He Visualized His Rich Life 5 Years Ago. Here's What Changed | Dan Pascone with Tom Kinneary | Ep 66

TL;DR

Tom Kinneary left a comfortable corporate seat in the natural gas industry to build a specialized advisory firm, and the path he took to think about work optionality is one of the most practical frameworks Dan has heard on the show. Tom reverse engineers his work-optional number the same way he reverse engineers commodity risk: define the end zone, calculate the delta between where you are and what the funding needs to look like, then back into what that requires each year in income and investment. Before any of that, he ran a visualization exercise five years ago that produced the seven pillars his weeks are still structured around today. This episode covers that exercise in full, how he thinks about building a business that eventually does not need him, and a genuinely useful primer on locking in your natural gas and energy rates before peak season hits.

KEY TAKEAWAYS

Tom Kinneary's approach to work optionality starts with the same discipline he applies to managing commodity risk: define the end zone with precision, calculate the delta between your current position and what you need, and back engineer exactly what that requires in annual income and investment. Most people treat work optionality as a vague goal. Tom treats it as a math problem with a specific answer.

The seven-pillar visualization exercise Tom ran five years ago is one of the most practical life design tools in this episode. Rather than listing general goals, he played out a specific day in his head from the moment he opened his eyes in the morning to the end of the evening, identified what was present in that day that he did not yet have, and organized those desires into seven pillars. His week is still structured around those seven pillars today, and the list has barely changed in five years.

Work optionality and business ownership are not the same thing. Tom is clear that the business currently depends on him operating it daily. The path to optionality runs through scale, hiring managers he trusts, and eventually stepping back to a passive investor or silent partner role. That is a multi-stage plan with clear milestones, not a single event.

Habit formation is the ground-level execution layer beneath visualization. Tom found that clear visualization without supporting habits produced incomplete results. The exercise forced him to identify which habits, both mental and physical, were either present or missing in the life he was designing, and to build routines around those gaps deliberately.

Natural gas rates in approximately 15 US states can be locked in through a competitive supply option. Most consumers do not know this option exists. For businesses especially, locking in a forward rate eliminates one variable from the budget and converts an unpredictable expense into a known one. The practical advice is to search your state name plus energy supply to find the relevant competitive supplier board.

The seasonal structure of Tom's business gives him a natural built-in prototype of work optionality. His peak season runs in winter, his shoulder months in spring and summer allow him to shift focus toward the other pillars of his rich life. For executives thinking about hybrid retirement, that seasonal rhythm is worth studying: it is work optionality in partial practice before the full financial architecture is in place.

KEY MOMENTS

  • 00:00 Dan opens: most high earners can tell you their number but very few can tell you what an actual Tuesday looks like on the other side of it, and that gap is why work optionality stays a vague idea instead of a design
  • 01:35 Tom Kinneary welcomed: founder of a specialized natural gas advisory firm, former corporate energy analyst and scheduler, now building toward work optionality through his own business
  • 02:50 Tom's path: from bartending at the Jersey Shore to customer service, energy analyst, supply analyst, scheduling and trading, to founding his own firm four to five years ago
  • 04:08 The pivot: identifying an underserved niche in retail natural gas risk management and making the decision to go out on his own despite the comfort and stability of a corporate salary
  • 05:52 Energy as a consumer topic: how to think about your natural gas and electricity supply options as a household or business, including the competitive supplier option available in approximately 15 states
  • 07:37 Energy rate strategy in 2026: how to think about locking in rates given oil and gas price volatility, the seasonal price curve, and the CFO-friendly benefit of eliminating one budget variable
  • 09:16 Work optionality as a design problem: how Tom thinks about the gap between where he is today and the life he is building toward, including how the business eventually exits his daily operation
  • 11:06 Building a business that does not need you: the stages from owner-operator to managers to passive investor or silent partner, and where Tom is in that progression today
  • 12:35 What a rich life looks like today: mental and physical health, seasonal flexibility in the business, and the ability to shift between work and the other pillars of a full life
  • 14:22 The identity tension after leaving corporate: the woman who could not not work, and what it means to design for what you want to do rather than what you feel like you should do
  • 15:18 The visualization exercise unpacked: how Tom played out a specific ideal day from morning to night, identified what was missing, and organized his desires into seven pillars that structure his weeks today
  • 17:25 What prompted the exercise and how long it took: the Jim Carrey check story, the power of repeating visualizations over multiple iterations, and keeping timestamped written logs to track how the picture changes over time
  • 19:37 Tangible action steps that came from the exercise: the iterative habit-building process, refining plans when goals are not achieved, and the role of both mental and physical habits in creating forward momentum
  • 21:18 The role of money in the grand plan: defining the end zone, calculating the delta, back engineering income and investment requirements, and the specific math that connects vision to execution
  • 23:13 Lightning round: mom's Italian meatballs with Pecorino Romano, the printing press, Principles by Ray Dalio, exercise and discipline from age 13, visiting Colombia as an adopted child, and advice to his younger self on self-love and independence from others' approval

