In early 2015, I hit a low point. My freelance writing wasn’t bringing in enough to pay the bills, and I was running low on funds. I imagined the resumes I had sent in response to ads on Craigslist and indeed were disappearing into overfull inboxes, never to be seen again.
I was desperate to find work – any kind of work.
When my situation felt hopeless, I got willing to do things that seemed crazy, like replacing my safe, formal cover letters with wildly honest (and sometimes borderline goofy) notes and going on interviews for jobs I was sure I would never accept. And those crazy things were the secret sauce that got me job interviews and, in the end, a position at a nonprofit I had admired for years.
One disclaimer: I'm not going to tell you to network. I'm terrible at small talk, and I hate networking. That doesn't mean you shouldn't reach out to your network when you're looking for work — I’m just not the right person to tell you how to do it.
Here are the three smartest things I did when looking for a job:
Before I reached my point of despair, I had a list of reasons why I shouldn't bother submitting job applications: I didn't have the required experience, it might not pay enough, I wasn't sure I wanted to do the work, and so on. I would convince myself that I couldn't get the job before I even applied.
I stopped listening to the hecklers inside my head and decided to commit to the job search process. I applied for anything and everything that related to writing and publishing and I even applied for jobs in my former field, paralegal work.
When I started to search for work in earnest, I gave myself a few rules:
I applied for anything and everything that related to writing and publishing, and I even applied for jobs in my former field of paralegal work.
On my way to an interview with an environmental nonprofit whose work I loved, I tried to figure out how to tell them, gently, that I didn't want the job. I went to the interview because I was following the rules, and also because I wanted to meet them. To my surprise, I left that interview very much wanting the position.
If I hadn't gone on multiple interviews for jobs that I didn't want, I never would have found a job I was jazzed about.
For most of my working life, I wrote very formal, old-school application letters with scintillating opening lines like, "I saw your ad on Craigslist. I think I would be a great fit for this position."
A job coach told me I needed to let my personality and sense of humour shine through in my cover letters, but I couldn't figure out how to do it. My terrific resume should speak for itself, right? Wrong.
When I got desperate, I decided to write cover letters with the filter off. It didn't seem like anyone read them anyway, so why not? I let myself have fun and wrote letters that were honest, personal, and informal.
I said insanely blunt things, such as: "I'm interested in writing for [press], frankly, because I have read some of your books and, while I found them very helpful, I think I can do better.” (I didn't get that interview, but I stand by my self-assessment.)
"Where were you when I was growing up? I babysat one family just because of all the cool Lego sets I got to build with at their house. [Business] is a brilliant concept and I'm jealous of the lucky kids who get to enjoy it!" (This innovative toy company contacted me right away.)
Sometimes, I felt I'd gone too far after I hit send on an application, but I discovered that the letters that seemed the wildest were also the most likely to get a response. Honesty and humour, with a positive spin, were the magic ingredients for my job search.
When an awesome nonprofit called to offer me a job, I was delighted. Unfortunately, the salary they first offered me was lower than I had expected. Rather than take a salary that would have pinched my budget, I asked for more – and was immediately offered a higher starting pay.
Remember that the salary you start with will be the salary on which they'll base your raises and bonuses. If you hope to stay with the organisation, your starting salary could make a big difference in your earnings over time.
I also asked for a four-day work week, to give me time for my creative work. This was another yes. You might be surprised how many employers are willing to offer flexible schedules to keep a valuable employee — like you — happy.
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