In 1958, the legendary journalist Hunter S. Thompson wrote a powerful letter to a friend.1

This friend had reached out to the late writer to ask for life advice. This was before Thompson was famous. In fact, he was only 20-years old when he wrote the letter.

The whole thing can be found in Letters of Note, but there is a particular section in it that really captures a strange paradox that we all face at some point in life. Here’s Thompson:

“Whether to float with the tide, or to swim for a goal. It is a choice we must all make consciously or unconsciously at one time in our lives. So few people understand this! Think of any decision you’ve ever made which had a bearing on your future: I may be wrong, but I don’t see how it could have been anything but a choice however indirect— between the two things I’ve mentioned: the floating or the swimming.

But why not float if you have no goal? That is another question. It is unquestionably better to enjoy the floating than to swim in uncertainty. So how does a man find a goal? Not a castle in the stars, but a real and tangible thing. How can a man be sure he’s not after the “big rock candy mountain,” the enticing sugar-candy goal that has little taste and no substance?

The answer— and, in a sense, the tragedy of life— is that we seek to understand the goal and not the man. We set up a goal which demands of us certain things: and we do these things. We adjust to the demands of a concept which CANNOT be valid. When you were young, let us say that you wanted to be a fireman. I feel reasonably safe in saying that you no longer want to be a fireman. Why? Because your perspective has changed. It’s not the fireman who has changed, but you. Every man is the sum total of his reactions to experience. As your experiences differ and multiply, you become a different man, and hence your perspective changes. This goes on and on. Every reaction is a learning process; every significant experience alters your perspective.”2

The Danger of a Long-Term Goal

Over an extended period, most of us need some sense of meaning through pursuits of sorts. We may be comfortable floating for a while, but feeling in control and having a direction is a craving we all need to satisfy. Leaving life up to chance isn’t a good way to do that.

Beyond environmental factors, the future is determined by both the choices we make and the choices we don’t make. What you do today largely shapes how you live tomorrow.

Between today and tomorrow, however, is the journey. That’s where most of your time is spent, and how you navigate this journey is influenced by your defined sense of direction.

But this direction tends to take shape as a long-term goal, and herein lies our problem.

As Thompson points out, one of the only constants in life is change. We think and desire different things at 25 than we at 40 than we do at 55. There may be a minority of people who pick something and can pursue that over decades, but those are the exception, not the rule.

Defining a fragile long-term goal and molding yourself in its shape at all costs is no better than aimless floating. In fact, it’s worse, and there are real dangers that come with that.

The real purpose of life isn’t to force a purpose and let that guide you under all conditions, but it’s to continuously redefine what it means to be better tomorrow than you are today.

Instead of committing yourself to something that may or may not turn out to be a good choice, the focus should be on improving and defining yourself. The goal is secondary.

If within that definition, you sustain a long-term goal, so be it. If not, you define a new goal.

Seeking a Way of Life

A pre-defined goal may diverge away from our evolving perspective, but the same question remains. Within a quest to strive and to be better, how do we find meaningful pursuits?

The intuitive answer is to ask yourself what you want and then find a way to work that into your life. Unfortunately, that doesn’t do much. At any given time, there is a lot we want, and the question is ambiguous enough that it doesn’t really help us zone in on anything.

A better question to ask is, “Given my current situation, what way of life do I not want?”

As you think, you will find yourself with a list of things that you are not willing to tolerate, and that will direct you onto a more certain path towards the few things that are reasonable.

It’s easy to want to double your salary or to write that book you’ve always wanted, but it isn’t easy to decide that you are going to compromise the time you have with your family for more work or that all your evenings and weekends for the next year will be spent alone typing.

Once you accept the life you’re not willing to tolerate, you can take your pick out of the few possibilities left over and dedicate yourself to them as 6-month to 2-year long projects.

This way, if you enjoy the lifestyle and the commitment even as you change and grow, you can continue along that path. On the other hand, if you find that your optimal way of life is diverging away from that initial commitment, you can shift your dedication to something else.

Rather than molding yourself to a rigid goal, you mold the goal to an ideal way of life.

All You Need to Know

To float or to swim. Hunter S. Thompson understood this predicament better than most. He found himself somewhere in between, but ultimately, he knew that a choice was necessary.

“A man who procrastinates in his choosing will inevitably have his choice made for him by circumstance.”

Not many of us will disagree that we need something to pursue. We may drift aimlessly for a while here and there, but over time, we crave a sense of deliberate progress and control.

Conventional wisdom says that meaning comes from a singular long-term goal. We find a thing we either enjoy or are good at, and then we dedicate ourselves to that pursuit for life.

This may indeed be the case for a few among us, but it’s incomplete as a general and broad framework. We’re all a product of the sum of our experiences. Over time, these experiences change our perspective, and this perspective won’t always align with a pre-selected goal.

A better way to define the purpose of life is as a continuously evolving pursuit to be better in the future than you are now. Rather than molding yourself to a long-term goal, you instead seek out a way of life with shorter commitments that cater to how you grow over time.

You’re still responsible for choosing the direction you want to take, but the focus shifts from shaping yourself into an existing definition to continuously creating yourself along the way.

The difference between the two lies in flexibility and opportunity. The choice is yours.

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