EPISODE SUMMARY

Most high earners know their number. Very few can describe what an actual Tuesday looks like on the other side of it. That gap, between a number and a designed life, is what keeps work optionality as a vague aspiration instead of a real plan. Tom Kinneary is someone who closed that gap deliberately, and the framework he used to do it is worth unpacking in detail.

Tom spent years working his way up in the natural gas industry, from customer service to energy analyst to supply analyst to scheduling and trading, before identifying an underserved niche in retail natural gas risk management and founding his own advisory firm four to five years ago. The pivot from comfortable corporate salary to running his own business came with the familiar risks: no guaranteed income, no clients, a product that was not a certainty to find a market. What made the move viable was a very clear answer to the question of what he was building toward.

The visualization exercise Tom ran five years ago is the centerpiece of this episode. Rather than listing goals or intentions, he played out a specific ideal day in his head from the moment he opened his eyes in the morning to the end of the evening. He asked what he saw when he walked out of his room, how the morning progressed into early afternoon, late afternoon, and evening. Out of that process, he identified what was present in that imagined day that was missing from his current one, and organized those desires into seven pillars. His week is still structured around those pillars today, and the picture has barely changed in five years.

The money framework Tom describes is equally concrete. He defines the end zone precisely, meaning the age at which he wants work to be optional and the funding required to support that. He calculates the delta between his current position and that target. He then back engineers what that delta requires each year in income and invested capital, and what kinds of investments need to be in the portfolio to bridge the gap. It is the same discipline he applies to managing commodity risk in his business: no vague goals, specific numbers, clear reverse engineering.

Tom also addresses work optionality as a business design problem rather than a personal finance problem alone. The current business depends on him operating daily. The path to optionality runs through scale, hiring managers he trusts, and eventually stepping into a passive investor or silent partner role. That is a multi-stage transition with clear milestones, not a single event.

The episode also covers the energy side of Tom's expertise, specifically the competitive supplier option that exists in approximately 15 states that most consumers and business owners have never used. For anyone paying a utility bill without knowing there is a choice involved, this segment alone is worth the listen.

TRANSCRIPT

Dan Pascone (00:00): Hey, I'm Dan Pascone, CEO of Tailored Wealth and host of the Making Sense of Your Money podcast, where every conversation is built around one idea that your money is a tool to design and live your version of a rich life. You know, most high earners can tell you their number, but very few can tell you what an actual Tuesday looks like on the other side of it. And that gap is exactly why work optionality stays a vague idea instead of a design. So today I'm joined by Tom Kinneary who is the founder of a specialized natural gas advisory firm. And he left a comfortable corporate seat to build something that he could eventually step back from. We get into the visualization exercise he ran five years ago that produced the seven pillars his weeks are still structured around, how he reverse engineers the delta between where he is and what work optional actually costs. And because everybody here is an energy consumer, how to lock in your rates and take one variable off the table. So before we get into it, make sure you're subscribed on your favorite platform. And if the show is adding value, I'd really appreciate a quick review. It goes a long way. Thanks so much and enjoy the episode.

