I’m a YC alum from W18 batch, now tinkering with longevity projects to figure out how to live 200 years.

Why Goals Make You Fail

Why Goals Make You Fail

Photo by  Quino Al  on  Unsplash .

Photo by Quino Al on Unsplash.

"You must set ambitious goals to be successful."

This idea was implanted in my mind for decades. I've never questioned the origin of it; I just blindly believed that it's true.

But after failing one ambitious goal after another, I decided to figure out what I am doing wrong.

After 10 years of tinkering and testing different things, I've come up with a framework.

This framework helped me to lose sixty pounds in three months, become a pro canoe athlete, start two companies, get funded by Y Combinator, and move from my small town in Belarus to California for a year.

I'm by no means successful, but I've made good progress in the past five years, and this is what the framework is about. But first, let's dive into goals to understand how they work and why we fail to achieve them.

Why We Fail Goals

People fail to achieve goals because they fail to start.

It's that simple. 

But let's drill down a bit deeper and ask the "why" question: why people fail to start?

And here it becomes a bit more complicated because people fail to start for a bunch of reasons. Some might be specific to their current situation, some might be more general, like messing up the "urgent/important" problem and continually being in a rut.

But the root cause of it is simply a math problem:

Ambitiousness of the goal * time spent thinking about it = total inaction

In other words, the more ambitious your goal is and the longer it's been sitting in your head, the harder it becomes to start working on it because of the massive delta between reality and the outcome you'd have had if you started working on it back then.

Let me give you an example.

I wanted to build a popular blog for two years already. That goal sounded like a real aspiration to me, and I had all the motivation to do it. I even bought a domain name I liked.

I just never started writing.

There were a bunch of reasons to it, but the longer I kept snoozing working on my goal, the harder it became for me to start doing something about it. As a result, I became frustrated about not achieving my dream and gave up on this idea entirely.

Let's map it on a graph to make the idea more clear:

2019-08-20 18.45.26.jpg

The delta between my perfectly planned goal and reality just gets bigger and bigger. So I either have to change the goal (aka give up), or I have to put enormous mental effort into actually starting, all the while continually blaming myself for not doing it sooner.

You can easily see how this problem applies to goals in different domains. Want to start your own gig? Build a brand? Become a successful investor? All of them fall into this reality-outcome delta problem bucket.

But you're reading this article, so that means I somehow fixed it. And I did that by focusing on skills, not goals.

From Goals to Skills

Scott Adams has this beautiful idea about systems which I love:

If your goal is to lose ten pounds, you may wake up each day with failure in mind. The goal is hard to reach, and you are progressing only by small amounts. It takes up all your willpower.
— Scott Adams

He recommends that instead of a goal, you should have a system. In the weight loss example, Scott says a person could instead spend time educating himself about choices, which gradually leads to selecting the right foods. So losing weight becomes a byproduct of the system that the person created.

But systems sound fuzzy and hard to understand for most people.

How do you actually build them? What kind of systems should you create? And how do you make sure they're working well for you?

That's why I went one step further and focused on skills.

Skills are simple

And measurable. Are you good at computer programming? Or writing? That's a much easier thing to figure out than "what kind of goal should I choose?”

Skills are authentic

Most of your goals are actually not yours.

We're highly mimetic creatures and copy each other’s goals all the time.

But it's much harder to do that with skills because you have to think hard about choosing the right ones (we'll explore how to do that in a second).

Skills are actionable

Skills eliminate the reality-outcome delta problem. 

Let's get back to our blog example for a second.

If I have this ambitious goal, build a popular blog, what kind of skill I'm trying to get better at? Obviously, writing. 

And just by following this simple question, I don't have this crazy audacious goal anymore. I figured out that I want to improve my writing skills, and there are a bunch of ways to do that.

Skills help you escape competition

It's tough to be number one at something in the world. If you pick 100m running as a skill than you have to beat Usain Bolt, which might be a tough one.

