One of the most fundamental questions I have considered in life is whether it is better to do the things you want to do or the things you’ll be glad you did. As with all questions, the answer is far from black and white. The question itself is inherently flawed. 

That is because the question implies that:

• It is possible to identify things with certainty as objectively better or worse

• The things you want to do and the things you’ll be glad you did are mutually exclusive

• You can always know the things you’ll be glad you did before you do them

None of these are necessarily true and so I recognize this question I have considered is an imperfect one with an imperfect answer. Still, it has led me to the creation of a useful framework for thinking about what to do whenever there is any doubt.

Let me begin by defining the two situations in which there is no doubt about what to do or not to do.

• When there is something that you want to do and you know or believe you will be glad you did later, you will generally do that thing without any hesitation.

• When there is something you do not want to do and you do not know or believe you will be glad you did later, you will generally not do that thing nor give it any further consideration.

The two situations described above represent opposite ends of the want to do / glad you did it spectrum in which both or neither of these primary reasons one would do something are satisfied. These situations are easy to navigate intuitively if not subconsciously so I will not waste another word on them herein.

The more interesting situations arise when the two reasons to do something (because you want to do it or will be glad you did) are either opposite or ambiguous. I would argue that there are 5 kinds of these situations in total. Those 5 kinds of situations are summarized as follows:

1. When you don’t want to do the thing but think you’ll be glad you did it. (i.e. exercise)

2. When you want to do the thing but think you’ll regret that you did it. (i.e. vices)

3. When you don’t know if you want to do the thing

4. When you don’t know if you’ll be glad you did the thing

5. When you don’t know if you want to do the thing or if you’ll be glad you did the thing

My proposition is that anything that one would consider doing should fall into one of these handful of buckets and that there are simple ways to approach these seemingly trickier situations once you identify which bucket they are in.

In the first instance, you should do the thing unless you really really don’t want to. Even then, sometimes you still should. You know you’ll be glad you did it.

In the second instance, you shouldn’t do the thing unless you really really want to. Even then, sometimes you still shouldn’t. You know you will regret it.

In next two instances which each involve one ambiguous aspect, decide based on the positivity or negativity of the other aspect (the unambiguous one).

The last instance may be the most common, especially for people who tend to dwell on the question of what to do. The strategic approach for what to do in this instance should come as a relief. In fact, it does not very much matter what you do in this double ambiguous instance. If you don’t know whether you want to do something or not and you don’t know whether you’ll be glad you did the thing or regret it, chances are you won’t be that glad or regretful either way, and if you don’t particularly want or not want to do it, then you don’t really care. It doesn’t really matter. The only wrong choice really is to dwell on this choice because you do not care about it and it does not matter. Just do it or don’t. 

All but the last of the five scenarios described above end up looking like 70/30 decisions. The last one seems more like a 51/49. With good judgment and a sound framework, all of them can be made into quick and easy decisions about what to do or not to do.

Identify the bucket. Apply the approach. Just do it, or don’t.