How to stop overthinking and make magic happen

Herbert Lui
Published in
5 min readNov 2, 2016


The line between thinking and overthinking is a thin one. It’s hard for anyone to discern where they are relative to it. Err on the side of action, and build momentum. Sometimes, you have to dumb it down.

There’s no shortage of sayings, like, “Done is better than perfect,” or, “No time like the present,” or, “The best time to plant a tree was 20 years ago. The second best time is now.” They’re all really getting at the same thing. Don’t think too much. Take action today.

Actor and politician Arnold Schwarzenegger writes in his autobiography Total Recall, “You can overthink anything. There are always negatives. The more you know, the less you tend to do something. If I had known everything about real estate, movies, and bodybuilding, I wouldn’t have gone into them.”

Similarly, Nasty Gal CEO Sophia Amoruso says, “I often say my naiveté early on in my career worked in my favor.”

More information doesn’t necessarily make for better outcomes or planning. Author Daniel Kahneman writes in Thinking Fast and Slow, “In other words, people who spend their time, and earn their living, studying a particular topic produce poorer predictions than dart-throwing monkeys who would have distributed their choices evenly over the options. Even in the region they knew best, experts were not significantly better than nonspecialists.”

Don’t let your brain get ahead of itself. Don’t consider everything that could go wrong or right. Just focus on learning what you don’t know, creating a couple of tentative plans and milestones, and taking action. You will learn and adapt as you go.

Here are three ways to defeat your inner overthinker while still using your brain just enough to succeed:

1. Ask questions

When you’re first starting anything, there’s pain in the form of friction. Some of this is in the form of information gaps. And while Googling is the simplest and easiest solution (and probably the most annoying thing I could tell you to do), a 15–30 minute conversation with another human being can be much more effective than Google.

When you’re talking to peers or experts, they can interpret what you’re wondering or asking much more effectively than Google and provide answers. They can also expose you to “unknown unknowns,” the things that you don’t even know you don’t know. After all, you can’t look for something you don’t know exists.

Apple founder Steve Jobs says, “I’ve never found anyone who’s said no or hung up the phone when I called — I just asked. And when people ask me, I try to be as responsive, to pay that debt of gratitude back. Most people never pick up the phone and call, most people never ask. And that’s what separates, sometimes, the people that do things from the people that just dream about them. You gotta act. And you’ve gotta be willing to fail, you gotta be ready to crash and burn, with people on the phone, with starting a company, with whatever. If you’re afraid of failing, you won’t get very far.”

Figure your actual question, and frame it properly. If you’re going to email a stranger about it, make it a pointed question that people can answer in 2–3 lines.

Author Ryan Holiday writes, “Sure, questions can be a sign that you don’t understand what’s going on. Which is why…if you don’t understand…you absolutely must ask. Before you start, before you say yes, before you try to convince yourself that hope is a strategy and you’ll figure out it out as you go.”

2. Break it down into steps

Author and The New Yorker staff writer John Seabrook talks about how he breaks 5,000 word articles into five 900 word segments. You can do the same with all sorts of problems — break your huge goals and visions into smaller milestones, and work towards those.

Sometimes, even within milestones, you can break those down into phases or weekly plans or metrics that you need to accomplish in order to make progress.

3. Think with your hands

My friends Humayun and Robleh blew my mind when they said, “Think with your hands.” I know I wrote it in the title as well. That’s because it perfectly articulates the idea. A lot of thinking isn’t necessarily done in the peace and quiet of a cabin, or in the meeting room with people. The best thinking can be carried out when the brain sees things and starts piecing them together, and this is done through taking action.

Star Wars creator George Lucas writes, “Don’t tell anyone, but when ‘Star Wars’ first came out, I didn’t know where it was going either. The trick is to pretend you’ve planned the whole thing out in advance. Throw in some father issues and references to other stories — let’s call them ‘homages’ — and you’ve got a series.”

When Kanye West announced his company Donda, digital and design studio OKFocus built a fake product and website for it. This publicity stunt could’ve totally gone wrong. Instead, OKFocus starts working with Kanye West and his friends just a few years (if not months) after the stunt.

It’s so hard to plan for that sort of thing. And they didn’t. OK Focus co-founder Ryder Ripps says, “We try to do one of these kind of projects a week just to keep our own spirits up and have fun. That’s the main objective, and prove to our future clients that we’re good at the Internet.”

Take action, and start things without knowing where they’re going to end up. Just fire, aim closer to the right direction, fire again, and so on. However, you must make sure to rise up from the action, to stop dumbing things down, at some point so you keep calibrating and making sure you’re moving in the direction you want to move in. The dots only get connected in hindsight.

Dumb it down

One day in the wild is worth a month in the lab. Catch yourself paralyzed by thought. Break the inertia by dumbing things down and taking action in spite of your hesitation. After all, of all things to do, one of the dumbest ones would be not to do anything.

Herbert Lui is the creative director at Wonder Shuttle and a former staff writer for Lifehacker. His writing has appeared at TIME, Fast Company, and The Globe and Mail. He writes a monthly newsletter where he shares books and quotes to make you happier, more creative, and more productive.

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Herbert Lui

Covering the psychology of creative work for content creators, professionals, hobbyists, and independents. Author of Creative Doing: