2025 in Reflection
My life is very full. Of the right things? I am not so sure.
Words by
John Maitland
Published on
Nov 28, 2025
I started the year in a pit — a low, uncomfortable place that was hard to identify. I felt fearful for my creativity in the midst of AI’s rapid growth, unsure of the purpose of my role at work, and stuck in a life that feels safe but stagnant. Comfort, I learned, can flatten you. Especially when the world beyond my front door is spinning through its own storms and I’m sitting there feeling vaguely disconnected from my own spark.
In January I sought out mentorship with Meg Lewis through their “Full Time You” program, hoping to find the core of my next act as a creative professional. It felt like dusting off a thin veneer of malaise that had settled in after years of working inside a closed ecosystem, and rediscovering values I’ve actually held close my whole life. I’m not sure I’ve solved my creative puzzle or fully found the force that got me here in the first place, but their support — and the conversations within our group — have been grounding. I feel more poised heading into 2026, with a bit more direction and confidence in the vectors I’m plotting.
From spring to fall, the year picked up speed. I went on spring break with my nieces to the San Juan islands to see orcas in the wild for the first time. I flew to Arizona to unite our Product and Design orgs at Rocket Money (threw in a cheeky bike ride before my flight too), back and forth to DC, and to Detroit for an all company annual reunion and then absconded to Europe for a month and half immediately after.
I lived with my sister in Berlin for the summer, we hiked the Alps of Austria and Switzerland, enjoyed 16 hours of sunlight each day and I immersed myself in her social life. Back in Virginia, I began to train for a marathon I naively signed up for the coming November. I do not recommend that unless you enjoy learning exactly how many ways the human body can complain. All of it happened incredibly fast, but it reminded me what it feels like to be physically in the world again, not just mentally running on autopilot.
This was also the year I spent the most time with my family since I can remember — multiple sibling trips to North Carolina, living with my younger sister who doubled as a European tour guide, coaching soccer, driving to the town that inspired the Twilight franchise with my nieces (they had no idea), a family reunion to announce a new baby coming in 2026, and just the right amount of time with my parents before it becomes too much. It’s enriching and difficult. My family can be a handful. They can also be a refuge. I don’t always know which one I’m driving toward when I get in the car, but I always go anyway. There’s love in that, even when the edges are sharp.
In the summer, among spending more time in airports than my own apartment, I became the Director of the Design team at Rocket Money, and it injected my career with a whole new set of problems to solve — all people and relationship-oriented (hint: not my superpower). I brought my values with me and started a journey to grow my team through some awesome and terrifying times to have a creative career and to shape the Rocket Money product meaningfully, all while working remotely. There’s no poetic way to say this: it changed everything.
Leadership didn’t pull me away from design as much as it reframed it. Work became less about shapes on a screen and more about the people moving them around. I find myself paying attention to my team the way you’d pay attention to a landscape — how it responds to pressure, how it recovers after a hard season, how it grows best when there’s just enough structure and just enough freedom. It’s incredibly humbling. I have to understand people’s motivations now, sometimes even anticipate them, just to be effective. And my job is to create a team environment that feels fulfilling, maybe even enriching, to build a career inside of. That’s tough work for me. I tend to keep those parts of the job at an arm’s length, and now my days are about confronting them head on. I’m not formally trained in any of this, but I’m beginning to recognize it as the most important work I’ll do at Rocket Money.
This role shift also coincided with the beginning of the fall soccer season and coaching the same group of the world’s most chaotic 9 year olds rang eerily similar to the people wrangling I do at “the office.” It turns out these two roles inform each other so much and really explaining the meaning of the “middle” and the “center” of a field mean two entirely different things. There’s nothing that will have you hone your craft of communication quite like children. They seemingly remember nothing and everything at the same time. Between coaching and leading and traveling, I started to feel how scattered the year had made me.
In September, I settled into a new house where Quinn could have a yard again. She’s been my best companion since moving in and is growing into an energetic but sweet-as-pie senior dog. I love her deeply. I also feel guilty that I leave her every three weeks to get on a plane or train for work. Maybe that’s part of care too, the ache that comes with loving something that waits for you.
Somewhere in all this movement, I let cycling fall away. No races, no long forest roads, no hundred-mile journeys where the world softens into a rhythm you can only feel on two wheels. I miss it. I miss the community around it, the freedom it gives me, the way time felt both slow and fast simultaneously. My life is full, there is no doubt. But of the right stuff? I’m not so sure. Riding bikes has always balanced out the rectangle moving I call a creative pursuit. In reality, my best creative energy is put toward planning bike routes, scouring satellite maps for safe places to poop, and where I can find my next cup of coffee and a hot dog from a corner store. The momentum of a ride on two wheels is all the catharsis I search for when all is lost in the world, and I’ve never felt farther from it than I do today.
Creativity is another place where I feel the loss. I’ve stopped journaling (although I suppose this counts). I don’t draw anymore. The camera I used to carry everywhere is on a shelf now. I know the longer I stay away, the harder it will be to return, and that fear sits with me. My schedule is full and my mental capacity to create feels drained on the few days I am not scheduled. But I’m healthy, and I’m taking care of myself, and I’m caring for others more which is good. It’s confusing, but I still feel excited about that potential.
Looking back, 2025 has been a transformative year, one that ignited parts of me I haven’t felt before and let others lie dormant that I’ve typically tapped into. A year of contrasts rather than balance. Ideas and actions opposing each other, asking me to sort through them to move forward. I know I need to return to making and moving, but now they must mix with OKRs and strategy sessions. I can feel the cost of not moving my body. That’s my direction — touching the world with my hands instead of only my thoughts. I need a life where the things that drain me are balanced by the things that ground me. In essence, I gotta touch more grass.