How a Proactive Bucket List Can Change Your Life

A few years ago, I wrote an article about “bucket lists” and shared my own. Rather than just reiterating my explanation of what a bucket list is and what my idea of a bucket list was at the time, I’ll just quote from the first part of that article:

A while back, I watched part of the Jack Nicholson/Morgan Freeman movie The Bucket List. In it (if you didn’t already know), the two main characters, older gentlemen, come up with a list of things they want to do before they “kick the bucket” – and proceed to do most of them, even though many of them really push their physical and mental limits.

It was a cute movie with a pretty thoughtful premise – the idea of the “bucket list” itself. Like a million other viewers of the movie, I was anxious to make my own “bucket list” – and so I did. Here it is, for all of you to read.

Spend more than a week in a rural part of France.
Spend more than a week in a rural part of Italy.
Drink a bottle of 1982 Latour, Pauillac wine with my wife and some friends.
Run for a significant political office.
Write the novel I have inside me – and get it published.
Visit Petra.
Run a marathon.
Do a three week gastronomic tour of America, a la Feasting on Asphalt.
Dance with my wife and with my daughter on a special evening.

Those were the nine I wrote down, anyway. Some may seem silly to you, but those are all things I want to do before I pass away.

That bucket list is fine and all, but when I look back on it now, I see one big problem with it. Most of the list revolves around spending money and doesn’t revolve around any kind of personal accomplishment. That bothers me, and here’s why.

First of all, many of the items would be quite expensive. The travel? Expensive. The bottle of wine? One of those bottles would cost thousands of dollars these days. That’s more than half the list right there.

Second of all, many of the items on the list don’t require anything of me other than opening up my wallet. Again, the travel. The bottle of wine. They don’t require anything of me.

Now, why is that a problem? I’ve come to learn that the things in life that really bring me joy are the things that I’ve actually invested some of myself into – building skills, building relationships, investing time and energy. Just spending money on something feels hollow.

That’s why, for example, I’ve come to realize that the best part of travel (for me, at least) is the people you do it with because it’s a shared experience based on your relationship with that person. Traveling alone is a much emptier experience, at least for me.

In all truth, only four items on that list really require anything of me:

Run for a significant political office.
Write the novel I have inside me – and get it published.
Run a marathon.
Dance with my wife and with my daughter on a special evening.

Even those have changed, too, for various reasons.

See, here’s the thing. I feel as though my bucket list should be authentically joyful, and I’ve learned that the most joyful moments in life are connected to the things you’ve achieved and built yourself. They’re built on top of lots of effort. They’re built on top of lots of time. They’re built on top of strong relationships. They’re built upon skills that I’ve had to teach myself along the way. They’re built on top of personal achievement, something I can be proud of.

When I reach that summit, I can not only be proud of the peak that I’ve reached, but also look back with fondness at the path that I took to get here. That’s the part that’s really missing from a one-off thing on a bucket list. I can’t look back with pride on the path to get here when drinking a $2,000 bottle of wine or sitting at a distant destination. I just threw a bunch of money at a problem, got a reward, and moved on with life.

Something that you just threw money at might be cool, but it’s not something that will last a lifetime. It’s not something that I will savor for years to come. It will be a nice moment – and then life will move on.

Building a Proactive Bucket List for Yourself

So, how can you build your own proactive bucket list? It’s pretty easy, actually.

First, think about things that you want to achieve that can’t be bought with money. What do you want to do with your life that doesn’t primarily involve tossing shovelfuls of money at that thing?

Generally, this resolves right back to personal achievements. When you eliminate money from the equation, you come back to spending the other resources that you have – time and energy. In what ways could you spend a lot of your time and energy on something that would be deeply meaningful for you?

Second, make sure they’re possible but very challenging. For example, if I wrote down “Play in a Major League Baseball game” on my proactive bucket list, I would fail. I’m never going to play in a Major League Baseball game unless I build the technology to switch bodies with Bryce Harper. Instead, I look for things that can actually happen if I focus on hard work. Do not choose things where you can be excluded based on natural skill level or you’re begging to be unable to ever complete that item.

