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Realities of Freelancing: Always Applying, Always Pitching

As we near the anniversary of my having started my patchwork job (freelance combined with part-time work), I thought I’d write about some of the things I’ve learned in the last year about being a freelancer. This is the first post in my “Realities of Freelancing” series.

While I enjoy freelancing, I’ve decided that my real passion lies in libraries. There are some library jobs that allow part-time work from home, but at this stage in my career it’s pretty much impossible to be a freelance librarian (maybe once I have my MLS and a large dose of creativity!).

So I’ve been scanning job postings for opportunities to take the next step in my career. I plan to go back to school in a few years, at this point I’m looking for academic or junior (no Master’s required) reference positions. The market is tight, but Friday I ran across 4 good-looking opportunities here in the DC area.

Yes, I am getting to the actual freelancing point.

Anyway, I spent a good chunk of Friday working on cover letters for three of the positions. If you were following me on twitter, you may have noticed a downward spiral. I compared it to having teeth pulled and mentioned wanting to throw up. Over dinner, I talked about these feelings with Micah and he reminded me that sometimes editing his dissertation nauseates me. It’s not the quality of his work, but the fact that I’ve edited every draft he turns in and I’ve just seen it too much.

Which, in turn, reminded me of one of the realities of freelancing I dislike the most: pitching. Unless you land one sweet gig that covers all your needs, you will always be pitching. Sometimes you’re pitching every day and sometimes you have enough repeat clients and recommendations that you don’t pitch for a couple weeks.

Pitching can induce the same nausea factor as applying for jobs. If you’re lucky, you’re so excited by what you want to do (or by the job you’re applying for) that it feels fresh and fun. But sometimes even if the job really interests you…all these library jobs sound like something I’d enjoy…you feel so overcome with the repetitiveness of the words that you can’t stand it.

Writing three cover letters in one day makes me feel phony, like I’m repeating fake lines. I expect people to see through me and reject me. (But I knew spacing them out wouldn’t be any better.)

Now that I’ve gotten you depressed about the prospect of freelancing, I should add some tips that I’ve found make pitching/applying easier. It’s all about the mindset.

First, remember that (unlike you) your potential client/employer hasn’t seen a thousand different versions of your resume and cover letter. This is their first time experiencing you. They have no idea what you draft looks like or that you send a similar cover letter when you applied for a similar job two weeks ago. I’m all about reusing material if it’s relevant.

Second, if it’s good the first time then it’s probably still good. Again, don’t be afraid to reuse material. If it’s stilted or doesn’t apply to this situation, get rid of it. The last thing you want is to send a lifeless proposal or something that is full of energy and doesn’t address the actual job.

But if you were full of energy about a cataloging job at one university library and you’re excited about a cataloging job at another university library, there are probably whole swaths of your cover letter that you can reuse. And if you’re telling a potential client what your services for WordPress blog setup include, why not reuse part of a similar letter to another client? If you wrote it well the first time, then all you’ll get from trying to rewrite is awkwardness.

Third, take a break and spend it thinking about what excites you about this job. Stop trying to write. Or if you’re going to write, write down for yourself all the reasons you want this job. Think about how it connects to other things you’ve done. Get a snack, take a walk, let it percolate like a good cup of coffee. Then come back and write from the things that excite you most.

These don’t work all the time, but if I remember any of them while I’m pitching or applying I feel better.

What about you? Does applying or pitching get you down? Do you have ways you work around it?

Future posts in this series may fall into a schedule or may come when the inspiration strikes and I’m reminded of a reality of freelancing.


daddy t November 8, 2008 at 4:58 pm

I enjoyed your article. I think your idea of taking a break is a good help to creativity. It clears the mind and lets fresh ideas come in. (I tend to get glued to the computer screen.) Get away from the keyboard for a while by taking a walk is good. I’ve gotten some of my best ideas while mowing the lawn. I’ve even asked for help from above. That works too.

Fabulously Broke November 8, 2008 at 5:31 pm

That’s the killer part about freelancing. But I guess in consulting it’s a lot easier than for writing

Funny about Money November 8, 2008 at 8:55 pm

Yup. You’ve got it: Freelancing is essentially applying for a new job about three times a week: forever and ever, world without end, amen.

With no health benefits.

If you have a job that will put food on the table and provide health insurance, or a spouse whose job will provide the same, then freelancing is OK if you can tolerate the nonstop hustle. In one earlier incarnation, I realized that I needed to quit when I found myself hustling some guy for a job at a bar association cocktail party. Yech! It can expand to take over your life.

Frugal Dad November 10, 2008 at 6:52 am

You touched on one of the tougher aspects of freelancing for me, even doing it part time–pitching! I don’t consider myself a great salesman, and it is something I’ve had to work on to get a few opportunities here and there to supplement blog income.

I try to standardize the main points of my pitch and then customize only certain areas of it for various opportunities, so at least I’m not having to repeat the majority of the pitch over and over again.

Kate November 15, 2008 at 2:11 pm

I think a lot depends. I didn’t enjoy pitching when I first started, but as long as you are sure to stay on top of things, and not let it take over your life it can be fun. You just have to compartmentalize it so you don’t end up spending every hour of the day in search of work.

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