career in comedy. She sent along with the email a couple of links to comedy videos she'd been producing and publishing along the way thus far.
I remember thinking: "Wow. What an interesting pivot."
Well. Seven years and many hundreds of online videos and IRL performances later, I saw her perform a sold-out comedy show at the Soho Playhouse last night, a show called Unprofessional, which is (coincidentally), all about the strange and bizarre journey of finding yourself while finding yourself out of place in a job. The room was packed, the energy palpable. With a decent representation of fellow tech workers in the audience, her story hit perhaps a little too close to home for some.
We've all had that colleague who takes work one step too far. That manager who's weird emoji use drives you up a wall. The elusive promotion that gets dangled like a stick but never quite ends up looking like what it should. Alexis took these all-too-familiar pains and turned them into comedic gold.
Essentially, she converted her side hustle into a career.
A side quest on the side quest: In case you aren't able to see Alexis Gay perform IRL on this tour, you can also catch her online content. Her Instagram feed is very funny.
Big talk at 10:38 a.m. on a Tuesday
A few weeks ago, I got an unusual email from someone I hadn't spoken with in a few years. She asked to hop on a call to talk about something, and when we did, she had just one question:
"How do you find purpose?"
I reeled back with the enormity of the question. At 10:38 a.m. on a Tuesday morning, I was still just midway through coffee cup #2.
"I'm sorry, what?" I asked her to clarify.
"You know, I've been reflecting recently on what I want to get out of my life, and my work and all of it, and I realize that it's purpose I'm after. You seem to have found yours. So how did you do it?"
I laughed out loud, half-expecting the conversation to pivot direction. (It did not.)
And then slowly, I shared with her the circuitous and windy road of the past four years of my career, which has carried me through a dozen-some jobs across half as many industries. My professionally promiscuous era, if you will. I explained how, over time, when you start and stop enough things in quick succession, you can start to see the things you come back to, time and time again. In that way, my work life started to feel a little bit like Chidi and Eleanor's inevitable bond in The Good Place. No matter where you start, you keep finding your way back home.
Like any self-directed journey, there’s limited value in trying to extract your own themes from someone else's anti-pattern. Purpose is personal, often emerging only after a period of restlessness—or even a decisive break—followed by persistent experimentation.
That’s exactly what happened to Alexis. And it’s becoming clear to me that more people than ever are ready to cut loose and try something different.
So if you're looking for "Quit Your Day Job" energy, I'm happy to give you that. Maybe you do need to leave that job that’s holding you back. Or just open up space for a few new side quests that have been taunting you for years. And maybe, seven years from now, it'll be you telling your story to a sold-out room, showing others how you found your way. I hope to see you there when you do.