Into the pathless path
in which we lose the plot (again)
Have you met the manager in my head? They cluck their tongue at me while I enjoy an afternoon walk; you should be working, they pant, only five paces behind me. The manager in my head sends me a Zoom invite while I’m in the shower. Your Q1 performance was terrible, they say, without so much a hello. What’s your improvement plan? It scoots over while I draft my novella. How can you do this in 50% less time? During a mind-altering conversation with a new friend. You should post this on LinkedIn. For thought leadership.
While writing this substack, even. The manager in my head, rolling their forked tongue in my ear, hissing: YOU SHOULD MONETIZE THISSSSSSSSS
The manager in my head uses too much spit.
I’ve been wanting to write about my thoughts on work for a very long time. But in those first months after I quit my full-time job — my “dream job”, at least, the closest thing at the time — everything I wrote felt disoriented, choked with too many vines.
I was full of disappointment, because it didn’t work out, despite how badly I wanted that path to go on forever. Full of grief, because it didn’t.
A year later, I can say this has been strangest, scariest, but most expansive year so far. I’m struck by weird bouts of giddiness. I do silly little dances. Think, “god, I fucking love my life.” Then come the days I feel full of carnivorous dread, a pitcher plant drooping in the blaze of the sun.
I’ve always been more of an indoor bitch. But these past 6 months have me feeling like an explorer — stumbling out of the weeds, pebbles in my shoe, face swollen from pollen and insect bites and mere snatches of sleep. It hasn’t been pretty.
But here comes the view.
I’m twenty years old and start my first big girl job. This after a soul-crushing job-hunt post-grad that trickled into a month and then three. While I wasn’t particularly jonesing for the role, I was sick of feeling like a leech in my own household. I promised I would keep my head down, do the work, be the obedient little soldier ant foraging in cafes for the Big Bosses.
But something strange happened when I signed that contract. In her show Quarter Life Crisis, comedian Taylor Thompson recounted something similar when her fiancé slid a ring on her finger. Floating through Target in a daze, thinking:
“Am I… better than everybody???????????”
Taking the elevator down my shiny BGC building, strapped in heels and laptop bag, something awful inside me unfurled its shaggy wings. My steps CLACK-CLACK-CLACKED across the street. I walked faster. Preened.
When I realized we use jobs as shorthand to communicate our place in the world, it became clear to see why building careers — and losing them — could feel so primal. I was lost in the sauce, swimming in the nectar of high productivity and KPIs and social impact!!!!!
I didn’t realize I was caught in the trap of it until losing my Government Assigned Worth Card.
“Oh, you’re a manager?” Starry eyes. “Tell us more.”
“Wow, a comms director?” Approving bobblehead nods all around. “That must pay well.”
“Freelancer?” Slight tilt of the head. Somehow, in those seconds I felt like my membership card had been revoked; bored gazes already drifting away from me, the trespasser. “Ah…”
In school, we were taught to be men for others. A job couldn’t be just a job — it was something you did to express the full tapestry of your soul. A perfect container, and we just had to find it!
So on we go, hunting down the dream job, the perfect job. The one with the job description God himself scribbled in our code, the one that could unlock the real work of our lives, let us enter into secret societies and gym memberships and company pantries that overfloweth.
And maybe then things would finally make sense. And we could finally stop looking — the hardest, bloodiest work of all.
The days transitioning from a 9-to-5er to working for myself boggled me. All of it. Until now, I can’t explain the sheer exhilaration and confusion I experienced. All of a sudden I had so much time and money on my hands and no idea what to do with any of it. I was free to choose my projects, my schedule. But was I, really? Free? What did that even mean, anyway?
For a time I glorified the idea of freelancing. This, I was convinced, was the way to live. I’m grateful for how the profession opened up a new path for me — a path I want to keep exploring for a long time, because it taught me that no matter what happened, I could make things work and return to a spirit of creativity and love.
Then things began to chip away, like the bad paint job it was:
Freelancer influencers regurgitating famous Gary Vaynerchuk quotes - Hustle! You gotta wake up earlier than anyone else! Gotta EAT, SWEAT, SHIT, and BE your business (don’t you quote me on this). Haven’t I had this flavor of corporate cake before? The infinite upskilling race. Multiple streams of income. Six figure earner in three months! One client and then two then thirty, because obviously you want to start an agency, too. And then you’d be recession-proof. Anti-ti-ti-ti fragile. You can rest easy, eat sushi on a cloud with Jesus, whichever deity you wanna hang out with. But you have to want it, and bad. Why can’t you want it, Andy? What’s wrong with you?
In an online conference for aspiring freelancers, a dude in a black turtleneck bathed in bisexual lighting smiled and introduced himself as a “Future Agency Owner and Six Figure Earner.” He encouraged us to do the same.
“You’re not just a freelancer,” he said. “You’re so much more. This is just the beginning.
What the fuck, I thought. I literally just got here, bestie. What do you mean there’s a career ladder for freelancers, too?
