How Much is Enough?

For most people, “enough” starts as a number. A salary, a savings target, a net worth figure that feels like the finish line. But as you build a business, raise a family, and move through life’s harder moments, that definition tends to shift in ways that surprise you. In this episode of Couchside Conversations, Chief Operating Officer & Chief Marketing Officer Stacey McKinnon sits down with Scott Gilmore, CEO of Ascend and longtime collaborator at Morton Wealth, to explore how the concept of “enough” evolves and what it actually takes to build a life that feels that way.

“Enough” evolves from a financial number into a feeling. When you’re young, enough is defined almost entirely by money. As you grow professionally and personally, the definition expands to include impact, relationships, time, and the kind of work that feels meaningful. Both Scott and Stacey reflect on how their own versions of enough have shifted significantly over the course of their careers.

Knowing your financial picture is what creates freedom. Scott describes seeing a full financial roadmap as a game changer—not because it changed his decisions, but because it let him make those same decisions with peace and mental clarity instead of anxiety. Many clients avoid looking at the numbers out of fear, but the act of knowing is precisely what unlocks the ability to make different choices.

Your wants and your dreams compete with each other. Lavish vacations and retiring at 60 are not automatically compatible goals. Stacey describes walking clients through an exercise that makes this tension explicit: once the tradeoffs are visible, neither goal is wrong, but the decisions become intentional rather than default. That shift alone changes outcomes.

Business ownership is an identity—which makes the sacrifice harder to see. Scott reflects on pouring everything into a business because it becomes part of who you are. The risk is that you keep building past the point where you actually need to, without ever asking whether the end game is still what you want. Resilience is necessary, but so is periodic reflection.

Keeping up with the Joneses moves you away from your own goal. Living in communities with visible wealth makes it easy to define enough by what your neighbor has. Scott’s reframe: everyone is after something different. If your goal is freedom of time and choice, spending to keep pace with others actively delays getting there. Clarity about your own target is the only real antidote.

Transcript

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SPEAKER_00 0:00

When I was in like my twenties and thirties, I think the only thing that I could define as enough was money.

SPEAKER_01 0:06

I thought that was gonna make enough better. And truthfully, I found out that my definition of enough had changed. And it wasn't just about me, it was about the people I was impacting.

SPEAKER_00 0:15

One of our team members shared with me that they bought their dream house. I just like, that was so fulfilling to me.

SPEAKER_01 0:21

There's just a sense of satisfaction that I don't think any dollar amount can truly give you, right?

SPEAKER_00 0:26

Do you know that your wants and your dreams actually compete with one another? So you want to spend more money, go on lavish vacations, that's gonna compete with your dream of retiring at 60.

SPEAKER_01 0:36

Enough is whatever makes makes you happy.

SPEAKER_00 0:39

Once we acknowledge that, we need to do it with knowledge and intention as opposed to overspending forever, and then now you're working forever. Welcome to another episode of Couchside Conversations. Today I'm here with Scott Gilmore, who is the CEO of Ascend, one of our tax partners that we work with a lot of clients on. But our story began much earlier than that. I think we've known each other for over a decade, and I feel like we've kind of like grown in our profession together in so many ways. And I wanted to have you on Couchside today because we both get a question from a lot of clients that I think we have an interesting perspective on, which is how much is enough? And as we've both grown our businesses and grown our personal lives, you're raising your family. I think this question not only is top of mind for the clients we work with, but in many ways is top of mind for us too. And so I would love to start by just having you share like how much is enough for you? How do you define that and how has that changed over time?

SPEAKER_01 1:45

Well, to your point, it's it's changed over time and how you value it's changed over time. I think when you're young enough is really money driven, it's financial, and as you get older, enough looks at quality over quantity, it looks at people interactions, it looks at fulfillment, and money isn't necessarily the focal point of what is enough.

SPEAKER_00 2:04

Yeah, it's such an interesting um perspective to have because when I was in like my 20s and 30s, I think the only thing that I could define as enough was money. And when I look at current statistics today, in Southern California, people define enough as a joint family making $100,000 a year.

