In his book Excellent Sheep, William Deresiewicz describes the current generation of strivers as “driven to achieve without knowing why.” And then they become paralyzed when they’re not sure how to proceed.
I jokingly call the hang-ups associated with a drive to achieve as “the Achievement Demons.” When I was growing up, I’d study for days trying to get good grades. When I’d get an “A,” I’d feel elation for about 30 seconds, and then a feeling of emptiness. Rinse and repeat.
What does achievement look like today? A generation ago, the path was clearer. Become a doctor or a lawyer or a professor (or, in the past 20 years, a banker or a consultant). Join an established company and climb the ladder. But now, the legal profession is shrinking, and under extreme pressure. Academics vastly outnumber tenure track positions, and research funding is down. Doctors complain about how practicing medicine is not what it used to be due to increased regulation and market pressures. Large companies are often contracting due to technological threats even as they are experiencing steady growth.
After graduating from Brown, I went to law school and became a corporate lawyer in New York City. I probably looked pretty conventionally successful as a 24-year-old getting paid $125,000 a year, plus bonus, wearing suits, and living in a Manhattan apartment. But I hated my job, I didn’t admire the people I was working with, and I felt that I was becoming a smaller, less imaginative, less risk-taking, less likable version of myself.
My quest for significance took the form of co-founding an internet company that didn’t work out. In 2001, when the internet bubble burst, my company went out with the tide. That failure was difficult to grapple with.
I went to work for another startup that ran out of money, and then another startup that made software for hospitals. Investors included David Bonderman, the billionaire co-founder of TPG, and Rajat Gupta, the former head of McKinsey (now disgraced for leaking insider information to a hedge fund as a director of Goldman Sachs). I told myself that we were on our way.
I was there for four years, and it turned out we weren’t on our way. Depending on how you counted, this was my third job at a failed company in a row. I was 30, and at that point my confidence had been through the wringer. I felt like my career had stalled. My peers from law school were making substantially more money than I was—they were literally having dinner and birthday parties that I couldn’t afford to attend.
It was around this time that I was approached by Zeke Vanderhoek to become his partner at a test-prep company, Manhattan GMAT. The operation was quite small—a full-time team of six people. It was an unglamorous industry—test prep didn’t have the same ceiling or sense of possibility as a venture-backed healthcare software company. I’d started at Manhattan GMAT as a part-time employee to pay the bills. Now I was going to devote my career to it. You couldn’t spin that at a party.
It turned out to be the best professional decision of my life, in part because I let a lot of stuff go. This was a company where trying to network was of very limited utility, so I kind of gave up on it. I just hunkered down and did whatever I could to make the company grow. The first couple of years, I’d say I worked at Manhattan GMAT and no one would know what I was talking about. But the company kept growing and growing. We eventually became number-one in enrollments in the US. Then, every once in a while someone would say, “I know that company!”
I’d say it took me about seven years after leaving the law firm to let the demons go—to not feel like I was always falling behind my own expectations, or what my peers were doing, or what my parents thought, or my own supposed potential; to view my time intrinsically, as well as instrumentally. And this was the point at which I was able to meaningfully contribute to the success of an organization (and form healthy relationships), in large part because I was more at ease with myself and others.
I’ve learned my demons aren’t just mine. Thousands of young people share the same thirst to achieve that I had (and still have)—rising out of family pressures, alienation, and an identity that they’re smart or talented or special or destined to do something significant. On the plus side, it can make them hard-charging, industrious, and willing to put themselves out there. On the flip side, it can be paralyzing. It can lead to depression, a sense of isolation, even self-destruction. I think it’s harder in an era of social media, where there’s always something you’re missing. FOMO (fear of missing out) is the enemy of valuing your own time.
“I feel this constant pressure to make something of myself,” relates one young person, who now works at a startup after interning at an investment bank. “Even during celebrations, it’s like we’re all plotting the next competition. My friends have a ton of ambition and no clear place to channel it. I get the sense that we’re all trading happiness to run a little faster, even if we’re not sure where.”
There’s a progression from aspiring young man or woman, eager to make a mark, to integrated builder who can hunker down and operate for years. It’s as much a journey of the spirit, about discovering one’s identity and values, as it is a professional challenge. And it doesn’t really end.
I spend time with hundreds of recent college graduates who are facing this struggle, and there’s no easy answer. Again, it’s personal and different people will engage with how best to use their time in different ways.
