Remember that one cool thing you just had to have when you were younger? A Super Nintendo, a pair of Air Jordans, that rad Teenage Mutant Ninja Turtles sleeping bag?

Now imagine there two scenarios in which you could get your hands on it. Which one will be more gratifying in the long term?

Scenario 1: Surprise! You find it wrapped up amongst other gifts on your birthday or on Christmas morning.

Scenario 2: You do chores for a few weeks, mowing the lawn and cleaning the house for extra allowance money. Then, you buy it yourself.

If you guessed #2, you’re right.

Even something as silly as a Teenage Mutant Ninja Turtles sleeping bag will mean far more to you if you’ve invested time and money to get it for yourself.

Of course, everyone likes to get free stuff, and (most) people like surprises. They make us happy! And certain gifts do maintain a lifetime of importance, like engagement rings or sentimental family heirlooms.

In general, though, we tend to value the things we have to work for over “unearned” gifts. The New York Times reports on a study that found “that even when good things occurred that weren’t earned, like nickels coming out of slot machines, it did not increase people’s well-being.”

So. Let’s translate that to your audience, your readership, your future students.

If you want them to value what you have to offer, invite them to “work” for their place in your course instead of handing it to them, free and gift-wrapped.

One powerful way to do this is to set up a mini “obstacle course” that weeds out the disinterested folks and builds a strong connection with your best readers.

Think of it as a sort of adventure or journey that you invite your audience to take. Those who can complete it have proven that they’re truly invested.

After all, you’re not aiming to have every denizen of the Internet in your community, are you?

You wouldn’t promote your custom wakeboards to senior citizens with bad hips. And you wouldn’t try to get hipster kids to buy your medical alert button (maybe ironically).

Your obstacle course ensures that you’re getting self-selectors – people who are making a conscious choice to participate. And that’s what you should aim for – customers who are committed, passionate, and easy to handle. (Read more about why you should avoid troublemakers.)

Here are a few challenges to put in your readers’ obstacle course. The challenges aren’t that difficult, but they give your best readers a chance to rise to the top. Hey, maybe they’ll even buy you that sleeping bag if you ask nicely!

The “Sign Up” Challenge

Get your readers to sign up for your email list.

Difficulty level: ★★☆☆☆


  • This is the #1 most important challenge to start with. You’ll want to give your readers ample opportunity to complete this challenge.
  • Display your email sign up form prominently on your website.
  • Add a pop-up or lightbox form as well.
  • Include a “sign up” call-to-action within all of your blog posts and other content.
  • Look into a software solution like Leadpages that makes it incredibly easy to collect sign-ups.
  • Entice readers to sign up by offering free carrot content in exchange.

Real life example:
Are you enjoying this article so far? Get more insights from Summit Evergreen delivered to your inbox weekly. (See what we did there?)

The “Tell Me More” Challenge

Collect more data from your readers.

Difficulty level: ★★★☆☆


  • Your email sign up form should have as few fields as possible to make it easy for people to opt in. Now, it’s time to gather more info.
  • Build surveys that ask for demographic stats that are relevant to you. Perhaps you’d benefit from knowing your reader’s zip code, gender, or how they heard about you.
  • Also ask questions that require some personal reflection.
    • Create a menu of all of your course offerings and ask readers to pick which course they’d want to take right now.
    • Ask them what one thing they want to learn about that you don’t currently offer.
  • These questions will provide you valuable insight and get your reader to consider signing up for your course.

Repeat offender:

  • Once your readers have met this challenge, ask them to do it again! Just don’t go overboard asking too many questions. Pace yourself, and the “Tell Me More” Challenge will become a recurring part of your relationship.

The “Make A Choice” Challenge

Force your readers to make choices.

Difficulty level: ★☆☆☆☆


  • Always give your readers two options instead of one. Here’s why:
  • When we ask you “Do you want a cookie or a cupcake?” it doesn’t really matter what you answer. Whatever you choose, now you’ve got pastries on the brain – and if we’re selling pastries, that’s our goal!
  • One of the simplest choices you can offer is between “Carrot Content A” and “Carrot Content B” when your reader opts in to your email list. It’s a small decision, but forces your reader to participate and forge a connection with your content.

Expert advice:

The “Speak Your Mind” Challenge

Encourage your readers to become vocal members of your community.

Difficulty level: ★★★☆☆


  • People love two things: sharing their opinions and talking about themselves. (And bacon. So, three things.)
  • Invite your readers to speak their minds. Include calls to action in your blog posts, Facebook posts, and tweets.
  • Respond to people who respond to you. If someone comments, always reply and let them know they were heard. It will encourage them to speak up again.

Advanced obstacle:

  • Ask your readers to not only engage with your content, but to share it with others. It can be as simple as a retweet or as deliberate as forwarding your email newsletter to a friend.

The “Pay For It” Challenge

Ease your readers into their first paid purchase.

Difficulty level: ★★★★☆


  • Perhaps the most difficult obstacle of all is transitioning your reader into a paying customer.
  • You can’t force someone to complete this obstacle, but you can put all the pieces in place for it to happen.
    • Push out fantastic content that’s relevant and fun to read.
    • Cultivate your personality and brand so that readers identify with you.
    • Show off your product and what it can do to help your readers with their challenges.
    • Make it easy to purchase when the time is right.
  • When someone completes this challenge – congrats! Now you’ve got a committed customer.

Imagine the exhilaration of completing your first 5K or marathon. Your heart’s pumping and you’re filled with an incomparable sense of accomplishment. You overcame obstacles to achieve something amazing! Now, all you want to do (after you sleep for the next three days) is try it again.

That’s how your readers should feel with every challenge they complete in your obstacle course. The high of accomplishment, followed by the urge to come back and do it again.

How do you keep them coming back? By being their proud coach, standing at the sidelines with a bottle of Gatorade and a lot of encouragement to keep going.

By the time your readers accomplish all of the challenges you’ve set for them, they’ll be proud participants in your learning community. Running your obstacle course will be a rite of passage. And you’ll find yourself with a dedicated, passionate team running alongside you.

It’s fast and easy to create your first online course. Start your free trial of Summit Evergreen by clicking here.

About the author: