The Ultimate Goal Setting Tool

I love writing this newsletter.

There are plenty of reasons, but at the top of the list is the fact that I get to take you all on a journey with me. Not a physical journey—though it would be fun to do a Curiosity Chronicle retreat someday!—but a learning journey.

I’m able to share new insights and perspectives in *real time*.

This isn’t some academic newsletter where I lecture you on truths and personal wisdom—this is simply me sharing ideas, frameworks, and models that I am battle-testing on my own journey.

I am not a teacher—I am a student, learning alongside all of you.

In that vein, today’s piece will share a new learning: the power of Anti-Goals.

An Introduction to Anti-Goals

At the start of 2022, I shared a piece called The Goal Setting Guide—a breakdown of my framework for setting—and smashing—goals.

Shortly after I shared the piece, however, I came across the intriguing concept of “anti-goals” from my friend Andrew Wilkinson. I began to wonder if my goal setting framework was in need of a refresh.

I like to personally battle-test new concepts before I share them publicly, so I started establishing “Anti-Goals” for all new projects.

Everything changed.

It quickly became a staple for:

• Planning for new projects
• Designing my life
• Creating self-improvement plans

So with sufficient battle-testing behind me, I'd like to share how to leverage anti-goals to level up your goal setting process.

The concept is grounded in inversion—a foundational mental model that says that complex problems are often easier solved backwards vs. forwards.

Inversion was made famous by one quote from Charlie Munger:

All I want to know is where I’m going to die, so I’ll never go there.

With traditional goals, we envision the optimal outcome. We then build systems that will—hopefully—lead to that outcome.

This is important and necessary—but it’s incomplete. Anti-goals leverage inversion to complete the picture.

Anti-goals are the things we DON'T want to happen—either as final outcomes or along the way.

I think of anti-goals as being about avoiding the Pyrrhic victory—a term coined after King Pyrrhus of Epirus, who suffered devastating losses while defeating the Roman army in battle in 279 B.C.E.

The term is now commonly used to refer to a victory that takes such a terrible toll on the victor that it might has well have been a defeat.

My friend Shaan Puri, another proponent of anti-goals, elaborates:

What if your dream was to be a musician. And guess what - you did it! But while you’re touring the world, you gain weight, get addicted to drugs, your marriage is in shambles, and your kids don’t recognize you....you won the battle but lost the war.

Anti-goals allow you to win the battle AND the war!

The Anti-Goal Framework

Ok, so how do you leverage anti-goals in your goal setting process?

The generalized version involves four steps:

1. Choose Your Arena
2. Establish Traditional Goals
3. Invert the Problem
4. Establish Anti-Goals

Let’s walk through each step:

Choose Your Arena

The arena is the "project" you’re going to be working on.

A few broad categories to consider:

• Personal
• Work
• Health

Your arena should be a specific project under a larger category. It’s the place where you’re looking for achievement, progress, or growth.

Establish Traditional Goals

These are your standard goals—the desired outcomes from the chosen arena. This should be easy, as it’s familiar.

A few examples of traditional goals:

• Run a 6-min mile
• Build a 100,000 sub newsletter
• Promotion to VP
• Create a top-25 podcast

Clear, big picture traditional goals are important.

Note: As I covered in my Goal Setting Guide, it’s often helpful to have short, medium, and long-term traditional goals. Experiment with what works best for you.

Invert the Problem

To invert, ask and answer a few questions.

In the pursuit of these traditional goals:

• What is the worst possible outcome?
• What systems would lead to that?
• What daily actions would I regret?

In short, ask yourself what you would view as winning the battle but losing the war.

Establish Anti-Goals

Now work backwards to establish your anti-goals—the outcomes you DON’T want.

James Clear refers to traditional goals as rudders. Expanding on this analogy, if traditional goals are the rudders that set your direction, think of anti-goals as the map that tells you where the rapids are.

A thoughtful, clear map keeps you on smooth waters.

An Illustrative Example

It can be a bit confusing in the abstract, so let’s look at a recent example from my own life…

Choose Your Arena: Physical Fitness

Establish Traditional Goals:

• Run a 6-minute mile
• Under 8% bodyfat
• Deadlift 500 pounds

Perhaps a bit too ambitious at age 31, but it feels doable if I’m dedicated (and if I get any sleep post baby arrival)!

Invert the Problem:

What does the worst possible outcome look like? Letting it consume my entire life!

Constantly stressing about what workouts to do and about what foods to eat. Working out for 3 hours per day when I want to spend time with my family and friends.

Breaking it down further, what actions or systems would lead to that worst possible outcome? Trying to do everything myself.

Managing my own research on workouts and food. Trying to write, track, and manage my own workout and diet plan. Not scheduling fixed windows for workouts.

Establish Anti-Goals:

1. Never think about workouts. Hire a trainer to write workout programs.
2. Never think about diet. Buy pre-prepared healthy meals.
3. Never let workouts consume my life. Schedule 90-minute blocks at the same time every AM as my workout window.

Putting it all together, my fitness project now has a complete picture:

• Traditional Goals:
• Run a 6-minute mile
• Under 8% bodyfat
• Deadlift 500 pounds
• Anti-Goals:
• Never think about workouts—hire a personal trainer.
• Never think about diet—buy pre-prepared meals.
• Never let workouts consume life—schedule 90-minute blocks.

I know where I want to go, and where I want to avoid—my rudders are set, and I have a map of the rapids.

As another example, in his original blog post on the topic, Andrew Wilkinson sketched out how he established anti-goals to design his work.

In this example, Andrew and his business partner wanted to pursue success and wealth creation, but not at the expense of peace of mind. Establishing anti-goals to sit alongside their goals allowed them to do both.

Conclusion

To summarize the Anti-Goal Framework:

1. Choose Your Arena: Select the project you are going to be working on.
2. Establish Traditional Goals: Set the specific desired outcomes.
3. Invert the Problem: What would it look like to win the battle but lose the war?
4. Establish Anti-Goals: Set the specific outcomes you DON’T want.

So as you take on your next project, give this framework a shot. Establish anti-goals to sit alongside your traditional goals.

Win the battle AND the war!