Her latest book, Big Goals: The Science of Setting Them, Achieving Them, and Creating Your Best Life, has been nominated for the Next Big Idea Club. It lays out her BRIDGE methodology—brainstorming, relationships, investments, decisions, grit and excellence—“to improve your pursuit of goal accomplishment and establish more effective pathways to success.”

Her goal for the book is nothing short of disrupting goal setting to helping readers “make their lives happier and feel more meaningful.”

She spoke with SUCCESS writer Matt Crossman about her book. This interview has been edited for length.

SUCCESS: You’ve read just about everything there is to read on this topic. You’ve written about it a good deal too. What was missing that Big Goals provides?

Caroline Miller: I’ve streamlined the science of goal setting by including Locke and Latham’s goal-setting theory. Most people don’t know it, and it’s the most unknown but most replicated motivational and psychological theory that’s ever been created. It was voted No. 1 of 73 management theories.

I have not figured out why people don’t know it because everybody sets goals. There’s a lot of new research that needed to be added onto the back of goal setting to include the nuances that have to be considered when creating strategy. And that is pretty groundbreaking.

S: What is the biggest mistake people make when setting goals, and how does your book address that?

CM: The biggest mistake people make is thinking a goal is a goal is a goal, and they don’t understand the difference between a learning goal and a performance goal. And when you get that wrong, and you treat everything as an outcome you’ve got to shoot for, you will disengage quite often because you haven’t built in the ability to be curious, become engaged in the process of learning.

S: A question I’m guessing many readers can relate to: In the last several years, the market has been so volatile that I’ve struggled to set numerical goals that don’t seem like a waste of time. I’m not even sure how to set goals in this environment.

CM: That goes right to the heart of why I wrote the book. The world is spinning fast, and we’re not in the same environment we used to be. Everything is changing. You can’t expect to sell to the same clients the way you did at the outset of your career. Nobody can expect to sell a car the way they sold a car five years ago. Which means that you go back to the brainstorming (the B in the BRIDGE formulation), which is, “What’s new?”

Am I pegging my goals so that they reflect the reality of the industry I’m in? What is the meaning behind the work I’m doing? Is it to share information? Is it to learn? Is it to do all of the above? Is it to reach a certain segment?

I’m beginning to use artificial intelligence for a lot of these answers. Boy, does it prompt a different kind of thinking. Let’s say you’re in “perplexity.” You pose a question like, “Magazines are closing at the rate of 25% a year. If you were me, and this was what I’m most interested in writing about, where do you think I could take my talent so that I could have the impact I want to have?”

That’s where artificial intelligence truly has become a co-pilot for reinventing or pivoting in life. Once you have understood that, and you’re clear on the end goal and why it’s your goal, I think it’s so much easier to create a strategy that will work with learning and performance goals.

S: As we prepped for this, you told me in an email, “If New Year’s rolls around with the same old formulas like SMART goals, I call them zombie approaches, that won’t die, I’ll lose my mind.” Aside from the fact that cracked me up, it shows your passion. What is it about goal setting that gets you so fired up?

CM: Some of this is personal for me. My three adult children have all lost friends and acquaintances to suicide. And as I was researching my book Getting Grit, what I saw was this generation wasn’t taught how to be granular about how to get where they wanted to go.

They instead thought it would be easy. Because everything before this was like, “If you want it, you can have it,” and right before that was the law of attraction, “If you want it, you’ll attract it.”

I mean, this magical stuff is such BS, I can hardly stand it.

This is a world that requires that we work hard toward the things that matter most to us and that we actually persist in that process with the right strategies. And I believe that part of the anxiety and depression that’s been overwhelming the millennial generation, and now Gen Z, is because they have no idea how to have a dream they can accomplish. And so that’s part of the personal piece for me.

The other piece for me is I was introduced to the Locke and Latham goal-setting theory in 2005 in the very first master of applied positive psychology program at Penn. And I remember saying out loud to no one in particular, “There is a theory on goal setting that has real science?”

I raced home and I looked in Brian Tracy, Zig Ziglar, Stephen Covey, and none of them had quotable research or footnotes in them. I want to bring a better approach to the world because the world deserves to have the right tool to accomplish goals.

For more on Caroline Miller and her views on goal setting and grit, check out her website. Her book Big Goals: The Science of Setting Them, Achieving Them, and Creating Your Best Life is available starting today. More on that here.

Photo by Friends Stock/Shutterstock.com

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As I ate in this suburban St. Louis park, I looked to my right toward a hill that sloped down to a wooded area. Two men walked out from the trees. Their body language was unpleasant, their behavior even worse. One yelled at the other, “Would you let me just look at that map for one second?!”

We were only a few hours into the Castlewood 8-hour Adventure Race, and already that team was at odds with each other. 

I went into this year’s race expecting to write about business lessons I’ve learned in adventure racing. I did not expect “don’t be a jerk” to be near the top of the list, though maybe I should have as that was the chief lesson I learned this year. Adventure racing, which features canoeing, orienteering and biking, offers ample opportunities for jerks to reveal themselves. 

Business lessons from adventure racing

Race directors spread checkpoints all over the woods, or, in this case, all over suburban parks. Competitors have nothing but a map, a compass and their own sense of direction. Whichever team finds all of the points and gets to the finish line first wins. 

That simple description leaves out how frustrating it can be and how frustration brings out the worst in us. That’s just one of many lessons I’ve applied in four years of adventure racing to my career. And I’m not alone. “The crossover is enormous,” says Gordon Wright, founder of Outside PR and former adventure racer who founded an underground event. 

Wright and countless other adventure racers have gained valuable experience on concepts as wide ranging as plotting your own course versus following the pack, risk versus reward and being a member of a team. 

In addition to “don’t be a jerk,” here are the three most important life and business lessons from adventure racing I’ve learned.

1. Have the right gear, tech and equipment—and know how to use it

I have had more gear issues—good and bad, big and small, serious and silly—this year than the rest of my career combined. 

Up until this year, if I was reporting on a long-distance hike and something happened that I wanted to write down, I had to stop, fish my notebook out of my backpack, find a pen and write it down. Then I had to return my notebook to my backpack and my pen to my pocket and resume the hike. My hiking mates would have to either wait for me, which is frustrating for them, or keep going, which is frustrating for me. Either way, I would be wasting a ton of time.

On a hiking assignment in April, I noticed a friend had laced cord through the spiral wires of his notebook, tied the end of the cords together and hung it around his neck like a gaudy yet imminently practical necklace. 

This innovation left me gobsmacked. 

He was gobsmacked at how gobsmacked I was, but all I could think about was the hours—yes, hours—that little piece of genius would have saved me over the years.

I immediately stole his idea. As silly as it sounds, that simple “technological advancement” has already been extremely helpful on four assignments. During the adventure race in December, I took notes while walking and canoeing and barely slowed us down, if at all. 

