How To Overcome the Fear of Failure & Feeling Stuck | CEO Wynne Leon

Wynne Leon Transcript

 [Wynne]

So the thing about sharing and trying is that there's a lot of things that keep us from trying. What I like about people coming on and sharing their stories is that it helps create the ideas of what people can try.

[Roger]

How much of your life are you designing the “perfect plan”… instead of actually trying to do the thing you care about?

As a proven leader, coach or consultant, you’ve probably had a lot of success for having the answers, managing the risks, and getting it “right” the first time. But as your career has grown, the stakes have increased, you’re worried about committing the wrong move. 
 
 And that’s the trap. While you’re overthinking, you’re risking burnout and the feeling of being stuck, even when from the outside everything looks amazing.

Welcome to What Do You Know To Be True? where we have conversations with people who are becoming more of their possible selves, one right next step at a time.

I’m Roger Kastner and I’ve spent over 25 years working with leaders and teams to co-create the strategies that bring clarity, possibility, and humanity back into their lives and the workplace.

In this conversation, I sit down with Wynne Leon, and we talk about her superpower of “being a good tryer.” 
 
 As the CEO of her own consulting company, an amateur mountain climber, and the host of the “How to Share” podcast, Wynne demonstrates the courage it takes to boldly try new things. Wynne shares the 3 principles she follows that will make you more confident in trying new things too.

If you are ready, let’s dive in. 

Hey Wynn, thank you for joining me today. I'm grateful that we are together today.

[Wynne]

Roger, it's so good to see you. I know that we live just like five miles apart. And we met because we had a podcast guest in common who lives in Copenhagen.

So, so nice for people to bring us together.

[Roger]

We are bringing, we are making this world smaller, whether it's our zip code or whether it's the whole globe. I'm excited to learn more about your superpower of being a very good trier. But before we get there, I know you to be the CEO of Avitiva, a collaboration software and implementation consulting firm.

And you're the host of the How to Share podcast. Before we get too far, what else is important for us to know about you?

[Wynne]

Thank you for having me on. As I said, it's so nice to meet you, my neighbor and co-friend in the podcasting world. You're right.

I've spent a whole lifetime, you know, working on collaboration, but it sort of ties into that story of why I'm a good trier. Even as I'm a computer consultant by job description, I graduated from the University of Washington with my degree in electrical engineering. And I landed a job designing the computer network at our city's electric utility.

And, you know, this was when, you know, company access, corporate access to the Internet was brand new. And so I would, you know, design something and then the communications people would install it. And then if there was a problem, I would troubleshoot it.

And what I found was I had a knack for troubleshooting. So I started teaching a troubleshooting course. And it's based around a simple but hard to do philosophy that you have to try one thing at a time and document it.

You know, why is that so hard? You know, because it's a little like getting lost in the woods. You take one turn and then another turn and pretty soon you're hopelessly lost unless you left a Hansel and Gretel trail along the way, right?

Well, we do the same thing with troubleshooting. We change one setting and then another and another and we get that feeling of panic. But what you need to do is change one thing at a time and write down what it was.

And if it didn't solve the problem, you undo that change before you try the next thing. This works on several levels. You know, it keeps that panic from overtaking you.

You keep that panic that's, you know, I'm never going to fix this. It provides a system so that even if you don't know how to fix something, you at least know what to do next. And when you fix it, you know why.

And you can learn. That's sort of the foundational part of the story because once I figured out that I was really good at troubleshooting and trying, it just led to me trying all sorts of other things, but also knowing that I needed to share. So I'm bringing this all back to Avativa and collaboration because, you know, what good is it if you, you know, you have a superpower or you learn something and you don't share it?

And, you know, and you know that. I'm sure you've seen it repeatedly. You work in project management, change management.

And when we collaborate, we can create meaningful, sustainable impact like your frameworks. You know, a framework can help you get something done, but sharing your framework can help a lot of people get things done.

[Roger]

There's something brilliant in this idea of not only writing down the one thing that you're trying, but then if it doesn't work undoing that one thing, that feels different. That feels new. And I must admit when I'm troubleshooting, yeah, I do the first thing is you unplug it and plug it back in, see if that works.

