Five years ago I started my dream job.

For as long as I can remember I’ve wanted to do something that matters. I said this to my parents as a teenager working at the local grocery store. They assured me my time would come. It was a hard pill to swallow; working nights and weekends stocking shelves for minimum wage, getting called out by my bosses’ boss for skipping a shift to go to a concert (oops), quitting to go wash dishes to pay for university. Working through (most) of university in a kitchen pulling what I dubbed “8-day weeks” (5 days of university + three 8-hour shifts in a week). Working something like over 100 days in a row without a day off between work and school.

My time would come. This would all be worth it when I graduated and could do something that mattered.

Right out of the gates I fell flat on my face. I had a job lined up with a start date of ~2 months after I graduated. I had circulated resumes at a job fair, done an on-site, and received a job offer to be a Software Developer (Note: this was a verbal offer - I hadn’t signed anything). I was over the moon. I was going to have a real job. My girlfriend and I moved to a new city together a couple weeks before the start date. I started emailing the recruiter about details - when should I show up, dress code, should I bring anything?

She was on vacation, and I got the automated response. “Whatever”, I thought to myself, “I’ll talk to them when they get back”. A week before my supposed start date, with a new apartment to pay for, bills, student debt, and zero savings, they told me they would not be pursuing my employment. My final grade average was too low.

Shit.

Over the next month I sent out hundreds of applications to anyone employing new grads in a hundred-mile radius. I was fortunate that it only took me about a month to find someone else willing to take a chance on me. It was at a Salesforce-like Customer Relationship Management enterprise software company. The clients were businesses that often produced high-end custom furniture or products for wealthy clients.

The work I was doing didn’t matter.

My now-wife would often console me with the same words my parents said to me almost a decade before: your time will come. This would all be worth it when I proved myself in a business context and then I could do something that mattered.

I worked hard. Took on challenges as they came my way. Spun up a couple side-projects to help the business. Tried pitching in with ideas. Worked with some great people. In the end, I couldn’t keep going. I built features that I would estimate less than ten people used, total. The features people did use helped them pick out different kinds of moulding for their custom cabinets in their kitchen that would end up costing more than half my yearly salary. I needed out.

In May 2017, I found my out: Prodigy Game.

At the time it was a scrappy start-up with about eighty employees, all housed on the second floor of a large office building, working on one thing: the Prodigy Math Game. An MMO for kids to play during school that helped them learn Math. I couldn’t have asked for a better fit: I was a big Math kid in school, I was (and am) an avid gamer, and they needed Software Developers like I needed a Software Development job. I interviewed and on May 29th, 2017, exactly 5 years ago at time of writing, I started my dream job.

I was finally, finally, finally going to do something that mattered.

---

No company is perfect. Real life gets messy. To say these last five years have been nothing but sunshine and rainbows would be a lie. But when I think about my time at Prodigy, I don’t think about the bad parts. Sure, there have been lay-offs. Products have been sunset. People have come and gone. Production has gone down.

That’s not Prodigy to me.

When I started, I helped rebuild one of our legacy Teacher reports in our modern stack. I got a lot of great feedback and direction when building out this report. I pair-programmed with our now-VP of Engineering. I got design feedback from our now-VP of Product Design. I got Pull Request feedback from a colleague who would end up standing with me as one of my groomsmen a couple years later. When the report launched, I saw teachers posting on social media about how much they loved the new report. How it gave them great insight into how their students were doing, which could in turn help them curate their lesson plans.

I did something that mattered.

This is what Prodigy is to me. I have built relationships with some of the most startlingly intelligent and driven people I have ever met. I have grown thanks to the guidance of amazing, compassionate, insightful mentors. When I think about my career at Prodigy, I think most about the people I have had the privilege of working with and learning from. I think about my friends, and how, every day, we somehow get to live the dream of building a product that kids love - and helps them learn.

The average tenure at a software company is somewhere between two and three years, depending on your source. Given that statistic, I wanted to reflect on what has kept me around for about double that time. If you’ve been paying attention, you might say: “It’s because you’re finally doing something that matters”. That’s not all. I didn’t know this before, but it’s not solely about doing something meaningful.

It’s being able to wake up every day, and keep doing what matters.

