Everything I learned from hosting a 5 day challenge

Everything I learned from hosting a 5 day challenge

October 22, 2017 1 Comment

I recently hosted a FREE 5 Day Holiday Boost Challenge, after seeing the idea come from a few of my peers who had recently run 3 and 7 day challenges for their audience. 

Because we were running close to the holiday season, I thought it would be a perfect time to offer a sales training course that would encourage business owners to launch special holiday offers and use innovative techniques to sell them to their audience and expand their marketing reach.  And, I wanted to grow my email list - because I had finally decided to take email marketing more seriously!

So was born the 5 Day Holiday Revenue Boost Challenge

From beginning to end, I learned quite a lot about this whole multi-day challenge offering - and I want to share EVERYTHING that I learned from the development, the marketing, the delivery and after-math so that you can determine what works and doesn't work in case you want to try this for your business!

Quick & Dirty Takeaway (in case you miss the bulk of this post:)

1) Don't offer a FREE Challenge if you're looking for engagement

2) Do offer a FREE Challenge if you're looking to grow your list

Alright, so that's the highlight - but let's dive into the nitty gritty, shall we?

Development of the Challenge

For two weeks I spread the word about the challenge and plugged it on all of my social media channels.  I decided against spending money on paid Facebook ads because this was a free challenge afterall, and I needed to limit my overhead.  

When I had the idea of the 5 day challenge, I had NO IDEA what I was going to be talking about.  I just decide to do it - and I figured out the agenda the week prior to our launch date.  The only initial details I determined up front were:

  • The challenge would last for 5 days, Monday through Friday
  • The challenge would be free
  • The challenge would be geared toward already established entrepreneurs who had a web presence
  • The challenge would include printable worksheets
  • The challenge would be about SALES and would be related to the holiday season
  • The challenge would include live video trainings every day

There was no more planning than that in the very beginning of my marketing efforts.  The week prior to the launch of the challenge, I developed the actual agenda and worked with my graphic designer to create the accompanying worksheets.  I wanted to make sure that all of the material:

  • Was cohesive and easy to understand, for entrepreneurs at all levels
  • Was branded to Independent She, yet had a holiday vibe
  • Was positive and encouraging of participation and implementation
  • Was doable - and not so intense that it would deter busy business owners who were already overwhelmed with their day to day workload

Systems & Structure

In order to deliver a 5 day challenge to my steadily growing subscribers, I had to figure out a way that would automate as much of the process as possible.  There was no way I could personally email 100+ people with worksheets every day!

Thinkific:  I already use and LOVE the platform Thinkific - it's where I host all of my online courses and digital downloads.  They offer a function called a Drip - where they automatically release certain portions of your content on a schedule that you dictate.  This was perfect for my 5 day challenge! 

So, to setup my 5 day challenge, I set up a "course" on Thinkific and created 5 chapters (for 5 days) and added my worksheets as downloads.  Whoo-hoo - it was the perfect solution for actually hosting the challenge trainings and materials.  And better yet, after the free access period, I added the accompanying live videos and converted the material to a paid product on Thinkific.  So, it worked out in many ways!

Downside:  Once you have the full list of participants, you have to manually enroll every single one of them into your Thinkific course.  When you have over 100 participants, that can be a tedious task!

LeadPages:  Now, when it came to getting people to signup for the 5 Day Challenge during my two-week marketing blitz, I designed a holiday-themed LeadPage  that was allowed people to signup to the free challenge using their email address.  I found the count-down clock option to be very beneficial, as it counted down to the start date of the challenge which provided a sense of urgency for sign-up (a great sales tactic!).  You can see the lead page here - it had a conversion rate of 45.78% which was pretty awesome!  

Facebook Pop-Up Group:  When it came to actually hosting the live trainings, I knew that I would host them on Facebook, because it was easy and convenient to everyone who would enroll.  I first considered creating an event on my Facebook page and going live there everyday; but, decided against this because I wanted to capture email addresses of anyone who was interested.  If I created an event, it would allow people to come in that didn't sign up.  So, I created a pop-up Facebook Group designed specifically for the 5 Day Challenge and invited all participants to join us. 

It worked out very well for the challenge, as it gave me the ability to go live - but even better, offered the opportunity to encourage conversation and engagement for all the members! This was by far my favorite part - getting to know everyone, hearing how they were navigating the challenges each day and offering encouragement as they made breakthroughs and pushed past challenges.  We all decided to keep the group open after the challenge period was complete because we all enjoyed the camaraderie!  

Downside:  Adding members to a Facebook group is not so easy, because the email address participants used to enroll in the challenge wasn't always the email address they use on Facebook. It's also a manual process of adding emails and inviting them all, one by one!

eCamm Live:  I love this service, because it allows for video streaming through Facebook while offering the ability to add text and image overlays on the video - as well as offering the ability to do screenshares and more!  So every night I hosted the live trainings, I used eCamm live and was able to connect with everyone while also showing them examples and live demonstrations on my desktop.  

