In my last episode, I had a great conversation with Holden Gallucia about trading security for fulfillment. Holden had started his career in programming, and that was a path he had chosen for stability after growing up watching professional and financial uncertainty within his family. But when his father passed away, that sense of safety wasn't enough anymore. He made the brave choice to pursue journalism following a creative instinct everyone else had seen in him long before he did. Hi, I'm Becky. Welcome to Short Story Long. In this podcast, we discuss ways you can integrate who you are into how you lead. Today I'm offering strategies for building your skills as a leader. Let's break down what's important about balancing a promise of stability with the fulfillment of what you really want. If you had a chance to listen to the episode with Holden, you might have been thinking about where are the moments that you're telling yourself about what you can and cannot do? To me, those limits likely sit at the intersection of risk and self-belief. Holden's story isn't just about changing careers. It's about rewriting the internal script that says, play it safe. As leaders, we meet people at the crossroads all the time. We coach team members who doubt themselves, who've learned that safety is more respectable than growth. What struck me was Holden's awareness that fear had shaped his choices long before he recognized it. His dad's passing didn't just spark courage. It stripped away the illusion that waiting for the right time is the same as being ready. The concepts of the right time and being ready are really subjective. Sometimes you need to make the change without it being the right time. And regardless of how ready you feel. For those of us who lead others, this episode is a mirror. It asks, how often do we hold our teams, ourselves, inside outdated definitions of success? It can be how often we mistake control for caring. Leading people means helping them weigh risk and possibility with honesty, not necessarily comfort. There are a few things I'd suggest leaders tune into for themselves and for their team members. One of the things that I was really struck by with Holden was that recognition of that hidden talent. Or at least it was hidden from him. A friend had told him, you clearly enjoy writing more than you do programming. And others also saw Holden's gift for writing. That's true for our teams too. We can spot patterns of curiosity, empathy, or creativity before someone else has the language to describe it, or even the confidence to name it. Great managers reflect potential back to people before they believe themselves. His friend said it, his dad said it. I mean, when is it that we start listening to people and what they say about us instead of dismissing it? How many times I've been in coaching conversations where someone will say to me, Well, yeah, but everybody knows that. It's obvious. And one of my common reframes is, it's only obvious when you know it. And you have to learn it before it's obvious. And with Holden, he recognized that he loved the reading and that he enjoyed the writing. He didn't see it as a secure job opportunity going forward. Some of these things are also coming back to it's not easy for everyone just because it's easy for you. And so when we're looking at people in front of us and we see all of this full buffet of skills that they have, we think it's obvious. Well, of course I can see it. It's right there. But as I just said, it's only obvious once you know. And so being able to share with your team members, no, really, you need to hear me. This is a special and unique skill that you have. Maybe that wouldn't have necessarily changed the course of Holden's educational pursuits at some point in time, but it might have helped him embrace the idea of writing as a career a little bit earlier. And I'm not even saying his timing was off. The way that you might be paying attention to this for yourself and the way that you might be expressing it to your team members is thinking about those times when you hear people saying something to you about what they admire about you, what they like about you, what they see you doing, and you don't accept it. Oh, that's not a thing. That's not that big of a deal. Anybody can do that. When you hear yourself saying that, check yourself and realize that not everyone can do everything. And some of these things that are really unique skills of yours, maybe you're the only one in the room who can do it. And if you see that in your team members, maybe it's worthwhile to tell them, it seems like you're the only one who has this skill in the team. We're really relying on you to do this thing. And that might grow into a direction of development and growth for them, even though it's already an existing strength. Naturally, though, it takes courage to make some of these decisions. I mean, I think about Holden saying that after his father had passed away, his thought was, I'd like to at least try pursuing my dream of writing and journalism. Holden's decision to pivot wasn't impulsive. It was intentional and courageous, but it wasn't impulsive. As leaders, modeling that same clarity matters. When you show that big decisions come from reflection, not reaction, you give others permission to do the same. And aside from the kind of courage that I have, courage doesn't have to mean recklessness. Yes, I leap before I look sometimes. Holden didn't. Holden stepped into this in a very thoughtful and aligned kind of way. If you've been