Why Freelancing Feels Like a Bad Boyfriend

I’ve been freelancing for six months now and though I had no idea how I would react to being self-employed, I’ve mostly loved the ride. Some days it’s a pleasant drive on a breezy day; other times, it’s like being on a rollercoaster for eight hours straight.

It might sound crazy to say this, but sometimes freelancing does feel like a bad boyfriend! Fellow freelancers, how do you feel about freelancing?

But the best way to describe freelancing is by comparing it to the cute boy you always had a crush on. He was popular, athletic, perfect on paper. But what he had in good lucks, he lacked in stability.

Freelancing is fickle. Some days I feel like not only am I creating a new life for myself, but I’m also making a statement for all female entrepreneurs. Other days I feel like napping all day and feeling sorry for myself (I have done this…several times).

Sometimes everything is going well. You’re getting compliments on your work, new clients are finding you on LinkedIn and people are paying their invoices within 2 days.

Other times it’s like every editor’s job is to drag you down below the depths of where your self-esteem wants to go. It seems like nothing you write is good enough, that no idea you have works and that your dream publication has blocked your email address.

Solution: Everyone has their own opinion. What works for one editor might be total garbage to another, but that doesn’t necessarily reflect on you. Some people have higher standards, yes, but other editors have specific guidelines to meet and their own bosses to appease.

Just because someone didn’t like what you wrote doesn’t mean you’re a terrible writer or that you have no future in this business. It just means you’re not a good fit for them. The good news is there are 1,287 other companies you could be writing for and haven’t pitched yet.

When I get really down about five rounds of edits from one client I start thinking that maybe I’m not good enough and then I remember some editors are picky some voices don’t match and sometimes if someone is really annoying, I think, “Why do I keep banging my head against the wall trying to work with this client?”

Solution: Sometimes people aren’t a good match – that’s all. It’s like dating a great guy, but knowing he’s not the right person for you. There’s nothing wrong with him or with you, but you’re not just right together.

I’ve had moments where I’ve connected with an editor I really like. The emails are going great, you ace the phone interview and then you find out that they’re offering you peanuts. It feels like you’ve wasted hours of your time trying to sell yourself, only to find out they practically want you to write for exposure.

Most of the time I’m angry that someone thinks so low of my work. But sometimes, I start thinking, “Well, maybe I should just lower my standards a bit. After all, a gig is a gig.”

Solution: Many of my freelance friends know me as the person who will ask for a higher rate at all costs. Once, a publication said they were offering $50 a post, and I replied that my minimum was $150. They agreed to the higher rate.

When I get tempted to take a low rate, I think back to all the lessons on negotiating and asking for higher rates that I’ve had throughout the years. Making room for a crappy client leaves no room for pitching and prospecting to find a better one.

One of the hardest parts of freelancing is doing a good job on a project or application only to be rejected by a potential client. This is usually a big reason why I end up taking three hour-long afternoon naps and eating gummy bears for lunch.

Solution: The key to not getting too upset at any one time is to have so many irons in the fire that you’re not worried about any one particular rejection or approval. Sure it’s great if you got a gig that you’ve been working on or a pitch that you love was accepted, but when you’re so focused on getting one in particular, you can lose perspective.

When I told my mom how I was worried about an anchor client cutting their freelance budget, she asked me if I was looking for new clients. I told her that I’m always looking for new clients.

I’m not casually sitting around waiting for emails to come through. I’m always pitching new people, keeping an eye out on job boards and finding new companies to contact. Doing this on daily basis means that even when I lose one client, I’m likely on my way to gaining another.

As stressful as this life can be, and it’s definitely made me consider raising my anxiety medication, I’m so much happier with my choice. I get up at 10 a.m., work when I need to and live in a city I love. If that isn’t worth putting up with a bad boyfriend, I’m not sure what is.


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