Read time: ~12 minutes
We live in a world of abundance. Never in history has there been more leisure and “fun” activities to take part in. Never has there been more content to consume, people to meet, and group chats to fire memes into. The beauty of today is that all of this stimulation is accessible with the push of a touch screen or click of a mouse. The result of having all of these options at our fingertips is that prioritizing how to spend our time is now more difficult than actually finding things to do. While the abundance of choice is something I have written about before, I haven’t really shed light on how I go about making my own time allocation decisions. So that is what I want to do here.
Something that I am being reminded of more and more lately is the simple truth that life is shorter than we realize. This becomes all the more visceral when you actually do the math. While I’m certain there is no shortage of material detailing the right way to spend your time, nothing I have read has stuck with me long enough to actually change my behavior over the long haul. The framework that has helped me minimize regrets and reduce stress when planning my life has been prioritizing those experiences that I won’t get another chance at and fitting in everything else if I have time.
So how do you know which experiences you’ll get a second chance at and which are once-in-a-lifetime opportunities?
The short answer: you don’t, but you can make an educated guess.
I haven’t batted 1.000 and there are definitely events I regret missing and certainly events I went to that I regretted attending, but thinking about limited availability events in the following three categories has helped me make faster, better decisions on how I actually want to be spending my time.
Category 1: Those activities with expiration dates
The thesis of this category is the people you count close in your life and the activities you enjoy doing with them are going to change as you get older as a result of the growth and development we all undergo with age. You can try to hold on to your youth as much as you like but your hobbies, interests, and energy levels will change and you’ll be much happier if you accept that as a given fact and cherish the present (which is all you really have anyway).
A personal example of this is the fact that I am no longer spending large chunks of time on Saturdays watching football and drinking beer with my friends. On one hand that represents a positive change in routine for me. If that was how I was still passing valuable free time on Saturdays, I would feel unfulfilled and that’s the type of long-term regret that can be cancerous to overall satisfaction. On the other hand, part of me laments losing those days because they marked some of the most carefree and fun afternoons of my young adult life.
Because we are aging and changing along with those we love we are all faced with time horizons for experiences that we now enjoy. As my friends get married and have kids I’m certain that it will get even harder to schedule big group trips with my increasingly dispersed friend group. As my body slowly but surely degrades I probably won’t be able to keep dropping 20-foot cliffs on skis. Even my nights out on the town have shortened. When I was in New York I could dance my ass off until 4 am or later. I still do that every once in a while but the price I now pay for a late night out has increased significantly. Part of me wants to be sad because these eras are coming to an end but because they aren’t over yet, I’m jumping at every chance I get to schedule a trip with ten of my buddies. Or do a backflip on skis. Or even see a sunrise after a night out. I’m not done with this stuff yet but because I know their days are numbered, it’s extremely important that I prioritize these experiences now before they don’t interest me or I no longer have the energy level (or body) to enjoy them.
Once I made my peace with the fact that I won’t be living my life the same way for the rest of my days I started to think critically about which events, trips, activities, or even relationships may have a time horizon on them, and have started to prioritize those above others. The experiences that fall into this category can be loosely grouped in the below buckets:
Time with your loved ones (especially parents and siblings who you don’t live near anymore)
Large group trips with close friends (Schedules only get harder to coordinate the older you get and this will get exponentially harder when my friends start having kids. I’ve already seen the pattern with my friends with dogs and I imagine that trend will only be exacerbated once children are in the mix)
Physically demanding activities that you may lose the ability to experience in the same way as you age
Category 2: Truly “Once in a lifetime” Opportunities
The second category of experiences, activities, etc… that I try to prioritize is those with specific windows of availability. These are sometimes visible but it takes a certain level of seriousness within yourself to be honest and determine whether or not you’ll get another shot at a given experience.
Because I’m such a big live music fan, this is one that really hits home for me. When an artist I love releases an album I love (which doesn’t happen that often), and they go on tour, I always try to ensure that I catch them at least once if not more. The reason I put such an emphasis on this is that artists are people too, and like people, they change from project to project. If I like a group’s most recent album, I need to see them when they are touring it because if I wait until the next tour, they may have moved in an entirely new direction. Which could mean missing a chance to hear my favorite song or worse, the next time I see them they could play a set composed entirely of music I don’t like.
While it may seem that this is only relevant to live music, it actually extends to almost every other cultural area of modern life. If you’re a movie fan and a director you love releases a movie that is best seen on the big screen, you should make it an absolute priority to see it in a theater while it’s being shown. You don’t know if you’ll get another shot to experience it as the filmmaker intended. The same goes for restaurants. Even the high-end joints change management and chefs all the time. If you loved a meal once from a place you had better take every chance to get to eat there because you don’t know when they’ll change the menu and remove your favorite dish. This logic extends to museums, plays, comedy, etc... and reinforces the idea that transitory experiences need to be prioritized lest you miss your window.
Some experiences that fall into this category are listed below but obviously, there are many that I have left out for the sake of brevity.
