Forget Thinking Outside the Box, Thinking Is the Box: An Interview With Tom Asacker

Like George Lucas said: “We are all living in cages with the door wide open.”

Uncertainty is the norm, so you better learn how to deal.
Uncertainty is the norm, so you better learn how to deal. Pixabay

I am a huge fan of Seth Godin. It’s hard for me to imagine another thinker able to reduce so much of modern life’s excuses to a reasoned clarity. He has that way of illuminating what we all know deep in our bones, but for whatever reason we can’t say it.

And so when Godin offers a perspective on another modern day philosopher, I pay attention. One of those authors Godin has heaped praise on is Tom Asacker—the author of “I am Keats” and “The Business of Belief.”

Tom does not beat around the bush: “What if everything we thought we knew is wrong? What if our basic reality—what we know to be true about how to think and live—isn’t all it’s cracked up to be?”

That is a frightening proposition for just about everyone.

When first bringing people into his “we have looked at this all wrong” world, Tom often quotes Tom Stoppard’s character Valentine from the award-winning play Arcadia:

“The future is disorder. A door like this has cracked open five or six times since we got up on our hind legs. It is the best possible time to be alive, when almost everything you thought you knew is wrong.”


We have all gone the wrong direction when it comes to the stories we tell ourselves. The goals we fixate on instead of the right process are literally killing us. And our innate human desire to control, well, there is no such control. Uncertainty is the norm, so you better learn how to deal.

In 2012 I started a trading podcast. About six months in I decided I wanted to go beyond my quant-trading niche alone. There was no logic or rationale, just a feeling. George Lucas said it: “We are all living in cages with the door wide open.”

I did not know at the time the door was wide open. Lucas’ confident perspective was not driving my new podcast direction. But if I did not walk through that wide open door I would not be so fortunate to share my most recent interview with Tom Asacker.

Michael: I need to relay a story for my first question Tom. Many don’t know that every holiday season the Sci-Fi Channel runs a Twilight Zone marathon and one of my favorite episodes went off this year. The great character actor Roddy McDowall was on. He and another astronaut were preparing to go to Mars for the first time. McDowall was nervous and not so adventurous. His associate was optimistic, and very “Let’s go do this thing.”

They leave on the flight to Mars, and crash-land.  His associate dies because McDowall was too nervous to open the door for help [from the Martians].

The door finally opens and there’s people who look like humans. Roddy McDowall has his gun in his hand ready to shoot and then he all of a sudden feels happy that he doesn’t have to shoot because they’re nice to him.  They take him to a house and he’s thinks, “Oh, my gosh!” It’s a complete 1960 style house. He’s so happy, he’s so excited.  It’s just like he expected.  He feels comfortable and secure.

The Martians say, “Hold on for a second. We’ll be back in a little while,” and they leave him alone.  He starts realizing there’s no windows, there’s no doors, there’s nothing. He realizes he’s locked in. Finally the window opens and there’s bars. Everyone’s looking in at him. He looks down and sees a sign that says, “Earthman in Natural Habitat.” He was put into a zoo. A physical zoo and in a physical cage. But I wonder if he would not have held the gun out, if he would not have shown these people, these Martians, that he was scared and the typical character of what they might expect from earthmen, if he would have shown something different then maybe he wouldn’t have been in locked in this cage…Frankly he ended up in the physical cage, but he was already in a mental cage to start with.  

I was thinking about that [episode] while going through your work and I want to quote from you now, “We’re confined to mental prisons of our own creation and the locks to those cells are the stories we tell ourselves.  Stories that are make-believe.  We make them up or others make them up for us and eventually we come to believe them. We call those inherited and learned accounts of life reality.”

Am I off base?

Tom Asacker
Tom Asacker

Tom Asacker:  I’ve seen that episode but I never thought of it that way. Did his belief and how he came across to the Martians end him up in that cage? There’s your metaphor right there. That our beliefs are the things that cage us. The people that wrote these shows, Rod Serling, the rest of these guys, they had wonderful imaginations and they were trying to get across messages with these old Sci-Fi shows, so that may have been one of the messages.

Michael: Circling back to your newest work, the idea of a cell, a mental cell, how did you realize you were in one?

