Caring for my infant son has started to get me thinking about what's next in my career. This October will mark my eighth year at Groupon. And as much as friends and family hear me make snarky jokes about the ol' coupon factory, it really has been good to me.
After years of being the lone "web guy" at various small companies, Groupon took a chance on me as a UI engineer. I started out working on a redesign project which took a long time to go nowhere. The mere mention of its codename for many years triggered PTSD in all those involved.
Just when I was contemplating leaving Groupon after only a few months, an opportunity came up to work on the Internal Tools team, supporting two designers and a half dozen engineering teams. It was there I developed our first CSS framework, Toolstrap, which led to a bunch of similar frameworks for consumer and merchant products.
Along the way, I preached the benefits of responsive design, prototyping, performance, user testing and SVG icons, among other things. Some were met more receptively than others.
The thing I always tell new people about Groupon is that it's a place where you can find something you're interested in and make that your thing, and they'll let you run with it. It's a place where you can make your job what you want it to be and not just what was in the job description of what you were hired for.
I've been fortunate to have two of the best managers I've ever had in my entire career at Groupon. Tyler was the first manager I ever had that talked to me about my career beyond Groupon. He suggested all sorts of things that I could do next but I shot them down, saying "I'm just not that ambitious."
Tyler responded, "but your work is ambitious."
That really stuck with me. Tyler taught me to value my own work and constantly went to bat for me to get me compensated fairly for the value I was providing.
My current manager, Matt, really gets me. He knows and appreciates what I bring to the table, even when others don't. When I get frustrated (which is fairly regularly), he's great at helping me articulate why I'm frustrated and helps talk me down from the ledge. We share a similar dark sense of humor and tend to see eye to eye on the things we work on together.
I've also been lucky to have several awesome colleagues as mentors. They really helped me navigate the politics of working at a large company and encouraged me to think beyond my team or the current project I was working on and consider how I could influence the company at a higher level.
The people are what's kept me at Groupon for so long. I've met so many great and talented people there. So generous with their time and knowledge and their continual support for my annual Extra Life marathons. We've shared a lot of laughs at work, outside of work, and at our yearly offsites.
Sounds great! Why would you leave?
I'm not looking to leave Groupon but having just turned 44(!), I'm wondering if I want to be making websites for the rest of my life. I look at all of the other career paths I might have taken and realize that it might be a little to late in the game to change careers at this point.
I've reached a point where I'm making a comfortable living doing something that I'm good at and the thought of starting a new thing at the bottom is terrifying.
Video Games I originally went to school with the intention of making video games for a living. Taking Discrete Mathematical Structures at U of I quickly dissuaded me of that idea.
I'd still love to work on a video game but reading constant articles about the insane amount of hours it demands and the "culture of crunch" associated with the biggest publishers in the industry is a huge turn-off.
Basketball Vince Carter is still going strong in his 21st NBA season but he's still three years younger than me and is way better at basketball, so I think my chances at a pro career are pretty slim.
After giving up on computer science, I wondered what I could major in that involved no math whatsoever, and sports journalism was the answer. Hey, I thought, I could get paid to watch and write about basketball!
Since then, sports journalism has seen a huge shift from traditional media outlets to bloggers and podcasters becoming mainstream NBA personalities. As much as I used to love writing about hoops, I look at the stuff they're doing over at The Ringer and wonder how I ever did it at all.
Comedy Long before I wanted to make video games, I loved to make people laugh. It was always a dream of mine to be on SNL. As I'd later learn, the road there is difficult and requires so much work and a fair amount of luck.
A lot of SNL people come from Second City, but they don't just pluck you out of the writing or conservatory programs and offer you a spot on the show. You have to get to the main stage just to get noticed, and to do that, you have to get onto the traveling company or go do improv on a cruise ship for a year to even stand a chance at that.
I've got two kids and a mortgage. My wife is not going to let me go Zip Zap Zop on a boat. Are you kidding me?
Movies I've always loved movies and look for every opportunity to make a dumb video using skills I acquired in journalism school and from general messing around behind a camera.
Film is such a cool medium to work in that has room for so many kinds of creativity from acting to cinematography to set design to music. I'd love to really do anything even tangentially related to film, but I have no idea where I'd start.
Peruvian Food After working in the restaurant industry for four years, I thought it would be cool to one day open my own restaurant. Specifically one that serves Peruvian food.
There used to be a handful of Peruvian restaurants in the Chicago area, but in recent years its popularity has exploded, and now there's at least two handfuls of Peruvian restaurants in Chicago.
Opening a restaurant seems like the riskiest proposition of all of these. Restaurants come and go so quickly, and require a ton of hours of work. Besides that, I can't cook for shit.
Sounds like a bunch of excuses to me
Yes, you're absolutely right, voice in my head. A lot of these different things appeal to me but it's highly unlikely I'll make such a drastic career change anytime soon. Things are good right now. I'm comfortable where I'm at. Sure, I'm not curing cancer with internet coupons, but it pays the bills.
I don't know where I'm going with this (which you've probably noticed is a recurring theme around here) but it feels good just to write all this out.
There are lots of things we could be doing or should be doing. Most of the time we're doing exactly what we need to be doing until we find that next thing or until the next thing finds us.