SPEAKER_01 2:24

I mean, that's that that's a tough salary to live on in Southern California. It is. I mean, there's probably places in the country where that would would make it work.

SPEAKER_00 2:33

Yeah.

SPEAKER_01 2:34

I think that would be difficult here given the cost of rent and now food and gas and everything else.

SPEAKER_00 2:39

But it does beg the question of let's say that you start making more than $100,000 a year. Do you start not seeing money like as the thing that's defining enough?

SPEAKER_01 2:50

I think at some point you get to some type of financial security or some some bar that everyone has a different one. You know, there's no different values, different goals, different everything, different family situations. And then you start to define enough through through other fulfillment ways. Um, and that's been it's it's part of maturity. It's kind of like the the plan as you get older, this kind of goes with it.

SPEAKER_00 3:13

Yeah, totally. Do you feel like there was a time specifically that you reached that point where you said, Okay, I do feel more financially secure now, so what is my new enough definition?

SPEAKER_01 3:24

You know, for me it was after we went through our merger. So as you know, worked for the same company my entire career. We spent about 18 years together growing a firm from 12 people to 50, ended up merging into a larger firm, and I thought that was gonna make enough better. And truthfully, I found out that my definition of enough had changed. And it wasn't just about me, it was about the people I was impacting, both my clients and the staff that I had grown up around. And in order to have enough, I had to do something that impacted them, not just me and my family.

SPEAKER_00 3:57

And you made those changes fat fairly quickly. You went from small business to big business back to small business where you had to take all of the risk.

SPEAKER_01 4:06

Yeah.

SPEAKER_00 4:06

And with some of your partners too, to actually say, like, it's not about the money that we're making, it's actually about the quality of the business that we're running.

SPEAKER_01 4:14

I just realized that in order to have enough in my own world, I needed to do more than just make a good living, serve my clients. I needed to serve the people that helped me get to where I was. And I thought the best way to do that was to take those risks on my own and you actually relive what fulfillment looks like to you, and you you reimagine that and it comes back in a different definition once you've had an opportunity to do that on your own.

SPEAKER_00 4:41

Yeah, it's in it's interesting. It's not that you built the business, it's that your people built the business. And so focusing on them and making sure that they're in a position where they can be fulfilled and thrive, everybody benefits from that.

SPEAKER_01 4:55

I mean, it's like anything, whether it's sports, your family, everything is better as a team. There's a lot you can accomplish on your own. But when you do it with a team and you're impacting multiple people and you can get exponential growth in families and people's lives, that's fulfillment in ways that can be enough.

SPEAKER_00 5:12

It was so cool the other day, uh, one of our team members shared with me that they bought their dream house that they've been talking about for five years with me and saying, This is my goal, this is my goal, this is my goal. And they moved in last week, and I just like that was so fulfilling to me because as part of like uh running more in, I want to see my team members achieve those goals that they've always wanted.

SPEAKER_01 5:33

There's a s a sense of satisfaction that I don't think any dollar amount can truly give you, right? We as humans crave interaction, impact. That that's why we do what we do, you know, for our clients. And being able to do that to to people who you've kind of grown up with from a professional standpoint, it's a it's one of the best feelings I think I've ever had.

SPEAKER_00 5:56

Yeah, I totally agree. And there's actually something, I think just on a personal note, fulfilling about making the transition from is money the thing that's enough to where am I spending my time, where am I spending my resources, how am I like present in different areas of my life? And I feel like this really changed for me in 2024. I had like a series of events happen that were just really hard on me and my family. My husband and I lost our first pet, which we don't have kids, and so our dog is like our family, and that was so devastating. Followed by this is so bad. Like we were driving in the mountain passes and a deer ran in front of us and we hit a deer, and that was so traumatic. And then two months later, my husband got hit by a car. Like these things all happened, like in threes, because they these things do happen in threes. And in that point in my life, I just stepped back and I said, like, what are we what am I doing? Like all of these things occurred. For some reason, they were all around like death and accidents. And how am I spending my time? And what do I want my time to be? And is it continuing to like climb, climb, climb, climb a ladder, or is it actually figuring out how to maintain some type of um balance, even though I don't love that word, of like where I have time and energy into the things that are most important to me. And I remember that being like a very pivotal point for me in just changing my attitude a little bit on where am I putting my time and is it not all about the money anymore?