Scott Adams has a blog post on how to build your career by getting in, say, the top 25 percentile at three or more things. 

If you select several different skills that you’re good at and combine them together, you become the only person in the world who can do those things in the 25th percentile.

For example, if I take good writing skills plus good storytelling skills plus good drawing skills plus good understanding of molecular biology of the cell, I might end up being one of the few people in the world who can create powerful illustrated stories about how biology actually works.

And it's much easier to be top 25 percentile at five things than it is to be literally the number one at something.

Skills generate luck

If you become really good at something, opportunities will start coming to you because of your unique expertise and character.

Enter Naval:

For example, let’s say that you’re the best person in the world at deep sea underwater diving. You’re known to take on deep sea underwater dives that nobody else will even attempt to dare.

Then, by sheer luck, somebody finds a sunken treasure ship off the coast. They can’t get it. Well, their luck just became your luck, because they’re going to come to you to get that treasure. You’re going to get paid for it.

Now, that’s an extreme example. The person who got lucky by finding the treasure chest, that was blind luck. But them coming to you and asking you to extract it and having to give you half, that’s not luck.

You created your own luck. You put yourself in a position to be able to capitalize on that luck. Or to attract that luck when nobody else has created that opportunity for themselves.

Naval covers the idea of different types of luck in detail here.

Skills are antifragile

When you choose skills you're a natural at, you become antifragile. Whatever happens, you'll benefit from the outcome.

With goals, you don't have that freedom. No matter how ambitious your goal is, you're locked up in it, you're in this rabbit hole with tunneled vision, and you miss all the beauty of randomness in life.

Let's come back to our blog vs writing skill example.

If you bet on building a popular blog as a goal, you'll most likely fail. If you choose to improve your writing skill instead, you'll be progressing each day.

The idea of small wins is essential to happiness. As Taleb writes:

"Your happiness depends far more on the number of instances of positive feelings, what psychologists call "positive affect," than on their intensity when they hit." 

In other words, to have a good life, you should spread these small improvements across time as evenly as possible. This is what you do by focusing on skills instead of goals.

Now, let's explore how to choose the right skills.

How to Pick the Right Skills

Let's pretend you have some goals you've been slacking on for years (or maybe it’s just me).

Mine were building a blog and investing. I was thinking about this idea of creating a blog for 2 years, but never actually started writing. And now I have this 2-year delta which makes me feel bad about myself.

Here’s how we’ll solve it.

What I want you to do is to travel in time with me. Not too far, just 2 years into the future. Once you're there, let's work backwards.

Ask yourself this question:

In two years from now, what kind of things I wish I’d started doing today?

The question makes you think about actions, not goals.

For me, the answer was: writing, investing, and saving up some cash. Your list may actually be bigger, and that's totally fine (mine was 11 items, I just cut it down for the sake of clarity in this article).

Next, I want you to filter that list to choose the skills you're "a natural" at. Enter Naval:

Everyone is a natural at something.

We’re all familiar with that phrase, a natural. “Oh, this person is a natural at meeting men or women, this person is a natural socialite, this person is a natural programmer, this person is a natural reader.” So, whatever you are a natural at, you want to double down on that.

And then there are probably multiple things you’re natural at because personalities and humans are very complex. So, we want to be able to take the things that you are natural at and combine them so that you automatically, just through sheer interest and enjoyment, end up top 25% or top 10% or top 5% at a number of things.

Ask yourself:

From this list, what are the things I’m “a natural” at?

What can be done through co-founders / partners / outsourcing / delegation?

Finally, let's make it actionable. Ask yourself:

What’s the tiniest thing I can do this week such that by doing it I will become better at [skill]?

I went ahead and signed up for David Perell's Write of Passage to make my writing better.

Write down your actions. Here, we're playing up your fears by decreasing the mental effort that you need to start doing something about the thing you're excited about.


Focus on skills, not goals. Find the thing you're a natural at, make it actionable, and

just don't quit.

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