Drafting More Than Players: Building Community That Lasts
In 2019, we were just coworkers who occasionally went out for karaoke and bonded over Seattle sports. And if you know anything about Seattle, we take our Tech and our Sports seriously. Long story short, we started a fantasy football league.
At the time, it felt like a fun side quest — a little competition, a little trash talk, something to break up the grind and give us a reason to consistently hit Happy Hour Thursdays for Thursday Night Football.
It was my first time participating in any sort of Fantasy Football and I, personally, became invested. Like now I pay for Red Zone every fall invested. Like I can name players not on the Seahawks, and not named Travis Kelce, Tom Brady, or Josh Allen invested. I thrived on the playful smack talk and openness of sharing insights.
And yes, our commissioner named the league “Signing Bonus” because he was so confident he’d win.
He did — then bought himself a custom championship ring.And yes, he held a full ring ceremony. (The audacity.)
A year later, I got my own.
Yes, I won the league in year two.
Yes, I was awarded a custom championship ring.
And yes, we held another ceremony.
Fast forward six years: none of us work together anymore. We don’t even all live in the same city anymore. But every fall? The league comes back to life. The Slack workspace lights up. The trash talk hits harder than a blitz on 3rd down. Sometimes, people even fly/drive back to Seattle just for the draft party. And somehow, this silly little league outlasted org charts, pandemics, and cross-country moves.
And tonight, we’re drafting again. Same league, same chaos, different Zoom links. By the time this post goes live, we’ll be scattered across states and time zones, but still heckling each other over draft picks like nothing has changed.
So outside of the fact that the new NFL season officially kicks off this week, why am I sharing that I play fantasy football with former colleagues?
Because genuine, opt-in activities are where community thrives. It’s the magic of real connection at work: it sticks. Not because someone wrote it into a culture deck, or because there was free pizza at the happy hour. It sticks because it’s authentic. Because people actually chose to show up.
This league brought me together with people I adore deeply. People I might never have known beyond “passing in the breakroom” if our conversations had stayed strictly about work. It helped me survive and thrive during the pandemic too — when we expanded into Fantasy Hockey and threw regular Zoom parties to play Among Us and catch up.
As Ron Swanson would say, sometimes people are just “workplace proximity associates.” And that’s fine. Not every coworker is meant to be a lifelong friend. You can’t force it with icebreakers or HR initiatives. In fact, the more artificial the environment, the more uncomfortable it gets.
But you can create the conditions for it: space, flexibility, and permission to connect beyond the day-to-day grind. Sometimes it looks like dedicated Slack channels (#swifties, #booknerds, #corgi-fan-club). Sometimes it looks like a lunch walk or a “work-free” coffee chat on Zoom. And sometimes, apparently, it looks like a fantasy football league that refuses to die.
Workplaces love to talk about “culture,” but the best proof of culture is what survives outside the office walls. If you leave a job and never hear from your coworkers again, that tells you something. If you leave and six years later you’re still smack-talking their roster management skills? That tells you something, too.
The NFL season kicks off this week, but for me the real win is this: a league born in a breakroom in 2019 is still going strong in 2025. Different jobs, different cities, same league, same friends, same trash talk.
That’s a community worth drafting for.
As always, caffeinated, chaotic, & curious
- Mads