Stay Soft

I wrote this as my farewell in Slack, and wanted to keep it, so it’s turning into a blog post!

Tomorrow is my last working day at Gusto, which has meant a lot of good-bye conversations, some tears, and a good bit of advice. It’s bittersweet leaving a company full of kind people, but the thing that’s come up in pretty much every conversation is some advice that just keeps coming up… enough that I figured it’d just share it with everyone.

One of the reasons I’m leaving is that my 30th anniversary of working in tech happened in May and hit me a lot harder than I expected. It triggered a lot of feelings, and a lot of introspection. Thirty years is a long time. I’ve learned a lot of lessons the hard way, learned some the easy way (from watching other people learn them the hard way), and have developed my own rules for working that I think can all be summed up with two words (don’t worry, I’ll explain them):

Stay Soft

Working in tech can make you bitter, fragile and angry. For a long time, I was really angry at all of the various disappointments, bad choices by others that affected me, and the failures that left scars. It took a lot of work to process it and turn those traumas into memories. I wish I’d done the work earlier, but I’m glad I did it at all. That’s where softness comes in.

My friend Cindy Li used to remind me: “work won’t love you back.” It’s true. Work won’t love you back; but, people will. And I think that’s the secret to making it to thirty years without being the human equivalent of a charcoal briquette: focus on the people. Focus on the how I show up and who I show up for, not the what. The what changes. The what is frequently outside of our control. Early in my career, I was all about the what. I wanted to work on the biggest, the coolest, the hardest, and get all the glory for doing things that others didn’t think could be done. It was so bad that at one point, my manager pulled me aside and said, “Kevin, people don’t like working with you. Yes, you’re great at your job, but you’re not fun to be around. You’re sarcastic, and it’s not productive.” That hurt, and made me rethink how I worked.

What we do is a team sport. It takes everyone to build something great. Sometimes, even if you’re working with the best people and do almost everything right, the thing won’t be successful. Maybe it was too early, or too late, or didn’t resonate with the audience. Maybe it was just the wrong thing to build. Tying your self-worth to the result of a project is a recipe for misery. Being a developer isn’t a golden ticket to success. We’re not the most important part of the process; we are just a part in the process.

Back to softness. Instead of investing in what, I invested in who and how. I stopped competing with other people and focused on competing only with Past Me. Just that one change fixed all kinds of problems. The second part was to do my best to play the part that wasn’t being played on the teams I was on, trying to make it easier on everyone else involved. That meant learning what mattered to them, their lexicon, and asking them what I could do to make their goals easier to achieve. Being soft means being pliable, willing to jump in and do the work that no one sees, but that needs to be done. It means being willing to absorb disappointments, changes and consequences without taking it personally (but learning from all of it). It means meeting people where they are, accepting their skills gratefully and helping them learn new ones. It means bending to try new ways of working and accommodating your team’s quirks and personalities.

Story time!

My dad was in the Air Force, and a navigator in fighters, so we moved a lot when I was a kid. I moved twelve times before I turned 21. I was also raised Mormon (but, never lived in Utah other than one very painful year at BYU), which meant that in pretty much every school I was in, I was the only Mormon kid in my class. When we lived in the South, that was a big deal. I got picked on a lot, and excluded from things for something I didn’t choose. That all left scars.

So, I know what it means to be alone, excluded and dismissed for something I couldn’t control.

I started my career in tech totally by accident. I got a job at AOL in tech support because my girlfriend at the time worked there and said I should apply. I loved it. As a sheltered 20 year-old Mormon kid (I was so naive), the motley collection of freaks and weirdos was a gold mine of things to learn. I built a group of friends that would have stuck out like a sore thumb at church. I felt at home and accepted for the first time in my life, and it lit a fire. It made me realize that I could make sure that no one I met would ever feel like I did as a kid. I didn’t have a name for it then, other than it feeling like the right thing to do – and I can guarantee I didn’t succeed all the time (I had a lot of work to do – this was thirty years ago).

There’s power in making people feel welcome and cared for. You go from being a bunch of people to a pirate gang. There’s real power in believing in their potential and telling them. Then, you all become unstoppable and can go do ridiculous things; and, have fun doing them.

I’ve definitely gotten better at it over the years, and still get it wrong. But, that’s softness too, and something I see all the time at Gusto – please don’t lose it. It’s the most welcoming place I’ve ever worked, and hopefully, I’ve helped reinforce that. If I haven’t, I’m sorry and I hope you’ll forgive me.

In closing… stay soft. Love the people you work with. Be there for each other. Help each other get better, and tell people you believe in them. Don’t let the indignities and failures make you bitter. Learn from them and use them to do better next time.

I’ll miss you all. It’s been an amazing four years, but it’s time for me to go figure out what I want to be when I grow up.