SPEAKER_01 7:21

I think for everybody as they go through their journey in life, right, there's no one answer, there's no right answer, there is what fits best for you. And as you mature, both from a chronological standpoint and from a professional standpoint, it the definition of of what fulfills you, and there's nothing more impactful than an event that happens that kind of gives you that, okay, let's pause, let's let's look at the situation. And you can keep grinding, grinding, grinding, and you really don't know what you're missing. And when you take a moment to reflect, it's quite healthy to give you an opportunity to make sure you're getting well-rounded, maybe not balanced, but at least well-rounded and giving yourself the opportunity to see other aspects.

SPEAKER_00 8:03

Totally. That resonates with me. One thing that a lot of our clients struggle with, kind of on this note, and I wanted to specifically ask you as a business owner, is they are trying to invest into creating whatever business it is that they run. So it could be creative, it could be mechanical something that they're trying to do. And sometimes as a business owner, you don't have enough, even financially. You're continually sacrificing, you're reinvesting into the business to make sure it survives, but it also negatively kind of impacts your family. How have you thought about that as you've grown in your career? I'm sure you've had points in time where you're like, you are sacrificing to make sure this thing in this business is gonna survive. And like, how do you find the motivation to keep going?

SPEAKER_01 8:45

I don't think you ever get to that point. You you constantly do make the sacrifice as a business owner. Um I I think as you go through the the journey of building the business, it almost becomes your baby. Yeah. And it it's it's part of who you are. And for a lot of people, it becomes part of their identity. Yeah. And so you keep giving back to the business and giving back to the business because it means something to you. But you have to have a balance. We hate that word, but between short-term thinking and long-term thinking. Because on the short term, you're gonna keep going, keep building the business, keep it afloat. But in the longer term, you have to make sure the end game is what you want it to be, right? The world's moving fast around us, things are changing in so many different facets. We all talk about technology a lot, but there's a lot more to it. And you have to constantly reevaluate, is this the best use of my time? Is my short-term decisions in alignment with my long-term decisions? And just having, again, sorry, balance between those decisions so that you don't get stuck and then one day you wake up and say, Oh my god, all of this is behind me, and I still don't have enough.

SPEAKER_00 9:53

What you needed. It's interesting though, because it I think sometimes what happens is in the world we live in today, we're so um like influenced by wanting like immediate satisfaction from things. We want that immediacy, and like a lot of times, especially as a business owner, there is a long period of time, meaning years, to like grow something to be what it is for you and what you want it to be. And I think you've probably gotten close to there at a send, although I know you and you're probably always growing and changing and wanting something new and better. That's like natural to who you are. Um but you know, there's a I I think that's something to note is that it just takes a long time and you just gotta be resilient and keep going. And I know that's been your experience too.

SPEAKER_01 10:35

Yeah. Um my the the goals change and the priorities change. And for oft for a lot of time it was the goal of building this company and making that impact on the people that we've talked about. And as it's become more stabilized, I'll call it, and and mature as a company, my shift, my focus has shifted back to my family. Yeah. Because they're the ones that truly sacrificed. Granted, as we're building, we all share in the rewards of that from a financial purpose, but my presence, my time, my energy, it was going to other places. And so I I've really tried to be cognizant of making that shift back and kind of bringing it back into harmony and trying to keep my family at the same place that I keep my clients and my team.

SPEAKER_00 11:20

Do you feel like going through the process yourself of understanding your financial situation, where you're going, actually seeing the visual of projections allowed you to have a little bit of that freedom. So it wasn't just continuing to grind, but no, actually, I see you see where I'm going.

SPEAKER_01 11:36

I'll have one word for it. It was a game changer. To to honestly, in as an accountant, as a numbers guy, like having a plan is is pivotal to me. To be able to sit there and look at here's the plan, and if you do these things, here is where you'll be, it gives you the motivation, the comfort to keep going, to stay on that track and understand that oh, at this point, maybe I can reshift and refocus things to build more well-being and well and well-roundedness in in what we're doing. It the sense of peace that that gave me, I'll never forget. I got on the phone with one of my coaches and I said, Look, I'm in a good place today, and here's why. And I'll never forget it. It's one of those memories that just always stays in the forefront.

