personal

On Dropouts and Bootstraps

mipsytipsy, 6 Comments

In my early twenties I had a cohort of friends and coworkers, all Silicon Valley engineers, all quite good at their jobs, all college dropouts. We developed a shared conviction that only losers got computer science degrees. This sounds like a joke, or a self-defense mechanism, but it was neither. We were serious.

We held CS grads in contempt, as a class. We privately mocked them. When interviewing candidates, we considered it a knock against someone if they graduated — not an insuperable one by any means, but certainly a yellow flag, something to be probed in the interview process, to ensure they had good judgment and were capable of learning independently and getting shit done, despite all evidence to the contrary.

We didn’t look down on ALL college graduates (that would be unreasonable). If you went to school to study something like civil engineering, or philosophy, or Russian literature, good for you! But computers? Everything in my experience led me to conclude that sitting in a classroom studying computers was a waste of time and money.

I had evidence! I worked my way through school — as the university sysadmin, at a local startup — and I had always learned soooo much more from my work than my classes. The languages and technologies they taught us were consistently years out of date. Classes were slow and plodding. Our professors lectured on and on about “IN-dustry” in a way that made it abundantly clear that they had no recent, relevant experience.

College dropouts: the original bootstrappers

The difference became especially stark after I spent a year working in Silicon Valley. I then returned to school, fully intending to finish and graduate, but I could not focus; I was bored out of my skull.

How could anyone sit through that amount of garbage? Wouldn’t anyone with an ounce of self-respect and intrinsic motivation have gotten up off their butts and learned what they needed to know much faster on their own? For fuck’s sake! just google it!

My friends and I rolled our eyes at each other and sighed over these so-called software engineers with degrees, who apparently needed their learning doled out in small bites and spoon-fed to them, like a child. Who wanted to work with someone with such a high tolerance for toil and bullshit?

Meanwhile we, the superior creatures, had simply figured out whatever the fuck we needed to learn by reading the source code, reading books and manuals, trying things out. We pulled OUR careers up by our own bootstraps, goddammit. Why couldn’t they? What was WRONG with them??

We knew so many deeply mediocre software engineers who had gotten their bachelor’s degree in computer science, and so many exceptional engineers with arts degrees or no degrees, that it started to feel like a rule or something.

Were they cherrypicked examples? Of course they were. That’s how these things work.

People are really, really good at justifying their status

Ever since then, I’ve met wave after wave of people in this industry who are convinced they know how to sift “good” talent from “bad” via easily detected heuristics. They’re mostly bullshit.

Which is not to say that heuristics are never useful, or that any of us can afford to expend infinite amounts of time sifting through prospects on the off chance that we miss a couple quality candidates. They can be useful, and we cannot.

However, I have retained an abiding skepticism of heuristics that serve to reinforce existing power structures, or ones that just so happen to overlap with the background of the holder of said heuristics.

Those of us who work in tech are fabulously fortunate; in terms of satisfying, remunerative career outcomes, we are easily in the top .0001% of all humans who have ever lived. Maybe this is why so many of us seem to have some deep-seated compulsion to prove that we belong here, no really, people like me deserve to be here.

This calls for some humility

If nothing else, I think it calls for some humility. I don’t feel like I “deserve” to be here. I don’t think any of us do. I think I worked really fucking hard and I got really fucking lucky. Both can be true. Some of the smartest kids I grew up with are now pumping gas or dead. Almost none of the people I grew up with ever reached escape velocity and made it out of our small town.

When I stop to think about it, it scares me how lucky I got. How lucky I am to have grown up when I did, to have entered tech when I did, when the barriers to entry were so low and you really could just learn on the job, if you were willing to work your ass off. I left home when I was 15 to go to college, and put myself through largely on minimum wage jobs. Even five years later, I couldn’t have done that.

There was a window of time in the 2000s when tech was an escalator to the middle class for a whole generation of weirdos, dropouts and liberal arts misfits. That window has been closed for a while now. I understand why the window closed, and why it was inevitable (software isn’t a toy anymore), but it’s still.. bittersweet.

