In this episode, we talk about what it means to move beyond simply earning a strong paycheck and start building wealth with real intention, especially for people in tech who are in the middle or later stages of their careers. We start with the idea that success can remove urgency. Early on, financial decisions feel obvious because everything is new and growing. Later, income is steady, accounts are already set up, and the basic systems are running. On the surface, everything looks fine. But that can create a quiet risk because passive financial habits keep shaping the future without anyone stopping to ask where it is all leading.
We focus on the importance of clarity. Saving a large amount each year can look impressive, but that does not automatically mean the long term outcome matches someone’s goals. Rising spending, overreliance on employer stock, or disconnected decisions across accounts can slowly push someone off course. The key is not that anything is broken. The issue is that many people have never paused to see the full picture. Once they do, they can compare where they are headed with where they actually want to go.
We also spend time on equity compensation, which can become one of the largest opportunities and one of the largest risks in a financial life. We make the case that equity comp should be treated as real money when it is close enough to affect cash flow. Without a plan, it can get handled like a windfall, spent too casually, or allowed to build into a dangerously concentrated position. A simple plan such as selling shares on a schedule, reviewing vesting decisions regularly, and coordinating with taxes can turn that uncertainty into something durable.
Another big theme is defining what enough means. We explain that the right starting point is not a target net worth pulled from a headline or a commercial. It starts with lifestyle. We need real numbers for what life costs today, what expenses are fixed, what is flexible, and what actually adds value. From there, the idea of enough becomes personal and measurable. That clarity can replace pressure, comparison, and vague anxiety with perspective.
We close by bringing it back to purpose. Intentional wealth building does not mean adding more complexity. It means making sure income has a role, equity compensation has a plan, risk is understood, and there is a regular rhythm for checking in. The goal is to move from something that is working okay to something that is working on purpose.
(00:00) Intro
(00:08) Why success can remove urgency
(01:18) How passive money habits shape outcomes
(04:23) What gets missed when nothing feels urgent
(05:17) Example of concentrated company stock risk
(07:09) Treating equity compensation as real money
(09:53) How to know if you are actually on track
(12:00) The pressure of comparison and feeling behind
(14:21) Where to focus when you do not have time
(16:20) What intentional wealth building actually looks like
(17:36) How to contact Thimbleberry Financial
ThimbleberryU 160 - Beyond The Paycheck
Speakers: Jon Gay & Amy Walls
Jon Gay (00:08):
Welcome back to ThimbleberryU. I'm Jon Jag Gay along with Amy Walls from Thimbleberry Financial. Hey, Amy.
Amy Walls (00:13):
Hi, Jag.
Jon Gay (00:14):
So, today, we're talking beyond the paycheck in tech. If you work in tech, there's a point in your career where things start to feel, let's be honest, pretty settled. The income is strong, benefits are there, you're saving, investing, you're doing what you're supposed to do. And from the outside, everything looks like it's working.
But underneath that, there's that little voice. “If I just keep doing this, is it actually leading somewhere?” Because nothing feels wrong, but it doesn't really feel fully intentional either. At what point does doing fine quietly become a risk?
So, today, we're going to talk about what it looks like to move from doing fine to building wealth on purpose, especially when you don't have the time to constantly manage it. Do you feel seen yet? Amy, why is this such a common place for mid-career tech professionals to land?
Amy Walls (01:01):
I get excited about this topic. First, I think what we're talking about can be true for mid-career people in tech, but also beyond that. It's usually not beginning. So, mid-career and beyond. And it's because success removes urgency.
Amy Walls (01:18):
Early in a career, decisions feel more obvious. The need for the decision is more obvious. Maybe how to make it might not be, but that it's there, yes. You're building, growing, figuring things out. But then later on, things start to become a little more steady. You're used to those decisions. They're not as new. They're more comfortable. The income is steady, accounts exist. They are likely being added to, and nothing is acting on you to force a decision. It's routine.
