Fail More

When Caesar crossed the Rubicon there was no turning back. It was the assault on Rome that turned that Republic into an empire. When people come and interview with me or I talk with groups across the nation I don't want people to just try, I want them to burn their boats, cross the Rubicon – mixing metaphors! – and really go all-in on commitment, not just try.

So for me "try" is a weaker word, it's a word that implies, "Yeah, if it's not good I'm going to pull back." I want ultimate commitment and I want you to go forward. And if it means failure, so be it, learn from it.

Let's be realistic, it's very difficult to embrace or get your arms around the word. You know, "failure" has that connotation, maybe that visceral feel, that it's uneasy – but the people I've spoken with (the greats, the ones that really make it) embrace failure as the way forward. For them, it's the indispensable teacher on their way to success.​​

Rachel Salaman: Well, part of this is another early message from your book, which is that inside every success there are remnants of failure, and in every failure there are pockets of success. Now that's quite a nuanced idea, could you tell us a bit more about that?

Bill Wooditch: I can't tell you how many times I've dodged failure and I can't tell you how many times I've probably avoided success, in whatever I'm undertaking. So as I'm going and I'm moving forward I'm trying to make an assessment of, "Am I on target, am I reaching my goal or am I further from it by what I'm doing?"

So I'm looking inside and I'm saying, "What do we do on this deal?" or "What do we do on this opportunity to make it a success?" And we'll analyze that dispassionately, "We did this, we did this, we did this." The same with failure; we'll look at something – and I think it's a good tool for your listeners – we'll look and say, "What did we do and how can we prevent this from happening in the future?" [then] share it company-wide so we have touch points and we have key points to look at, that can guide us and maybe we can avoid a failure.

So inside of each success there is a pocket of failure we need to pull out and say, "Good, we dodged this, we did this right." The same with failure – there are pockets of success and [we] say, "Man, we got so close on this, we just took the wrong road."

Rachel Salaman: Yes, and I think that helps diminish the stigma or embarrassment around failure, doesn't it, because if you stop seeing it as failure, as absolute, that it's actually something that has success within it, then you kind of feel a bit better about it, don't you?

Bill Wooditch: Yeah. You know, it's interesting that ​on Elon Musk considers a 90 percent failure rate to be good, and he'll say, "I'll take it and, you know, even if I fail 100 percent, 100 percent of the time, then people can take my mistakes and make something from them to improve in the future."

And that is the mindset – mindset is so crucial – that is the mindset I have, that even if it crashes and burns then people can pick up some of the remnants and piece together their own success. So I embrace failure as that way forward, you know. Failure and success are two sides of the same coin to me.

Rachel Salaman: So to what extent should we be talking about ambition in this context? Isn't that sometimes the driving force of learning from failure, rather than the failure itself?

Bill Wooditch: You know, ambition is a great word. It can be blind, and I think you take the blinders off when you understand that ambition is required, but ambition without knowledge, the knowledge that failure provides, is truly a waste of energy.

And it can be misdirected: there are a lot of ambitious people who aren't successful. A ton of people who have a lot of activity, their activity is not directed toward or measured toward what is their goal, what is their real goal. So I think ambition is something that's absolutely a requisite condition, but you have to have a dispassionate way to look logically, "Am I moving forward and is my ambition channeled in a place, in an environment, in a job – or am I creating an opportunity and career that's best suited for me?"

Rachel Salaman: And what about luck, because I noticed that most of the success stories in your book owe as much to luck as they do to learning from failure?

Bill Wooditch: Seneca said, "Luck is what happens when preparation meets opportunity," and we say that luck is the residue of design, that we design our own luck. So we can look upon fortune and say the heavens have smiled upon us, or we can take personal responsibility, get in play, and design our own luck by moving forward. And we cannot do it if we feel that fear from fear and we're stymied by it.

Rachel Salaman: Well you talk with such passion and knowledge about this topic, what was it from your own life that fired your interest in it?

Bill Wooditch: You know, Rachel, I'm glad you can feel that passion from across the pond! I think it's in my DNA – it's in my DNA to try to make a difference in life for people. And I see so many people that are so close to making that difference and they just withdraw from the field of play and they decide they don't want to be a participant, they'd rather be an observer. Because it's tough and they get into this cycle of avoidance.

For me, I'll give you one of my greatest, I think most important, takeaways – you've got to feel the fear, and the fire of that fear, as much as you have to know with clarity what it is you really want.