2. View obstacles as opportunities

Adventure racing is nothing if not a constant battle against challenges—which is exactly the same as running my own business. It’s only the nature of the challenges that are different. 

In any given race, competitors face harrowing bike trails, massive hills to climb and frigid (or soaring) temperatures. One lesson Marco Amselem, of one of the world’s top-ranked pro adventure racing teams, has learned is that some obstacles aren’t obstacles but opportunities. The key to overcoming them is to reframe how you think of them. 

If you view them as opportunities to learn, grow and think differently, you will attack them in a different way. To illustrate his point, he used an example familiar to every adventure racer (and business owner)—what to do when one person slows the team down. It’s frustrating only if you allow it to be. If you instead think of it as an opportunity, it can be a positive.

“If someone is really struggling, sick, it doesn’t mean that the team needs to be affected negatively by that,” Amselem says. “Maybe it’s time for all of us to rest, so we can get stronger and move faster.”

3. Make tough decisions on the fly

Like any stressful endeavor, adventure racing magnifies your strengths and weaknesses. You learn a lot about yourself and your teammates when you’re lost deep in the woods. It’s not about avoiding mistakes. They are inevitable. It’s how you react that matters—loudly demanding to see the map, as I overheard in December, is a recipe for more fighting and getting even more lost. 

So is not admitting you’re lost.

Wright tells two stories that demonstrate this issue. The first came in a multi-day adventure race in Maine. His team guessed it would take 17 hours to complete a trekking portion of the event. 

“After 30 hours, it was increasingly, blindingly clear that we were not only lost, but also our navigator had no point of reference to get us unlost,” he says. “Navigating, like business leadership, is a two-way road of trust. My other teammates and I supported our navigator until it was apparent they were overwhelmed.”

After 46 hours, Wright and the other teammate finally gave up and convinced the navigator to radio for help, which disqualified them from the race. “But it was the right thing to do,” he says. “We got rescued and likely saved our lives in the process.”

Another time, Wright and his team were mountain biking in the dark. They were cold, exhausted and not thinking clearly. “Our navigator, a far more experienced and humble one, gathered the rest of us around him and said, pointing at a map, ‘This is where we are, I think. But I’m wrecked, we’re near a cliff and I’m not 100% sure where to go next. I think we should bust out our space blankets and grab a half-hour nap. It’ll be light enough then to make a better route choice—what do you guys think?’”

That moment of clarity amid confusion helped the team collect their wits, and they ultimately finished second in the race.

“And you can guess which person I’d like to work with,” Wright says.

Photo by TORWAISTUDIO/Shutterstock.com

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Flat on my back, I looked at the dull sky… and realized my hands were still in my pockets. All of that happened so fast I never had a chance to take them out. I sat up, looked around to see if anybody saw that—NOPE!—laid back down and laughed. Eventually I pulled myself off the dirt, got back on the bike and went to work.

As a boy, I spent every waking hour outside—riding, playing sports, jumping off my friend’s garage into his pool, whatever. As I turned in my bike for a car and a fast-food job for a journalism career, my outside life dwindled. I didn’t have time to ride hands-free through a park, and I started to think flying over the handlebars was frightening, not funny. I pursued safety and comfort, and neither was to be found outside.

When I lost my job, I lost that safety and comfort. As a newly laid-off magazine writer desperate to land freelance assignments, I wrote a story about hiking. I had a blast, so I wrote another, then another. Suddenly I loved the outdoors again. Hiking turned into long-distance bike riding turned into adventure racing turned into wanting to try everything once—rock climbing, ice climbing, dog mushing, surfing and more.

As much as I loved being outside, I still craved safety and comfort. Fear rode shotgun, whispering to me that I could not, should not, do whatever it was I was about to do: You’ll get hurt. You’ll make a fool of yourself. You will fail and be exposed as a fraud.

Those whispers became shouts this winter as I endured the worst stretch of my career. All at once, clients stiffed me, closed and tore my stories to shreds. When I have no confidence inside, I sure as hell don’t have any outside. For the first time in 30 years, I thought seriously about changing professions.

And then I was invited to attend the Scouting Jamboree at Summit Bechtel Reserve, a massive 14,000-plus-acre adventure park in West Virginia. Alongside 15,888 scouts from 50 states and 12 countries, I would have the chance to go mountain biking, rock climbing, rappelling and more. I said yes… and as the summer date approached, I regretted it. I told my wife I wanted to cancel the trip. She (lovingly) pushed me out the door. I arrived at the Jamboree dripping in angst and ready to revert back to a life of safety and comfort inside. There I met adventure-loving kids who showed me how wrong I was.

The good news: Blood spilled onto that mountain. The better news: It wasn’t mine. A teenager in front of me crashed his mountain bike, leaving one leg caked in mud, the other trickling blood—and his heart full to bursting. As he dusted himself off, his every movement screamed joy.

That’s what I’m afraid of? That looked like fun! Memories surged back to me. Seven years ago, on my first mountain bike ride, I flew over the handlebars in Colorado and landed on my face and chest. Didn’t hurt. Three years ago, someone stopped in front of me as I crossed a four-lane highway as a semi approached. Unable to unclip from the pedals, I pounded onto the pavement with my shoulder. That bruised only my ego.

It seems like by now I would know I don’t ride fast enough to get seriously hurt in a crash. That boy reminded me. The next time I’m worried about crashing, I’m going to think of the pure delight on his face as blood oozed from his calf.

He was bleeding. I was jealous.

Sabrina Wang shared with  me a badass story about the time she backpacked 100 miles in nine days. Every morning she asked herself the same question I ask myself on nearly every adventure: Why am I doing this to myself? And every morning she gave herself the same answer: friendships.

She was not done saying that word before I realized that was my answer too. The faces of a half-dozen men flashed across my mind, men with whom I have powerful, abiding relationships. Those types of relationships form when you endure challenges together. Wang reminded me of that in a way I won’t soon forget.

I waited for mountain bike lessons alongside James, who’s 17 years old. A few weeks earlier, he rode for the first time and crashed into three trees. “I was still shaking when I got on this bike,” he said. “But if you’re really scared and don’t do something, you might miss out on a lot of fun.”

We circled around our instructor. He told us to keep our eyes on the trail because our bikes would go where our eyes point us. “Don’t look at the trees,” he said.

Brendza looked over his shoulder at me and flashed a smirk that should be bronzed and put in the Smithsonian.

He pedaled down the path toward a scouting official who would assess whether we handled this beginner’s trail well enough to move on to the next level. I followed Brendza, my eyes darting up the trail looking for danger and finding plenty but avoiding all of it.

Here was the fear-facing lesson I needed. I rode past the judge with the biggest, dopiest, bring-on-the-crashiest smile on my face… with both hands gripping the handlebars.

