If you were given a room of 200 people, and only had time to ask one question about each person, which question would you ask to guess whether or not they would be wildly successful in life?
The obvious candidate questions would be, “are you smart?”, “are you ambitious?”, “hard-working?” But, as I think about this question, the more I feel that these would fail.
Plenty of smart people accomplish little. Some studies show  beyond being moderately smarter than average, intelligence is only weakly correlated with success. In other words, being stupid hurts you, but being a genius won’t guarantee accomplishing greatness.
Ambition also seems like the wrong adjective. It’s certainly necessary, but it seems more reflective than predictive. As you become better at something, your ambitions increase. Nobody would say a thermometer is the cause of hot weather, and while ambition probably plays some role in generating success, I’d wager there’s a lot more correlation than causation.
Effort also matters, but it isn’t terribly discerning. If you knew how hard-working 200 people were, I doubt it would narrow your options for guessing success much. Some moderately hard workers will greatly outperform uninspired burnouts.
I believe a much better question for whether someone will be successful is to ask: do they build interesting things?
Cool Projects as the Signal for Big Accomplishment
I like this question because, first, it’s far more limiting than the more obvious questions. What percentage of people are ambitious? Maybe half? But ask which people are building interesting projects, and now I’d guess the number drops well below 5%.
Knowing who is hard-working in a crowd of 200 doesn’t say much. But if you knew that five of those people were working on interesting projects, I think it would be much easier to answer who will accomplish something great.
Interestingness is also a better dimension because projects are rarely formally measured by it. Instead we ask how hard it is, how much money it makes, how long it will take and how will it benefit society. To evaluate something by asking, “is it cool?” seems childish.
Why Build Interesting Things?
I feel there are a few reasons why working on interesting projects might cause great accomplishments.
First, interesting projects allow you to sustainably master a craft. If it takes tens of thousands of hours to become world-class at a particular skill, then this is an effort which must be sustained over time. That means willpower, guilt or external pressure won’t work—you have to actually like what you’re doing, which is a lot easier if what you’re doing is interesting.
Perhaps the biggest reason to choose interesting projects has nothing to do with them being intrinsically better than boring ones. Rather, interesting projects are easier to keep working on during the long gaps between external reinforcement. Boring projects tend to be discarded as soon as the prestige or money wears off.
Second, interesting projects allow you to attract people who help you do more. This was the biggest surprise in running this blog. That it enabled me to get in touch with people who would otherwise be outside the sphere of influence of a regular university student. I now get email from entrepreneurs, authors and even female rappers  who like the ideas and want to help.
One of my favorite bloggers, Chris Guillebeau , has a maxim that has stuck with me, which loosely paraphrased is, “consider adventure over productivity.” Interestingness may be a more important criteria than sheer volume of work, since the adventure attracts people and opportunities which efficiency cannot.
Interesting projects also have a way of evolving into bigger accomplishments. Twitter was originally a side-project at Odeo. Dell began with a student wanting to build computers out of his dorm room.
I’m often asked where I got the idea to start a blog which will soon be my full-time job (I’m finishing my last term of university). The secret is, I didn’t.
Instead it started as a small project I found interesting and grew from there. I had hopes I could eventually turn it into something bigger, but in the beginning, it was just me, a default WordPress theme, and a few poorly written articles. It was interesting, however, so I kept working on it.
Becoming a Builder of Cool Things
People ask the wrong questions when they start projects. They ask things like:
- Does it pay well?
- Will it look good on a resume?
- Is it popular?
- Will people admire me for it?
- Is it fun? (Note: fun is important, but interestingness is a much more selective adjective)
I even think that picking projects because they are important is probably the wrong criteria as well. Interesting things need to be at least minimally important, otherwise they are boring. If nobody cares about your idea and it doesn’t have any personal significance, it probably isn’t interesting.
However, choosing to work on ideas because they are important tends to ensure they aren’t too much fun. While fun isn’t a great criteria on its own either, it’s a necessary component to start a project you’ll actually finish. Without income or peer pressure, boring, important projects get dropped pretty quickly.
Obviously, there are mandatory projects you don’t get much choice in. I feel work and academics actively select against interestingness (at least until you reach a high enough level). That’s probably why so many truly interesting projects start as part-time ventures.
Why Aren’t More People Working on Interesting Projects?
All of this makes me wonder why more people aren’t working on interesting projects. Why, in a room of 200, would you reasonably expect at least 25-50 ambitious, smart or hard-working people, but far fewer actively building cool things?
Perhaps it’s because ambition, hard work and intelligence are easy to spot and easy to reward. When someone breaks our mental model and works on a project that is interesting, but doesn’t fit a standard life path, we have a harder time evaluating it. Maybe that’s also exactly the reason more people should start.