Running Challenges on Substack

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00:08 Running Challenges on Substack

00:31 Case Study: Jeannine Ouellette's Story Challenge

01:06 The Role of Paywalls in Challenges

01:47 Different Approaches to Challenges

02:45 The Power of Free Challenges

03:17 Transition to Workshops


Running Challenges on Substack

[00:00:19] Challenges can work well for different types of Substacks.

[00:00:23] Challenges can be really clear paid offerings that keep subscribers and convert paid subscribers.

Case Study: Jeannine Ouellette's Story Challenge

[00:00:31] One of my clients who does challenges very well is Jeannine Ouellette. She has great success with them. This is her story challenge. In her case, this is running for 12 weeks. It's for paid subscribers. Each week she posts something about writing stories. In week two, it's writing character. In week three, it's writing place.

[00:00:52] In this case, its beginnings. Free subscribers still get a lot. They get an entire post on the topic [00:01:00] for that week's challenge. But to participate I have to become a paid subscriber.

The Role of Paywalls in Challenges

[00:01:06] This is important because at the paywall I'm told what's below.

[00:01:10] This is where paywalls work very effectively: when we tell our readers what's down there, instead of just hitting them with a paywall, just something to think about in how you lay out your challenges and where you put the paywall.

[00:01:24] Below the paywall, she goes more in-depth in the topic for that week and then she gives you a very clear exercise for that week and invites people to share in the comments. She has 360 comments. People are doing the exercise, posting the exercise, which she keeps very short. Everyone is commenting on each other's.

Different Approaches to Challenges

[00:01:47] This does not have to be for writing only and you don't necessarily have to do it so that the comments are paywalled.

[00:01:54] Shira Gill for the No New Things Challenge, she offers pretty much the [00:02:00] whole challenge for free in one post and then offers bonuses for paid subscribers, including a motivational video kickoff call, a printable challenge workshop, a planner, and weekly checklist. To get these, you have to become a paid subscriber.

[00:02:17] John Crickett does his challenge on more of an honor system. He asks for paid support, but payment in different ways: you can refer a friend or a colleague to the newsletter, sign up for a paid subscription, buy one of his courses, or sponsor the newsletter. Sponsorships are something that people in tech do quite a bit, less so in other categories on Substack. He gives the entire challenge to everyone.

The Power of Free Challenges

[00:02:45] Michael Easter: his diet challenge was completely free. However, it brings me to his website, which will draw my attention to some of the other things that he sells, like his books and then other aspects of [00:03:00] him and his career.

[00:03:01] John Halbrooks does the Beowulf challenge in which he takes people through a reading of Beowulf.

[00:03:08] Those are just a few ways that you can do challenges. As I said, if you do want to do them as a paid offering, it works very well and converts very well.

[00:03:17] Next we'll cover how to run workshops on Substack.