What's neXT?! Celebrating Failure

• The tension between stability and growth

“Predictability, productivity, and efficiency without dynamism, novelty, and growth leads to stagnation. But dynamism without control leads to chaos. We need both—and our culture tends to manage only one well.”

• Managing fear of failure

“We don’t have a culture that’s particularly well tooled to manage dynamism, novelty, and growth. And so we approach that with a lot of fear. And that’s where failure comes in.”

• Managing fear of failure

“We don’t have a culture that’s particularly well tooled to manage dynamism, novelty, and growth. And so we approach that with a lot of fear. And that’s where failure comes in.”

• Personal experience of confronting fear

“Everything was going great in my professional life before deciding to start my own company. But I was really stagnant.”

• Guardrails for exploring chaos

“Putting clear guardrails around how much chaos you’re willing to explore helps you take risks without being reckless.”

• Choosing small failures over large ones

“Any day of the week, I will choose a string of small failures leading to a large success over a string of small successes leading to a large failure.”

• Learning by doing, not planning

“Kindergarteners beat MBA students at building towers because they fail fast, fail early, and learn quickly—while the MBAs spend all their time trying to perfect the plan.”

• The contribution of older generations

“Older people tend to sweat the small stuff less. They help us situate our experiences into a coherent narrative, seeing setbacks as part of a larger arc.”

• Failure beyond productivity metrics

“Failure is so often associated with the failure to be productive or efficient. But growth, exploration, and self-development are legitimate outcomes too—and they matter just as much.”

Carl Honoré:

For something completely. For something completely different. We are going now to listen to short keynotes entitled Celebrating Failure.

Celebrating Failure.

Yes. Failure.

This seems to me the perfect time and place to talk about, to tackle the other F word, failure. Why is it the perfect time and place? Well, I can think of two reasons.

The first reason is that we’re in Toronto, right, which is a global city admired the world over. But it’s a city that at the same time has a deep, abiding relationship with failure, at least where hockey is concerned.

I had to do one Leafs joke, right?

The second reason I think is even more compelling, and that is that failure is a part of life.

It’s a part of life. And living longer, longer lifespans means failing more. So what are we going to do with all that failure? How are we going to make sense of it? How are we going to harness it? How are we going to channel it?

How are we going to capitalize on can we make failure our friend?

We’re very lucky to have with us today a man by the name of Brooke, who is, by all accounts, in the world of failure, a big success. And he’s going to walk us through some of these questions.

Short keynote, and then afterwards, we’re going to do some Q and A.

So, Brooke, the stage is yours.

Brooke Struck:

Thanks for that. Thanks for that. Three, Number seven. There we go.

Carl, come sit with me. Make me feel comfortable at home, like we’re in the living room by the fire.

Carl Honoré:

I love a bit of fireside chat.

Brooke Struck:

So thank you for the warm introduction. Thank you, everyone, for being here today and for sharing your insights and your energy, your positivity, your enthusiasm.

I want to start off with a more interactive portion of this keynote with some shows of hands.

So who here thinks that improvement is good?

Who here thinks that improvement means things have to change?

Who here thinks that change requires learning?

Who here thinks that learning involves occasionally stumbling?

Who here lives and works in a culture that tolerates sound like.

Who here lives in a culture that holds inconsistent values?

Thank you. So that’s. Thank you for the interactive portion.

So that’s actually fun. And what I want to talk about is the tension between these values. And to situate these two poles, what are the values that I’m talking about?

On the one hand, we’ve got predictability, productivity and efficiency.

And on the other hand, we’ve got dynamism, novelty and growth. And actually, we need both of these things, either one on their own would be very bad.

Why is that?

Because predictability, productivity, efficiency, the kind of dark underbelly of that is stagnation. Things just always stay the same. And on the other hand, dynamism, novelty, and growth, the dark underbelly of that is chaos. Right? It’s kind of out of our control.

And I just want to point out that I really appreciated your comments about kind of the importance of masculine dominance in this, because that perpetual drive for control is a very kind of masculine energy that we bring.

And I can’t see where the elder was who gave us the introduction this morning, but it’s also a very colonial energy. This desire to dominate and control is both masculine and colonial.

And so we need both of these things. But due to the kind of cultural heritage that we have strongly informed by masculine and colonial traits, we tend to manage one of those things really, really well.

We’ve got lots of tools for measuring and managing predictability, productivity and efficiency.

The challenge that we have is that we don’t have a culture that’s particularly well tooled to manage dynamism, novelty, and growth. And so we approach that with a lot of fear. And that’s where failure comes in.

We look at that dark underbelly, underbelly of all that wonderful dynamism, and we see, say, I’m afraid of that chaos. I’m afraid of what might happen that I can’t predict and that I can’t control. And often what that gets us doing is just kind of like running back in the other direction. Right?

