Success Seeking and Do Gooding

The world faces no shortage of people seeking success and needing repair.

Action: What are your actual motivations and why?

It’s alluring to tackle a new challenge. Probably because in many ways, it’s starting anew. Like clockwork, twice a year, I buy gear for a new sport, and months later, it’s been used no more than twice. Sometimes my enthusiasm overwhelms my common sense. The excitement and desire for novelty and accomplishment isn’t limited to the recreational front.

For those addicted to striving and proving themselves professionally, little compares to landing overseas in a new country with the directive to build & achieve. Even better if you’re starting from scratch. I suspect it is what drew me and so many of my former colleagues to life overseas, or even the next headquarters assignment.

You begin to accumulate those successes, which turn into a professional reputation, which must be constantly curated and leveraged for the next assignment, critical for the next success, and so forth. In this cycle, there is nothing more crushing than seeing someone less competent than you getting an assignment you coveted. And there is nothing more glorious, perhaps other than nailing the recruitment of a valuable asset, than landing an assignment that allows you to prove yourself and level-up your professional reputation.

Stepping out of CIA was hardly me breaking this cycle of success seeking. In fact, it was just another iteration of it. If I look deeply enough, it was an attempt to distinguish myself even more. “See I can be successful here and here.” And because I left to work on a technology that is national security and mission related, I could also say, “and it’s in pursuit of something more than just myself.”

The wheel of one-upmanship and success seeking justified with “do gooding” rarely stops turning. I say this not because I’m deriding who I was or who I am now, but simply because I’m at a point in my life where I’m thinking more deeply about it. My job at CIA was to find others’ motivations and now I’m finding my own. Usually when I asked a source “why” they felt a certain way, I always asked “why” in response to each answer at least three times to get to the deeper motivation. We all start with superficial answers that sound good, and the older we get, the more we have to take caution not to believe our own bullshit.

Humans are meaning-making masters. It’s a good thing until it’s a bad thing, and the line between the two is different for everyone and always a bit blurry. Serving at CIA was deeply intertwined with my identity, and in many ways, still is. I had begun to summit a steep mountain that few people get to climb. Did I really want to give it up and start at the beginning climbing a new one? Ultimately, my ambitions were bigger than that building, and I’m still trying to make sense of what that says about me.

And this brings me to the topic of the action line. Last night, my Jewish wife roped me into watching a Jewish matchmaking show on Netflix. Normally I would spend my leisure time reading a non-fiction book on something like the rise of the shipping container industry or mindlessly scrolling VC Twitter. (The concept of leisure is problematic when you’re in the cycle of “optimizing”). Yet, I secretly enjoyed the 30-minutes of distraction from my otherwise very serious life and longings.

On the show, the matchmaker referenced “tikkun olam,” which is Hebrew for “repairing the world.” My eyes welled slightly hearing about it. That we seek to repair the world across space, time, cultures, and religions tapped an emotional reservoir inside me. While the underlying concept of tikkun olam was not new to me, there is something about hearing someone else express and label what we deeply know to be a shared sense of connectivity and community among us. (And to hear it explained beautifully as a tenet on a reality TV show no less.)

Much of what has motivated me has been this sense of “repairing the world.” I strive to be the “repairer,” and the world faces no shortage of people and things needing repairing. This desire, I believe, is innate for the most part, because altruism and cooperation is one aspect of survival. But it’s also taught, and it was a lesson ingrained in me from an early age by my own parents, couched in the Christian context.

Though, in many ways, even good and noble pursuits of repairing the world are usually at their core, selfish. Even the good we do is because of the feeling of goodness we derive from it. And many of us seek to repair others without looking inward to repair ourselves, first. This in no way means I think we should stop doing tangible things that repair the world (and let’s acknowledge, we also need to do things to stop breaking it in the first place). But, we should look deeper and ask why we do what we do. Can doing good ever be a function of pure love for the object of love, or is it always in relation, even if in a small way, to the feeling we get inside the self? Is this simply a “design advantage” of our DNA to keep us alive as a species? Is there a better way to link doing good to feeling good to maximize good in the world? And does the motivation even matter if the result is positive?

I think it does. Though, I won’t say no to a wealthy jerk building a local school even if it’s meant to ensure legacy, gain a taxi write-off, and alleviate guilt from a more frivolous lifestyle, while feeling a sense of goodness for repairing the world. But if we don’t also reckon with what we may be doing that is first breaking the world, no amount of repair can fix certain levels of brokenness. Too many people believe a charitable donation to repair is sufficient, yet don’t realize it causes more polarization. My wife explained that in Judaism the most noble way of charity is for the giver and receiver to both remain anonymous to each other. This is to remove a sense of indebtedness and a sense of superiority. A far cry from most acts of charity these days. Are we really being noble if we’re intending to be noble?

At CIA, there was a shared sense of noble pursuit. It was an opportunity to combine the selfish pursuit of success with the deep sense of wanting to repair the world, to help not just “my” people in the United States, but help others around the world protect themselves, most often from despots. Of course, here too, we must ask ourselves to think deeply about why, and ask ourselves why three times to move from superficial (though likely still, true) answers to the deeper ones. From the outside, conspiratorial mind, I can imagine this idea of a noble pursuit rings somewhat hollow. (Especially if you have no understanding of how hard it is to get reimbursed for the most trivial of operational expenses, yet think the US Government can run elaborate “covert action” plans continually ensuring the U.S. as a world puppet master). Or you believe CIA has led to more brokenness in the world than repair. But, that’s a topic for another essay.

Perhaps you’re a former colleague and a self-described “doer,” “realist,” “action-oriented,” and “don’t have time for all this philosophizing” type person. I get you, I’ve felt that way, too. I’m not a nihilist. The name of my site is “The Action Line” for a reason. Yet, there is a balance that I feel the need to strike more between thinking and success seeking and do gooding. Where are we virtuous versus mere virtue signaling, and how is this helping or harming our communities and society? Perhaps there is still a deeper notion that thinking about this dseeply, and documenting it for the world to see, will make me more successful. Either way, this is my new way of tikkun olam in a world of information overload, polarization, and what feels like a deep tearing of the fabric of our societies, our families, and ourselves. My goal is to write essays here, weaving in aspects of my past, to my current thoughts and future aspirations, and I hope you’ll join me.