But then the second thing I try, you know, at home, I probably don't write it down, but at work we do make note of it. But undoing it, that feels like a pro tip right there.

[Wynne]

It is because it could be the combination of things, but it gets more complex if it's, you know, two things that you need to do. And sometimes you get a little bit of a hint, but every time you do that, if you do one thing, you can get the hint related to that thing, you know, and it's the same with getting lost in the woods, right? If you go back to the last thing that you remember, then it's a little bit easier to find your way back.

[Roger]

And now I'm thinking about when you hear stories of problems that happen within the cockpit or in the surgical room, something goes wrong and it's not noticed. And then someone, you know, it is noticed and then something's tried and something's tried. And pretty soon these catastrophic failures aren't because one thing, it's because a string of things.

That's coming up for me in this description of try one thing, undo that thing. My, you know, can you do that in a cockpit? Can you do that when you're operating on someone?

There might be a little bit more complexity there, but as something that you and I were talking about before we hit the record button around simplicity of trying to keep things simple, especially when most times we're dealing in complexity. So how do we not add to the complexity? That's what I'm taking from this tip.

Right.

[Wynne]

And I think the other thing that I learned in troubleshooting it in any realm is that it keeps, it's that system approach. It's that keeping the panic at a bay because, you know, when we start to create those, I'm going to change and change and change, we start to feel unfounded and we start to feel nervous about it. You know, will I ever have the system back the way that I wanted it in the first place or the way that it was?

We just build on our own panic. So taking the time to undo it almost is a pause.

[Roger]

Oh, that's so good. Yeah. From the project management days, I'm remembering something that I would do if, if everyone was freaking out, obviously a great time for me not to freak out for me to, you know, try to be calm for everyone else.

Right. And the converse is true. If no one was freaking out, that's the time for me to like throw on this management hat and start like, okay, what's about to hit us or what's, what's going wrong that we're not aware of just yet.

[Wynne]

So that's such an interesting observation that sometimes, you know, that panic does help us in or not even panic is as you were describing, but that energy of, okay, you know, do we need to add a little freak out energy is, I mean, that is putting energy into the system.

[Roger]

And everything is done within the system, right? No, no one does things alone anymore. Right.

So speaking of not doing anything alone, you're the host of the how to share podcast where you talk with people about how they share and it's, it's a wide range of things that they do share. And I'm curious if you could tell us a little bit about the mission of the podcast and how your guests share the things that they share and why and how is that important for you to share all of that with us?

[Wynne]

Right. Well, thank you for asking. That was a really nice segue.

I appreciate that, you know, softball for me to hit. So the thing about sharing and, and trying is that there's, there's a lot of things that keep us from trying. I think in my experience, you have to believe that you can, there's a lot of fear, there's vulnerability in trying new things.

And so what I like about people coming on and sharing their stories, which, you know, they will share, you know, often they've written a memoir, sometimes they've written a novel or just, you know, their experience like having a guest like you is that it helps create the ideas of what people can try or seeing how other people can, and they're, they're, they're sharing the things that they tried along the way. Like I just had a wonderful guest, Nancy Shear, who was a teenager when she snuck into the Philadelphia orchestra.

She was 15 years old. It's in the early sixties. You know, the Beatlemania was just on the rise.

It's, it's amazing that she got attached to classical music, but she did. And she just, she knew she had to hear more, but she didn't have the price of a ticket. So she went to the box office and she got a few passes and that worked.

She ran out of luck doing that. So she stood for several weeks by the stage door in the back on the, on the, for the Friday matinee. And that led to her meeting Eugene Ormandy, who was the conductor of the Philadelphia orchestra at the time.

And he showed her how to go in the back door and, and sneak in and going. But this is where the story is so cool. The back door was where she got to meet people like Leopold Stokoski, the people who were doing the librarian work for the orchestra.

Then she got hired as an assistant librarian for the Philadelphia orchestra at age 17, like going in the back door was actually fundamental to her story. And, and when I hear stories like that of how people have tried things and how people have navigated their path, it just inspires me in that. And I know it inspires all my listeners because you get to see what somebody else tried.

[Roger]

Okay. Now, now that it makes, it makes perfect sense why we're talking about, you know, how to share. I believe that for us to really know something, one way to check or to improve our knowledge of mastery is to actually teach others.