Dan Pascone (01:35): All right, Tom, thanks for joining the Making Sense of Your Money podcast. Excited to chat with you today, man.

Tom Kinneary (01:40): Likewise, thanks for inviting me. Appreciate it, Dan.

Dan Pascone (01:43): Yeah, you bet. So you and I have gotten to know each other a little bit and I'm excited to get into a few different things today. Number one, your profession is very interesting to me. And then number two, sort of your path and your journey and the way that you're building toward financial freedom is something that obviously I'm very passionate about and I know you are as well. So we'll get into both of those. But why don't you just start by giving us a high-level overview of who you are, your path to where you are today, and then ultimately what you do in your business.

Tom Kinneary (02:15): Yeah, appreciate that. So a little bit of background about myself. I'm originally from New Jersey, around the Jersey Shore area. Live in Stamford, Connecticut right now, but made this transition to the energy industry back in 2010-ish, 2011-ish. And so my company right now, my background right now, it's pretty much centered entirely around the natural gas commodity side. Very fun, at least to me it's fun.

Dan Pascone (02:50): Very, very cool. And I know you had done some corporate work in natural gas and energy previously. Tell us a little bit about what you did and then what ultimately caused you to pivot into running your own firm.

Tom Kinneary (03:04): Yeah, so I started kind of from the ground level up, sort of in the customer service type area of the business. And so it was a pivot for me to go from bartending at the Jersey Shore to working at an energy company. That was a big move for me. But just really became interested in how the energy industry works and how there's a lot of people that work to keep the lights on, to keep the heat on in the winter. So there's a lot of information to uncover there and just really became interested in it and kind of worked my way up from different levels in the company to energy analyst and supply analyst and then eventually scheduling and trading. And then about four or five years ago made the decision to pivot out on my own, because I saw that there was an area in the industry that really could use a little bit more of a specialized service. And that was my product offering initially when I started my own business.

Dan Pascone (04:00): Tell us a little bit about that specialized service. What is it at a high level? And then how did you identify that there was an opportunity there?

Tom Kinneary (04:08): Yeah, so it was a little bit of a chance, a little bit of a risk to take. Not exactly a hundred percent a shoe-in. So going from having a comfortable job and a good salary to being out there just saying, okay, now you're gonna work for yourself and you kind of gotta go out there and get clients. Yeah, it's certainly a risk there. But I was willing to take it because as you mentioned, and as I'm sure it is in most verticals, there are lots of niche areas of the business. And the commodity that I work particularly in, which is natural gas, is one where there's a very small segment downstream of production, which would be drilling and midstream, which is transportation. That's the retail sector. And it's niche enough such that someone who had a good handle on the ability to manage the risk that it entails, coming to market and offering a retail price to a retail customer, having the ability to manage that risk effectively was where I saw the skill was. And so to be able to recognize that during certain events in the past, certain winter events, there were a lot of companies that got hurt because they did not manage the risk appropriately. So I felt that was the missing piece, the knowledge to be able to manage tail risk. And to be able to survive these weather type, extreme weather type events. That was the skill and the missing piece that I saw. If I was able to bring some of that knowledge to some other firms, could I share that knowledge and use my expertise to then help them to help their business grow and help them survive these episodes? So that was the initial value pitch.

Dan Pascone (05:52): Got it. All right. We're gonna talk a little bit more about your career and your track and how you're thinking about the future and financial independence and work optionality, all that stuff. But first, before I forget, our audience, I think everybody really is a consumer of energy. So how do you get the best prices? How do you source energy at the consumer level?

Tom Kinneary (06:22): Yeah, at the consumer level, most people don't realize that in about fifteen states now across the United States, you actually have the option to choose who your energy supplier is. On the distribution side, it's pretty straightforward. Your local utility is the company that invested in the pipes and in the wires, so to speak. So they will have the regulated monopoly on the delivery of the energy, but the actual commodity itself, in many of these states, you're free to choose who supplies that energy to you. And so people don't realize that this opportunity offers you, especially on the commercial side, the ability to, for example, lock in your energy costs for a given forward time period, which allows you to budget. I know you're big into budgeting and planning. It allows you to budget for the future because at that point you know that your energy rate won't fluctuate. So it's an important choice that I would advise your listeners to at least look into. Do a Google search and Google in your state and energy supply and you'll probably get at least a forum or a board where you can choose among the various suppliers that are offering that competitive supply in your state.