We say, no, no, we’ll just go back to the very, very comforting, you know, control, predictability, efficiency, productivity. And just as a, you know, a bit of a spoiler, like, that’s not just in our professional lives.

How many people here either do this themselves or know somebody who sometimes worries about whether they are using their leisure time optimally?

And so what I’m here to propose, and, you know, I want to put out something relatively straightforward and then open up the conversation is really the tools for managing change and not having so much fear of that chaos.

And I’ll share a bit of a story about myself.

So my own most recent professional transition, leaving my former employer was the Decision Lab, and deciding to launch my own business, Converge, which was something that I had been thinking about doing for about a decade and just terrified me.

I spent so many moments just shrinking away from this thing and, you know, from the predictability, productivity, efficiency piece. Everything was going great in my professional life before deciding to start my own company. You know, I had a Nice title and a stable company and a good income, these kinds of things.

But I was really stagnant.

There was a type of work that I wanted to do with my clients and a type of skills that I wanted to bring into, into my professional life that I didn’t have the opportunity to do. And so I really felt the weight of that stagnation.

And of course, the opposite side of that was this, you know, like sheer white knuckle terror about starting my own company and potentially never earning another cent in my life. You’ll notice by my bow tie budget, that hasn’t happened just yet.

But you know, one of the things that I realized in reflecting on this is that if I just started another job, if after 18 months I absolutely hated it, I would leave and I would find another job. Also, if my employer hated me and I wasn’t doing a good job, they just fired me. Right.

And what I realized about starting my own business is that if after 18 months I was really unsure and all these kinds of things, I could fire myself both as an employee and as a boss, I could just leave my own company that I had started and go and get a different job. And so that for me was a really valuable insight to have.

All of a sudden I could put a bit of a kind of box around, like, how much risk am I talking about here? And so that’s the first tool around managing change that I want to share with you is putting some clear guardrails around.

Just how much chaos we’re willing to explore and to put safeguard rails places.

And that’s an important thing to consider here as well. Some of us have the opportunity to put guardrails way out and still be quite safe. Others have guardrails that need to be quite close in in order to keep us in a safe space. We don’t have the kinds of safety nets to take as much risk.

So the guardrails is the first piece.

The second is about really being clear about what it is that we want to learn and what it is that we want to explore in these moments of chaos. And to put that in a very boring way, that’s about indicators for me, like if I’m going out and I’m exploring, how will I know that I’m actually making progress in the direction that I want to?

What am I keeping track of to see whether I am actually happier doing what it is that I’m doing, whether I’m moving towards a financial situation that’s going to be sustainable for me and for my family in the Longer term.

So that’s the second piece is, you know, when we’re out there in the guardrails, what are we looking for? What are we looking at to kind of assess how we’re doing in this adventure?

And then the third is basically a commitment to sit down and review those indicators and also to continue growing and continue exploring, to continue kind of encountering that chaos, or if we see something, you know, if our indicators are telling us is it’s not moving in the right direction and it’s not close and these kinds of things.

We also have to be committed to killing the experiment and saying, I’ve tried this. I gave myself a certain Runway to work with. I burned through all that Runway. I’m not where I need to be. I need to try something else.

And to be willing to say that even though in some quite material terms, in the world of predictability and efficiency and productivity, that might constitute a failure, I didn’t go out into the chaos for those things.

Those things were what I wanted to get away from because of the stagnation that they brought with them. I’m willing to accept that, that exploration on certain terms may be a failure.

But there’s a difference between having a failure and being a failure.That is extremely important.

Certainly for me, from a firsthand perspective, I will tell you that that’s very, very important. That whether things work out or whether things don’t, it’s not kind of this. This indictment of my character.

And so, you know, what this has allowed me to do is to go out and really court feedback and to learn and to explore and to see what’s out there in that chaotic environment. And what I’ve taken away from that is that along the way, I’ve had lots of small failures. And in fact, I set myself up for small failures.

The way that I approached starting this business was that I had an idea of what I wanted to do. And I basically lined up a whole bunch of friends and confidants, and I asked them to tell me every reason that that was not going to work. And so all of those conversations were just failure after failure after failure.

But they were such valuable feedback in refining the idea that I had has brought me to where I am now, which is how all of those small failures have contributed to what is overall, in my estimation, the larger success.

Now, by contrast, I could have said, I want to line up a whole bunch of small successes. I could have asked all of those people, tell me all the reasons it’s going to be fine. And being my Friends, they probably would have humored me and told me, don’t worry, Brooke. Everything’s going to be great.

And they would have puffed up my ego, and. And I would have blissfully gone along on the wrong path. And that string of small successes would have led me to the large failure. And that, for me, again, has been a really valuable insight. I’’m really happy.