Trying to improve education for every student on the planet is a task that’s never done. It’s easy for it to overwhelm you - to throw your hands up and decide you’re going to open a kombucha shop because it’s easier. To say “to heck with it” and decide ‘the juice isn’t worth the squeeze’ as some say. And this hasn’t been an easy year. I’ve thought about the kombucha path more times in the past 12 months than I ever have. A lot of amazing people have left Prodigy.

And a lot have also stayed.

And more and more keep joining. And the work still matters. I still wake up every day and am given life by the people who have stayed (and even some who have left). Now more than ever, I am choosing to stay at Prodigy. For the people. For the love of learning. For work that matters.

Through my time at Prodigy, I’ve been through something like six office expansions, five hackathons, four different squads, three promotions, two different brands, and one pirate ship.

We’ve had our highs and lows. But we keep moving forward.

It ain’t about how hard you hit. It’s about how hard you can get hit and keep moving forward. That’s how winning is done.

I have been in a losing war with sleep for as long as I can remember.

I’m not an insomniac or anything (thankfully), but I also wouldn’t classify myself as someone who sleeps well. My partner and other close family members can fall asleep at the drop of a hat (sometimes even unintentionally!) To them, sleep seems to come to them as naturally as breathing.

Not so for me. I’ve had black-out curtains. I’ve worn sleep masks. I’ve taken melatonin many times. I’ve made major lifestyle adjustments to assist my sleep. For instance, I stop looking at any screen 60-90 minutes before I attempt to fall asleep. I don’t play any video games past 9pm. I set up blue light filtering (like f.lux) on most of my devices. I have a Fitbit to track my sleep patterns.

In spite of all this, sleep and I still have an inconsistent relationship. There are days, even weeks where I believe I fall asleep reasonably fast (let’s say within 15-30 minutes). But then my old foe sleep rallies, and I have nights where I’m staring at the back of my eyelids for what feels like the whole night.

A couple months ago, I heard something curious about sleep (though for the life of me I can’t find the source). As I recall, the speaker was positing the idea that humans are not built to sleep “through the night”. We’re built more for “shift sleep”, where we sleep for a couple hours while someone else watches for predators before switching off.

I’m going to call sleeping through the night “1x8 sleep” (one session of 8 hours), and shift sleep “2x4 sleep” (two sessions of four hours). I’m a firm believer that we need about 8 hours of sleep a day. I’ve done less, during university. I do not recommend it. However, it hadn’t occurred to me before to attempt to break that 8 hours up over more than one session.

Over the last year or so, I’ve been finding myself awake (and not that groggy half-dream state but wide awake) about 3.5 hours into my night’s sleep. It happened frequently enough that when this speaker made this comment, my subconscious surfaced the possibility of a connection. What if “sleeping through the night” is another one of the post-hoc adaptations to civilized living we’ve made that the biology hasn’t caught up with? “We need about 8 hours of sleep,” we say to ourselves, “may as well get it all over with at once”.

I think it makes sense that our distant ancestors could not afford to be unconscious for long stretches of time, or they would get eaten. The idea of 2x4 sleep makes a lot of sense as an adaption to living in a hostile world (if you’ve played any amount of D&D, 2x4 sleep is probably how your party takes a Long Rest most of the time). I wonder if there’s an evolutionary trait that predicts for 1x8 sleepers versus 2x4 sleepers.

I don’t think I can get away with 2x4 sleep in practice. I think my current life circumstance and schedule does not lend itself well to a ten-to-twelve hour sleep span, with two-to-four of those hours being activity around 3AM. I would be curious if someone has ever tried to operate on a 2x4 schedule, and for how long, and how it affected their health and happiness.

I’ve been ruminating on the nature of time more as the pandemic has begun to wind down. A related notion I brought up to my partner was that I intend to live on Daylight savings time forever. My idea, roughly, is to shift my schedule one hour “back” when we roll the clocks forward in the fall. For instance, I’m working 9-5 these days, but to maintain my schedule, I will shift to 8-4 when the clocks roll back. The intent will be that my days will “feel” the same; just the numbers on the machines will be one less than usual. Whatever.

I recognize that not everyone has the freedom or latitude to explore these schedule modifications for countless reasons. I guess I’m interested in exploring them as a way to “destroy my enemy (sleep) by making it my friend”. I don’t want to be in this constant battle with sleep. I want that peaceful, serene look some people get when they sleep. I’m going to spend a third of my life sleeping, I might as well try to enjoy it.

