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Ashley Clayton Kay
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The Ultimate Trick to Understanding What You Truly Want in Life

One of the most surprising and confusing parts of your 20s and early 30s is realizing that no one knows what they are doing. I believe a lot of this comes from adults asking young people what they want to do when they “grow up,” as if adolescents can realistically plan the next fifty years. When you get deeper into your twenties, you realize the adults were simply quizzing you with a test that no one can pass for the sake of small talk, which is not particularly helpful. As a young person, you begin feeling the need to have answers to look “grown up” and suddenly, you’re following whatever path you find yourself following for whatever reason you came up with for whatever person you wanted to answer to.

For most of our formative years, we believe that life is linear. We believe that we go to school, choose a career path, and have a family — or some version of this. For some people, this involves more extensive higher education; for others, it involves finding a place instead of a person to serve as family — a city, country, or group of people that make them feel at home. Some people climb ladders, others clean floors. We think we’ll do this, then that — each piece of our plans following each other end to end like a set of dominoes. And we really attach ourselves to the details creating these plans and identities — the college names, the occupational titles, the “family of four.”

In reality, we live in a world where life is like laundry on the floor in trails and piles of overlapping pockets and sleeves that we do not want to spend our free time sorting. We don’t want to sort it because we don’t know what we truly want in life.

How do we drop the old perception of our life skewed by societal expectations? How do we set goals and make choices without the weight of external influence? We are constantly encouraged to set goals or dream big or create a mission statement or pretend money is no object — all of which are too unrealistically vague.

Here’s what works:

Write your obituary.

Doesn’t matter if you’re 20 or 50 or 80. Write one. Write another one next year or five years from now. Keeping writing your obituary. Why? Because, let’s be honest, nothing quite brings life into focus like death. Nothing makes us more bold or more certain or more motivated than knowing that it will all be over someday. You can either try every day to get closer to your dream and die or not try every day to get closer to your dream and die. Either way, death is inevitable.

What I found when I wrote my obituary — (and I have done so at least three times) — is that my idea of what I want my life to look like, in the end, is quite (sometimes wildly) different than what I tell people.

In some of the obituaries I wrote, I went back to school, and in others, I did not; in some I have more than one kid, in others I did not. In some of the obituaries, I wrote one book or one series; in others, I wrote dozens. In some, Kretch and I ran a business together; in others, we both earned doctoral degrees. In some of the obituaries I wrote, we lived in a lot of different states or we sold all our stuff in retirement and roadtripped in an RV; in other obituaries, we lived in another country for many years.

When writing your obituary, do just one thing:

Write Without Limits.

Pretend you lived 100 years and your obituary is being written by Margalit Fox of the New York Times (love this Longform podcast with her). Give yourself plenty of words, no paring down. This is your fantasy obituary, make yourself a famously interesting person, make the people in your life famously interesting. Write with abandon but don’t include too many deus ex machinas (like, “then she won the lottery.”) The only part that has a limit is your past.

You will not accomplish all that you put into your obituary — that is not the point. The point is to discover:

What Stays the Same and What Changes.

The things that you keep the same are what you really want, what you truly value in life. That’s you — the real you. In the three versions I wrote for myself, I began to see a pattern: travel, writing, and family. That’s it. Before I die, all I really want to do is ride around with Kretch to different places, write books, and have some version of a family. Do I have lots of money? Minor detail. I know I want variety in my work. Where will we go? I don’t know, but I know we’ll go. I want to take in a lot from everywhere I go; I want to tell stories. Everything else — all the changes — becomes details. Jobs, schools, places, number of kids — things we are told are a big deal — are just the details of life.

But what about those often unpredictable “details” of life? What about those things that change? There’s only one thing you can do:

Embrace the Change.

That’s the wild part. That’s the part of your life that will always be a mystery until you’re there, thinking, So this is how the story goes…huh! We all make attempts to plan our trajectories, but in the end, the planning is part of the details, part of the change. By all means, plan away — we have to plan, we have to make decisions — but never be under the impression that plans are the part of life that stay the same in your story. You don’t have to plan for the parts of you that stay the same. Planning is just the way we handle the ever-changing details — the daily, weekly, and yearly choices. Soon enough, you will have to make another choice, another plan.

If you’re like me, you may find the things that stay the same — your true values — were set earlier in your life than you might think. Because, a lot of times, the things about you that stay the same — the core values that have sustained you since you were a kid — are still there, calling, and the older you get, the stronger those values become.

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