Are You Working For Or Against Yourself?

Sometimes it’s easier to understand our methods by hearing a few stories. Here we wanted to showcase two former clients of ours: Tom and Jerry (pseudonyms). What’s interesting is that both of these men were highly successful in their respective industries. From the outside, both looked like they had absolutely everything going for them. Inside, they both felt completely miserable and totally lost. Here’s how we helped.


The Natural & the Rainmaker 

Tom came had always excelled at sports: hitting homers in T-ball, popping wheelies in training wheels, and hiking some twenty miles a day in the rural brush land beyond his suburban town. By middle school, Tom’s parents had pushed him to baseball, their eyes set on the pros. Sure enough, he was drafted out of high school third overall in the MLB draft—a stunning achievement. After working his way through the minors, he landed in the majors where he stuck around: He played for 10 years in the league and at 37 years old he was financially set for life.

So what could Tom possibly need our help for? The problem was that he was adrift. He’d stepped away from the single thing that had defined his personal and professional life, and now he had no idea what he was, where he should go, or who he should be.

A friend and former player lured him into the investment business, but after a few months Tom left, unmotivated by the money or the company’s values. Tom’s wife urged him to enroll in college, but Tom struggled with the daily requirements and couldn’t stand the discomfort of studying all day in a library. He left after two semesters. Another friend lured him to play on his soccer team. At first, Tom felt like he’d finally found his next career, until the second week of playing when he suffered an ankle injury that put him out for months, and then a knee injury in rehab. His body just wasn’t up to that kind of work anymore.

He’d stepped away from the single thing that had defined his personal and professional life, and now he had no idea what he was, where he should go, or who he should be.

Jerry, on the other hand, was far from an Adonis. The middle of three children from the suburban Midwest, he had all the hallmarks of the family wallflower, stuck between an overachieving older brother and his perennially popular younger one. Through most of his adolescence Jerry felt invisible, rarely excelling in or out of the classroom. As he put it, his “senior superlative” would’ve been: “Most likely to be average.”

Rejected by the family’s alma matter, Jerry enrolled in a big state university where, just as before, he struggled to stay motivated. It wasn’t until he stumbled into a required computer science course that Jerry discovered that he had a real knack for working with coding languages and massive amounts of data. He loved the idea that he could solve big questions with creatively engineered answers. He flourished in computer science, graduating college with honors and landing in a summer internship at a big time financial firm. Jerry had somehow tripped his way into brilliance.

About a year-and-a-half into his first job, Jerry built a particularly elegant—and profitable—algorithm that brought the attention of the firm’s higher-ups. Pretty soon Jerry’s career exploded. Several big hedge funds sought him out and, eventually, one wooed him away. He was a savant at understanding the tools, crunching the numbers, analyzing the data, and picking winners. At this new hedge fund, his career continued to pick up steam. The organization trusted his skills and judgement, and rewarded him with promotion after promotion. Soon enough, Jerry was on the senior leadership team.

 So what was Jerry’s issue exactly? The problem was that amidst all the success, Jerry’s mental health was sinking fast. He’d been white-knuckling it for the last two years, he said, exhausted by the frantic pace of work, and anxious about his newfound prominence in the firm. But, even more importantly, he wasn’t enjoying himself like he used to. Wealthy and successful beyond his wildest dreams, Jerry was totally lost.

Scribes from Meketre's Model Granary, ca. 1981–1975 B.C.

Tom and Jerry were both prime examples of the kinds of challenges we like to solve. For every client who comes to us at the beginning of their next move, we work with just as many who walk through the door after carrying the weight of their success and misery side-by-side. They know that they’re stuck but feel guilty for even contemplating a change. How could they? Isn’t this what they wanted?


Welcome to Jellystone, Tom

The first step is to let go of expectations, attachments, and unhealthy limits. And then to start asking honest questions and listening. That’s where we started with Tom.