These are a few things that have made the journey a little bit easier for me:
The demons are strongest when you compare yourself to others who seem to have it all figured out. They’re climbing the ranks and making progress, maybe getting an advanced degree, living in New York or San Francisco, where the heights of achievement reach to the sky. You have classmates whom you feel you’re just as good as.
Then you spend time reconnecting with someone you grew up with, and you get a completely different perspective. Or you spend time on a hike in the country, and it all seems grossly irrelevant. Or, you extract yourself to a new place—say Detroit, or New Orleans, or Baltimore—where you’re exposed to people who wouldn’t understand the distinctions between you and your classmates anyway.
It’s tempting to put a brave face forward when you talk to people, especially if you’re in hustle mode. But sometimes letting someone in on your struggle allows you to form a much more meaningful connection with them. Particularly if, as is the case 95% of the time, others are going through similar things.
Trust me when I say that people who seem to have it great have their own struggles.
There are some people that value you for you, not what you can do for them. Identify the people you can keep it real with, and make the most of them.
My parents were concerned and unhappy when I left law. They didn’t talk too much about me to their friends—and I think they still told people I was a lawyer.
Eventually though, they came around. Parents will, most of the time, get on board with your choices if they see that you’re committed to them and willing to work hard. It’s particularly true if you make time for them, and they feel like you’re becoming a decent person. (Hopefully this is the case more often than not.) As much as they want to be able to talk about you, they want a good relationship with you even more.
Keep working on them, and don’t give up.
We’re all much more than a list of achievements. It’s the things we do in our personal lives that make us who we are.
I’ve been to dozens of weddings in the past 10 years (including my own), and have heard countless stories about people from their friends and loved ones. I’d say between zero and 1% of those stories took place in an office.
What we do with our working lives is important. But not every day (or week, or month) is intended to move the ball forward. Sometimes we’re just cooking, or writing our cousins, or putting together a collage that only one person will see. Those days are important too.
The single biggest thing you can do to feel good about your direction in life is to find the right opportunity, one in which you’re building toward something. As Graham Weston, the co-founder of Rackspace, put it, “What we all want from work is to be valued members of a winning team on an inspiring mission.”
This is much easier said than done. Quality opportunities that lead to a better sense of self are vastly outnumbered by positions that require significant compromise. Often, you’re in an environment that develops you in certain ways, but isn’t a long-term fit.
It’s always a tough balance—no job is going to be perfect. But be positive and keep pushing in the right direction. By the fourth or fifth job or company, you’ll have a much better sense of where you’ll best be able to develop and contribute. Maybe you’ll even start your own thing.
Early on, you think that leadership comes from seniority. But it’s actually just an activity, and something you can do at any point.
Even as you’re trying to make your manager happy, find something that you can be in charge of and run with it. It can be something at work, like a committee or activity. It can be modest and personal, like a book club or pick-up basketball game. It can be a volunteer opportunity for a local non-profit. It can be a side business or project. It doesn’t need to be big—it just needs to be yours.
You’ll find that being in charge forces you to use different muscles and capacities than is the case in other environments. At West Point, they ask cadets to lead and report to a different cadet each year. That way, by the time they graduate, they’ll have a range of different leadership experiences to draw on.
I started a party business while I was working at the healthcare software company. It turned out to be a great experience. I also taught the GMAT part-time. And that morphed into my career for five-plus years.
What if I told you that you could jump into someone else’s head and experience any point in time in human history? And learn literally from the smartest people who ever lived? That’s sort of what reading is like. It’s a context-switch in its own right. You can learn about business today from Jim Collins, or Sheryl Sandberg, or Eric Ries. You can read about the life and times of Steve Jobs, or Tina Fey, or Abe Lincoln. You can get a different take on life and the world with Murakami, or Kundera, or Woolf. You can grapple with ideas from some of the best thinkers in history. Books impact your mind like a boulder in a pond. Then the boulder stays there.
Putting your body in motion is just as important. Exercise relieves stress and helps you stay vital. Countless studies have shown it’s just about the best thing you can do for your long-term wellbeing. On a bad day, you can always say to yourself, “Well, if I accomplished nothing else, at least I went to the gym, or to the yoga studio, or for a run.”
The struggles are different and achievement means different things as time passes. The demons evolve as you grow. You can’t outpace them – but you can weaken them and make them harder to hear.