Dan Pascone (07:37): Makes sense. And then with all that's gone on with oil in 2026, how do you suggest people think about locking in rates, with the idea that prices could be volatile in either direction?

Tom Kinneary (07:54): Yeah, as you've seen, prices at the pump have certainly been volatile recently. And there's a little bit of a correlation between gas and oil. Not as much as some may think. But in any event, you know, when you have the winter period, which is when, in my commodity, the prices tend to rise. And for electricity prices it would be in the summer. The reason is because in the winter you're using natural gas to heat your home through your boiler, and in the summer you're using electricity to power your air conditioner. So those are the peak time periods throughout the year when you're gonna wanna be cognizant of the fact that your rates may go up during these peak periods. That's just a supply and demand function. So to answer your question, you would wanna look at what price did I pay last year during winter, what price am I paying this year in the summer? And it especially comes down to the fact that if you want to budget, especially if you own an office space and you are using energy to power your office space in the summer and the winter, the CFO likes it when they can see what their budget is gonna be, especially if the price is locked in. So the only thing that matters at that point is how much you consume. You're eliminating one variable from the puzzle.

Dan Pascone (09:16): Yeah, that makes a lot of sense. All right. So let's get back to you now. How are you thinking about your business in the grand scheme of work optionality? How are you leveraging sort of what you're doing today and planning for this idea of work optionality?

Tom Kinneary (09:48): Yeah, work optionality is something that's big to me. The first time we got chatting, I referenced my whiteboard on the wall here. And I just took a lot of introspective time to understand what it is that I want out of my career and out of my life. And the number one thing, or at least one of the top three things, is gonna be the optionality to just have the flexibility to be able to choose what I wanna do each day. I know there's conversations probably in past episodes around passive income and things like that. But the idea is that you want to be earning money when you're not necessarily contributing or operating directly to the work or to the business. So to me, the work optionality is important because yeah, I do want to wake up every day and just say to myself, okay, today is whatever day, I'm gonna write my schedule in exactly how I want it to be. If I want to work, then it's my option to do so. But if I want to take off and spend it with friends or family or do other projects, I want to have the ability to do so. And after much thought on how to accomplish that, business building was the one main area that I wanted to focus on to say, okay, let's build a business, let's grow it, scale it, and then at some point have an exit plan to be able to then say, okay, I can now afford to take advantage of that optionality.

Dan Pascone (11:06): Yeah, that's interesting. I love your thoughts on that. Now with respect to your current business, are you able to kind of create work optionality within the business, or is the business solely reliant upon your work? Like in order for you to earn, do you have to work? Or are there ways that you can set up the business to hire people or put systems and policies in place so it's not solely reliant on your time?

Tom Kinneary (11:36): Currently the business is dependent on me operating it on a daily basis. But same nature of any business, at some point when you scale and you hire managers, and those managers hire direct reports and whatnot, you can find a way to not necessarily have to operate the business as much. And then eventually at some point when I have enough managers that I trust, you hand off the reins to them completely. And they're managing everything day to day. And I might only have to step in once every other week or so to kind of manage the most important affairs. And then eventually when I exit, at that point, okay, if I have an exit plan, do I want to then become a passive investor in a business similar to mine or different? And at that point, becoming a passive investor, someone or a silent partner essentially, is the point where I have the full freedom to be able to choose the full optionality of that work.

Dan Pascone (12:35): Got it. Very, very cool. I always ask everyone this. What does your version of a rich life look like today? And how do you see that potentially evolving into the future as you've spent a few years building this business?