After several sessions of listening, discovery, brainstorming, and feedback, things broke open after we asked Tom a simple question: describe his ideal day without using nouns. Which is to say: don’t tell us the things you want to do, tell us the feelings and actions you want to experience. He got this one. He said that he’d love to do something physical, preferably outdoors, potentially with a sense of teamwork like he felt in his playing days, while feeling challenged but also free to set his own course.

The answer was obvious. He had he ever thought about becoming a park ranger?

At first, he was baffled. All of his friends—mostly his former teammates—were doing media appearances or running private equity firms with all the cache they’d built. Why not him? And he didn’t know a single thing about nature conservancy. Also what would happen when he invariably got recognized on the job? Plus, what kind of challenge was this?  

We expected his skepticism. It’s the same kind of knee-jerk reaction many people have when a new idea challenges their worldview. Change is always hard. The natural reaction for many is resistance. But that’s why we’re here. We walked him through his excuses, showing him how different they were from the wish list of career traits he had just set down. He never said that he wanted to follow what other ex-athletes did—actually his track record there was proof of that. Why should he feel embarrassed about the work? And he told us that he wanted a challenge. This was it.

It would be a physical job and outside: both things we sensed were important to him based on his revulsion to office work and his childhood spent lost in nature. He’d have a new team, so to speak, of rangers and conservationists that he’d be working with. And based on his experiences at his friend’s investment firm, he had told us how much his values mattered to him, even if he didn’t see himself as a warrior for social causes. Most importantly, for a man who loved excelling at things, this was an entirely new arena that required all the kind of dedication and patience he’d mastered over his career.

At first, the transition was a little too easy. Arizona, where Tom lived, had dozens of great state and national parks. We helped him connect with a park administrator and sit down for coffee. The administration was naturally ecstatic to speak with a local sports hero. They asked for his help in hosting a fundraiser with a local nonprofit to draw donations to the park. Tom agreed. And then he was thrust right back into press engagements and office work—the very thing he was trying to leave behind. Was this what he really wanted?

Of course, it wasn’t. Instead of pushing for and pursuing the kind of path that we’d designed together in our coaching sessions, he’d allowed himself to fall into old habits and be dictated by the patterns and desires of others. With our coaching he went back to the state park offices and explained exactly what he wanted: to be a docent, working the trail, guiding tours—all of it.

At first they were baffled. But that would require him to attend their six-month training course, they said. And then he would have to enter a three-year apprentice program before he could be properly trained and certified. Surely Tom didn’t want to waste his time doing that—not for a millionaire athlete. They could use his celebrity elsewhere. But Tom held fast. Yes, that’s what he wanted to do.

While that looked like the obvious, easy, and seemingly attractive route, it wasn’t the route that would bring him the most joy, satisfaction, and meaning. Two weeks later he was dressed in khaki ready for his first day of training.

Tom explained that it wasn’t until the second week, when he was out on the trail hauling fence posts on the mesa, that it all clicked. He’d driven home that day feeling more satisfied than he had in years—maybe ever. For the first time in his life, he’d thrown his body around, felt invigorated by his time outside, and yet could go to sleep without the nagging dread of the next game, or the next roster move. Last we spoke, Tom had finished his second year in the apprentice program. He had built a close connection with his cohort of apprentices, and he was outside basking in nature and enjoying every second of it. He’d come to realize that there was such thing as a real challenge without competition. 

While that looked like the obvious, easy, and seemingly attractive route, it wasn’t the route that would bring him the most joy, satisfaction, and meaning. Two weeks later he was dressed in khaki ready for his first day of training.

Getting That Big Demotion

 For workaholic Jerry, our suggestion was both simple and difficult: we recommended that he demote himself. We didn’t want him to quit working—not at all. We just believed that he should stop doing the things that stressed and exhausted him so he could focus on the things that he does easily and well.

