From Luxury Timepieces to Time Sovereignty: Re-Evaluating Your Corporate Success

Are you an overachieving director, VP, or enterprise executive who has accumulated the traditional markers of success—the luxury watches, the high-end gifts, the big compensation packages—yet feels a persistent pull toward owning more of your actual time?
In this deeply personal solo episode, host Billy Keels reflects on his 26-year corporate trajectory, including 17 years in the enterprise software space. Billy breaks down the distinct seasons every high performer navigates: from the early phase of working relentless hours to validate success through luxury material purchases like Cartier timepieces, to the realization that physical items cannot match the value of cash-flowing assets and true schedule sovereignty. Discover why feeling like you're "being sent to the principal's office" when requesting PTO is a major signal that your priorities have evolved, and learn how to intentionally transition from acquiring things to engineering life-changing experiences and lasting memories with the people who matter most.
🚀 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:
- How do an executive's definitions of success naturally evolve across different career seasons?
- Why do luxury status symbols eventually lose their appeal for mature high performers?
- What does feeling anxious about asking for PTO reveal about your current schedule autonomy?
- How can corporate professionals pivot their focus from material accumulation to asset-backed experiences?
- What are the foundational steps to gaining control over both your time capital and income generation?
⏱️ Episode Chapters:
- 00:00 - A Conversation in Barcelona: Reflecting on Luxury Timepieces and Corporate Trajectory
- 01:10 - The Early Phase: Compensating for the Grind with Cartier and Tiffany Purchases
- 02:25 - The Mindset Shift: Realizing You Can Only Wear One Watch at a Time
- 03:15 - Shifting Priorities: From Buying Toys to Creating Global Family Experiences
- 04:30 - You Are Not Crazy: Normalizing the Transition to Time Sovereignty
- 05:40 - The Chesapeake Bay Story: Capturing Unforgettable Moments with Family
- 06:50 - The Principal's Office Paradox: Why Asking Permission for Time Away Signals a Need for Change
- 08:10 - Taking Intention Action: Owning Both Income Production and Time Control
- 09:15 - Moving From Theory to Practice 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
There comes a moment in every high-performing senior leader's career where buying another luxury watch or status symbol completely loses its shine. In this episode, I reveal how I shifted from collecting physical items to building independent assets that truly funded more ability to have control over my time and create unforgettable family experiences. 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.
Billy Keels 0:50
So I had a good friend of mine who was over at the flat here, over at my flat in Barcelona, not too long ago, and we started talking about timepieces or watches, whatever, right? And so it made me think about a lot of my corporate trajectory and the things that happened during corporate, which was 26 years. And I really, really enjoyed my corporate experience. I was very, very fortunate to spend 21 of those 26 years in the high tech space, and specifically 16, let's call it 17 of those in the enterprise software space, which is just an amazing bubble, right? And so, as I as we were having this conversation, it really made me reflect on this moment in my life, and I was thinking about my corporate career and really how it took on these different phases. And there was a moment in my corporate career where I was so focused early on. It was this pre-marriage, pre-kids, and it was like coming from the background that I come back, that I came from, with watching my parents work two jobs most of the time, and just really got the great grades and done some traveling around the world, and and was on the track to do all the things that I was supposed to do from other people, right? Their version of success. I'm not even going to go down that rabbit hole right now. I'm going to stay here, and I started recognizing that it was one of the phases, like seasons of my life, where it was let's just continue to stay very, very busy at work and continue to produce. Now, I really like to stay productive, busy not so much. I like to stay productive because then that means something's being produced of quality on the other side, but what I also realize is that because of the way that I grew up, there was a moment that it was really important for me to be able to to compensate for the the time that I was putting in, and I you know I remember specifically because we're talking about these timepieces, we're talking about watches. Like there was a moment in my life where the things that I thought were the most important was you know taking my my girlfriend, who eventually became my wife, taking her to Tiffany or buying stuff from Tiffany, and then I got to a point in my life where I was like, "Hey, listen, everybody else seems to be wearing really nice timepieces. I call them watches, timepieces. And so I was like, "I need one. And so then I got one, and then I needed another one, and then I was realizing, like, what these Cartiers, what are they doing? Like, you can only wear one at a time. At least this was my mentality, and I thought to myself, "Well, in this, like the other one that's here, like doesn't that couldn't I actually use that to buy an asset that produces cash? But that, once again, I'm not going to go down that rabbit hole. But it was just the things that were important to me at that moment in time. I felt those were the things that I was doing to show that I could and that I cared, right? And at the at the same time, over time, I started realizing that was one phase, and then there was the phase of marriage, and then there was the phase of having kids. And I realized like this is really important to be able to be present for my kids, for my family, and also be able to produce in my role, because I was providing the life and the lifestyle that I was giving to my family, right, and to myself, and and being able to provide, but also with the kids, it was like, hey, listen, you know, let's you go and you get them the toys, and you get them. The eventually they got older and the PlayStation. I will say it's one of the benefits of living in Europe because there's not as much space, so you don't you don't have as much stuff. Once again, let me come back. I don't know why I feel feel like really talking about a lot of different things today.
