The dark side of ambition

Ana Dean
Ascent Publication
Published in
8 min readNov 19, 2018
Photo by Dane Deaner on Unsplash

I was always one of those kids who wanted to change the world in a big way. The content of my dreams has changed from becoming a famous artist to manning the helm of a corporation to reaching millions via my writing, but the level of ambition has not.

I’m not sure where this ambition came from. My parents are not particularly ambitious, which often frustrated and embarrassed me because I couldn’t understand why.

My dad once turned down a promotion to a managerial position because he enjoyed software development more than management.

My mom is a genius when it comes to crafting everything from jewelry to lip balm, but doesn’t want to monetize any of it, afraid that it will involve extra work that distracts from the creation process.

I often held my best friend up as my model of ambition, throwing everything at her craft of modern dance even if it meant leading an impoverished life in New York City. But after two or three years of struggle, she tells me she might eventually switch paths and dreams of a laid-back life as a yoga teacher in Costa Rica.

As several of my friends settled into their post-college jobs, they developed what I found to be an appalling sense of contentment and enjoyment with their work. They were willing to stay in the same roles for longer than the year or two it took me to become dissatisfied with mine. As a result, I kept moving, never satisfied but always nostalgic for the overlooked elements of my previous jobs I’d taken for granted.

The more I looked around me, the more worried I felt that my own overpowering sense of ambition was driving me in the wrong direction. Why else would so many of my peers be happy when I was so restless and disappointed?

I had always taken as given that I should strive for greatness at all costs, that ambition was a quality to be prized. But without being clear about what I wanted and why, I wasn’t sure where exactly I was being led by it other than into an existential crisis. That led me to my first epiphany:

Epiphany #1: Get clear on what and why

When I graduated from high school, I was embarrassed by how plain my robe looked next to those of my friends, who had earned various pins, stoles, and cords through their academic achievement and extracurriculars. While still a high-achieving student, my chosen pursuits were activities I enjoyed, not ones I would list on a resume (or that granted such graduation-related swag). I planned to remedy this by choosing my activities more wisely when I got to college.

I put in over 500 hours of volunteer work, completed extensive research, made the Dean’s List almost every semester, and joined every honor society that would accept me. For this, I amassed my own extensive collection of pins, stoles, and cords by participating in national and university-backed programs. I’m unsure of what my actual contribution was to the worlds of science and activism through these efforts, but they sure as hell looked good on paper (and fabric).

It wasn’t until I neared graduation that I realized none of these accomplishments would directly inform what I was going to do next. For one, I wasn’t even sure what I wanted to do next, much less how to go about landing a job, for which I had not prepared myself other than bolstering my resume with generic achievements. With nothing but unfocused ambition to guide me, I assumed that my success would speak for itself, and from there everything would somehow fall into place.

Looking back on this particular form of ambition is embarrassing, because it’s a stark example of misguided achievement for achievement’s sake. Though I found much of my college experience enriching and fulfilling, I didn’t choose my experiences for these qualities, focusing instead on the tangible outcomes, which are hanging with my graduation robe in a closet in my parents’ house, doing little for me.

I fear that I am not alone in striving for outcomes in this way, that I’m not the only one who hasn’t been crystal-clear with myself about what I want and why I want it. The problem is that, in most situations, the distractions are more subtle, making it more difficult to separate the “achievement” value from the intrinsic value.

For most of us, ambition takes the form of a certain job, or a relationship, or a vague concept like “financial freedom.” These are the things we want so badly until we have them, realizing with horror that they were a flimsy veneer covering what we really wanted: joy, fulfillment, validation, and freedom, which despite our success remain as elusive as ever.

I’m shocked by how much time and effort I put into pursuits without asking myself for this justification. Why do I want that promotion? Why do I want to buy this or that? Why do I want to write? Do my goals represent the outcome that I want, or merely the feeling that I want to have about myself?

Clarifying these answers makes me realize I have other ways to achieve the same goal, the real underlying goal I was striving for in the first place. And if the goal is something like joy, fulfillment, validation, or freedom, then I have just saved myself a ton of work that I would almost certainly not have enjoyed.

Epiphany #2: Beware the ever-advancing finish line

Ambition is often rooted in my ego’s need to be more because I am not enough already. It arises when I face existential anxiety or a vacuum of fulfillment through other means. When I feel adrift, not driven by a cosmic pull in any direction, I will naturally find something that brings me satisfaction rather than question why this vacuum exists. And achievement in every form brings a lot of satisfaction, if only for a limited period of time.

Sometimes when my goals have been met, after a brief period of elation, I feel empty and wonder why I was not as fulfilled as I expected to be. This is when the ambition that I had used to cover up a gnawing background anxiety, to fill the gap left by a lack of intrinsic enjoyment, suddenly becomes a vacuum again. Ambition can never cease, no matter the outcome. If it has gripped my mind, no accomplishment will loosen that grip, though each time I hope it will.

This realization led me to develop the following matrix to describe the state of mind that ambition puts me in:

The way I see it, with unchecked ambition I can at best hope to become happy-ish, riding the high of achievement before needing the next (and larger) dose of success. In this way, chasing accomplishments can become an addiction like any other.

Ambition can also get in the way of enjoyment when the all of the focus is placed on the outcome over the process. When I fail, my work becomes less enjoyable for obvious reasons. But when I’m successful, the pressure of maintaining that success replaces joy with anxiety, because now I have people to please, something to lose.

I struggle with this now, after attracting over 250 Medium followers (many thanks to all of you, by the way) from a portfolio of only five essays, which seems too good to be true. I can already feel the pressure mounting to top myself with every subsequent word, the focus shifting from what inspires me to what might inspire the most engagement. Part of me always knew this would happen. I’m just surprised by how little time and recognition it took.

Epiphany #3: Ambition isn’t the only driver of greatness

I’ve heard the argument that ambition is necessary because the alternative is stagnation. If we’re not ambitious, the world would see no progress. We would all live in remote woodland tribes doomed to a life of scavenging and perpetual lack.

I see where the argument comes from, and perhaps feel the fear behind it, but my problem with it lies in the assumption that all of the progress we have made is a direct result of ambition and ambition alone.

Surely ambition has played a part in bringing about innovation and progress. It would be hard to believe that innovators would still innovate if there were no money, no glory to be had from doing so.

But I can’t bring myself to conclude that extrinsic rewards are the only reason for progress. If personal ambition were the only force driving us, then we would find the path of least resistance to fulfill our need for accomplishment. We wouldn’t take risky bets on unproven technologies, instead deciding to start businesses that are tried and true, with as little chance of failure as possible.

If we were only driven by ambition, the arts would not continue to evolve based on how lucrative these professions are relative to nearly anything else. Who would do something with a near certainty of failure if their only goal was to achieve fame and fortune, regardless of means? Sure, many aspiring artists strive desperately for fame and fortune by ignoring the odds, but must also be supported by some amount of love for the craft to salve the ongoing disappointment they’re sure to endure.

We all want to get better at what we do. We want to be recognized and, hell, maybe even make a little bit of money. But that’s not all we want to do. For most of us, a life of pure ambition, of reaping rewards unattached to any sense of meaning and fulfillment, would be an empty existence.

Balancing ambition with contentment

Armed with well-thought-out goals and intrinsic enjoyment of all that I do, a natural question arises: how can I pursue my goals while keeping my ambition in check? As in all things, my mindset has more than a little to do with it.

What has most helped is visualizing exactly the life that I want to lead, being as detailed as possible about what I’d like to do on a day-to-day basis. I disregard my current circumstances and consider my work, my free time, and my relationships as a blank slate, imagining what I want and working backward from there.

Tim Ferris has built a tool for just this purpose called the Dreamline Worksheet. In it, I’ve detailed my financial needs and what I want to spend my time doing. I filled it out back when I had strong ambitions to lead a large company, and was embarrassed to find that the sheet was mostly blank. There were few physical things I wanted, and few expensive things I wanted to do.

Though I assumed I knew what I wanted out of life, the act of transferring my vague desires from my brain to the worksheet made me realize I had most of what I wanted already. Everything that I didn’t have I could easily save for without landing a six-figure job. The life I desired was already at my fingertips, but I had been taking the scenic route to get there.

Of course, there were other, non-material reasons I strove for corporate leadership (power, acclaim, proving to myself that I was cut out for such a job), but over time, these naturally fell away. Perhaps it was a change in my self-esteem, a shift in my priorities, or sheer exhaustion from working over sixty hours per week. As it stands, I value doing my job well and would welcome advancement, but it’s no longer something that I need to consider myself successful.

Don’t be fooled, however. My ambition is still there, screaming orders at me, telling me to chase this and that. But instead of rushing to obey each time a shiny new goal appears, I smile, pat it on the head, and go about my day.

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Ana Dean
Ascent Publication

Trying to make a living off of being “that girl.”