The Fun File and The Year of Fun

Nothing about building a Fun File and having your Year of Fun is that complex. A crawl, walk, run teaching strategy is simply a way to begin with basic ideas and progress to more robust concepts. Using the ideas and science below, simply crawl, walk, run to your most fun year yet by creating your own Fun File and scheduling it.

CRAWL: List of Fun

To support having more fun, I advocate creating a “Fun List.” After this initial exercise, you will always have an abundance of choice when you’re looking for opportunities to have fun. Creating your list is as straightforward as it sounds. Simply follow these steps:

  1. Determine the most reliable way for you to document and store your list (e.g., pen and paper, Word file, Google Docs, etc.).
  2. Brainstorm all the things from your past and present that bring you pleasure and enjoyment and store each item as a separate list item within your document.
  3. Do the best you can channeling your future-self and repeat the exercise, anticipating things that will bring your future-self pleasure and enjoyment (an example from my future-self is traveling to space).
  4. Maintain the list (over time) by adding and pruning activities as you see fit.

Some people find that they benefit from setting a time limit for this exercise, while others like to brainstorm over several days or weeks. Do whatever works best for you.

When we have a handcrafted list of available fun options, the list increases our awareness that we have more agency about how we spend our time than we might have initially thought. Our Fun List also provides us a sense of familiarity when it comes time to schedule more fun. When we have meaningful options for fun at our ready, we are often better positioned to take action (rather than deliberate; more on that later).

Once you have developed your comprehensive Fun List, it’s time to organize it into a Fun File. Fun Files fulfill two important psychological needs; our need for autonomy (i.e., choice) and our need for structure.

WALK: Fun File

Autonomy and Structure Make Good Bedfellows

The Fun FileThe need for autonomy and the need for structure are two independent human desires that often form a dynamic duo (De Jonge, Rietzschel, Van Yperen, 2018).  When we organize our free-formed Fun List into a Fun File, it provides us a compromise between our inherent needs for both autonomy and structure. It does this by preserving all our autonomous choices while simultaneously providing a sense of order.

The benefit? Creating order likely will generate more interesting ideas for fun. Research by Dr. Eric Rietzchel and colleagues suggest that some of us become more creative when we’re given structure because order relieves some of the cognitive load of having to pull ideas out of thin air. Once we see patterns of where we find fun, similar ideas will likely come easier (e.g., “I clearly like concerts, what are some bands I’m not thinking of that would be really fun to see?”). Furthermore, we can use this spared brain power for decision making and taking action. When we’re systematic and intentional, we are better focused on what’s important—actually having fun! Don’t believe me? Have you ever been really hungry, but choice got in the way of having a pleasurable meal?


Some will argue that methodically organizing our ideas/options into a Fun File creates a contradiction. That this proposed process of increasing our fun has the potential of being more a burden than a reward. I disagree, and here’s why: developing an organized list of options gives us both freedom of choice as well as providing a mechanism to guide choice. Science suggests that we increase the likelihood of a fun outcome when we are able to reduce the mental workload of having to always think of new options for fun. Dr. Rietzchel does warn that there is a fine line between structures that aid and structures that constrain too much. As such, the question we need to ask is, “What’s the right amount of structure for our Fun File?” The good news is not much, and there are only two elements I believe are essential:

  1. A sorting order of categories that is meaningful to you (e.g., activity type, difficulty to achieve, time of year, etc.).
  2. Your “shortlist.”

Make a Shortlist from Your Fun File

Now that you have a healthy list of ideas, sorted in a way that makes sense to you, we need to bubble some of your great ideas to the top to ensure that you enjoy them. Research completed by Cornell University and Microsoft Research shows that shortlists support better decision-making. The team studied computer users trying to choose a movie to watch. They found that the use of shortlists had several benefits, including (1) making better decisions, (2) offering more satisfaction, and (3) improving the quality of available choice (Schnabel, Bennett, Dumais, Joachims, 2016).

When we give ourselves too much choice, it can lead to inaction and, worse, anxiety. As the video above demonstrates, when the available options are abundant it is cognitively taxing—no fun. This is known as overchoice or choice overload. When given too many choices, we can often end up paralyzed and dissatisfied (Markus & Schwartz, 2010). It can be argued that constraint is essential for our well-being.

