I can’t remember where I first heard about desire paths.

Landscapers are apparently the people who know the most about this phenomenon in modern life. But we all see it – the worn footpath next to the sidewalk bit that didn’t quite curve enough or the improvised bike path next to the stairs in a grocery parking lot. People find their own way.

There’s a critical new skill people are developing around quantified self. And I think that skill set lies at the intersection of desire paths, habit formation and self-observation.

I wrote recently about retraining myself to run (most) every day. Through that, I learned about triggers and chaining behaviors to make new habits.

A lot of creating a successful new habit is figuring out how it will fit into your existing habits. You look for something you already do, and you chain the new behavior to it, like “AFTER I do X, THEN I’ll do Y.”

What makes a good anchor habit?

Anchor habits seem like the things you do naturally, that seem instinctual. Picking out these key moments from the fabric of daily living is the trick: finishing breakfast, getting out of bed in the morning, feeding the cat, opening the refrigerator, putting on shoes, getting dressed, taking a shower… I could go on.

Some research says that 93% of our behavior is predictable. We walk the same paths, eat the same food, talk to the same people.

The critical insight for adding habits is finding the right place to add something new. Self-observation to find these moments is a skill, and we’re learning a great deal about it from the quantified self movement.

Desire paths and observing yourself

I now think of my daily patterns as my own personal desire path. The way that I get out of bed in the morning, drinking coffee, reading the newspaper, the moment I put on my running shoes, checking email – all of these things happen in a predictable sequence. And I’ve managed to add new habits in the space just after a few of them.

One practice I took from my first job was keeping a work diary. I document from hour to hour what I’m doing. For our startup, I have a log of tasks I’ve completed since last September, for example.

From my diary, I’ve noticed I can get about 6 things done in an average day. A “thing” is something that will take about 45 minutes. On really productive days, I can get up to double that. But once I hit six things, I give myself a break, because I’ve met my normal level of task completion.

I like metrics like this one to help me feel accomplished every day. Otherwise, the days and weeks feel like an endless stream of tasks that I never get in front of. It also helps me estimate when I’ll get to any particular task in my backlog.

And, of course, there’s more to my task list than 45-minute tasks. But the generalization I was able to make from just tracking my work hourly has been a powerful feedback mechanism for understanding myself and increasing my daily happiness.

But what does that have to do with habits?

One thing that I noticed was how tense I was at the end of the day, and that I really didn’t want to exercise right after finishing a 9 or 10 hour work day.

And for a look at my typical day before my new running habit: I woke up between 5-5:30am, had coffee around 6:15am and started my work day at 7am. Two of my coworkers are on East coast time, and my husband gets off work at 5pm – so I try to end my work day around 4:30 or so.

I struggled with fitting in a run before having coffee with my husband, or during lunch, and especially did not want to do it after work.

So after considering my task load, I decided that I would still be able to get enough work done even if I didn’t start work right at 7am. I decided to go for my run right after having coffee and reading the newspaper in the morning.

I tend to spend 10 minutes or so around 6am triaging email, but now start my work day around 7:45 or 8am. I’m two weeks into a solid pattern that makes me feel so much better, every day.

My lesson: trying out a few different things is the key to finding the right place and time in my schedule for a new habit. Knowing about my personal productivity also gave me the confidence to change what I was doing without feeling guilty.

I didn’t give up after failing to start a running habit the first few tries; I just assumed that I needed to find the right time for it.