And I think when we're, when we're sharing a lot of time, there's that intention of trying to not only share the story, but also maybe teach, teach an experience, teach a feeling, teach a skill. And so it, it makes sense that you're, you're talking about this arena, this conversation around sharing is really a way of amplifying ways that people have tried things multiple times to find the thing that works for them as a way to inspire other people to try multiple avenues, to achieve the thing that they're trying to achieve, because going through the front door, isn't always going to work.

[Wynne]

I love the way you sum things up, Roger, you are brilliant. No wonder you're so good at this.

[Roger]

This next question might, I mean, you might've already answered it, but I'm wondering if there's another layer to go to it with the superpower of being a very good trier. Tell us what that means for you.

[Wynne]

It's funny because when you and I talked about this originally, you asked, why don't you call it, why do you call it trying? Why don't you call it a persistence or one of those other words? And I think the reason that I call it trying is because, you know, it is sort of that same troubleshooting methodology, which is you try one thing and then you need to, to know, you know, when to undo that change and, and do the rest thing.

You know, one of the things that I've done a lot of is climb mountains. Before I became a parent, I climbed a lot of, did a lot of amateur mountain climbing. And there are times that you do not want to go to the summit, you know, it's avalanche conditions, weather conditions, condition of the team altogether.

Something is, you know, you don't just push on because that can be dangerous. I mean, we have a lot of stories about that. Think about into thin air, right?

People were just pushing in. The other elemental and into thin air makes me think about this is having a turnaround time. Guides often say, if we don't get there by 2 PM, we're turning around and no matter where we are, we could be 50 feet from the summit.

It does not matter because we're turning around. That's the only way to be safe, right? So that's why I call it trying and not persistence or one of those other, you know, we're going to muscle through it.

It's a way of navigating to find our own path. I think the other, it, you know, I've got a lot of different examples of things that I've tried that have worked or haven't worked, but it is that spirit of just finding the next right thing to do.

[Roger]

And in my coaching program, that was one of the mantras of help the client find the right next thing. There's also a song, I think, in Frozen 2 about the next right thing that someone made me watch the movie, so I see that one song. But anyway, yeah, just that willing, yeah, I love, and I love the explanation then and I love it now, the idea of the trying versus persistence or, you know, whatever, whatever word you want to throw at it.

One feels like effort. One feels like curiosity with those guardrails, right? Of when have we tried enough?

When are we turning around? When do we know that only bad things happen after this point or the risk of those negative outcomes come at that point? So I love that idea of trying.

There's also something very playful about trying, whereas like a persistence feels like a struggle, right?

[Wynne]

That reminds me, I mean, that's such a good example because the other day, you know, when we were having our atmospheric river here in Seattle, as I'm sure you remember, I woke up in the middle of the night or 5 a.m. to a dripping coming in my bathroom, and it was, you know, the water was coming in through the fan, so I was like, well, I don't really know how to fix a roof. I've never fixed a roof before, but I could see that it was coming from the fan and that was like, you know, I kind of troubleshooted it enough that I knew, because I covered it with a garbage bag and it stopped. I'm like, okay, so I just know that even though I don't know how to fix a roof, I know where the problem is and I can just try.

I can just go to the store, see if I can find something that I can, you know, caulk around the vent, and I can just try. I'm not going to hurt anything, and so there is that playful sense of it. You know, I can just try this thing, and if not, then I can call a professional.

[Roger]

I'm having a conversation with a friend recently around permission and giving ourselves permission to try things, and she has identified that, in her observation, younger generations are less likely to try, and they need to be given permission. When we were younger, there was no road map. There was no path for us to take.

There's maybe some role models, but there's a lot of, there's just this acceptance of, you got to go out and find your own way. You got to go experiment. You got to, you know, there was a little bit of, like, resilience and preservation and just putting yourself out there.

Yeah, as she was saying this, I'm listening and I'm thinking about my own kids and thinking, yeah, there is a little bit more of, you know, a little bit of a fear of trying things, fear of, you know, maybe wandering a little further away from the tribe, and I'm wondering, you know, as a parent of the younger generation, what did I do to contribute, which, you know, can't go back 20 years and change, but what are ways that we can encourage other people to try, and I love the How to Share podcast has that as a mission.