Tom: I felt I couldn’t make a decision. The interesting thing is, is that’s what I study and that’s what I teach, how to make decisions, how people make decisions. My last book, which was about belief. I talked about how beliefs are formed. I didn’t even realize it until I got into this, is that you can’t think your way out of a cell because beliefs are driven by a desire. You have to have a feeling that will pull you out of your conditioned mindset, the cell that you live in. And it’s that feeling, that desire, that intuition, that instinct of if you follow it, it will get you out. But thinking about it just keeps you in.  Most say, “Think out of the box,” and I say, “Thinking is the box.” The conditioned way we approach the world is we think we know everything. We think this way only based on our experiences which are limited, so how can we possibly know everything? We have to stop this incessant thinking. When we get this feeling that drives us, we have to somehow be able to shut off all of that knowledge and move our way into this future and out of that cell which is thinking.

Michael: In 1996 I felt like I had to put up a website, period.  There wasn’t any economics that supported it, there wasn’t anything that said, “I must do this, this is going to make money, this is going to make me happy …”

Tom: [Ha] You didn’t run a business model?

Michael: No, I had to put the website up. It felt like something was happening and that I had to do it.  Now roll forward six or seven years after that, and some nice success online, I felt like I had to do a book. I didn’t have any kind of economic plan. A few years after that I looked around, I thought, “Well, other people are making these documentary films, Michael Moore etc.” I felt why not me? Roll forward a couple more years and I’m traveling throughout Asia and say to myself, “I just feel like I need to stay here. I don’t need to go back to San Diego.”  

None of this was a well thought out plan. It was falling off a ledge, and I felt comfortable falling off the ledge, but [as] I look back, those are four key things in my life that fit right into where you’re trying to get the audience to go.

Tom: Yeah, and interestingly you bumped into favorable circumstances once you jumped off that cliff. That’s the interesting thing. The metaphor I use with belief is crossing a bridge. The metaphor that I use with this process, which is not belief because you don’t really have this perfect vision of what the future is and you don’t have the stable bridge to walk across this chasm, you’re taking a leap of faith because something feels right to you. I don’t know who said it, Ray Bradbury maybe, he said, “Build your wings on the way down.” Start your website, figure it out as you go. Write your book, you’ll figure out how to do it.

We’re becoming slaves now to data and to the rational thinking process. It’s talking a lot of us out of doing things we should really be doing to change our own lives and to change the world, to change other people’s lives.

Michael: When I started, I had no ability to code or write.

Tom: There you go.

Michael: Once I made the decision to leap, I then felt, “I have to do this.  I have to figure it out. I can’t go back now. I don’t want to go back now. Going back is giving up. You’re just not trying. If some other smart person can do it, why not me?”

Tom: We have this thinking, this narrative thinking that we have a story and our past determines who we are today. We want to keep the story coherent and make sure what we’re doing makes sense. This is pretty much subconscious. We think of doing something and then say, “Well wait a minute, that’s not me,” and it’s really funny because who’s you? I mean why can’t you? Why can’t you just stop everything you’re doing and do something else if you want? Or don’t stop what you’re doing but do something way out of the box just because you feel like it. Who says you can’t?  

But we have been conditioned…This idea that we’re stories, that we’re characters in a story that does this to us and prevents us from realizing, “No, no, we’re dynamic. We’re not static characters, we can do anything we want to do.”

Michael: Peter Thiel, the entrepreneur, was talking about people in the Washington DC area. I grew up in that area so I know it well. He said this is the one area where they value input more than output and if you go to a meeting in DC, it’s a 15-minute monologue describing your CV back to 7th grade. Look, plenty of high IQ people in that area making a lot of money, but they don’t seem to understand that the script was given to them. That script doesn’t exist, it’s not real, there’s no such thing but they truly believe they have to follow that script, or what? They’re going to die? Oh by the way, we all die.

Tom: That’s how powerful this is. This illusion that we have this identity, this manufactured identity that’s part of the world—that’s what drives us to really emphasize this idea of: We can think our way through everything and we are characters in stories. It makes us become static. Like this whole idea of what a brand is. People would say things like, stick to your knitting if you’re a brand.

Michael: What does that even mean?