Tom Kinneary (12:53): You know, today a rich life to me certainly looks like one where I feel good, both mentally and physically. Doesn't matter what business you have, and I'm sure many of your listeners have heard stories where you work your way up the corporate ladder and it's so tolling on you and you put in so many hours that it affects your physical and mental health. So today a rich life to me is certainly one where I have the ability to think clearly, feel good about myself, make it to the gym, exercise a couple times a week. And then to at least have some seasonality to my business, which fortunately it does. My peak season is in the winter and the off season is in the spring and summer. So during that downtime I certainly have more of that optionality that I'm looking for, and to be able to create that rich life, which is spending time with friends and family, working on projects I normally wouldn't have time for. And then in the future, the rich life is somewhat similar, just scaled down to the fact where maybe now it's the full optionality of how much input and how much time I want to spend operating into the core business itself. Really that full open landscape of being able to just have that full autonomous freedom as to what I'm doing each day.

Dan Pascone (14:22): Yeah, it's interesting. I spoke with a woman yesterday who had just left her corporate job and was considering what was next. Was she gonna do consulting or part-time work? Was she gonna go back to full-time work or was she gonna hang it up altogether? And she early on realized that she couldn't not work. She needed to be doing something, but she probably didn't want to go back to the corporate grind because she wanted to do a lot of the things that you just mentioned. So I'm curious, in the off-peak time, how do you think about your time? How do you structure your days so that you're available when you need to be available and you're doing the other stuff when you want to be doing it?

Tom Kinneary (15:18): Yeah, I understand the delineation between, you know, do you not want to work and could you not want to work? Or are you actually able to sit there and do nothing all day long? Some people can, some people can't. And each individual can decide that on their own. So to get back to your question, I structure my schedule, my day, my week, my month very particularly. And this all goes back to a lot of introspection that I think comes from having a clear picture in your head of what it means to live a rich life or a fruitful life. And an exercise that I did probably about five to six years ago was just to visualize in my head very clearly what it would look like each day if I was to wake up and have this rich, fruitful life which I'm desiring. And I was very clear about specific things. It wasn't just, I want to do this or this. It was, you know, when I open my eyes in my room in the morning, what do I see? When I walk out of the room, what do I see? What are the first things that I do in the morning? How does my day progress into the early afternoon, into the late afternoon, evening, all the way through? And I played this day out in my head very clearly. And from there, I was able to understand what are the things that I desire? And from there I made a very careful list. And I made that list around seven pillars. And so to answer your question, the days and the week and the month are essentially structured around each of those seven pillars that I have. So if two of the pillars revolve around work and it's some downtime in the summer, I can pivot towards the other four to five pillars and really block those in as to what I want to spend my time on in any given particular segment of the day.

Dan Pascone (17:25): All right, so I love this. We gotta dig a little bit deeper into this because I think the exercise you went through is so valuable. What prompted you to go through this exercise? How did you go about it? How long did it take and what kind of came out of it? Just walk us through the thought process behind going through this ideal day exercise.

Tom Kinneary (17:53): Yeah, I'm certainly big on visualization. There's definitely a lot of books and webinars and lectures where people will say the stronger you visualize something, the more likely it is to happen. The one story that comes to mind is Jim Carrey, who before he was an actor wrote himself a check for some seven-figure amount and said, this is the amount of money that I want to make. And he put that on his wall. So he was able to visualize very clearly what he wanted. And just throughout the books that I read, I learned that the power of visualization and the power of repeating thoughts in your head, it's almost like it trains your mind to think positively and visualize the outcome. And the more you can visualize it, the more you can kind of feel it. So that's sort of what prompted me to go about doing it. And then to work my way through it, it felt a little strange at first to kind of visualize things, but through several iterations, you're able to define more clearly a picture of what you want. And I've kept written logs of everything, timestamped, so I can kind of see how my visualization has changed throughout time. And it doesn't change very much. Over the last four to five years it's more or less stayed the same. Maybe I word it slightly differently, but it's more or less stayed the same. But again, it keeps me in a positive mindset, keeps me clear on the outcome and the goal. And then from those goals, I can certainly drill down towards the ground level and develop plans to achieve those goals.

Dan Pascone (19:37): Yeah, so that was going to be my next question for you. When you've done this visualization exercise, what tangible actions have come from it? Has there been anything that you've changed in your day-to-day? Has it affected how you spend your time? Has it affected how you interact with people?

