30 Fun Things to Do Over the Holidays

30 Fun Things to Do Over the Holidays

Following my last post about why I’m adding fun to my to-do list, I received so many notes from you sharing that you too struggle at times to be in the moment and truly have fun.  It was nice to know that I’m not alone but also made me feel sad that this is the case.

Why aren’t we having more fun?

A few weekends ago, I went on a short holiday to Montreal with my Mom, sister and our two babies. While out for dinner in Old Montreal at a lively Italian restaurant, an ambulance raced up to the front of the building and parked right outside. As we were seated right next to the window, we had a front row seat. We didn’t think too much of it and went on chatting and eating when we saw a stretcher go right past again in the opposite direction.  The man on the stretcher had already been intubated and the paramedics were frantically administering CPR as they moved him into the vehicle. 

In that moment, I had a strange thought. I thought, that man might die tonight. He might actually already be dead.  I felt sad thinking of the family or friends that he was likely having dinner with that night at the restaurant next door. I thought of the family and friends who weren’t with him and who might be receiving some terrible news in the coming hours. And as much as I wanted to think, he will be fine, I also felt very viscerally in that moment that all around the world, while we are eating dinner and drinking wine, people are dying. Just as there are babies being born, there are people leaving this world.  That is just a fact.

We worry about what people think of us, we argue over silly things, we focus on all the ways we are different and separate from each other, when any one of us could easily be the man on the stretcher taking his last breaths. 

And that is why having fun now and often is so important. It isn’t selfish or frivolous or silly.  Having fun is life. It is as much life as struggling, it’s just that it feels easier to lean into struggling sometimes. We get to be here and we get to have fun. So let’s have it. Right?

But, as I wrote about in my last post, there is a difference between having fun and doing fun things. And sometimes, just doing something that is deemed as fun doesn’t mean we are actually feeling the lighthearted pleasure and joy that truly describes fun.

So to help solve this for myself, I put together a list of things that I know bring me pleasure and joy. And when I do the things on this list with the intention of making life a little sweeter, a little more enjoyable and pleasurable, that is what I experience. 

Here are 30 fun things to do (instead of checking your phone - since for many of us, that is what we’re doing instead!)

1. Give someone you don't know a generous compliment (You have the most beautiful hair. You have an awesome voice. Or my favourite, I love your eyebrows.)

2. Put on lovely background music as a soundtrack to your regular life at work and at home

3. Build momentum around the things you love to do (do a little every day - this is how I often write an entire post - just a few minutes every day)

4. Eat in beautiful restaurants even if it's just for a cocktail or dessert 

5. Re-read a book you loved as a kid

6. Wake up an hour before everyone else and enjoy the silence

7. Text a friend you haven’t seen in a while and book an impromptu coffee date


8. Book an Untouchable Day or even a few untouchable hours (Neil Pasricha talks about this in his new book - the idea is to go offline and give yourself time to think/work/reflect without any interruption)

9. Write a short speech about something you love to talk about

 Cold email someone completely random that you admire (no need to ask them for anything!)


11. Do a guided meditation - here is one of my favourites

12. Read a passage from an old book really slowly and carefully and dwell on the words and meaning

13. Never hesitate to buy/borrow a book that calls to you

14. Bake something from a recipe in a cookbook (not online!)

15. Make a ritual out of getting dressed and undressed (who didn’t feel comforted by the routine of Mr Rogers changing into his sweater and indoor shoes?)

16. Go for a long, aimless walk (leave your phone at home)

17. Water your plants, dust their leaves and take a moment to appreciate them

18. Walk around the room you’re in and clear the clutter (for me, clearing clutter is fun - it is like clearing space in my brain)

19. Do a puzzle (if you haven’t done one in a while, it is strangely satisfying??)

20. Put on music that makes you move and dance!

21. Make a top ten song, book and movie list and share it with all your friends as a gift (we all need recos all the time. Too much choice!)

22. Go to bed early. Light a candle, bring a hot tea and make yourself a cozy nest with a stack of books or magazines

23. Send a dear friend a quick text to let them know you love them and are thinking of them

24. Sit on the floor and go through a stack of old records (yours or your parents/grandparents)

25. Lie on the floor on your back for fifteen minutes and stare at the ceiling (I find the change of perspective makes me feel like a kid again)

26. Bake cookies even if you just eat one and give the rest away (like doing a puzzle, its strangely satisfying?)

27. Keep your favourite non-news sites bookmarked and read an article or two for inspiration

28. If you work in an office, change your scenery from time to time. Work out of a coffee shop, or a shared work space for an afternoon or a day

29. Immerse yourself fully into an activity outside of your every day - an escape room, axe throwing, horseback riding, an art exhibit? 

30. Send a note to someone either via email or even through the mail telling them how much you mean to them. Explain how they’ve inspired you or guided you. Write from your heart. It is fun to make others feel good too.

​Your list might be very different than mine and if so, I hope you make your own (and share them with me :))

The holidays are here. If anything, this is the time of year where we feel the most pressured to have fun, yet often, we let the stresses of the season take over and while we are doing fun things, we are very likely not having that much fun. In addition to taking a week long digital detox, I plan to focus on feeling fun in my bones this holiday. Will you join me?