How Executives Navigate New Life Seasons and Build Optionality

Are you an overachieving director, VP, or senior corporate leader experiencing a shift in your personal or professional life, feeling the persistent itch to build an asset you completely own?
In this reflective solo episode, host Billy Keels shares a powerful story from a family celebration along the Hudson Bay looking over the New York City skyline—a true "balcony moment" that crystallized why career designs must continuously adapt to life's changing seasons. Whether you're navigating new promotions, international moves, college-bound children, aging parents, or shifting compensation plans, your priorities naturally evolve. Drawing on the ancient wisdom of Heraclitus—the only constant in life is change—Billy breaks down why you do not need 100% of the answers or complete readiness to start building a side venture. Discover how to turn passive contemplation into intentional action, leverage your executive experience, and create a lifestyle where you show up to your career entirely by choice.
🚀 Want to make your corporate role optional? Grab your FREE copy of Billy's 3-Step Process eBook here: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm
📌 Questions Answered in This Episode:
- What is an executive "balcony moment" and how does it help you audit your current career season?
- How do shifting family milestones—from newborns to college-bound kids—redefine professional goals?
- Why is waiting to feel 100% ready the number one trap holding leaders back from starting an independent business?
- How does the principle "the only constant in life is change" apply to modern enterprise sales and strategy?
- What does it take to move from theoretical side-business ideas into concrete execution?
⏱️ Episode Chapters:
- 00:00 - Reflection on a Family Milestone: A Summer on the Hudson Bay
- 01:10 - The Evolving Phases of Life: Kids, College, Aging Parents, and Promotions
- 02:05 - The Balcony Moment: Looking Over NYC and Auditing the New Chapter
- 02:45 - Heraclitus and Constant Change: Aligning Your Career with Life Shifts
- 03:30 - Why You Don't Need to Be 100% Ready to Start Building Independent Assets
- 04:15 - Leaning In with Intention: Taking Action in Your Current Season
- 05:00 - Moving From Theory to Practice: Taking the Next Move Today
📘 About Billy Keels & Corporate Optionality
If you're a corporate executive who wants to make your role optional, learn how to achieve true control over your career and turn your corporate skills into personal assets.
With 26 years of experience in corporate sales leadership, Billy Keels achieved true optionality through multiple income streams. Today, he has helped dozens of executives build a predictable path to take control of their time and start living their ideal day.
This free ebook gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and starting to live your IDEAL day - today!
- Get the Free eBook: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm
- How to Leave a Review for The Going Long Podcast: https://youtu.be/qfRqLVcf8UI
Be sure to connect with Billy:
- Website: https://www.billykeels.com
- YouTube: https://www.youtube.com/@billykeels
- LinkedIn: https://www.linkedin.com/in/billykeels
- Instagram: https://www.instagram.com/billykeels
- Facebook: https://www.facebook.com/BillyKeelsFanPage
- Twitter/X: https://www.twitter.com/billykeels
Episode Transcript
Billy Keels 0:00
Standing on a balcony overlooking New York City, I realize that every senior leader hits a turning point where a new season of life demands a new level of control over your schedule. You don't need to be 100% ready or have all the answers to start building your own assets. You just have to intentionally lean in. So let's dive in and let's get you to optionality. Today's episode is sponsored by Billy Keels Advisory Services. If you want to learn more about how to make your 99 optional, just go to makeitoptional.com. Once again, that's make itoptional.com.
