Be more ambitious!

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I once worked with a guy who we’ll call Sam. Sam went to an elite manhattan private school for high school and one of the less-prestigious Ivy’s for undergrad. After college Sam went to work at Goldman Sachs. Unfortunately for Sam, though, he couldn’t cut it at Goldman. He was a sensitive guy, and the job made him miserable. So, in what was perhaps the best decision of his entire life, Sam quit his job at Goldman for a career in the start-up world.

Unfortunately, it was hard for Sam to shed the impulses and expectations that led him to take a job at Goldman Sachs in the first place. When I met Sam he was doing great on paper. But he was still working insane hours at a toxic startup and was taking sleeping pills every night. He once shared that he would love to move to Colorado and get a puppy, but it was in a like-that’s-ever-going-to-happen tone of voice that New Yorkers often use when speaking of a more gentle life away from the city.

Sam also told me that he sometimes felt like a failure because his friends from high school were making half a million dollars a year at Goldman Sachs and he’d been rejected by Harvard Business School. Sam’s lack of awareness of how ludicrous this sounded was probably due to the fact that he was a born and raised member of the New York elite. He simply couldn’t imagine how completely out of touch and insane such a statement might sound even to a relatively privileged but non .01 percenter like me.

On the surface Sam seemed like an ambitious guy. But after just a few passing interactions it was clear that he was completely phoning it in. He had an incredibly low bar for what life should feel like, and what it could offer him. Obviously it’s unfair that Sam had so much privilege and other people don’t. But what a total waste of all that good fortune! The world should have been his oyster. He could have been skiing all winter long, hiking with his dog all summer long, and working some totally fine job in Denver. Instead he was miserable.

Sam’s not the only son of privilege who totally failed to make the most of incredible good fortune. I see it all the time. And while you might be thinking boo hoo, what’s that, the sound of the world tiniest violin, I actually think it’s a real shame. The world needs more vibrant people, not more depressed men, who turn into problematic managers, mediocre fathers and sub par partners.

Which is not to say all well-heeled men are phoning it in. Some are living their best lives! Also, there is another side of the coin too. I’ve seen some other people phone it in a different way. I didn’t notice it until I started approaching my early thirties. All of the sudden, all my friends (again in New York) were talking about retreating to a cottage in the woods and making herbal tinctures. None of them actually did it (and maybe they should have!), but the rumblings reflected a deepening dissatisfaction with what the New York professional world had to offer them. Still, none of us, at the time, seemed to have any creative ideas for how to build a more satisfying and sustainable professional life.

This disavowal of ambition often includes the following negative beliefs:

1. It’s bad to want to have a lot of money

2. I don’t have what it takes to get a high paying job

3. If I did get a high paying job I would have to abandon everything I care about (art, service, empathy, connection, creativity, community, quality of life, rest, family, vacation, spending time in nature)

So they don’t even try. It’s this weird binary mindset, where money = messed up guys like Sam, and if you want to not be like that, or be around people like that, then you basically need to join the Peace Corps, or make, like, $35,000 working for a non-profit.

But that’s not how the real world works. In the real world jobs are very specific and niche. And fun things can pay well. Nourishing things can pay well. Weird super specific jobs you’ve never heard of can be fun, low-stress, well-remunerated and rewarding.

So whether you’re killing yourself for the chance to hit the big time at some dumb startup, or neglecting your financial wellbeing because “meaning” is more important, in either case you are insufficiently ambitious.

You need to BE MORE AMBITIOUS. You know how in “The Perks of Being a Wallflower” the teacher tells the kid “people accept the love they think they deserve?” Okay, well that’s true for jobs, too. You accept the job you think you deserve. So be more ambitious about what you think you deserve. (You might consider talking to a therapist, mentor or friend if this is hard for you and you struggle to feel like you deserve more)

Here’s what ambition could look like: I am looking for a job that:

• Pays over $100k

• involves working with nice and respectful people

• Makes me feel excited to get up in the morning

• Allows me to ski three days a week all winter long

• Let’s me use my teaching/instructing/coaching skills

• Has great parental leave for when I have a kiddo in the next few years

Is that ^ the holy grail? Maybe. Does it exist? 100%. Just because you haven’t experienced it yet, doesn’t mean it’s impossible. It’s like that Peter Paul and Mary song: “Do you believe in something that you’ve never seen before?”

Don’t be like Sam. But also don’t take the wrong lesson from Sam. Just, like, be more ambitious for yourself and what you think you can get. Don’t accept a bad deal, just because you’ve never been offered a good deal before.