The Freelancer’s Dilemma: To hustle or to apologize?


Chapter 1, ‘The Freelancer’s Dilemma,’ is an excerpt from Manners and Mores: A Tutorial for Freelancers Tired of Hustling and Prone to Apologizing. The Table of Contents is included below the excerpt.

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1. The Freelancer’s Dilemma

For reasons as much of historical contingency as of personal choice, we are all freelancers now. The freelancer, having struck out on his own in the hope of making a certain form of life work, soon becomes bewildered. It is tough going, he finds, tougher than she had anticipated, and everyone now seems to be doing the same thing: launching the same startup, making the same pitch, putting in more fruitless, harried hours. Whether young or old, whether working with high-end clients or piecing together nickel-and-dime projects, the bewildered freelancer faces a dilemma when it comes to securing new projects or expanding the circle of his likeminded acquaintances: he can either plomp for hustling or festoon his epistles with more and more apologies.

On the one hand, the freelancer-turned-hustler is inclined to believe that it is a necessary evil to engage in this War of All Against All. Each contact, each new acquaintance, each business partner, he reasons, is to be used as a means for the end of maintaining some semblance of financial security. Everyone does it, so why not him? Yet in his heart of hearts he finds the habitual manipulation of others gruesome, disgusting, and ugly. On darker days, he also realizes that, apart from being exhausting, hustling is not all that effective at getting what he wants, nor of liking what he has, nor of being pleased with what he has done. Kant already knew that the one who habitually breaks his promise cannot be trusted, and trust is one of the social virtues that makes possible a sustainable life in freelancing. Lose your credibility, be deemed untrustworthy when you’re out in the world on your own and, over time, you’ll also lose your shirt.

On the other hand, the more self-aware freelancer may develop a guilty conscience and seek to turn away from hustling. For this, the apology comes in handy. During my conversations with some former conversation partners, the idea of being ‘too forward’ or of ‘putting oneself out there’ would quickly lead to the pre-emptive apology, the idea being to apologize even before the other is injured.

Yet this simply won’t do, since the guilt-ridden freelancer has to reckon, some way or another, with the fact that she remains dependent on others (many of whom she doesn’t know well) in order to complete projects and secure new ones. Thus the ineffectual nature of the overdone apology: a standard email might begin with an apology, move on to indirect discourse, get around to making a tucked-in-sideways request, ask about the family, and end with a second apology. In person the apologizing occurs much more frequently than over email.

The freelancer’s dilemma can be easily stated. Either he hustles, or he apologizes. If he hustles, he grows to detest himself for his mistreatment of others. But if he apologizes, he grows to detest himself for his dependency on others and on his undeniable social awkwardness. In both cases, he detests himself.

Can this dilemma be overcome? Yes, but only by recalling something significant we have forgotten and by practicing what, during certain periods in history, had been all but second nature. I am referring to the project of becoming well-mannered, of following–while reinvoking–the mores and manners that have served as the ‘social glue’ to ensure that all involved understood reasonably well the conduct of each. If one is well-mannered, then one can be assured that the addressee is not offended or put out; better yet, that he understands; better still, that he wants to further what needs furthering.

There are, however, two common misconceptions we need to clear away from the outset. The first is that manners and mores are merely ‘arbitrary’ social conventions. They are not: they are instead common ways of encoding the appropriate forms in which good things are said and fine are things done. The one who follows these traditions does not have to reinvent the wheel, making everything up as he goes along, but can be confident that he is acting reasonably and speaking agreeably, inasmuch as he has found that felicitous mean between the ‘too forward’ and the ‘too diffident and reserved.’

A second misconception is that one can be well-mannered but at the same time evil or malevolent. But just as, by the end of Pride and Prejudice, Mr. Darcy is not George Wickham, so the well-mannered is not the charming. The first does well by others, the second courts vanity.

Still, it may be objected, this difference is merely verbal. A man may open the door for a woman, but his goal in doing so may not be to show deference toward her but to have sex with her later on. Similarly, one may write a note of praise to another but this simply with the aim of ferreting out some kind of deal in the future.

To my ear, however, these quibbles seem ‘too far along.’ Any praisesong worthy of the name, for instance, is already shining a light on the other, paying attention to the other’s virtues, saying something about what maes him good. Whatever comes contingently after this note of praise does not necessarily come because of this. It is enough, if one wishes to defend manners and mores, that the manner in question be well-practiced, that the more be followed appropriately. I open the door well, you say thank you, and whatever comes after comes after–or it does not. The social grace has been achieved. The immediate aim, in other words, is that a social encounter be arranged, a meeting held, an introduction facilitated, a host greeted with proper warmth, and so on.

Good manners thereby sustain and replenish the social world; they make no guarantees about ‘deliverables’ and this is all to the good. As a result, a freelancer, who’d like to ‘make it’ in freelancing, can draw from what is best about the past. He needn’t be riddled with worries (as the profligate apologizer is) or beleaguered by self-loathing (as evidenced in the ‘dark night’ of the hustler), so long as she learns how to speak eloquently and act appropriately.

This is a tutorial in just that: in the gentle arts of introducing, inviting, praising, acquainting, having non-agenda-based conversations, and saying graceful goodbyes. Out of humility, manners makes no promises that one will ‘get on,’ only that one will be agreeable, someone others would like to have over for tea. And this, of course, is the more important thing.


Table of Contents


1. The Freelancer’s Dilemma

2. A Few Choice Words About Style

3. A Word or Two of Caution About the Ills of Talkativeness

4. Unregrettable Words About the Art of Invitations

5. Lovely Notes of Introduction

6. Pindarian Notes of Praise

7. Giving Beautiful Thanks

8. In Praise of the Open-Ended Conversation

9. On Hosting and Being Hosted

10. On Saying Your Graceful Goodbyes