These Winter Wellness Challenges Worked Wonders for our Team - You’ve Got to Try Them too!

As winter rolls in, replacing autumn’s warmth with its own quiet, frosty beauty, it’s easy to feel the weight of the season settle in — like the long, foreboding winter in Game of Thrones. The low sun and snow-covered landscape cast shadows over our spirits, bringing a chill that people call as seasonal affective disorder.

Yet, as every true Northerner knows, “winter is coming” isn’t just a warning – it’s a call to prepare, adapt, and find strength. Instead of seeing winter as a time to go dormant, what if we, too, saw it as a chance to sharpen our resilience?

Last year, the Vantage Fit team embarked on a winter wellness journey that reframed these cold months as a time to build up our overall dimensions of wellness. In this blog, we’re sharing our favorite winter wellness challenges to help you not just endure winter but thrive in it.

After all, if we can find joy and purpose in the heart of winter, why shouldn’t you?

I've rounded up 24 Energizing Winter Wellness Challenges to Keep Your Team Motivated

Check them out:

Wellness Challenges for Emotional Wellness

1. Create a Hygge Haven

Inspired by the Danish philosophy of life, craft a Hygge Haven within your workplace.

A serene space where warmth and comfort take precedence over the everyday rush. Picture soft armchairs draped in blankets, dim lighting casting a golden glow, and the gentle scent of spiced tea or lavender in the air.

A corner adorned with books, puzzles, or journals that whispers, "Pause. Rest here". It’s about creating a moment where employees can unwind, reconnect with themselves, and let winter’s slower rhythm settle in.

Thoughtful, simple, and human—it’s the warmth of home, brought to work.

2. Nurture Emotional Resilience

This can be a little long as it is something that cannot be pushed to the back. This activity is regarding how, as employers, we can guide the employees toward establishing healthy emotional boundaries.

Below are certain measures that you can take:

Teach the art of Prioritizing "No"

Encourage your team to become more discerning with their time and energy. Empower them to politely yet firmly decline requests that don't align with their priorities or compromise their wellbeing.

Managers and leaders should model boundary-setting by saying “no” when necessary and explaining their reasoning. For example, declining non-essential meetings to prioritize deep work can show employees it’s acceptable to do the same.

Further, you can also host sessions that teach employees how to communicate assertively. Provide phrases they can use, such as:

• “I don’t have the capacity to take this on right now. Can we revisit it later?”
• “I want to give this project my full attention, but I’m currently focused on X. Can we adjust the timeline?”

Safeguard Personal Spaces

Work with your employees to establish boundaries around their personal time and digital spaces. Perhaps it's setting clear cut-off times for work emails and Slack messages or carving out device-free zones in their living areas.

Whatever the specifics, the goal is to create sanctuaries where they can truly recharge.

Help Cultivate Self-Awareness

The winter months have a way of magnifying our emotions, both positive and negative. This makes it an ideal time to reflect on our relationships, thought patterns, and triggers.

Provide resources that guide your team through the process of emotional self-evaluation. This could include identifying unhealthy attachments to recognizing when professional support may be warranted. By gaining this self-awareness, they'll be better equipped to make empowered choices.

Provide Professional Support

Another important step is to avoid hesitating to connect your employees with licensed therapists, counselors, or other mental health experts.

Whether it's offering subsidized therapy sessions or simply sharing trusted articles on emotional wellbeing, it demonstrates that you view mental healthcare as an integral part of overall wellness.

Your teams will appreciate the compassion and feel empowered to prioritize their emotional needs.

Let's ensure our employees aren't left to face the emotional challenges of the season alone.

3. Help Foster a Positive Mindset

Encourage employees to identify stress triggers by reflecting on work habits, personal routines, or environmental factors. Provide a simple worksheet or app to track and rank stressors.

Provide them with a Daily Reflection Template and Trigger Transformation Worksheet. Have a look:

By noting such things down, employees can become highly self-aware. This, in turn, would help them to keep their triggers and emotions in check.

