Last weekend, I spent four hours and seven minutes in a bike saddle grinding through 58 miles of Ohio countryside. It was my first organized ride of this distance and I had no idea what I was getting myself into.
But as I reflected on my 4 hours in the saddle, pedaling into a headwind with my legs screaming, a thought hit me: this feels awfully similar to a career in design. The long stretches of uncertainty, the unexpected challenges, the moments when you question what you were thinking, and the incredible satisfaction of pushing through to the finish to accomplish something amazing.
By the time I rolled across that finish line, sweaty and exhausted but grinning like a delirious fool, I'd learned five lessons that have nothing to do with cycling and everything to do with surviving and thriving as a designer. Ok, maybe it had a little to do with cycling.
Lesson 1: You're More Capable Than You Think
Mile zero was exhilarating. Standing at the starting line, surrounded by 1,600 other riders. Some in professional-looking gear with bikes that cost as much as my car. Others were more like me. And many more were other varieties of uniqueness. My internal monologue was a mix of: “Well you certainly won’t win”, and “At least I’ll finish”, and “Wait, 58 miles is a lot, what were you thinking you dummy?”
I failed to meet my personal goal of under 4 hours at a 15mph overall pace. But, four hours and twenty-seven minutes later, I crossed the finish line with a 14.1 mph pace. Not first, not last, but I finished. The same legs that felt inadequate 5 miles in carried me the entire distance. The same stomach that struggled to keep down one donut, held in until the end. This isn’t a brag on my shrimpy physical prowess, it was a reflection that I was capable to do something pretty amazing for a guy now in his 40s. I finished…something that I wasn’t sure I could do around mile 49. And, when I think about my next cycling challenge, I’m already thinking about how I can do better.
Carol Dweck calls this the growth mindset, and it's built on one simple but powerful concept: the power of "yet." Prior to last weekend, I’d never ridden 58 miles. While I was confident I could, I hadn’t actually done it…yet. Up to this point I hadn’t proven I had the strength or endurance.
As designers, we face “impostor syndrome” all the time. You walk into meetings with engineers who've been coding since they were twelve. You present to executives who've been making business decisions longer than you've been alive. You critique alongside designers whose portfolios make you want to hide under a rock. You work for managers who can poke holes in your solutions like Swiss cheese.
But, you don't have to be a “rockstar” to make a real impact. You don't need to be the best designer in the room to solve problems that matter. You just need to keep showing up and pushing forward, one pedal stroke at a time. You need to keep working hard.
The next time you hear yourself say "I can't do that," try adding one small word: "yet." It changes everything. You can't design a complex enterprise system...yet. You don't understand that technical constraint...yet. You haven't earned the respect of that difficult stakeholder...yet. That little word opens up possibility instead of shutting it down. It acknowledges where you are while pointing toward where you need to go. And most importantly, it reminds you that your capability isn't fixed. It's something you build, mile by mile, pedal turn after pedal turn.
Lesson 2: Ride with a Buddy
The first seven miles were perfect. I started with a close group of friends, and we chatted and encouraged each other as we rolled through the morning countryside. We cracked jokes and laughed. We ate donuts together. We had fun. But around mile 10, I was feeling strong and wanted to push for that 15mph pace, so I broke away from the group and started riding solo.
Then, around mile 20, I unexpectedly met Jim.
I'd been maintaining a decent 15mph pace on my own, but I was also working way harder than I needed to. Jim pulled up behind me (very close behind me) and asked if I knew how to draft. When I sheepishly admitted I didn't, he gently introduced me to the idea, took the lead and he spent the next twenty miles showing me what it was all about.
For those unfamiliar with cycling, drafting means riding closely behind another rider to reduce wind resistance. Done properly, I hear it can save you up to 30% of your energy. Jim and I took turns leading and following (admittedly he lead more than I did), and suddenly what had been a grueling solo effort in the cornfields of Ohio became a less grueling team effort. We shared the effort.
