Template: 5-day challenges that convert free members to paid

A free 5-day challenge gives people one short task a day for five days. On day 5, the last day of tasks, you open your paid community to everyone who took part. They then have until the end of day 7 to join at a founding price, and after day 7 the challenge space closes. So the whole thing runs for a week: five days of tasks and two days to decide.

That deadline is the reason a challenge brings in more paying members than a free tier. Someone on a free tier can stay there for months without ever making a choice. Everyone who does your challenge has two days to decide whether to keep going with you.

Three things affect how many people join more than anything else. Mention the paid community on day 1, so nobody is surprised when you open it on day 5. Run a live session on day 1 and on day 5. And give the founding price a deadline. For a benchmark, look at virtual summits, which are the same kind of free event run for bigger audiences. Krista Miller, a virtual summit and online challenge strategist who runs Summit in a Box, said in a Heartbeat office-hours session that summit hosts aim for 8 to 15% of free attendees to upgrade: "We're usually aiming for anywhere from 8 to 15% of people upgrading to that all-access pass."¹

Below are seven templates you can copy: the plan for the week, the invite, the day 1 welcome, the daily prompt, the day 5 invitation, the last call and a note for people who aren't ready to join. The parts in brackets are where your details go. Change the rest of the wording until it sounds like something you'd write, because people on your list know how you normally talk and will notice if it reads like a template.

What every challenge needs

• One problem for one kind of person. "Write your first sales page in five days" tells someone exactly what they'll have at the end. "Grow your business" doesn't, so fewer people sign up and fewer of them finish.
• A shared start date. When everyone starts on the same day, the channel fills up with people working on the same task at the same time. Quieter people are more likely to keep going when they can see others posting their results.
• A task a day that takes about 15 minutes. Each task should produce something people can post, like a draft, a photo, a list or a number.
• Two live sessions. A 30-minute kickoff on day 1, and a session on day 5 where you answer questions, share what people made and open the paid community.
• The paid offer, mentioned on day 1. Liz Wilcox, an email strategist and keynote speaker, tells new subscribers in her first emails that she'll be selling to them: "I am going to offer you free and paid products."² If people know from the start that an offer is coming, the day 5 invitation won't feel like a bait and switch.
• A deadline on the offer. For example, a founding price that ends 48 hours after day 5. Without a deadline, people who mean to join put it off and then forget.
• A closing date. Challenge access ends after day 7. If the challenge space stays open, it becomes another free tier, and people no longer have a reason to decide.

The week, day by day

The challenge itself is five days of tasks. Days 6 and 7 give people who missed the day 5 session time to catch up, and they're the window for the founding price.

Before: post the invite every day for a week. Close sign-ups on the morning of day 1.

Day 1: 30-minute live kickoff. Send the welcome message and task 1. Tell people what the paid community is and that you'll open it on day 5.
Day 2: Task 2. Share one member's result from day 1.
Day 3: Task 3. Ask everyone to post their progress so far.
Day 4: Task 4. Show what members get inside the paid community.
Day 5: Task 5. Live session: answer questions, share results, then open the paid community with a founding price.
Day 6: Send a reminder to anyone who missed the live session.
Day 7: Last call. The founding price ends tonight, and challenge access closes.

The invite

Post this every day for the week before the challenge starts: in your newsletter, on social media and anywhere else your audience already hears from you. Close sign-ups on the morning of day 1.

Free 5-day challenge for [who it's for]: [the result] by [date].

You get one task a day, and each one takes about 15 minutes. We start together on [start date] with a 30-minute live kickoff, and we finish on [end date] with a live session where I answer your questions.

The challenge is free. At the end, I'll invite you to join [community name], my paid community, if you want to keep going.

Join here: [link]

The day 1 welcome

Send this the morning of day 1, before the kickoff. It explains how the challenge works, gives the first task and mentions the paid community once, plainly.

Welcome to the challenge, [first name].

Here's how it works: one task a day for five days, about 15 minutes each. When you finish a task, post your result in [channel] so the rest of us can see it.

Today's task: [task 1].

One more thing, so it isn't a surprise later: on day 5 I'll open [community name], my paid community, for anyone who wants to keep working on this after the challenge. You don't have to join. You get the whole challenge either way.

See you at the kickoff at [time].

The daily prompt (days 2 to 4)

Use this for the three middle days. Naming one member's result from the day before shows everyone what a finished task looks like.

Day [n]: [task].

Yesterday [member name] [what they did]. That's exactly the kind of thing to aim for.

Post yours in [channel] when you're done. If you get stuck, reply here and I'll help.

The day 5 invitation

Send this on the morning of day 5, a few hours before the live session, so people can read it and bring their questions.

That's day 5, and you've finished all five tasks.

If you want to keep going, [community name] is open from today. Inside you get [three things members get], and every week [what happens every week].

The founding price is [price] a month for anyone who joins by [day 7 date]. After that, it's [full price].

Join here: [link]

I'll be live at [time] today to answer your questions.

The last call

Send this on day 7, the last day of the founding price. Quote one member's result instead of describing the community again, and ask them on day 5 or 6 if you can use their words.

Last call: the founding price for [community name] ends at midnight tonight.

[One member's result from the challenge, in their own words.]

If you'd like to join, here's the link: [link]

The challenge space closes tomorrow. Thank you for showing up and doing the work this week.

The "not yet" note

Send this after the challenge closes to everyone who didn't join. Plenty of people come to two or three free events before they join anything, so keep them on your list and tell them when the next challenge starts.

Not ready to join yet? That's completely fine.

I'll send you one useful thing a week by email, and I'll let you know when the next challenge starts. [Link to join the list]

Adapt it to your niche

The plan and the messages stay the same for every niche. What changes is the five tasks. Pick five steps toward one result that your paid community keeps working on, so people who finish the challenge can carry on with the same work inside it.

• Fitness coach: five short workouts and one habit to track, with a form check in the day 5 session.
• Business coach: one section of a sales page each day, with the finished pages reviewed live on day 5.
• Wellness practitioner: a different evening routine each night, and a short reflection posted the next morning.
• Creative teacher: five prompts where each one builds on the last, ending with one finished piece.
• Professional community: five tasks toward one concrete goal, like an updated portfolio or a first pitch to a client.

Run it on Heartbeat

1. Create a free Sign Up Link that adds people to a Group called something like "5-Day Challenge". Make the Group Admin-controlled and give it its own private channel.
2. Add a five-lesson course that the Group can access, and schedule each lesson to publish on its challenge day. That way everyone gets each lesson on the same day.
3. Schedule two Events, the kickoff on day 1 and the live session on day 5, and invite the Group. Set the email invitations to Medium.
4. On the morning of day 1, delete the Sign Up Link so nobody else can join. Then run a one-time Workflow for the Group: the welcome goes out straight away, followed by the daily prompts, the day 5 invitation, the reminder and the last call at delays of 1 to 6 days. Each delay counts from when the Workflow starts, not from the step before it.
5. Create your paid Offer, and a promo code for the founding price that only applies to that Offer. Set it to expire on day 8. Promo codes expire at midnight, so the founding price ends when day 7 does.
6. Add a final "Remove from group" step to the Workflow at 7 days. Choose both the challenge Group and the course's own group, which has the same name as the course. This step is what closes challenge access.

Before you open sign-ups, check that your paid channels, courses and Events are limited to your paid Offer's groups. Anything you've opened to every member will be open to challenge participants too. People removed from the challenge Group stay in your community as members, so they still count toward your plan's member limit.

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