Photo by Dewald Kirsten/Shutterstock.com

The post I Left the Comfort of Safety to Face My Fears Head-On—Here’s Why appeared first on SUCCESS.

I didn’t mind the laughter—or failing, either, even in front of people. It’s (almost) enjoyable; it’s how I learn. But I do mind failing without knowing how to get better. That feels pointless. I had not been trained properly in skeet shooting and had no clue what I was doing wrong. For that reason, I never wanted to shoot skeet again, and I had no intention of doing it until I visited Primland Resort—a breathtaking 12,000-acre lodge in the Blue Ridge Mountains that Travel and Leisure called one of the best resorts in the South.

Sammy Howell, a Primland shooting instructor, drove us along a mountain road. Grandeur swallowed us as I described my struggles. At least here, high up in the mountains, nobody would see me fail except Howell. But he assured me he encounters guests like me frequently. To teach them, he stands behind them and watches, offering tips, as they follow the target with their unloaded shotgun. After a few minutes, he loads the gun and tells them to fire on his command. “When I say ‘shoot’—boom! They’ll break it—every time,” he says.

I arrived at Primland while researching how to take (and hit) the Big Shot, and skeet shooting provided an opportunity to test what I had learned. After hearing Howell’s instruction, I was 98% sure I would shoot better.

As we walked up to the wooden shooting platform, 98 became 100. We rehearsed like he described. I hit the first six—more than I hit that entire first day—and, all told, shot like a different person. That gave me Big Shot lesson No. 1: Proper coaching and training are crucial.

Here’s what else I have learned.

1. First, take a bunch of small shots. Then, push yourself. 

The tech world dumps jobs every day, while nearly 90% of construction companies can’t find enough qualified workers. That volatility pushes some people to want to take the Big Shot. It makes others skittish, because if they miss, they don’t know what they’ll return to.

Statistics (and common sense) show that the younger you are, the more willing you are to take the Big Shot, whether that’s changing jobs or careers. You’re also more likely to miss because you don’t know what you don’t know. As painful as missing is, it’s invaluable. I learned that on the Appalachian Trail during my first overnight backpacking trip.

It rained so hard the trail became an inch-deep creek of running water. My cheap rain gear failed (didn’t-know-better mistake 1), and the clothes on my body and in my backpack were soaked. I also committed what I now consider a comical error of wearing cotton (didn’t-know-better mistake 2), which takes forever to dry. On top of that, the temperature was 10 degrees colder than I was prepared for (didn’t-know-better mistake 3). High 50s and sunny is awesome hiking weather. High 40s and drenched is borderline dangerous. My inexperience put me at risk.

By luck, my group stumbled upon a shelter that protected us from the elements. Without that shelter, I might have never hiked again. With it, I learned valuable lessons—most notably about how failing in one Big Shot prepares me for the next. Since then, I have hiked in Virginia, Alaska, California, New Mexico and many more places, each a little more daring, each one applying what I had learned previously.

This spring, 11 years after that horrible first hike, I planned and executed a three-day, two-night hike in the Ozarks. I led a group of 14 others—a Big Shot I never could have taken without attempting so many smaller shots first.

2. Don’t worry about what someone else’s big shot looks like. 

Josh Wise is known in NASCAR as the driver whisperer. An optimization coach, he coaxes stellar performances out of drivers with a holistic approach focusing on craft, fitness, wellness, mental toughness and more. He’s so good that some of his clients won’t talk about him because they don’t want anyone to know what’s fueling their Big Shots.

In May, I embedded with Wise as his clients practiced. He asked them to run what I’ll call Big Shot laps (his term is more colorful) followed by conservative laps (which he calls “no-slip”). A Big Shot lap is aggressive and marked by the tires spinning and the car getting sideways in turns. In a no-slip lap, neither of those things are supposed to happen.

I watched a driver named Sheldon Creed. My takeaway was not what Creed’s Big Shot laps looked like but that even his conservative laps were aggressive—perhaps as aggressive as another driver’s Big Shot laps. That’s because Creed grew up in off-road racing, a style of driving in which the tires spin and the car slides on every lap. That means he’s more comfortable being uncomfortable. While some drivers have to be pushed to be more aggressive, Creed had to be told to be more intentional about taking it easy.

3. You need to be ready when your chance comes, recognize when it does and acknowledge you are not in control.

“A legacy of weirdness” is how J.P. Morgan Chief Global Strategist David Kelly described the post-pandemic job market. “A recession is coming!” says one headline. “No, it’s not!” says the next. It’s challenging to take a Big Shot amid uncertainty. The best you can do is make decisions based on the available information, however incomplete it is.

I learned this while taking surfing lessons and conducting research into how artificial intelligence and human experience put surfers on a never-ending quest for perfect waves. At the risk of oversimplifying, AI refines billions of data points to predict what the waves will be like, and then surfers paddle out to enjoy what AI predicted.

But AI forecasts what all waves will be like, not what each wave will be like. My instructor watched the waves as they approached and only let me try to surf those that looked good. I rode the first two almost all the way in. His third choice, while indistinguishable from the first two, immediately crashed on my head as if I opened the attic door in my ceiling and a trunk fell out.

I asked my instructor why that wave crashed while the others rolled. He shrugged. The not knowing is part of the fun. Some waves crash, some roll. The best we can do is pick a wave that looks good, stand up and ride—for however long it lasts.

This article originally appeared in the September/October 2023 issue of SUCCESS magazine. Photo by Bennett Walker/Shutterstock.com

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Crashes can’t be eliminated, but there are steps parents can take to improve their kids’ safety. Many cars come equipped to slow when you get too close to the car in front of you, correct your path if you drift into another lane and tell you if someone is in your blind spot. Those features work for everybody, not just teens. Several manufacturers have functions specifically targeting teen safety built into some models. 

But do most parents know this? That’s doubtful. The Insurance Institute for Highway Safety (IIHS) found salespeople and manufacturers could improve the way they explain and promote the systems. Chevrolet does a better job than most, the IIHS found. Chevy’s teen driver safety feature, available in several models, allows parents to program the car to refuse to go into drive until seatbelts are fastened, set a speed maximum and put a limit on how loud the radio or streaming device can be. The feature produces a “teen driver report card,” which the manufacturer says may include “distance driven, maximum speed, overspeed warnings, number of times the accelerator pedal was floored and when certain safety systems were triggered, such as traction control.”

In addition to features within the cars, there are also myriad driving safety apps, or at the very least report teen driving behavior (both safe and unsafe). Like nanny cams, the apps let parents know what’s going on when they’re not there. Some apps produce reports gauging a driver’s performance based on speed, acceleration, braking and more. The parents can use that information as they see fit. 

