June 2026
Stacey McKinnon, Chief Operating Officer, Chief Marketing Officer
Scott Gilmore, CEO of Ascend
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.
“Living my happiest life. Enough is whatever makes you happy. That’s the ultimate point of being.” — Scott Gilmore
0:00 – Introduction: defining "enough" through money, people, and intention
0:56 – Welcome and introducing Scott Gilmore, CEO of Ascend
1:36 – How do you define "enough," and how has it changed over time?
2:04 – Is $100K a year really "enough" in Southern California?
2:50 – When does financial security shift your definition of enough?
3:13 – Scott's turning point: the merger that changed everything
3:57 – Going back to small business to serve the people who got you there
4:54 – Why your people build the business, not just you
5:55 – Stacey's personal wake-up call: loss, accidents, and rethinking time
7:20 – The value of pausing to reflect instead of just grinding
8:02 – The business owner's dilemma: sacrificing for the business vs. your family
9:52 – The danger of wanting immediate results when building takes years
10:34 – Shifting focus back to family once the business stabilizes
11:20 – How seeing your financial projections creates freedom and peace of mind
12:19 – Why avoiding the numbers keeps you grinding longer than you need to
13:05 – Entrepreneur vs. corporate: how to know which path is right for you
14:21 – The values exercise: when 50% of your decisions don't match your values
15:21 – How emotion clouds decisions and why advisors help you stay on track
15:47 – Keeping up with the Joneses: how to resist redefining "enough" by your neighbor's life
17:23 – Your wants and dreams compete: what that means for retiring on your terms
18:31 – Final question: how do you simply define "enough"?
18:55 – This or That: a rapid-fire game to close out the episode
How much money is “enough” to feel financially secure?
There is no universal number, and that’s the central point of this conversation. Research in Southern California suggests people peg enough at a joint household income of around $100,000—a figure Scott and Stacey note is extremely difficult to live on in a high-cost region. More importantly, financial security is a threshold that varies by values, family structure, and life stage. Once you reach a level where basic security is no longer the daily concern, the definition of enough tends to shift away from income entirely and toward time, impact, and fulfillment.
Does more money actually lead to more happiness?
Not automatically—and both Scott and Stacey speak to this from personal experience and client work. Scott notes that he knows many people who reached a very large number and did not find the happiness they expected. The research on this tends to support what they describe: above a certain threshold, additional income has diminishing returns on day-to-day wellbeing. What tends to matter more at higher income levels is how you spend your time, who you spend it with, and whether your work feels like it matters.
How do I know if I’m saving enough to retire when I want to?
Scott describes sitting down with a financial roadmap as a game-changing experience—not because it magically resolved every question, but because it replaced ongoing background anxiety with clarity. He could see the path, identify the point where he could shift gears, and make decisions with peace rather than uncertainty. Stacey adds that many clients actively avoid looking at their full financial picture because they’re afraid of what they’ll find. The act of looking is almost always less frightening than the avoidance—and it’s what makes intentional decision-making possible.
Should I start my own business or take a steady job?
Scott’s honest answer: there is no right answer, only the right answer for you. Some people are wired for entrepreneurship—it is the only path that will give them the autonomy and sense of purpose they need to feel fulfilled. Others are genuinely better served by a stable paycheck and the security that comes with it. The key is self-knowledge. He also observes that many entrepreneurs who exit their businesses end up back at it within a few years, because building something is not just a career choice—it is part of who they are.
How do I stop comparing myself financially to my neighbors?
Scott reframes the problem: you cannot control what others are doing or how visible their wealth is. But if you are clear about what you are actually after—in his case, freedom of time and freedom of choice—then spending to keep pace with others is not neutral. It actively delays reaching the goal you care about. Stacey builds on this with her values alignment exercise: when clients list out what they genuinely value and then examine their spending decisions against that list, the mismatches become hard to ignore. Awareness of the gap is usually what changes behavior.
What does values-based financial planning actually mean?
Stacey describes walking a client through an exercise where they listed every significant value—time with family, intellectual engagement, where they wanted to live, who their community was—and then mapped their upcoming financial decisions against those values. About half of the decisions did not align. They were being made for money, not for what actually mattered. The money, it turned out, wasn’t even necessary to the financial plan. Values-based planning is simply the practice of making that map explicit before making decisions, rather than after.
How do short-term wants compete with long-term financial goals?
Stacey puts it directly: your wants and your dreams often compete, and most people never acknowledge that explicitly. Taking lavish vacations now and retiring at 60 are not automatically compatible goals. Neither is wrong. But the tradeoff is real, and ignoring it does not make it go away—it just means the decision gets made by default rather than by intention. Once clients see the tradeoff clearly, they can make the choice that reflects what they actually want, rather than drifting into overspending and then working longer than they needed to.
The question of “how much is enough” sits at the intersection of personal finance and how people want to live their lives—and it is something most financial conversations never quite reach. This episode goes there directly. It is worth listening to for anyone who has ever wondered whether they are building toward the right thing, or grinding past the point where it still makes sense.
This episode is especially relevant for:
At Morton Wealth, these are the conversations we believe financial planning is actually for. The numbers matter—but what the numbers are in service of matters more. If this episode resonated, we’d encourage you to use it as a starting point for a conversation with your advisor about what enough looks like for you.
Watch previous episodes:
Top Reasons We Overspend (Even Financial Advisors Do It)
Ask a Therapist: How to Make Your Relationship Work
DISCLOSURES
Information presented herein is for discussion and illustrative purposes only and is not intended to constitute financial advice. The views and opinions expressed by the speakers are as of the date of the recording and are subject to change. These views are not intended as a recommendation to buy or sell any securities, and should not be relied on as financial, tax, or legal advice. You should consult with your finance professional, accountant, or tax professional before implementing any transactions or strategies concerning your finances.
