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What I’ve Learned

(If this guy and that guy can have somewhat condescending autobiographies written, I can compile a list that indicates expertise where perhaps there is none.)

red tie dinner

1. Have no pride

I used to be one of those girls who parked her car next to her boss’ in the lot. I held my head up high as I changed the filter of the company coffee maker, I answered phones with dignity. I knew that I was good at what I did, and I fulfilled my job description expertly.

Freelance doesn’t come with the kind of self-congratulatory recognition of a job well done. You’ll learn quickly that you will take any job (“Write advertising about a reusable tampon made of cigarette butts? Sure! 50% upfront, we’ll have the entire project to you by Friday.”) You will also learn how deep your well of patience is. You will perfect the art of smiling when you’re told that the job you wasted your entire weekend on has been pared down to two sentences that are grammatically incorrect, or you’ll write countless, fruitless taglines for an establishment that you would never frequent. Clients will yell at you and you will take it; and even if your general nature is to spout out riot grrl lyrics, you’ll learn to be called “dear,” “hon,” or “cute” by a potential client. Because patience equals money. And Kathleen Hanna never paid your T-Mobile bill.

Additionally, you’re going to have to ask for help. Accept that fact. Even if it’s in the form of an email to a writer you respect for guidance on creating the perfect metaphor, or putting a donation button on your blog (ahem), or simply handing out your business card at every opportunity, remember that the squeaky wheel gets the most oil. Especially if it’s a wheel attached to a Ferrari, not a fixed gear.

point and click

2. Don’t think too far ahead

Sometimes the unpredictable happens. For example, last week our old office was broken into and Simon’s computer, router, Grundig radio, and space pen were stolen. This was not something we had planned on dealing with, but you take the rough with the smooth.

It’s easy to want to compartmentalize your experiences and look to the future, especially if you’re a product of the higher education system. Grade school leads to high school leads to college leads to a master’s degree or a job…leads to marriage, house, kids, retirement. Let’s face it, freelancing barely pays this month’s bills. I can’t conceive of a day when I will be able to actually save money to purchase the stamps for the envelope that would mail a mortgage payment, let alone buy a house. Or a car. Or a pair of new shoes.

If you commit to following your passion, chances are you’ll have to accept that you don’t know what’s around that proverbial bend. It’s like The Lady, Or The Tiger?, only it’s The New Client, or Sell Your Stuff? Hopefully karma will repay us for that theft and the next unpredictable turn of events will be an email offering us a new gig.

Besides, you’re fucking batshit if you think you’ll ever be able to retire. And I don’t even know what you do for a living.

listen up

3. Have side projects

I know this probably seems a little counterintuitive, I mean, if you’re starving how can you focus on anything else? But if you don’t want to go apecrap bananas and wind up so stressed that you start having hot flashes and diarrhea, get a hobby. Seriously. One of us is a DJ on the side, the other has a blog and a crossword habit. It’s essential for us to write our own stuff, may it be stories, poetry, articles, blogs, grocery lists. Being stuck in “work mode,” even if it’s what you love to do, can only suck the passion right out of the party. Just like how in a functioning relationship you need time away from your partner, as a freelancer you sometimes need to stop swimming laps in the professional pool in order to soak in the creative hot tub.

Also, I cannot understate the importance of regular showers, wearing an actual outfit while working, and making sure you have readily available caffeine.

drop down and give me twenty

4. Be grateful

The donations from this blog, the clients who have solicited our work after reading, anybody who has ever sent an email saying simply that they enjoyed this professional whingeing diary…thank you. (And, yes, I mean whingeing.)

There isn’t a day that has gone by since the beginning of going freelance that I haven’t felt sincere gratitude towards strangers. It’s a symbiotic relationship, really. If we get work, we get to eat; if I get letters and donations as a result of this blog, I can’t flake on it and just say, “Oh, fuck it, nobody is reading it anyway.” The equation for persistence isn’t like that “success” piechart of 1% inspiration, 99% perspiration. It’s 50% feeling guilty combined with an immitigable need to make people like me.

Any morning that I wake up and don’t wince because I have eight hours of something I don’t care about in front of me is a good one. It’s people who read this that make that possible. I know it’s a hippie-dippy thing to say. I know it sounds like it should be the voiceover for a public television ad. But know that if you read this, you are directly making somebody’s life better. (Mine. And, indirectly, Simon’s.) Double that happiness if you give feedback.


5. The Internet is every fuck up’s PR firm

I know my friend Lisa. She lives in Chicago, likes to read David Foster Wallace, has a dog named Reeses, and hates pad thai. From her photograph I can tell that she has brown hair. I could not, however, pick her out of a lineup, or notice her on a crowded bus. She, on the other hand, thinks I look like a rotary telephone. Because that’s my icon.

The internet is a bizarre place. You “meet” a lot of people on it, and by following tiny, self-administered snippets you can feel as though you’re let into a person’s life. If you’re lucky, you meet some good ones. But a lot of the time, however, you wind up with what I can only describe as the kinds of people with the social skills that got them banned from the Renaissance Faire due to bad behavior.

In order to write about yourself you probably have some hope of getting attention. Understand that part of creating an identity on the web — no matter how close to the truth it is — requires some level of persona management. People will think that they know you from what you‘ve written, it is likely that they do not. People may feel that they have the jurisdiction to pass judgment on you, and they do, because you are sharing something, may it be as trivial as the kind of cereal you had for breakfast or the fact that you accidentally got elbowed in the face during sex.

That’s not to say that anyone has the right to aggressively berate you or act seedy and weird. Playground rules still apply: play nice. But recognize that by using the internet to voice your opinion, or to do a burlesque dance of verbiage for work, especially as a freelance writer, you’re putting yourself at risk of being scrutinized. And, of course, there’s that issue of oversharing.

Just take note, dear reader. Readers, plural, if both of you are reading, Mom and Dad. Keep your head up, keep your distance, but most important of all, keep trying.

write to me

Ainsley Drew at gmail

Brevity equals wit?

Cash money.

(Thank you.)



  1. Sometimes I want to be your secret admirer, other times I just admire you.

  2. Yeah, what Kelly said.
    Ainsley, you’re figuring out and putting into words things that I’d only sort of been dimly aware of as I built my freelance career.
    I would phrase number one differently, though: there’s a lot of pride in meeting a challenge put to you by a demanding client (who may in turn be responding to challenges of their own that you’re unaware of). Everybody who freelances has had a horrible moment (mine was a repulsive logo for a vile metal band that was paying me in cash money that I could take and spend on food).
    The congratulatory moment comes when you realize that someone just gave you money! For writing! (Or in my case, designing!). Turning your skill at something you love into a living is harder than fuck, but worth it.

  3. I love this. Like Esquire’s What I’ve Learned, minus the flaky.

    “{Y]ou’re going to have to ask for help.” This is a lesson I’m still learning, and it’s crucial. The implicit acceptance that I need help is the part I struggle with.

    And I love the idea that there should always be something to work on: “[Y]ou’re fucking batshit if you think you’ll ever be able to retire.”

    Why would a person [with modern opportunities] ever want to stop altogether? Maybe not the work you always did, or in the way you always did it, but something.

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