4 driving safety apps for you and your teen

Life360

Many of these apps cover the same basic ground. This seems to be the most popular, at least in my peer group. With millions of downloads, it covers more than just driving: It offers crash detection, emergency dispatch, roadside assistance, a family driving summary and individual driving reports. 

RoadReady

RoadReady promotes its ability to track driving time. We live in Missouri, which requires teen drivers to have their permits for six months and reach time thresholds in total driving time and night driving before getting their licenses. The state doesn’t mandate proof that my daughter reached those limits, but that doesn’t make me want to hit them any less. RoadReady offers a simple way to keep track.

TrueMotion Family Safe Driving

This app gives all drivers, not just teens, a score based on how they drive (avoiding distraction, following the speed limit, etc.). When parents use it as well, this gets rid of the teen driver’s lament that it’s not fair that they are scrutinized and nobody else is. This also allows for friendly competition, as parents and teens can compare their scores and strive to improve them. Frankly, in analyzing my own behavior in the context of teaching my daughter to drive, I have learned that I could use a refresher course.

DriveSmart

This app automatically routes incoming calls to voicemail, mutes notifications about incoming texts and sends a reply that the user is unavailable. Like many other features across these apps, this is geared toward teens but would be valuable for any driver. Does any of this help? In a study of in-car safety features and teen-specific technologies, the IIHS concluded, “Assuming those technologies were universally used and completely effective, the researchers concluded that together they could prevent or mitigate 41% of all crashes involving teen drivers and as many as 47% of teen driver injuries and 78% of teen driver deaths.”

Matt Crossman is a 20-year NASCAR writer who recently taught his teenage daughter, Maria, how to drive. Armed with driving tips from such renowned names as Jeff Gordon and Jimmie Johnson, Crossman primed Maria on the rules of the road and found they were also applicable to navigating one’s job. He shares those reflections in his article, “4 Driving Lessons from the Pros that Will Help Your Career”, as well as the driving safety apps mentioned here, to help others stay informed on ways to keep teen drivers safe.

Photo by kuzmaphoto/shutterstock.com

The post Keep Your Teen Safe Behind the Wheel with These 4 Driving Safety Apps appeared first on SUCCESS.

I expect her to be herky-jerky on the brakes and put me halfway through the windshield. When I think she should slow down, I mash my right foot into the floorboard, and my right hand just about rips the grab handle off the car ceiling as I tell her as gently as I can, “Brake, BRA-ke, BRAKE BEFORE WE ALL DIE, BRAKE!”

She has never come close to running a red, never come close to rear-ending a car, never done anything remotely justifying my reaction. Every single time, she stops early and gently, and yet I kept flipping out anyway. “I am braking,” she finally said, and I’ll be darned: She was. She is so gentle on the brakes I couldn’t, and still can’t, feel us slowing down. How she learned to do that I have no idea.

She—I’ll call her Maria Andretti Crossman—has also made it clear she doesn’t need me to point out what color stoplights are. “I can see the light is red; you don’t have to tell me,” she said, the tone in her voice overflowing with I’m-not-a-baby-anymore-Dad! exasperation.

Who’s teaching whom, I have thought more than once.

I’m learning—or trying to. I haven’t slammed my foot into the floorboard in weeks, and I graduated from saying, “The light’s red,” to thinking it as loud as I can. Proof that that works: She hasn’t run one yet.

Professional Driving Lessons for the Road—And Life

I realized along the way that maybe, just maybe, I’m not the best teacher for this situation. Then a solution as obvious as a Mack Truck barreling toward us on a one-lane road dawned on me: As a NASCAR writer for more than 20 years, I have access to the greatest drivers in the world. I can ask them for advice to pass along to my daughter.

So, I did—and a funny thing happened. In addition to giving Maria driving lessons, I’m learning how I teach, how she learns and how to use that knowledge to get where we’re going, whether it’s in a car, a job or a career. The lessons happen seemingly every time she puts the car in drive, slowly accelerates and comes to a soft, gentle, complete stop.

Lesson No. 1: Learn by doing.

When I first started covering NASCAR, I could not understand how drivers could race so close to the wall and each other for hours on end. I still don’t understand, but at least I know they did not start out able to do that. They learned through trial and error. Even the great Jeff Gordon—a four-time champion, one of the most transformative figures in NASCAR history and, like me, the father of a teenage daughter—crashed and wrecked a ton of cars early in his career. He became great because his team owner, Rick Hendrick, had the patience to let Gordon learn from those mistakes.

A few weeks ago, as Maria drove, some idiot wandered out into the road and just stood there. It was night, the road was poorly lit and a car coming from the other direction was going to arrive at the idiot at the exact time we were. I didn’t know if Maria could process all of that—I barely could—so yelling was my natural reaction. “STOP!” I bellowed.

I regretted it immediately, and not just because I startled her when she was trying to drive, but also because I didn’t give her a chance to deal with the problem herself. When I asked Gordon for advice to give to Maria, I didn’t tell him about the idiot in the road, but his answer sounded like I had. “Be aware of your surroundings,” he said. “This comes with time and experience, but it’s never too early to start the process. Knowing what others around you are doing and anticipating their next move can help prevent possible accidents from occurring.”

That applies to work as well. Our surroundings have changed considerably in the last three years. There will be times when yelling “STOP” from the passenger seat is the right call—if a meteor is coming at us or I see Taylor Swift tickets lying in the road. Other than that, I should let her figure it out herself because, after 16 years of being her dad, I know that’s how she learns best.

Lesson No. 2: Don’t be in a hurry.

I haven’t written on deadline much lately, and I’m glad of it. I covered the Daytona 500 many times. The deadline anxiety started when I woke up that morning and kept going as I drove to the track, waited in traffic, walked to the media center, etc. It exploded when the race ended. Every word, sentence and decision about it weighed 10,000 pounds.

Hours later, when I crawled into my hotel room bed, falling asleep was a challenge—my hands would be clammy, my heart pounding, my breathing shallow. My mind would be racing, out of adrenaline, out of elation that it was over, out of fear that I wet the bed on the story.

When Maria pulled into the driveway recently, my hands were clammy, my heart was pounding, my breathing was shallow and my mind was racing. If I was feeling pressure, I knew she must be, too. For Maria, every turn, brake, acceleration and decision about these actions must weigh 10,000 pounds. It didn’t help that I was watching, piling the anxiety of being scrutinized on top of the anxiety of learning a new skill.

I have years of experience dealing with deadline pressure. This is all new for Maria. The key, in driving, in writing, in work, in life, is not to let the pressure force you into bad decisions. “Try not to rush any decision when driving,” Gordon told me to tell Maria. “As a new driver, others around you will understand if you take extra time when changing lanes or pulling out of a driveway—so make good decisions, not quick ones.”

This made me think of my first day at Sporting News, a national magazine for which I worked for 13 years (and covered the Daytona 500 many times). I arrived there after spending six years in daily newspapers, going as fast as I could every day. My new boss gave me a project, I told him I’d get it done right away, and he told me not to.