Tom: Yeah, they would use that kind of terminology or they would tell you that your identity is destiny. I would listen to this and say, “Wow, how confining is that?” When you have the resources and the intellect and the money to do anything to serve the market place, why would you want to live in this story that says, “This is who we are?” Who you are is what you create not what you did in the past, but people get stuck in that. Organizations in a big, big way get stuck in that.

Michael: I love this line from your newest work. “When you’re stuck between a rock and hard place you must use the rock to break through the hard place. You have to use your mind to escape your mind and free yourself.” That’s tough because many don’t even know they’re in the middle of that hard place do they?

Tom: I try to tell people I’m working with on these concepts: “Do not try to wake someone up that wants to stay asleep,” and that’s the problem with a lot of people. When you tell them, “You’re living a role, you’re not really conscious,” they take it personally because they don’t want to wake up. But if you get to people waking up, that are feeling uncomfortable, that are saying, “There has to be more than this. Why am I still doing this? There has to be a better way,” then you can approach them and say, “Okay, let’s start having you listen to what your mind is telling you and let’s understand why it’s telling you that. Then you’ll see there is not a reality behind that, it’s all invented by other people and by you.”

Michael: Why do you think they take it personally? Is it because they’re confronted for the first time where somebody sees through them?  

Tom: No, I think it’s an affront to their identity. Anyone that’s living some type of story, they take their story personally. They believe they are that identity, whoever it is, because that’s the self they project to the world. See, they believe the drama of the world is the place that’s going to get them everything they need to be fulfilled in life. They don’t realize their essence, their true self, their authentic self, this dynamic essence that says “I can do anything I want to do, I can try anything I want to try, that’s the source of a fulfilling, exciting, meaningful life.” They don’t think [like] that.

Michael: But when you give people a reason, they’ll jump. Everyone’s just playing it safe?

Tom: You’re exactly right. I discovered a lot of the parallels between people living in stories while I was writing a screenplay. I started researching all of the concepts that go into the screenplay, and there’s this one particular concept that is critical, the inciting incident. They take the protagonist in a particular story and really early on in the story, in the movie, there’s an inciting incident that forces the protagonist to go on some type of journey; to discover themselves, to change and grow. [For example,] the tornado takes Dorothy away. She’s not going to go to Oz unless the tornado takes her.

In life a lot of people have to wait for an inciting incident like a heart attack, a divorce, being fired from their job, or whatever it happens to be in order to break free of the story and go on an exciting adventure and change their life, but guess what? They don’t have to do that. They don’t have to wait for an inciting incident because they are in charge of making the decisions of how their life’s going to unfold. They can do it whenever they want to do it. Why do we wait?

Michael: If you can’t find that inciting incident inside yourself and you need to have these external forces drive you, it’s probably not going to illicit the change you might imagine will it?

Tom: No, but the interesting thing is there could be some type of serendipitous encounter by traveling there.

Michael: That’s one of my favorite words of all-time, serendipity. What’s serendipity to you?

Tom: It’s just a lucky happenstance. [For example] I gave a talk at a conference and I did it for free because I liked the city and I wasn’t busy. I bumped into somebody and developed a relationship. That was serendipity. That would not have happened had I not gone out there. I didn’t make it happen, this other person didn’t make it happen, you put these things together and something happens. And so the issue is how many things are you putting together? How many opportunities are you giving yourself to bump into things and to make things happen? If any entrepreneur would be honest with people they would tell you, “Look, I lucked out. I had a meeting with X, Y and Z I never expected to [have]. I was introduced to him by such and such and if that didn’t happen—nothing would have happened.

What we do is we go back in time and recreate history in order to create a story that sounds good. Then we tell that story and unfortunately by doing that, we make other people think there’s this special secret sauce you have to have in order to be successful, when in fact it’s not that at all. You have to have an idea, an idea that serves people. You have to be passionate about it and then put yourself out there and be fortunate enough to bump into the circumstances and people that’ll bring that thing to life. That’s how it always happens.

Michael: Let’s talk about that bumping into. [Most] don’t experience that serendipity where something fabulous happens because they go one direction and don’t cross paths with other directions, and [serendipity] never would have happened if no leap to begin with.

I’m still amazed after the 1995 Netscape IPO [with all of that entrepreneurial opportunity that followed], and if I flip on any news channel today I have politicians parroting back promises about jobs, jobs, jobs. Literally what is being promised is that the system is going to keep them in their prison they are not allowed to escape. Is that how you see it?