Third, choose things where the journey is enjoyable, too, or at least teaches you new things along the way. If the journey to completing that bucket list item is purely painful and unenjoyable, you’re probably never going to complete it unless you have some truly exceptional fortitude. Instead, look for things where the journey will provide you with some degree of pleasure or, at the very least, the opportunity to try lots of new things.

If you can choose a handful of things that you’d love to achieve in your life that meet these criteria, you have a powerful proactive bucket list to work towards over the years of your life.

My New Proactive Bucket List

So, I’ve been rebuilding my bucket list a little bit. I’ve been focusing on things that build on personal accomplishment, that allow me to relish the things I’ve achieved rather than just spending money. I want achievements that are totally under my own control rather than relying on others, too.

This is my new proactive bucket list. This bucket list will never happen unless I get out of my chair and do something. To me, that’s what makes it useful and exciting.

I want to ride RAGBRAI. For those unaware, RAGBRAI refers to the Register’s Annual Great Bicycle Ride Across Iowa, which is an annual weeklong bicycle trip across Iowa that thousands of people do each year.

This is kind of a replacement for my marathon goal, as I’ve come to realize that my knees don’t handle running as well as they handle bicycling. Lately, I’ve come to find a lot of joy from bicycling around town and over to neighboring towns on the abundance of bicycle trails in this part of the state.

I would like to do it when my children are old enough to go with me in a few years, which will give me ample time to adequately train for it. In fact, I’ve already begun a slow training program where I’ve been substituting a bicycle ride for my daily walk on many days.

I want to complete and publish a novel. This is something I have been working on for a long time.

My problem isn’t the act of sitting down and writing fiction. My problem is consistently that I’ll get a certain percentage of the way into a novel, one that I already have plotted out and developed characters and relationships for, only to decide that the novel is garbage and abandon it. I lack confidence in my long-form fiction writing.

For me, the personal challenge is breaking through that wall of confidence.

I want to spend a few hundred hours volunteering for a political candidate I truly believe in. Really, this is all about wanting to be a part of a political campaign in an intimate way when it’s centered around a candidate that I truly want to see elected. I got a strong taste of this in 2012 when I worked for a Congressional campaign here in Iowa, but even then I didn’t really take a full dive into things.

I want to truly believe in a candidate and then clear the decks of all of my work for a few months before Election Day and do nothing else but help that candidate get elected.

I want to play a guitar or banjo accompaniment to singers in a public performance without making a fool of myself. I am not a trained musician in any way. I can play a few very simple songs on the piano and one or two extremely simple songs on the guitar and that’s about all.

I want more, and the only way to get there is through effort.

My goal is simply to play in public in a situation where I won’t feel like a fool in doing so, and to play with friends and family when I do so. Again, this is all about personal effort. I could do all of it right now if it weren’t for the “feel like a fool” part – and to cross that threshold is going to take a lot of practice.

It’s going to take some lessons. It will probably take some seriously sore fingers, too. Still, it’s something I can reach for.

I want to walk the trails of every state park in Iowa. Here’s a list of 61 state parks in Iowa. I want to visit each one and explore the trails on offer at each and every one of them.

I would also like to someday visit every national park and walk at least one trail in each one, but that starts to get perilously close to a “money” goal. On the other hand, I can reach every state park in Iowa on a day trip and many of them are along the way to other destinations, so there isn’t much cost involved for me in achieving this item on my bucket list.

Adding the “walk the trails” part of the equation requires me to do more than just drive through the park. I have to stop, identify some trails, and explore them in each park. For me, two trails per park will be sufficient.

I want to make a homemade beer based on a recipe entirely of my own devising that’s among the best I’ve ever tasted. Homebrewing is one of my biggest hobbies. I have all of the equipment I need to homebrew (the only thing I’d like to have is some more self-capping bottles and maybe a bigger brew pot), so this isn’t about money. It’s about learning how to do it in a way that produces a delicious product.