So coming from an impoverished background, as I did, in Western Pennsylvania, I had a fear that I would always have lack in my life, that I wouldn't be able to afford the necessities in life, let alone the luxuries. And, as you mentioned up front, I wanted to thrive, not just survive.

So that fear of just surviving drives me to this day as much as any goal, maybe even more, that I would want. So I got out of the cycle of avoidance, of doing those tough things, and feeling the fear and maybe failing, and started to embrace the fact that, hey, failure is the way forward.

Rachel Salaman: And does your own approach to your own failure follow a pattern? For example, a structured analysis of each bad decision, or is it more organic than that?

Bill Wooditch: You know, in the early days when I was starting out in sales it was very organic. I would do things, I had a whole bunch of energy and a lot of passion to put in play, and I would trip over myself and I would make the same mistake over and over and over. I was trying to feel that on the fly and I didn't have any system to go by, I didn't really know what I was doing.

So when I started to pull back and say, "Look, OK, this is instinct I'm running on, this is emotion I'm running on. I need to dispassionately, logically and rationally write down what it is that I've done that's working and get rid of what's not working, by writing it down in a logical form." When I did that I married logic with instinct and started to do things better.

Rachel Salaman: Now you've talked a little bit about fear already, and in the book you do offer numerous tips on pushing past fear, and one of them is, learn the difference between rational and irrational fear. Could you explain that piece of advice?

Bill Wooditch: Yes. Think of it this way, I'm very aware of separating the two in my talks. Fear is something that, to me, can be a great ally for us – it's the amygdala on alert and it signals danger.

Real danger comes from animal, man or insect, but imagined fears are those things that we bring from our past, our flawed imagination playing the worst-case forward, and to me they're not real fears. They're those future events that appear to be real, they come from the imagination and we're making them into something that's so formidable we don't want to walk through it, let alone get near it.

So, irrational fear is something that's imagined that won't kill us, that won't hurt us, it's not danger – it's the future event that appears to be real. A rational harm comes from insect, man or animal. So there's no saber-toothed tiger in the boardroom, but boy, we sure do play like there is. That's imagined fear.

Rachel Salaman: So how can we tell the difference, because that seems key to this?

Bill Wooditch: Well, I write down what's the worst-case that can happen to us. Is it death, is it you're going to lose your home – what are those real fears? Write them down. Let's look at the worst-case first, in a tangible way (before anybody goes jumping off to be an entrepreneur without a net), let's look at what your fears are.

Are they legitimate? And some may be, "This could put me at harm, this could harm my family." Then maybe we take a limited, different (Ethiopian proverb, "How do you eat an elephant? One bite at a time") approach to overcoming our fear, but we need to be exposed to certain things that make us really uncomfortable. And we need to lean into those things, because when we do our fear attenuates by exposure, it becomes less.

So I would write down worst-case, best-case, what are the things, who are the people (my allies, my advocates) that I need to help me make my best-case reality? So it's an ongoing dialog, and it might take longer than an hour, it might take 10 minutes or it might take days, but let's look at the worst-case. Let's also go back to those things we talked about, "Hey, we failed here, we tried this, this didn't work, why is this going to be different?"

So the questions of why, who is it that can help, how do we do this and when do we start, those are the key questions that we can work on together.

Rachel Salaman: And does this work with all kinds of situations?

Bill Wooditch: It does for me. You know, in our history Ben Franklin is famed for having a T-bar, and on the left he put down all the things that could go right, all the great things, all the benefits of whatever he had. On the right he put all the negatives and he put a weight to them.

And he put that down as left column, right column. And, you know, as basic as that tool is – you take a piece of paper, draw a line down the middle, put a bar on the top, say, "These are the good things, the best things, the benefits I have. Here's the negatives over here" – that Ben Franklin type of model works pretty well when you see your thoughts down and you can start to weigh, "Here's the worst-case, here's the best-case." I'm a huge believer in that.

Rachel Salaman: And is the idea that it should help us fail less? Or is it that it just means that we're going into any situation with our eyes wide open?

Bill Wooditch: Well I think more that you're going into a situation with your eyes as open as they can be. You know, because I think, Rachel, we could have that fire of passion – which I had, that's almost a blind ambition (I love that word, "ambition"), you know, that blind ambition – and you run for it and you're not looking at what could possibly happen that would be the most deleterious thing.

What is the worst-case? You're not looking at it and you're not going into history and bringing up the past experience of failure, to say, "What is it constructively that we've learned from this setback that we can use today to mitigate that worst-case?" You can't always eliminate it, but at least mitigate it.