So, what we see is people doing is “the right things” but without a clear system behind them. So, money goes into a 401(k), some goes into savings, some goes into a brokerage account. And the rest just kind of gets absorbed into life because these other things were set up on autopilot. It works, there's a reason you put those in place, but it's passive.
And passive decisions don't feel risky in the moment, but over time, they quietly shape an outcome, and that outcome may not be what you're looking for. This is where the shift happens, when someone realizes they've been busy, but not necessarily intentional.
Jon Gay (02:46):
Oh, okay. That makes sense. So, if nothing feels urgent, most people aren't going to stop to question it.
Amy Walls (02:50):
Exactly.
Jon Gay (02:50):
But if someone did pause and ask, "Is this actually working?" What should they be looking at, Amy?
Amy Walls (02:56):
Well, let's start with a simple question. If nothing changes, where does this lead? And most people haven't seen the answer to that clearly. They're optimizing pieces of their financial picture, but they haven't connected the whole thing.
So, for example, someone might be saving $50,000 a year across accounts, which might be great. But if their spending is rising at the same pace or more, or a larger portion of their net worth is tied up in their employer stock, that long-term outcome may not look the way they expected.
And again, it's not because anything is broken, but because for the first time when they see that, they actually can see the direction. That's not what I intended. That's not what it looked like five years ago when I made this decision. And that's clarity. Clarity doesn't mean changing everything. And sometimes, people are afraid of clarity for that reason.
It means knowing where you want to head and where you're headed, then being able to make decisions that actually align with where you want to go.
Jon Gay (04:06):
I think a lot of people assume” I'll get to that later,” but later doesn't always come. You’ve heard the joke about the meeting of the official procrastinator society, it starts tomorrow. So, what tends to get missed when someone doesn't have time to stay on top of all this?
Amy Walls (04:23):
Well, Jag, you're hitting the nail on the head with this. Usually, the decisions that matter don't feel urgent. So, things like equity compensation or tax strategies, or how everything is structured across accounts. They're not daily decisions, so they get pushed. I'll share, for example, at home, I don't check my mail on a daily or weekly basis.
Jon Gay (04:47):
Really?
Amy Walls (04:48):
No. We live in an older home, we have a mail slot. Our mail drops into a closet and it has to be sorted. And I don't check it daily because I know that there's really nothing important that comes through the mail slot. Every once in a while, there is, but that's rare. So, that could be something I do daily, but because it's landing in a closet, I don't think about it. And it doesn't get me into trouble. So, I think that's similar to the situation we're talking about.
So, to put this in real terms of a person, I'm thinking of someone who had built up, let's say about $800,000 in company stock over time. They'd made the decision that they were going to keep that company stock at one point, nothing felt wrong. They'd made the decision. The company was doing well, their career was strong and the stock had grown.
But when we worked together and we stepped back, that one position represented more than half of their investible assets.
Jon Gay (05:58):
Oh, geez.
Amy Walls (06:00):
And their salary depended on the company, and their bonuses depended on the company. And then they realized most of their wealth did too.
Jon Gay (06:09):
Over concentration risk.
Amy Walls (06:10):
Absolutely. So, if something changes at that company, it's going to show up everywhere at once. This person didn't make a mistake with their decision-making. When they decided, it was really low risk, but as time passed, time expanded and their life expanded, that situation also changed and intentionality was missed because the former decision worked when it was made.
And once they saw that, their goal wasn't to fix everything all at once, it was to make one clear decision about how to move forward. So, it wasn't doing more, but it was about finally seeing what was already there.
Jon Gay (06:55):
I think that's a great example because on the surface looks like success. But underneath, there's that creepy risk that more people realize it's the monster under the bed. So, when it comes to equity compensation, how do you turn that into something lasting?
Amy Walls (07:09):
Well, the biggest thing I think is a mental shift in treating equity compensation as real money, not future potential. Now, some of my clients listening might say, "Whoa, you're contradicting yourself." And I say that because we don't count equity compensation we don't have, or that isn't coming up in the near future in a plan.