MailChimp:  A big factor in creating this free challenge was to grow my email list, so it only made sense that I would use an email system to help manage it all and communicate with participants. 

I setup a schedule to email all participants the week prior to the challenge to let them know about how the challenge would work, where to find the Facebook group, etc.  When the challenge started, I sent emails out every morning to announce the release of that day's challenge and reminders for them to join us on the Facebook group.  I also sent out messages towards the end of the challenge week, as well as a few days after the challenge was over, about special offers I was extending to the group as well.  

I definitely saw a dip in open rates towards the end of the week, but that's ok.  By day 4 or 5 of the challenge, they were used to seeing my alert that the material for the day was ready.  I also had a total of 2 unsubscribes from that list of people who didn't participate in the challenge, access their courses or want to participate any longer (which is fine!). 

By the end of the challenge week, my data was showing me that about 30% of the people who signed up for this challenge were actively interested and participating - which is great!  These will be the folks I continue to email and build relationships with after the campaign is complete - people I wouldn't have found or known otherwise, and were all my ideal client.

The Challenge Period

The bulk of the work for this initiative was the two preceding weeks of marketing and material development.  It was a lot of work!  Once the first day of the challenge had begun, it was really just a matter of showing up every evening for the 30-minute live training on Facebook and engaging with all of the participants in the group.  I will say that it was challenging to push myself to go live every day, especially at 8:30 at night after putting my toddlers to bed.  But, that's ok - it was a challenge that was totally worth it!

There was a lot of really great feedback from those who participated in the challenge and I was overwhelmed by the sense of community that was created through this initiative.  The only "downside" I found was that the challenges offered seemed to be too intensive for some to absorb and implement on a daily basis for 5 days straight.  If I were to do another challenge in the future, it might be capped at just 3 days instead of 5.

Special Offers

I decided to offer the group of participants a couple of special offers at the end of the challenge, to continue the participation lifecycle and continue to highlight the people who were truly interested in becoming a client. 

I offered a $1,000 Scholarship Giveaway to the participants who completed all of their worksheets and scanned them over to me at the end of the week.  I also offered the full group the ability to become an affiliate partner of our courses, and receive 25% of all referrals they sent over.  This encouraged their participation in our brand while showing them that I wanted to continue to partner with them!

Free vs. Paid

Let's get back to this point mentioned in the beginning of this article.   Because this was the first time I had ever offered any sort of multi-day challenge or drip campaign, I wasn't at all sure of what to expect in terms of engagement, participation, etc.

I have always heard (and it's TRUE), that if you offer a FREE event, you will have significantly lower participation and show-up rates than you would if they had paid.  Why is this? Because if someone pays for something, they inherently feel as though they need to follow-through in order to rationalize their payment.  It's basic consumer psychology.  

If your goal with any initiative is to gain emails - then FREE is the way to go.  If your goal is to get more people to show up (which might be more relevant for in-person events), then require payment.  Even if the price is just $5 or something pretty low, the sheer fact that they paid means that they are much more likely to show up.

Overall Takeaways

Will I do another free challenge?  Maybe.  It was a LOT of work, and although I achieved my objectives I'm not sure that I'll be doing it more than twice per year.  

What was the best part of hosting a challenge?  Meeting so many new people!  The community we built of engaged, like-minded business owners on our Facebook page was remarkable - and they're all relationships that will be maintained long-term.

What was the most challenging part of this process? The preparation and development of the materials, the emails, manually importing all participants, etc.  In terms of time, it did have quite a bit of expense.  The fact that I was able to convert it to a paid product after the free 5 day challenge part was for sure the saving grace!

Biggest piece of advice for anyone considering their own challenge?  Define your goals upfront!  Don't go into this blindly or without an overall strategy.  If your goal is to make money from a challenge, you'll have to structure it differently and market it differently.  If your goal is to grow your list, you'll have to lower your expectation of participation rates.  Just be clear about your goals ahead of time, so that you can strategize it appropriately and manage your own expectations once you see how the challenge is performing.


I'd love to hear your thoughts on multi-day challenges, free events and other campaigns that are designed to qualify new leads, grow your list or land potential new clients. What you have found that has worked for you?  Have you ever considered hosting your own challenge?  Comment below and let's talk more!

1 Response


October 25, 2017

I learned so much from your experience. Thank you for sharing. I’m planning a free challenge for 2018, and it is a lot of work. Like you said, I will probably only do one or two a year as well to build my email list as well. Again, thank you for sharing! And I’m loving everything your’re doing with your brand.

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