Rachel Salaman: So it's a way of bridging between past failures that you can learn from and put in that worst-case column, and that may well lead to a higher chance of not failing in that situation?

Bill Wooditch: If you can visualize the bridge it's perfect, that is what this is, it's a bridge.

Rachel Salaman: And in the book you also say that procrastination, distraction and rationalization are conditions we create because we fear failure, but surely that's not always the case. For example, sometimes we may be telling ourselves that we're not ready and we really aren't ready. So how can we tell when we need to listen to that inner voice of caution and when we shouldn't?

Bill Wooditch: At a certain point, you know, rejection is a whole… it's part and parcel of what we do in life. We're going to face it, and the sooner we get out there and accept it and be able to say, "This is part of something that's good because we're getting close to success," well that makes the big difference.

You know, you talk about how do we know – it's individual, in your gut you've got to be able to look in that mirror without denial, without delusion, and say, "I am either BS-ing myself, I'm denying the fact that I don't want to be rejected," or you put yourself in play and in your head you say, "You know what, my gut is telling me this, I'm going to be cautious, I'm going to follow my gut," or, and I think it's an honesty thing, you say, "You know what, it's time to go." But that's an individual thing, I can't tell you what to do with that.

Rachel Salaman: And I suppose, if people do accept that they're going to feel fear, then it makes it easier for them to push past these other things, like procrastination, distraction and rationalization.

Bill Wooditch: 110 percent correct. You're going to face it, it's what you do with it.

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Rachel Salaman: Now in the book another really interesting observation is that no choice is also a choice. So would you explain that, maybe give an example?

Bill Wooditch: Well when you don't make a choice, choices are often made for you. Meaning that if you're in a company and you have an opportunity to create something for yourself, there's a short window of time that you can actually go through that, see it, and seize it.

If you don't, you stand back, you're not making a choice – someone else is taking the opportunity, by default the choice has already been made, you don't want it. So even if you think you can stand back or not, the world is going by, it's not going to stay and you're not going to stay hermetically sealed in a bubble. You make a choice or a choice is made for you, and that's life.

I'd rather be the one choosing and failing (and having the option to choose again based on learned experience) than to stand around and watch the world go by. And if you think about fear, just for a minute, maybe by avoiding, maybe by procrastinating, you're creating a much, much tougher feel[ing] of fear for yourself than going after something.

Rachel Salaman: So as well as no choice being a choice, it's someone else's choice, often.

Bill Wooditch: And there you strike to the core of my DNA, and I hope some of the DNA of your listeners. I want the freedom to choose my life and to live my life the way I choose. To do that I'm going to have to face fear, I'm going to fail, I'm going to fall down, it's going to hurt, I'm going to be rejected, my ego's going to be dented! It's OK. I want to survive and make that same attempt tomorrow, just with a little more education.

Rachel Salaman: In the book you talk about the blame game, so what do you mean by that and how does that affect our ability to learn from failure?

Bill Wooditch: I have a sign I posted on my door. It says, "No excuses." Don't come in with an excuse: come in, give me the situation, what's the issue, what's the problem, what's the challenge, let's work it through. I don't want to hear that the dog ate your homework or that you couldn't do something. I want to hear what is it we need to do, no excuses, don't varnish it.

I think blame is probably the most wasted emotion that we engage in; we blame others for our missteps and we blame ourselves. You know, take ownership, understand that the first – I think context creates clarity here – the first definition of blame in the dictionary is something negative. It's a connotation that we're trying to assign some kind of event to another's purview, not our own. The second one says that we take responsibility.

I just don't like the word, so I don't like blame for misfortune and missteps, and I think that to try to divorce ourselves from personal accountability the first word we use is blame, so I don't want to use that word blame.

Rachel Salaman: One of your very practical tips is you advise us to divide failures into "major" and "minor" mistakes, so could you tell us how that helps?

Bill Wooditch: You know, I think those major mistakes in life are the ones that follow us in life, and we can't maybe foresee or we can't dodge [them] all. But I have gone into my gut to ask this question, "Will I be better for this choice now, as I understand now to be, and in the future, as I can foresee the future to be, will I be better?"

And just maybe sit there in the dark (you know, the dark's that place where all those fears come in and all those uncertainties, but maybe just try to be still) and see if you feel something in your gut, that little voice, maybe imperceptible, maybe a little tug. And then I would go with that and say, "You know, I want to maybe stay away from this."

So some major failures I want to stay away from are those things that will follow me through life, and I've got to think before I do instead of doing before I think, as I did when I was younger. So that to me is a major failure, something that could really put you behind the eight ball financially or could take you on a personal road that's really probably not the best road for you.

So minor failures are things that you can rebound from [and] say, "Hey, you know what, I lost money on this, maybe I lost a lot of money but I still have tomorrow to fight, still have my health –I'm going for it." Major and minor are personal, but I would write them out, as to what can really derail/detract you for a while, set you back and hurt you, as opposed to what won't hurt you, it's just a lesson.

Rachel Salaman: You also say that we should cultivate allies who can help us see our blind spots.

Bill Wooditch: None of us are here and can do it alone. We need each other, we need those people who are pulling in the same direction. (Now maybe a similar direction, not the same direction, meaning those people with similar goals.)

We need those people who can help us maybe look at our blind spots, "Did we see this, did we do that?" or give us encouragement, or let us know that by example they've experienced very similar things, how did they find it?

You're going to find a lot of people that are jealous of people who are successful, who have faced their fears, because most people don't want to face them, who have learned from their failures and then have become and earned their way to success.

You want to associate with those people. Get them as allies, distance yourself from the people that would be adversaries, and move forward.

Rachel Salaman: And these people might be colleagues, they might be family members, you can find them anywhere, is that right?

Bill Wooditch: I've found them everywhere, I have family that begged me to stay back on the East Coast and never leave my job I had in a factory. Now they visit me in California. Also you have a number of naysayers out there who don't… at a certain point, when you become successful in life (and I think your listeners will relate to this) you get to a certain point of success that people will champion your cause to a degree, until you start to eclipse what they believe is their self-worth and their esteem to society.

And then maybe the little green monster of envy comes out a little bit, and maybe they try to cut your legs off with that. You've just got to be careful and you have to use your acumen, to say, "Who are and where do I find these people who can help me to get to the next level?"

Rachel Salaman: Now you mentioned goals earlier, and I wonder if we could talk a bit more about them now. In the book you say that they can be used to "fail your way forward." What do you mean by that?

Bill Wooditch: You know, when you set goals, SMART goals (specific, measurable, attainable, relevant, time-sensitive goals) – taking small steps, small steps towards your goal, maybe just the smallest thing, to accomplish one thing more than you accomplished the day before, do that and watch how you're moving toward your goal.

And you could fail a few times moving toward your goal, but as long as you're failing forward… failing forward means this: you've taken the lessons of a past failure, you've applied them, you have a degree of success. That might not be total success, but you have a degree of success because you have learned from that failure instead of withdrawing, quitting because you were just trying, you were a dilettante, you're a professional, embrace the lesson from failure and move an inch forward tomorrow – that is failing forward.

Rachel Salaman: And what's the best way to set effective goals then, with that in mind, with failing forward in mind?

Bill Wooditch: You know, I think that, as I do talks across the United States, one of the biggest things I've found is that people intimately know (and I mean intimately know) what they fear.

When you think about being in the dark, alone… "Here's my bills, this is all the bad stuff that can happen." We always know our fear, but we really, truly don't know with clarity what it is we really want.

We could say it would be nice to have the Ferrari, it would be nice to have the Lamborghini, the ocean house, yeah, yeah, yeah, but what do you really want? What are you willing to give up to get it (most important)? Are you willing to burn your boat, make the ultimate commitment, you know, how much pain can you endure? And I'll tell you, the first place where pain comes in: rejection, fear and failure.

Rachel Salaman: So if you were setting goals, is it just a case of setting those little ones so that you can take stock at every point as you progress, and do that assessment of, "How can I learn from each of these steps?" Is that how you would do it?

Bill Wooditch: When I started out and when I came out in business, I came right out of school and I couldn't tie a tie, didn't have a suit. [I] had a station wagon, a brown oxidized car with no hubcaps, and I posted on the wall a picture of a sports car and a picture of a place in California (I was on the East Coast) and those were my sub-goals.

But my big goal was this: lifestyle options. I wanted to create lifestyle options and freedom, that I can make choices and I could put myself in a better position in life from those choices coming to fruition. So, my small goals as I was marching toward financial freedom, were… here is my milepost – the goal wasn't to buy a car and to live in California, those were sub-goals. The goal was to have financial freedom and the wherewithal to move where I wanted to move, when I wanted to move. That was my big goal.

