How To Find Your Path — 4 Questions You Should Obsess Over

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Excerpt: Questions that matter shouldn’t be asked once—they should be obsessed over. Obsess over these four questions and learn how to find your path.

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“To get results, you can’t just ask the question once, you have to become obsessed with finding its greatest answer(s).”

Tony Robbins, Money: Master the Game

What better question to become obsessed with finding great answers to than the question of how we might spend our lives? The work we choose for ourselves will consume a significant chunk of our lives so we might as well spend some time up front figuring out how to spend it, eh?

If you only ever ask yourself once, “What path do I want to follow in life?” and accept an answer you gave at only one particular point in time (after graduating high school when you were 18?), then you certainly aren’t going to get the greatest answer you are capable of getting.

Questions that matter shouldn’t be asked once, as Tony points out above, they should be asked an obsessive amount of times. We should always be digging away at better and better answers that are buried deep within our complicated and ever evolving brains. Because life certainly isn’t linear and our paths in life certainly aren’t cookie cutter.

We change physically, mentally, and emotionally every single day (especially every single day after high school) and so do our worlds. Play that out over the course of months, years, and decades? You can see how a single decision that you made at one particular point in time might lead you down a less than ideal path later on.

Spend some time on the following questions and, if you dare, teach yourself how to become obsessed with finding their answers—you might very well find yourself coming up with great, path-altering answers.

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The 4 Questions You Should Obsess Over:

1) What feels like fun to me, but like work to others?

The mark of whether you are made for a task is not whether you love it but whether you can handle the pain of the task easier than most people—it is work after all.

Left to our own devices, we would instinctually choose to do what’s comfortable and avoid work all together. But that’s not an option (at least not for the vast majority of us). By working, we are able to provide for ourselves and our loved ones—without that work we wouldn’t be able to continue to live. And if we work hard enough (or smart enough), we might even be able to leverage ourselves into a position that allows us to provide and grow and contribute.

Growth and contribution are two elements that we should all have incorporated into our lives because that’s where the feelings of long-lasting meaning and fulfillment come from. If you can find work that aligns with your innate abilities, talents, aptitudes—that you can tolerate doing more than others—then you know you’re heading in the right direction.

And if you’re able to grow and/or contribute on that path too? Then you know that direction is worth pursuing. If you’re still unsure, think back to situations when you can remember enjoying yourself while other people were complaining? Remember, the work that pains you less than others is work worth investigating.

2) What makes me lose track of time?

Flow is the mental state you enter when you are so focused on the task at hand that the rest of the world fades away. This blend of happiness and peak performance is what athletes and performers experience when they are “in the zone.” It is nearly impossible to experience a flow state and not find the task satisfying at least to some degree.

If you find yourself checking the clock every few minutes while working, then you might consider that a sign that you’re heading in the wrong direction (or that you need to hustle your way out of that position to a higher level position that is more captivating). If you find yourself looking at the clock and realizing a lot more time has passed than you expected, then you might think about that as a sign as well.

It’s easy to lose track of time when you’re playing video games, binging on TV series, and scrolling through social media—that’s not what we’re talking about. Again, as discussed above, we’re talking about work here—not just any old ways of passing time.

Think about creative endeavors that make time fly by—drawing, painting, photography, video editing, graphic design, performance arts, music production, interior design, etc. Think about more structured endeavors that make time pass quickly—cleaning, organizing, scientific endeavors, mathematical endeavors, building/ engineering, software/ computer development, breaking things and putting them back together, etc.

This might hint you towards a field that scales your hobby to something larger with greater returns down the line.

3) Where do I get greater returns than the average person?

Taller people are, for the most part, going to get greater returns playing basketball than the average person. Charismatic people are, for the most part, going to get greater returns when working with people than the average person.  Intelligent people are, for the most part, going to get greater returns working in the field that aligns with their intelligence than the average person.

And the same is true for people who are physically strong when working with people who want to get strong; people who are mentally strong when working with people who also want to get mentally strong; and people who are emotionally strong when helping others through emotionally hard times.

We all have areas of strength that give us an edge over the average person—it might just need some cultivation and proper attention. Given a task that was assigned to you and a group of other people, where do you see yourself getting greater returns/ doing better than the rest?

If you were told to do work in a large group, what type of work would you hope was assigned? What might the tasks or situation look like? How can you position yourself into that type of situation more often so that you can cultivate and nurture that natural draw?

4) What comes naturally to me? 

For just a moment, ignore what you have been taught. Ignore what society has told you. Ignore what others expect of you. Look inside yourself and ask, “What feels natural to me? When have I felt alive? When have I felt like the real me?”

No internal judgements or people-pleasing. No defaulting to what mommy and daddy has told you to do. No second-guessing or self-criticism. No outside pressure to be a certain way, act a certain way, or produce a certain way.

If you could earn the same pay no matter what job you did, what would you pursue? Or, put another way: Imagine that money were no object, but all of your necessities for living were covered—beyond just seeking comfort, how might you spend your time in a productive way? What work would you choose to do—not because you had to, but because it came naturally to you?

Would you work with kids and share with them lessons of the world? Would you work with the less fortunate and help them get better off? Would you work with your peers and try to build something that might leave the world (or at least your world) a better place? Would you spend your time with the elderly and exchange with them insights that would deepen appreciation for life?

What can you imagine yourself doing that would leave you with feelings of engagement and enjoyment? Whenever you feel authentic and genuine, take note, because you are headed in the right direction.

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