How-To Host A Challenge That Grows Your Biz for FREE

Jenna Kutcher 

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August 29, 2018


Have you ever taken part in an online challenge? Whether it’s a work out challenge, an Instagram challenge, a clean eating, yoga, money or a clean house challenge – there is SOMETHING about challenges that I want to teach about today – because maybe your next big project could be hosting your very own challenge. There’s something about the momentum of doing things as a group, seeing results quickly and the comradery that makes free challenges successful and I want to help you harness the power of a challenge and use it to grow your reach and your profits.

Three years ago, I hosted my first challenge ever. I remember thinking that a challenge could be a good way to teach free content and get people on board with my strategies while also building a community that would allow me to intimately connect with the people I was trying to reach. My first challenge was a 7 day Instagram challenge where I sent challengers a prompt each day today I want to dissect what worked, what didn’t work, what to do if you want to host a challenge and the biggest benefits that challenges can bring to your business!

First: Why host a challenge in the first place?

The #1 reason to host a challenge, in my opinion, is that it’s the biggest and easiest way to grow your email list with people who are specifically interested in learning something that you can teach for FREE. It’s the easiest way to grow your list without hosting a webinar and connects you to the right people while giving you a chance (and excuse) to drop into their inbox or lives on a frequent basis throughout the challenge.

My number one must-have for a challenge is that it is used as a means to grow your email list! Hosting a free challenge that doesn’t allow you to land in inboxes isn’t going to move the needle in your business so if you’re new to list building or looking to grow your leads on a subject that you have an offer for, a challenge can be a huge list builder.

Second: What should your challenge be about?

There are two options here: create a challenge around a topic you’re considering creating an offer around (to test and see how much content you can create and share and how your audience responds to your challenge offer) OR create a challenge that will lead into your pitching a current offer you have. For example: I hosted a 7 day Instagram challenge and then invited all challengers to join a webinar where I would dig deeper into their biggest questions and then share an offer for my signature program The Instagram Lab.

So your challenge can lead into a pitch that sells something or it can be a means of testing the waters to see if you can A. Create an offer around that topic and B. See if your audience is pumped to learn from you! Think about existing offers you have or potential offers you want to create and then decide on a subject that will help you put those eventually in front of the challenge audience (since they will be a warm, aligned audience for you either now or in the future and more likely to purchase!)

Next: Drafting out your content.

When it comes to a challenge, you want to make sure your challenge delivers a result. One of the best aspects of challenges is the ability to get people quick results through committing to something for a certain time aspect. My advice? A 5-7 day challenge seems to be the sweet spot. A lot of people make the mistake of thinking longer is better but think about it: if you host a 30 day challenge, every single day you will lose participants because there is a natural attrition rate when it comes to sticking to something. You want to create something that people can truly commit to and see change if they stick it out without the possibility of making them feel like a failure if they don’t complete it. Most people can commit to a shorter time frame and as a bonus, you get to create less content.

As you plan your challenge think about what the promise is as the end result. If someone commits for 7 days what can they expect the result to be. For my Instagram challenge example, if someone committed to 7 days of following the challenge, I promised them an increase in engagement (because I was confident if they followed through, the tips, tricks and strategies I was sharing would definitely boost the amount of likes and comments on a post – not to mention their follower count!) Paint the end picture and then break down the daily tasks necessary to ensure your participants will hit that.

I would encourage you to give away good content, think about quick wins: things that are easy for your participants to complete that will get them one step closer to that end result. Don’t worry about giving away your BEST content (that will likely be in your offer) but use a challenge as a chance to show people that they CAN learn new things, they can commit to completing something, and they are able to get results based on what you teach. My goal is to lead a challenge that will help qualm people’s biggest fears or pain points that will eventually help them see that you can lead them further on their quest to greater results (which will come through your challenge.)

After you’ve drafted the day to day, how do you deliver?

Now that you have the framework for your challenge broken down by each day that you are going to deliver a prompt, how do you deliver it? You have a few options for this! What I suggest is for sure through email so that you 1.) gather participants email address 2.) they open your emails each day 3.) they can catch up if they miss a day without feeling lost or overwhelmed.

Another way to turbo-charge your challenge is to add a community component whether you have participants post and use a certain hashtag or you make a private Facebook group for people who are in the challenge. I have done both of these and they are awesome in terms of strategy (but more work) because they bring challengers together and foster a community. In my Facebook group, I would post a daily video after the email had gone out and walk people through the challenge and teach a little on that topic. In the end, if I did it again, I would make those videos under 5 minutes and be super specific about what I was sharing, I think my mistake was that I taught SO much in those, it left people with a lot of content to take action on which could have deterred them from purchasing my offer at the end of the challenge because they felt like they still had work to implement before diving into a course.

If you do create a Facebook community for a challenge, make sure you’re prepared to moderate and manage it and then have a plan for it once you the challenge wraps up and how you want to use it in the future (or if you want to close it!)

Now that it’s ready!

Promote your challenge, then promote it again: I’m talking that I want you to get sick of talking about it: post it on Instagram, share it in stories, post it on Facebook, send out an email, I want you to share it high and low (because if you’re doing it right, you’re giving people a FREE challenge that will give them a promised result) I know it feels like you’re shouting from the rooftops but I promise your followers aren’t seeing you talk about it as much as you feel like you are. If you have an ad budget, free challenges convert really well (i.e. cheap) using Facebook ads so it could be a really cool time to reach a cold audience with your challenge offer and then get them onto your list so you can turn them into raving fans. Remember: investing in growing your email list (even if you don’t have an immediate offer) is something that I can’t stress enough.

I recently had one of my mastermind girls reach out to me because no one was joining her challenge and even though I follow her and engage in ALL her content and am active on social media, I hadn’t seen her talk about it even once, thanks to the algorithm and the subtle captions that kind of, sort of gave an invitation. Make sure there’s enough build up to the challenge and then talk about it until you’re blue in the face.


Why a quick win is important

What is one simple thing you could get your audience to do today that they would see results almost instantaneously? Example: the ONE post you need in your feed from The Instagram Lab challenge.

Serve your BEST content up front

Leave them wanting more. You want them finishing the challenge, see your offer and think “If that was free, what does this paid material look like?”

Make sure it’s finishable

While you want to give away your best content for free, you don’t want it to be too complicated, in depth or something they won’t be able to complete in the timeframe of the challenge.

The power of social proof and accountability

Ask your challenge participants to report back on their progress and results. This is where the momentum and viralness can come into play.

Tackle any blocks, concerns or questions within the free challenge

Are there certain mindset shifts that need to happen for someone to want to purchase from you? Do they need any background information or education on why this is important? Work that into your challenge…

In summary, challenges are AWESOME: They are fast list builders, a way to serve your community, an opportunity to get people results and it helps you warm up your email list so that if and when you have an offer to sell them, they are ready to buy because you are a trusted person who’s already gotten the results for FREE! Challenges can be live (as in everyone is working through them at the same time) or automated (set it up once and drip content once someone opts in!) but challenges have grown my list with tens of thousands of leads for FREE and have helped me to understand how I can truly show up and serve the needs of my dream clients in bigger and better ways while creating the perfect offer that they are excited about!

FREEBIE: 10 Ways to Grow an Email List 


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  1. Katelyn Proctor says:

    I listened to your podcast and loved it! Where can I sign up for your challenge?

  2. Ruth says:

    Awesome podcast! Thank you!!

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  4. […] out Build Your Challenge course by Jenna Kutcher. She walks through everything from how to pick a topic, all the way through to […]


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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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