He told me to do it well, not quickly.

It’s a lesson I have to repeat to myself over and over, especially as a freelancer.

Lesson No. 3: Pay attention to what you’re doing.

Jimmie Johnson is arguably the greatest NASCAR driver of his era; only Gordon is in that conversation. Johnson won seven championships (tied for most with Richard Petty and Dale Earnhardt) and 83 races, including two Daytona 500s, one of which I covered. Like me, he has two daughters, though his are several years younger than mine.

When I asked him for driving advice, he sounded like he was imagining riding shotgun to his girls. He offered what he called a “dad layup” by advocating distraction-free driving: phone down, radio volume low, over-caffeinated friends not invited, etc. That’s great advice that carries over into the workplace in the attention economy. There are a million things clamoring for our attention. We work best—no, we live best—when we eliminate as many of them as possible.

The only problem: Early on, at least, I was often the distraction, whether it was by encouraging her to brake, telling her the light was red or yelling, “STOP,” when there was an idiot in the road. I have since learned to shut up.

Lesson No. 4: Play by the rules—except when you don’t.

I’ve driven with enough NASCAR stars to know it’s better to listen to their advice than to emulate them. While driving a rental SUV, Carl Edwards sped into the tunnel that goes under the track at Daytona International Speedway. He blasted out of the tunnel’s uphill exit and launched us into the Florida night. We landed about 45 feet later and stopped near a parking attendant. “You again,” the attendant said.

I didn’t realize until I started teaching Maria that I set almost as bad of an example. I treat most traffic laws as suggestions: I don’t come to complete stops, I use my turn signal only when I think of it, which isn’t often, and I don’t drive the speed limit. As Johnson said: “We’re not going to be the one in the fast lane going slow.”

Nobody would argue, except maybe Maria. She is a lifelong, rule-following, black-and-white, oldest-child literalist. Whatever the speed limit sign says, that’s what Maria drives. A road near our house turns slightly, and the speed limit drops from 45 to 35, a completely unnecessary change. Exactly one person—Maria—follows it, and often the car behind her gets so close we could join their conversation. That makes her nervous, and at some point, she’ll make a mistake because of it. So far, I am fighting the urge to tell her to break the speed limit, even though I know I should.

But here’s the thing: I wouldn’t advocate she break the law in any other circumstance. I wouldn’t tell her to disregard her boss’ directive because nobody else followed it. I wouldn’t say it’s OK to blow off her homework because all of her classmates were. “Everybody else is doing it” is an ugly reason to do something, and I’d laugh (lovingly) at her if she used it with me in defense of anything… except breaking the speed limit.

The best thing about parenting is this confusion will continue on a variety of topics until I die.

This article originally appeared in the July/August 2023 issue of SUCCESS magazine. Photo by sumroeng chinnapan/shutterstock.com.

The post 4 Driving Lessons from the Pros that Will Help Your Career appeared first on SUCCESS.

Though I had never played, I of course said yes. I always say yes. In the past few years, I have tried surfing, rock climbing, ice climbing, a dozen other new-to-me activities and, now, pickleball. Early in my career, I decided against specializing in writing about one subject. Instead, I chase other people’s passions. I find people who love doing interesting things and ask them to teach me. I do it because it’s fun, because it suits my personality and because it allows me to live a well-rounded life.

I have found there is much more to it than even all that. Being a generalist is a good, albeit unconventional, career-development strategy, though I’d be lying if I said I did it because of that.

In today’s world, we’re bombarded from a young age to pick something to specialize in. We pick a major and then a career and then face admonitions to stay in our figurative lane. Firms and individuals alike are pressured to excel in narrow areas of expertise. The better you are at your niche, the more valuable your work—or so the thinking goes.

There is growing evidence that suggests that line of thinking is too reductive. All of us would benefit from understanding a wide range of areas and recognizing how things are interconnected and interdependent, so we can see the big picture when making decisions and bring multifaceted approaches when solving problems.

The path to becoming a generalist

It’s easy to become a specialist. You pick a lane and stay in it. Being a generalist isn’t so simple. How do you pursue that path when there really isn’t one?

One way is to work for a company that allows, encourages or embraces it. Constance Schwartz-Morini, the co-founder and CEO of SMAC Enter­tainment, is a perfect example.

Early in her career, she landed a job with the NFL. Over the years, she danced between “television programming, sponsorship, events, marketing and player engagement,” according to her SMAC Entertainment bio. She watched and learned, especially early on when she was an assistant. “The NFL was my MBA,” she says.

Schwartz-Morini didn’t set out to become a generalist—she half-jokingly says she wishes she could take credit for pursuing it. While she may not have done it on purpose, she says it seems inevitable in retrospect, because she has the characteristics necessary: She’s intensely curious, eager to learn and willing to ask for help.

It may have been accidental at first, but now she pursues a wide-ranging career very much on purpose. Her work at SMAC Entertainment shows she’s still deep in the generalist life. SMAC Entertainment is “a talent management firm, business incubator and Emmy-nominated production company,” according to Schwartz-Morini’s bio. As a manager, Schwartz-Morini represents athletes and entertainers. As a producer, she works on scripted media, unscripted media and even game shows. As an entrepreneur, she has helped launch clothing lines.

That wide-ranging approach has nurtured her already deep passion for being well-rounded. Now, she tries to create fellow generalists. She manages athletes and entertainers with an explicit eye on multifaceted careers. She won’t represent anyone who wants to stay just what they are—i.e., a specialist.

Her three most famous clients—Deion Sanders, Michael Strahan and Erin Andrews—started out in niche markets. Each was initially well known within that niche and less so in the wider world. Now, all three are household names. They came from different fields and emerged out of their lanes in different ways, because no generalist follows a rote pattern. “The only thing they have in common is me,” Schwartz-Morini says.

Generalists are comfortable seeking outside help

One of the problems with being a specialist is that it lulls you into a false sense of security. You think because you know so much about your field, you can solve whatever problems arise. And you are right—until you are completely wrong.

In his book Range: How Generalists Triumph in a Specialized World, David Epstein writes that if you are struggling with a narrow problem in a niche field, somebody who knows nothing about that field might be better at solving the problem than you are. That’s because the more we know about something (“the inside view”), the poorer our decisions are about it, especially when it comes to problem-solving. “In a wicked world, relying upon experience from a single domain is not only limiting, it can be disastrous,” Epstein writes.

A company called Wazoku created Wazoku Crowd, which gives clients access to crowdsourced problem-solving. A company with a problem pays Wazoku to ask for solutions from its community of solvers, and whoever comes up with the best one gets a reward.