SPEAKER_00 12:19

That's so great. So sometimes we're afraid of seeing these visuals and numbers. I've had a lot of clients say, like, Oh, I don't want the reality of my budget, or I don't want the reality of what the financial picture looks like. But there's so much freedom when you know, because then you can make different decisions. And you might have continued to grind, not like, but not needing to, if you didn't have that knowledge.

SPEAKER_01 12:40

I might have made the same or different decisions. But even if I made the same decision, the happiness I did it with, the peace I did it with, just the mental freedom that I did it with, it we all go through our journey in in a search of some type of happiness, right? Whatever that definition is for you, it's a lot easier when you don't have the weight on your shoulders and like, ah, okay, I'm I I'm gonna get this done.

SPEAKER_00 13:06

I'm okay. I know I'm okay, yeah. Um, one other question that uh some clients ask is just balancing the risk between starting their own business and knowing that it might take years to actually make it, or taking a big paycheck at a corporate company or a big company to just have that guaranteed income and know that they're gonna be okay, but they don't have any opportunity to be entrepreneurial in that. How would you advise somebody who's like trying to balance these two things of like, do I want to be an entrepreneur and own it, or do I want to be with a big company and take that paycheck?

SPEAKER_01 13:39

I think first there there's no right answer here again. Um it it's some personality traits are innate, and there are people that are just born to be entrepreneurs. It's how they're wired, it's the only way that they're gonna achieve success that for themselves, enough fulfillment, happiness for themselves. Other people are risk adverse. Yeah. And they'll take the paycheck, and it makes sense, you can live a good life, and they don't need the additional risk to feel fulfilled, to feel like they have enough. And it's really you really have to get in touch with you know who you are and what's important to you. And for some people, you may go back and forth. And for a lot of people that go the entrepreneur route, they'll exit and they'll be right back in it before you know it because they're craving more.

SPEAKER_00 14:21

Yeah, and they want to control their future, they want the destiny. It doesn't feel good to work under somebody else, it feels good to like be the maker of the thing that you want to achieve. And I think it's really important actually to know that about them yourself. I went through this exercise with a client recently where we had them list every single value they had spending time with family, um, maybe intellectual values that they had, uh, where they wanted to live values, who their friends were, and we put those on a piece of paper, and then we looked at the decisions they have ahead of them in the next year, and we basically matched them to the values. And what was really fascinating about it is about 50% of the decisions that they were making did not align with their values because they were making it for the money, not for the values. And the money wasn't necessary actually in their financial plan. So it was it was a fascinating exercise to sit back and ask yourself the question of like, Am I doing this for the right reasons? And do those reasons align with what I really want out of my life?

SPEAKER_01 15:22

And a lot of times emotion is the driver here, right? And sometimes going through the plan and looking at it, listing the values, showing the connection between the two, it gives you the clarity that emotion can oftentimes cloud. Yeah. And so that's the value of having advisors and talking to people and making sure that you don't allow yourself to get off the track when it's lines up, you're ultimately going to get to a better place. You're gonna be happier.

SPEAKER_00 15:48

Yeah, I totally, I totally agree. It they've been happier since they figured that out and have made different decisions since then. So that's been really fulfilling. One other thing that clients struggle with sometimes is just living in a community where there is a lot of wealth. Yeah. And you get these temptations to keep up with the Joneses, and all of a sudden you've defined enough not as what you want and you need, but what your neighbor has. Yeah. Um, how do you resist that temptation and like what advice would you give for that?

SPEAKER_01 16:17

One of the most difficult things to be honest, because you can't control what other folks are doing, but it is it is your reality and you see it every day. I I try to have people understand different strokes for different folks and know what it is you are trying to accomplish. For example, for me personally, freedom of choice, freedom of time are are my are the things that I'm after. And if I'm trying to keep up with other folks, I'm actually working backwards from that goal. Because ultimately, everyone has a number, everyone has an idea of what that looks like, and if you can get to it sooner, you can make the choices you want to sooner. But that means making sacrifices today and not really keeping up the way you want to. Or on the flip side, you keep up, you're gonna keep grinding a little bit longer.