Tom: That’s the story right, and in order to keep people calm you have to tell them a story they can buy into. Beliefs are a calming thing. That’s why people have beliefs because as soon as they believe something they can stop thinking. They don’t have to worry anymore. People say, “Oh okay fine, I’m going to have a job forever, I don’t have to think about this.” That’s why you shouldn’t really believe anything. If you want to hold this thing in your mind for a while, that’s fine, but you’d better accept the other side of it as well. Hold it in your mind and deal with that tension because there is nothing you should believe in like, “It’s never going to change.” Everything is going to change.

Michael: It’s more about having a good life process as opposed to imaging that you can predict tomorrow?

Tom: Exactly. You want to take a movie [for example], take Rocky.  Rocky liked to box. He may have never got the shot with Apollo Creed, that wasn’t the point. Rocky was a fighter, that was what was in him and he enjoyed doing it. You want a real story? Take The Band. The Band loved to play music. The Band didn’t have to bump into Bob Dylan and Bob Dylan didn’t have to say to these guys, “Hey, you guys are great, do you want to go out on tour together?” That was their serendipitous encounter but it didn’t matter, they loved playing music together.

That’s the key, to realize the process is the goal, not some place in the future. When you get to that place in the future it’s never the thing that you’re looking for anyway. You always look and say, “Wow, I really enjoyed what we were doing before we got there.”

Michael: As you say, “Life happens in each moment.”  

Tom: Exactly, and that sounds Daoist doesn’t it? But it’s absolutely the truth. What we’re doing right now, having this conversation, I’m enjoying it and that’s why I wanted to do this with you, because it’s fun. It’s enjoyable. It’s meaningful. Don’t do it if you’re not enjoying it and putting everything into it.

Michael: Let me quote you, “People in general already believe that they’re better and smarter than average. It’s a cognitive bias called illusory superiority and the Internet is making this bias even more extreme. It’s supercharging people’s preconceptions and solidifying their false assumptions.”

I see this across Facebook. I love to start debate and perhaps argue on my Facebook, not ad hominem but if I see an inconsistency or if I see hypocrisy in whatever, I like to comment on it and it’s often in charged areas where there’s deep emotion. It still amazes me the number of people if faced with an obvious inconsistency or hypocrisy, and if they had to imagine themselves being in a courtroom with jury instructions…people are losing the ability to look at details and make sound decisions. They are so burdened by the story inside their head or whatever [it is] they have to protect aren’t they?

Tom: The ability to hold these conflicting opinions in your mind without searching for certainty, without grasping for an answer, that’s the thing people can’t do. Their identities are tied to these beliefs and when you say something that questions their belief, they feel that their identity has been threatened.

Michael: It’s a war.

Tom: Right. And that’s why beliefs are bad because beliefs are polarizing. If you believe this and I believe this, well then we’re done.

Michael: If people look at the last year [2016] in America on political debates, whether you were on the left or the right, cognitive dissidence should have been and should be historically the only thing [examined]. The political summation of 2016 election should start with, “This election was about cognitive dissidence.” That’s the historical artifact for the United States of America. On both sides it was overwhelming. Elaborate here Tom.

Tom: I can tell you that that whole process was driven by people’s identities.It wasn’t rational. A computer couldn’t have come up with [the outcome] because a computer would have punched in criteria, hit a button and said, “Okay which one gives us the best?” It didn’t work like that because people were voting based on what they wanted to see happen based on what their feelings and their desires were. And I’m going to tell you primarily that that was driven by identity.

Michael: Let’s talk certainty. People crave it. They want it. I look at my world of investing books, and people want to know what will happen tomorrow. They want to know that this person can predict or tell them with assurance [that] this will be it. When you get behind the scenes and talk to the highest-level achievers and the highest level thinkers, they exist perpetually only in uncertainty and are extremely comfortable in uncertainty. [They] don’t wake up each day worried they don’t know everything. They have a plan, they have a process for dealing with the next unexpected and there’s always going to be another unexpected. The vast majority of any population imagines certainty is achievable don’t they?

