merry in the messy middle

Candid Christmas: relentless positivity vs the honest nitty-gritty

DALLE’s attempt to illustrate this essay.

In 2023, we live in a positivity pandemic. The cataclysmic fusion of several movements brought us here — possibility preachers on social media, hustle and “crush it” culture, self-help books, even behavioral psychologists like Adam Grant, and the spiritual awakening. In isolation, these forces are often beneficial, but in tandem they’ve coalesced into a tide of ‘relentless positivity’.

There’s an expectation that even in the thick of your life’s chaos, you should remain unflatteringly cheerful. That you should be merry in the messy middle. Turn that frown into a smile. Project that external image of certainty and assuredness. Got laid off? Be thankful you even had a job in the first place. 

I wish we would be more honest with ourselves. How many of us are masking our true feelings to confirm to societal expectations of constant positivity?

I don't know about you—but I can't trick my face into a smile. I’ve done it before, but it’s hilarious to watch and easy to spot. My face and I both know when I'm insincere and won't accept a half-arsed act as credible evidence. If I’m in the gutter and I reach for the facade, my mind is right there laughing, asking: “Are you going to continue this charade? When has suppression ever worked for us?”

This past Christmas season, much like the previous one, I didn’t feel festive. My sabbatical is over, and I'm looking to make a full-time income again doing things I enjoy. Right now, that means building my technical storytelling business—Circle Back Copy. I help startups write technical stuff (eng blogs, thought leadership, marketing copy) in a style that's fun to read. There's a thrill in finding a potential sweet spot of my creative and technical skills. But realism drizzles the idea that this too might be a mirage in the desert.

My career so far has had several chapters. I moved to the Bay Area for the biotech boom in 2016, then skedaddled into software engineering, before this latest shimmy into storytelling. I'm glad I've been able to reinvent myself so many times, but when you're in the desert, you have to be wary that the shiny thing in the distance is not an oasis, but your mind playing tricks on you. 

My messy middle is riddled with incomplete drafts scattered across my desk, unconfirmed hunches tapping on my shoulder, watercolor paint splashing outside the contour lines, and scribbles that may not lead anywhere. It is an emotional rollercoaster that reaches higher peaks and lower troughs than my former corporate life. 

When I made my first $1000 online, it felt better than a $10k bonus at work. The latter was something I almost expected. In fact, I had mentally banked the money before I got it. The feeling was nice but the glow whizzed past and didn’t wave goodbye. 

But contrast that with the the money I made independently. Like huuh—I sat down and created something valuable enough that STRANGERS paid for. Not my family or friends but people whose names I didn’t recognize. I had to look down at my hands in disbelief like: “Hmmm, what else can you guys do? What else are you hiding from me?” For better or worse, I became infected with the belief (and perhaps delusion) that I can pursue an unconventional path. 

My magazine has made around $700 in sales so far. On the surface, that seems like a tiny victory. Especially if you’re on solopreneur twitter where everyone is apparently making $10k MRR. But how often do we, as adults really step out of our comfort zones? How much would you pay a coach to see yourself in a new light? If you’ve always refrained from doing creative things because you’re “not the creative type", what would you give to unwind that limiting belief?

That’s what the magazine was for me. It was a summer-long affirmation that knocked my head with the message: “You’re creative, fam” until I believed it. That’s a revelation that many never receive before they die. It’s like growing a third ear in adulthood. One that can hear a new range of frequencies and sounds that were previously hidden from me.

I had other wins last year too. My essay "How to Design a Sabbatical" is routinely cited online and apparently lives on the reading list for The Commons SF. Strangers have recognized my name and work in public, and quoted my essays to my face—a feeling that's humbling and validating and proof that my writing resonates. I travelled a ton, built a now-defunct AI app for writers, and made a few grand doing freelance writing gigs. 

But do these wins mean my middle is less messy? Nope.

There are moments of sadness and disapppointment too. Periods when I’ve thrown things at the wall, and not only did nothing stick, but the wall seemed to duck and run in the other direction😅. Moments when the resolution in my picture is pixelated—I can only see the next two or three steps and someone is asking me about my long term goals and I….

Moments when I see the salaried and sense the stability in their smiles. Or when I see coasters—let's not pretend like people aren't still coasting despite tech layoffs—and I think—damn must be nice to have steady, reliable income. 

But this whiplash is expected in the messy middle. Anticipate moments of elation interspersed with sinking agony. Moments when you feel lost, and then later, deep conviction pulsates through your veins. Days when you’re living off a cloud because your clients and your creativity colluded to put coins in your wallet and fulfillment in your heart. Times when you’re itching at the edge of your seat with your shoulders hunched over and chest compressed waiting for that crucial email response…that never comes. 

My advice for others in the messy middle: feel the feels man. It hurts. It glistens. It is often unfair and unkind. It might still be worth it. There is no glamour in forcing a smile. 

Imagine yourself standing at a wall armed with two paintbrushes in your hand—one dipped in black, the other in white. With each new experiment, you grab a little paint from each canister and form a new grey. With a lot of luck, you might find a grey you like. The hue that's distinctively yours. One that complements your skin tone and harmonizes your glow. 

But like, there are lots of greys in nature….there's a limitless spectrum of possibilites. Much more greys exist than our eyes can perceive. So that's a lot of mixing and painting and stepping back to look at the wall in front of you. 

Here's where I'm supposed to offer some encouraging conclusion. Something that comforts others in the messy middle telling them that everything will be ok. But the most honest thing is to resist that urge. The story doesn't conclude with a perfect grey—in fact, no such thing exists. The story is one of ongoing unraveling, rewriting, and uncomfortable growth. 

Sometimes, you're in the messy middle. And it is messy. C'est fini.

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In case you missed it:

Ten days ago, I posted an essay that’s been read by several thousands. Check it out 🙏🏾

Writing, what are you doing here?