What if the struggle stems from the fact that I’m “doing it wrong”? Sleep seems like an adversary in the 1x8 model, but maybe we’re not on the same wavelength. It’s trying to keep me from being eaten by predators with the 2x4 model. What if I went along with it? Maybe, if I got up and was active from 3AM to 5AM, sleep and I could become friends.

The cats nestle close to their kittens now. The lambs have laid down with the sheep. You’re cozy and warm in your bed, my dear. Please go the fuck to sleep.

This is a tribute to someone I didn’t know. Our specific relationship isn’t important. They passed away recently, and their life was meaningful to people I care about. Without going in to detail, this tribute may be giving them too much credit. Even so, I think the message is important.

To me, anyway.

---

Gus woke up to a familiar sound: seagulls squawking as the sun rose on a warm summer’s day. The smell of salty Atlantic sea air rolled in through the open window in his bedroom which, combined with the noise of the birds, roused him to consciousness. He pulled back the curtains and looked out over the ocean, breathing the smell in deeply (well, as deeply as he could).

He put himself through his morning routine, assembled a modest breakfast of toast and black coffee, and went to enjoy it out on his balcony. Gus lived on the eighth floor of a medium-sized apartment building, in a small town on the eastern coast of the United States (the specific name of which is not important to our story).

Gus enjoyed watching the maritime traffic from his balcony in the morning, before the day got oppressively hot and he was forced indoors. He saw some dinghies had already put out to the open waters before the sun had even risen, and were mere specks amongst the visual noise of the churning waters. The pleasure boats were all still moored at the docks though - their owners wouldn’t unleash them on to the waters for another couple hours.

As he finished off his toast, Gus lit the first of what would surely be many cigarettes today. He had stopped enjoying smoking years ago, but like his boat-watching, or the smell of the ocean, it was familiar. There was a comfort he took in the certainty of his routine.

Gus’ appearance was unremarkable for someone his age. He was in his late seventies, about 5’8”, somewhat stout, with salt-and-pepper black hair that he kept short, but not too short. He shaved regularly, didn’t need glasses, and dressed modestly, often in a pair of brown or tan slacks and a plain blue shirt of varying hues.

After about an hour or so of enjoying the view from his balcony, the day began to warm to an unpleasant degree, and Gus retreated to the interior of his apartment. As he shut the sliding screen door to the balcony behind him, he turned to head towards his easy chair when his calendar caught his eye. He thought for probably too long about what the date was before coming to the conclusion that tomorrow had a reminder scrawled on it:

“Jennifer - Birthday - 24”.

Like much of his life, he added these reminders to each successive year’s calendar on automatic. He would record birthdays and anniversaries for the last bit of family he had: his son, and his son’s two children, who he surmised were both now in their mid-to-late twenties. Gus hadn’t had regular contact with them for…almost twenty years? He couldn’t even remember why any more.

They weren’t part of the routine.

He stared at the scrawled note on the calendar. He could picture Jennifer clearly in his mind’s eye - as a five-year-old. What was she like now? He wondered if she took after him at all, or his ex-wife. Did she play any sports? What were her hobbies? He thinks he heard about a boyfriend when he last spoke to his son a year or two ago. How was that going?

His eyes watered slightly. He took a couple slow breaths, to steady himself. They weren’t terribly deep, but they helped quell the tide of emotion that had threatened to drag him out to sea. In that moment, he had resolved to himself: he would call her tomorrow. He would ask about her hobbies. He would ask if she would like to see him sometime. She could even bring that boyfriend.

He crossed the room with more purpose in his step than he had had in a while, and settled in to his easy chair. There was a big game today, and as long as the boys played well and those damn rookies didn’t choke like always, they should have it in the bag.

“I swear, if I had a nickel for every rookie that cost this team a title…” He muttered to himself as he scanned around for the remote. He found it, pointing himself back to the TV, and saw the corner of the calendar peeking around the edge of the TV. He smiled. Tomorrow.

…

It was past sundown and Gus was back out on his balcony, the night bringing the world respite from the oppressive heat of the day. He was whistling softly to himself, the last nub of a cigarette glowing between his fingers. He took a slow, final drag, and butted it out in the ashtray resting on a small folding table beside him.

He lifted himself from his chair with slightly more effort than usual, and made his way inside. As he turned to close the screen door behind him, he caught himself on the wall. His head was spinning. Must have gotten up too fast. He tried to steady himself, again taking slow, shallow breaths.

