How to Create a Wellness Challenge Employees Look Forward To

Think about the last workplace event employees genuinely looked forward to.

Not one they attended because they were supposed to. Not one they joined because there was a gift card attached.

One they were actually excited about.

People talked about it beforehand. They invited coworkers. They anticipated it. When it was over, they talked about doing it again next year.

Now think about the last wellness challenge you launched.

Did employees ask when registration would open? Or did they ask how many points it was worth?

That distinction matters more than it might seem.

Many wellness challenges are designed as if participation is a reward problem. If enrollment is low, add more points. Increase the prize. Offer a larger premium discount. Make the incentive more attractive.

But participation isn’t primarily a reward problem. It’s an experience problem.

When a challenge is built primarily around rewards, employees learn to participate for the reward rather than the experience. They begin to evaluate every activity through a transactional lens.

How many points do I get for that? Is it worth my time? What do I receive if I finish?

The challenge becomes something to complete rather than something to enjoy.

The irony is that organizations are often trying to encourage behaviors that people can genuinely enjoy and sustain for years. Walking. Being active. Connecting with coworkers. Exploring new places. Learning new things. Yet the experience itself sometimes gets overshadowed by the transaction wrapped around it.

If a challenge requires increasingly larger rewards to attract participation, it’s worth asking a different question: Is the challenge compelling enough on its own?

The most successful wellness challenges don’t rely on rewards to create excitement. They create anticipation, connection, discovery, and progress. Employees participate because they enjoy the experience, and the challenge becomes the vehicle that delivers it.

Anticipation: Give People Something to Look Forward To

The highest compliment a wellness challenge can receive isn’t a high participation rate.

It’s when employees ask when it’s coming back.

That’s the difference between a program and a tradition.

People look forward to annual events because they remember how those events made them feel. They remember the conversations, the experiences, the accomplishments, and the sense of being part of something shared. The anticipation begins long before the event itself.

The same principle applies to wellness challenges.

A challenge that feels fresh, engaging, and memorable creates momentum that carries into the following year. Employees begin looking forward to the next experience. Teams start planning for it. Returning participants encourage others to join.

Of course, anticipation doesn’t happen automatically. Familiarity alone isn’t enough. If the experience never changes, even a popular challenge can become stale. The strongest programs evolve over time, introducing new content, new discoveries, and new reasons to participate while preserving the elements people already love.

That’s how a challenge becomes something employees expect, anticipate, and ultimately value.

Connection: Design for Belonging

Many workplace wellness challenges place competition at the center of the experience.

Leaderboards dominate the screen. Top performers receive recognition. The focus shifts toward identifying who did the most.

That approach creates excitement for some employees. It creates distance for many others.

The employee who wants to dominate the leaderboard usually doesn’t need much encouragement. They’re likely to participate regardless. The bigger opportunity lies with employees who are wondering whether they can keep up, whether they’ll fit in, and whether the experience is worth their time.

That’s where connection becomes so important.

People stay engaged when they feel supported. They stay engaged when coworkers encourage them. They stay engaged when their contribution matters, even if they’re not the most active person in the organization.

Shared goals, team milestones, and inclusive achievement thresholds create an environment where employees can succeed together. The conversation shifts from “Who’s winning?” to “How are we doing?”

The goal of a workplace wellness challenge shouldn’t be to identify the fittest employees.

It should be to create an experience where the greatest number of employees feel successful, engaged, and motivated to participate again.

A little friendly competition can add energy. A sense of belonging keeps people coming back.

Discovery: Give People Something More Interesting Than a Step Count

Let’s be honest: very few employees wake up excited about logging another 8,000 steps.

What they get excited about is what those steps represent. A shared experience. A destination. A story. A memory. A discovery.

People enjoy experiences that spark curiosity, nostalgia, learning, and conversation. That’s why challenges built around exploration, storytelling, music, travel, history, nature, or other meaningful themes generate a different kind of engagement than challenges focused exclusively on numbers.

When participants unlock a landmark, discover an interesting fact, revisit a favorite decade of music, or learn something unexpected, the challenge becomes bigger than the activity itself. The experience gives employees something to talk about, share, and anticipate.

