Entrepreneurship As Self-Actualization: When All Roads Lead to Founding

Joshua Neckes
Apr 21, 2017 · 8 min read

It is unequivocally the case that entrepreneurship has become a celebrated path of self-actualization. What’s particularly surprising is just how true that is, and for how many people.

The wonderful thing about entrepreneurship is that it is, in many ways, a universal vessel for our unique self-concepts. In this respect, it is a lot like the novel — it can be all things, subsumes all forms, and becomes all forms. The novel has constantly evolved to remain relevant through thousands of years; today, it holds within itself short stories, epic poetry, narrative history, and much more.

Similarly, entrepreneurship is a capable frame for almost every type of narrative that one might wish to cultivate about oneself. These frameworks are familiar to all of us — artist, seeker, rebel, visionary, wealth-seeker.

Self-actualization is often aligned with archetypes; wittingly or unwittingly, as narrative creatures, we move towards specific, establish frameworks of beholding ourselves. We use these frameworks to tell stories about who we are, what we value, how we are valued, and how we are to interact with the world.

We deploy them as pathways to develop ourselves, to soothe our inner shame, and to communicate our intentions to those around us — implicitly or explicitly.

What’s fascinating about modern entrepreneurship is how it represents a unifying modality for these frameworks. Historically, they’ve often implied vastly different “ways of being” in the world. We do not expect an artist to live the same life as a wealth-seeker. It seems obvious that someone looking for fame will not make the same choices as someone searching for inner peace.

Yet contemporarily, we can want vastly different things for ourselves, have widely varying intentions, behold ourselves in very different guises, and yet by all appearances perform almost exactly the same behaviors — as entrepreneurs.

Here are some examples of “actualized personas” that can be supported by entrepreneurship:

  • The Artist — For creatives, entrepreneurialism provides an incredible space in which to feel “seen” and actualized. Media and technology provide a nearly-limitless opportunity horizon for creation across all media, with the possibility of associated creative outputs that become an intrinsic part of day-to-day life.
  • The Capitalist — The pursuit of wealth-as-actualization is, of course, an American classic. For many, the (relative) decline of finance and associated ascendancy of technology has situated startups as the most attractive way to get rich. The arrival of these finance migrants (and/or startup bros) has caused significant hand-wringing among other startup cohorts, as it often feels fundamentally at odds “entrepreneurship-as-disruption”, and instead just a form of mainstream corporate co-option.
  • The Seeker — Someone for whom the creation of a new business or organization represents a liberated medium through which to explore what’s fundamentally “true” or meaningful in the world. For these folks, self-actualization in the 70’s might have come on Buddhist retreat (indeed, Steve Jobs was quite fond of his ashram); today, the founder narrative provides an “exploration of self-as-maker”, with ample opportunities of societally-sanctioned introspection (i.e. as a founder, it’s important to ask questions about how you feel — so that your startup can succeed).
  • The Changemaker — “Social entrepreneurs” are an actualized class among themselves now — looking to change the world through disruptive technologies fueled by more virtuous venture investors. Before the rise of the “startup”, these folks might have followed their brethren into careers fighting for environmental change at the NRDC, or toiling in the largely-thankless outposts of the State Department. Burnout, despondency, a sense of dependency on irregular funding cycles, and an eventual shift to “for profit life” were all common for this group. Today, the startup dream promises the best of all possible worlds: a life in which one can foster social change, be self-determined, receive public acclaim for one’s contributions, and pay one’s mortgage.
  • The Visionary — Deep down, there’s an immense drive in many folks to shape the future; to envision and manifest the most essential elements of future life: the devices we’ll use, the ways we’ll consume information, how we’ll travel, where we’ll go, what we’ll eat, and what we’ll wear when we get there. For many of these folks, entrepreneurship represents a more appealing path to actualization than, say, being a researcher, as it comes with the trappings of (real or perceived) independence, wealth, access, and self-determination.
  • The Celebrity — Fame is as enduring an American actualization path as making money. While these two paths may feel “emptier” than their more ostensibly noble counterparts (e.g. changemaking), or while some may quibble with the possibility of actually “actualizing” via renown, it is nevertheless the case that, every day, massive swaths of our society are motivated by the notion of becoming recognized. We see it in the lines for American Idol auditions, we see it on Shark Tank, and we see it in the board rooms of venture-backed startups.
  • The Rebel — RebelMouse. RebelMail. Disruption. James Dean as startup founder? Maybe not, but those looking to actualize themselves against society’s dominant narratives increasingly feel like they can find a happy home in entrepreneurship. Set your own rules, make your own schedule, report to yourself — what better way to experience yourself as fully independent and unfettered?

Many paths, same ostensible goals, same behaviors. In my last post, I spent time talking about entrepreneurial aggrandizement and some of the inherent issues in the founder narrative.

Ultimately, it seems to me that the more problematic elements of entrepreneurship can be distilled into the way in which it has become a sort of “catch-all” path for self-actualization. When competing actualizing modalities collide in a single behavioral set, it becomes hard to understand intention.

One can be a founder today because one wants to reduce income inequality — or because one wants to make as much money as possible. One can be drawn to entrepreneurship because one wants to rebel against the status quo — or because one wants to become celebrated by it.