I guess I’m just really grateful to be here.

~charity

Experiment update

As I wrote last week, I’m trying to reset my relationship with writing, by publishing one short blog post per week: under 1000 words, minimal editing. And there marks week 2, 942 words.

See you next week.

Week 1 — “On Writing, Social Media, and Finding the Line of Embarrassment”

 

 

 

On Dropouts and Bootstraps

On Writing, Social Media, and Finding the Line of Embarrassment

mipsytipsy, , 16 Comments

Brace yourself, because I’m about to utter a sequence of words I never thought I would hear myself say:

I really miss posting on Twitter.

I really, really miss it.

It’s funny, because Twitter was never not a trash fire. There was never a time when it felt like we were living through some kind of hallowed golden age of Twitter. I always felt a little embarrassed about the amount of time I spent posting.

Or maybe you only ever really see golden ages in hindsight.

I joined Twitter in 2009, and was an intermittent user for years. But it was after we started working on Honeycomb that Twitter became a lifeline, a job, a huge part of my everyday life.

Without Twitter, there would be no Honeycomb

Every day I would leave the house, look down at my phone, and start pecking out tweets as I walked to work. I turned out these mammoth threads about instrumentation, cardinality, storage engines, etc. Whatever was on my mind that day, it fed into Twitter.

In retrospect, I now realize that I was doing things like “outbounding” and “product marketing” and “category creation”, but at the time it felt more like oxygen.

Working out complex technical concepts in public, in real time, seeing what resonated, batting ideas back and forth with so many other smart, interesting people online…it was heady shit.

In the early days, we actually thought that Honeycomb-style observability (high cardinality, slice-and-dice, explorability, etc) was something only super large, multi-tenant platforms would ever care about or be willing to pay for. It was the conversations we were having on Twitter, the intensity of people’s reactions, that made us realize that no, actually; this was fast becoming an everybody problem.

Twitter was my most reliable source of dopamine

It’s impossible to talk about Twitter’s impact on my life and career without also acknowledging the ways I used it to self-medicate.

My ADHD was unmanaged, unmedicated, and unknown to me in those years. In retrospect, I can see that my only tool as an engineer was hyperfocus, and I rode that horse into the ground. When I unexpectedly became CEO, my job splintered into a million little bite sized chunks of time, and hyperfocus was no longer available to me. The tools I did have were Twitter and sleep deprivation.

Lack of sleep, it turns out, can wind me down and help me focus. If I’ve been awake for over 24 hours, I can buckle down and force myself to grind through things like email, expense reports, or writing marketing copy. Sleep deprivation is not pleasant, it’s actually really fucking painful, but it works. So I did it. From 2016 to 2020, I slept only once every two or three days. (People always think I am exaggerating when I say this, but people closer to me know that this is probably an understatement.)

But Twitter, you dear, dysfunctional hellsite… Twitter could wind me up.

I would go for a walk, pound out a fifty-tweet thread, and arrive at my destination feeling all revved up.

I picked fights, I argued. I was combative and aggressive in public, and I loved it. I regret some of it now; I burned some good relationships, and I burned out my adrenal glands. But I would sit down at my desk feeling high on dopamine, and I could channel that high into focus. It’s the only way I got shit done.

I got my ADHD diagnosis in 2020 (thank the gods). Since then I’ve done medication, coaching, therapy in several modalities, cats… I’ve tried it all, and a lot of it has helped. I sleep every single night now.

That world is gone, and it’s not coming back

The social media landscape has fragmented, and maybe that’s a good thing. There is nothing today that scratches the same itch for me as Twitter did, in its golden years. And maybe I don’t need it in quite the same way as I used to.

Most of the people I used to love talking with on X seem to have abandoned it to the fascists. LinkedIn is performatively corporate and has no soul. I’m still on Bluesky, but it’s a bit of an echo chamber and people mostly talk about politics; that is not what I go to social media for. The noisy, combative tech scene I loved doesn’t really seem to exist anymore.