listening to this podcast for a while, you know that I have taken a couple of really large steps without much looking forward. I don't always do that. Sometimes I'm actually going through a conscientious planning process before I take the next step. Holden really demonstrates that in the way that he approached this. It really meant aligning his choices with his values, even when there were no guarantees. He's in a programming role and he sees an opportunity to start a blog and start writing and creating that content marketing wheel for that particular organization. He did it as an extra. And sometimes we need to be able to step into those extra things where no one's really paying us more for doing that, because it's an opportunity for us to grow in the direction we choose to go. Because let's be real, why should they pay us for doing something where it's an investment in ourselves? And it may or may not, and in some ways, probably not, has a direct impact on the bottom line of the organization. Now, arguably, Holden's arg organization has continued to do that content marketing. So my guess is that they've decided that that's worth it. But that's where he got his start in terms of building that capability, building that understanding of what it would look like, what it would feel like to be able to do that kind of work. Because that's part of that decision-making process. We can think we'll love something. Then we jump and we realize, ew, this isn't nearly what I thought or hoped that it would be. Can I just turn back time and go back to where I was? And sometimes we can create these bridges from where we are to where we want to go so that if we decide to pivot and head straight back to where we started, we have that opportunity. What I would say is you always have the opportunity to say, this way doesn't work. Where am I going to go next instead? I have this whole habit of inverting a belief to test it out when I'm working with my clients. And so when I think about Holden's example of shifting and making some of these changes, it isn't necessarily what would he need to overcome? What would he need to face? It really became what is it that I can offer that I can do? So instead of this isn't my job, it becomes, how is it that I can offer something that isn't my job, but could be something that could be of some level of value to someone else? So at least they let me spend my time on it. And then you can ask, really, when you're thinking about your own experience, what would I offer to my employer in the direction that I would choose to go? And critically, how would I know if I were successful in doing the thing that I'm trying to learn or gain more experience in doing? Because that's really the measure of your success. And quite frankly, if you're volunteering your time to grow in a particular direction, you want to be able to measure whether or not that's successful. So maybe we call it courageous decision making with a measurement component that's tied into that. And sometimes fear builds up in the stories we build about why we can't and how the risks are simply too big. Maybe they are too big. Maybe they are. Sometimes our responsibilities today keep us from taking the huge risks going forward. But you can kind of take a page out of Holden's playbook and identify where you can get that slice of the dream instead of the whole pie. What it really does in his story and in his example in particular is really that demonstration of experimentation creating a semblance of safety. He did it not just in a bubble all by himself, not involving anybody else. What he did was ask his boss for an opportunity to expand beyond where he already was. His boss could have said no. I mean, honestly, maybe it wouldn't have made a lot of sense for his boss to say no, but we don't always make sense when we make some of these decisions. And so one of the things that's really important about this, especially when your team members are coming to you saying, Really, I want to learn how to do X, Y, and Z. Thinking about it in terms of how can we make it safe for them to experiment? Where if they mess it up, it's okay. And that might actually teach you about ways that you can create that safety and that experimentation for yourself as well. That permission to try something small, that's so critically important. Leaders can do the same by carving out safe ways for your employees to test some of those new skills. What they look like are low-stakes experiments that build confidence and uncover some of the capabilities far faster than some of the long-term planning. I'm all for development planning. I think that's a great idea. But you have to put a little teeth into it. You need to be able to allow people to take risks that might fail and not have some kind of dire consequence. His boss did something amazing. That simple exchange of, yeah, go ahead. Make sure you get your work done. But yes, go ahead and do that. That captures a leadership skill that's easy to miss. And that is this whole art of giving someone room to try with a fear of fallout. Holden didn't get any big promises. He wasn't going to get promoted, wasn't going to get a big job as a consequence of it. It was just permission for growth. And especially if you have an ambitious employee and you're saying, right, you can go ahead and do this. But we're going to agree and lock it in right now that this is actually an effort for your development and growth. And it may just lead to development and growth. It might also head you into a direction where