Speaker 1 0:38
Helping you build freedom without losing your edge. This is the Going Long podcast with Billy Keels. I
Billy Keels 0:50
can't believe it's already been a year since my little brother got married. You know, for the second time, but it was last summer, and it was absolutely amazing. It was one of these things. It was on the, you know, we're on the east coast of the U.S. We're on the Hudson Bay, looking over into New York City. It was an absolutely spectacular day. You know, one of those days where the sky is just completely blue, like literally like this ocean blue, and we've got these big fluffy white clouds in the sky, and it was just you. It's warm enough to have your sunglasses on and the enough sun, and at the same time, it was just absolutely beautiful. You could be out in your t-shirt and all these other kinds of things, and it was such a beautiful day. And they were there for this beautiful celebration, and and it was even more exciting for me because the Buckeyes played, and that was at noon, and so it was a great kickoff. And so shouts out to you also too to my sister in law because that was great from a planning perspective. So let me not digress already so early in the episode, but what it was is that I started recognizing I really loved being able to participate in this new chapter. Right, there is a a new chapter in it. Having this new chapter in life, what it did is also reminded me about all of the different things that you go through in life, and as you're thinking about your your corporate role, and you're thinking about the responsibilities of your family, and whether it's you're in the phase of your children are just being born, or maybe your children are older, they're getting ready to go away to college, those are different moments in time. You're thinking about different things. You're making different decisions. Maybe you're you've had friends who have who've passed away, and that's given you a different respect for where you are today. The things that you can do. Maybe you have your parents that are aging. So many different phases of life really have you reflecting on what it is that you want to do in that moment, and you continue to make the decisions that you feel are the most appropriate for you at that time. And all of this crystallized. There was a one particular moment. The wedding celebration was absolutely fantastic. I even got a chance to get out there. I mean, I had my mom, my dad, my stepmom, my sister. Everybody was there. You know, nieces and nephews. It was really, really awesome. But there was a moment the day after, where I'm standing on the balcony of my brother and sister in laws, you know, their suite, and we're looking over the the Hudson Bay, looking over into New York City. It's absolutely gorgeous day once again, and we started talking about really, we had this like epiphany moment where we're thinking about okay, this new chapter of life, and really, what is it like? And being able to recognize so many different conversations that I have consistently, like literally on a weekly basis, with senior leaders in corporate that are thinking about, okay, well, where are you right now? Where what is this moment in your life? What is what are this what is this new chapter? And recognizing that as it's Heraclitus, I think it is that says the only constant in life is change. And so as you enter into a new phase. It's about being able to recognize what is this phase of life requiring of you. What what really needs to happen? You're always recognizing that these shifts are happening in your life, and whether it is you you've got a new promotion at the job, you are thinking about you've just gotten a new boss, or you're thinking about moving overseas internationally, something similar to what I did. There's a change in your compensation plan. There is a new raise on the rise, or that you recognize that this is a moment in your life where you're missing special moments. And you know what? You may even be thinking, I've really got this desire that I want to build something that I own because I know what I have here. It all goes back, right?
Billy Keels 4:49
And we continue to talk about that, but there are all these moments. There are all these different moments in time, and it's really important to recognize that each one of these moments brings about change. And the important part is. Be ready to continue to learn from the past, learn from others who've already been there, so that that can help to inform the decisions that you're making in this new phase of your life, based on the real roles and objectives, goals and objectives that you want to be able to work towards. Because none of it happens overnight. None of none of it happens by luck. There has to be intention. There has to be a moment when you decide that yes, what it is that you want in this phase of your life, this season of your life, that you're willing to be intentional about it. You're willing to lean in, even if you are not 100% ready. You are. You don't have all of the answers, but you know that that's the what is required for you in this season of your life. Now I think about it. It's like I said, it's already been a year, and I think about all of these wonderful things that you know. As I now see my my brother happily married and enjoying his life and the kids in college and working as well, and it's one of these things where you continue to see like he's got a family that loves him. He's got a family that continues to pour into him, continues to be there for him as he's there for for them as well in this new season of his life. Enjoying, there's always going to be changes, right? Just like that side business that you continue to think about, that you continue to want to to do something about. You're not 100 ready. You're trying to figure out exactly what is the next move. You got to lean into it because that's part of change. That's part of what happens. The question is: Is this the season for you to really lean in and be able to do that, because this is about your balcony moment. This is a moment that says, "Okay, this is a new season. What do I want out of this season? What am I willing to do in this season? Even if you don't have all of the answers, the thing is, it's time to lean in. And so, if it's not you, if you haven't been struggling with this season that you're in and deciding what is the next move, even when you're not 100% ready, think of all the greatness that is waiting, is achieving the goals. It's the learnings. This is the moment for you, and so if it's not you, if you know somebody who's trying to figure out what exactly what's happening in this season, why so many different changes, why do I keep having this voice calling over and over and over? I've got to scratch this itch. Share today's episode with them, because then this is going to be a way to really help them move forward, and then show them that it's not just about sharing; it's about caring. Give them a call. Get on the phone. Meet them for your favorite beverage-cold, hot. It doesn't matter. Just meet up and celebrate, because you're going from theory to practice. That's what this whole thing is about. It's about continuing to help you move forward. Because while you're doing that, guess where I'm going to be? I'm going to be right here because I love being right here, it's fantastic. Preparing for the next episode. So until then, go out and make it a great day. And thank you very, very much.