What else have you found to be, almost like giving permission to other people to try?

[Wynne]

Right, that's a such a good question. I love it. You know, I think, and I'm going to go back to mountain climbing here for a second, because I learned a lot from the guides there, you know, and I'm sure this is similar to your coaching work, but one of the things, there are a couple things that they did to help people climb the mountain.

You know, they were really good at assessing people's states, physical and mental states, you know, they could help, they could kind of tell whether you just needed a nudge, or whether you needed to go back. One of my favorite stories was, I did a five-day expedition on Mount Rainier, and one of the clients on the climb, you know, we were all packing our gear bags up, and it was five days, we had heavy backpacks, 55-pound backpacks, and he was nowhere to be found, and he wanders back in wearing denim shorts, which are sort of a hard thing to wear on a mountain climb, eating a chili dog, and he said his mission was to experience the most painful experience of his life. I was like, oh gosh, you know, you can kind of tell that's not going to go very well, and you know, it was a five-day climb, he made it three hours, and you know, every time we stopped for a break, you know, he got, like, the first time he got caught up by the time we were done with the 20-minute break, the next time we never even saw him, and by the third time he turned back. I think, you know, helping people get ready is a great way to coach them.

The other thing is identifying what are objective risks versus subjective risks. So, if you're on a mountain, the objective risks are, you know, is there a lot of ice fall in an area? Is the weather pattern coming in?

You know, there are, you know, what are the states of the wands, the ladders over crevasses, you know, we can identify these risks and deal with them. The subjective risks are more, you know, harder to, you can't see in advance, you know, is somebody going to fall, and then you're going to have to deal with it, and if you can classify and coach people through and guide people through what are your objective risks, what are your subjective risks, how have you prepared, then you can break down that, the steps into easier to digest bits, and that's how you can help them through.

[Roger]

That's awesome. Yeah, breaking it down, it's like the old how do you eat the grande burrito one bite at a time. Right.

Yeah, and just breaking it down to smaller chunks, and then, yeah, and doing that with the risk as well, you know, being able to discern, you know, what's within our control, and what's outside of our control, and those things outside of our control, how much, you know, probability and impact, and we can geek out on the risk management side.

[Wynne]

Right.

[Roger]

But yeah, probably seeing someone up on the mountain in jean shorts and a chilly dog, probably like, yeah, you're probably better at the gorge listening to Dave Matthews Band.

[Wynne]

That's right. That's right. But what I love about that example was that they walked him back to the lodge.

And that's what's really good about, I think, about what we can do for each other as humans is, is to say, you didn't make it this time, and I'm going to walk you back. And I'm going to keep you company, because that's okay, that you didn't make it on this try. And I think our experience in doing that for others determines whether they'll try again.

[Roger]

Oh, and I love that sentence of you didn't make it on this try. You could have stopped it, you didn't make it.

[Wynne]

Right.

[Roger]

It's like the difference between no and not yet. Right. And getting back to that superpower of being, you know, of being a very good trier, knowing that you're going to get more bites at the apple.

Right. So speaking of bites of apples, who or what inspired you to have the superpower of being a very good trier?

[Wynne]

Yeah, I think, well, I would say that, great question. I think, obviously, the guides that I've climbed with have been, you know, great mentors in my life. I was raised by two brilliant and lovely parents, who always believes that we could do whatever we set our minds to, as long as we practiced.

And I think practice is a really good foundation for trying. And I'm going to kind of give another example of that. And it comes back to my experience of climbing mountains again, which is the first time that I tried that.

We climbed to Camp Muir, which is at 10,000 feet. Of course, the top is at 14,000 feet. And then a snowstorm came in.

So we couldn't leave Camp Muir while it was snowing. And there was some lightning involved. So instead of leaving at midnight for the summit, we didn't, we weren't ready to leave until 6am.

And the lead guide came in and said, if you want to try to get to the summit, and we're gonna have to go twice as fast in fresh snow, then get your gear together. So my friends and I got our stuff together. And we made it to 11,000 feet before we quit.

You know, I think out of the 24 climbers on that only three made it to the top. Because we were going twice as fast. And I learned, you know, practice, you can get ready to climb a mountain and probably make it and do okay.

