Doing the 21-Day Challenge as a Group: My advice

What I love about the 21-Day Racial Equity Habit Building Challenges is their versatility: you can dedicate as much or as little time as you need to the challenge, you can focus on one modality or choose various, you can do the flagship challenge or one of the themed ones, and you can do the challenge alone or as part of a group.

When I’m consulting with an organization that wants to do the challenge as a group, I’m often asked what the best way is of having the group do the challenge together. In my experience, there is no one right way to do it, but this is the process I’ve recommended as a starting point for planning. I then like to work with the group to adapt that process for their own communities.

Prepare for the challenge

  1. Educate your community on what the challenge is. Enlist champions to spread the word. Have a plan for what to say or do if the challenge meets resistance.
  2. Line up your volunteers:
    • Organizers – creating forms, scheduling check-in sessions, monitoring signup
    • Communicators – social media, email, flyers, etc
    • Facilitators – leading check-in sessions
  3. Have people sign up for the challenge using a Google Form or other simple email collection tool (here’s a sample: https://forms.gle/AGiNtR9jS2dnQptz6). Note the survey questions in the registration form.
  4. Give people at least 3 days to sign up, and during that time publicize it widely among your group. Keep an eye on signups and remember to add people to your mailing list even if they sign up late.

Kick off the challenge

Send a kickoff email the day the challenge starts, with something like the following (feel free to copy this!)

Dear X,

Today is the day we’re starting the 21-Day Racial Equity Habit Building Challenge! You’re receiving this email because you signed up to do the challenge with us.

As a reminder, here are the parameters of the challenge:
Every day for 21 days, choose one resource to engage with on the site.
That’s it! 

We have an optional Zoom/Google Meet/Teams/in person check-in halfway through the challenge on XXX date. We’d love for you to join and tell us how the challenge has been going and recommend resources that have stood out to or impacted you. You can register here (link to registration)

Today is Day 1, and while you can choose any resource you like, the curators of the challenge have recommended this activity to orient you. In addition, they’ve created this tracker to help you keep track of what activities you do, and reflect on them as you like.

The 21-Day Challenge can be as casual or as involved as you want it to be. As you move through it, if you have any questions or concerns, please feel free to reach out to XXX.

We are all looking forward to learning together and seeing where this challenge takes our community.

Your org

Work the challenge

  1. Ideally, your group will meet for check-ins at the end of the first, second, and third weeks of the challenge. If not, consider at least a halfway point check-in and/or a pulse-check survey.
  2. Make sure your Zoom is scheduled for the appropriate date(s), or that your in-person meeting room is available, and consider having people sign up for that as well. If you’re using Zoom, there is an option to require registration, and I do recommend that so you know who will be in the room.
  3. The day before each check-in, email all participants to remind them the Zoom is coming up, adding the registration link and reminding them why the check-in is valuable
    • PS The check-in is valuable because we are building a practice of processing difficult feelings in community. It’s valuable to connect with others around an explicitly anti-racist practice as a way to build our empathy muscles. It’s also valuable to experience a brave space for talking about power and privilege without shame.
  4. During the check-in, have facilitators start with conversation norms. Suggested:
    • Nonjudgment of people’s reactions. We’re all on a journey, and this new information is interacting with people’s individual worldviews, experiences, traumas, and relationships in incredibly complex ways. Our role is to hold space for emotions and share resources if asked for. Some helpful phrases (for the facilitator and for the participants) include “tell me more about that” “why do you think that came up for you?” “I hear you” “how does that feel?”
    • Leave the stories, take the lessons. In order to have brave conversations we must feel safe to take the risk. One way to do that is to keep confidentiality.
  5. End the check-in with a quick recap of the things participants brought up, encourage them to continue with the challenge, and ask if you can share the learnings from the meeting with the larger group, not identifying anyone of course.
  6. Consider emailing all participants after each check-in with a summary, particularly if there was anything especially moving or inspirational. Encourage the whole group to keep going with the challenge, and that if they know anyone who is curious but didn’t start with everyone else, that it’s not too late to just start today. Finally, for people who missed the check-in, offer individual time to connect if they want to debrief.

Ending the challenge

At the end of the challenge, send an email congratulating everyone and offering an “exit” survey. The survey would echo some of the questions from the registration survey:


  • Around how many days did you engage in the challenge? (a. 1-5 b. 6-10 c. 11-15 c. 16-21)
  • What would you say is your current level of comfort during conversations about race and racism?
  • Thinking back to your biggest barrier in having conversations about race and racism, how do you feel now? (a. It’s still a big barrier; b. It feels more manageable now; c. other)
  • What do you feel you gained from engaging in this challenge?
  • How likely are you to recommend this challenge to a friend?
  • Suggestions for improving the challenge

The end of the challenge should not be the end of your efforts!

Next steps

A 21-Day Challenge is not just a tool for individual learning. It’s also a tool for community organizing, relationship building, and change making.

Use the pre- and post-surveys to gauge how much learning and growth is happening. Figure out what you want the outcome to be, and measure for that. Remember that change doesn’t happen overnight, and measurable culture change takes time and involves ups and downs.

A lot of what people are learning is serious, and while we don’t want to trivialize it by making it fun, we can make this learning more sustainable by making it fulfilling. Building on the check-ins, keep people connected via virtual or in-person casual meetups, where the topics of conversation are not universally heavy. Encourage a culture of honesty, nonjudgment, and thirst for growth through team building activities, icebreakers, and consistent shifting of the conversation from intellectualizing to feeling and experiencing.

There are enough resources in the 21-Day Challenges that you could do another challenge every 21 days for a year and not repeat a resource, so feel free to repeat the challenge as many times as you like! Here are my suggestions for that:

  • Notice the people who consistently come to the check-ins, and connect with them individually. Ask them to facilitate a future check-in or volunteer in another way.
  • Let people in the community know when another 21-Day Challenge is coming up. Communicate multiple times in different modalities. Let them join late – there’s no “missing the boat” here, we just want people to participate.
  • Notice when resistance to the community engaging in the challenge comes up and what the stated reasons are. This doesn’t mean “harass people if they don’t want to do the challenge!” It means that if there is anyone who is vocal in their opposition to the community as a whole doing the challenge, it’s a good opportunity for a conversation. Give people space in one-to-one interactions to talk about their resistance, and ask questions to help them sort out their own feelings. The goal of the conversation is to hear someone (and ensure they feel heard), and to be able to agree on shared community values. And our message is that offering (not compelling) the challenge is in line with your community values.

There are other options to continue community learning beyond the 21 Day Challenges, too.

  • Regularly scheduled Lunch & Learn or other food + learning opportunities
  • Volunteer opportunities inspired by the Challenges
  • Book club, movie club, or other opportunities to gather and keep the learning going
  • Create a new 21-Day Challenge for your own community or industry. At the end of a challenge, include in the wrap-up email the following question:
    • Are there resources (articles, podcasts, etc) you’d like to contribute to a 21-Day Challenge we make for our community? If so, please reply to this email.
    • Reach out to those interested with a fresh Google Doc or other shared repository for resources, schedule 2 or 3 meetings to discuss what goes into the challenge, and then make a plan to launch that challenge.
  • Use your learnings to review your community’s policies and culture. Knowing what you know now, are there practices that seemed benign before and now could use a tweak? What have you learned about whom to ask, and what approaches to take?

The 21-Day Challenge is a tool – you can use it to launch an entire movement of people ready to talk about power and privilege, motivated to make changes in their own lives, and informed enough to reevaluate “business as usual” in the spaces they occupy. I hope my guide to doing the 21-Day Challenge as a group is helpful as you start this journey.

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