In our practice, we’ve found that this is a particularly common problem in corporate America. The most talented employees are often promoted because of their performance in a specific role into management and leadership roles they’re woefully unprepared for. Pretty soon they’re spending most of their time in budgeting, resourcing, mentoring, adjudicating workplace issues, and selling their team to board members and stakeholders—basically nothing that they had previously been trained for, and often things they’ve never been good at. That is why so many organizations are staffed with overly stressed, or incompetent managers and leaders: they’re picking for the wrong attributes.

Jerry is one of those clients who had unwittingly worked his way out of what he loved into what he doesn’t love. It’s not that he can’t do the tasks of his current position; rather, it’s that those tasks “cost” too much in terms of his mental, physical, and emotional health.

Stepping back meant stepping away. It was initially very hard for Jerry. No one really believed him when he said that he wanted to go back to his old job behind a computer. And even though he nominally did, senior leaders kept coming to him with questions and problems and needs relative to the role that he was trying so hard to leave behind. “Can you please meet with so-and-so?” “Can you help me with this management plan?” “Do you have some time after work today, I need bounce some ideas off of you?” The floodgates were open because they’d never been closed.

It was hard for Jerry to set the boundaries necessary to redefine his new role in the company. To his coworkers, he was still Jerry. He still possessed all of the traits and experience that they’d relied on in his old role. Why should anyone struggle when Jerry was so good at these things? Well the answer was that those tasks were also killing Jerry slowly on the inside. We reminded him that just because he’s good at something doesn’t mean it’s what he should be doing.  

With our coaching and consistent support, Jerry got back to where he’d started. And, today, his goal is to stay where he is, to do what he does easily, quickly, and well. And to minimize the stress and exhaustion of work.

Tallying the Costs

Tom and Jerry’s cases show the clear benefits of thinking about “costs” when it comes to building your career. One central tool we stress is recognizing the difference between the many things that you do well because you’ve practiced at them to become proficient, and the many things you do that have always come naturally to you. 

The first is what we call a “high cost” talent, and the second is “low cost.” “High cost” talents require your constant practice and attention to maintain. Make no mistake, you can absolutely be a master at a “high cost” talent, but they still require a great amount of effort—and personal stress—to execute well. On the other hand, “low cost” talents come naturally, feel familiar, and regardless of how hard you’re working at it, feel inherently less stressful.

Tom is a naturally physically talented person. His well-honed strength, coordination, endurance, and vitality allow him to master almost any physical tasks put in front of him with high levels of performance. These are “low cost” talents because when he’s outside, breaking a sweat, feeling his body in space, he’s expending tremendous energy and concentration, but it comes effortlessly to him. That’s why we believed he’d thrive in his new position at a national park: instead of fighting against what brought him joy with ease, we helped him find another vocation that would benefit just as much from his natural abilities—in addition to feeding into his personal interests, values, and style.

This is perhaps one of the biggest things any career seeker should understand. Just because you’re good at something doesn’t mean that it’s good for you.

On the surface, Jerry’s story may look similar, but it’s quite the opposite. Jerry had effectively promoted himself out of the things he does easily, quickly, and well and into a role that required tremendous daily effort for him to excel at—which he did. His natural, “low cost” talents in research, logic, and creative problem-solving all built the foundations of his successful career.  But when he moved up to the top floor, he found that his days were now primarily spent in logistics, public speaking, social networking, and human psychology. Though he would eventually become good at these new job requirements, they came with a tremendous cost.

This is perhaps one of the biggest things any career seeker should understand. Just because you’re good at something doesn’t mean that it’s good for you.

Often we work with clients who pay too big a price for what they do. That cost may show in physical ailments, mental health crises, or in damaged personal relationships. But because you’re bringing in promotions, bonuses, or other measures of external success you wonder why you’re feeling so unfulfilled. What’s there to be stressed about? You just got the big raise.

It’s not whether you can or you can’t do something. Anyone feeling lost or adrift would do much better if they thought about what parts of their current lives and jobs seem to cost less and which parts seem to cost a great deal more to them. That’s where the benefits are.


We help people build careers
around their true selves.
For real.

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