These days I use social media less than ever, but I am learning that my writing is more important to me than ever. Which is forcing me to reckon with the fact that my writing process may no longer fit or serve the function I need it to.

Most of those epic threads I put so much time and energy into crafting have vanished into the ether. The few that I bothered to convert into essay format are the only ones that have endured.

I’ve been writing in public for ten years now

Do you ever hear yourself say something, causing you to pause, surprised: “I guess that’s a thing I believe”?

A couple months ago, Cynthia Dunlop asked me to share any thoughts I might have on my writing, as part of the promotional tour for “Writing for Developers: Blogs That Get Read” (p.s., great book!). I wrote back:

There are very few things in life that I am prouder of than the body of writing I have developed over the past 10 years.

When I look back over things I have written, I feel like I can see myself growing up, my mental health improving, I’m getting better at taking the long view, being more empathetic, being less reactive… I’ve never graduated from anything in my life, so to me, my writing kind of externalizes the progress I’ve made as a human being. It’s meaningful to me.

Huh. Turns out that’s a thing I believe. 🤔

I wrote my first post on this site in December of 2015. It’s crazy to look back on all the different things I have written about here over the past ten years — book reviews, boba recipes, technology, management, startup life, and more.

Even more mindblowing is when I look at my drafts folder, my notes folders. The hundreds of ideas or pieces I wanted to write about, or started writing about, but never found the time to polish or finish. Whuf.

I need to learn how to write shorter, faster pieces, without the buffer of social media

From 2015 to somewhere in the 2021-2023 timeframe, thoughts and snippets of writing were pouring out of me every day, mostly feeding the Twitter firehose. Only a few of those thoughts ever graduated into blog post form, but those few are the ones that have endured and had the most impact.

Over the past 2-4 years, I’ve been writing less frequently, less consistently, and mostly in blog post form. My posts, meanwhile, have gotten longer and longer. I keep shipping these 5000-9000-word monstrosities (I’m so sorry 🤦). I sometimes wonder who, if anyone, ever reads the whole thing.

The problem is that I keep writing myself into a ditch. I pick up a topic, and start writing, and somehow it metastasizes. It expands to consume all available time and space (and then some). By the time I’ve finished editing it down, weeks if not months have passed, and I have usually grown to loathe the sight of it.

For most of my adult life, I’ve relied on hard deadlines and panic to drive projects to completion, or to determine the scope of a piece. I’ve relied on anger and adrenaline rushes to fuel my creative juices, and due dates and external pressure to get myself over the finish line.

And what does that finish line look like? Running out of time, of course! I know I’m done because I have run out of time to work on it. No wonder scoping is such a problem for me.

A three month experiment in writing bite sized pieces

I need to learn to write in a different way. I need to learn to draft without twitter, scope without deadlines. Over the next five years, I want to get a larger percentage of my thoughts shipped in written form, and I don’t want them to evaporate into the ether of social media. This means I need to make some changes.

  1. write shorter pieces
  2. spend less time writing and editing
  3. find the line of embarrassment, and hug it.

For the next three months, I am going to challenge myself to write one blog post per week (travel weeks exempt). I will try to cap each one under 1000 words (but not obsess over it, because the point is to edit less).

I’m writing this down as a public commitment and accountability mechanism.

So there we go, 1473 words. Just above the line of embarrassment.

See you here next week.

On Writing, Social Media, and Finding the Line of Embarrassment

On pain, careers, and doing things the hard way.

mipsytipsy, , , 2 Comments

Part 1

Seven years ago I was working on backend infra for mobile apps at Parse, resenting MongoDB and its accursed single write lock per replica with all my dirty, blackened soul.  That’s when Miles Ward asked me to give a customer testimonial for MongoDB at AWS reinvent.

