A Simple Plan to Win the Year Cover

A Simple Plan to Win the Year

There’s this pithy quote floating around the web that I really like:

In school, you’re taught a lesson and then given a test. In life, you’re given a test that teaches you a lesson.

The one thing I don’t like about it is that it makes it sound like you have to wait to be given the test either way. You don’t. You can decide to take your own test any day of the week and when you do, you’ll learn a lesson instantly.

At the end of 2015, I designed such a test for myself: Learn something from a new book every day, whether that’s a chapter, a full book, a summary, or tons of interviews, and then write about it. Every day for the next year. The day I made the decision I already learned the first lesson.

The New Year Starts Today

In Do The Work, Steven Pressfield writes:

“Don’t prepare. Begin. Remember, our enemy is not lack of preparation; it’s not the difficulty of the project or the state of the marketplace or the emptiness of our bank account.

The enemy is Resistance. The enemy is our chattering brain, which, if we give it so much as a nanosecond, will start producing excuses, alibis, transparent self-justifications, and a million reasons why we can’t/shouldn’t/won’t do what we know we need to do. Start before you’re ready.”

As I prepared the website I thought “why not start writing also? It’ll be like a rolling start in a car race.” More like flying.

A big part of why 92% of people fail their New Year’s resolutions is that they think the switch is magical if they flip it on January 1st. But the switch is never magical and you can flip it any day. You can start a new year any day of the year. You’re not a calendar.

When you do it in December, you can fail a lot before January 1st and you won’t need pseudo-motivation to start because you can just keep going.

An Ode to December

Ever since I learned that lesson, December has become my busiest month of the year. Not with business, but with thinking. “What goals make sense for the next year? How can I make them simpler? What can I do to start today?”

Here’s what I’ve come up with this year.

1. Set a Simple, Insane Goal

Talking about cryptocurrency investing with a successful friend, I asked him: “What’s a good goal for me next year?” Without knowing how much I have, he said: “One million dollars.”

He explained: “Look, last year, around Christmas, I set a completely utopian goal. Not because I need the money. Just because. And I completely destroyed it.”


The obvious but hard to practice thinking behind this is that you can’t get a result that’s ten times bigger without a radically different approach. While everyone’s clawing for 1,000 more followers, can you sweat behind the curtain until you’re good enough to pop up on Oprah?

The path to bigger goals is always harder, less straightforward and more people will think you’re crazy. But it’s also less crowded.

Higher risk, more return. Speaking of which.

2. Completely Detach Yourself From Your Goal

The shrug emoji above is actually quite important. The reason my friend was so comfortable in setting such an insane goal is that he knew he didn’t control even half of it.

“You just do the best you can with what you’ve got, you go all in and then you let go.” Sticking with the one million dollar example, he continued: “You’d need to put in 100k and 10x that. But even if you pull off the first part, 90% of the result is out of your control. That’s fine, but that’s what it is.”

If your first thought is “I want a million dollars,” then your second thought should be “I don’t need a million dollars.” Not now, not ever.

What I like about my friend’s line of thinking is that it doesn’t artificially try to increase the part I control. More control just means more work. If I let go I can aim higher while focusing on less. I’ll probably like where I end up regardless.

3. Put All Your Energy Into 2–3 Core Strengths

Once you’ve placed your target on the moon, you can return to earth, turn your back on it and start digging. For short- to mid-term projects it makes sense to break it all down into small packages. For long-term, life-changing, way-out-there goals, that’s just depressing.

Which activities, if you do them long enough, will get you there? Which of those are you good at? Where have you already built assets you can work with?

Pick 2–3 of your core strengths and find a way to funnel those into your goal. How can you spend more time doing them? What others can you let go? If you’re already going strong, you can just keep going. For me it’s writing, saving a big share of my income and investing that as best as I can.

That’s it. Often, you need to change less of your day-to-day than you think.

4. Let Things Fall By The Wayside

Since this approach is so simple, what exactly I write, how much of my income I save, where I invest it, and so on, are all secondary. As long as I do those things, I’ll eventually get there.

As someone who thrives on plans, this is hard to wrap my head around. “Oh, I don’t need an exact portfolio allocation right now? Right, I don’t.” Even if you can follow a rigid, step-by-step plan, chances are you’ll get bored of it halfway through. But besides robbing you of the fun, tunnel vision also blindsides you to new opportunities along the way.

If a faster train to your goal passes you at the 50% marker, you first need to see it in order to jump on. But even before that, you have to buy a ticket.

5. Start Before You’re Ready

You don’t feel ready now, do you? That means it’s as good a time as ever.

What’s your goal? Can you make it bigger? Let go? Which activities will get you there? How much minutiae can you get rid of?

Don’t wait for life to give you a test. Design your own. If not now, when ever? It’s a new year, after all. And it starts today.

“Only put off until tomorrow what you are willing to die having left undone.”  —  Pablo Picasso