Wellness Challenges for Physical Wellness

4. Arctic Explorer Challenge

How about you take employees on a virtual journey across the Arctic, where daily physical activities translate into miles on a digital map? In it, teams can progress through checkpoints, learning about different regions while accumulating activity minutes through various exercises.

This challenge stands out by combining education with physical activity. At each virtual location, you can share interesting facts about winter survival, local cultures, or wildlife.

Reward progress with themed prizes like outdoor adventure gear or winter sports equipment. And celebrate team milestones with special recognition events or additional time off.

5. Winter Warriors Fitness Bingo

Transform traditional fitness tracking into an engaging game of wellness bingo. This is where each square represents different winter wellness activities. From "20-minute indoor cardio" to "snowboarding", create diverse options that appeal to various fitness levels and interests.

Completing a bingo line earns immediate rewards while filling the entire card enters participants into a grand prize drawing. Make it more exciting by including "surprise" squares that reveal special challenges or instant prizes.

6. Lift Weights for a Cause

We all have probably heard so much when it comes to the importance of weight training. The internet is flooded with it. It's like retinol for your bones and muscles.

This winter, turn weight training into a force for good with a Dumbbells for Donations challenge. For every pound employees lift during their workouts, you can donate $0.10 to a local animal shelter (or a chosen cause). Employees can log their sessions through our Vantage Fit app, making it easy to track progress.

The Perks:

• Prizes: Reward top lifters with fitness gear, company swag, or gift cards. Include raffles for everyone who participates to keep it inclusive.

• Community Impact: Share updates on the donations made, showing how employees’ efforts directly benefit the cause.

Wellness Challenges for Occupational Wellness

7. Wellness Shuffle

Create a healthier work environment by engaging employees in a participatory wellness challenge. Each week focuses on a specific area: ergonomics, mental health, social connection, physical activity, etc.

You can encourage our employees to try small changes like:

• adjusting their desk setup for better posture,
• taking a 5-minute mindfulness break,
• organizing virtual coffee chats or
• adding short walks to their day.

They can track the impact of these changes and share their successes in a shared wellness library.

For example, if an employee finds that a five-minute afternoon stretch-break reduces neck strain, they can share their experience, inspiring others to try it too.

Employees earn points for implementing changes and bonus points if colleagues adopt their ideas.

8. The Skill Sprint

Help employees grow with a 30-day skill-building sprint. Each employee picks a skill they want to learn—like public speaking, mastering Excel, or improving project management. You can provide access to platforms like LinkedIn Learning/Masterclass and match them with a mentor who already knows the ropes.

Throughout the month, employees share their progress through quick video updates or blog posts on an internal platform. As they reach milestones, they earn points that go toward a professional development fund.

Everyone who completes the sprint earns a digital badge and can run mini-workshops to teach what they’ve learned. The employee who leads the most engaging session each month gets featured in the company newsletter and awarded wellness points.

9. Bob the ‘Balance’ Builder

Make work-life balance possible for employees with this challenge. Employees can track their working hours, breaks, and after-hours email habits using a wellness app. They earn points for healthy practices like taking proper lunch breaks, logging off at reasonable hours, and setting boundaries around work.

Weekly challenges might include "No-Email Saturdays" or "Daily Walk Breaks". Reward them by offering extra PTO days, meal delivery services, and home cleaning services.

The department that shows the most improved work-life balance gets a team celebration and the power to implement one company-wide work-life balance policy.

Wellness Challenges for Social Wellness

10. Holiday Cheer Screenings

What better way to lift the collective mood of the office than by indulging in the enduring magic of holiday movies? Gather your employees (virtually or in-person) for regular "Holiday Cheer Screenings" where everyone can laugh, cry, and sing along to timeless classics.

The shared experience of rediscovering favorite holiday moments is sure to foster connection and spread seasonal joy.

Here’s a list of holiday movies that your employees can watch and enjoy with kindred spirit as the year comes to an end.

