There and Back Again

People like to pretend that work is just work. Like everything just turns off at five. But it doesn’t. It all bleeds together whether you like it or not. With the amount of time we spend together working, we’re bound to search for meaning in what we do. And along the way, you and the people around you are going to do some very human things, have some very human interactions, and make some relationships that might end up being a bit bigger than the place you work at.
With the amount of time we spend together working, we’re bound to search for meaning in what we do.
I remember one of my first design jobs. It was a small two-man shop where we cranked out website after website. I was in my twenties, really just a kid, and my boss became my first real mentor. He gave me space to explore what I enjoyed, and in return, I did everything I could to help us succeed.
Over time we grew a friendship. We talked about my band and family life. He let me take time off to tour across the country, even though I was one of the main sources of income for us. He even helped move around money during tight times so I could buy a wedding ring for my wife. What we built together didn’t just pay the bills. It helped me find my footing in my twenties. It was a time when I was still figuring out who I wanted to be.
When he passed away, I was reminded that the relationships we form through what we do often shape who we are. I still have group chats with old coworkers where we laugh about the chaos, the inside jokes, and the ridiculous things we used to deal with. Some of my closest friends today are people I met at work. And without fail, everyone I’ve bonded with is weirdly special.
The Early Chapters
Before my current gig, I had mostly been a visual designer. I cared about aesthetics, layout, balance, and rhythm. I’d spend hours fine-tuning buttons, adjusting type weights, and making sure the spacing felt right. Back then, my success was measured by how polished something looked, and the people I worked with gravitated toward my strengths in those areas.
Paylocity was my first role where I carried the title User Experience Designer. I came in fairly raw and had high expectations of myself. Even in my interviews, designers asked, “Do you think you’ll be comfortable not doing as much visual stuff?” and, of course, I earnestly said, “Absolutely. I’m excited to dive into the UX process more fully.”
And I did that for about four years, doing usability testing, user journeys, interaction design, prototyping, wireframing, and everything in between.
As I started to grow and mature, I found myself pulled toward design leadership. It felt like the logical next step. It fit my personality, being intentional, people focused, organized, and caring.
Learning to Lead
When I first stepped into management, I had a fair amount of concerns I wrote down. I worried about losing my passion for design and getting stuck in the business side of things. I worried that leading wouldn’t feel as meaningful as creating. I worried that I’d have to always ‘put on a face’, that I’d burn out, or that I’d stop recognizing myself. I worried about saying the wrong things, about not having the right answers. And I worried that once I crossed the line into management, there would be no going back.
Some of those fears were valid, but most weren’t. The truth is, leadership has given me a clearer view of who I am, not just as a designer, but as a person. It actually ended up testing me in ways that craft never could.
“Leadership gave me a clearer view of who I am, not just as a designer but as a person.”
I won’t go into too much depth about my experiences in leadership since I’ve written plenty about them before. What I will say is that leading inside a large organization comes with tradeoffs. As a design leader, you often have to represent a voice, message, or culture that’s bigger than you, and one that you don’t always have full control over. That isn’t necessarily a bad thing, but it is where that feeling of putting on a mask becomes a little more real.
At a smaller company, it can feel like being in a canoe. You and your team can plan, pivot, and steer quickly. But in a larger boat, you’re part of something massive, and the direction of that ship isn’t always yours to set. The culture driven by the business ultimately determines how you can lead and how much freedom you have to shape things.
Even so, I had plenty of agency and tried to make sure my team always had a place that felt steady. If nothing else, I wanted to be a shelter, a carved out space where they could focus on good work, be themselves, and feel protected from some of the noise around them.

Getting back to Craft
Now, after four years of leading design teams and over 7 years at Paylocity, I’m heading back to an individual contributor role at a new company. For me, going back to IC isn’t about escaping management. It’s about returning to what first made me fall in love with design.
I’ve always loved pushing pixels, refining small details, and finding the balance between form and function. I like the quiet focus that comes with building something tangible. It’s the part of the work that first made me feel at home, and somewhere along the way, I missed that feeling.
Stepping away from management doesn’t mean I was tired of it, didn’t like it or wasn’t good at it. It just means I wanted to reconnect with the part of my craft that feels most natural. Leadership helped me understand people. Craft helps me understand myself.
Ironically, even to this day, my old coworkers still think of me as the ‘detail guy’, the one who can make something feel right. Somewhere over the years, that version of me faded into the background while I tried to carry everything else. This next chapter is about getting that part back.
Being an IC again probably isn’t forever, but it feels right for now. After so much time at same company, it’s healthy to solve new problems, work in new systems, and rebuild new muscles. It’s a chance to return to the creative side of what I do best, with a little more perspective and a lot more patience.
Parting thoughts
Looking back, I realize every version of me… the young designer, the overthinking manager, the one rediscovering his craft, has been chasing the same thing: a sense of purpose, a connection to others, and a feeling that what I make matters, even in small ways.
I’m deeply grateful for the people who’ve shared in these past weeks that I made a positive impact in their careers. I’m even more grateful for the friends who stood beside me through the trenches and the high points. My goal as a leader was always simple: to be the kind of manager people remembered as someone who protected, listened, and genuinely cared. My goal as a coworker was to treat my friends with care, and to bring a little humor to their days whenever I could. That’s what I’ll carry with me into whatever comes next.
While I’m in the process of saying goodbye to a lot of folks, I’m once again realizing how lucky I’ve been to cross paths with so many good people. The kind who make work feel a little less like work.