Or you can get ready at a second level, which is to have a little extra in the tank. And, and to have fun with it. So when this came to this last New Year's Day, I told my kids who are six and 10, my kids, you guys want to climb Tiger Mountain with me on New Year's Day.

They were like, yeah, and I'm like, okay, we've got to practice. Because it's you know, their little young legs probably could make it up 2000 feet up Tiger Mountain, but they weren't gonna have any fun. Right?

Unless you practice. So I think that that's another great story about, you know, how to keep trying is to create that foundation and help others create that foundation to have a little more in the tank. Have you climbed Rainier?

[Roger]

No, I haven't. I have gone, gone up to paradise and gone snowshoeing around on a beautiful sunny day, only to have like, within minutes at a cloud came in and all of a sudden, it's like, oh, yeah. Where?

Where do we go? Right. And there was a little bit of panic.

Yeah. But have not have not climbed Rainier. Yeah.

I want to I don't know if the story is true, but I'm not going to let truth get in the way of a good story. I was reading a book when we first moved here. I was reading a book about Rainier.

And it was a fascinating book. I forgot the name of the title, but it talks about a conversation between John Muir and Teddy Roosevelt. And I believe they talked to they they had this conversation at the summit of Rainier.

Again, that's the part I don't know if it's true. But one of them was talking about being at the summit. The other one said, I think there's a lot more joy to be had at the bottom of this mountain than the top.

And, you know, that's kind of stuck with me around like, like, I've done hard things. My equivalent was running marathons and qualifying for the Boston Marathon.

[Wynne]

Oh, wow.

[Roger]

Yeah. Yeah, there was there was like five attempts and one one qualifying run to make it happen. But each of those qualifiers was that experience of, OK, not today.

Right. But maybe next time.

[Wynne]

Right. Right. And that practice to get your level up to the next.

I mean, each one adds nothing is wasted.

[Roger]

If we have that perspective.

[Wynne]

Yeah.

[Roger]

When what do you know to be true about being a very good trier?

[Wynne]

I'd love the name of your podcast because it's what you know to be true. It's not what you think to be true. It's what you know.

[Roger]

And it's not it's not even what is true.

[Wynne]

Right. Right. It's such a that complexity of the question is and the way that you phrase it is so good that trying is fundamental to growing and we never stop.

[Roger]

Well, that's a choice, isn't it? It's not only do we you know, when do we stop growing overall, but in which which directions? And I think some people, you know, stop really early because the important things get hard.

Growth is hard. Growth is outside of that comfort zone, you know, to your point about maybe going double speed to be able to have extra in the tank. That can feel hard.

Yeah, I love that. So what did you used to believe to be true, but then learned is no longer true about being a very good, very good super trier. Right.

[Wynne]

Super trier.

[Roger]

You got a cape now. You're super trier.

[Wynne]

I love it. I love it. You have to know when to stop.

That was something that I didn't know. And that kind of goes to that question. Are we talking about persistence instead of trying?

There are times when you do, you know, have to say, you know, this either this isn't my my goal anymore. It's you know, you have to know that difference between is this just hard temporarily or is this not where my path any longer? And that's really hard.

That's really hard to do that. Another thing that I've learned is that I didn't understand that we all have a different tolerance for trying. And, you know, I have a lot of energy.

So, you know, that plays in whether you have the energy, your tolerance for risk, everybody's is different. And this seems so simple now that I'm saying it, but it took me a long time to figure that out. Also, just that fundamental belief, that confidence that you that you can try that differs in everybody.

[Roger]

I'm curious now, do you tend to gravitate towards people with a higher threshold for trying? Like you're mentioning that the mountain climbing guides, I'm sure, have a high threshold for trying. But other areas in your life, do you tend to gravitate towards them because of the shared superpower and also the inspiration?

[Wynne]

Yeah, I think so. I think I probably gravitate towards people with high energy, too. I mean, I think people who are like, okay, yes, you know, I think yes, people would probably be who I gravitate to, you know, that the default to like, oh, are you going to do that?

Yes.

[Roger]

Yeah, yeah, that willingness to try and not be held down by real or, you know, imaginary. Boundaries and borders. Interesting.

So what's next for you in your superpower of being a very good trier?

