photo of sandy road with sign saying passable by 4-wheel drive only
Lead People

Letting go of the steering wheel

There’s a backcountry off-road route through the US from the Mexico border up to Canada. That’s 2,727 miles of dirt, mud, rocks, and bumps that add up to one hell of a ride. I just finished this adventure — almost all of it as a co-pilot. It’s been a unique vantage point from which to ponder nature, life, and what I’ve learned in my recent switch from designing (driving the car) to managing designers (being the co-pilot).

The switch

As a designer, there’s something about kicking off a project from a blank page that got my heart racing. It can be as exhilarating as barreling down a dirt road not knowing what’s around the next corner.

You find yourself fighting for every design element, word, color, or interaction on the page. Handling questions from partners at every turn. “Is there a better word we can use here?” Or, “Can you make the logo bigger?” Even, “We’ve decided to pivot.” 

But design fatigue is real. After 25 years of copywriting and content design, my battle scars had added up. It seemed like the right time to hand over the keys and let someone else drive. Now, two years after taking a design manager role, I’m riding co-pilot in a 1997 Toyota Land Cruiser reflecting on my new-ish managing role.


The one value I can attribute to my ability to successfully manage a team is trust. Let your team learn fast and fail fast. They can’t improve and push creativity without trust from you and their partners. In a survey, 55% of leaders believe a lack of trust in the workplace creates a foundational threat to their company1 and impacts performance. I’m constantly telling my team, “Own it.”

As I look out my passenger window at the single foot of road between us and the 3,000-foot drop to the valley below, trust has never been so critical. So as a manager, offer calm guidance: “Hey, on the right here we have 12 inches between us and death.” But, let your team execute. At times you may just have to close your eyes and grip the “Oh, shit” handle with all you’ve got.


As you and your design team head down the road together building that trust, you’ll notice something. Pride of ownership leads to confidence. The first big bumps might leave you both wide-eyed. The first dirt-road drift into a tree may feel a bit out of control. But the anguish, beads of sweat, hard work, and surprised looks begin to turn into smiles and laughs.

Confidence builds project after project and turn after turn. Until eventually you drift into an S-curve, drift back out of it, catch air, and stick the landing without losing momentum. It’s then that you realize, you never grabbed the “Oh, shit” handle!


We crossed hundreds of metal cattle guards (and jumped a few) on our route. This “mental” fence keeps cattle in their pasture, but lets our 4-wheel beast roll right through. For designers, creative briefs are our metal cattle guards. They give our ideas space to roam, but keep us from wandering too far from home. Read the brief, then set it aside to brainstorm. After all the stickies are up on the board, refer to the brief to see the ideas that don’t really line up to the objective.

In our truck, aka “the Rig,” GPS can help keep us on the trail. But when we’re flying down the trail, having great conversations, and enjoying the scenery, it can be easy to forget to check. There are times when things get off track a bit. No need to panic. 

Sometimes it’s as simple as calling it out right away: “Course correction!” Other times, you let it go a bit to see where it’ll take you. Balancing out the new discoveries you may come across, like an amazing campsite or a new UX flow. Weigh that against how long it’ll take you to backtrack, or how long you’re OK with your design team exploring. 


An ideal plan will include time for detours, setbacks, and little celebrations. But when the trail prematurely ends at a “Road Closed” sign, it’s the co-pilot that’s holding the map. “Where do we go now?”  Listen to suggestions. Show your team some options. Talk it through. Then buckle up and get on your way again. 

When the VP rolls up with a pivot, everyone looks at the team lead. Talk through your new goal. Discuss with the team if there’s a work around or if you’d like to start the design process over again.

Make sure you’ve carved out time for the good stuff. Take breaks with your team to come together and celebrate milestones. Avoid burnout by having more team-building events. On the trail that meant taking extra time to enjoy a vista, smell the flowers, or sled down a snow-covered hill on your sleeping pad (Yeah, that happened!).


Land Cruisers and adventure bikes, veterans and novices, planners and free wheelers, conservatives and risk takers — there’s a ying to every yang on the road and on design teams. At my company we embrace a “bring yourself to work” mindset. Because it’s our differences and diverse backgrounds that make our work stronger and more inclusive. 

If you bring someone new into the team, don’t tell them what to do. Instead, learn from them. It’ll help your team grow and challenge the norms.


I’m a big fan of driving on long road trips. Turn on the GPS and go. When I’m the driver, all the executional decisions are mine. Pass that truck now? 8mph over the speed limit or 12? Gas station hot dog? (Skip that last one and just get jerky).

But here I am, sitting shotgun (which, if you’ve ever wondered, refers to the cowboy sitting up top next to the stagecoach driver holding the shotgun to protect the coach). I’m the one that has to be on the lookout for the team. I do that by scanning the map, calling out hairpin turns, ensuring we’re on route, handing the driver a Red Bull and fistfulls of sunflower seeds, and when we’re in town, scouting out the best place in town for chicken fried steak. 

Because I’m not making all the executional decisions, I get the benefit of taking in the scenery. I look in the side mirror at our trail of dust marking our accomplished route. Just like with my design team. Since I’m not debating word choices on a page, I’m looking at what other teams are doing to see where we can sync or learn. I’m tracking and showcasing our accomplishments. I’m an evangelist for content design. I’m planning our future.

Pictured: Prospector, Gatorbait, Whatchamacallit


When we plan our off-road adventures, there is a beginning and end point with some loose time frames. Just being on the trail is our true destination, but eventually we have to shower and get back to work.

Your design team may have monthly or yearly milestones. But I bet those change often. Make sure you’re always following your company values, headed to your “true north” as Brad Smith, Intuit’s Executive Chairman, always told us. And don’t forget to enjoy design, after all, that’s what got you to where you are today.

You’re on a long, sometimes bumpy journey, enjoy it. And put your team first, because a destination is better when it’s shared.


Rob and friends completed the route in August 2022 and lived to tell about it. He reflected:

Idaho was epic even though it literally tried to kill us at every turn!

12016 survey of CEOs by PWC.