Jim was clearly the more experienced rider, but he didn't see teaching me as slowing him down. He understood something fundamental about endurance challenges: having someone with you makes both of you stronger.
Design has the same dynamic, but too many of us try to go it alone. We try and be the maverick. We try and bust ahead on our own.
Maybe you're a team of one, isolated in an organization that doesn't really understand what design is. Maybe you're surrounded by other designers but feel like you're in territorial warfare. Maybe you're so focused on proving yourself that you forget to look for the people who could help you draft through the headwinds.
When I reflected on Jim’s effort it reminded me that mentorship flows both ways, even when there's a clear experience gap. He helped me save energy and maintain pace. While I wasn’t as experienced, when I took the lead and worked hard, he saved effort too. We both finished at a faster pace because we rode together. Designer and design managers…take note of this. Design is better together.
If you’re a designer, find (or build) your design community. Seek out the Jims who can teach you to draft through industry headwinds. But also be willing to be someone's Jim, even if you're not the most experienced designer in the room.
You can join design communities, both online and local. Attend meetups, even when you feel intimidated. Reach out to designers whose work you admire. Start conversations. Share what you're learning. The design world is full of people willing to pull you along, but you have to put yourself in the draft.
If you’re a design leader or manager, look out for those who have a good design pace, and ride up behind them. Teach them what you know. Help them maximize their effort. Advise them on how to navigate difficult relationships. Spend time to pour into them. It’s not a waste of your effort. It’ll payoff for you and your whole design org too.
Design isn't a solo sport. The best work happens when we stop pedaling alone and start moving forward together.
Lesson 3: Be an Encourager
Early in the race something unexpected happened. I got passed a lot. Ok, that wasn’t unexpected. What was unexpected was as people passed me they said, “Keep going, you’re doing great”. Immediately, it put a smile on my face. That little dose of encouragement made me realize they were looking out for me. While it reinforced the whole “ride with a buddy” lesson, the more important lesson it taught me was to be encouraging.
These weren't people I knew. They were strangers who took a moment to offer encouragement to a clearly less capable rider. They were only a few simple words, but they helped carry me along those 58 miles many, many times.
The real test came in miles 20 through 40. It was the longest, most brutal stretch of the entire ride. These twenty miles were a long slow uphill ride, many times directly into the wind. The crowd of 1,580 I'd started with were widely dispersed. Late in those “middle 20”, I was alone, grinding through the hardest part of the course.
That's when the power of encouragement really hit home. Every few miles, someone would ride by and shout something supportive. "You're crushing it!" or “Doing great!” It sounds cheesy, but those moments were like shots of energy when my tank was running empty.
If you know me personally, it’s probably not a shock to know that I started doing it too. When I passed any riders, I'd call out encouragement. When I saw the many volunteers and police officers along the way, I thanked them. I discovered something in that: being encouraging actually helped me keep going. It shifted my focus from my burning legs to lifting others up and somehow that made my journey less horrible.
I discovered something in that experience, and it turns out there's solid research to back it up. Research shows that positive mood enhances creativity and problem-solving abilities. It's not just about being nice (though that’s a good incentive by itself), it's about creating conditions where great work can happen.
In design, we often get caught up in “critique culture”. We're trained to spot problems, identify what's not working, find the flaws. That's important, but it's only half the equation. (Plus, many of our stakeholders give us enough unsolicited critique.) The other half is creating an environment where creativity can flourish, where people feel safe to experiment, where failure is treated as information rather than judgment. The goal is that someone can proudly share their crappy first draft and it’s received with open minds.
This doesn't mean false praise, celebrating mediocrity, or avoiding difficult conversations. It means recognizing when someone is grinding through their own version of miles 20-40, and choosing to be the voice that says "you can do this" instead of raining down discouragement on them. Be honest, but in a way that points them forward.
Start looking for opportunities to encourage others. Celebrate the small wins in team meetings. Thank the people who support your work. Acknowledge the effort, not just the outcome. Call out good thinking, even in failed experiments.
Being an encourager doesn't just make other people stronger. It makes you stronger too. When you contribute to a positive design culture, you're creating the kind of environment where your own best work can emerge.
Still don’t believe me yet? Well, consider that the quality of your design work is often directly tied to the quality of your relationships. Encouragement builds those relationships. And strong relationships make everything else possible.
Lesson 4: Find Your Motivation
Mile 48 was supposed to be the beginning of the easy part. It was the last stop in the midst of the long haul.
If you read the elevation map, you’d think it’s all down hill from there. What the map didn’t really show was the rolling hills that felt like mountains when your legs had already carried you for three and a half hours. My pace slowed to a crawl. My water bottles of electrolytes running low. The sun was beating down. I found myself asking the question every endurance athlete dreads: "What the heck was I thinking?"
This is when raw brute strength isn't enough.
For me, it was a mix of things. I'd recently turned 40 and wanted to prove to myself that I still had a lot left to give. I wanted to have fun with my friends who'd talked me into this crazy ride. And honestly, I wanted to accomplish something that scared me a little bit. Plus, I love the experience cycling.
Those final few miles had a surprise in store. Around mile 49, I started seeing handmade signs along the route. From what I could tell, a mom had made them for her kids who were doing the ride. They were funny, encouraging messages every few hundred feet so. They weren't meant for me, but they became my lifeline.
My favorite one was: “Dig deep! Like a kid searching for boogers.” For five miles, these silly signs kept me laughing and pedaling wondering what the next one would say…even when my legs were screaming to quit.
As I look back on that moment, I was so close. But the temptation to quit was still there. Motivation doesn’t come from your strength. Motivation comes from why you do what you do. Sometimes it's the big goals, like riding 58 miles. But in the middle of a ride, trying to accomplish that big goal, there are micro motivations that can keep you going on the bigger path.
As designers, we need these kinds of motivations. As you encounter different challenges in your day-to-day, ask yourself how they map to your big goals like career advancement, skill development, or building up respect or credibility. But sometimes you might not see that, so consider connecting it to the little ones too. For some designers, it's making technology a touch more accessible. For others, it's adding a little more beauty and delight to experiences that bring joy to everyday interactions. Maybe it's helping small businesses compete with big corporations, or making complex information understandable, or simply making people's daily tasks a little bit easier.
Whatever it is, be intentional to be aware of it. And remind yourself of it regularly, especially during those mile-48 moments when everything feels harder than it should.
Consider writing it down. Make it visible. Share it with mentors or close collaborators you trust. Because when the professional challenges get overwhelming, when the politics get frustrating, when the work feels monotonous, that personal motivation is what can keep you pedaling forward.
The mom's signs weren't sophisticated or professional. They were written with a fat sharpie marker on standard white poster board. But they expressed care for another human in the midst of a difficult challenge. Your design work benefits from that same kind of connection to purpose, reminding you that you care about more than just the job itself.
Lesson 5: Endurance
In those final miles my mantra became, "Bike riding is easy. It's just one turn of the pedals.”
This might sound unhelpful, but with someone who’s served over 15 years in design, it’s one of the most important lessons of all. Endurance isn't about superhuman strength or talent. It's about continuing to show up. It's about understanding that you can change your pace, adjust your position, eat a donut along the way, but you don't quit. You don’t just give up.
Design careers require this kind of endurance at multiple levels.
At the project level, it's about persevering through the messy start of projects. That early phase where people don’t know what they want, what the problem is, or what the project is even supposed to accomplish. It requires endurance as you explore dozens of concepts and none of them really work, stakeholders get impatient, and you start doubting whether a good solution even exists and you’ll end up shipping something “terrible”. This is where most mediocre design happens, when teams get tired of searching and settle for the first thing that's "good enough."
But optimal solutions live on the other side of that frustration. They emerge when you push through the discomfort of not knowing, when you try one more iteration, when you approach the problem from an angle you haven't considered yet. It's not necessarily about working longer hours, it's about maintaining curiosity and persistence when everything feels stuck.