Movies in theater from your favorite actors or directors
Concerts for an artist that released an album you love
Meals at your favorite restaurants
Comedy shows for your favorite comedians
Category 3: Your “Someday Shelf”
Many of us have a list of goals we would like to achieve, places we would like to visit, or hobbies we would like to pick up, but for whatever reason, we haven’t prioritized and oriented ourselves around checking those boxes. As I have mentioned in this post, life is short, and if you don’t ruthlessly prioritize you may miss your chance to do the verb to be the noun.
For the best take on this idea, I direct you to my friend Eric Wang’s Substack piece titled “An Old Song and Dance, Revisited”. In this piece he talks about a concept titled the “Someday Shelf.” The Someday Shelf refers to “a person's aspired-to hobbies, activities, things to do - all stuck in purgatory.” While the track he takes is bent more towards allocating free time during a lockdown, his thesis remains true even as normal life has resumed. We all have Someday Shelves that contain all of the goals we’d like to accomplish, the type of person we would like to become, and places we would like to visit. To turn these things from “Maybe someday” to “I’m glad I did that” requires honesty and effort from the guy in the glass.
For me, publishing my writing was always on my Someday Shelf. I had always thought about doing it but had never pushed myself to go from zero to one. Now that I have built a somewhat consistent habit I know that this is something that I’m going to be doing for years to come. But because I’ve sunk time and energy into this hobby, I have fully punted learning how to play the piano into a long stint in purgatory. I’m ok with that because this is what I want to be doing. But as someone who wanted to learn how to play an instrument, it was difficult to be honest and realize that I just don’t have the time or desire for that right now. Which is fine. There is a cliche that rings true in this instance: “People overestimate what they can accomplish in a year but underestimate what they can accomplish in ten”. Just because something isn’t a priority now doesn’t mean that you can’t do it later. But to accomplish anything you have to say no to a lot of other, less important, things. This brings me to how I would advise people to work their way through their Someday Shelf:
Be honest with yourself about any possible goals, destinations, hobbies, etc... and figure out what you really want to do with your life, and release yourself from the obligation to do anything else.
Ruthlessly prioritize those things that you are interested in now and run them through their natural lifespan at the cost of lower priority items.
We all have many potential versions of ourselves that we would love to see actualized if only we had enough time, but because time is limited you have to be honest with yourself about what you want to spend your time doing, and then be merciless about spending your time doing that thing for as long as it holds your attention. Then move on to the next thing. This framework, for me, has ensured that I live with minimal regrets and am spending my time in both a way that makes me happy and supplies me with a satisfying life.
You’ve told me what to do, so what shouldn’t I do?
I have spent most of this post talking about the items you should prioritize on your never-ending list of things to fill your free time with, but what about the other side? What are the things that you should definitely move down in priority because you will get another chance at them again? For me, it’s pretty simple. If you prioritize everything I listed above, it only makes sense to deprioritize all of the other stuff. Here are some items that come to mind but this will vary wildly depending on who you are and what you like to do:
Anything that you feel like you “should” do. Avoid the word “should” at all costs. Do what you want to do and be shameless about it. Life is too short to put yourself into anyone else’s box.
Social obligations that are not a “Hell yes”. There will be endless birthdays, parties, nights out at bars, etc… if you say yes to everything that isn’t a “Hell yes” you will drastically cut into the time you have to do the things you truly want to do. Of course, you will have obligations that you don’t choose for yourself but if you communicate well and show up when it’s important you’ll find that you can carve out more of your own time than you think.
Work given to you by others that aren’t Significant Others, or Close Family Members. Doing favors and chores for your parents, siblings, and significant others is a perfectly valuable way to spend your time but working through the night because your boss is a poor communicator is far less valuable. And there are plenty of examples of people asking you for your time but infrequently do their requests align with how you want to be spending your life, so you should cut out other people’s priorities as much as possible.
Putting it into practice
All of what I have laid out here is much easier said than done. Taking what looks relatively simple on the page and putting it into practice is where the majority of the work lies.
Additionally, you should be cautious about scheduling every moment of your life to optimize for maximum _____. While it may increase your productive output, it also may create an “over-optimization anxiety” wherein you feel that every minute must be spent in the most “optimal” manner. This mindset can be crippling to living in the present and enjoying yourself on a day-to-day basis. So while I’ve outlined a guide to follow here, the way I put it into practice is a bit more casual than you might think.
When I’m thinking about a week or a month’s schedule, I have an idea which items are from the three categories of things that should be prioritized, and check in with myself to ensure that I’ve dedicated enough time to that list. When I find myself spending more time on low-priority events than I would prefer, I re-evaluate my list and adjust my schedule accordingly. It’s quite simple but requires some self-awareness to know what you actually want to do, and communication/discipline to ensure you’re actually spending your time doing it.
It’s not a perfect system, but forcing myself to think about this has helped me think through what trips I want to go on, how I’m spending my weekends, and even how I think about my plan for the year and I’m hopeful that it will help you as well.
Yeeesh time to clean out my "Someday Shelf"
It seems like a core motivator to take a framework like this seriously is really internalizing how short life is. How do you do that?