It was my first time EVER speaking in public, and I had never been more terrified.  I have always been a writer, not a talker, and I was pathologically afraid of speaking in public, or even having groups of people look at me.  I scripted every word, memorized my lines, even printed it all out just in case my laptop didn’t work.  I had nightmares every night.  For three months I woke up every night in a cold sweat, shaking.

And I bombed, completely and utterly.  The laptop DIDN’T work, my limbs and tongue froze, I was shaking so badly I could hardly read my printout, and after I rushed through the last sentences I turned and stumbled robotically off the stage, fully unaware that people were raising their hands and asking questions.  I even tripped over the microphone cord in my haste to escape the stage.

Afterwards I burned with unpleasantries — fear, anger, humiliation, rage at being so bad at anything.  It was excruciating.  For the next two years I sought out every opportunity I could get to talk at a meetup, conference, anything.  I got a prescription for propranolol to help manage the physical symptoms of panic.   I gave 17 more talks that year, spending most nights and weekends working on them or rehearsing, and 21 the year after that.  I hated every second of it.

I hated it, but I burned up my fear and aversion as fuel.  Until around 18 months later, when I realized that I no longer had nightmares and had forgotten to pack my meds for a conference.  I brute forced my way through to the other side, and public speaking became just an ordinary skill or a tool like any other.

part 2

I was on a podcast last week where the topic was career journeys.  They asked me what piece of career advice I would like to give to people.  I promptly said that following your bliss is nice, but I think it’s important to learn to lean into pain.

“Pain is nature’s teacher,” I said.  Feedback loops train us every day, mostly unconsciously.  We feel aversion for pain, and we enjoy dopamine hits, and out of those and other brain chemicals our habits are made.  All it takes is a little tolerance for discomfort and a some conscious tweaking of those feedback loops, and you can train yourself to achieve big things without even really trying.

But then I hesitated.  Yes, leaning in to pain has done well for me in my career.  But that is not the whole story, it leaves off some important truths.  It has also hurt me and held me back.

Misery is not a virtue.  Pain is awful.  That’s why it’s so powerful and primal.  It’s a pre-conscious mechanism, an acute response that kicks in long before your conscious mind.  Even just the suggestion of pain (or memory of past trauma) will train you to twist and contort around to avoid it.

When you are in pain, your horizons shrink.  Your vision narrows, you curl inward. You have to expend enormous amounts of energy just moving forward through the day inch by inch.

Everything is hard when you’re in pain.  Your creative brain shuts down.  Basic life functions become impossible tests.  You have to spend so much time compensating for your reduced capacity that learning new things is nearly impossible.  You can’t pick up on subtle signals when your nerves are screaming in agony.  And you grow numb over time, as they die off from sheer exhaustion.

part 3

I am no longer the CEO of honeycomb.

I never wanted to be CEO; I always fiercely wanted a technical role.  But it was a matter of company survival, and I did my best.  I wasn’t a great CEO, although we did pretty well at the things I am good at or care about.  But I couldn’t expand past them.

I hated every second of it.  I cried every single day for the first year and a half.  I tried to will myself into loving a role I couldn’t stand, tried to brute force my way to success like I always do.  It didn’t get better.  My ability to be present and curious and expansive withered.  I got numb.

Turns out not every problem can be powered through on a high pain tolerance.  The collateral damage starts to rack up.  Sometimes the only way to succeed is to redefine success.

Pain is a terrific teacher, but pain is an acute response.  Chronic pain will hijack your reward pathways, your perspective, your relationships, and every other productive system and leave them stunted.

Leaning in to pain can be powerful if you have the agency and ability to change it, or practice it to mastery, or even just adapt your own emotional responses to it.  If you don’t or you can’t, leaning in to pain will kill you.  Having the wisdom to know the difference is everything.  Or so I’m learning.

From here on out I’ll be in the CTO seat.  I don’t know what that even means yet, but I guess we’ll find out.  Stay tuned.  <3

charity

img_7678

On pain, careers, and doing things the hard way.