All I wanted was to get out of the race. How have I somehow never left?
In his book, “The Pathless Path,” Paul Millerd recounts a time of upheaval after several career shifts, from a fancy corporate job to freelance consulting and back.
He shares, “With every new job, I convinced myself I was thriving. But what I was really doing was trying to escape feeling stuck. I was too afraid to have a deeper conversation with myself. The kind that might pull me towards a different kind of life.”
Even when I began hitting my money goals on 15-hour work weeks, I felt restless. All these options, and all I could muster was a big fat “MEH.”
C’mon, financial freedom. My beautiful but terribly intimidating friend. Weren’t you supposed to give me the cheat code? Where’s the field guide, buddy? Wasn’t I just supposed to know what to do, once I got on the other side?
I wanted a big, stupid, brave life; instead of building one, I built — well. A business. I guess I thought freelancing would hand me the script just like that.
Again, I had fallen into a trap. I had relied on a career to provide me the easy way out. The silver keys to the question: What’s worth doing?
Something you did not because it was brag material at the barkada reunion, or the extended family group chat. Or because it paid really fucking well. Worth doing not because anyone else thought so, but because I decided it was. My own personal enough. My own slap on the back, you-worked-hard-today-Andy, whispered at the end when the stage lights start to dim and everyone you love goes milling out; soft enough only I can hear.
The point, Paul shares, isn’t about “escaping work.” Nor is it about “living an easier life.”
Burned out, disillusioned, isolated era Andy — I don’t blame her. Not for her anger, for our collective “I don’t dream of labor” dreams we feverishly dreamed alone in our beds at the end of another hellish work week. I wanted to escape many things — but being a real person, in a deep conversation with the world, was never one of them.
When I came across this article, Writing Your Own Obituary Can Teach You How to Live, I knew I had to turn back. Wouldn’t be the first time contemplating my death helped me fine-tune my path. Easier to know what’s worth living for when you think about what’s worth dying for.
As I wrote my obituary, a few things kept coming up: creative community, justice, lifelong learning, pleasure, and expression.
Ah, I thought. There you are.
Now how could I consciously design my life around these things? Instead of letting some career or job or ideal client be the end-all of it?
“I was slow to realize this, but I know it now,” Paul shares. “The work I get paid for may shift over time, and it may or may not involve the things that I want to keep doing. But what I want to keep doing, such as mentoring young people, writing, teaching, sharing ideas, connecting people and having meaningful conversations, is worth fighting for.”
These past few months have expanded my definition of work. It’s not just things you do for money. It could be whatever you pay most attention to; what keeps you moving; what you worship; what you build, even when no one’s watching.
Most of all, the real work of our lives is right here: the confusing, uncomfortable, but conscious untangling of it. The lifelong journey unearthing what values you hold true, then trying out new selves, to weave something that lets you do more of it. The things worth doing. It’s not something you can just pick up off the shelf, ready-to-go — I mean, I guess you could. A store-bought life is fine. Said no one ever!!!!!
The manager in my head is inconsolable. What about this? Have you forgotten this? they shriek, tapping the ten-year life plan my 20-year old designed in PowerPoint. I invite the manager in my head out for a walk; they could use some good air once in a while.
What’s on the shelf
If you’re feeling anxious about all the possible paths you can take in this lifetime, here’s a podcast episode rec, Time Management for Mortals — “Rather than focusing on rote efficiency or productivity, Burkeman calls on us to embrace our finitude and surrender to the rhythms of life, so that we may “end our struggle with time”—and live with “more accomplishment, more success, and more time spent on what matters most.”"
Reading Chen Chen’s juicy debut, When I Grow Up I Want to Be A List of Further Possibilities ❤️🔥 Part 1 and it’s got me feeling so emo already
Other fun detours
Link for those who wanna take a stab (haha) at their own Write your own obituary exercise — “Think of the giants in your life. You are that now.”
I was spurred to pick up this Substack because I was so inspired by my writing friends and their brave, beautiful writing! A big fat thank you to them. And if you haven’t, go check out their projects: Project Orange, houseblessing, and Cup of Insanity!
Attended a climate writing workshop with Green Dreams of a Generation PH. If you’re a Filipino youth interested in submitting to a climate anthology, go check it out! Submissions close May 15.
Here were some of workshop’s fun generative prompts. You might wanna try them out too:Write about a character in the future who’s looking at an abandoned parking lot (a remnant from the past society) and describe their thoughts/feelings.
Your character is someone in the future, writing to someone in the past. It’s their last letter, and the letter can be either positive or sad. What’s in the letter?
Write about a community that has supernatural abilities as a result of their connection with the environment. When they lose their power, how do they feel? What do they do?
Thank you for reading, friend! I’d love knowing what you thought. And if you’re on the pathless path too, many hugs! It’s rough out here — but the view, yeah?
Much love,
Andy
Welcome back, queen! 💖 I love love love this post, thank you for your words and insights 🥺