Billy Keels 4:07
I will say that when you get to that point, it was really as especially as my kids got older, I started focusing less on the things that I could buy for them and for other people, and there was this shift to really say, you know what? Yes, I'm present. Yes, I'm here, and I'm taking my kids to school. I'm back from my my business meetings, and I'm picking them up from school. And yes, there were the special weekends where we would go away. I think about this weekend. We went to Bergamo in Italy, or just outside of the area where we lived in in Barcelona, or trips to the United States, and it became more about like how do I do more and more of these things? How is it going from creating things and buying things and stuff to creating more and more the experiences? The reason I share this is because I recognize it happened in me, in in for me, and if it happened in me and for me, but at the time I didn't have a reference point. I didn't have anybody to be like, okay, well, yeah, I'm not crazy because it happened for him too or for her too. And I realize that this platform allows me to share with you because I want you to recognize that you are not alone. If you used to want to buy all the stuff, and now you want to create more experiences, I would say that that's a part of the process. It's a part of the season of life that you're in. It should also tell you something to where your priorities are. Owning more of your time to be able to do with it as you like, invest it with your family, with your friends, with your loved ones, to be there, to be present. Listen to that, you know. And I remember it goes. I go back to summer of 2022, and it was one of the greatest times. I remember going on a trip with just me and my boys, or we were in the states, but we went ahead, and we had this opportunity to go down visit one of my buddies, and that has actually even been on the show a couple times, but went to go visit him, his kids, and we're there in the Chesapeake Bay, and we're like at a at a college and overlooking the Chesapeake Bay and out on boats and being able to do things and create these memories together that we continue to replicate at this point in time. But it's really now being able to focus and think about those specific moments-the lunches in the afternoon, or just sitting there on the dock, or looking at the jellyfish that were in the water, which kept us from actually getting in the water. Why am I sharing that? Well, the reason I'm sharing this is because as you go through your life in the season, recognize the season that you're in, if you find that you are wanting more control over your time, that you are wanting to be able to visit and not have to ask for personal time off because you know that you have your business under control, you know that you're going to over deliver, and it feels like you're going to the principal's office because you're asking for time away, you're not alone. It's just a matter of what can you do now. What can you? How can you be intentional so that you begin to own more of your time, have the type of control over assets that will allow you to also produce more income. Eventually, we'd like you to keep more income. That's a whole different thing. Not going to go there yet, but it's being able to ultimately create the experiences. in In order to do that, you need to own more of your time. And so, if you're feeling you're feeling that pull, you're feeling that tug to move in that direction, so that you are able to create something that will allow you to accomplish both of those things: owning the ability to produce income as well as produce more control over your time, you're not alone. You're not going crazy, absolutely not. I've been there, and that's why I'm sharing it with you.
Billy Keels 7:49
Because at the end of the day, as you begin to create more, it will allow you to be in a position where you are not just creating, but you're also capturing these moments in your mind with your loved ones that you really want to be able to do and do more of, and so that's the thing that I want for you as well, and that's why I'm sharing this with you because it's a part of your journey. It's a part of the season that you're in. Lean into it. Figure out what it's all about. Right? If you want to chat about it, you can find me. I'm pretty easy to find. It's what I do all the time, helping these senior leaders, helping other senior leaders just like you be able to navigate overachieving because that's just what you do, and also able to have more control over your time and ability to produce income predictably. Okay. If it's not you, and you know somebody who's used to focus a lot about the things, and now they want to focus on more experiences, they want to be able to have more time to do that. Share today's episode with them. It's a part of the process. It's a part of the journey. And then also show them that you care. Get on the phone, meet them somewhere, have a lunch, have your nice favorite beverage together. And while you're doing that, you're going from theory to practice. That's the whole point of this, so they can help you to continue to move forward. And while you're doing that, guess what? I'm going to be doing. I'll be right here because I love this stuff. I really love this stuff. Preparing for the next episode. So until then, go out and make it a great day. And thank you

