Challenges, Not Chores

We’ve all been there: the task that you keep meaning to do, you keep putting off, and each time you procrastinate, you dread the task more.

After my book was published, I did a few refreshes of old popular posts, and then over the next year I wrote exactly… two… new posts.

I’d put off writing for so long that all I could associate with writing was the guilt I felt for not getting it done.

When that happens – whether the task is writing posts for your personal blog or interviewing customers or reorganizing your cluttered Dropbox folders – a good way to unblock yourself is to set yourself a challenge.

At the beginning of June I got tired of week after week, not having a “good enough” blog post to make up for so many weeks of silence. So I set myself a goal to publish a post for every weekday in June.  And I did.

The pragmatic details:

  • I didn’t tell anyone I was going to do a post-a-day month. (Recent social psychology research suggests that, when you tell people your aspirational goals and they acknowledge them, your brain feels satisfied like you’ve already completed the goal — and thus, you feel less driven to actually do it.)
  • I used the Habit List app on my iPhone and set a reminder to buzz me at 9:30 pm (once kids are in bed) every Sunday through Thursday.
  • I repurposed a number of emails and tweet replies as the basis of blog posts.

I’m not going to keep up this pace of publishing. While I’m happy with the quality level of this month’s posts, I’m not sure I could maintain this. More importantly, there are other goals I’d like to shift focus to. I’m going to aim for posting twice a week, and I’ve updated my Habit List reminders to reflect that.

Give Your Emails a Friend Check

Yesterday I wrote about the “busy sidewalk test” as the easiest way to check out your outreach emails for brevity and simplicity.

But even when walking down a busy sidewalk, it can be hard to notice if the words you’ve written contain some accidental tones or nuance. After all, they’re your words! You’re familiar with them; you have the context in which they were written.  Your audience doesn’t.

So now it’s time to phone a friend. Or, er, email a friend.

  • “But my friend isn’t part of my target market!”
  • “But I don’t have any personal friends who have the problem I’m trying to solve!”
  • “The only people I know who know about this industry are other people in my company!”

Doesn’t matter. This is a very simple favor to ask.

Simply email or text a friend and say “I’m about to send you an email. When you read it, pretend it’s not from me but from someone you don’t know.”

Then send your email to your friend.

Then ask your friend these questions:

  • Were you unclear on what the email was asking you to do?
  • Did it sound sketchy or spammy in any way?
  • Did it sound like the email was maybe trying to sell you something?

If the answer to any of these questions is “yes”, you have some rewriting to do.

(Note: writing effective outreach emails is hard, and for many folks, it can feel like “it’s taken me hours to write this email, how much longer is customer development going to take? maybe I should just give this up and crank out some code.”  Don’t give up!  It does take a while to get your email style working effectively for you. But once you do have a good email, it’s a template that you can adapt and reuse for years.)