2016-07-25

I used to try to solve problems by just sitting there and running through the problems mentally, over and over. No pen at hand, cursor blinking. As it turns out, I wasted a lot of energy doing that. Instead, I could have been doodling, sketching, or diagramming my issues. I could have been re-evaluating them, re-thinking them, and coming at them from unlikely angles on paper.

I could have sketched out my problems in hundreds of scenarios. I could have written out my grocery list instead of trying to memorize it. I could have outlined that essay with a a mind map before spending twenty, even thirty hours of my life rewriting and reworking it. I could have made smarter, more memorable notes on paper when I was learning Swift.

I heard that writing stuff with a pen and paper helped you study better, remember more details, and think differently. I heard this a thousand times before I believed it. And when I started to believe it, in almost every case, the drawings, diagrams, and lists I’ve made have strengthened my ability to think about and deal with problems.

It has also helped me learn more quickly in situations where I really had to learn quickly—like my first site maps and content layouts.

The root of the problem

Since I work on computers anyway, it can be tempting type out my problems, diagram them in software like OmniGraffle, log them as GitHub issues, or just stare at an empty tab in Atom until I fall asleep. Sometimes, problems can be solved that way. I’ve solved many problems that way.

I’ve gotten plenty of work done thanks to GitHub issues. But, what if the scope of the problem doesn’t quite make sense yet? Or what if I think I know the root of the problem, but it’s a little vague?

I’ve really begun to like flowcharts and mind maps.



Excuse the lines, I don’t use a ruler. Sometimes I use grid paper though.

Often times my sad excuse for a brain starts off with a high-level project like “Site refactor.” Then, my brain expects me to figure out what the hell I’m talking about. As if I know.

Just copying down three more specific tasks down the ladder really loosens me up. After this point, I can start writing ten or twenty sub-tasks easily.

Reorder your brain mess and take out the trash

The root of the problem in this case is my inability to focus. To keep a train of thought. The older I get, the more I need references and touchstones. Without them, it can be difficult to step back and see the problems for what they really are.

I don’t have any mind mapping software, and I don’t plan to get any. Often times, I don’t even “finish” my mind maps—I just write down enough of an idea to get a grasp of what I ned to accomplish.

Einstein is quoted as saying, “If I had only one hour to save the world, I would spend fifty-five minutes defining the problem, and only five minutes finding the solution.” It’s fairly unlikely he ever said that, but whoever did say it was onto something.

Outline, plan, and then plan some more. Avoid the mental traps you set by not planning well enough. I force myself to write down this root of the problem and break it down into the smallest chunks that I possibly can.

Even thirty seconds in, I can break my “Site refactor” project into three sub-projects: user accounts, Stripe integration, and email automation. Even those could be huge projects — but I have already started to see how to focus my time, and where I should be focusing my energy.

I’ve developed my own way to prioritize tasks that seems like it’s based on the quadrant technique.



So, for this site refactor project, I’ve taken all of my miscellaneous tasks and prioritized them according to urgency: tasks for today, this week, before launch, and next release. Even these tasks can be broken up further… but I won’t bore you.

Chances are that I’ll be putting this into some Trello board or Wunderlist project sooner or later. But seriously, just getting it all onto paper at one time really solidifies it for me.

Force yourself to think like five other people

You might be looking at my process and thinking it’s not for you. And you may even try something like it and feel like it’s a waste of time. I didn’t think I would get anything out of making stupid quadrants, and I didn’t want to do it. But of all the weird things I’ve tried, it’s the one that really sticks.

There are tons of methods you could try. You should especially try the ones that seem like something you wouldn’t do. Get out your colored pencils, pull a Merlin Mann and grab some 5x7" index cards. Maybe even start your own Hipster PDA and never stop sketching.

Write your future self a letter. Order some AquaNotes. Roleplay as one of your customers. Leave yourself notes on the mirror. Sketch out your problems as difficult, hilarious doodles.

Here’s a really stupid one for the road:

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