Tom Kinneary (20:01): Well, one that comes to mind immediately is the fact that it can be very iterative. Because if you're making plans to achieve something and you don't achieve those goals or those plans, the iterative process comes out because if you're curious enough, you want to figure out what exactly did not work out that I intended. And so through further introspection, you can iterate through your plan and refine your plan. But one of the particular things that comes to mind is the fact that a lot of daily activity comes down to having good habits, both mental habits in the way you think and physical habits in the things that you do. So it forced me to realize, well, if I can't get this thing started or it keeps failing for a specific reason, let's revisit the habits. How can I curate better habits to develop these habit loops which allow you to gain momentum and further take steps forward as opposed to either being in the same spot or taking a step backwards? So habit forming was one of the main things I would say that this prompted me to develop.

Dan Pascone (21:18): Very, very cool. All right. Now, what role does money and finance play in your overall plan? So you've done this level of visualization. You have your roadmap for work optionality and eventually financial freedom. Tell us a little bit about the role that you feel money plays in your grand plan and how it impacts how you visualize things.

Tom Kinneary (21:46): It plays an important role because I'm always clearly defining the end zone. Meaning if I know that I want to retire or have at least the ability to take advantage of some work optionality, what age does that happen? How much funding do I have to be able to afford to say work part-time or no time? And what is my life expectancy? So you can kind of back engineer or back into it mathematically exactly what that financing looks like, what that funding looks like. And then you can calculate what the delta is between what you have today and what you need to have between then and there. And from there, once you know the delta, you can understand: okay, so what types of investments do I need to be able to grow to get to that level? What type of income do I need to be able to invest that amount each year, each quarter, whatever you want to call it. So when you break it down into a plan like that, you can just back engineer to pretty granularly how much I need to be earning now, how much I need to be investing now, and what sorts of types of investments do I need to be in to be able to get to that point where I have the funding which will then enable me to choose the work optionality or no work at all.

Dan Pascone (23:13): Very cool. I love it, Tom. Great stuff. Great foundation. Now we're gonna shift gears a little bit and get to know you a little bit more. We're gonna head into the lightning round. You ready?

Tom Kinneary (23:24): All right, I love it. I'm ready, let's do it.

Dan Pascone (23:31): All right, the only thing I always ask here is just give us the first thought that comes to your mind. Could be one word, could be a long drawn out thought. All right. One meal for the rest of your life. What is it?

Tom Kinneary (23:44): My mom's meatballs, hundred percent. She's been making them her whole life. They're Italian style. The recipe came from her grandmother. Hundred percent without any hesitation. But it has to be with a boatload of the Pecorino Romano grated cheese on top of it. Those two combined.

Dan Pascone (24:03): We could enjoy that together. I go back to my grandma's meatball and sauce recipes and still enjoy those to this day. All right, what's one tool or piece of technology other than your phone or your computer that you can't live without?

Tom Kinneary (24:11): The printing press.

Dan Pascone (24:27): Interesting. That's a good one.

Tom Kinneary (24:28): I just think that the compounding gains that you get from reading a book are just something that I don't know if I could live without. If the printing press wasn't invented, there'd be no books and you wouldn't be able to mass produce knowledge and information. So can't live without that.

Dan Pascone (24:50): All right, so that's a perfect segue into my next one. What's one book that has influenced how you think and how you live?

Tom Kinneary (25:02): I mean there's so many, but I'll pick the one that first comes to mind. It's Principles by Ray Dalio. Very clear instruction on how to develop your decision criteria. So anytime you make a decision, whether it's in your life or your business, you carefully define what your criteria is for making that decision. And from that you can distill principles which will enable you in the future to not only get better at making the decision, but you don't have to spend time thinking about whether you should or shouldn't do something. Since you've already defined the principle, you can simply just refer back to the principle and refine it over time and then from there just make really good decisions.

Dan Pascone (25:47): Cuts down that decision loop because you've already essentially laid the framework. That's a great one. What's one habit that you would say has had a big impact on your success?