You know, any day of the week, I will choose a string of small failures leading to large success over a string of small successes leading to a large failure. And there’s an interesting piece of research that I was actually just reminded of a few moments ago, and I want to share it with you.

So there’s this exercise where basically you put a whole bunch of materials on the table and you say, okay, you’ve got five minutes. Build the tallest tower that you can with these materials in the next five minutes. And this exercise has been conducted thousands and thousands of times with different people.

And one of the things that reliably comes out is that in the grand battle between MBA students and kindergarteners, kindergarteners tend to do much better at this exercise than MBA students do. And the reason for that is that MBA students spend so much time basically convincing each other in the group about what the best way is to proceed, and then they build one or two towers, and it doesn’t work all that well.

Kindergarteners don’t think at all about the plan or a business plan or trying to convince anybody or any of these kinds of things. They just start building. And the first tower they build, let me tell you, it’s terrible. It collapses almost immediately.

But then they build a second tower, which is marginally less terrible. But as they keep going, they just build so many towers in five minutes that they end up figuring out how to build a bigger tower than an MBA student or a group of MBA students can do at the same time. So this, for me, is a really practical illustration.

They court small failure to get to the big success instead of trying to line up these small successes of convincing other people, you’ve got the right idea ultimately leading to the large failure.

And so the last piece that I want to talk about is how this all comes back to aging, because, of course, that’s what we’re here to talk about today. And I want to talk about the role of older people, let’s say, especially in workplaces, but I think that this applies more widely as well.

What is it that older people bring to these conversations?

About exploration and about, kind of, know, going out into the chaos and learning the first Is that older people tend to be less caught up in the small day to day stuff. You know, being able to rack up these small failures. As I say, for me, it’s been really important to just not care so much about the small failures and not sweat the small stuff.

From what I’ve seen from the research that I’ve read, older people just tend to be better at not sweating, throw the small stuff. So when we think about how to effectively go out and engage in these kinds of chaotic dynamic environments, not sweating the small stuff is something that older populations can really help to bring to the table.

A second is about hypothesis formulation, which sounds big and basically just means coming up with an idea that’s credible about what might work. And that of course, is really informed by experience.

If you’ve seen a thousand towers built before and seen a thousand towers fall, you. You start to get a feeling for what works and what doesn’t. And so you can land more quickly on formulations that will actually start to get some traction.

That’s the second piece.

The third is around narratives and fitting projects into a wider arc.

And that relates back to a comment that was made earlier today about losing everything not being the end, right, that we can, we can lose everything externally, but actually what’s inside can’t be taken away from us. And when we have that assurance inside, we know that the external losses, setbacks are actually something that just help us to move forward.

Yes, they’re challenging. Yes, it would be nice if things were a little bit smoother and more kind of up and to the right than they are. But ultimately, you know, down and to the right happens also. And we learn a lot from these moments of challenge.

We learn a lot internally and this constructs and contributes to who we are as people.

So that, I think is a third element that I would really advocate is that the piece that older populations can help us with here is to situate, you know, these, these kinds of different pieces of the arc of our lives into one coherent narrative, which I think also fits nicely into this idea of the elders as kind of story keepers, right, that they are, they are the stewards of our stories.

They help us to craft narratives and to make sense of who we are, even to ourselves.

And so where does that bring us back? You know, there’s this kind of potentially unintuitive conclusion that, you know, dynamism and innovation and all of these kinds of things which are supposedly the province of the young.

Older people have really, really valuable contributions to bring to this. I’m not going to say that older people are better innovators than younger people. I think, actually there’s a point that came up in the session that Lisa was running earlier that really snapped this in focus for me.

It’s not about saying older people are better at this than younger people. It’s about saying groups of people that have a mix of older people and younger people will be more effective at these kinds of things than groups that are either dominated by entirely young or entirely older.

And so what I want to conclude on there is to say, you know, I think that there’s a real opportunity to change the way that we think about failure and to change the way that we think about the role and perspective and contribution of older people in these explorations.

And I can end on a bit of a kind of a call to action or like, what do we do next? What’s lacking is really the tools and the mindsets that help to shift the culture towards seeing failure on the kind of predictability, productivity, efficiency piece as something that we just need to accept as the cost of not living in something stagnant.

If we want dynamism and growth and novelty, we need to embrace a little bit of chaos, and failure is going to be part of that.

Thanks very much.

Carl Honoré: 

We have a little conversation now. Again, room is open, the virtual room as well. So anybody has a question, just throw a hand up and we’ve got our trusty team. I’m not sure how well the mics are working, but we’ll get one out there if there is a question.