SPEAKER_00 17:07

Yeah.

SPEAKER_01 17:08

So it's it's a balance, it's understanding what you're after, and really just keeping your eye on the ultimate goal. If if if your goal is to have great things, enjoy your life right now, nothing wrong with that. But there's going to be something on the other side of that, or a decision that's gonna need to be made, or a sacrifice at some point in time.

SPEAKER_00 17:25

Yeah, I I um sometimes do some work for nonprofits, and one of the questions I ask in my sessions with one-on-one with people is uh, do you know that your wants and your dreams actually compete with one another? So you want to spend more money, go on lavish vacations, that's gonna compete with your dream of retiring at 60. If you back off that a little bit, that want, you may be able to retire at 60. Sometimes I think we forget that our like wants are actually competing with our long-term dreams, and vice versa. And once we acknowledge that, it's not that one thing's wrong or the other, it's just that we need to do it with knowledge and intention as opposed to overspending forever, and then now you're working forever.

SPEAKER_01 18:08

You want to get in front of it before it's truly a problem you can't do anything about or it's punitive, more difficult than it needs to be. But yeah, I mean there are different decisions that you're going to make and they may change actually. They may evolve as as your life evolves, you get older, your family gets older, you have kids. Those decisions kind of move with what's around you.

SPEAKER_00 18:32

It's true. Alright, one last question for you. If you were just to like simply define what is enough, how would you define that?

SPEAKER_01 18:40

Living my happiest life. You know, uh enough is whatever makes makes you happy. That's the ultimate point of being.

SPEAKER_00 18:47

Yeah. Define it as happiness, not necessarily a number.

SPEAKER_01 18:51

I know a lot of people have a really big number and maybe not necessarily the happiness they thought it would come with it.

SPEAKER_00 18:56

Yep, those are trade-offs and you gotta be aware of them, right? That's right. All right. Well, we're gonna play a game called this or that now where we're gonna ask each other questions and we just we gotta choose one or the other. There's no there's no both as the answer. Sound good?

SPEAKER_01 19:10

Sounds like a plan.

SPEAKER_00 19:15

All right, so first question for you. Would you rather work 40 hours a week longer or 60 hours a week but retire earlier?

SPEAKER_01 19:26

60 hours and retire earlier.

SPEAKER_00 19:28

Yeah. I'm I probably have done that in my life. So I probably continue doing that.

SPEAKER_01 19:33

So big title or flexible lifestyle?

SPEAKER_00 19:37

I don't know if I can get to a flexible lifestyle without a big title. Even though I know that sounds a little bit egotistical, I think I have to choose it.

SPEAKER_01 19:44

Okay.

SPEAKER_00 19:45

Next question. Did you did you want to comment on it?

SPEAKER_01 19:48

I say titles don't necessarily get you which you want to go. That's probably true.

SPEAKER_00 19:53

Um Okay, next question for you. Would you rather climb faster or go slow and steady with more life balance?

SPEAKER_01 20:02

Oh, climb faster.

unknown 20:04

Yeah.

SPEAKER_00 20:04

It would be kind of boring otherwise, right?

SPEAKER_01 20:06

We've gotta have the challenge. I know slow and steady wins the race, but it's too slow. Uh spend your money now or save aggressively.

SPEAKER_00 20:18

I I think I told you earlier that that we couldn't say both. This is the same. And I feel like I'm gonna cheat on this one. Um I think probably save aggressively, because then that leads to more flexibility to do what you want.

SPEAKER_01 20:32

I totally concur. And this is a really personal choice. I think if you pull 10 people, you get five and five.

SPEAKER_00 20:37

Totally, totally different answers for that. Well, thank you so much. This has been wonderful. I appreciate you sharing your insight and kind of the the story behind the story of how you got to where you are today. Please tune in for future couch eye conversations. Thank you for being here. Wow.