Work: A Retrospective

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.