Tim Ferriss: Ask Absurd Questions and Stop Fetishizing Failure | Big Think

So in Silicon Valley, there's the fail fast, fail forward, the fetishizing of failure, and it's become very trendy. I think it's extremely misleading and misinterpreted and misapplied in many cases. So whether you ask, say, Peter Thiel, who views failure as always being a tragedy; there is no exception. It is not some aesthetic imperative or learning imperative necessarily.

Or you talk to, say, Mark Andreessen, for instance, who I interviewed for the Tim Ferriss Show, but also for Tools of Titans, and he says, when I was getting started, I'm paraphrasing here, but when I was getting started we didn't have a fancy word for it, we just called it a fuck-up. We didn't call it a pivot. I think that it would be better to say iterate fast and iterate forward. So there's no problem with getting, say, feedback on a minimally viable product or an earlier version of a product.

So Reid Hoffman, another person I've interviewed, founder/cofounder of LinkedIn and the Oracle of Silicon Valley, as he's referred to, even by a lot of the elite investors, for instance, in Silicon Valley, believes that you should effectively, if you're not embarrassed by the first version of your product that you ship, you're too late. And it's true, I think, in software development and different types of user interfaces and so on, but it's not always true for, say, a book or other types of creative endeavors.

So it's a case of being very specific in what you mean by failure and also making sure that what you're transplanting from one area to another, if you are doing that, actually applies in your industry, in your trade, in your craft. But I certainly feel like doing your homework, coming out, and maybe the Silicon Valley ethos should start looking to the military more, to say, I think it's David Hackworth, I think I'm getting that right, who said if you find yourself in a fair fight, you didn't prepare properly or something along those lines.

I mean, it is entirely plausible and possible to come out and just smash your competition from the second one of round one. And I think even if you do end up failing and then correcting course, that's a good aspiration to have—not to come out really shoddy and handicapped from the get-go, expecting to pivot 27 times.

Then if you look at my portfolio, for instance, I have about 70 companies I've invested in; I was a pre-seed advisor to Uber. And Uber's business model hasn't really changed. It's been the same for a very long time. If you look at Derek Sivers, the founder of CD Baby, he came up with the business model in about five minutes of going to a used record store and asking them how they did it. It remained the same, effectively, for ten years, 15 years, until he sold it for whatever it was, $24 million.

So you don't have to fail; it's not a prerequisite for having a successful company or a successful life. You just have to learn. So I think learning and iterating are two words that are going to be more valuable than failure. But when failure does slap you in the face, when fortune serves you up a tidal wave of some type or quicksand, being able to adapt to that and not emotionally overreact, I think, is certainly important. But you shouldn't be striving for failure.

If you look across all of the icons, titans, world-class performers that I've interviewed in the, say, wealthy section, if we're dividing them into healthy, wealthy, and wise, when you look at the business side of things, one of the most common patterns that you spot is absurd questions. And the power of the absurd question is really something that I've paid a lot of attention to in the last few years.

Whether that's, say, Peter Thiel, a serial billionaire, certainly an incredible entrepreneur, but also an incredible investor, good at betting on presidents, it turns out, as well. And he would ask questions such as, “Why can't you accomplish your ten-year plan in the next six months?” And if you talk to, say, Peter Diamandis, Chairman of the XPRIZE, he might ask the founders of companies he's looking at as potential investments, “If you had to 10 X the economics of your startup in the next”—fill in the period of time—“six months, three months, how would you do it?”

And if they say it can't be done, that's not something we can do, it's impossible, his response is, “I don't accept that answer. Try again.” Those types of questions, I think, whether it's 10 X thinking, 100 X, however you frame that, it could also be a constraint. For instance, if you had to accomplish all of your work or grow your company two X while working two hours a week, if you had a gun against your head, how would you attempt to do that?

These types of absurd questions don't allow you to use your default frameworks for solutions. They don't allow you to use your base of current assumptions to come up with answers. It forces you to think laterally. It forces you to break some of the boundaries on the sphere of comfort that you've created for yourself. And that is what makes them, I think, in a way so powerful.

And these are not questions, by the way, that I think are valuable if you ponder them for ten seconds and go, “Hum, yeah, maybe I would do this,” and then move on with your day. I think that journaling, as an adjunct to asking these questions, is very, very important. So I will sit down very often in the morning; one of my rituals, also borrowed from a lot of these people, is morning journaling of some type.

And I tend to use either morning pages, five-minute journal, or just a separate type of freehand sort of goal dissection. And this would be a case where I would ask one of those questions, and I would write freehand for, say, three pages, three to five pages, and drink some tea as I'm doing it. And that is when you will not only come up with interesting ideas, and they might be 90 percent garbage, but if you have ten percent that lead you in an interesting direction that could completely revolutionize your business or your life if you take that seed and do something with it.

And that's been the case for me for a very long time. I actually created a list at one point after observing this pattern among these people I was interviewing, and I just made a list of what are the most absurd things I could do right now related to my life and business? And I created this long list. And some of them were terrible. I mean, literally, I was at a conference; I was bored, and that's why I was doing this. And some of them were very specific business-related; one of them was, “Cut off my own feet.” Like, what the hell? So I disregarded that one. I still have my feet. You can't see, but they're intact.

And at the same time, though, one of them was take a complete break from the startup investing—so retire from startup investing—because that had become a source of stress due to the inbound, the deal flow. And that was a real game changer for me, taking my indefinite startup vacation about two years ago, which has led to incredible growth in other areas, including in my own businesses.

So there you have it, the power of absurd questions.