Tom Kinneary (25:50): Definitely the gym, definitely exercise. Something that my dad taught me when I was thirteen. We got in the basement, started lifting weights at an early age. And to me that's a habit where it teaches you discipline. You have to show up every day, you have to just no matter what's going on, you're tired, you worked, you always have to make time. So discipline and determination combined, it elevates my performance elsewhere because if you can show up when you don't want to, it challenges you to show up in other places where you might not want to.

Dan Pascone (26:43): Yeah, I agree. Personal fitness and health has a real downstream effect on your entire life and how you show up and how you execute. All right, let's talk about your bucket list. Can you tell us something that you've already checked off and then something that's still on the bucket list?

Tom Kinneary (26:58): The bucket list. Something I haven't checked off would certainly be scaling the business. It doesn't necessarily have to be my business, but scaling a business that combines people, combines strategy, combines clear decision making, combines technology to create products that can really benefit the world, advance civilization. Probably sounds like a pretty cliche goal, but it's important to me to be able to do something where after I'm long gone and I've handed my estate over to my successors, at least have a legacy where people can look back and say he did something really good and people benefited from it. So that would be something that is on the bucket list that I haven't checked off yet, but I'm actively pursuing every day. And then one that I have checked off, I'm adopted from the country of Colombia, and it was always a goal or a desire of mine to visit the country. Not having known anything about it growing up here in the United States. And so as a kid I could always remember myself saying I can't wait until I'm older to go back to my country and see what it looks like. And it was around twenty one or twenty two when I finally got that opportunity to go back and see where I came from and experience the culture and the cuisine, which is phenomenal. I would highly recommend authentic Colombian food to anyone.

Dan Pascone (29:21): Very cool. That's awesome. All right. Last one. One piece of advice you would give to your younger self. What would it be?

Tom Kinneary (29:35): I would certainly say, and I would advise any parent to adopt what I'm about to say with their family. Growing up, it's important that you realize that as an independent person, the decisions you make are not always going to appeal and appease the people around you. And so people can be criticizing and they could maybe not accept you for the decisions you make. So what I would give as advice to my younger self would be, irrespective of what other people think or say about you, just have good self-love for yourself. And this might be more of my empathetic and compassionate self coming out now. But have good self love for yourself and understand that it's okay to make decisions that other people don't accept. Just do what you know you think is best and in good faith and go from there. But definitely have the self love to know that you are lovable, you are valuable, and the world will love you no matter what this one person or group of people may say. Hopefully that wasn't too deep, but it's part of me.

Dan Pascone (30:51): No, I love it. It's really good advice. A lot of people could benefit from that. You're right. A lot of people could get rid of their head trash as I call it. Good stuff. All right. And then Tom, finally, if our listeners want to connect with you, collaborate with you, just learn more about you, where can they find you?

Tom Kinneary (31:03): Yeah, I'd say LinkedIn. I'm pretty active. You can look up Thomas W. Kinnery on LinkedIn. We can probably put the spelling somewhere in the show notes. That would be a good way, just DM me, add me, or if you want you can email me too. My email is available on LinkedIn. So either one of those channels is great.

Dan Pascone (31:24): We'll put it in the show notes for sure. All right, awesome. Very cool, Tom. Thanks for coming on today. I really enjoyed the discussion.

Tom Kinneary (31:39): I really enjoyed this, Dan. Thank you for inviting me and much appreciated.

Dan Pascone (31:44): You bet. That's it for the episode. You can find our podcast along with our newsletter and YouTube channel, all for free at makingsenseofyourmoney.com. And as always, be sure to prioritize your version of a rich life. Cheers.

RESOURCES AND CITATIONS

Principles by Ray Dalio (recommended by Tom Kinneary in the episode)

FREQUENTLY ASKED QUESTIONS

What is the seven-pillar visualization exercise Tom Kinneary describes and how can I apply it?

