Wild Courage

Todd Henry [00:00:02]:
In 1999, the job search website Monster.com launched a brilliant ad during the super bowl called When I Grow Up. The ad featured a series of kids sharing their dreams, only with a twist. When I grow up, I want to file all day long. I want to claw my way up to middle management. I want to be replaced on a whim. I want to have a brown nose. I want to be a yes man. The ad finishes by asking a simple question.

Todd Henry [00:00:29]:
What did you want to be now? The subtext of the question, of course, is that you didn't set out for any of these roles when you were young, so why would you settle for one now? Now listen, Some would argue that the world is much more complicated than this commercial suggests. After all, kids are completely unaware of things like mortgages, organizational politics, and recessions. True, but the fact remains that many people who start out with promise end up settling along the way for something less. They may rationalize that it's because of external forces, but the reality is that many of them sold themselves out in small ways over time until they could no longer find a way back. No one charts a course for mediocrity, yet it's still a destination of choice. It's chosen in small ways over time, and those small, seemingly tiny, inconsequential decisions accumulate until they result in a state of crisis. And by that point, making a change feels overwhelming. Now, please note that mediocrity doesn't mean doing poor work or failing to achieve success in your career.

Todd Henry [00:01:33]:
You can appear very successful to others, but know deep down that you're settling at the same time. You might seem outwardly unimpressive to others, yet be maximizing your abilities. Mediocrity is thoroughly subjective and relative. The key to avoiding the slippery slope isn't just to work harder and longer. It's to ensure that you are intentionally disrupting your own work rather than circling the wagons and protecting the ground you've already taken. That's a section from my 2013 book called Die Empty. The chapter's called the Siren Song of Mediocrity, and I often give speeches to companies about this topic of mediocrity and how we can easily slip into it without even knowing. And from the outside, it looks like everything is fine.

Todd Henry [00:02:17]:
We're hitting our numbers, everybody's delivering on their objectives. You know, we're all hitting our marks. But we know that we've settled in. We know that we're in a place of stasis, that we're not growing anymore. We're just protecting the ground We've already taken this word. Mediocrity in its original form comes from two words. The word medius meaning middle, and the word okras meaning rugged mountain. So to be mediocre literally means to stop halfway up a rugged mountain, to stop halfway to your objective, to get halfway to where you originally set out to go and say, eh, close enough.

Todd Henry [00:02:48]:
I'm going to settle in. Why do so many bright, sharp, talented, amazing, ambitious creative professionals eventually settle? Medias ocris after all, it's not like we want that. It's not like we choose that. Yet that's often where we end up. And the key ingredient to overcoming that is courage. Courage to do what we suspect we should do, yet we don't really want to do. Because fear often whispers in our ear. Fear often comes disguised as wisdom.

Todd Henry [00:03:27]:
It says things like, wouldn't it be better if. Or maybe you should? On today's show, we have someone who's going to share with us some ideas about how we can overcome those fears and begin to act more meaningfully with wild courage in our life and in our work. This is Daily Creative, a show for creative professionals and leaders who want to be brave, focused and brilliant every day. My name is Todd Henry. Welcome to the show.

Jenny Wood [00:03:55]:
I spent three years doing research at Harvard Business School. I then basically spent my entire career up till now at Google. 18 years, from 2006 to 2000. Well, I just left very recently, grew from entry level to executive ran an operations team that helped drive billions that sat between sales and engineering, and then founded what became one of Google's largest career programs in history as a passion project called Own youn Care. Jenny Wood AUTHOR of Wild Courage Go after what you want and get it.

Todd Henry [00:04:24]:
Jenny and I met at a small retreat of authors and entrepreneurs in Atlanta a few months ago. And I was kind of blown away by her story. Like many authors, the seeds of her book originated in a singular, life changing moment.

Jenny Wood [00:04:37]:
This whole thing of wild courage started when I was riding the subway home from work in 2011. There was a really attractive guy standing about 20ft away from me. I wanted to talk to him. I was too scared. I was living in fear. Fear of uncertainty, fear of failure, fear of judgment of others, which are three fears that wild courage helps you overcome. And. And I made a deal with the universe.

Jenny Wood [00:05:00]:
I said, if he gets off at my stop, then maybe I'll try to talk to him. And if not, then it's not meant to be. And he gets off at the next stop, Todd, which is not my stop. And then all of a sudden, this wave of wild courage washes over me and practically pushes me out of my subway seat and pushes me off the train. As I chase after him, tap him on the shoulder and say, excuse me, I'm sorry to bother you. You're wearing gloves, so I can't tell if you're wearing a wedding ring, but in the event that you're not married, you were on my subway and I thought you were cute. Any chance I could give you my business card? And then he takes my card, we go on a date a week later, we get married three years after that, and we've now been married happily for 11 years with two little hooligans, ages 7 and 9. So that was the moment that wild courage became a habit for me and I started applying it to every area of my life.