His arm was starting to hurt. A lot. Had holding himself upright really become this difficult? No, this wasn’t exhaustion, this was something else. He got a nervous look in his eyes and began casting around the inside of his apartment for the phone. He needed help. Now.

He saw it a couple feet away on the side table by his chair, turned, let go of the wall, and collapsed on the ground. He reached out with his good arm, but it was no use. It may as well have been on one of those dingies out at sea.

Panic began to overtake him. His one arm screamed in pain, a shooting pain driving up and down it. His chest hurt a lot; he could barely breathe. He was taking short, whimpering breaths, and began curling in to a ball on his apartment floor. He opened his eyes briefly against the pain, and looked up.

“Jennifer - Birthday - 24”.

Tomorrow.

His eyes welled with tears.

…

It was a couple days before anyone had noticed that Gus had been eerily silent, and absent from his usual routine (the parts at least that brought him briefly in contact with other people, like the super of his apartment, or the local grocer). Police had been called, and the worst had been confirmed. The body had already been removed and the apartment cleaned by professionals by the time Jennifer and her parents stopped by.

”…probably going to smell like cigarette smoke in there,” remarked Jennifer’s father as he lead their small troupe through the door. They now had the unhappy task to assess a life they barley knew, and decide what was worth keeping.

As they spread out, the first thing Jennifer was drawn to was the calendar. She saw her birthday marked, almost a week ago to the day. She looked at it quizzically and turned around to address her parents: “Why did he have my birthday on his calendar?”

She began flipping through the months. It wasn’t just hers. “Why did he have everyone’s marked? And your anniversary? Did he ever call you, or write a letter or…something?” Her dad frowned a little, and shook his head.

“I don’t know,” he responded. He looked around at what was technically his father’s apartment, and saw the degrees and professional accolades his father had earned in life. They were faded, and a little smoke-damaged. He couldn’t help but look at them in a detached way, though: they were being assessed for their material value, not their sentimental value.

Jennifer made a small frowning face to herself, and looked back at the calendar.

“I wish he would have called.”

I was told that writing is a great way to force oneself to concretize their ideas.

Writing makes you confine your ideas to words - to language. As the saying goes “ideas are like assholes; everybody’s got one”. Ideas by themself are not special; they become great only when paired with thoughtful execution.

I’m someone who does not have a lot of ideas (I think; it’s hard to compare your thoughts to someone else’s). I grew up believing my sibling got all the creative talent and I got all the “logical” talent. That old “left brain/right brain” model.

But I enjoy writing. I’ve made it my profession to write things (okay those things are code and I’m writing functions but I have a strong belief there is a tremendous overlap in skills). When I’m writing code I’m attempting to convey intent using words and phrases that carry shared meaning in a specific context.

I think when you’re younger, you can often lead yourself to believe that skills that come “naturally” to you are things that everyone is good at, and that the skills that actually matter are the ones that you specifically must apply hard work to be good at (after all, if it’s easy for a child to do, it must be easy for adults to do, and thus cannot be of much value).

I’ll give the example of public speaking. I’m a rather good public speaker, and have been since I was at least 12 or 13 (my parents may be able to attest to even earlier instances that I can’t even remember). Apparently, most people find public speaking hard - some even find it scary. But if you told 13-year-old me that this skill that comes “naturally” to him is one that could be cultivated in to a lucrative career, it would stun him. You don’t even have to contend with another person when speaking publicly! You get to ramble on and on and no one can stop you!

Contrast this with something like painting, or any other visual art. I am an atrocious painter. My mother and sister are excellent painters, and have come to acquire this skill through practice coupled with natural ability. But if you’re not in the top 0.00001% of painters, you’re probably a hobbyist. Even with decades of practice, most people who are good painters (as I understand the field) are not professionally employed as such.

So when I found out I liked writing and it’s something that “felt easy”, I dismissed it as a non-viable career path. You have to work hard at some skill you aren’t good at to make a good living.

In the intervening years between that world view and my current one, I’ve come around. I’ve started writing again. Because I enjoy it, and because it helps force me to turn my ideas in to something real. I want to use this space to sharpen my writing blade, so that I can use it in on the battlefield of professional endeavours.

If you take any time to read anything I have written, drop me a line. I need people to be my whetstone, to show me where the nicks and notches are, and to show me where the blade has already been honed.