Think Bigger, Ask Better (and More Absurd) Questions

Billionaire Peter Thiel (co-founder of PayPal) told CNBC in an interview that one of the things he wishes he could have told his younger self is that there is no need to wait. “I went to college. I went to law school. I worked in law and banking, though not for terribly long. But not until I started PayPal did I fully realize that you don’t have to wait to start something.”

His advice to us? Take your 10-year plan and ask one good (and absurd) question:

Why can’t I do this in six months?

These aren’t magic words. Even Thiel acknowledges that sometimes the ten-year arc is necessary and important, but that the importance is to have the meta-awareness to even ask the question. Sometimes asking that will reaffirm that it is time to put your shoulders down and push for the long haul. But sometimes asking why a 10-year plan can’t be done in six months dramatically reduces the amount of time it takes to complete that goal. Even if it isn’t exactly six months, reducing it to five years or even one is already half or ten times less than the initial goal that was set.

How to Accomplish More in Less Time:

  • Learn and apply the 10x Rule
  • Learn to ask better questions

The 10x Rule: Figure out what you want to achieve, examine how much effort and time you think it will take. Multiply that by 10. Get to work.

Lots of people have written books on this: Shane Snow, former Google Chairman Eric Schmidt, Walter Isaacson, even Peter Thiel. They all tackle, in various ways, thinking big. Some of them reference the 10x rule explicitly (Peter Thiel: “Once you’re 10x better, you escape competition.), some use different language to walk around the same notion. Thinking big, aiming for massive success is easier than aiming for incremental or safe improvements.

Former Google Director Astro Teller said in an interview that “It’s easier to make something 10x bigger than 10%”. That probably seems ludicrous, but Teller claims that the reason this counter-intuitive truth holds water is that aiming for 10x improvement causes you to “get to radically better solutions in honestly the same amount of time.”

There’s research to back these ideas up as well, Psychologists Edwin Locke and Gary Lantham published a number of works in the early 2000s that having easy or “achievable” goals reduces performance, while more lofty and difficult ones cause people to work harder towards achieving them. “Tight deadlines lead to a more rapid work pace . . . [and lead to] the arousal, discovery, and/or use of task-relevant knowledge and strategies.”

Now that we see how there are strong benefits to having lofty goals and aiming as high as possible, how do we do that? By asking better questions. And good questions are sometimes absurd ones. But before we cover that we need to be sure that our goals are lofty enough and clarified enough to motivate good question asking.

Lofty and Clarified Goals

A lofty goal is the sort of thing that you could easily describe as a dream. Plenty of people have dreams, but they’re all vague and filled with fantasy. A lofty goal that is clarified is something specific. A clarified goal has teeth to it, something real you can grab onto.

@Think bigger business goal“I want to be a good singer” for example, is not a great goal. Nor is “I want to become a successful business owner.” These are in the direction of a good goal but need to be made more specific, because so many things are relative in these two goals. A good singer according to who? What constitutes a good versus a bad singer, is it athletic ability, artistry, the number of people you’ve performed for? The same can be said of the business goal, plenty of people have moderately failing businesses or “hobby businesses” and don’t look for more to consider that successful. Having a storefront or an Etsy page is enough.

But if we take those ideas and clarify them into specific goals, they become far more powerful in motivating us to work hard towards them. “I want to win a Grammy for Best Male R&B Performance” is far more specific than “I want to be a good singer,” and helps find the context one needs to ask important questions in reaching that goal. “I want to make a million dollars in the next two years” is likewise a far better goal than “I want to become a successful business owner.” These goals are better because they also create success/fail conditions, there’s a measurable result that can be taken.

Once you’ve taken your goals and made them both lofty and clarified, you’re ready to ask good questions to figure out how to achieve them.

Asking Better Questions (asking absurd questions)

@Think bigger Wonderland mad hatterIf you found yourself standing at the tea table from Alice in Wonderland, if the Mad Hatter were tottering about and talking about un-birthdays and you see giant playing cards wielding medieval weapons of war, you might find yourself asking a bunch of questions that would sound ridiculous in any other context.