Jenny Wood [00:05:50]:
Relationships, goals, work, et cetera.

Todd Henry [00:05:53]:
It's funny how moments like this can change our perspective on what life really is. Steve Jobs, the co founder of Apple, once famously stated in an interview, everything around you you call life was made up by people who are no smarter than you. And you can change it, you can influence it, you can build your own things that other people can use. When you begin to realize that agency is a real thing, that you can just act on the world and make things happen, it kind of shifts your whole perspective on what's possible. Jenny coined the phrase wild courage to describe chasing after things that others might deem crazy.

Jenny Wood [00:06:30]:
By the time I started working on this concept of wild courage, I had trained tens of thousands of Google executives, non executives, people inside and outside the company, directly or indirectly on success, leadership, influence, achievement, going after their goals. And the same theme kept coming up, those same darn fears that I felt on the subway that day. Fear of failure, fear of uncertainty, fear of judgment of others. So wild courage is the process of feeling that fear and taking action anyway.

Todd Henry [00:06:58]:
Now, most books in the genre of wild courage will offer up an array of platitudes or fundamental positive attributes that they want you to aspire to. Be right, be bold, be empathetic, be single minded. But that's not the approach that Jenny took. In fact, she found a much more practical and I think, realistic way to describe what it looks like to exhibit wild courage. In fact, she found that it's often the simplistic, platitude laden advice that stands in the way of people exhibiting courage. They're so afraid of getting it wrong. So she instead framed her ideas around things you normally wouldn't aspire to be, but that when framed in the right way are actually pretty good advice. For example, she encourages people to be manipulative, but that doesn't mean exactly what you think.

Todd Henry [00:07:45]:
Here's Jenny to explain.

Jenny Wood [00:07:47]:
I wrote a handwritten note to my agent when I started working with her saying how grateful I was to be working with her. She's got the biggest names in this industry, like, the biggest. And I said, you know, I did that because a. I was excited to show gratitude, but it was a little bit, let's call it manipulative in terms of wanting to influence you, wanting to build a relationship with you, wanting to invest in this relationship so that you gave me extra time. And when I'm this teeny, teeny, teeny tiny fish in your very big, important pond. And so I was like, yeah, I had a little bit of an ulterior motive with that thoughtful handwritten note. And so that's a tiny little moment I would call healthily manipulative or thoughtfully manipulative. Right.

Jenny Wood [00:08:29]:
It's. It's the courage to influence others, to build influence through empathy. Because, you know, whether you're selling a product, an idea, yourself, your ability to win friends and allies and supporters, like, is all about mutual benefit. So figure out what people want and, and go help them get it right. And oftentimes people want to feel valued. At the core of so many people's existence and work and life and relationships is wanting to feel value valued. It's evolutionary psychology. Right.

Jenny Wood [00:08:56]:
And so this is my twist on these very common terms.

Todd Henry [00:08:59]:
When you talked about the note that you wrote to your agent, right. And I've. I've done the same thing before where it's like, yeah, I genuinely want to encourage. But also, like, like, for example, hey, let me send this helpful article to a client who's been reaching out, but we haven't done business together yet. But let me send this really helpful article to them to say, hey, this made me think of you and your organization. But really what I'm trying to do is, like, spark the conversation again and try to get the business right. I'm being helpful, but I'm also sort of like, trying to do something else. So when you talk about be manipulative, give us a sense of what that means and maybe a practical way that that could play out.

Jenny Wood [00:09:33]:
Here's the tool that I love. It's called woo with you. And you've teed me up perfectly accidentally. But let's say you send that article. You could write this email with every statement, every sentence starting with I. Let's say this person's name is Brian. Hi, Brian. I was thinking about you the other day.

Jenny Wood [00:09:50]:
I think you'd like this article. I really enjoyed this. I think there's, you know, something in here you might value. Now flip it. Woo with you. Okay. Have as many sentences as possible. Start with you.

Jenny Wood [00:10:02]:
Hey, Brian, you are always doing such great work in this industry. You, I think, are gonna find a lot of value in this article. You might particularly love the third section of this article because you are so skilled at empowering your audience. So in that second example, every single sentence started with you. So I call that woo with you. And it's a great way to build influence through empathy, to build lasting relationships, and to keep the focus on the other person. Call it manipulative in a healthy way. It works.

Todd Henry [00:10:30]:
So healthy and manipulation are not words that you expect to go together. In fact, be manipulative can sound like a permission slip to do all kinds of unethical things. I had to ask Jenny where she draws the line and how to curb the downsides of this advice.

Jenny Wood [00:10:46]:
Yeah, well, the line is that you don't want to harm anybody, including yourself, and you don't want to be deceitful. You don't want to lie. Those are the bright lines of it. And because that is such an obvious question that I would get with this work, right? Like, how do you know when you're taking it too far? I have offered for every single one of these nine traits, something called a trait trap. And that's exactly what you just said. How do you know when you're taking it too far? So, for example, obsessed is about a healthy work ethic. It's not grinding yourself into a workaholic pulp. Right.

Jenny Wood [00:11:16]:
Reckless is erring on the side of action and taking calculated risks. It's not jumping off a cliff without a parachute. Right.

Todd Henry [00:11:30]:
As I wrote about in my most recent book, the Brave Habit, many people mistake courage for bravado or the absence of fear. In reality, true courage is moving forward with intention and purpose, even when fear is present. It's not about eliminating uncertainty or doubt. It's about acknowledging them and choosing to act anyway. For example, when an artist shares a vulnerable piece of work, they aren't doing so because they have no fear of criticism. Rather, they share it because they understand the potential impact of their work matters more than their temporary discomfort. They feel the fear, but they don't let their fear be the deciding factor. They don't let fear, disguised as wisdom, curve their action.

Todd Henry [00:12:10]:
It's not about grand gestures or dramatic displays of fearlessness. Instead, it's about small, consistent actions taken in the face of uncertainty. It's about showing up day after day, making incremental progress toward what matters most, even when it feels uncomfortable. The paradox is that true courage often looks quiet from the outside. It's not the loud, brash confidence that demands attention, but rather the steady resolve that keeps you moving forward when everything inside you wants to retreat. This is the kind of courage that builds lasting change and meaningful work. And that's the kind of wild courage that Jenny hopes to inspire in readers of her book.

Jenny Wood [00:12:50]:
You gotta have the mindset of kicking imposter syndrome to the curb, right? It is a mindset. It is a. A commitment, a strategic commitment to recognize your own talent, to recognize your strengths. I encourage people to know their power assets. Two business skills, one soft skill. So, for example, my three power assets are building things from startup to scale, influencing stakeholders and people leadership. So think about what your strengths are, what your talents are, and then go share those with people shamelessly. Walk into your Thursday meeting with your boss and say, these are the three things I'm passionate about.

Jenny Wood [00:13:27]:
I would love to be assigned to projects that tap into these. And maybe there's one I'm not growing in and I'd love to grow in more. Or maybe one I feel like I should be sharing with the VP or your boss twice a year. Meet your boss's boss. So shamelessness is, you know, kind of the opposite of walking into a meeting and say, hey, this is a Shameless plug. But I created this spreadsheet and I think it might save you all 20 minutes. Shameless is embracing the fact that we should have no shame in what we do every day. We should say, hey, all, I'm proud of this spreadsheet I created.

Jenny Wood [00:13:58]:
It's going to save you all 20 minutes. Here's the link to it. I'm psyched for you for you to use it. That to me is like the shift from imposter syndrome or using language of shame or embarrassment or insecurity, or feeling like, oh, we have to feel insecure at work because that's cool. Or that's expected to, like, no. I've got this awesome stuff I'm working on and I can deliver in a way that's thoughtful, that's respectful, but that also shows that I take pride in my work.

Todd Henry [00:14:24]:
Jenny Wood's new book is available now. It's called Wild Courage. And if you want to learn more about her work, you can find her at itsjennywood.com that's I T S J-E-N-N-Y W O O-W.com I think this concept of wild courage is an important one. It's something that we should be thinking about. What is standing in the way of you taking action in meaningful ways to achieve what you want? Are there subversive forces that are coming against you? Are you listening to voices that you shouldn't be listening to? And more importantly, what will it look like for you to deploy courage today in the pursuit of your ambitions? If you'd like to hear our full interview, you can do so in the Daily Creative app at DailyCreative app. In the full interview, we talk about a couple of other strategies that you can deploy in your daily life and work. Of course, you can also hear of course you can also hear all of our interviews, the full archives, daily episodes, Q and A sessions, and much, much more@DailyCreative app. My name is Todd Henry.

Todd Henry [00:15:27]:
You can find me my work, my books, my speaking, and more@toddhenry.com until next time. May you be brave, focused and br.