The exercise Tom ran five years ago starts with a very specific mental image of an ideal day, not a list of goals but a lived experience played out from the moment you open your eyes in the morning to the end of the evening. The question is not what you want to accomplish but what you see, who is around you, how your morning progresses, and how the day flows through afternoon and into evening. From that specific mental picture, Tom identified what was present in that imagined day that was not yet present in his actual life, and organized those desires into seven pillars. He keeps timestamped written logs of the visualization and reviews it over time. The picture has barely changed in five years, which tells him the vision is clear and stable. The pillars then structure how his week is designed, including what happens during his off-peak seasons when two of the business-focused pillars are less active and the other five take more space. Consult a qualified financial planner to pair this kind of life design work with the financial modeling required to make it achievable.

What does it mean to reverse engineer your work-optional number?

Tom Kinneary describes it as defining the end zone first: the age at which you want work to be optional and the funding required to sustain that life. From there you calculate the delta between your current position and the target. Then you back engineer what that delta requires each year in income and invested capital, and what kinds of investment returns are needed to bridge the gap by the target date. The process converts work optionality from a vague aspiration into a specific math problem with a specific answer. Most people have a general sense of a number they are building toward but have not done the reverse engineering that tells them exactly what that number requires of them right now in terms of savings rate, investment allocation, and income growth. Consult a qualified financial planner for guidance on modeling your specific work-optional number and the path to reach it.

What is the competitive energy supplier option and does it apply to me?

In approximately 15 states across the United States, both residential and commercial energy customers have the option to choose their energy supplier rather than defaulting to the local utility. The local utility retains the regulated monopoly on delivery through the pipes and wires. But the commodity itself, the natural gas or electricity supply, can be sourced from a competitive supplier. For commercial customers especially, locking in a forward supply rate for a defined period eliminates one variable from the budget: you know exactly what your energy cost will be and the only remaining variable is consumption. Tom's advice is to search your state name plus energy supply to find the relevant board or forum listing competitive suppliers available in your area.

How do energy prices fluctuate seasonally and when is the best time to lock in rates?

Natural gas prices tend to rise in winter because heating demand increases. Electricity prices tend to rise in summer because air conditioning demand increases. These are supply and demand dynamics that repeat seasonally. For budgeting purposes, Tom suggests looking at what you paid in the prior year's peak period and comparing it to current rates to assess whether locking in makes sense. For businesses, locking in a forward rate before peak season converts an unpredictable operating cost into a fixed budget item. The value is not necessarily getting the lowest rate at any given moment but eliminating the price risk variable entirely so your budget planning is based on consumption only. Consult a licensed energy broker or advisor in your state for guidance specific to your location and consumption profile.

What is the path from owner-operator to work-optional for a business founder?

Tom Kinneary describes it as a multi-stage transition rather than a single event. The current stage is owner-operator, where the business depends on him operating it daily. The next stage involves hiring managers he trusts and allowing those managers to hire their own direct reports, reducing his required involvement to periodic oversight of the most important affairs. The stage after that is a full handoff of daily management to those leaders, with Tom stepping in infrequently. The eventual stage is a full exit into a passive investor or silent partner role, at which point work is fully optional because the income is not dependent on his active participation. For founders and entrepreneurs, this framework requires thinking about business building not just as a way to generate income today but as a way to create an asset that eventually does not require its creator. Consult a qualified financial planner and business advisor for guidance on structuring your business exit and transition timeline.

How does seasonality in a business create a natural prototype of work optionality?

Tom's natural gas advisory business peaks in winter and enters shoulder months in spring and summer. During the peak season he is fully engaged. During the shoulder months, the work demand drops and the flexibility to shift focus toward other pillars of his life increases significantly. For executives thinking about hybrid retirement, this seasonal structure is a useful model to study: it demonstrates that work optionality does not require a full exit or a permanent stop. It can exist within a business structure as a natural rhythm between high-engagement periods and lower-engagement periods. Building that kind of flexibility into a business, career, or transition plan before full financial independence is achieved can provide a meaningful taste of work-optional living while the financial architecture is still being built. Consult a qualified financial planner for guidance on how to model the income implications of a seasonal or variable work schedule during a transition.

RELATED INTERNAL LINKS

NEXT STEPS

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