The activity provides the movement. The experience provides the meaning.

This is one reason the strongest wellness challenges continue evolving. New attractions, new discoveries, fresh content, and unexpected moments keep the experience interesting. Participants aren’t simply repeating the same activity. They’re continuing a journey.

And journeys are far more engaging than checklists.

Progress: Help More People Feel Successful

Every successful challenge gives participants a sense of forward momentum.

Not just activity. Progress.

Progress reinforces effort. It creates confidence. It helps participants see that their efforts matter.

The most effective challenges make progress visible in multiple ways. Participants can see their own accomplishments. Teams can see their collective achievements. Milestones create moments of celebration throughout the experience rather than waiting until the very end.

Just as importantly, progress should feel attainable.

When success is reserved for the most active employees, many participants quietly decide they never had a realistic chance. When milestones reward consistency, participation, and improvement, far more employees experience success.

And success creates momentum.

People who feel successful are more likely to continue participating, more likely to return next time, and more likely to encourage others to join.

The Challenge Is the Vehicle

Organizations sometimes spend so much time thinking about incentives that they overlook a more important question: Would employees enjoy this even if there were no points attached to it?

That’s not an argument against incentives. Small prizes, giveaways, and recognition can help attract attention and create excitement. But incentives work best when they support a great experience rather than compensate for a weak one.

Employees don’t look forward to wellness challenges because they’re wellness challenges.

They look forward to what great wellness challenges make possible.

The anticipation of an experience they’re eager to revisit. The connections they build with coworkers. The discoveries they make along the way. The satisfaction of seeing progress and contributing to something meaningful.

When organizations design around anticipation, connection, discovery, and progress, participation becomes less about convincing employees to join and more about creating something they genuinely want to be part of.

Why Walktober™ and 10K-A-Day™ Become Annual Traditions

The most successful wellness challenges create more than participation. They create anticipation, connection, discovery, and progress. That’s exactly why organizations return to Walktober and 10K-A-Day year after year.

• Anticipation begins long before launch. For many organizations, Walktober has become an annual tradition that employees look forward to each fall. Returning participants know they’ll find fresh attractions, new discoveries, updated features, and new opportunities to connect with coworkers.
• Connection is built through team participation, shared goals, friendly encouragement, and a culture of support. Rather than focusing on a handful of top performers, both programs are designed to help employees of all activity levels experience success.
• Discovery is where both challenges shine. Participants unlock fascinating attractions, learn interesting facts, and explore destinations from around the world. The challenge becomes more than counting steps — it becomes an experience employees talk about and share.
• Progress remains visible throughout the journey. Personal milestones, team achievements, and attainable activity thresholds help participants see their success building day by day.

The result is a challenge employees don’t join simply because they should. They join because they enjoy the experience and look forward to being part of it again.

I really can’t express how much our company enjoyed participating in Walktober. Everyone is already talking about next year’s event.

Christina P.
Human Resource Manager
APT Management

Frequently Asked Questions

What makes a successful employee wellness challenge?

A successful wellness challenge gives employees an experience they genuinely want to be part of. The strongest challenges create anticipation, connection with coworkers, opportunities for discovery, and a visible sense of progress — rather than relying primarily on points, prizes, or incentives.

How can you increase participation in a workplace wellness challenge?

Make the experience engaging, inclusive, and attainable. Give employees something to look forward to, create opportunities to connect with coworkers, add interesting content or discoveries, and make progress visible so people at different activity levels can feel successful.

Do incentives increase wellness challenge participation?

Incentives can attract attention and encourage employees to participate, but they work best when they support an engaging experience rather than compensate for a weak one. Employees are more likely to return when they enjoy the challenge itself. 

How do you make a wellness challenge engaging for employees of different fitness levels?

Design the challenge so success isn’t limited to the most active employees. Shared goals, team milestones, attainable achievement levels, and recognition for consistency and improvement can help more employees feel successful and motivated to participate. 

How do you turn a wellness challenge into an annual tradition?

Create an experience employees remember and want to repeat, then keep it fresh. Preserve the elements participants enjoy while adding new content, discoveries, and experiences that give employees something new to anticipate each year.