This week I finally took the time to sit down and make my Fun File, inspired by the book The Fun Habit by Dr. Mike Rucker, which I wrote about in my last post.

In case you missed that post or need a refresher, a Fun File is a list of fun activities you can reach for you when you’re scheduling your week and want to add more fun, or when you find yourself reaching for your phone when you’re tired or bored and don’t have the mental energy to come up with something better to do.

I’m definitely guilty of the latter, often not sure what to do with myself in the evenings after a long day of work – especially when it’s now getting dark out at 4:30! Lately I’ve felt increasingly annoyed with myself when I default to mindless screentime, so I figured making my Fun File would be a great exercise to get me out of this soul-sucking habit.

Admittedly, before I sat down to make my file, it was kind of one of those things on my to-do list that felt like it needed checking off (a.k.a., a chore), which is probably part of why it took me a while to get to it. Plus the last few weeks were extra busy with the Art Walk, an out-of-town retreat, a friend visiting, my birthday, then covid – mostly fun things! So it took me a little longer than I had originally planned (I’m giving myself grace though – because beating myself up about it would NOT be fun!).

But once I finally sat down to create my Fun File, it was actually really fun to make! I started with the things that I already regularly try to do – hike, paint, date nights with Brian, etc. I then started brainstorming other things I’d like to to do – things like getting better at Procreate, (a digital painting/drawing app), taking a Zumba class, volunteering, etc. My goal was to come up with as many things as I could, then whittle them down to the 8-15 ideas Mike suggests in his book.

I focused on activities that are practical for late fall and winter – so I left out things that obviously won’t be options this season – things like paddle boarding, wildflower hikes in the high country, outdoor concerts, and farmers’ markets.

I also aimed to include options at a variety of price points – lots of my ideas are free (like drawing or hiking), some cost as little as $5, and a few require more planning and financial investment. 

When I started to run out of ideas, I took to the internet. I literally googled “fun things to do” and landed on a thread with hundreds of ideas in the “Xennial” Subreddit. Xennial is the microgeneration I belong to, between Gen X and Millenial, so there were lots of suggestions relevant to my age group (bar-hopping is definitely behind most of us in our early-mid 40s!). People suggested gardening, playing the piano, board games, seeing a play, taking a cooking class, bowling, redecorating a room… the list was almost endless.

Then just for giggles, I decided to see what ChatGPT had to suggest as well. I prompted it with: “Please brainstorm at least 30 ideas for fun things to do for someone of the xennial generation who lives in a small mountain/rural town” (because a lot of “city” activities just aren’t available to me where I live in the Rockies).

It actually had some pretty fun and unique suggestions, like seasonal foraging (for berries or mushrooms), a stargazing picnic, and visiting a local farm. I thought these were great ideas, just not appropriate for colder months, so I asked it for more ideas for cold weather and/or evening activities after it’s dark.

Its refined list of ideas included: hot chocolate tasting, DIY candle-making, a murder mystery party, a trivia night, an indoor plant workshop, and many more. I particularly liked its suggestion of a full moon hike or snowshoe, so I added that one to my list.

Once I’d finished, my list was at 36 ideas. As I talked about in my last blog post, Mike says it’s important to reduce the list to 8-15 ideas to avoid the overwhelm of what he calls “overchoice”. Before I started crossing things off the list, I organized them in a spreadsheet by time commitment, indoor/outdoor, whether I can do them solo or they’re better enjoyed with other people, and how much planning/effort is required.

I’ve always been someone who has trouble eliminating things… I’m that person at the buffet who has to try everything. Yeah, FOMO! So instead of thinning out my list to just 8-15 ideas, I decided instead to move the ideas to new tabs: Weeknights, Weekdays, Weekends, and Specific Dates. That way when I’m choosing an activity, I can jump to the appropriate tab and easily pick something without struggling with the indecision caused by overchoice.

Of course, that’s not to say I can’t do a “weeknight” activity on a weekend, or that a “specific date” activity won’t fall on a weekday. So I’ll definitely need to be mindful when I choose to look at more than one tab, and don’t let myself get overwhelmed.

I’m feeling really optimistic about all the fun I’m going to have in the coming months… even though we’re at the beginning of the darkest season of the year. As someone who has suffered from seasonal depression on and off for many years, this makes me hopeful – and even excited for winter!

If you want inspiration for your own list (or you’re like me and just love a good spreadsheet), feel free to steal my winter Fun File and make it your own! You can grab it here (no need to sign up for anything or enter your email). Once you’re there, just go to File > “Make a copy” in Google docs.

Of course, this is just a jumping-off point and your activities might look completely different than mine – especially if you have little kids or are in a different season of life. Take what works for you, and leave the rest behind.

I’d love to hear what you’re adding to your Fun File… please share in the comments!