A generalist doesn’t arrive at the top feeling like they need to know everything. They arrive at the top in part because they have been comfortable in new roles in which they didn’t know anything. Schwartz-Morini says she’s good when she knows what she’s doing and even better when she doesn’t, because she is so comfortable seeking outside help.

Gaining ‘the outside view’

What we know puts us in a box that contains only solutions we could reasonably devise from the contents of that box. The answer might be in a different box: “the outside view.” The more boxes we have access to, the better off we’ll be. “The outside view probes for deep structural similarities to the current problem in different ones,” Epstein writes.

The key phrase there for me is “deep structural similarities.” Just about every time I acquire a new skill, I learn something that applies to the rest of my life. In surfing, I learned valuable lessons about how I learn. From an ATV guide, I learned about authenticity. In ice climbing, I learned valuable lessons about trust.

In pickleball, I learned about covering a lot of ground… or tried to, at least. Going into the tournament, I feared that the very skill I am honing and advocating—increasing my range—would be my weakness in pickleball.

I figured I would lose because I wouldn’t be able to reach shots. But that wasn’t the case. Don’t get me wrong. I lost all four matches I played in the 2022 Dietz & Watson Atlantic City Pickleball Open. But the problem wasn’t that I couldn’t get to balls hit far from me. The problem was balls hit right at me. I couldn’t move my paddle fast enough to return those.

This article originally appeared in the May/June 2023 issue of SUCCESS magazine. Photo by Ahturner/Shutterstock.

The post The Benefits of Being a Generalist & Learning New Skills appeared first on SUCCESS.

And when my friend Fred “Honey Pot” Williams, M.D., a 62-year-old gastroenterologist and beekeeper (hence the nickname), talks, I listen.

We talked about friendship; we talked about loneliness; we talked about defeating the cancer that lurks within him—and we talked about how all of those are related.

This conversation came during an annual adventure called 50-50-50 in which my friends and I hike 50 miles, bike 50 miles and canoe 50 miles all in one epic four-day weekend. We originally scheduled it so Williams would join us on the last day of his radiation treatments—a dramatic and symbolic middle finger to his cancer. He missed a couple radiation sessions, so he ended up joining us when he had a few left—an even more dramatic and symbolic middle finger. All weekend, I wondered whether he joined us despite or because of those treatments; I ultimately concluded the answer was both.

We “failed” to complete the 50-50-50 mission this year. A nasty headwind on the Missouri River on Day 1 put us behind schedule and blew up our carefully choreographed plans. We never caught up, so 50-50-50 became 50-50-30, as we fell short on the hiking miles. But if it were easy, anyone could do it, and those miles are the means, not the end.

Why friends are important

The end is strengthened relationships, which are always important, but even more so now, for the 12 of us on the trip as a whole and for Williams in particular. Having strong friendships is important for everybody at all times but especially so for someone enduring a massively stressful situation like he is—frankly, like we all have in the past few years.

A 2021 study by the “American Perspectives Survey” found that “15% of men have no close friendships at all, a fivefold increase since 1990.” According to the Making Caring Common Project at Harvard Graduate School of Education, “36% of all Americans—including 61% of young adults and 51% of mothers with young children—feel ‘serious loneliness.’”

Aside from emotional distress, loneliness may lead to health issues that are widespread and terrifying. According to the “Social Isolation and Loneliness in Older Adults” consensus study report, social isolation—defined as “the lack of social contacts and having few people to interact with regularly,” according to the National Institute on Aging—“has been associated with a significantly increased risk of premature mortality from all causes.” The same meta analysis found social isolation to be associated with “an approximately 50 percent increased risk of developing dementia” and “a 29% increased risk of incident coronary heart disease and a 32% increased risk of stroke.”

An epidemic of loneliness

In its “2022 State of Remote Work” report, Buffer reported that 24% of people who work remotely named loneliness a problem with that lifestyle, second only to “not being able to unplug.” In the 2022 “Social Connection in Remote Work” report, 55% of respondents said they were lonely at least some of the time.

And all of that is going to get worse, because our loneliness epidemic is going to get worse. The future of work is headed toward more employees working remote or using a hybrid model. We’re already lonely. And now more of us are going to lock ourselves in home offices for eight or more hours a day. We are treating the loneliness epidemic with more loneliness.

The situation is dire but not hopeless. “I’m an optimist because the data shows that we don’t necessarily have to become lonelier just because we’re working remotely more often or all the time,” says Kasley Killam, founder and executive director of Social Health Labs and Harvard-trained expert in loneliness and social health.

There are ways to combat loneliness, Killam says, and one obvious way is to build relationships—deep, abiding, face-to-face relationships—through joining groups of like-minded individuals. Yes, those relationships are hard to form, hard to grow, hard to keep. But the stakes are too high, and the benefits too deep, not to try.

Negative effects of loneliness

Research has shown that tight-knit communities experience much better outcomes during and after crises. Our social health helps our physical health. “We understand physical health is about our bodies. We understand mental health is about our minds. I argue that we also need to prioritize social health, which is about our relationships,” Killam says.

In Williams, I see both a model for combating loneliness through social health and proof of why it’s important.

As a gastroenterologist, Williams sees health problems caused by loneliness on a daily basis. Loneliness exacerbates stress, which leads to poor eating habits, which brings those lonely people to his practice. Occasionally, he has patients with nobody to drive them to and from a colonoscopy. His heart breaks for them.

Until five years ago, Williams, too, struggled with loneliness. Most of his friends were the husbands of his wife’s friends and not necessarily men he had much in common with, particularly enjoyed hanging out with or grew close with.

Finding your friends

That began to change in 2017. Always a fitness buff, he joined a men’s fitness group called F3. “It took me 60 years to find my tribe,” he says—but once he found it, his life has never been the same.

In F3—a network of free, outdoor, peer-led workouts with 3,545 locations as of early November with more added every week—he is immersed in a group of like-minded men, and it was with them that he formed more deep friendships in a few years than he had in the rest of his life combined—including with me. And it was to those men, including me, that he turned when he was diagnosed with prostate cancer last summer.

Williams sees his battle with cancer as God’s way of showing him grace and teaching him about humility. He believes God led him to F3 so that when he got cancer, he’d have friends to share his suffering.

He shudders to think of the loneliness he’d endure if he suffered through this without us.

On Day 2 of 50-50-50, we piled into a canoe outfitter’s van and drove along a road that ran parallel to the Missouri River. Thick fog shrouded a valley as we sped into it. As we drove out of it, the blue sky returned.

That’s an apt metaphor for what Williams is going through. Too often we describe fighting cancer as a battle, a test of our toughness, a measure of our resolve, as if the way to win is to have enough of both. I loathe that line of thinking. Williams won’t beat cancer because he’s tough or persistent or in shape, and he’d be pissed at me if I wrote about it like that.

