ambition as a fingerprint

generalized vs personal ambition

"Don't be afraid of being different. Be afraid of being the same." Being Different, by Jason Noh

The reason I’m writing about ambition is two-fold:

1) I recently wrote about how crushes are often just misplaced ambition, and I have more to say on the topic.

2) I had an incredible conversation about success and motivation with two friends the other night. One of them identified her personal ambition—something she hadn’t crystallized until that conversation. It made me think: why don’t more of us know what we want? Why is it so hard to crisply articulate our definition of success?

The conversation began with me explaining my decision to focus full time on writing. I described how the traditional “ambition track” did not feel right to me, no matter how much I tried to convince myself it did, and that I’d rather try hard at this (writing) and fail than do the generically ambitious thing and always wonder. I explained how I don’t believe in objective right or wrong career decisions, and how it’s probably unwise to trust anyone who gives you instructive career advice, because the only person who can give you the “right” answer is you. The best advice-givers are the ones who ask good questions, listen to your answers, and then proceed to ask better questions after digesting your responses. Better questions, not blind instruction, lead you to the “right” answer.

Whenever someone gives me instructive advice, I think of this Viktor Frankl quote:

“The meaning of life differs from man to man, from day to day and from hour to hour. What matters, therefore, is not the meaning of life in general but rather the specific meaning of a person’s life at a given moment. To put the question in general terms would be comparable to the question posed to a chess champion:
“Tell me, Master, what is the best move in the world?”
There simply is no such thing as the best or even a good move apart from a particular situation in a game and the particular personality of one’s opponent. The same holds for human existence. One should not search for an abstract meaning of life. Everyone has his own specific vocation or mission in life to carry out a concrete assignment which demands fulfilment. Therein he cannot be replaced, nor can his life be repeated. Thus, everyone’s task is as unique as is his specific opportunity to implement it.”

While Frankl abstracts this idea to the meaning of life, the same applies to ambition. There is no single best move is now etched into my psyche (how easy it would be if there were one!) There’s only the right move for you, which depends on your specific circumstances, aspirations, and definition of success, or what I’ve been calling your “fingerprint of ambition”—what you want to be best at.

Determining our best move requires us to:
(1) define what success means to us, and
(2) reverse engineer the steepest path to get to there.

The sooner we do this, the better. Otherwise, we might pursue a generic path of ambition, only to conquer it and still feel dissatisfied. Our options will then be: accept or re-start, this time guided by personal ambition.

“To become wealthy, be willing to hit reset and start from scratch. Be willing to go back down the mountain and find a new path to the top.” —Naval

I wrote about how crushes are often just misplaced ambition, because one way people tend to express personal ambition is through romantic interest. As in: the people we crush on possess the qualities we want to embody ourselves. So, if you’re not sure what your personal ambition is, just look at your crushes. What do they have in common?

Steven Pressfield touches on this in the War of Art, where he explains how one way we squirm away from our ambition (he calls this Resistance) is by selecting our mate:

“Sometimes, if we’re not conscious of our own Resistance, we’ll pick someone who is successfully overcoming Resistance. I’m not sure why. Maybe it’s easier to endow our partner with the power that we in fact possess but are afraid to act upon. Maybe it’s less threatening to believe that our beloved spouse is worthy to live out his or her unlived life, while we are not. Or maybe we’re hoping to use our mate as a model. Maybe we believe that some of our spouse’s power will rub off on us, if we just hang around it long enough.”

In short: when our professional efforts do not align with our personal ambition, we outsource self-actualization in other ways—crushes, significant others, similar-but-not-quite-it careers that make us feel like we are developing. 

To recap, my thoughts on ambition so far are:

(1) Personal ambition has variance. Being ambitious ≠ only wanting money, power, status, influence. Ambition can manifest itself in more ways than just wanting to be a concentrated agent of capitalism (though the two are certainly not mutually exclusive).

(2) If you display signs of ambition early, you are likely to be funnelled towards paths that aim you at generic success (the aforementioned money, status, power, influence).

