In which I introduce the second control trap, which warns that once you have enough career capital to acquire more control in your working life, you have become valuable enough to your employer that they will fight your efforts to gain more autonomy.
Lulu Young is a software developer and she loves what she does. She lives in Roslindale, a close-in suburb of Boston, in a beautifully renovated duplex. When I met her there on a rainy spring day in 2011 to talk about work and control, she needed little prompting before diving into one of the more detailed autobiographies I had so far encountered in my quest. I can tell you, for example, that she scored a 5 on her AP chemistry test in high school and that landing her first job involved a chance encounter with an old employer at a Bertucci’s in Wellesley Hills. Here’s what I wrote in my notes not long into the interview: “This is someone who has put a lot of thought into her career.”
This thoughtfulness evidently paid off, as Lulu turned out to be one of the more confident and contented subjects I have encountered in my interviews. At the core of this contentment is control. Throughout her career, Lulu repeatedly fought to gain more freedom in her working life, sometimes to the shock or dismay of her employers or friends. “People tell me that I don’t do things the way other people do,” Lulu said. “But I tell them, ‘I’m not other people.’ ”
She succeeded in these fights, as you’ll learn, because she was wary of the first control trap, which was described in the previous chapter. That is, she was careful to ensure she always had enough career capital to back her up before she made a bid for more control. This is a major reason that I want to tell her story: She provides a great example of control done right.
Lulu’s first job after graduating Wellesley College with a mathematics degree was at the bottom rung of the software-development career ladder: She was working in Quality Assurance (QA), a fancy term for software tester.
“So your job would be, for example, to put text in bold and then make sure it worked?” I asked her, as she explained this first job. “Whoa, whoa, let’s not exaggerate the amount of responsibility they gave me!” she joked in response.
This was not a great job. In fact, this was not even a decent job. It’s here that Lulu could have easily fallen into the first control trap: Finding yourself stuck in a boring job is exactly the point where breaking away to pave your own non-conformist path becomes tempting. Instead, she decided to acquire the career capital required to get somewhere better.
Things played out as follows: Lulu began hacking the UNIX operating system that ran the company’s software. She eventually taught herself to build scripts that automated the testing, thus saving the company time and money. Her innovations attracted notice, and after a few short years she was promoted to senior QA engineer.
By this point, Lulu had built up a legitimate store of career capital, so she decided to see what it could buy her. To regain some autonomy from a succession of micromanaging bosses who had been tormenting her, she demanded a thirty-hour-a-week schedule so she could pursue a part-time degree in philosophy from Tufts. “I would have asked for less time, but thirty was the minimum for which you could still receive full benefits,” she explained. If Lulu had tried this during her first year of employment, her bosses would have laughed and probably offered her instead a “zero-hour-a-week schedule,” but by the time she had become a senior engineer and was leading their testing automation efforts, they really couldn’t say no.
After she earned her degree, Lulu quit the company and brought her QA automation skills to a nearby start-up that had just been acquired by a major firm. “I had this spacious office with three computer screens,” she recalls. “Every week the office manager would come by to take our candy order. You would tell her what candy you wanted, and it would show up on your desk…. I had a lot of fun.”
After several years, the parent company of the start-up decided to shut down the Boston-area office, so Lulu, who had just bought a house, decided it was time for something different. When she reentered the job market, she generated several offers, including one to manage the QA group for a large company. This would have been a big promotion for Lulu: more money, more power, and more prestige; the next step on a ladder to becoming a hot-shot executive VP.
Lulu turned it down. Instead, she took an offer to work with a seven-person start-up, founded by an old college friend’s boyfriend, that had jumped at the chance to acquire someone with such proven skills. “I didn’t really understand what they did, and I’m not sure they had it all figured out yet either,” she told me. But this is exactly what made it appealing to Lulu: tackling something brand-new, where there wasn’t a detailed plan in place already, seemed interesting—a pursuit where she would have a lot of say over what she did and how she did it.