But when it's coming up soon, we count it as real money because it plays a role in cashflow. And if we don't count it and all get spent, and that happens a couple times, now that's part of lifestyle, and that means we're expecting to spend like that probably after we've retired too.
My point is a lot of people separate these mentally. And so, when it's ignored at the cashflow level, it most often gets treated as an unexpected windfall. And we all know the stories of lottery winners who end up worse off. That's an unexpected windfall.
Jon Gay (08:17):
One of the things that you taught me in this podcast that has really stuck with me is when you have a windfall, you spend it multiple times: "Oh, I've got this money, I can spend it. Oh, I'm going to spend it on this. Oh, I can spend it on this too. "And you spend the same money three or four times, and it comes back to bite you.
Amy Walls (08:31):
That is what most people do and it's what we want to avoid.
[Laughter]
So, going back to this equity compensation, equity comp can become one of the largest parts of someone's net worth. And without a plan for how we're handling that, it can also become the largest source of risk.
So, we create simple discipline. That might be selling a portion of shares at each vesting. Maybe it's selling all of them based on what's happening, or maybe it's reviewing positions on a set schedule. All of our clients are different in that based on where they are financially and how they think about risk.
And then we coordinate all of that, that selling or the reviews with taxes and where that money needs to go next. So, the goal isn't to give up growth, the goal isn't to decrease lifestyle. It's to make sure that what you've already built stays or becomes durable because wealth isn't just about what's growing, it's about what's still there when you need it.
Jon Gay (09:53):
At some point, all this comes back to a bigger question, Amy. How do I know if I'm actually on track or just staying busy? How do people figure out what enough even looks like for them?
Amy Walls (10:04):
Yeah. I think we've talked about this in a prior episode, but I love that you're bringing it up again. Most people try to start with a number. We were taught that by a commercial several years ago, but that's usually not the right starting point.
To get this right, we have to start with lifestyle. And what does it actually cost to live your life today? Not with a rough guess (I'm throwing darts), but with real numbers. Then we can take those numbers, and we can separate what's fixed from what's flexible.
From there, we can start to talk about, when we look at this, what would you like more of? What if these things isn't really adding value to your life, and that's changeable? And then once that's clear, the numbers really start to become more meaningful.
So, to really go back to your question (what's enough), that's the process, and why it's not one size fits all is for one person under that process. Enough might be $5 million. For someone else, it might be $2 million. And for someone else, it might be $10 million.
So, this difference isn't arbitrary. It's tied to how they want to live, that they can be prepared to also succeed at. And so, once that is defined, what typically happens is progress starts to become more visible because it's not a guessing game.
You can feel and see the progress together, and you're measuring it against something that matters to you, not something arbitrary. Like by age 40, I'm supposed to have X amount in my retirement plans. Well, based on what?
And when all of that happens, that's usually when people can take a deep breath because the pressure is getting lower.
Jon Gay (12:00):
Yeah, that pressure piece is really interesting because I think a lot of people in this stage feel like they should be further ahead even if everything looks good. Where's that Keeping up with the Jones kind of come from?
Amy Walls (12:11):
Yeah, Jag, it's so good that you're bringing this up. That is a kind of quiet, insidious kind of pressure. Nothing's wrong, but it doesn't feel settled either. And I think it truly comes from a lack of visibility. I don't know what I don't know.
We don't recognize that about ourselves, but when we see the neighbors doing it, we fill in the pieces with, "They have all this stuff I don't." And so, we tell maybe better stories about our neighbors, about what we want to be, because we look at, and we tend to hang out with people who we think are in better positions than we are.
Jon Gay (12:52):
Yeah, psychologically.
Amy Walls (12:54):
Because that helps us move up. And so, we're telling ourselves a story that may or may not be true, and we don't know all the pieces of that story for them. And so, I think the point, Jag, that you're getting at and that this podcast is about, is that when progress isn't clearly defined, it's really hard to feel it.
