Here’s how to participate in our month-long writing challenge

Robert Skrobe
Dallas Design Sprints
6 min readJun 12, 2019
There’s no need to isolate yourself by candlelight to complete this challenge. We’re here to help.

Are you interested in improving your writing skills?
Want to put your authentic point of view in front of others?
Are you struggling to find time to write anything at all?

Throughout the month of June, I’m inviting my extended professional network (including those I haven’t met yet) to join me on a short-form writing challenge. It’s open to anyone who wants to improve their writing through applied practice.

The inspiration for this event came from a Medium article written by Jake Knapp titled “Go fast to stay authentic”. He was originally inspired by Jason Fried who takes 15–20 minutes to write his own compelling Medium posts. The main takeaway from the article for me was this part:

Speed keeps you authentic. If you’ve got a weird, opinionated, crazy, possibly-stupid-possibly-great plan, and you take a long time to think it through, revise it, and make it perfect, you water down and wash out the goodness.

To that effect, I’m issuing a challenge to you, dear reader.

For all of the reasons you may have to not take part in this (language barriers, lack of something to write about, fear of being judged or rejected, a cognitive disability), there’s someone out there just like you who’s getting it done and sharing their point of view.

What’s stopping you?

Beyond a 30 minute investment to have a shared experience with others, what do you have to lose? What’s the opportunity cost for not trying?

Let’s do this.

Here’s how to participate:

  1. Block off one hour of time per day
    While the exercise in its entirely is clocked at 30 minutes, there’s opportunity to get the editing right, or slightly extend your writing time. Give yourself some breathing room.
  2. Find a quiet room to get this done
    My favorite place to go is the upstairs media room where I normally shoot instructional video for my educational classes. It’s across from my home office, is extremely comfy and walled off from distraction.
  3. Pick your medium
    Some like to write on paper, while others prefer typing it out in a digital document. You may prefer video or maybe recording yourself in a 20 minute podcast. You do you, but choose before you start.
  4. Unless you’re using your phone to capture your thoughts, bury it.
    And I don’t mean digging a hole in the ground and putting it there. I mean putting it under a pillow, or a sheet, or somewhere where it’s not in your vision or within earshot.
  5. Put on some music if it helps inspire/focus you
    For this 20 minute article, I’m listening to a foundational jazz album by John Coltrane called “Blue Train”. Yesterday is was an extended play of “The Game Has Changed” from the ‘Tron Legacy’ soundtrack. Obviously you don’t need this if you’re doing a podcast, but figure out what makes sense for you and run with it.
  6. Set your Time Timer or equivalent for 20 minutes.
    I like using the Be Focused Pro app on my MacBook Pro to keep track of my time. Right now I’ve used about 11 minutes of my 20 and need to step it up to get all of my content in. :)
  7. Start the timer, and begin writing about a topic that’s top of mind.
    It doesn’t have to be world changing or the greatest topic known to humankind. Just pick one and freestyle it. Try not to edit anything during this period. Just type out what comes into your thoughts as they occur.
  8. When time expires, add 10 minutes to the timer and begin editing.
    You can edit grammar, rearrange content, add pictures and give your article a title. For audio and video, you can clip out long pauses, optimize levels, create a title card and export in a suitable format.
  9. Determine which channel your content is best suited for
    You have plenty of options here. LinkedIn, Medium, Instagram, Snapchat, Reddit, YouTube, Vimeo or a host of other smaller but growing media hosting companies that would love to have your content on their network.
  10. Post it
    Don’t overthink this step or second guess yourself. You won’t have a million subscribers sending you hate PM’s or trolling you with sad poop emojis. Just post it, and leave it be for now.
  11. Promote it
    Just because you posted your content on one particular channel doesn’t mean it couldn’t live in other places where you audience might consume it. Check out this article I wrote on how to get your message out on multiple platforms and embrace the wisdom of pillar content.

Wait! I don’t know what to write about!

You might be someone who struggles with choosing a topic, and that’s okay. When you have carte-blanche (i.e. the complete freedom to act as one wishes or thinks best), it can be overwhelming to choose anything, let alone write something compelling about it.

The solution is simple.
Pigeonhole yourself.

In other words, get really granular on something you enjoy doing. It might seem like nothing since you’ve so familiar with it, but I guarantee you there’s someone like me who’s just interested in another slice of life and understanding a unique point of view.

For example, I really like parenting. Specifically, I like to nurture an environment of discovery, acceptance and foundational confidence for my child to live within. I’ve worked at it for seven years, and I’ve learned a lot about myself and the process along the way.

If I were to concentrate strictly on that narrow topic, the subject matter just starts flooding in:

  • How I read with my child during bedtime
  • Why I skipped the crib and stayed in the room
  • Children crave your attention and acceptance, not your iPhone
  • Want your kid to eat more salad? Give them an iPad.
  • When parents treat their kids like products rather than human beings

I could go on, but I could write every single day on those topics. I would also gather both praise and strong criticism from my audience. But ultimately, it’s about having a discourse about what you care about.

The first step in that is starting the conversation through your content.

Hold on! I’m really bad at spelling, grammar or explaining myself.

Some people aren’t that confident with writing in a second language. There’s this weird pressure I’ve been noticing to put content out in the English language online. While it is widely spoken and used, it hamstrings some early writers who struggle with the idea that their thoughts aren’t properly communicated in translation.

If this sounds like you, I have two suggestions for you.

  1. Post content in your native language, and let the online providers auto-translate your material.
    While LinkedIn is experimenting with auto-translation, Facebook and Instagram embed auto-translation into their platforms. Third party solutions (like browser plug-ins and stand alone programs) offer an abundance of options to consume content in other languages.
  2. Post your content on a publication that offers free Q&A
    My own publication here on Medium has a quality assurance program that’s free for anyone posting content here. I don’t monetize, as there really isn’t any need to. It’s really about learning to write, and getting comfortable with the process.

Let’s get started!

Once you’ve created a piece of content, be sure to reach out and let me know about it! We have a Slack channel set up that you can join to network with other writers who are actively sharing their perspective.

> Join the Dallas Design Sprints Writing Challenge (Slack)

Looking forward to seeing you there!

This article is part of the 30 minute writing challenge I’m doing throughout the month of June to help others improve their writing skills. If you liked this article, please consider leaving a comment below, sharing this with others, or simply leaving a few claps to let me know you were here. :)

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Robert Skrobe
Dallas Design Sprints

I run Dallas Design Sprints, The Design Sprint Referral Network and Talent Sprints.