11. Draw Your Colleague Challenge

Brighten up the season with a "Draw Your Colleagues Challenge," inspired by the viral "paint your partner" trend. Employees come together to sketch their coworkers in all their glory (or, let’s be honest, complete chaos).

Artistic talent isn’t just optional—it’s irrelevant.

Supply teams with crayons, markers, or digital drawing apps, and let the fun begin.

One person might end up with a Picasso-style nose, while another is barely recognizable as a stick figure. Share the masterpieces on an internal platform where everyone can vote for categories like “Most Creative”, “Funniest Attempt”, or “Looks Nothing Like Me, But Nice Try”.

Winners can get fun winter prizes like fuzzy socks, hot cocoa kits, or even framed prints of their questionable portraits.

It’s a lighthearted way to bring people together and laugh off the winter blues.

12. Cosplay

It's time for some winter cosplay!

You can encourage your employees to dress up as their favorite characters from movies, TV shows, books, or even their own creative ideas. Whether it’s a superhero, a fantasy character, or something completely unique, the goal is to have fun and get into the winter spirit.

Host the event virtually or in person. Employees can showcase their costumes and explain their choices in a brief, lighthearted presentation. Prizes can be awarded for categories like “Most Creative,” “Funniest,” or “Best DIY Costume”.

Get creative and unleash the holiday spirit in you!

Wellness Challenges for Spiritual Wellness

In the depth of winter, I finally learned that there was in me an invincible summer.
– Albert Camus

13. Letters to the Future Self

When was the last time anyone sat down with a pen and poured their thoughts onto paper? Letter writing feels like a lost art—the weight of a pen in one’s hand, the quiet focus, the honesty of putting your heart into words.

The Vantage Fit team brought this back as a part of its Spiritual Wellness Challenge.

Here's how you too can implement:

Set aside an hour for employees to write letters to their future selves. Provide elegant stationery and a peaceful space where they can pause, reflect, and connect with their inner thoughts. They might write about their hopes, intentions, or even a message of encouragement they’ll need in the spring.

Keep the letters safe and make the moment of opening them meaningful—perhaps with a small gathering over tea, coffee, and treats.

14. “Letting Go” Ritual

Sometimes, it helps to let things out so they don’t weigh us down.

Give employees a quiet moment to write down something they want to release—maybe stress, self-doubt, or a frustration they’ve been carrying.

Create a simple ritual to let those thoughts go. For in-person teams, it could be shredding the paper, dissolving it in water, or tossing it into a small, safe fire. For remote teams, they could type it out and hit delete.

It’s not about solving everything in one go—it’s about giving people a small, symbolic way to feel lighter and start fresh.

15. “What Brings You Joy” Wall

Set up a space—on a wall in the office or a shared digital board—where employees can share the little things that make them happy. It could be a favorite song, a snapshot of their pet, a photo from a recent trip, or even a funny meme they love.

Over time, this space becomes a collection of everything that makes people smile. It’s the kind of place where someone having a rough day can scroll or glance through and feel a little lighter.

Simple, honest, and a reminder that joy is often found in the smallest of things.

Wellness Challenges for Financial Wellness

16. Financial Goal Setting

Make financial goal-setting feel personal and approachable with this challenge.

• Host small, relaxed workshops where employees map out their money goals.
• Invite financial advisors to chat one-on-one and offer practical advice—not jargon.
• Sweeten the deal by rewarding employees who hit their quarterly goals with company contributions to their savings or retirement accounts.

Throw in thoughtful extras like budgeting apps or bestselling financial books for those who stay on top of their progress. It’s about giving them a clear path to feel more confident about their money.

17. New Year Pre-Financial Planning

How about starting the year on the right financial note? That sounds great, right?

Give employees a chance to sit down with certified planners and sketch out detailed budgets and savings plans. Highlight their wins by sharing their stories in the company newsletter (with permission, of course).

For an added twist, pair up employees who are savvy with money and those looking for guidance. Mentors can get recognition as well as a fun reward for sharing their knowledge.