Tom: Exactly. And that’s one of the three components that drive people to make particular decisions in whatever it is. Brands, consultants, software. They are looking for [a] sense of control because they don’t want the future to be something that’s nebulous. They want to believe the bridge they’re crossing is safe and it’s going to get them to the place they want to go. Anyone who paints a picture giving that assurance, they win.

Now unfortunately, they’re not telling people, “Look this is a gamble, this is a bet.” They like the feeling of certainty, but it’s not certainty and it’s not control, it’s the feeling of certainty and control, right? Everyone wants something in the future. They don’t want something today, because today they already have what they have today.

Michael: When I’m thinking about narratives, I think back to my first book and I wasn’t thinking in a linear fashion. When that first book had some success I got a major publisher for my second book. I remember the new publisher getting it, they had paid a lot of money for an advance, and they said, “What is this?”  The publisher said, “We need a narrative. It has to be a narrative. It has to be a straight line.” Speak to stories, Tom.   

Tom: All these big brands I talk to and I work with, they love to tell founder stories. But they’re nothing like their founder stories because the people who founded these companies, they were out there trying to create a movement. They didn’t have a plan. They made stuff, threw it in the back of a buggy and went around showing it to people. But ask some of these big companies to do that today, to take a risk. They’ll come back and say, “No, no, we have a process of if you can’t show that it’s going to make $50 million in the first year, we don’t even consider it.”

Michael: You’re getting at hedging bets. Not many, when you go back and look at the beginning of their stories, were hedging their bets, they were jumping off. In fact, someone sent me a book the other day and said, “you might want to check this book out,” kind of like saying, “maybe this would be a nice guest for your show.” The book was essentially saying how to not change anything in your life, keep everything the same but become an entrepreneur with 10% of your time.

And I thought, “What kind of crazy convoluted, contorted person do you have to be to try and believe that to begin with and then to try and execute it is impossible.” How the hell do you compete with Steve Jobs if you’re going to stay in your office cube all day long and pretend that you’re competing with somebody who is living and breathing this, whatever their passion is, 24/7. You’re going to do it part-time and maybe half-way lift a finger?  It doesn’t work that way does it?

Tom: You’re right. I was actually talking to somebody today about Apple and how they’re not hitting their numbers. We were discussing how they’re going to go into original TV programming and movies. I said, “It’s so interesting, when Jobs was running it, he had a feeling for something that people would want.” I said, “Now Apple is looking at the marketplace saying, what do they want? We’ll give that to them.” And it’s completely different. It’s not arising from your imagination, from this uncertain idea, this gut feeling that you have, it’s coming from data and you can’t create from data. You create from the soul, you create from your inside, not from the outside.

Michael: It’s an interesting choice that Apple made. You go from the visionary, Steve Jobs, and then he probably single-handedly implemented an accountant to be the CEO. Whereas on the backbench [there is] a guy like Jonathan Ive, their designer [who maybe] didn’t want to do it, but when I watch a video of Jonathan Ive talking about his creations, I’m inspired. I just want to listen to him all day.

When Tim Cook starts talking I turn the TV off. We don’t know all the reasons for this, but to keep their influential and inspirational minds not at the forefront and to leave just another suit at the head of the company…

Tom: That is a perfect metaphor right there. I’m not saying that thinkers, engineers and data guys are not necessary, but don’t let them lead.

Michael: This doesn’t necessarily mean you are proposing you go off into the desert and walk for 50 years, and not take on any life battles. You are looking for people to find balance. It may not necessarily be someone’s calling to go to a monastery in Tibet, however, that could absolutely be the calling?

Tom: Oh absolutely. I think sometimes people read this and they think I have a problem with the rational thinking process, and that is the furthest thing from the truth. What I have a problem with is that particular mind set interfering with creative process.  Keep it out. Use that when you want to introduce what you’re doing to the world. [But] when you’re designing a bridge, keep the engineers out of there until you’re ready to sit down and say, “Here’s my design, how do we build it?” Then bring them in.

Michael Covel is the author of five books: including the international bestseller, Trend Following, and his investigative narrative, The Complete TurtleTrader. Michael is also the voice behind Trend Following Radio, the underground alternative hit that has been as high as No. 2 on iTunes with 5 million listens. Forget Thinking Outside the Box, Thinking Is the Box: An Interview With Tom Asacker