In a world in which ostensibly conflicting goals can be pursued under the same flag, deception is a temptation for the less moral among us. It’s easy to try and have your cake (e.g. my fast-growing, disruptive company is amazing, and I should be celebrated as a visionary) and eat it too (e.g. don’t unfairly judge me for creating a monoculture of sexual harassment, I’m just a young seeker making mistakes).

We’ve seen plenty of companies recently where the founder both actively courted laudations for “disruptive innovations” and then fought back against the press for “being pilloried unfairly for trying to changemake” when those “innovations” turned out to be more smoke than fire. Again, here, we have an example of conflicting actualization paths — celebrity seeking vs societal progress.

In these scenarios, authenticity can become “mushy”, for lack of a better word — and other guises are assumed opportunistically. For a failing founder who originally got into it to make money, assuming the “rebel” guise can helpful defense against perceived external judgments. For a celebrity-seeking founder, working on a “for purpose” company can be a great way to shameless self-promote without actual business results.

To be clear, here: I am not passing judgments on those who seek wealth, or fame, or any other actualization path via entrepreneurship. It is not the relative value of these paths that’s even problematic; it’s the intersection of these paths, and the attempts to fluidly move between them as circumstances entice, that seems to be at issue.

Integrity and authenticity are paramount virtues for the entrepreneurial project. Today, being a founder offers a seductive set of actualization paths that can be opportunistically claimed in violation of these values. It is in this opportunistic claiming that founders lose themselves, what they stand for, and ultimately imperil the nobility of their new ventures — and the entrepreneurial project writ large. It is my hope that we can do better here.

Coda - Feedback From My Last Post.

In a week or so, I’ll look to dig a bit deeper on the stuff above, and would welcome feedback on the topic. I find the exploration of the entrepreneurial project both interesting and essential. Let me explain a bit more about why.

After my last post, I basically received feedback from two groups: folks who were happy that I’d explored the intersection of entrepreneurial aggrandizement and Donald Trump, and those who disagreed with the underlying fundamental premise that entrepreneurs have been unduly aggrandized at all.

This is generally a response to the second group. I’ll summarize the anonymized feedback of this group here — for those of you who’ve provided it, feel free to provide more clarity in the comments.

Essentially, a subset of readers felt as if I was far too harsh on the average entrepreneur, that I “didn’t spend enough time exploring the virtues of those who take risks to start their own ventures”, and that I “painted with an unfairly broad brush”. The majority of entrepreneurs, they argued, are “trying to build open and supportive workplaces”, “seek to defer credit and celebrate team members before themselves”, and “ultimately are just trying to make the world a better place.”

Moreover, these entrepreneurs are “taking on significant risk”, “constantly stressed out and lacking in fundamental life balance”, are “at the mercy of the press and powerless to fight back when unfairly targeted”, and “aren’t guaranteed anything by virtue of their status as founders”. “Access doesn’t necessarily beget access,” one founder noted, “and privilege doesn’t always beget privilege”.

Responding Directly

So, there’s a lot happening here. Rereading my first post, I can absolutely understand how, in a vacuum, someone might think I have a negative view of the average entrepreneur. That is not the case. I have dedicated a significant portion of my life to entrepreneurship, and I think it is a powerful tool, when employed correctly. Like so many powerful tools, it has no inherent virtue, and can also be deployed in the service of lesser causes (e.g. wealth); or, in some cases, co-opted entirely for more ignoble ends (e.g. Heideggerian death denial).

There’s a lot more to be said on this topic — more than enough to fill a few hundred pages, at least. My framing in the original article was not intended to provide that holistic summation of the global state of entrepreneurship; rather, it was intended to build on what I assumed to be a generally accepted sub-narrative of entrepreneurship writ large (i.e. that founders have been clearly lionized, and that venture-backed entrepreneurs have been incentivized to behave in specific ways that — outside the bubble — can seem bizarre or misguided).

This felt like a good foundation for an exploration of Donald Trump’s rise, and some of the larger social trends that perhaps link the two. Based on the feedback I’ve been given by founders and those in the tech community more broadly, it’s clear that there are still some rather deep divisions when it comes to that more basic global narrative around entrepreneurship. Specifically, there are clear disagreements about how entrepreneurs are beheld; this includes the scope of their challenges, the relative reality of their “aggrandizement”, the nature of their role within the larger cultural ecosystem, and the shape of the social contract that exists between them and their employees/society at-large.

Ultimately, I believe this is something that needs to be explored. In responding to my piece over beers, one founder in noted, “I think some of what you said is true and I disagree elsewhere; I might have shared your piece and responded publicly, but was worried that it would damage my company/how my company might be viewed, and I’m not going to do that”.

This really worries me. More than anything, there needs to be space to ask questions about the evolving role of the entrepreneur from within entrepreneurship. Otherwise, existent pathologies and more toxic modes of behavior will go unchecked, and we leave it to those outside of our space (who give less of a shit about its general trajectory) to uncover our challenges and hold us to account. Historically, that’s been a pretty poor approach (see: high finance, circa 2007).

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