At the career level, endurance means staying in the game long enough to develop real expertise. To build up a strong backlog of experience filled with failure and success. To experience a variety of situations and design challenges. The design industry is full of people who got excited about the glamorous parts of design, hit the first real challenges, and quiet quit on the discipline of design. We need designers who build lasting, impactful careers, filled with a growth mindset and understand that mastery takes time, that setbacks are learning opportunities, not judgements against you.
And at the design practice level, endurance means pushing through difficulties and resistance. Every designer knows the feeling of staring at that project brief, unsure what the next step is, feeling like there’s no way to accomplish it, crying foul on the whole thing. This is where that "power of yet" becomes crucial. You don't have the right solution...yet. You don't see the pattern that will unlock everything...yet. You haven’t convinced any partners…yet.
Blocks in design work may act like stop signs. But remember, you only stop for a moment at a stop sign before proceeding. These blocks are obstacles that require patience and exploration. Sometimes you need to step away and let your subconscious work. Sometimes you need to try a completely different medium or method. Sometimes you just need to make something, anything, to get unstuck.
The key is understanding that these challenges are part of the process, not evidence that you're a failure. When you accept endurance as a core requirement of design work, you stop interpreting difficulty as a sign you should quit and start seeing it as a sign you're still working on solving the full scope of the problem.
The reality is that most design work isn't glamorous. Novel problems don't have obvious solutions. Solutions require multiple rounds of refinement. Refinement happens when you’ve been working on a problem for a long time and would rather move on to something else that’s more interesting.
But that's also where the satisfaction can live. Not in the moment of inspiration (that’s exhilarating), but in the steady progress of turning a complex challenge into an elegant solution that solves for the business and the user. Not in the final presentation, but in the wholistic view of all the small decisions that compound into something meaningful.
Just like a long bike ride. Crossing the finish line felt incredible. Not because it was easy, but because it represented miles of refusing to give up.
The Wind at Your Back
As I approached the finish line, saw my wife, kids, and some friends waving at me I was overcome with emotion. With my body flooded with endorphins from hours of riding, I was elated to have done it. When I started the ride, I had no doubt I could finish. I was naive. I didn’t realize the difficulty that 58 miles of riding would bring. I had no idea how badly my legs would be burning. I had no idea how much water and food I’d eat. The person who started the ride didn’t exist anymore. I had learned through my journey, adapting and learning my way to the finish line. It brought a sense of accomplishment.
That's what endurance gives you. Not just the ability to complete difficult things, but the confidence that comes from proving to yourself that you're capable of adapting and growing to meet the challenges that come ahead.
I don’t support harmful tech cultures. I also don’t believe that design is for everyone. Not everyone is a designer. But, I do want to offer some encouragement.
If you're reading this as a designer who feels overwhelmed, who wonders why your education didn’t prepare you, who questions whether you're cut out for this crazy, challenging, constantly evolving field….I want you to know something: you're more capable than you think. You don't have to be a rockstar. You don't have to have all the answers. You just have to keep going, keep learning, keep working at it. Find community. Be an encourager. Know your why. And above all, understand that endurance comes from ordinary persistence applied over time.
For design leaders, who are tempted to do it all themselves, to micromanage, or to grumble about the state of the industry…give time to the designers on your team and the industry. Be encouraging pointing people to the future. Root your leadership in a productive purpose. And please don’t give up on cultivating healthy design practice.
Design careers aren't sprints. They're long, sometimes grueling rides through deceptively changing terrain, with unexpected challenges and beautiful vistas and moments when you feel like you’ve lost touch with reality. But if you can develop the endurance to keep pedaling through all of it, you might realize that reaching the finish line is one thing, but enjoying the ride is something incredibly satisfying.
The road ahead is long. There's so much to discover, create, and accomplish than you can see from where you're sitting right now.
So how will you ride your next mile? What's the design challenge that’s in front of you? Keep pedaling. I hope this encouragement puts some wind is at your back.