I’ve got loads of questions that need more. Now, if you speak, you said at one point you talked about, and there’s.A lot of research that backs this. Up, that as people get into their life, they’re less prone to swiping small. Stuff, to getting dragged down by the small feelers.

Is there a way for younger people to learn to do the same, or is this something as a younger person, one just has to wait for that later life.

Are there some tools or things that you work with that can teach people to do that earlier in life and.Not have to wait for it from there?

Brooke Struck:

Yeah.

So part of it is around, you know, the tools that I mentioned, around, like putting out some guardrails and these kinds of things and really assessing, like, what degree of risk you’re willing to take.

That’s part of it.

But I also think around the mindset piece and the culture change piece, it’s really beneficial to spend time around older people.

This is one of the things that I find in our education system that really doesn’t serve us well. We are so segregated by age. And one of the things that I appreciated growing up in my own circumstance where I had cousins who were quite a bit older, I was the youngest.

But being in mixed age groups and being, you know, sometimes amongst my cousins, always the youngest, amongst some of my friends who have younger siblings, then I was the older one in other groups, I was, you know, kind of somewhere in the middle. But the fact that we play different roles in.

In different groups depending on where we fall on the age spectrum, I think is a really important moment for groups growth.

And so I would encourage people to participate in more mixed age groups and to occupy those different roles and see what they feel like.

Carl Honoré:

Even then, it’s useful to have a mixed group where older people are not sweating small stuff. And it is then therefore useful for younger people to be sweating in a weird way. As long as you’re doing it all together at the same team.

Brooke Struck:

That’s right. So two things happen.

The first is if, you know, if the dynamics within the group are managed well, you’ve got different people with different sensibilities who are all kind of covering each other’s blind spots.

But the other thing is that the more we participate in those groups, the more we kind of become sensitized to the kinds of discourse of the other, the more we start to understand their perspective.

And when we want to take a more balanced perspective, even in our own reflection, we can kind of channel our inner, you know, our inner grandpa, in my case was my grandfather, who was the, you know, a very, very important early influence in my life. He was quite old, even when I was in my teens and early 20s, that had an enormous impact in the way that I think about aging and the way that I approach older people.

So there’s, there’s also this aspect of like, kind of appropriating is the wrong word, but like really internalizing that. That voice of other people that you’re used to speaking with. And if you speak frequently with a wide diversity of other people, you internalize a diversity of.

Carl Honoré:

We live in a very perfectionist, formative culture. Is there a danger that failure becomes just one more thing and you fail at.

By the way, we only have two minutes left.

Brooke Struck:

Yeah, and that really, you know, it comes back to the earlier point around, like, productivity and efficiency. Right. That like, actually if we could just kind of turn down the temperature and turn down the volume on wanting to optimize absolutely everything, I think that would help us to that would help life to just go better for us overall.

This is not just about innovation in a corporate context. This is not just about trying to learn a new language and do your friends on duolingo like, if you just weren’t as worried about your, you know, your likes and reshares on Instagram, like your life, objectively speaking, I think would be, would be better.

I think there’s enough research out there showing that, you know, the detrimental effects of that kind of, you know, social media dopamine chasing on our mindsets, that actually just dialing back that kind of optimization across the board is helpful.

Carl Honoré:

I noticed during the talk that you didn’t actually use the word failure that much. And I’m wondering if. Do you have an uneasy relationship with the word? Do you think, for other words, do you think the word holds us back from making use of.

Brooke Struck

Yeah, yeah. So one of the reasons that I don’t like the word failure or kind of don’t, you know, plunge into it headlong is that it’s so often associated with the failure to be productive, the failure to optimize. And in so doing it like tacitly endorses that language.

That efficiency and productivity are actually the only game in town and that I don’t agree with. It’s not the only game in town.

There’s also all of the stuff around exploration and learning and growth and development, including self development. All of that stuff is totally legitimate and totally important. And if, if I do shy away from the word failure, it’s because it so often co opts us into those conversations.

We’re actually only one kind of outcome is allowed to count. And I will not get on board with that.

Carl Honoré:

Final question. Role models are so important for helping us change and grow.

And I’m wondering how important you think it is for each of us to have our own pantheon of people who have failed. Well, do you have your own role models for failure?

Brooke Struck:

Yeah, yeah, I definitely do. And it’s valuable.

In my experience, it’s been really valuable to know those people, not just to kind of see them from afar, not just to read a book about, you know, Steve Jobs creating something that absolutely, you know, flops, that’s great. But the actual interpersonal experience of knowing somebody who has experienced these setbacks and, you know, it doesn’t detract one iota from my ability to admire this person, to recognize that somebody that I know in a really flesh and blood way has also experienced setbacks and that I still hold them in such esteem in such regard. That’s been a very powerful message.

Carl Honoré:

Wonderful. Well, thank you very much.