It appears that while we are attracted to abundance, too much of anything can be counterproductive. Overchoice makes it hard to prioritize, and in some cases, this leads us not to choose at all. Why is that? We need to consider that when presented with multiple ideas for fun, our brain needs to assess every option against the next one and predict which one will be the most enjoyable. If there are too many choices to evaluate, we get annoyed with the process. We don’t want that happening with our Fun File.

What’s the right number for our shortlist? Researchers from the California Institute of Technology in Pasadena asked participants to make a choice from sets of six, 12 or 24 items (participants were choosing pictures of landscapes they could use to decorate coffee mugs later). While the participants were making their decisions, their brain activity was being recorded with an MRI scan. The team led by Prof. Colin Camerer wanted to see if there was a difference in brain activity when presented with a different number of choices. They found that activity was higher for 12-item sets and lower for six-item and 24-item sets. Twelve was, therefore, identified as the optimal amount of options. In contrast, six and 24 were “too small” and “too large” (Reutskaja et al., 2018). The scientists concluded that the brain probably performs best when given between eight and 15 choices. Using this bit of brain science, we’ll make that the goal for our Fun File’s shortlist. Review your Fun File and pick your top eight to 15 choices. The only additional criterion is that items on this list should be in the realm of achievability (e.g., it would be fun for me to compete in another Ironman but that is no longer possible since my hip replacement).

RUN: The Year of Fun

I wish I could take credit for this one, but the Year of Fun is a result of my editor leveling up the power of the Fun File. She did this by taking her tailored list of fun ideas and scheduling them throughout the year (often committing to them through prepayment), thereby increasing the likelihood that her year is full of enjoyment. You can do the same thing.

She’s scheduled many of the activities with a friend to maximize the fun. Her ideas range in scope—from visiting a book sale, to attending concerts and sporting events. You can stack up your fun ideas any way you see fit; the secret sauce for this final phase is making sure they’re immutably scheduled.

EXTRA LAP (Bonus Science)

Science of Choice

The danger of having too many options was perhaps most famously demonstrated in an experiment by Profs. Sheena Iyengar and Mark Lepper (Iyengar & Lepper, 2000). To learn more about their study, check out Iyengar’s TED Talk below.


Choice Overload
Not all psychologists believe in choice overload. When Benjamin Scheibehenne, Reiner Greifeneder and Peter Todd (2010) conducted a review of 50 published and unpublished articles that looked at overchoice. They found that one of the biggest predictors of choice fatigue was not the number of options but the pre-existing preferences or expertise in the choice domain. It appears that people who have strong preferences are not as troubled if the number of choices increases compared to those with no prior preferences. Also, it seems that journals were more likely to publish studies that showed choice overload exists than those that did not find evidence for it, creating a false impression that choice overload is a fact. While I’m confident most of us will be better off starting with a shorter list of fun things to do, as your fun mastery increases and you become better aware of what works for you, feel free to add items to shortlist if you feel it doesn’t impede taking action towards more fun.

Sources & further reading:

De Jonge KMM, Rietzschel EF, Van Yperen NW. Stimulated by novelty? The role of psychological needs and perceived creativity. Pers Soc Psychol Bull. 2018;44(6):851.

Iyengar SS, Lepper MR. When choice is demotivating: Can one desire too much of a good thing? J Pers Soc Psychol. 2000;79(6): 995-1006

Markus HR, Schwartz B. Does Choice Mean Freedom and Well‐Being? J Consum Res. 2010; 37(2), 344-356.

Oga-Baldwin WLQ, Nakata Y. Structure also supports autonomy: Measuring and defining autonomy-supportive teaching in Japanese elementary foreign language classes. Jpn Psychol Res. 2015; 57(3): 167–179.

Reutskaja E, Lindner A, Nagel R et al. Choice overload reduces neural signatures of choice set value in dorsal striatum and anterior cingulate cortex. Nat Hum Behav 2018; 2: 925–935 doi:10.1038/s41562-018-0440-2

Rietzschel EF, Slijkhuis M, Van Yperen NW. Task structure, need for structure, and creativity. Eur J Soc Psychol 2014; 44(4): 386-399.

Scheibehenne B, Greifeneder R, Todd P. (2010). Can there ever be too many options? A meta-analytic review of choice overload. J Consum Res 2010; 37: 409-424.

Schnabel T, Bennett PN, Dumais ST, Joachims T. Using Shortlists to Support Decision Making and Improve Recommender System Performance. 25th International World Wide Web Conference, WWW 2016