How can you intelligently decide what to do with the rest of your life? And how can you find an answer that you won’t later change on a whim?

Many of us face this decision for the first time in our late teens and early 20s. Some never face it at all and shrink from the magnitude of it, allowing chance to decide. But this is a decision that can be made consciously — you just have to know how to approach it.

If you’re a typical reader of this site, then you have a number of long-term career possibilities. You could succeed at many different things if you put your mind to them. The problem isn’t that you don’t have a choice — it’s that you have too many choices. And because of the overload of choices, it’s difficult for you to commit to any of them. Perhaps you’ve made certain commitments in the past, only to change your mind a short way down the path.

The problem with outside-in

Most likely you were raised to make your career choices in an outside-in manner. Would you rather be a doctor, a lawyer, or an engineer? Do you want to get a job, go into the family business, or become self-employed? You scan the available options — even though they seem countless — and do your best to make a reasonable choice. Many people would consider this an intelligent approach.

The problem with the outside-in approach, however, is that it’s ultimately circular.

Suppose you want to make the best choice you can regarding what to do with your life. If you look outside yourself for the answer, you’ll see an overload of options — way too many for you to consider with any depth. You can’t make the best choice by scanning all the possibilities. You’ll die before you get close to finishing, and new career possibilities are being created all the time.

So instead of best, perhaps you’re willing to settle for a good choice. In order to know what a good choice is though, you need some kind of evaluation criteria. How do you define the “should” in “What should you do?” You need a context. For example, if you’re playing a game of chess and you want to know what move to make next, you need to know the rules of the game, the current board configuration, and ideally something about your opponent. If you don’t even know what game you’re playing, then you can’t intelligently answer the question, “What should you do?”

And that’s the basic problem — you don’t really know what game you’re playing here on earth. You don’t know the complete rules of the game. None of us do. Science and religion attempt to give us answers, but the most brilliant and respected people on both sides often disagree, and each side still has many unanswered questions. You can jump to conclusions like many people do, but the wisest approach may be to simply admit, “There are some things I just don’t know.”

You could take this a step further and say that if you don’t know the rules of the game, then your purpose should be to learn them. Figure out how the world works, and then your role may become more clear. This line of questioning leads many people into scientific and religious studies. And that’s fine. Humanity slowly pushes forward in these areas, but you as an individual still need to decide what piece of the puzzle to work on during your lifetime, and you’re still left swimming in a sea of choices. But at least this line of thinking gives you a goal — to learn why you exist and what you should do with your existence.

You’ve come full circle though. You conclude that what you should do with your life is to figure out what you should do with your life. Dead end.

You’re playing a game where you don’t know all the rules, and the exact purpose of the game isn’t clear. However, you still have to make a move. You have no choice in that respect. Even standing still is a valid move in the game of life. If you look to the game for answers, the ultimate answer will be that you should make moves that will help you figure out the game. But since you don’t know the game well enough, you still don’t know what move to make right now. This approach simply isn’t helpful. It just doesn’t create clarity. It will only leave you more confused.

Of course, you could just start making random moves to learn about life through trial and error. That’s a valid short-term approach, but we can do better than that…

The inside-out approach

The inside-out approach means that instead of looking to the game for guidance, look within yourself. Instead of asking, “What should I do?” or “What move should I make?” or “What career should I select?” just ask yourself, “What kind of player am I?”

Regardless of what game you’re playing, you bring a unique style to it. How would you describe that style? What is the style in which you would most like to play the game of life?

Are you aggressive, calculating, spontaneous, generous, compassionate, courageous, cautious, exploratory, etc?

We’re not really talking about values here. Values can shift around a lot. Sometimes your career may be more important than your social life, and other times your social life may come first. In this case we’re talking about deeply imbedded character traits. What kind of person are you at the core of your being?

How would you describe the “I” that is you? What do you love most?

I love to grow. It’s such an imbedded part of my psyche that I can’t not grow. Another attribute of my core self is courage. I have an almost inborn desire to want to run towards fear instead of away from it. And a third component is freedom. I love having tremendous personal freedom, especially when it comes to how I use my time.

The opposites of these attributes repel me. The opposite of growth would be stagnation or complacency (not decline because even in a state of decline, you can still learn something from it). The opposite of courage is cowardice. And the opposite of freedom is confinement. Someone who is my opposite would thus be drawn to lead a stagnant, cowardly, and confined existence.

Once you develop a sense of what kind of player you are, you can then play the game of life by injecting your own character into it. Whenever you don’t comprehend the rules of the game, supplement them with a part of yourself. So if it isn’t obvious what career you should pursue, look inward instead of outward for the answer. This will greatly narrow the field of possibilities and allow you to make a fairly intelligent choice. The better you come to know yourself, the more intelligently you can narrow that field. As your inward focus improves, your outer world will become more focused as well.

Being vs. doing

Suppose you list your core character attributes. How do you use those to make a long-term career choice?

First, let’s redefine the way you think about career. Just for a moment, forget about job titles, responsibilities, goals, projects, and tasks. Consider your career as an expression of who you are: being instead of doing.

If you’re an artist, your career is to create art. But what creates a masterpiece? Is it the brush strokes or the canvas? Is it the education of the artist? What creates a masterpiece is the artist. Really it’s the artist who’s the true masterpiece, and the artwork is the physical manifestation of the artist’s inner self. The Mona Lisa is Leonardo da Vinci.

Once you come at this problem from the mindset of beingness, instead of doingness, your real career becomes this: Your career is to express your inner self through the physical universe. That’s your job description.

Your true career is the dynamic expression of your inner being.

Instead of thinking of your career in such narrow terms as job titles, think of your career as an outward expression of your inner self.

If I gaze inward and see that I resonate with growth, courage, and freedom, then my career is actually to express these inner qualities out into the world. My job is essentially just to be myself.

Now as simplistic as this sounds, it’s actually very practical. How would you use this mindset to make real-life career decisions? You make your choices by asking, “Which is the best way to express my inner self?”

For example, when faced with a career-related choice, I can ask questions like, “Which choice will yield the most growth, require the most courage, and provide the most freedom?” These parts of my inner being shape my outward doing. I run a personal development business (growth). I work hard to increase web traffic (growth). I like to tackle controversial topics (courage). I do public speaking (courage). I work from home and set my own hours (freedom). I create mostly automated streams of income (freedom).

I love this approach because it creates clarity. The outside-in approach just doesn’t work for me. Should I be a writer, a speaker, an Internet entrepreneur? I can’t decide — all of them seem interesting. But when I turn inward, I see that all of these can be parts of my career because they all harmonize with my inner self. They’re all valid. I don’t need to choose just one of these narrow bands; in fact, the type of “player” I am dictates that I should include all of these things under the same umbrella.

To thine own self be true

Do you hesitate to make a long-term career commitment because you don’t want to limit yourself? I don’t want to limit myself either. By using an inside-out approach to career, you don’t have to limit yourself. You can express the whole you to the world, not just a small piece.

Do you find your current career too limiting? Do you enjoy your work while also wondering about all the other things you could be doing? Why not find a way to do them too? Stop thinking in terms of A or B, and think A and B. What would happen if you redefined your career as the outer expression of your inner being? What parts of your inner being are not enjoying enough outward expression? Are you incapacitating your intellect? Curtailing your creativity? Squelching your sense of humor?

Don’t turn your career into a prison for your soul. If your inner self wants to spread out, let it. To thine own self be true.