By the time this company was acquired in 2001, Lulu was the head software developer. Given this career capital, when she began to chafe at the new owner’s regulations—a dress code, for example, plus insisting that all employees work between the hours of nine and five—she was able to demand (and receive) three months’ leave. “There will be no way for you to contact me during this period,” she told her new bosses. The leave, it turned out, was also an excuse to train her staff to work without her. Soon after her leave ended, Lulu left and, in a bid for even more control, became a freelance software developer. At this point her skills were so valuable that finding clients was no problem. More importantly, working as a contractor also gave her extreme flexibility in how she did her work. She would travel for three or four weeks at a time when she felt like getting away. “If the weather was nice on a Friday,” she told me, “I would just take the day off to go flying” (she obtained her pilot’s license around this time). When she started work and when she ended her days were up to her. “A lot of those days I would take a niece or nephew and have fun. I went to the children’s museum and zoo probably more than anybody else in the city,” she recalls. “They couldn’t stop me from doing these things, as I was just a contractor.”
I interviewed Lulu early on a weekday afternoon, and the timing didn’t seem to matter at all. “Hold on, let me make sure Skype is turned off so no one can bother me,” she told me soon after I arrived. Taking an afternoon off on a whim to do an interview is not the type of decision she could have gotten away with if she had followed a traditional career path to become a stock-owning, Porsche-driving, ulcer-suffering VP. But then again, stock-owning, Porsche-driving, ulcer-suffering VPs probably enjoy their lives quite a bit less than Lulu.
Lulu’s story, as I mentioned earlier, is an example of control done right. Like Ryan and Sarah of Red Fire Farms, her career is compelling because she has infused it with control over what she does and how she does it. Also like Ryan and Sarah, she succeeds in this effort where others have failed—for example, Jane from the last chapter—by always making sure she has the career capital needed to obtain this autonomy.
Lurking in this story, however, is a hidden danger. Though Lulu’s career was satisfyingly self-directed, the path to acquiring this freedom generated conflict. Almost every time she invested her career capital to obtain the most control, she also encountered resistance. When she leveraged her value to obtain a thirty-hour schedule at her first job, for example, her employer couldn’t say no (she was saving them too much money), but they didn’t like it. It took nerve on Lulu’s part to push through that demand. Similarly, when she turned down a major promotion to take an ill-defined position at a seven-person start-up, people in her life didn’t understand.
“You had just bought a house,” I reminded her. “To turn down a big important job to go work with an unknown little company, that’s a big deal.”
“People thought I was nuts,” she agreed. Leaving this start-up after it was acquired was similarly difficult. Lulu was hesitant to get into details, but the subtext was that her value was so high at this company that its new owners tried every tactic they could to keep her on board. And finally, her transition to freelance work came with its own difficulties. Her first client really wanted to hire her full-time to work on the project, but she refused. “They really didn’t want a contractor,” she recalls, “but they didn’t have anyone else who could do this type of work, so they eventually had no choice but to agree.”
The more I met people who successfully deployed control in their career, the more I heard similar tales of resistance from their employers, friends, and families. Another example is someone I’ll call Lewis, who is a resident in a well-known combined plastic surgery program, which is arguably the most competitive medical residency. Three years into his residency, he was starting to chafe under hospital bureaucracy. When I met him for coffee, he gave me a vivid example of the frustrations of life as a modern doctor.
“I once received this patient in the ER who had his chest cut open because he had been stabbed in the heart,” he told me. “I’m on the gurney, massaging his heart with my hands as he’s brought into the operating room. We get to the room, and obviously this guy needs a blood transfusion because he has a hole in his heart.
“ ‘We can’t give it to you,’ the tech replied. ‘You skipped registration when you came in’—remember, I literally had this guy’s heart in my hand when we came through the door—and I was thinking, ‘You got to be freaking kidding me.’ ”
That patient died in the OR. He probably would still have died even if he had been given a blood transfusion, but the point is that this was exactly the type of autonomy-demolishing experience that was eating away at Lewis. He craved more control in his life, so he did something unexpected: He took two years off from his residency program to start a company that builds online medical education tools.
When you ask Lewis why he wanted to start a company, he paints a compelling picture. “One thing a lot of people struggle with in my field is that they have a lot of ideas, but don’t know how to get them turned into reality.” In his vision, he would become a doctor, but also be the cofounder of this company that would continue to run without requiring his day-to-day supervision. As he came up with ideas around medical education, an interest of his, he could then hand them over to the team at the company to be turned into reality.
