The Five Year Question

For the last few months, I’ve been taking a new approach to almost everything that I do. With every dollar that I spend, with every hour that I invest, I’m asking myself one simple question.

Will I be glad I spent this time or this money in this way five years from now?

I’m going to go at length into how I actually apply this question and some of the specific uses, but I want to start with what really matters.

How the Five Year Question Has Helped Me

In a nutshell, the five year question has resulted one big difference in my life that I can easily describe.

When I’m actually sticking tightly to using the five year question, my life begins to take on this feeling of positive momentum, a sense that I am building something better for myself and my family. It doesn’t happen immediately, but after several days of really adhering to that question, I begin to feel it in the pit of my stomach and I begin to see glimpses of it in my day to day life. My life is simply getting better. It’s a really optimistic and contented feeling and it’s one that I love having. (I’ll get more into this, and some of the tangible results, later on.)

On the other hand, when I don’t stick as tightly to that question and I let myself act much more in the moment, I begin to feel as though my life is cycling in place. While I might have more momentary “joy,” the truth is that a lot of that momentary joy is completely forgettable, and before very long, I begin to have a sense that there really isn’t any positive forward momentum going on, that my life is just staying in one place and isn’t getting any better at all.

This phenomenon is true in all different aspects of my life: financial, personal, physical, mental, and so on. When I’m regularly asking that one big question, things begin to feel better and they feel like they’re snowballing, and that feels good. When I’m not asking that question, things begin to feel like they’re just holding in place and I’m not getting any better.

In other words, the five year question is definitely a longer term thing. It’s not something that you switch on and find yourself instantly with an improved life. Instead, it’s more of a gradual sense of change, where you begin to just feel better about things and you slowly begin to notice results popping up here and there.

The longer you stick with it, though, the stronger the momentum becomes, the more optimistic and content and fulfilled you begin to feel, and the more tangible results start to pop up.

So, let’s dig in.

Using the Five Year Question in a Practical Way

There are three specific ways I’ve been applying this five year question to my own life. These three specific applications have a lot of cross-pollination and synergy between them, as I often see benefits from one bleeding into the other.

First, I ask myself this question each time I consider spending money. Will I be glad I spent this money in this way five years from now? Not only does this question inform me as to whether I should spend this money at all, it often helps me decide whether there are better options for my money use.

For example, let’s say I’m about to buy a Kindle book, so I’ll ask myself whether this is a purchase I’ll be happy with five years from now. Maybe I should just get this book from the library instead, and then if I discover it’s a great work that I’m going to want to reread multiple times in the future, then it might make sense to buy it. I am very happy, for example, that I own all of the books in a couple of my favorite fantasy series, but I wonder what I was ever thinking with some of the other novels on my shelf. There are a handful of personal development books that I’m glad that I own and can turn to whenever I want, but there are others that mystify me as to why I bought them. This question, on the cusp of a purchase, keeps me from buying books unless I’m pretty sure they’re going to be in the “glad to own them” category.

The consequences of that question? Right now, I have a small stack of books checked out from the library. I’m spending less money on books, too. Five years from now, because I asked this question a lot, I’m going to have a smaller personal library of books, but that library will be much more meaningful and valuable. I’ll also have more money.

Another example: let’s say I’m planning out meals for the week and writing a grocery list. I’ll literally ask myself whether I’ll be happy with this meal five years from now. For me to feel happy about it in the future, it’s either got to be something special or it’s got to be pretty healthy for my body and, ideally, inexpensive. This is steering me strongly toward either making low-cost healthy meals or making carefully prepared special meals or food items.

The consequences of this question? I’m consuming fewer calories and I’m losing weight (when we’re not traveling, something I’m still trying to figure out). I’m also spending less money on food. On the flip side, I’ve also had a few very memorable meals recently and I’ve got a lot of homemade food items in storage, things I enjoy making and consuming and sharing.

The next principle is that I ask myself this question when I’m assembling my to-do list for a given day. I go through that list and ask myself whether or not I’m really going to care about this task in five years and, if not, what can I change about it so that it does matter?

This has resulted in a few really positive changes. The biggest one is that I find that the items on my to-do list are much more meaningful and I feel more engaged to do them knowing that not only are they relevant now, but they’re also relevant long term. They still feel like tasks, but I now understand them as building blocks for a better life.

For example, I’ll look at a work task, such as brainstorming article ideas, and recognize that not only is it generating the ideas that I’ll write about in the next week or so, but it’s also likely to lead to trains of thought that will produce ideas for a long time, and some of the best ideas will likely become truly great articles that I’ll link back to and highlight over the years. I still link back to my best posts and post series from five years ago, even today, because I know they add value to people who read them. I feel more motivated to brainstorm because of that realization, that good ideas today mean richer and more valuable writing tomorrow, even as far as five years down the line.