The real world is a lot more like Wonderland than you’ve been told it is. Everything about society is designed to tell us that the world is a massive predictable system, that success comes only through long slow labor for years and years and that the rules exist to protect us and there’s no better or faster way to create the life you want. But there often is, strange and unusual things are possible.

Consider this: A former WWE guest star and owner of a hotel chain is the President of the United States. Disney owns the rights to produce Marvel movies in which A-list celebrities jump at the chance to play characters like Ant-Man and Rocket the Racoon. The Cathedral of Notre Dame caught fire and a popular video game franchise offered up their research to aid in its repair, and there are maybe, probably, parallel universes.

Is your dream really all that strange in the face of these facts? People who are able to achieve massive success do so because they are willing to ask questions that other people will call absurd. But we, like Neo in the Matrix, have learned that the system, the “way things are,” is not how it has to be.

What areas in your field have assumptions in them? Why do they exist? Is there a real reason that the assumption is in place, or does it prevent innovation or progress? Shane Snow says that “Genius has less to do with the size of your mind than how open it is.” Are there connections that could be made that don’t exist now because people assume they can’t be?

When do you have to “pay your dues?” Is that true? Sometimes paying your dues is about developing a skillset or a needed body of knowledge to enable success, but often when people say you need to “pay your dues” they’re inducting you into a system that feeds the people who benefit from its existence without actually improving your life in any way at all. We’ve been trained by society to think that there are rules we have to follow and things we have to do in order to climb the ladder of success: but sometimes there isn’t really a ladder at all. Sometimes the series of steps needed to become X is made artificially difficult (imagine a pit that you get pushed into and then they give you a ladder to climb out).

What timelines exist? Why do they exist? Can they be cut in ½ or ¼? Examine how long something is said to take in whatever field you work in, why is it that it takes that long? What would have to exist in order to make it happen twice as fast? This is how you find innovations in any area of life, look at the way things are currently expected to be, how long they’re supposed to take and ask why not faster?

@Think bigger massive action big leapWhat obstacles stand in the way of success? Who or what put them there and why? How can these be lept over, even at great cost? The difference between people who succeed and people who don’t is that successful people are willing to do what it takes to get the job done. They’re willing to accept the high cost, the inconvenience, the difficulty, to reach their goal. They take massive action to remove the obstacles that stand in their way.

Believe it can be done

Focusing on trying to set “realistic goals” puts limits on what is possible. The mechanisms of society and psychology are designed to make safety a priority over possible success. This is why so many people underachieve their entire lives, they are afraid of trying to do something that seems impossible.

@Think bigger self belief think bigIn his book The Magic of Thinking Big by David D. Schwartz, he outlines why this is true. “Believe it can be done. When you believe something can be done, your mind will find the ways to do it. Believing a solution paves the way to a solution.”

The example he uses is of a class. First, the class is asked to debate the Pros and Cons of abolishing the American prison system. The class immediately erupted into arguments about whether or not it was possible or moral. But then there was a shift when he changed the question.

Nina Semczuk outlines how it plays out: “He had his students think of all the ways to end the prison system within a certain number of years. Within minutes, the class turned from nitpicking all the downsides to closing prisons, to thinking up creative, innovative solutions. The hardest part of the exercise, Schwartz writes, was calming his students down to end the thought experiment as people fed off each other’s creative energy of solving a hard problem.”

It is possible to overcome the biological/societal bias towards safety and think creatively about the problems humanity faces, but it requires creativity. And that creativity is easy to unlock if one learns to ask absurd questions and operate from an assumption that the seemingly impossible is in fact completely possible.

Another point from The Magic of Thinking Big relates to this: you are better than you think you are. A lifetime of societal conditioning and countless external voices are constantly saying “there’s someone better,” but the reality is that we are often far more competent, far more intelligent, far more capable than we believe. Schwartz suggests making an exercise of thinking of yourself as 5 times better than you currently do. If you were five times more intelligent than you are right now, what would you try to do? If you were five times as good at your job as you think, what might you be doing differently? Then do it.

This is important when setting impossible goals and asking absurd questions because it helps to grasp how the “impossible” really isn’t. If the goal is to make twice the amount of money per year as you do right now by next year, that doesn’t seem like such a lofty goal if you’re 5 times as capable as you think you are. You’ve barely used any of your true capacity because you’ve been playing it safe and living up to shallow expectations you’ve placed on yourself.

@Think bigger ExcusesMaking excuses, according to Schwartz, is another pitfall in trying to think big. Things like “I’m too old, I’m not intelligent enough, I don’t have the qualifications, etc.” act as mental blockers which set a cap on achievement and make the kind of creative exploration needed for exponential success completely impossible. If you are truly 5 times better than you think, these “problems” are just excuses made up in order to avoid the possibility of failure. Failure is nothing to be afraid of, stagnation is.

Thinking bigger isn’t merely goal setting and large-picture stuff, thinking bigger is about self-talk and self-idealization just as much as it is about the things you’d put on a vision board. Set a lofty, absurd goal, recognize that you are 5 times more capable to achieve it than you initially think, and let go of the excuses holding you back from making the smart moves and creative solutions to reach it.


How do I set better goals?

This is a great question, as setting better goals helps us think bigger and ask more absurd questions; setting better goals is important if you want to start asking more of yourself and start living beyond the excuses and small thinking that currently holds you back.

There are a hundred different resources on this, and it is one of those things where what works for me might not be particularly helpful for you, so you might have to try a couple of tools and tricks and see what works.

A great system for it, however, is outlined here. Basically, the idea is that you set goals with these five points in mind:


Having a clear goal with measurable results of success or failure


A goal should have a component of difficulty, of doing something that you haven’t done before and will need to work hard to achieve


This is different if you’re working in a team environment or working on your own on something; in a team, people are likely to commit to a goal they think is achievable, especially if the leader is someone they consider to be trustworthy.

Individually the commitment is on you, so I’d suggest involving other people in a more accountability-focused way. If you want to write a book by the end of this year, ask some of your friends/family to check in with you in your monthly or weekly writing goals as a way of motivating you to reach or exceed them. Speaking of which:


Again this depends on if your goal involves yourself or a team. In a team setting, you can get feedback from your team members as well as outside parties about how things are progressing and where there might be obstacles in the way of success. As the leader, it is your job to remove those obstacles or find a way around them.

Individually this is that accountability piece I mentioned in the previous point. Consider how quickly other people are working on similar size projects, are you faster or slower than them? If you’re slower, why is that? Asking other people who’ve worked on something similar you can often gain insights and avoid pitfalls in your own work.


Goals should be challenging but achievable. As complexity increases, the time allotted to complete a goal should increase. This is especially important if you’re working in a team environment, putting too much pressure on your team by asking them to accomplish a complex task in too little time will cause frustration and burn out.

Working on your own on a project means that the only person you can stress out by putting too much pressure on is yourself, so be sure that you’ve structured your goals and timelines in a way that makes you excited and motivates you to keep working, without adding too much stress or anxiety about not having enough time.

How in the world could I possibly be 5 times better than I think I am?

You’d be amazed at what you’re capable of. Ask someone you’re close to what things they’re most amazed by about you. You’ll probably be surprised at their answers, and the things they describe as being impressive might feel like nothing to you. Like it was as easy as breathing.

Often times the things we are best at, feel like they aren’t skills because they are easy for us. In the words of Jeff Winger: “You are all better than you think you are, you are just designed not to believe it when you hear it from yourself.”

Just accept that you have this blind spot about yourself, that you’re far more capable than you think you are because the way our world is set up is meant to make us feel like we’re less than we are.

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