A supportive community

At the same time, his mindset matters. Killam says tons of research backs that up. When he told me he had cancer, he said he had spent a few days wallowing in self-pity. Of course he did! He still goes there sometimes, going into and out of light, into and out of darkness, just as we did in the van. It’s easier to say than to do, but the more he stays in the light, the better off he will be. And one way to stay in the light is to be surrounded by loved ones.

“It’s possible that joining the men’s fitness group and embedding himself in that supportive community could actually improve his health trajectory, ease his symptoms and maybe even help him recover or live longer,” Killam says. “Human connection is truly powerful, affecting us at the physiological level.”

Williams is familiar with the research Killam was referring to. We talked about it as we rode bikes, the river to our right, the cliffs to our left, the gravel underneath us. I asked him: Does going to F3 workouts help in a measurable, definable, medical way? With characteristic humility, he said he did not, could not, know. The research about the importance of mindset during a health crisis, as convincing as it is, speaks to what happens in bulk. It does not say what is happening inside one body at a particular point in time.

The lasting benefits of friends

Then he said something that floored me.

“Even if it doesn’t help—even if I die a few years from now—how do I want to spend the last few years of my life?”

As he pedaled, he reviewed the options. He could sit around alone, feeling sorry for himself, sullen and withdrawn, angry at the world, angry at God, jealous of all those people who don’t have cancer. Or he could get outside and bust his rear end with his friends. “To do hard things with a bunch of great men is what I like to do more than anything else,” he says, and by joining us for 50-50-50, he could model the exact kind of man and leader all of us aspire to be.

Even with all that, maybe the cancer will take him anyway.

“At least I’ll be happy,” he said. “Either way, it’s a win.”

As much of a beast as he is, as strong and tough and persistent as he is, that’s only a fraction of what I love and admire about him. If the cancer turns nasty, metastasizes, travels throughout his body, whatever, his resume of 50 marathons, his willingness to hike 50 miles, bike 50 miles and canoe 50 miles, his ability to do pushups until you get bored of counting them, won’t mean squat.

But his friendships will. The love he gives and takes will. They will live on.

The power of friends

Williams’ final radiation treatment came at 7 a.m. on a Tuesday, two days after 50-50-50. Before that appointment, he led a 5:30 a.m. workout at a site called The Dawg Pound near his home in suburban St. Louis. Yes, two days after 50-50-50 and an hour and a half before his last radiation treatment, he ran a workout.

A typical workout at The Dawg Pound draws eight men. Sixty-seven of us attended this one. We showed up to help Williams carry his burden, to make sure he knew he was not alone. He helped us share his suffering by dialing up a doozy of a workout, leading us through pushups, burpees, situps and more in sets of multiples of 44—the number of radiation treatments he endured.

Before he rushed off for his final treatment, he called the men into a circle around him. Our hearts were pounding and heavy. So was his. But it was also full to overflowing. He called it one of the best days of his life. He told me repeatedly how gratifying it was to see so many men heaving their chests alongside him. Other than from his family, he had never felt so loved.

He marveled at the change in his friendships since joining F3, in both quality and quantity. As he talked, his hands shook. He had written a beautiful speech, started to read it and spoke instead from his heart, which was even more beautiful. His voice cracked. Men to his right and left put their arms around him, and with their support, he stood tall. 

This article originally appeared in the March/April 2023 issue of SUCCESS magazine. Photo courtesy of John Urhahn.

The post The Power of Strong Friendships in Strengthening Well-Being appeared first on SUCCESS.

When she climbed off of that pitch one glorious Monday morning in July, Beck, one of the 2019 National Geographic “Adventurers of the Year,” was glowing with excitement. I asked about the joy splattered across her face.

“Climb it,” she said. “And then ask me again.” 

I stepped up to the wall. The first 8 feet were close to straight up, difficult for a beginner like me, even with obvious handholds. After that, the wall turned in a few degrees, still too steep to climb without ropes but not by much. I threw my right hand out, then my left foot, then left hand, then right foot, feeling like I imagine Spider-Man feels when he scales skyscrapers. I immediately understood Beck’s joy. 

In rock climbing, a sport sometimes defined by ambition driving out fear, Beck is always looking to finish the next pitch, add the next skill, conquer the next challenge. But she finds happiness, too, in climbing for the pure fun of it.

For Beck, climbing and the solopreneur life are both about finding balance. In climbing, that means pushing herself, adding more skills—and living to tell about it. In the work world, that means finding time for her variety of gigs, a list that has included speaking engagements, sponsor appearances and marketing for her former full-time employer. On top of that, she also has to climb, see her husband, take care of her animals, etc.

“I’m not one of those who [say] climbing makes me feel alive,” she says. “It reminds me of why I want to be alive.” 

Maureen Beck, a competitive paraclimbing athlete

In the opening to Stumped, a documentary about Beck’s ascent of Days of Future Passed, a climb rated as 5.12 (the stage at which good climbers become great), Beck attempts to look serious as she explains why she has only one hand (her left arm ends at her forearm). “Someone took the guard off the wood chipper,” she says, nodding solemnly. 

But she can’t maintain the ruse. She grins as she launches into a series of explanations, each more absurd than the last—meeting an alligator at a petting zoo and waving goodbye to a helicopter pilot among them.

The truth is, she was born that way. When she was a young girl, slights real and imagined drove her. She traces her beginning in rock climbing to a guide at a camp suggesting she sit out that activity. That pissed her off. Soon she was shimmying up every crag in Maine. She climbed passionately while in college, then set it aside somewhat to pursue a “normal” career.

That bored her. She moved to Colorado in 2012 and dived into the climbing scene there. Beck started working with Paradox sports as an instructor for adaptive athletes and entering paraclimbing competitions. She has won nine national titles and two gold medals at international competitions.

Many praise her, but she feels the adulation is misplaced.

With her growing presence in the climbing community has come adulation, much of it misplaced, she says. She feels “icky” when fans laud her for being inspiring because she is a one-handed rock climber. Being a one-handed rock climber does not make her inspiring, she says, it just makes her active, and simply being active is not inspiring. “Who wants to live their life on the couch?” she asks.

If she does something inspiring—such as when she climbed Days of Future Passed—she will accept the praise, though perhaps grudgingly. To get to the top of Days of Future Passed, she returned to it roughly 20 times over five months and climbed it three to 15 times per visit. She fell at the same point (called a crux) over and over again. When she finally reached the top, she looked half stunned, half relieved. She was sick of that wall and glad to be done with it.

I tried to ask about the resilience necessary to keep trying after failing more than 60 times. She brushed off the question. “That gives me way too much credit for having intent,” she says. “Maybe that’s what it is. Or I’m just too dumb to quit.”

For Maureen Beck, it’s about balance

Even now, with years of experience, Beck still has to convince her “monkey brain,” as she calls the intrinsic desire to stay alive, to climb. 

She keeps two ideas in tension. One is that the best climbing stories are about difficult and challenging pitches. Stumped would not have been worth watching (or making) if she climbed Days of Future Passed on the first try. The other is that an obsession with a can-do attitude can be mentally and emotionally toxic, to say nothing of being physically dangerous. 

Her rational brain tells her the ropes, carabiners and belay system are safe. Her monkey brain tells her that falling will hurt—maybe a lot—and why do we want to do this, anyway? “From the bottom, they all look scary,” she says.

This article originally appeared in the March/April 2021 issue of SUCCESS magazine and has been updated. Photos by © Daniel Gajda.

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“Turn in the story” is the single most important task I have as a freelance journalist. If I can’t turn in stories, my business ceases to exist, which made this a problem I needed to solve, immediately.

As my wife and kids slept, I exited the trailer and paced a rut in the dirt as I thought through solutions. I could drive to a local coffee shop and file from there. For that, I’d have to wait more than an hour for it to open. Until then, I decided I might as well take a walk and hope I found cell service. I was pretty sure I was in one of those very small, unpredictable and massively annoying blank spots in coverage. How small, I soon found out. I walked with my phone in my right hand and my laptop in my left. After 60 steps, the phone found coverage, the hot spot fired up and the internet on my laptop sprang to life.

I froze, worried if I took one more step I’d lose coverage again. I found out later I was right. But for now, I had full connectivity. I sat on the gravel road and crafted an email. I heard the pitter-patter of woodland creatures hustling across the forest floor. Somewhere in the distance, a woodpecker hammered its face into a tree. I grinned at this unique setting, attached the story and hit send.

It sounds funny now, but it was a pain in my gravel-covered butt then—not so much because I had to take 60 steps to file a story, but because the lack of connectivity in the trailer meant my wife and I wouldn’t be able to work.

We had planned an eight-day jaunt to Wisconsin and Michigan as a “bleisure trip”—a way to mix work and fun. I planned to write. She’s a lawyer and planned to spend several hours each day researching and writing in the RV and the rest of the time with me and our kids hiking and kayaking and taste-testing gelato across Door County, Wisconsin.

Our best-laid plans fizzled out on the first morning, and the lack of connectivity turned out to be only the beginning of our “troubles.” In Crossman family lore, this eight-day bleisure trip will go down as The Vacation of Whiplash.

I’ll get to that in a second. First, I need to answer a question you’re surely asking: What in the hell is a bleisure trip?

Bleisure is a made-up word smushing together business and leisure. Now that we’re in the middle of this trend, it seems inevitable: More and more people are realizing working remotely gives them the freedom to work wherever they want, whether it’s their office, a coffee shop at the bottom of a ski slope or a gravel road in Wisconsin.

Think of it like becoming a short-term digital nomad—you adopt a more “YOLO” way of living and working, while retaining the comforts of a home to return to. This is #VanLife for people who don’t want to spend their whole lives on the road… yet.

Bleisure trips have been growing since the pandemic, while business travel has simultaneously decreased. In its 2022 travel outlook, Deloitte said it expects both trends to continue: “They should be treated as new but lasting components of travel’s structural reality.”

I used two apps to make our bleisure trip to Wisconsin easier to arrange. One is called Outdoorsy, through which you can rent someone’s camper, trailer, motor home, etc. (Outdoorsy comped my RV alongside the gravel road in Wisconsin and another at an alpaca farm in Michigan.) The other is Harvest Hosts, a membership-based network of unique campsites such as museums, wineries, farms, etc. I paid a yearly fee and now can camp at more than 4,000 locations for free. That number is nearly quadruple what it was when I first discovered the app in mid-2020 (1,046).

Jennifer Young, co-founder and CMO of Outdoorsy, said reservations slowed to zero at the beginning of the pandemic and exploded as the world reopened. Their reservations grew for many reasons. The emergence of bleisure trips is one of them, as more people recognize RV travel as a way to take advantage of the freedom of remote work while also exploring the outdoors. “What we’re seeing is a more blended approach for how they might relocate for a month at a time or plan their life on the road and figure out how they work in that period of time,” Young says.

I’ve been taking bleisure trips since before the word existed, including to Columbus, Ohio (twice); Branson, Missouri (also twice); Des Moines, Iowa; Colorado; and Michigan (many times). All of those trips went fine, many of them went great.

Our trip to Wisconsin did not.

We kept laughing: Every time we left the trailer to explore Door County, we had a blast—kayaking in Lake Michigan, skipping rocks in it, hiking alongside it, visiting a lighthouse on its banks—and every time we returned to the trailer, something went wrong.

In addition to the internet problems, water backed up into the shower (my fault; it’s easy to drain, but I didn’t check the level). I shattered the glass cover on a stove (my fault again; I didn’t know I was supposed to lift the cover before I turned on the stove, and the glass exploded because of the heat). And a dog pissed on my backpack.

Right in front of me!

He just lifted his leg and let loose!

I’m just relieved I wasn’t wearing it at the time.

One morning, I exited the trailer to go for a “problem-solving” run along an isolated road lined by green fields. I planned to spend that time thinking through what to tell you about The Vacation of Whiplash. How would I write about the challenges of bleisure trips without understating them and making it seem easy—or overstating them and talking you out of trying it? As I worked to solve that problem, a greater truth about bleisure trips revealed itself.

My feet pounded the soft grass as I noodled on a paragraph that started like this: You’ll have the same problems as you would during a regular workday or a regular vacation, and it’s how you overcome them that determines how…

A fluff of brown movement grabbed my attention. I stopped running, looked to my right and watched four deer play their version of leapfrog. I’ve seen thousands of deer, but I’ve never seen them do that. By the time they scampered into the forest, I had forgotten about the internet, the shower, the dog.

Anyway, what was I talking about before I got distracted? Oh, yeah: Problems are inevitable on bleisure trips. Your phone won’t work, the museum will be closed, traffic jams will make you miss your reservations.

But magic and inspiration will arise when you least expect them, too. Young made a stirring case for toggling between a recreational adventure life and work life, and that the former will make the latter better, even if—especially if—a dog pisses on your backpack.

“You’re really leveling up your life, because you’re realizing the benefits that Mother Nature affords you that there’s no way any office—whether it’s your home office or work office—could ever provide,” Young says. “Your productivity is better, your anxiety is low, you’re inspired by life. You’re grateful for the opportunity to be able to flex a little bit in and out of it. Not to mention the cumulative benefits of just being more active.”

My family treasures these Whiplash memories; even as they were annoying us, we knew they made the trip special in a way it wouldn’t be without them.

If given a choice, I’d rather file a story sitting on my butt on a gravel road then sitting at my desk in my home office. Having said that, if a dog never pissed on my backpack again, I’d be good with it. 

This article originally appeared in the January/February 2023 Issue of SUCCESS magazine.

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