Getting Better at Figuring Things Out

Over the years, I’ve employed quite a few people. Sometimes it will be a contract for a one-time job. Other times it will be for regular staff.

In both cases, there’s a certain quality some people possess that I’ve found immensely valuable, but rarely shows up on a resume. If I had to describe it, I would say the quality is roughly “being able to figure things out.”

Some people are good at figuring things out. You can give them a goal, sometimes with ambiguous instructions or constraints, and they will find a way to do it. It may not always be the way you envisioned (especially if your instructions are bad) but these people rarely get stuck. They will find some way to figure it out.

Other people are terrible at figuring things out. You can give them extremely detailed instructions and somehow they still get derailed because of an incredibly minor obstacle. Assigning such people tasks with any ambiguity is always a disaster.

Employing people brings this quality into contrast, but it’s not just a skill to be exploited by employers. People who are good at figuring things out for their bosses are generally even better at figuring things out for themselves. They make good entrepreneurs, inventors, researchers and artists.

What Makes Someone Good at “Figuring Things Out”?

Intelligence is obviously an important part of figuring things out. Smarter people have an easier time working through the obstacles that may frustrate a particular goal.

However, my inclination is to say that figuring things out is a lot more than intelligence. It’s also a perspective on life. I’ve met plenty of smart people that can’t figure things out. I’ve also met people who aren’t intellectually dominating who, nonetheless, can figure their way out of problems I wouldn’t know where to start with.

People who are bad at figuring things out tend to have unrealistic expectations for the system they’re operating in to conform to rules or norms of fairness. When those rules are violated, they’ve learned that the best response isn’t to investigate, but to wait for instructions.

School is a system that discourages figuring things out. It presents itself as an artificially rule-based and bureaucratic system. Success and failure is based on pre-defined standards. Students are told what will be covered on the test in advance. Exploiting weaknesses in the rule-set is often seen as a form of “cheating” even if the exploit isn’t unethical (I can think of classes where professors would fail students for lack of attendance, even if their grades were good).

Schools also strive for much higher levels of fairness than in the real world. Most universities bar native speakers of a language from attending language classes. Only in an academic setting is this anything other than ridiculous—that you would be forbidden from studying something by virtue of already having mastered it outside of the school system.

Being good at figuring things out is a skill in opposition to scholastic skills. It’s the ability to work within environments where the constraints and standards of success are often ill-defined. It’s the ability to remain motivated despite the fact that there is no standards of fairness at all.

Prerequisite Levels of “Figuring Things Out” to Achievement

Many goals require a certain minimum level of being able to figure things out in order to possibly have any success with them. This may be unfortunate (especially if you’re bad at figuring things out) but it is very true.

I took Ramit Sethi’s online information business building course. Inside the course, some people disliked that the instructions weren’t specific enough—that Sethi focus was on high-level concepts to orient your actions rather than giving a detailed technical walkthroughs.

Of course, this is absurd. If you can’t figure out find and follow numerous free tutorials for setting up a blog or shopping cart, how can you possibly think you’ll run a real business? Running an online business has a minimum threshold of “figuring things out” of which setting up a WordPress blog is well below.

Similarly, I sometimes get emails from people wanting to replicate the MIT Challenge, but need to know the exact hours I worked or exact order of the courses I took. I’m sorry, but if you can’t figure that out, how are you going to perform on the material? What will you do when you find out that a key concept was only explained in a lecture, which isn’t available? Or when you have to take a project-based class that only has rough slideshows as its sole instructional material?

My point isn’t to discourage people from starting businesses or teaching themselves online, of course. I think doing these activities will probably boost your ability to figure things out. It’s rather that the expectations these people have for how detailed and exhaustive instructions should be before they can take action is ridiculously self-defeating.

How to Get Better at Figuring Things Out

Some people are naturally very creative and quick-witted, and will become master hackers, inventors or entrepreneurs. I don’t doubt that figuring things out has a component of natural, latent ability, of which some people are born with more and others less.

Richard Feynman, for instance, the Nobel-prize winning physicist, learned how to fix radios by tinkering with them as a young boy. Eventually he got good enough that he was fixing other people’s radios on his own. That’s a talent for problem solving that would eventually lead him to making breakthroughs in physics and helping design the atomic bomb.

But even if some people are naturally more intuitive at figuring things out, I think it is still a skill one can learn. If you want to get better at figuring things out, here’s how to do it:

1. Do More Projects that Require Figuring Things Out

Figuring things out is a skill, and like all skills, it improves with practice. Even more importantly, it improves best when the skill you’re trying to build is similar to the one you’re practicing. Figuring out how to do paintings will have less utility than figuring out how to do computer programming if your goal is to be good at figuring things out as a software developer.

Being good at figuring things out is, ultimately, not only a set of dispositions and psychological strategies for dealing with frustrations and mental obstacles, but also domain-specific tricks and habits. Many IT people lament when they see that others haven’t learned the domain-specific trick of turning on and off the device to fix transient problems.

2. Become Patient in the Face of Frustration

Figuring things out is often largely a matter of trial and error with patience. It took me five years to figure out how to make blogging a full-time income source, for instance. In that time I tried hundreds of different things until I eventually settled on a combination that worked.

Patience is a mental habit and discipline. The ability to face an ambiguous situation, with constraints which prevent progress, and not give up is one that takes experience to learn.

Although I’ve mentioned the degrading effect I feel the overly rule-based school system has on this ability, figuring things out is obviously related to learning better. Which is why it amazes me that, for many students, the idea that you should sit down and force yourself to truly understand an idea before moving on is novel advice.

3. Avoid Environments Which Punish Deviating from Exact Instructions

A corollary to this would obviously be—if you want employees to be good at figuring things out, don’t punish them for it. Some jobs and environments require exact instructions and deviations should be punished. I wouldn’t want my surgeon to just try things out until I’m healed. But most environments aren’t like this, or if they are, it is needlessly so.

Spending more time in environments which reward figuring things out is a way to get over the psychological objections to it. Those objections can come from a belief that if something is mildly difficult, you’re doing it wrong, and worse, that if the outcome is correct but instructions weren’t followed exactly, you’ll be punished.

How Do You Rate Yourself at Figuring Things Out?

You might look to certain areas of your life where you’ve unconsciously adopted the right attitudes and domain-specific tricks to be good at figuring things out, while in others you shy away from it. I’ve noticed, for instance, that I’m good at figuring things out for my business, but I’m much worse at figuring things out in order to save money shopping.

What would you rate yourself for this skill? What are areas you’d like to get better at figuring things out? What are areas where you feel held back by your environment because it punishes experimentation and innovation in solutions? Share your thoughts in the comments!