18. Mindful Spending Month

Turn impulse buying into a game. For a month, you can ask employees to track the “almost buys” they skip and calculate how much they’ve saved. Create a shared space where they can post their savings stories, from avoiding that third latte to skipping a tempting flash sale.

Match their savings up to a set amount in their retirement accounts as a reward for staying mindful. At the end of the month, spotlight employees who made the biggest shifts with thoughtful prizes or recognition.

It’s not about shaming habits—it’s about celebrating small wins that add up.

And since holiday season is on the way, I think this is one of the most thoughtful challenges that you can offer. Our team has benefitted a lot from it.

Do not save what is left after spending; instead spend what is left after saving.
– Warren Buffett

Wellness Challenges for Intellectual Wellness

19. Weekly Brain Teasers Challenge

Brighten up winter mornings with a weekly brain teaser delivered every Monday. Make it fun by introducing themed weeks—like riddles, logic puzzles, or math challenges—and invite teams to solve them together over lunch or a coffee break.

Keep it lighthearted with titles like “Brain Teaser Champion” and small prizes like puzzle books or learning stipends. It’s a cozy way to keep minds sharp through the season.

20. Book Club for Curious Minds

A word after a word after a word is power.
– Margaret Atwood

This winter, kick off a book club that dives into fascinating non-fiction topics—anything from science to history. Give participants a book allowance or access to e-readers and host monthly discussions (virtual or in-person) over warm drinks.

Recognize book club MVPs with titles like “Reader of the Quarter” or a little extra time off for sharing summaries with their teams.

21. Podcast Discovery Journey

Create a winter-themed podcast library featuring interesting topics like creativity, innovation, or science. Pair up employees each week to discuss an episode over a virtual coffee or a quick walk outside.

Celebrate their insights with shoutouts in company newsletters and small rewards, like premium podcast subscriptions. It’s a low-pressure way to spark curiosity and good conversations during the season.

Wellness Challenge for Environmental Wellness

22. Plant a Hope

Give each employee a small plant or seed to care for, symbolizing a hope or goal they want to nurture. Over time, as the plant grows, it becomes a gentle reminder of progress and patience. For remote teams, offer to send seeds or suggest easy options they can find locally.

Reward thriving plants with fun prizes like gardening tools or unique seeds. Add some holiday cheer with a “Plant Parent of the Month” program—winners could receive sustainable gift baskets filled with winter goodies.

Plant seeds of happiness, hope, success, and love; it will all come back to you in abundance. This is the law of nature.
– Steve Maraboli, Life, the Truth, and Being Free (2012)

23. Zero-Waste Challenge

Give employees reusable mugs, water bottles, and lunch containers to cut down on disposable waste. Departments can compete to see who reduces waste the most, with monthly weigh-ins and prizes like eco-friendly office supplies or a breakroom upgrade.

Celebrate creative ideas—like upcycled decorations or zero-waste holiday gifts—with shoutouts in company emails. Recognize standout efforts with thoughtful, sustainable rewards.

24. Sustainable Commute Champions

Winter doesn’t have to stop green commuting. Encourage employees to walk, bike, or use public transit by offering rewards for sustainable travel. You can provide weather-ready perks like rainproof bike storage, winter cycling gear, or discounted transit passes.

Create a points system where every green commute counts toward rewards like wellness stipends or extra time off. Highlight a “Green Commuter Champion” each month, and for those in need of a ride, offer carpool matching with small fuel stipends for participants.

Conclusion

Wellness challenges go beyond just offering a program—they create an opportunity for your team to feel truly cared for and connected. It’s not about big gestures but the everyday moments that make a difference: a little laughter shared over a brain teaser, the calm of taking a quiet break, or the feeling of being acknowledged with a simple thank you.

These are the moments that help people feel like they’re more than just employees—they’re part of a community that values their well-being. By weaving these small, meaningful acts into the day-to-day, you’re building a culture where everyone can thrive.

Let’s make this winter one to remember—together.