Every time I brew a batch, I learn something new. I learn how to control the temperature better. I learn why a secondary fermenter makes sense. The list goes on and on.

And, over time, I’m making better and better beers. I’ve actually made a beer that I consider to be almost in that “best of all time” tier, but it was based on a public recipe. My average brew is good, but not quite great yet and definitely not “best of all time” tier, but it’s improving.

Eventually, I’ll acquire enough skills to come up with something on my own, make it on my own, and be blown away by it. That’s the moment I’m looking for.

Of course, when I achieve it, I will probably try to do it again!

I want to design and publish a board game. Over the last few years, I’ve designed two different board games. One was really simple – it’s actually an interesting simple modification of rock-paper-scissors – while the other is substantially more complex.

Neither one of the games got beyond the drawings-on-index-cards-and-pieces-of-cardboard stage. That’s because doing so takes a lot of work, not just in terms of graphic design and assembling physical prototypes, but also in testing it and writing directions and playing it over and over and over and also organizing others to playtest it. It’s a long list of things to do.

I want to carry that process through to the finish with one or both of these games – or maybe a new design.

I want to write and complete an iOS app that is useful to someone besides myself. I enjoy writing computer programs. At my previous job, I had a lot of direction regarding writing things that were useful to other people. Today, my involvement mostly boils down to some very periphery contributions to a few open source projects.

I’ve written a few iOS apps just to learn how to do it, but they were very simple things. Only one was genuinely useful and that was definitely just a personal use.

So, what I’ve been doing is watching a lot of different message boards and forums for people who sometimes come up with ideas for iOS apps they’d like to see. Often they’re way too complicated and sometimes they’re already done by someone else, but every once in a while there’s an interesting and achievable idea.

That’s what I want to do. Write that app that’s useful to someone else.

I want to build an interesting YouTube channel with at least 200 videos out there. For me, this is definitely one of those “journey is way more important than the destination” kind of things. I want to learn about videography, scripting, editing, microphone placement, lighting, and all of those things along the way. This just gives me something of a central project to achieve.

Again, it’s all about an investment of time and energy more than anything else.

A final thought: When I listed all of the things here to my wife, she said it sounds like some sort of modern “most interesting man in the world” kind of thing. I think that’s kind of the point. These things are interesting because there’s personal achievement behind them.

The Next Step – for Me and for You

So, what’s the next step? Pull an item or two off of your bucket list and make them happen. Make that singular item – or those two items – your major goal in life over the next few years.

Once you’ve picked out an item or two, come up with a plan to achieve it. What can you do today to make progress on that bucket list item? What can you pull off by the end of the week? Answer those questions and add those items to your to-do list.

Then, review your progress at least once a week. Did you take care of those things? Did you do something that moves you a little closer to your big goal? What are you going to do next week to keep moving closer to that goal?

It’s a simple process that works for virtually any goal out there. Focus on what you can do in the short term to make that goal happen and then keep reviewing things to make sure you’re still on track.

Final Thoughts

So, what’s really the big picture here?

The truth is that the life achievements that really matter and bring lasting pride and joy are the ones that are built on top of your efforts. The things I am most proud of in my life weren’t bought. They were built by a lot of effort. Among them are my relationship with my wife, my relationship with my children, and The Simple Dollar.

To me, a “proactive bucket list” is about building things like that. It’s about creating things that were made by me and will build into something incredible if I carry it through to completion. Those things have value to me, not just in the completion, but in the experience of getting there.

They are milestones in a joyful life.

I wouldn’t expect your “proactive bucket list” to be anything like mine. You might want to refurbish an old car or write a book of poetry or read the great novels of the 20th century or start a food pantry.

In the end, though, they’re going to be similar where it matters. They’re going to involve things that we pour our hearts and our minds and our bodies into. They’re going to build upon themselves into an achievement we can be proud of and look back upon with joy and personal pride.

That, to me, is what a proactive bucket list is really all about. It makes your life better without throwing money at the problem.