The Key to a Successful Freelance Career: A Diary

As more people work at home and telecommute, you can bet that the The View is expanding its influence.

7 a.m.

The key to a successful freelance career is routine. Give yourself a strict schedule, just like any job. People may complain about the inconvenience of the workforce—getting out of bed at an early hour, dealing with the boss and the co-workers—but that keeps us honest and productive. Without such checks and balances, some of us fall to pieces.

I wake every morning at 7 a.m. I make coffee and sit down with my boyfriend for a proper breakfast of yogurt and granola and fruit.

‘So what are you doing today?’ he asks.

This can be a daunting question for any freelancer. ‘I’m going to write,’ I say proudly. A positive attitude is another key to a successful freelance career. The job can wear you down, because freelancing involves selling yourself and your own work, an uncomfortable prospect for most writers. We’re an insecure lot, wary of self-promotion, prone to believe the worst about ourselves and our talents. I say nonsense. Believe in yourself, and you will prevail.

My boyfriend slurps the last of his coffee and looks at his watch. ‘I gotta go,’ he says, heading for the door. ‘Have a good day!’

For the next nine hours, anything is possible.

7:30 a.m.

I go back to bed. It’s still really early.

9 a.m.

One key to a successful freelance career is learning The Pitch. A good pitch is precise and confident and penetrating. Not, ‘I’d like to write about Ashton Kutcher because I just think he’s interesting.’ But, ‘Ashton Kutcher has risen to a heretofore unprecedented level of fame.’ See the difference? Hmm. I wonder what’s on The View today?

9:10 a.m.

Oh my God, I hate The View. First of all: Starr Jones is soooo not a lawyer. Second of all: Don’t even get me started. Thirdly: Who would give that idiot a law degree? The View makes me want to flush my head in the toilet. How can you people watch this crap?

10 a.m.

I turn off The View. I’m kind of hungry.

10:30 a.m.

So far this week, I have made three pitches to three major publications. This is a good track record, which shows that I have not lost hope. Losing hope as a freelancer is easy, because the pitches you send out—that you research and craft carefully—are often rejected. Sometimes, they are ignored entirely. This is the worst. Most of us can handle the sting of disappointment, but not knowing kills us. I haven’t heard back about my pitches, but I must be patient. A successful freelancer does not get discouraged. A successful freelancer simply reads MSN. ‘10 White Lies Men Tell Women.’ Ooh, what are those?


Stories exist all around us. They are floating in the air, they are hiding under the bed, they are lurking around the corner. I have found that the key to successful freelancing is being a story scavenger. You can turn anything into a story if you find the right angle. Watch, question, stay endlessly fascinated. ‘Why is this like that? If x is so, then y?’ I keep a notebook handy to jot down my observations. Here are some of the stories I’m currently developing:

Who created the musical fade?
How many Diet Cokes is too many Diet Cokes?
What does it feel like to kill someone?

1 p.m.

A successful freelance writer does not get jealous. When a friend emails to report that she’s been hired by a reputable magazine for a robust salary, a successful freelance writer is happy for her. Thrilled. She deserves it, and besides—it can only help to know powerful people in the competitive world of magazine journalism.

1:15 p.m.

But holy shit, this kind of pisses me off. I’m not saying I’m mad, but it’s like, I’ve been writing way longer than she has. Is she that much better than me? It’s probably because I never sell myself. I can never sell myself. I’m too timid, and I never ask for what I want. I have to go for it. I have to grab life by the horns and steer it. I can do this thing. Jesus Christ, I’m gonna do this thing!!!!

2 p.m.

Someone should really clean up this dump.

3 p.m.

Getting out of the house is crucial to being a successful freelancer. When I first began this gig, there were days—weeks, even—when I didn’t even leave the apartment. It wasn’t on purpose, but I failed to make the small, critical efforts necessary to break from work. It’s a slippery slope: First, you’re wearing your pajamas all day and the next thing you know, you’ve watched an entire season of Road Rules without budging from the couch. Everything outside seems so bright, and hot, and scary. Look, you don’t have to do much, but it’s critical that you do something. Read in the park, take a walk, get coffee, make some friends at the bar. Just a shot or two. Four, max.

3:30-5 p.m.

Drink, drank, drunk.

5:30 p.m.

If you’re living with someone—someone who cares about your well-being and believes in you and maybe supports you financially while you ‘go for it’ and such—it’s probably best to keep the whole drinking-in-the-afternoon thing to yourself.

‘How was your day?’ my boyfriend asks.

‘Great. Fantastic. Yours?’

He slumps in a chair. ‘Eh. I’m tired.’

‘I know what you mean.’

Since freelance writers tend to work alone, it’s easy to grow hungry for human contact during the day. It’s easy to pounce upon our partners as they arrive from a hard day’s work, toppling them with questions and requests: What happened outside today? Do you want to see the eggs I bought at the store? Try to give your partner 15 minutes to unwind. I get him a beer from the fridge. I could use one, too.

5:45 p.m.

It’s important to remember that sometimes, people with real jobs don’t understand how much work it is just getting through the day. They ask things like, ‘So, what did you do today?’

What the hell does that mean? I worked, just like everyone else. Just because I don’t ‘report to work’ doesn’t mean I don’t ‘get things done.’

‘I recognize that,’ they say, suddenly defensive. ‘I’m just wondering if you wrote anything.’

‘Did YOU write anything? I didn’t think so. What is this, the Inquisition? Nail me to the cross already.’

‘What are you talking about?’ they ask.

‘What are YOU talking about?’

‘Have you been drinking? Why is your face all red and puffy?’

See what I’m talking about? This is what I have to deal with.

6:30 p.m.


8 p.m.

The key to being a successful freelance writer is to surround yourself with as much encouragement as possible. It’s astonishing how quickly the wind gets knocked out of you. I don’t know if it’s me, or what, but it doesn’t take much to get me all crazy and talking gibberish. ‘I’ll never amount to such-and-such.’ Or, ‘I just want to work with a few nice senior citizens.’

The truth is that it’s hard to be a successful freelance writer. Sometimes, I think I’m constitutionally incapable. My self-esteem slumps underneath the weight of it. I let stories slip through my fingers. I fail to follow-up. I miss deadlines, and grow daunted by the blank screen, and every story ever written seems like a horrible affront. Moby Dick: How did he come up with that? Portnoy’s Complaint: That was MY story. And the question is, why bother? Why bother, when I could be working somewhere making a snug salary, smiling and laughing with people all day, going out for drinks after work with fun colleagues, enjoying a yearly bonus?

8:30 p.m.

But I don’t have any marketable skills. And those jobs don’t exist anyway. It may suck, but this is what I do. I should really get better at this if I want to survive.

9 p.m.

Huh. I wonder if there’s a story in that.