The Entrepreneur’s Dilemma

I work for myself, which means my boss is a real bitch. She makes me work long hours, never likes anything I produce until I’ve revised it a thousand times (and maybe not even then) and, after all that, she’ll hardly ever pay me a compliment or let me relax on vacation.

Is this what I signed up for?

I went freelance after fifteen years of being employed at corporations and start-ups, and after numerous employee satisfaction surveys, the results are in: I’m the toughest boss I’ve ever had, no contest. The nature of self-employment, whether we’re talking about being an entrepreneur, a freelancer, or an independent creative of any kind, fundamentally means accepting responsibility for not only for your labor — the means and speed of working — but also the end result. That means that when something you’ve developed — whether it’s an object or a service — gets no reaction (or sales) from the public, or never even makes it out the door, it can call into question nearly everything you believed about your idea: that it’s good quality, that it’s smart, that it’s interesting, that it’s meaningful, that it’s necessary. Posing an even greater risk, however, is the fact that you might call into question those same beliefs about yourself.

Knowing what’s at stake, you tend to push yourself to your limits.

Most people don’t have the constitution to handle the stress and anxiety of living under such conditions, and prefer the safety (albeit illusory) and relative comfort (albeit dreary) of employment. Those who persevere with self-employment regardless of the insecure atmosphere inherent to independence are typically determined to do so based on the conundrum of being unable or unwilling to take a so-called “day job”. Put another way, so astutely by Lori Greiner: “Entrepreneurs are willing to work 80 hours a week to avoid working 40 hours a week.”

In a nutshell, this is the dilemma with which we’re faced: To what extent am I willing to work myself into the ground for my work? Is my work more valuable to me, than me?

The engine that drives the fervor of independent work can be fuelled by any number of motivators, whether creative or social ambition, a desire to strike it rich, a need to maintain one’s independence or odd working hours, social dysfunction… the list goes on. But there’s one thing that I think makes modern independence harder than it needs to be, and I want to lay it on the examining table so we can cut it open and see what’s inside: our obsession with the idea that our work and our passion should occupy the same space.

We’re all seeking meaning from our lives, which is one reason why we look for work which contains the passion we think will imbue our every gesture with significance. However, like any addictive substance, passion is best used in moderation. That we somehow acquired the idea that life can be lived at a constant crescendo is a misunderstanding of the nature of life, ever in ebb and flow. That our daily working life should deliver to us “passion” is a misappropriation of a word intended to express an extreme state. (Not to mention a disservice to any experience we’ve had when we were truly overcome with passion.)

“So, what’s the problem if I want to be passionate about my work?” you might wonder. Well, let’s start with a point that was summarized so well by Miya Tokumitsu: “Nothing makes exploitation go down easier than convincing workers that they are doing what they love.”

Let’s be clear about this: working for yourself doesn’t eradicate the problem of worker exploitation. You’ve just replaced an external boss with an internal one. You’re a horse, cracking its own whip.

Now, try combining that self-flagellation with the expectation of passion. In short, when we place unrealistic expectations onto our work, just as when we place unrealistic expectations onto a lover, we give the object of our obsession an undue burden. If it does not lead to the crushing disappointment and heartache that are inevitable when our demands are not met, it leads to the collapse of the other under the weight of our expectations. By and large, we very rarely think of our love or passion as a burden on others, we tend to think that by loving someone or something, we are giving a gift. Well, if our daily application of love were healthier, this would be true. Unfortunately, most of us treat love as an obligation that we hand to the other: I love you, so make me happy.

What distinguishes the passion we give to our work from the passion we give to another person is that a person is better able to articulate, and defend, their boundaries. Having a dysfunctional relationship with your life’s work is a harder thing to identify, because… well, it feels so defensible to us. Noble, even, to believe in something and sacrifice yourself for something ‘greater’ than yourself. After a while, it may even be difficult to establish that ‘you’ still exist; you’re just a meat-sack through which your work is materialized. I don’t mean to get too metaphysical here, except to emphasize that the life/work structure of an entrepreneur is essentially existential. At great hazard. By fusing your work to your identity, as creators are wont to do, dissatisfactions or setbacks take on disproportionate significance.

