There is an old saying that if you can find something you love to do, you’ll never work a day in your life. But this is probably bad advice.

Here is a simple graph, from Seth Godin, to help explain:

The problem with fun things (y-axis) is that they’re fun. So lots of people want to do them. And if there’s a small or no market for said fun thing, then it’s probably a hobby. (Hobbies are still important.)

Sometimes you can be fortunate where something that previously had no market eventually has a big market. Take, for example, tinkering with computers in the early days.

This is what Chris Dixon was getting at when he said that what the smartest people do on the weekend is what everyone else will do during the week in ten years.

But if this doesn’t happen or if a big market already exists — and you do want to be successful at something fun — it’ll likely follow a power law.

Meaning, you’ll need to be the very best in the world and it’s almost certainly going to be a “slog”. (Bottom right quadrant.) One example of this would be the phenomenon of “starchitects.”

And that’s pretty much it for the fun stuff. The rest of this graph is for things that are difficult, which means that 3 out of these 4 quadrants are difficult and/or a slog.

This is not nearly as much fun as not ever working.

I have a bit of an obsession with my calendar, lists, and goals. On the home screen of my phone I have Wunderlist, Evernote, Google Drive, and 2 calendar apps (more on that in a second).

This obsession is probably one of the reasons I write this blog. I like writing, drawing, and documenting things. It helps me sort through my thoughts. I have everything from a list of cities I want to visit to a list of billion dollar business ideas (yes it’s really called that).

But the other reason I like to keep lists is because – as I said in this post – I’m trying to be cognizant about overcommitment. And when I write things down, it serves as a reminder of what I’m doing and what I’m allowed to focus on.

One of the ways I do that is through repeatable goals (or disciplines). These are non-negotiable things that I’ve committed myself to and that I just have to grind out – such as writing on this blog every day. I can tell you that some blog posts come out a lot easier than others. But I’m a firm believer that there are few substitutes for just showing up every day and putting in the work.

On that note, let me tell you why I have 2 calendar apps on my phone. I’ve been testing out the latest version of Google Calendar because of a new feature they rolled out this month called Goals.

What it does is automatically schedule repeatable goals. So for instance, you could tell it that you want to work out 3 times a week for 1.5 hours each time and that you prefer to work out in the evenings. It will then go and find 3 times for you to do it every week for all of eternity. 

If a conflict arises, that’s no problem. As soon as you enter another appointment, the app will automatically reshuffle your calendar goals to make sure that you still get your 3 workouts in. It’ll even learn your preferences as you make changes to these appointments over time. 

So far I’ve been finding this feature really useful. I used to do this for myself manually, but now I have a computer that does it for me. Even better.

It’s also a glimpse into the future that Sundar Pichai, CEO of Google, was talking about on a recent earnings call:

“We’ve been investing in machine learning and AI [artificial intelligence] for years, but I think we’re at an exceptionally interesting tipping point where these technologies are really taking off,” he said. “That is very, very applicable to businesses as well. So thoughtfully doing that externally we view as a big differentiator we have over others.”

“In the long run, I think we will evolve in computing from a mobile-first to an AI-first world,” Pichai said in closing. “And I do think we’re at the forefront of developments.”

For the past 5 years, it’s been all about mobile. But now much of the tech community – including the CEO of a pretty big company – is saying that artificial intelligence is next. What do you think this will mean for cities?