I’ll look at other tasks, like checking email (which I do roughly once a day), and realize that the vast majority of it really won’t matter in five years, so I’ll intentionally cut down on the time I devote to email. In essence, I’ve changed the task to “quickly filter email for important things and delete the rest” because almost all of the email I get is only urgent, not important. It can be tossed away. I focus instead on the emails that might be important enough to care about five years from now – communications with loved ones, communications with the new site owners, and communication with readers with good questions, and I try to filter and find those as quickly as possible. Email has moved from “check everything” to “filter out important stuff super quickly and address only important stuff.”

I usually do this once a day as I build my to-do list. I consider each and every item through the lens of whether I’ll care about this task five years from now. If I won’t really care, is there a way to pivot it so that it will have a positive impact? If not, is there a way I can minimize the time and energy I spend on it so I have more time for things that I will care about in five years?

Part of what has helped with this is that I’ve thought deeply about what I will care about in five years. I’ll care about my family and the relationships I have with them. I’ll care about having created great content for The Simple Dollar and finding new ways to reach readers. I’ll care about my leisure time, but mostly in terms of bigger projects I completed – I’ll care about batches of home-brew that I made, but not time spent leafing through magazines, for example. Tasks that clearly further those things while also fulfilling today’s needs are ones that I highly prioritize – and the interesting part is that I want to do them. The simple act of having considered their long term impact makes those that have a positive long term impact more appealing to me. Knowing that doing this is going to make my life better down the road pushes me to work harder on it.

Finally, I reflect on that question at the start of each task. What am I doing here that I will be glad to have done five years from now? That simple question provides a great focus on the task at hand, one that’s really helped me to give my best at different tasks.

That question usually cuts in two different ways. If I realize that this is just something that needs to be done and isn’t going to really matter in five years (say, doing laundry), I do it as efficiently as I can. If I realize that treating this with seriousness will have good long term impact, but not treating it seriously will have little impact, I bring some real focus to the table (say, a taekwondo practice).

The Benefits

I spoke in general terms about the benefits above, particularly in terms of the general sense that I was making positive progress in my life and truly building it into something better when I was actively involved with asking questions.

However, I wanted to talk a bit more at length about what has changed for me specifically when I’ve adopted those questions, and what has happened when I’ve slacked off.

When I actively asked myself the money question, I spent a lot less. That question constantly pushed me to spend very little money on incidental stuff without some careful planning. Instead, I usually just found things I already had to achieve what I wanted to do, or I found free or super-cheap alternatives.

I found myself being more mindful about leisure time and working on more meaningful things. I found myself reading more challenging books and reading them more slowly. I gravitated back to taking notes, especially with nonfiction, and I’ve found that very satisfying. Most of my leisure time is spent with some bigger aim in mind – I’m getting better at something, for example, or I’m making something, or I’m adding to a list of things I want to complete.

I found myself more engaged with work. As I noted above, I started trying to approach work through the lens of five years, and when I started doing that, I started approaching things very differently. I began to recognize that some things I write are simply “in the moment” that capture some momentary essence, and others are meaningful resources that I’ll return to again and again, and I started to approach them differently. The “momentary” things are more from the heart and are written more quickly and honestly than before, while the “resources” are actually written more slowly and with more research. In other words, that question changed how I work in a significant way.

I’ve found myself de-emphasizing some things in my life. I really don’t put much time into things that won’t matter in two weeks. I do them, but I try to do them as efficiently and quickly as possible to get them out of the way. I try to blitz through household chores with an intensity I didn’t use to have because I now see that such momentary things aren’t big obstacles. They’re just things to be done and pushed aside efficiently so that I have room for better things.

I turn off my cell phone more and focus on the moment. I want to be mentally present when spending time with the people I care about or doing things that have long-term meaning in my life, and my cell phone takes me away from that. I’ve been turning it off a lot lately, and I’ve never regretted it. This is a change that’s stuck with me even when I slack off on the questions.

I feel more calm and optimistic overall. I don’t know what the specific key to this feeling is, but I suspect it’s just a lot of little factors combining together, all of which were triggered by constantly asking those questions.

So, why did I ever stop doing this?

The biggest reason is that it’s easy to stop thinking about the big picture when you’re stressed out and overburdened. When I feel this way, I fall into something of a “survival mode,” where I’m simply trying to keep juggling a lot of balls at once. I don’t apply the same critical thought to my decisions – instead, I just instinctively do things because if I don’t make decisions quickly, the available pool of options shrinks rapidly. I don’t really have a lot of time to think when I have one thing I need to do at 3:30, another thing in another town at 4:30, another thing in another town at 5:30, and have to collect kids for something else at 6:30, while squeezing in dinner somewhere in there for myself and some number of my children.

