Laura recently told us “Invoices. Loathsome, vile creatures. I hate doing invoices more than anyone I know.”

At that moment, I realized why we had not received an invoice from her in a while. So we asked that she write an article on this that would perhaps help her get over her fear of invoicing.

Laura’s Story:

The following is a true story. I worked on a website project, writing copy and coming up with catchy product names, for a month. I did the work; my people were happy. And then I just didn’t invoice them. For like four months. Look at the ridiculous time lapse in this email exchange:

What is wrong with me?! Did I really go four months without sending an invoice, to the point that the client had to prompt me for one? And don’t you just love my flimsy excuse, that “I kept forgetting”? And look how nice my client was, apologizing if they missed seeing the invoice. Umm, no you didn’t miss it, I just didn’t send it.

I have a serious invoicing problem. I don’t enjoy it. Given the evidence above, one might assume that I would rather work unpaid than send invoices. This kind of behavior as a freelancer is beyond unprofessional, and worse, it’s literally making me poorer than I should be.

Thankfully, everyone I work for is kind and respectful and has requested an invoice when I don’t send one. If they didn’t prompt me and I never got paid, could I blame them? Certainly not. As a freelancer, it’s on me to track hours and send the invoice. (If a client doesn’t pay an invoice…well, that is a problem I will face when it comes. For now it hasn’t happened.)

In what could be considered a mini-intervention, Jason Long, curator of this blog and founder of BrainLeaf, JHMG, and current CEO at Tangent Solutions told me I had to change these bad invoicing habits immediately. If I wanted to grow my copy writing business, I needed to be able to manage tracking hours and sending invoices. I needed to make sure I got paid for the work I did.

So I bought the cheapest FreshBooks plan. I started being diligent about logging my hours. Invoicing is significantly easier (before I was doing everything manually, as in building tables in Word and tallying up my hours on my laptop’s calculator). But still I don’t enjoy it.

Of course, I love receiving payments. Ooh, money! That’s a thing I use a lot of! It’s the requesting to be paid part that I don’t like. I think there’s some deep-seated revulsion of having to ask for money, possibly even a fear of rejection—of someone not being satisfied by work and refusing to pay—that makes me dread invoicing so much.

I asked around The Quad Co. in Athens, Ga., where I spend many of my working hours, if anyone else ever had invoicing problems. Matt D. Smith, a designer (AKA “The Quadfather”) told me, “If you’re having problems invoicing, then there’s probably a bigger problem you’re not addressing.”

This bigger problem might be a fear of rejection, a symptom of social anxiety. These fears and anxieties can hinder many people in a range of situations, according to this study in Personality and Social Psychology Bulletin. Study authors Thomas Langens and Julia Schüler tested a solution for people struggling with anxiety, called “written emotional expression.” Writing about a stressful experience, they argue, helps to understand why you feel anxious about something. That deeper understanding can decrease negative feelings. Hmm. Perhaps my own anxiety about invoicing could be lifted if I wrote about it more. Which is why I’m writing this right now. So meta.

I am also convinced from personal experience that a freelancer’s anxieties originate in 9-to-5 culture. My working life began with a day job at an alternative energy coop that promoted corn producers in the then burgeoning corn ethanol industry. (I was 17 at the time, and all I remember is reading Harry Potter in between answering the office phone.) My regular paycheck never required an invoice. I had to “clock in,” but I didn’t have to send an invoice. I also received the same paycheck every two weeks, so the amount was never in question. I know there are different ways to structure pricing, which Jason writes about a lot on this blog. And while I’m not married to hourly pricing in the long-term, in the short-term it’s my only option. I know setting up automatic payments and retainer contracts could be a really good way for me get rid of my problem with invoicing. But I think the real problem I have with invoicing can be traced to insecurities I feel about being a freelancer in the first place, which stems from my parents both having really secure, full-time salaried jobs when I was growing up. And then I got jobs with “regular paychecks” while in high school and college. Because of freelancing, I’ve had to reformat my orientation to the working world, redefining for myself what it means to have a job, to identify as a person with a job even though I’m self-employed. I know I am not the only unique snowflake and that there are lots of freelancers figuring this out or who have already figured it out, but it remains an issue for me.

I am on a path towards better invoicing habits. Now, I set deadlines for myself to send out all invoices by the end of the month. But it is still a struggle! Because the work I do has variable hours each month, I can’t use automatic payments. That means I still have track my hours every day for every project, create the invoice, make any revisions, or add credits if I need to. True, it only takes about five minutes out of the day. But it’s five minutes I would rather be doing things like, composing a tweet or editing a blog post. Anything but invoicing.

I know there are a few alternatives to doing invoices myself. I could hire someone to manage it for me. Or I could move to a service as product model. Or get a “real” job. Those options each have their own appeal. But I’m not there yet. The best solution for me right now is simply being disciplined. Tracking hours religiously. Having a set day to create and edit invoices. Sending out invoices by a monthly deadline. I am hoping that being more disciplined will eliminate some of the anxiety I have about asking people for money.

In the meantime, someone please tell me I’m not the only freelancer who struggles with invoicing.

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Laura Leidner is a freelance writer who spends a lot time around startups. You can find her on Twitter @laurablorah.