you take on bigger things. But right now, what we're focused on is that growth and that development. There's not a single way to stretch yourself or to stretch some of your team members. But what you can do is take a look around and see what are the things that you could build that you actually need within your organization. Like I was talking about, sometimes mine were the big leaps into the unknown and trying something new. There wasn't a net for me, but I had accepted that. I knew that there was no net. And if you're talking to your employees and sharing with them, this is one of those no net experiences. I remember once when I was in corporate HR, I was applying for a next level within the organization type of responsibility. My boss pulled me along aside and said, you know, if if if you get this job and you mess it up, it's your job, right? Like it's your employment here. So recognize that if you take this role and it goes sideways, you might go sideways out the door. I'm not gonna lie, I thought that was a little harsh until I thought about it for a second and went, yeah, okay, that's actually true. I didn't get the role, which was fine. Um, and I do think that the person who was in that role ended up kind of going sideways and ended up going sideways out the door. So there was truth in that, and recognizing what level of risk that you're taking really helps you craft what it needs to look like for you or for your team member in terms of that safety. It can be a let's test it kind of mindset. You don't have to aim to be right, only aiming to see what works, lean into curiosity, and recognize when things aren't working so that you can course correct. So I talk about this a little bit in terms of micro experiments. You know, here in the in the story of Holden, it is write a few blog posts, see how they land, right? That's a micro experiment. If it goes wrong, okay, you pull them all back in. It's not that big of a thing. Or you leave them out there, but they do no harm. And the other thing that you can really focus on too is to celebrate the curiosity and not the outcome. So it's really thinking about what did you learn through this process, even if the outcome wasn't exactly what you wanted it to be. I listened to a podcast recently. They were interviewing Daniel Pink. If you haven't heard of Daniel Pink, one of the books that he's written that I think is really interesting is The Power of Regret. And I thought it was really interesting because he was talking about it as, and let me see if I can say this with any resemblance of the word, which was outcomism. Hey, look, I got it. So, with that, what he was talking about was we're always looking at what's the success of the outcome. And kind of going back to that idea of the courageous decision making as well. It's this idea of did you make a good decision? Well, you can't evaluate that based on what the outcome was. You don't always have, and most of the time you don't, have control over the outcome. And so with this, what you can be thinking about is in the safety of this experiment, what are we trying to learn rather than what are we trying to achieve? Because if we can learn something, then we were successful. And ironically, we achieved our goal. So set the right goal for the experiment and run the test. The other thing Holden had talked about was really this whole idea of balancing risk and responsibility. He was 22, single, no family to support. And he felt like that was the perfect place to go on an adventure with his career. And he framed that risk through the context of his world. Mature leadership requires that same discernment. Know the stakes before you leave and help your people calculate, not avoid those risks. Growth doesn't have to be all or nothing, it could be a series of informed bets. And my record is clear. I was older than Holden. Wait, I'm trying to do math. I think I was late 30s when I made, or even early 40s, when I made a leap. And I was married at the time. But the security in that was that my husband stayed in the United States when I went to Argentina. I was gone for six months. I could do anything, or so I thought, for six months. And then I would come home to the safety of my husband and my pets and my house and my life. And so that, too, even though it was a big leap with a short look, it was still one of those experiments where I could balance the risk and the responsibility because I had an exit clause if I needed it. It is harder to take a risk when you have more to lose. That doesn't mean you have to give up on the dream. Every situation is different. And sometimes it is that deep in the body knowing. It's the visceral response that Greg Stevens was talking about when he was thinking about going to Baylor. And it's that knowing that there's only one way to go. Sometimes it's creating that roadmap to get there. And sometimes it's just inching along and not necessarily knowing how all of those pieces are going to fit together. When you really think about it, in terms of balancing those risks and responsibilities, you want to be thinking about what is it that we want to protect, right? You're not in the business of really let's avoid age when we're talking to employees, right? But we don't want to get into their family situation. You don't want to be in their wallet. They don't want you in their wallet either. So it's an opportunity, though, for you to be thinking about what are they risking by taking a chance, by being part of a project and being really visible in front of senior