The reality is that these types of questions work best when you’ve done them so often that they become instinct, and if you haven’t done them enough and fall back into a “panic mode,” it’s like forgetting how to ride a bike just as you’re learning how to do so. I’ll find a lot of success asking those kinds of questions for a week or two, but it’s just not enough to really make it my default way of thinking. That kind of switch takes longer to establish. Then, if I’m interrupted by life’s chaos, I fall back and I fail to really establish the habit. I have to pick up the reins later.

What’s the solution? I haven’t really figured it out yet, aside from being diligent about picking up the reins when life’s challenges trick me or force me into dropping them.

Some Personal Finance Ramifications

Let’s specifically take a deeper look at what the “five year question” means in terms of your finances.

It means less impulse spending and wasteful, forgettable spending. Note that this is not less fun spending. This type of thinking doesn’t stop you from spending money on things that bring meaningful and lasting joy.

What it does do is that it stops you from spending money on things that are easily forgotten and have no real lasting impact on your life. It cuts out things like convenience store purchases or pointless little “treats” for yourself when you’re alone. Those types of things won’t matter in five days, let alone five years.

It also means more thoughtful purchases. If you apply this philosophy consistently, when you do make purchases, those purchases are going to be meaningful. You’ll be buying things that last. You’ll be buying consumables that provide a lasting benefit for your life – healthier foods, for starters. You’ll pay for experiences, but only when they really add value to your life. In other words, you’ll still spend, but that spending will have lasting purpose.

Those two things leads to less spending overall. That’s simply the reality of it. A lot of our “incidental” purchases are things that we scarcely remember, and if we’re diligent about applying the five year question, those purchases will simply go away. Sure, we might end up spending a little bit more on things that are fulfilling over the long term, but the net result, in my experience, is that there’s a notable net drop in spending.

If you’re spending less, applying the five year question to what’s left results in pretty smart financial choices. You’ll apply that money to things like early debt repayment, retirement savings, emergency funds, and other things that you’ll genuinely appreciate in five years. You’ll find it much easier than before to do the financially responsible thing, and you’ll find that the five year question provides further encouragement to do so.

Take It Home: Applying the Five Year Question in Your Own Life

How do you actually do this, though? Here are three very concrete ways that I apply this question in my own life, and how you can do it in your life.

First, I keep a daily to-do list and I apply this question to everything that I add to it. Will I care about this task in five years? If not, how can I change it so that I will care about it in five years? If I can’t change it, how can I make this task efficient and have little or no negative impact on my life five years down the road (meaning that I don’t just throw money at the problem)?

Make this part of your to-do list building routine. You’ll find that some of the tasks remain the same but become more meaningful, while other tasks change and either grow in efficiency or grow in meaning.

Second, build the habit of evaluating purchases this way by considering them both before and after purchasing. Try to establish the practice of asking yourself the five year question before you spend any money, but also do it after the purchase. Think about past purchases through the five year question when you’re idle, or spend some time going through past credit card statements with the five year question in mind.

The purpose of reflection isn’t to beat yourself up over past mistakes. The purpose is to open your eyes to the things you consider routine and reflect on whether or not they make sense. You’re trying to hone an instinct, in other words, so that in the future, your buying decisions are naturally filtered through the five year question without even consciously thinking about it. When that happens, you’re making better gut decisions when spending your hard-earned money, and it’s going to improve the whole of your life.

Finally, think often about the life you want in the future. This is a form of motivation to stick with asking the five year question regularly. Visualize the life you’ll have in five years if you continue to improve in the areas you want to improve. What is your life like if you get in better shape? What is your life like if you push through those classes? What is your life like if you start putting in more effort at work and eventually earn a promotion? What is your life like if you work on making your relationships deeper and more full of trust and love? Picture that life that you want. Picture it in detail. That’s your goal, and that’s what your reward will be if you simply stick with the five year question.

Final Thoughts

The five year question really is a sorter of priorities. It forces you to look at your day-to-day actions through the lens of the long term and the results are sometimes surprising, but they’re always useful. That perspective often puts you on a different path in life, one that might seem a little harder in the moment, but one that over time begins to reveal benefits in countless little ways, from a debt being paid off faster than expected to a friendly greeting in the park when you didn’t plan on it, from a bit more contentment about what you have to a better role at work.

Put the five year question to work in your life for a bit and see where it leads. I bet you’ll be happy with the results.

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