“Let’s say I have this idea for a game that could help premed students learn some sort of new concept,” he told me when I asked for an example. “I could turn to my team at the company and say, ‘Go make this happen.’ ” To Lewis, there’s a great sense of satisfaction in “creating something that actually works,” and this company would provide him that opportunity.
As with Lulu, however, once Lewis had enough medical expertise to successfully raise the funding to begin this company, he had become valuable enough to his employer that they didn’t want to let him go. He was the first person in the ten-year history of his combined plastic surgery program to request time off in the middle of his residency. “They were asking me, ‘Why would you do this!?’ ” he recalls. It was not an easy transition to make. When I met Lewis, however, his two-year break was almost up. During this time, his company had progressed from an idea into a well-funded organization with a popular flagship product (a tool that helps med students prepare for their board exams) and a full-time staff that will keep things rolling as he returns to finish his residency. Lewis was clearly happy about his decision to push for something different—but it hadn’t been easy.
This is the irony of control. When no one cares what you do with your working life, you probably don’t have enough career capital to do anything interesting. But once you do have this capital, as Lulu and Lewis discovered, you’ve become valuable enough that your employer will resist your efforts. This is what I came to think of as the second control trap:
The Second Control Trap
The point at which you have acquired enough career capital to get meaningful control over your working life is exactly the point when you’ve become valuable enough to your current employer that they will try to prevent you from making the change.
On reflection, this second trap makes sense. Acquiring more control in your working life is something that benefits you but likely has no direct benefit to your employer. Downshifting to a thirty-hour-per-week schedule, for example, provided Lulu freedom from a working environment that had felt increasingly stifling. But from the point of view of her employer, it was simply lost productivity. In other words, in most jobs you should expect your employer to resist your move toward more control; they have every incentive to try to convince you to reinvest your career capital back into your career at their company, obtaining more money and prestige instead of more control, and this can be a hard argument to resist.
Back in Rule #2, I was dismissive of the “courage culture.” This was my term for the growing number of authors and online commentators who promote the idea that the only thing standing between you and a dream job is building the courage to step off the expected path. I argued that it was this courage culture that led Lisa Feuer to quit her corporate job to chase an ill-fated yoga venture. This culture also plays a big role in egging on the less successful members of the lifestyle-design community.
In light of the second control trap, I need to moderate my previous disdain. Courage is not irrelevant to creating work you love. Lulu and Lewis, as we now understand, required quite a bit of courage to ignore the resistance generated by this trap. The key, it seems, is to know when the time is right to become courageous in your career decisions. Get this timing right, and a fantastic working life awaits you, but get it wrong by tripping the first control trap in a premature bid for autonomy, and disaster lurks. The fault of the courage culture, therefore, is not its underlying message that courage is good, but its severe underestimation of the complexity involved in deploying this boldness in a useful way.
Imagine, for example, that you come up with an idea for injecting more control into your career. As I argued earlier, this is an idea worth paying attention to because control is so powerful in transforming your working life that I call it the dream-job elixir. Also imagine, however, that as you toy with this idea, people in your life start offering resistance. What’s the right thing to do? The two control traps make this a hard question to answer.
It’s possible that you don’t have enough career capital to back up this bid for more control. That is, you’re about to fall into the first control trap. In this case, you should heed the resistance and shelve the idea. At the same time, however, it’s possible that you have plenty of career capital, and this resistance is being generated exactly because you’re so valuable. That is, you’ve fallen into the second control trap. In this case, you should ignore the resistance and pursue the idea. This, of course, is the problem with control: Both scenarios feel the same, but the right response is different in each.
By this point in my quest, I’ve encountered enough stories of control going both right and wrong to know that this conundrum is serious—perhaps one of the single most difficult obstacles facing us in our quest for work we love. The cheery slogans of the courage culture are obviously too crude to guide us through this tricky territory. We need a more nuanced heuristic, something that could make clear exactly what brand of control trap you’re facing. As you’ll learn next, I ended up discovering this solution in the habits of an iconoclastic entrepreneur, someone who has elevated living his life by his own rules to an art form.