100 proposals in 100 days — Update

Recently I challenged myself to write 100 proposals in 100 days. I’ve been rocking it out every day and I just passed the two week mark on Wednesday!

This is the chart I created to track my progress (back on Day Zero)…


… and here is the latest update, which includes yesterday’s proposal — “day 15”. (I haven’t written today’s proposal just yet).


Last week I shared with you my observations in my first 100 proposals in 100 days update. Here are some observations I’ve discovered in the second week.

Preparation continues to be key. I made that observation in the first update and since then I’ve been trying to start putting proposals together a few days in advance. So I gather a few potential proposal targets (which includes who to propose to and what types of things they might need). I let that info percolate for a couple of days. Then I write the proposal. When I am prepared, the proposal-writing process takes 15 to 30 minutes. When I’m not prepared, it can take up to an hour (perhaps more). The effort of thinking about these proposals ahead of time does indeed take a bit of time but even cumulatively it doesn’t take nearly as much time as when I sit down and try to write something without preparation. So prepare, prepare, prepare!

Writing proposals is a muscle. I used to be a master proposal writer then I kind of got out of practice because I was fully booked. I’m still fully booked but I have the time to take on more work if I want so I’m getting back into the practice. And I find that writing proposals is a type of muscle. It’s a skill that gets sharpened the more you do it. I’m starting to once again think in terms of “how can I work with this person/publication?”.

Ongoing work is easier to pitch than one-time work. This has been my latest observation this week. I’m not sure why that is but it’s holding true so far. In fact, none of my one-time-work proposals have been accepted, whereas a majority of my ongoing-work-proposals have been accepted or are at least perceptibly moving forward. As I write this, I’m speculating that it might be for the following two reasons:

  1. I really have a ton of experience writing ongoing-work proposals but very little experience writing one-time-work proposals. Without realizing it before, I wonder if perhaps there is a subtle difference between the two I had never noticed before.
  2. One-off work is typically magazine work and they have 4-6 week reply times, whereas ongoing work is typically for entrepreneurs and they are fast to reply. So the one-off proposals might still be won but I won’t know until August or September.

On a related note, I’m going to have to start pitching more one-time work because my availability is quickly vanishing. I have a bit of flex but it won’t last. And if I pitch 100 proposals for ongoing work, I’m not going to have the time to do it. So a focus on one-off projects may reduce my close rate on the proposals but it’s a smarter use of my availability right now.

Published by Aaron Hoos

Aaron Hoos is a writer, strategist, and investor who builds and optimizes profitable sales funnels. He is the author of The Sales Funnel Bible and other books.

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