I'm a reductionist. Work it backwards, find your big goal, then small steps toward it. Work backwards, "What do I need to do, how do I get there, what is it?" And along the way, hey, it's nice to buy the car and live wherever you want to live.

Rachel Salaman: Now we've talked a little bit about mindsets already but let's focus on that now, and in the book you talk about the difference between fixed mindsets and growth mindsets. What can we learn from this and how does it relate to failure?

Bill Wooditch: Carol Dweck, the Stanford researcher that, in 1998, conducted a study of about 400 fifth graders. And the study involved problem-solving tests, to see how they coped with adversity and challenge. When they completed the initial test, students were offered a choice between taking a very difficult test or an easy test. Two-thirds of those students who received praise for their intellect took the easy test.

They wanted to maintain that goal and that societal expectation, "Wow, you really are that smart, you're good." But the students who chose the easy test, although they didn't want to risk losing their smart label, the other ones, 90 percent of the students who were praised for effort took the top test, they were looking at the effort, an insoluble problem, but they just wanted to keep trying to solve it.

She tracked these students through life, she found there was a striking difference between the way that the praise-oriented, "I don't want the top test," and the effort-oriented students, responded to failure.

She also found something that I love. She found that willpower was a greater predictor – and "willpower" because the students who maybe weren't chasing that smart label – was a greater predictor of future success even over IQ. So I love what she did there.

I find that the fixed mindset, that's the people who look to the grade, who look to not push themselves, who have a "this is the way it's going to be" [outlook], they're change-averse, they're a loss-averse, they don't want to put themselves in play, they want to protect their image.

The other ones that are growth-oriented, man, those are the ones that learn, those are the ones that embrace change as the way forward. Those are the ones that are willing to fail, fail, fail, fail, and then learn from that, and to keep going just because.

Rachel Salaman: And can we change our mindset?

Bill Wooditch: You know, I think that you've got to be willing to change. I've been able to change my mindset to a degree, but some of it is that confirmation bias I carry with me on how I think the world should be.

So, when I can distance myself from that parochial thought, that this is what I know, and I can follow my inner Plato when he was asked, "You're the wisest man in Greece, how do you know so much?" And he said, "I know that I don't know."

When you're willing to accept that you don't know, when you're willing to open the gates to possibility, you can change your mindset to a degree. But if I'm going to change someone else's, it ain't going to happen.

Rachel Salaman: Right, so like a lot of things, it has to come from the person themselves, and then they might be able to, for example, develop a growth mindset from a fixed mindset?

Bill Wooditch: Yes. You know, Rachel, like everything else in life, it's by degree, nothing's going to happen overnight. So if you're willing to open yourself to the possibility of something in the future that you don't know, that makes you lean into the discomfort of the unknown and you're willing to take the hit to your ego, you know, you're willing to say, "Wow, society's not going to determine my worth, I am."

You know, so many people put themselves out there for societal approval, and that's where the real rejection and fear comes from. Because, as babies, we have only two innate fears – falling and loud noises. And we learn the rest of those in schools, on the playgrounds, and growing up and life, and man, we don't want to be rejected! So why put yourself out there? That's the huge dynamic behind really learning from failure.

Rachel Salaman: Well a message that threads throughout your book is that we should enjoy this journey of successive failures. Could you expand on that and give us some tips on how we can savor our failures?

Bill Wooditch: You know, I've always been a contrarian, so your listeners are going to say, "Oh that guy's crazy, how do you savor a failure?!" The only way I've learned to savor failure is from success and when I'm really recounting what it took to become successful.

Because it was such a tough hill to climb, "Remember when we did this and did this and it was insurmountable odds," and all of a sudden the champion appears, "but we did it!" So you really can savor them in retrospect. I don't know that when you're in the stew you can actually really savor it.

So I think that looking back you savor it and say, "This is what I learned." And it really steels you, it gives you a little more power to go forward, knowing that you've overcome things on your champion's journey, on that hero journey – you've fallen, you've gotten back up, "Ah!" and others will look at that and see that passion, see that fire and they feel it. And they go, "You know what, yeah, there's a lesson there, success has left clues, maybe we can do it too."

Rachel Salaman: Bill Wooditch, thanks very much for joining us today.

Bill Wooditch: It's been great. Thank you, Rachel.

The name of Bill's book again is "Fail More: Embrace, Learn and Adapt to Failure As a Way To Success."

I'll be back in a few weeks with another Expert Interview. Until then, goodbye.