Follow your heart — with caveats

“Follow your heart” is squishy advice. 

It’s a Goop headline. It’s a bumper sticker. It’s something you imagine Adam Neumann plastering on custom WeWork shot glasses so he can wax poetic about “elevating global consciousness” in between belts of Jose Cuervo.

“Follow your heart” gets a bad rap, okay?

I think that’s because it is sometimes co-opted by people to mean, “Do whatever you want.” It feels woo-woo and amorphous. It’s associated with a certain kind of unreliable and irrational behavior.

But I don’t think this bad rap is well-deserved. I think “follow your heart” is actually a very good answer — and actually, the only answer — to a certain set of questions that life throws at us. 

The problem is that it’s very hard to make it actionable. How do you know what your heart wants? 

Let me explain.

.   .   . 

These days I have my dream job.

What I do merges two big sides of me. On the one hand, I have a bit of the sensitive, emotional writerly type inside of me. On the other hand, I have a bit of the ambitious business nerd and programmer inside of me as well.

My current job satisfies both. It’s surprisingly great.

So, the question is, how did I get here? Of course, there was a ton of privilege involved. But I think there were a couple of other things worth talking about as well.

It may seem obvious now that starting a newsletter business was the right thing for me, but it was very non-obvious before I started doing it. In other words, it may seem like I sat down and reasoned through a bunch of different ideas, then settled on one that best aligned with all of my interests, and then started it.

In fact, it wasn’t like this at all. Instead, it was a process that I felt my way through. I didn’t have the answers at the beginning. 

As cliche, and weird, and trite, and almost icky as it sounds to say, I followed my heart to get here — zigging and zagging through different ideas until one of them turned out to be the right one for me. 

Along the way I also learned that my heart isn’t perfect. That it makes mistakes too. My heart is noisy. It attaches to new things. It swerves towards prestige; it steers me away from guilt. I often have to filter through these feelings in order to allow it to steer me properly. 

So I’ve come to a bit of an understanding with my heart. I’ll pretty much do what it says — but I filter it through a framework first. Just to make sure it’s not leading me astray.

Rather than “follow your heart” I’ve come up with a better formulation:

Follow your heart — with caveats.

Some questions require heart-following

Let’s back up.

Last week we talked a lot about being kind to our ideas. About not throwing them out just because they seemed “bad.”

If you’re being kind to your ideas, and you’re committed to working on them, the next logical question is: “Which idea should I work on first?”

A lot of people asked me that question after last week. It’s an interesting one, because it’s the exact one that I had to grapple with in order to find this job — the one I love to do. 

So I think I have some authority when I say the following:

There’s no such thing as a bad question, but there are some questions that you’d be better off not asking. 

“Which idea should I work on first?” is one of these.

Reasoning and logic generally are shortcuts to finding answers to questions, but sometimes there is no shortcut.

Now, why would that be?

.   .   .

In computer science the complexity of an algorithm is measured by how quickly the algorithm can be run on a computer. 

Programmers get lots of computer science points when they can turn algorithms that solve problems in a “slow” way into algorithms that solve problems in a “fast” way. They do this by finding shortcuts to make the algorithm solve the problem by doing fewer computations.

It turns out, in all likelihood, that certain kinds of problems just can’t be solved any faster. These are problems where the solution has to be brute-forced.

A good example is password cracking. Imagine, for a moment, that you’re a hacker trying to guess a user’s password in the most secure system in the world.  How would you get into the system? 

Well, you’d have to guess the password. And the only way to do this is make a list of all of the possible passwords (which is an infinite list!) and guess each one in turn. 

It occurs to me that some human questions are, effectively, like this as well.

“Which idea should I work on first?” is one such question. But there are many more.

It’s any situation in which you have low information and there are an effectively infinite number of options to choose from.

You can tell you’ve encountered one of these questions when you spend lots of time circling around different answers over and over again. Another way to tell: when you ask your friends what to do and you’re told to “follow your heart.”

That advice is usually not particularly helpful, but what it’s really saying is this:

Trying to answer this type of question by sitting in your room and thinking about it is like trying to guess a password without brute forcing it. It’s maybe possible, but very likely to take many many years and you’d be better off just trying a bunch of passwords instead.

The longer you sit and theorize the further you get from actually finding the answer. You need to get into the brute force business.