And so, that question about the neighbors, that's not clearly defined, and so we're filling in. I'm thinking of somebody who felt behind, despite having saved consistently for years and was a very good saver. And when we mapped everything out, well, first of all, they thought that they would never have enough money.
So, they were really worried and they were already retired, but they were worried about doing anything they might enjoy because it would cost money, but they were actually well ahead of where they needed to be and could more than double their current spending.
Nothing about their financial situation changed in that moment. What changed was how they felt about it because now, they had context and they felt better about allowing themselves to do the things that would make their life meaningful. Their pressure got replaced with perspective.
Jon Gay (14:21):
I like that a lot. If someone is listening and they're thinking, "I don't have time to optimize everything," let's triage this a little bit, Amy – what actually matters the most? Where should they focus?
Amy Walls (14:31):
First, start with direction, not detail. And by direction, in a sense, I'm talking purpose. The highest impact area is how your income is being used. I know it's not the place people want to look. They want to say most often, "Ooh, let's make my investments do better."
But the reality is where your income is being used is going to drive everything else. So, look not just at how much you're saving, but where it's going and what it's meant to do. And then add on taxes, because some of your money does go to taxes too, especially when we're adding equity compensation into this picture.
And then we look at risk, and from there, we can look at it all together and say, "Am I too dependent on one outcome? Am I counting on one of these things to make the rest happen?" That's important. Going back to what I said earlier about often, we’ll focus on investments.
So, maybe someone spends time picking investments thinking that's the place to focus, but they may be sitting on large amounts of cash or concentrated stock that they haven't put a plan in place for. They're picking investments for what they already have.
And so, what we've done is we've jumped over where the opportunity is to do what we're most comfortable with. And so, what we want to do is focus on the decisions that will actually move us forward.
Where's my money going? What is it supposed to do for me? And when do I need to revisit this to make sure it still aligns? And when those are clear, they can go in the calendar as a reminder, and everything gets simpler.
Jon Gay (16:20):
Got it. So, to put a bow on this, Amy, what does intentional wealth building actually look like for someone who's already comfortable, zooming back out here?
Amy Walls (16:29):
It's simpler than people expect. It's not so much about adding strategies because that makes things harder. It's about making sure the strategies you already chose are still working for you. So, your income has a clear role, your equity compensation has a plan, you understand what you're building towards, and that you have a rhythm for checking in so nothing sits too long and nothing gets forgotten.
And when all of those pieces are in place, action’s easier, decisions are easier, and progress actually makes you go, "Yeah, I'm doing it, and I'm doing it right." If I say it a different way, Jag, it's moving from something that's working okay to something that's working on purpose.
Jon Gay (17:15):
Okay, I like that. And it's probably a good place to leave it. So, if things are going well financially, the next step isn't necessarily doing more, it's making sure what you're already doing is leading somewhere you actually want to go. So, thanks for walking us through that, Amy.
If our listeners or viewers (again, we are on YouTube now) want to reach you and your team at Thimbleberry Financial, how do they best do that?
Amy Walls (17:36):
Yeah, we can be found online at thimbleberryfinancial.com or by giving us a call at 503-610-6510.
Jon Gay (17:46):
Always good, actionable information here. Amy, we'll talk again in a couple of weeks.
Amy Walls (17:49):
Sounds great, Jag. Look forward to it.
[Music Playing]
Voiceover (17:51):
Securities offered through registered representatives of Cambridge Investment Research, Inc., a broker-dealer, member of FINRA, SIPC. Advisory services through Cambridge Investment Research Advisors, Inc., a registered investment advisor. Cambridge and Thimbleberry Financial are not affiliated.
Discussions in this show should not be construed as specific recommendations or investment advice, always consult with your investment professional before making important investment decisions.
Securities offered through registered representatives of Cambridge Investment Research, Inc., a broker-dealer, member of FINRA, SIPC. Advisory services through Cambridge Investment Research Advisors, Inc., a registered investment advisor. Cambridge and Thimbleberry Financial are not affiliated.