How to Plan & Fix Your Broken Life

It's the start of a new year, and it's time to think about who you are and if you're doing it right.

This is a piece about how to plan out your life. But before I get into the planning process, here’s some context.

I like to plan. My mother likes to wander.

When she was 17, she took out her 1971 Vision Board and wrote, “Travel The World!,” and then she graduated high school a semester early and moved from New York to Miami to become a waitress. And then to Hawaii, to make puka shell necklaces. And then to Japan, to fall in love. She says it’s all okay. All aligned with her vision board.

A few years ago, she didn’t like the guy I was dating.

“He’s not Jewish and he didn't finish college,” she said.

“But mom,” I said, “if I like him, does any of that matter?”

In response, she took out a sharpie, and on her 2019 Vision Board wrote “Alexander will date an educated Jewish boy.”

A few months later, he and I broke up.

Now, I don’t like to give her vision board any credit. I refuse to believe that her art project of witchcrafting and manifesting with markers and phrases does anything at all. But I can tell you that she believes that it does. And that she’s not alone.

For those of you that don’t know what vision boards look like, here’s what Google Images will reveal:

Complete trash.

Regardless, over the past twenty years, vision boarding has become a fad, mostly thanks to influencers and celebrities who, after they’ve found fame and fortune, take it upon themselves to tell the rest of us how to live. 

A YouTube search for “Oprah”+vision+boarding will return 7,500 videos to watch, and on Amazon there are 20,000 vision boarding tools to buy. Content and products for the naively hopeful who, instead of making an actual plan for how to change their lives, believe that they can write down what they want for themselves and that it’ll all somehow just come true. Gullible optimists like my mother, who might as well wish upon stars.

In 2011, I sat with her in the kitchen.

“Well, he is my ideal husband,” she said while gluing a photo of Dustin Hoffman to her 2011 Vision Board.

“Look,” I said, “you can’t actually think that any of this really fixes your dating life…” 

“I actually do believe that,” she said. “Also, don’t worry about me,” she paused, “you’re the one who needs fixing.”

Fixing. I’m not broken. At least, not to me. I like my life and the way that it has unfolded. Every six months I make three different versions of a five-year plan. Then, I pick one of those versions and try my best to live it out.

The versions themselves contain at least one large alteration that occurs within each version’s first twelve months, along with the goals and actions that make up that version. The only actions I write down are the ones that are within my control (see image below).

For example, in Version A, during the first year, I’d keep my current job and would focus solely on writing, but in Version B, I’d make writing less a priority, and start a psychedelics company. In Version C, instead of psychedelics, I’d center my life around crypto.

Then, I map out the successive four years of each of those three versions, pick which life I like the most, and follow that path for the next six months.

I stole much of this from a book called “Designing Your Life”. But I had to change it — it was too lenient and forgiving. I needed something more aligned with my neurosis.

I’ve gotten feedback from friends that the way I live is “too controlling” and that I should just let life take me where it needs to. But when I look around at the people who give that unsolicited feedback, none of them have lives that I envy. Not my friend Jenna Sanborne, who sits across the table from her husband and two kids, wondering how she ended up there, if she’d be happier somewhere else, and how long she’ll stay. Nor my fraternity brother Pat Landry, who spends every conversation complaining about how he hates his job and doesn’t have time to get a new one, but just went on his third orgy-filled-cruise for the year. The uninspired, who wander from moment to moment, relationship to relationship, too scared to look inward to try and figure out what they want or who to be or where to go. To get up from their chair and learn to wander.

Sometimes I wish I had the courage to be like them. To relax and let fate take me by its reins. But I can’t help but notice how the lax seem lost. Delicate and fragile. Too affected by the random misfortune that comes with being alive, where cancer or job loss or depression or heartache throw them so violently for a loop. Because what do you do with yourself when you’re lying in bed at night, down on your luck, and life has handed you a set of cards that you no longer feel like playing? How do you convince yourself to mosey back over to a path if you’re unsure of where it goes?

Four years ago, life dealt me an unexpected hand. I developed a balance disorder, stemming from my ear, which caused me to be slightly dizzy at almost all moments of the day. How fast so many of the visions I had for myself vanished. I’d never again hike, fearful that I might fall, I’d never again do standup comedy, afraid that the dizziness would cause me to appear slow on stage, and I’d never again fall in love because no one would ever risk loving a person who was already so broken.

Every few months or so, my health would worsen and then get better and then worsen and get better and worsen. I was unmoored. I saw around forty physicians and even moved across the country to seek treatment. But time and time again I sat down and reset my expectations, making a new life plan that operated under the assumption that all suffering in my life was simply due to the difference between how I expected my life to be, and how it actually was.

I kept mapping and charting trying to figure out how to live a life, albeit different than the one I had planned before, of which I could still be proud. And it was through this constant reflection and acceptance that I felt comfortable again being able to wander.

It’s not easy making big changes. To feel proud enough of yourself to take risks. I don’t believe that simply writing “I am worthy” on a sticky note conjures any relevant amount of self-love. I don’t believe that we are destined to go to bed each night appreciative of who we’ve become, nor are we meant to wake up each day grateful to be alive. But I do believe that we have the ability to change the way we internalize the things we’ve done and things we’ll do by mapping out the time we hope to have left in a way that makes it seem, to each of us, worth the while.

That guy I was dating a bit ago, the one that wasn’t “Jewish and didn’t go to college”, that my mother didn’t like: Matt.

He and I were once on vacation when out of my jacket fluttered a photo, a reminder that, unbeknownst to me, my mother had hidden. It was a picture of “New San Diego Community College Graduates” all throwing their caps into the air.

It fell to the ground.

Matt picked it up.

"What's this?" he asked. 

"Oh, nothing. Just a thing for work," I lied.

He saw something scrawled across the picture in permanent marker. 

“What’s GFN?” he asked.

“GFN” was the nickname my mom had for him. It meant "Good for Now."

Shortly after, we broke up.

My mother does what she can to bring her vision board to life. And though I won’t take the stance that her scribbling of dreams for her kids, or photos of Dustin Hoffman actually changes the way her journey unfolds, I do know that making her colorful boards orients her to write little notes to her children, or continue to go on more dates, or move to Japan. Her board gives her the confidence to wander.

It’s the start of a new year — my mother is now happily married to a man who looks almost identical to Dustin Hoffman, and I am seeing a guy who, by no conscious choice of my own, passes muster on her shallow “educated and Jewish” tests.

It’s been six months since my last planning sesh, and I now have my dizziness mostly under control, I’m working on a new business, and I spend enough time writing that I currently end most days proud of both who I am and what I hope to become.

But life always has a way of dealing unexpected cards. Perhaps my new startup will fail, my Substack readers will dwindle, and this new guy I’m dating will get hit by a bus. 

No worries. 

I can always make a new plan, get back out there, and wander.

If You Feel Like Planning Along, Here's a Template For You To Copy

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