Stuffed or Starving: A Conversation from the Split Personality of Every Freelancer

(Okay, maybe not every freelancer. Maybe just me.)

I’m a planner. I work best when I have a series of actions that I can execute one step at a time. In part, that’s why I like freelancing, and it’s also what I liked about school: every assignment can be broken down into actionable, time-stamped steps. Need to write a paper by the first of the month? No problem—just schedule research for this week, first draft next weekend, revisions the following week, and wah-la: a finished term paper! Plus, what’s even better about both school and freelancing assignments is that no one cares when, where, how, or even whether you perform any of those steps. They just care about two things: the deadline and the final product.

So scheduling and executing . . . not a problem. This means that, as work is rolling in—the “feast," as it were, because freelancing is nothing if not feast or famine—I am fairly successful at keeping the internal voice shouting Ohmygod you’ll never get this all done to a dull roar.

Because really, it all comes down to living by a saying my father loves: How do you eat an elephant?

One bite at a time.

And I can definitely do that.

Unfortunately, it’s when there are no bites left that I start to panic. Like, for instance, right now, when I’m sitting here blogging, trying not to think about the fact that I have gone thirteen days without working a single billable hour. Sure, I’ve written some emails about lining up potential work. I’ve had phone calls with a few prospective employers. I've even gone on job sites and applied directly for projects. But earned any cash money? No. Which leads to what I can only describe as an argument between the two sides of my Split Freelancer Personality. The exchange goes something like this:

All the work has dried up. No one will ever hire you again.

Untrue! We had tons of projects last month. Just wait it out.

Yeah, okay. Keep waiting. You know what they say about people who wait? They starve to death.

I don't think that's the saying. [pause] But yeah, I know, I should be doing more. Pitching more magazines. Researching more university writing departments. Looking for more freelance assignments. Networking. [shudder]

Orrrr you could just start looking for a fulltime job. Because that’s what you’re going to have to do, anyway, when this little endeavor of ours spectacularly fails.

Just because you’re scared doesn’t mean I have to give up already.

Scared? I’m realistic. Remember all those people who told you that writing is not a viable way to make a living?

Working 40+ hours a week at a job I hate isn’t making a living--it’s making a salary.

Let me know how those platitudes taste next month, when you're eating rice and water out on the curb.

Don’t be dramatic. I can pay the rent for several more months even if we don’t get any more work. And I will get work. I’m qualified. The work is out there. Other people are doing this.

Yeah, other people with advanced degrees and resumes that include NY Times bestselling authors.

Okay, fine, I might not have a MFA or a PhD in editing--do they even have those?--but I’m good at this damn it! Or at least I think I am. Some people have told me that I am.

Sure they have. If you sucked, would they have said anything?

Well. No. But I wouldn't have repeat clients if I sucked. And Professor X requests me personally!

One professor. Wow. Way to go.

Hey, we're just starting out. Be patient.

We've been at this for almost a year.

Ten months. And I like it! I like the work, I like the lifestyle. I feel way more fulfilled now than with anything I was doing before. And I don’t care if I never make six figures. That has to count for something, right?

Never making six figures and barely making five aren’t quiiiite the same thing.

Oh shut up. I’m going to go back to brainstorming articles to pitch.

Or you could take a nap. Because do you really want to spend all those hours researching and writing and revising, only to get paid $50 a pop? Plus, they might just reject you outright.

… or I could take a nap. Okay. You win. For today.

The Thing About Picking Up the Phone

Here's the thing about picking up the phone: no one does it anymore. Everyone has smartphones that text and ichat and snapchat and email. And when we do pick up the phone to make a call, nine times out of ten we wind up talking to an automated system instead of a real person.

Therefore, when we are finally forced to talk to a real person--never mind a real person we don't know--on the phone, well . . . I for one find it terrifying!

I bring all of this up because for the first time in my life, I am forced to face this very task on an almost-daily basis. And I can't avoid it or put it off or write a letter instead. It's part of my job.

For anyone not in the know, after six-plus years of service at Wiley, I left last November and joined CenterForce, a five-person conference company based in Greenpoint, Brooklyn. Although I've been there for nearly three months already, I've put off writing anything about my new job because, honestly, I wasn't sure what to say.

Essentially, I didn't want to judge the experience prematurely. Change is hard, new jobs are hard, new coworkers all sitting five feet apart is hard . . . so I didn't want my emotions to cloud my judgement when I finally sat down to write about the experience. Even now I cannot really say that I'm writing emotion-free. When anyone asks "how I like my new job," all I can really say is, "Wait and ask me again in 6 months." Because maybe by then I'll feel like I know what I'm doing. Maybe.

But now I know I can at least say with confidence: my new job involves making phone calls. Lots of phone calls. To literal strangers.

And it. Is. Terrifying.

My job is to recruit high-level executives who handle intellectual property at companies to come and speak at our conferences. (Imagine Susie Q:  a corporate lawyer who deals with IBM technology patents--when they're filed, who's trying to use the technology illegally, etc. That's who we want.) Basically, I comb the internet for these people and then email them an invitation. If they don't respond, I might email them another invitation. And if they still don't respond, I start calling.

Every time I pick up the phone, my heart rate speeds up. Yet I know it's an irrational fear. My head tells me, "Allison, what's the worst that can happen? That you'll stutter and sound like an idiot? That they'll yell at you? Hang up on you? Who cares! You'll never see them again!" And based on my--albeit limited--experience, none of these things are likely to happen. Everyone I've spoken with so far has been very polite and oftentimes even nice. No one seems angry or annoyed.

So what am I so afraid of?

Honestly, I am not sure. What I do know is that I'm out of practice with talking to complete strangers (especially strangers who seem much more "important" than me), and I'm out of practice calling people who aren't my friends or family, and all this lack of practice makes me very very nervous when it comes time to dial a new number.

However, if nothing else, I'm getting lots of practice these days. So now it's just a matter of getting that heart rate down and banishing the feeling of dread that always climbs into my gut when I pick up the receiver. Fingers crossed that such a day comes soon. In the meantime, you'll have to excuse me, but I have a phone call to make.