[Wynne]

Oh, gosh, that's a good, good question. You know, I just went to my daughter is going to Middle School. That opened my eyes of this is sort of the next phase of parenting. They get out of that safe little cocoon of elementary school and our journey as parents, as you well know, changes so much over a lifetime of what we need to do for them, what we need to allow them to do. And as you said, trying is, we try different things, and then we look back and see, you know, how did I screw that up?

I guess I'm taking the long way. I'm taking the scenic route to, you know, I got to keep figuring out how to grow and let those people around me grow and coach young people in trying their next thing.

[Roger]

When our kids were about that age, someone recommended to me a book called Staying Connected with Your Teenager. And it uses the analogy of up until the time they hit puberty, you are their manager. Once they hit puberty, you are now their, you hope to be, their trusted advisor.

Because they will go and seek opinions and advice from a lot of different sources. And so this talks about how to make that shift from, again, organizing the play dates. You know, they come home from school, and you have that long conversation about what happened, and you can provide some advice, and they're going to, you know, likely go do it, to they come home, and you ask how the day was, and it's like, okay, and then you hear the door shut.

So it's like little tips in that book were beautiful about like when your kid goes out on a Friday night at 7 a.m. and then they are 7 p.m. and they come home at whatever time they have to come home, that's the time for you to take a nap. Because when they come back, they're going to be used to talking at a million miles an hour with their friends, and they're probably going to still want to talk. That's the time to be able to ask them questions and learn how things went and hear.

And then the idea of when you're, you know, as a parent, no kid wants to hear advice from their parents, but how can you, you know, provide perspectives? How can you share ideas of like, okay, you might want to swing from the ceiling fan, but in my experience, when you put a lot of weight on that ceiling fan, it's going to fall down, it's going to rip the ceiling. I don't know.

If you want to try it, go for it. But no, there's risk.

[Wynne]

Yeah. Yes. I love that because I've written down that recommendation because it's perfect because I think that's what's next for me is that I'm going to have to step up my game as a coach for trying.

And you've just given me a great tool in my tool set.

[Roger]

And at the same time, you want them, you know, their growth, you know, their journey is that, you know, giving self permission to go and try. So you can't put up all the barbed wire and tall fences and, you know, have a lot of no's because it's such a wonderful, amazing time to go discover who they are.

[Wynne]

Which brings it full circle back to curiosity, which is what you said earlier. And that matches, right? I mean, that's what kids bring to us so much is that vibrant curiosity.

[Roger]

It's so beautiful in the scene that in youth and at this time, it gets hard because you're more likely to see it in your kids' friends than your own kids. But, you know, who knows? Every kid's different.

Sometimes you get to see it. Sometimes you don't. And everyone's on their journey.

[Wynne]

It's so true. We just need to keep walking us back to base camp when so we get ready for the next try.

[Roger]

I love that summation. That sounded like a pun. Anyway.

[Wynne]

I love it.

[Roger]

I'll be here all week. Drive home safe. Wyn, thank you so much.

This has been such a generative conversation. I love this idea of being a very good trier of that first tip of try one thing. If it doesn't work, undo that thing.

Try the next thing. As well as understanding, you know, when is it enough to say, okay, this time it ain't going to work and I can turn around. I can go back before something, you know, more problems or catastrophic happens.

How do I turn around? What's the time to turn around? How do I, you know, set that early, make that agreement, follow through and think of it as, okay, it didn't happen this time.

But I will, I will get to try again.

[Wynne]

Right.

[Roger]

So thank you for sharing.

[Wynne]

Wonderful. Wonderful to be here. Thank you for your time.

[Roger]

Okay. Take care. Bye-bye.

Thank you all for being in this conversation with us, and thank you, Wynne, for sharing with us how to be a good tryer too.
 
 

The question I’m asking myself now after the conversation is: Where am I trying to do big things, when I should be breaking them up into small and smart experiments?  

What Do You Know To Be True? is a Three Blue Pens production. I’m your host, Roger Kastner. 

We are recording on the ancestral lands of the Duwamish and Suquamish people. 

To discover the ancestral lands of the indigenous people whose land you may be on, go to native-lands.ca

Be well, my friends, and, love you, mean it!