(3) If these paths don’t feel like they quite fit, you might manifest your personal ambition in other ways, like your love interests.

(4) Following your personal ambition = identifying your definition of success, and pursuing the optimal path to get there.

---

When Tim Ferriss asked Seth Godin how he knows something is worth his time in an interview, Seth mentions this Zig Ziglar quote:

“Don’t become a wandering generality. Be a meaningful specific.”

Seth says he tries to avoid being a wandering generality—someone who goes where inertia pushes them. Someone who does what they are told. Someone who lets life happen to them rather than the inverse. Seth goes on:

“There's nothing wrong with being a wandering generality instead of a meaningful specific, but don't expect to make the change you seek to make if that's what you do.”

To become a meaningful specific—someone who actualizes their personal ambition—we need to resist the pull towards the wandering generality definition of success. Thus, we shouldn’t ask just anyone for life/career advice, and absorb what they say simply because they’re smart or successful. If we want someone’s perspective, we should ask people with similar ambitions to us, or those living lives that resemble our definition of success. But more than anything: we should consult ourselves a whole lot more. We have the best data on ourselves! Our self-knowledge—the decades of time we’ve spent getting to know ourselves—is more valuable than any data someone can collect in a short conversation. We are best equipped to decide what we should do. Sure, others’ experiences can supplement that self-knowledge, but they should not replace it.

To see an example of generalized ambition, consider how some people start reading. It goes something like: the person decides they want to be “well read” (general ambition). They look up the “100 best books to read” and begin to read them. They find them boring. They think: None of these books are landing with me. Am I bad at reading? Do I have no attention span? Am I not intelligent enough? No. The books simply do not match their taste. A vanilla list of “great books” is not tailored to what you are interested in (your personal ambition!)

I’m a big believer in reading books that are interesting to you at the time that they are interesting to you. Naval says: The best book is the one you'll devour. And I agree. A book is most useful when it aligns with your curiosity, when it feels scathing—hot to the touch. When its words are melting your mind and re-shaping it. A book hits when you’re into it.

Book stores are filled floor-to-ceiling with a diverse set of books for a reason. We’re all into different things, and that’s okay. More than okay, it’s healthy. And the more we lean into our difference, the likelier we are to become a meaningful specific. The likelier we are to converge on our definition of success.

Another relevant quote—this one from Tim’s interview with Tobi Lutke (CEO of Shopify):

“I don’t particularly believe in Hell. But I like this definition I’ve heard: Hell is meeting the best version of you that you could have become of your life. And so I think that one of the really, really fun things about an experience like [being] an entrepreneur, or the careers we have, the books we read, is if they end up being pointed in a direction that allows us to minimize the difference between that person we will meet and the person we are, at that point in time—I think that’s time well spent.”

Hell is looking at the you that you’d be if you weren’t too scared or complacent to become that version of yourself. Yikes, right? And that means success isn’t just about accruing a huge pile of money, status, or prestige. Success is trusting that you—no one else—know what’s best for you. Success is actualizing your personal ambition, and hell is looking Resistance in the face at the end of it all, and knowing it won.

By aiming at a version of success that captures our personal ambition, we can make the best chess move for us, instead of seeking generalist advice that triggers self-doubt and confusion. It’s like trying to make your decision with someone else’s decision tree. Why would you do that? You have different priorities, beliefs, and preferences. You have to live with your decisions and thus, you should be the one making them.

As for my personal ambition: I’m acting it out right now. I’ve always hoped that one day I’d be learning and teaching in some capacity, every day. And that’s what I’m doing with my writing (well, I’m learning, at least). So no matter how this chapter unfolds, I’m content, because I want to manifest my ambition directly—not in who I fall in love with, or who I work for, or by society’s generic definition of it. I want to manifest my ambition with my actions, my choices, my chess moves! And if life is about closing the gap between who I could become and who I am, then writing this feels like time well spent.

PS—if you enjoyed this, you might like a similar post I wrote on discipline & freedom.