How To Stay Calm While Chasing Big Goals Cover

How To Stay Calm While Chasing Big Goals

When my best friend and I graduated high school, we came up with “the List.”

We thought about our wildest dreams and put them on a timeline. Three months, one year, then five, then ten. There was only one problem: they were all stupid goals. Like, downright delusional.

For starters, our top priority was to become a billionaire. And it only got worse from there. We thought we’d have made it if we managed to…

  • Own a car for at least $100k, a penthouse, and a private jet.
  • Get one of those black credit cards that probably comes with its own yacht.
  • Spend $1,000 in a club in a single night, all cash, and oh, pour some Cristal on the floor.

If you’re not facepalming yet, now would be a good time. I wish I could go back and punch that kid square in the face. But despite the horrendous outcome, there’s one thing I have to give him credit for:

For the first time in his life, he made a conscious effort to think about what he wants.

What Most People Get Wrong About Setting Goals

If you never reflect on your desires, you live your entire life driven by impulse.

This happens to a lot of people when they bury their childhood dreams deep inside and stop questioning the status quo. Wake up, go to work, hit the gym, have a few drinks, zone out in front of the TV. Then, at 63, suddenly realize what you’ve missed all these years.

While we have no way of knowing for sure unless we’ve lived it, the alternative might be just as painful: You’re constantly fretting about what goals to chase. Did I pick the right one for this year? What if this is a mistake? Was it a good call to leave that job? When am I gonna have time to paint?

We tend to think tracking our goals will always lead to a better result, but that’s only true for the completion of the goal itself, not how we feel about it when we’re done. We miss the bigger point:

Keeping score always leads to anxiety.

The price of tracking your goals is doubt. Worrying is a natural, human behavior; one that is inseparable from the process of organization. It’s true, we can go after both our big goals and the small ones, but one always comes at the expense of the other. The tension of having to manage the ratio, the pain of choosing which to sacrifice, over and over again, will never go away.

As a corollary, the person who satisfies only their short-term needs might eat one big bowl of regret some day, but for 40 years or so, they avoid the stress of managing desire. That’s no small thing. Again, we can’t know for sure, but my guess is that much of that same regret is also baked into our prioritization of dreams. Except it’s unconfirmed. We create it in our own heads by doubting our decisions.

The result is that we can either ignore our goals, ride the wave, and roll the dice with long-term regret or suffer constant, short-term discomfort from fretting about our choices, but feel more in control about the life we build.

From a cosmic standpoint, this is rather hilarious. There’s a good chance we’re all left with the same amounts of joy and pain. The procrastinators and the go-getters. The only part we get to decide is how we distribute them over the course of our lives.

Most of us opt for the latter. It often feels better to have chosen something, even if the choice ended up being wrong. At least you made the call.

But the behavior that follows is somewhat paradoxical.

Adrift the Ocean of Desire

When I made that list eight years ago, I, too, chose to choose.

Since then, I’ve written, crumpled, highlighted, marked, taped, and trashed hundreds of lists of goals. Because sometimes, the only way we can deal with doubt is by caving. By saying “alright, I think I screwed this one up,” and tossing the plan.

As a result, we might sway wildly between extremes. One day, you might decide to become a world-class music producer and that, from here on out, the only thing you’ll focus on is releasing a new beat every week. But four weeks in, you realize the memories of Friday night poker with your friends are more important. So you stop.

That cycle might go on for years. Ironically, this is not unlike the mindless procrastinator, who reacts to all the antics of his mind instantaneously. And while some of this course-correcting is normal, if we do it too often, it’s as if we’re adrift at sea, tossed about by waves of desire, with zero control at all.

But wasn’t that what we originally demanded? Isn’t it control that we chose to pay the price of stress for? What a mess! Obviously, there’s no perfect solution to all this. But I’d still like to show you one tool that has particularly helped me in dealing with it.

I call it my Not-A-Bucket-List.

A List With a Strange Purpose

A lot of useful metaphors exist that can help us balance our goals. There’s the story of the teacher, filling up a jar with rocks, pebbles, sand, then water — to show the most important things have to come first or there’ll be no space left.

Then, there’s the tale of Warren Buffett and his pilot. Apparently, he told him to make a list of his top 25 career goals, then split it into the top five and the remaining 20. Instead of telling him to allocate his time equally, Buffett then said he should toss the second list and avoid it at all cost.

A Not-A-Bucket-List is basically the opposite of the second list. Unlike goals 6–25, which still feel like you should prioritize them, there’s nothing on there that means a lot to you. Nothing you’d die regretful of, having left it undone. It is a list of all the things you’d be happy to sacrifice for a greater goal.

I keep mine in my notes on my iPhone so I can add to it whenever, wherever. I use five categories:


I really wanna buy a sandwich maker. Except I’ve been getting along fine without one for the past eight years. I’ve also been procrastinating on buying a new watch after my old one broke. And ordering a 23andMe kit. Don’t even get me started on online courses. Then again, ¯\_(ツ)_/¯.

Books & Reading

If I read all the books and articles recommended to me, I’d be the smartest guy on the street — because I’d literally be homeless. Life is short and I wanna get things done. I love reading and I do a lot of it, but there’s never enough time to read everything.


Watching a movie a day and then writing about it is the easiest way I can think of to start your career as a writer. And while I write about movies a lot, I already have more ideas than I can write about. Sorry, Netflix backlog, you’re gonna get longer.

Fun Business Ideas

It would be really cool to start gaming again and make a Youtube channel. Or create mashups of my favorite songs. Produce electronic music, rap, and open a café. But none of it is worth sacrificing what I’ve built with writing so far.


We all like to tell ourselves we’re a good friend and to a few people, we are. But most of our kindergarten, high school, and college friendships fade as we get older. Instead of convincing myself I can hold on to all of them, I’d rather admit that other things are more important, but note the names I fondly remember. This way, I can always pick up the phone and call them if we happen to find ourselves in the same place at the same time.

The goal of a Not-A-Bucket-List is to never look at it.

It shouldn’t become your go-to list to pick the next movie. Just the place you turn to if you want to watch a movie and haven’t already got one in mind. Nine out of ten times I open it, it’s to add something, not pick something.

That’s how a Not-A-Bucket-List helps you find peace of mind. Because the little things are accounted for. Even if all they do is catch dust.

The Question That’s Left

Becoming aware of our desires is a gift. The first time it happens, we dare to dream big. Too big, often. Soon, we realize we’ve awoken to a new, just a different struggle: balancing our lofty aspirations with our modest goals.

And while the emotional turmoil of forsaking goals altogether might be the same, picking our battles and keeping score gives us the comforting feeling of having done the best we can do. That’s an effort worth making, but one that is easily negated when it’s met with constant doubts and countless, unnecessary changes of plans.

A Not-A-Bucket-List can help you acknowledge the fact that you, like all of us, have many dreams and plans, but not enough time to make them all come true. After making and throwing out many goal lists over the years, I find it one of the most useful tools to stay calm while trying to accomplish big things.

It’s almost as if the sole act of writing something on that list makes it less important. Maybe it does. But what’s most beautiful is that there’s ever room for more. Because the biggest question will always be left:

What are you willing to happily sacrifice all the little things for?