Now, don’t get me wrong. There is, unquestionably, value in enthusiasm for your work, and in bringing a positive attitude along with you every day. We should each strive for the best versions of ourselves. The problem occurs when all of a sudden the project/process/money/product fails, after you’ve given it everything you’ve got, and you have to pick yourself up again. And again.

And again.

And again.

When that happens (and it will, because life) you might not have the energy, the desire, or the money to pull it together, yet again. And, if you subscribe hard to the dogma of modern times, the assertion that work should be your passion, it will mean you’re not just giving up on a little project, you’re giving up on your passion. You’re giving up on yourself.

If you’re a determined, focused, intelligent, creative person — and of course you are, because you’re an independent creator — then you will do whatever it takes to prove to yourself that you are not the kind of person who gives up on your passion. Whereas, on the other hand, think of the ease with which we might give up on a restaurant that gives us one bad meal, an acquaintance who doesn’t return phone calls, or a bad internet service. The very flexibility of mind that enables our creativity is somehow turned off when it comes to the terms and conditions for which that creativity is used.

Certain credos have been established in this entrepreneurial climate, like “Do What You Love”, that fit into the modern gestalt of asserting that work can be, and should be, a pleasurable thing. It’s one of the rallying cries of the upwardly-mobile, the over-educated masses that only found disillusionment with gainful employment, at the apparent realization that having work in itself was insufficient, you must “find your passion”. The unsaid completion of this thought is yet another oft-repeated cliché, “find a job you love and you’ll never work a day of your life.” It’s a strange, paradoxical ideal: in order to escape the burden of work, you spark the desire to find work you enjoy so much, that you are freed to work all the time.

To devote yourself to something is to create a relationship that is deeply challenging, complex, and, by nature, evolving. Buying into a utopian vision of that will only make reality all the more disappointing.

On the other side of that spectrum is the romanticism of pain. The bravado of notions such as “no pain, no gain” may inject some fervor into your work, and maybe even some tolerance for the lack of immediate payoff when pursuing long-term goals, but it delivers a rather disturbing and unhealthy comfort with masochism. I don’t think this leaves us any better off because, again, the dilemma of asking ourselves which do we value more, our work or ourselves, implies that one has to come at the cost of the other, and I don’t think that’s the case. Rather, it’s important to develop a healthy, sustainable relationship between the two, where both are encouraged and enabled to flourish.

The practical and un-sexy truth is that, even in a dream job, there are unpleasant tasks, there are bad days, and there are failures; and, even in a shitty job, there are pleasant tasks, there are good days, and there are successes. It’s mostly a matter of perspective.

To be able to survive moments of agonizing challenge, or to be able to tolerate colleagues who know how to push all your buttons, or to be able to handle long lists of banal to-do minutiae, it may be that a more modest credo is necessary: you must find a way to Love What You Do.

If you are anything like me, this sounds almost like admitting defeat. But what I’m advocating is not a working life of monotony or servitude, it’s rewriting the narrative of independent work to be more reflective of the full picture, and to emphasize that when we talk about “independence”, we must also learn how to be independent from our most demanding boss — ourselves. We must be willing to treat ourselves as we would a really good employee, and just cut ourselves some slack.

And part of that is just being willing to talk about the parts that are hard. What it means to truly take responsibility for yourself and your work, and the relationship between the two. If we refuse to talk about our frustrations, defeats and rejections (all of which are inherent to the process of creation) we experience the alienation of thinking that we’re alone in our failure, and that this failure is the result of some personal and individual lack, all of which compound the problem. By instead talking about the richness of our experiences, that is, by including in the conversation both the successes and the struggles, we portray to ourselves and to each other a realistic portrait of what it really means to take a risk, and what it really means to try to earn a buck off something we truly care about. By looking not only at the rewards and the end game, but also at the cost, we can spare ourselves the subsequent anxiety and depression that’s all too common among entrepreneurs, independents and creators. We save ourselves, and we save each other.

Because, maybe like most people, I’m not really looking to change jobs, I just want to complain about my boss.