5 Tips to Ease Perpetual Proposal Pain


Freelancing allows you to work from the comfort of your own couch, let’s you choose your own assignments and lunch breaks, and can be done while wearing pajamas. There are plenty of perks. But freelancing is a job, and every job has its downsides. One of the biggest headaches is sending out countless applications, advertisements, proposals, and pitches.

When you freelance, you are your own boss, but you have to find your own clients or you’ll basically be the boss of nothing. This means constantly scouring job boards for work that fits your niche and sending out feelers to potential clients who don’t even know they need you yet. So, as a freelancer you are constantly writing up proposals and pitches, filling out the same info about yourself and what you do while trying to tailor each one to the specific job/individual.

I have to do this even more often than some freelancers because I work on manuscripts (either editing them or ghostwriting them), and even the most seasoned writers usually don’t have more than two manuscripts completed or outlined in a year. So, each editing job I land usually only lasts two months tops (more like two to three weeks for a proofread) and each ghostwriting job, six months tops (and the paychecks are well spread out). To make a solid income, I usually need to have three clients at a time at all times. That means tons of marketing and applying, and it can be exhausting, especially if you don’t use some tricks to cut back on the time consumption.

So, without further ado, here are five tips to ease the perpetual proposal pain:

  1. Templates: This is the big kahuna. If you don’t have a template, you’re going to lag fast and hard. I’m not saying slap a generic template into every pitch or application. In fact, never do that. A generic Dear Sir/Madam in a blind pitch is rightly viewed as spam and your emails will end up in that dreaded folder. The key to making a template that doesn’t feel like a template is to only fill in the things you keep finding yourself saying over and over anyways and then leave blanks for things that ought to be personalized. To do this, you will have to send a few applications and pitches from scratch to see the things that always come up. Obviously, in an application you need a brief paragraph detailing your skill set/relevant background. If you have a niche, some skills will apply to every application you submit. Fill those into a template so you never have to type “I’m familiar with Chicago, MLA, and APA style guides” ever again. With a blind pitch, you should always have a brief section about why the client needs your service and what it will provide them, and then a brief description of who the hell you are. The part of your template that should have the most blanks is the opening paragraph. That is where you personalize the message to the job you are applying for or the person/business you are pitching. It is where you prove that you’ve read the want ad and/or done your research on the accomplishments and needs of the client. Having only one paragraph to fill in is a hell of a lot better than having to type up the exact same sentences over and over and having to worry about proofreading them each time. (P.S. If you aren’t proofreading your proposals and pitches, somebody ought to bonk you on the head like in a V8 commercial.)
  2. Set a Goal: In order to keep up consistent work, you have to pitch and apply consistently. Right around the time I was launching PurpleInkPen, I took up Gina Horkey’s 90 Day Pitch Challenge. (In case you don’t remember, Gina was one of the lovely ladies in my recent Expert Roundup.) Her challenge is to send ten pitches every day for ninety days. I will detail my experience with the challenge at the end of this month, but I can tell you now that having a set number of pitches to do definitely motivated me. You need to keep track of the pitches you send anyway, so one thing that gave me an extra boost was to write out the numbers 1-10 (Or, when I started getting overwhelmed with work on top of pitching, 1-5) in my notebook in the morning. It’s disappointing to see unused spaces at the end of the day, at least to me (I hate wasting lines in my nice journals), so I wrote out the numbers to motivate me to fill in the lines.
  3. Set Aside a TimeThe best way to ensure that you don’t slack off on your pitching is to make it a habit, and one of the best ways to do that is to make it part of your routine. When I first started focusing on pitching, I didn’t have much client work on my plate, so I did mine first thing in the morning, and I made lunch my reward for finishing. Then I did follow ups on past pitches between 3:00 and 4:00 pm and took my puppy to the dog park when I was done. Once the pitches started working (yippee!), and I got slammed with work, I lowered my daily goal and relegated pitching to early afternoon. Setting a time frame made me keep my butt in front of my computer and get the darn things done so I could get to the next part of my day (whether it was taking the moaning and groaning puppy to the park or making dinner).
  4. Apply to What You Want: One of the time-sucking things I found myself doing was applying to anything and everything that even remotely had to do with writing or editing, even if the job sounded like it might lead to chaotic hours, covered a subject I knew nothing about and didn’t want to, or paid less than the rates I had set for myself. Why did I do this? It’s simple. I was worried about money. My husband, who worked overtime while I was in college, is currently going to school for an AutoCAD certification, and it cuts back on his work hours. I thought it only fair that I fully supplement that income he is losing, since he worked overtime to allow me to quit my waitressing job to finish my last year and a half of college. So, I started seeing figures in my head and I panicked. I needed money now, so why not apply to every writing/editing job with a paycheck out there, right? Wrong. Applying to those jobs was time consuming because I often had to add a lot to or completely rework my templates because the jobs were outside my niche. The greatest thing about freelancing is that you choose your own assignments, and I was sacrificing that in a nervous grab for a  paycheck. I didn’t land any of those jobs. The time I spent laboring over those applications could have been spent taking a little extra time to seek out jobs that were a great fit.
  5. Remember the Silver Lining: At the end of the day, if you are a freelancer, your job rocks. Yeah, it can be unbelievably nerve-wracking and you have to put in a lot of effort, but that effort is going toward something you actually enjoy doing. You get to work on what you want, when you want to, and most people at “traditional” jobs can’t say that. When you start to get a headache from all those proposal and pitch submissions, look down at yourself. What are you wearing? I bet it isn’t panty hose or a suit. One time I stopped in the middle of sending an email and realized, “I’m conducting business in a bathrobe with a wet towel on my head.” That was the moment I realized I’m a badass. If you’re a freelancer, you are too. Don’t forget it.

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