leaders within the organization. What is the risk that they feel? It might be a perceived risk, but they still feel that risk. And if they fail and it goes sideways, do they go sideways out the door? Because they need to be understanding how big of a risk that was. Yeah, it kind of stung when my boss was like, be careful what you wish for here, Becky. But she was right. She was very right. And it was good for me to know and understand that risk, even though, of course, I kept on going forward trying to get the job that I probably wasn't well suited for in the first place. But that risk versus that responsibility needs to be balanced not only from your perspective as the leader, driving that for your team, but your team member has to understand that risk and make the decision to take that risk based upon the responsibilities they perceive for themselves. We can't force progress in something like this. They have to be willing partners when it comes to growth and development. One of the other things that I think is is really interesting about Holden's story is really his decision about why he went and why he shifted into journalism and writing. Because he really wanted to define success as a contribution and not control. He wanted to see the outcome and the impact. He wanted to do things for people. Success isn't always defined by position level or by pay. Very frequently, more frequently than not, it is based upon impact. Did what I tried to do actually make a difference? Holden's shift to journalism was absolutely grounded in contribution. He wanted to be helping others make better decisions. For most of his early life, he was focused on control. Control over his income, his security, his outcomes. He came from a place where uncertainty felt dangerous because sometimes it was. He moved to meaning. He chose journalism because it allowed him to help others make better decisions and to leave something of value behind. His success was no longer about what he could contain. It became about what he could contribute. From a leadership lens, that's the same pivot every strong people manager eventually has to make. Early career success is about personal mastery, your competence, your clarity, your results. Once you're responsible for others, control becomes a trap. You can't own everyone's output, emotions, or their choices. What you can own is the environment you create and the impact your team has together. When you think about personal certainty, it sounds like I know the answer. We hit the target I set, nothing went wrong. Knowledge means security, achieving the goal, security, nothing went wrong, security and control. Those measures keep you safe, but sometimes they'll keep you small. And they're rooted in predictability and ego protection. When you start thinking about the environment, you start thinking about collective benefit. And that's where you start hearing things like the team grew in confidence and capability, or work improves something tangible for others. Or, you know, hey, we learned something that will serve us next time. We might have done a full-on faceplant this time, but we learned not to do that next time. Those measures are broader, they're riskier, and they're harder to quantify. But they're what build trust, loyalty, and resilience in a team. And leaders who measure success by collective benefit and not that personal certainty and control, they cultivate purpose and engagement in their teams. So, how can you build this? Here's your skill builder challenge if you choose to accept it. I really want you to think about your risk threshold. And I want you to be able to name it. And by that I mean just write down what acceptable risk looks like for you as a leader. Knowing that boundary helps you support others through their boundaries. And you might be thinking about what does your team need to understand about that threshold of yours so that they understand what your risk threshold is and they can use that as a measurement for how they approach you and how they pitch you on the things that they want to do. Saves a lot of time for everybody. The other thing and the other angle on that is what change might you consider to shift that limit? Where is it that maybe you'll ease a little bit into discomfort and get away from that limit that you've been placing, let's face it, on yourself. You know, overall, Holden's journey was a reminder that safety and fulfillment aren't opposites. They're partners when we define them consciously. The comfort of certainty is temporary. The confidence we build from growth lasts. As a people leader, your job isn't to keep everyone comfortable. It's to help them feel capable when comfort fades. When you lead, like hold and learn to live, curious, courageous, and open to the next chapter before you know how it ends. Sometimes it's also about leading yourself. Where are your hidden talents? The ones others see and you undervalue. As you support others creating experiments and balancing the risks, take a look at your own journey. Where have you learned and what's coming next? Leadership is practiced in motion. You can step forward even if the path isn't fully mapped. When it's too scary to take a leap, find a small step that you are willing to take. Those baby steps add up to be the foundation of what looks like a leap in hindsight. Thanks for listening. If you found this episode helpful, share it with someone who could benefit from it. Until next time, I'm Becky Fraser, reminding you to integrate who you are with how you lead. Okay, bye.