In this episode of ThimbleberryU, Jag and Amy talk about the difference between simple investing and ignoring your portfolio. This is especially for those of you working in tech, where it is easy for much of your financial life to become tied to the same industry without realizing it. Your paycheck may come from tech. Your RSUs or stock options may depend on your company’s performance. Your future career growth may depend on the same sector. Then, on top of that, your investments may also be heavily weighted toward technology through index funds or individual stocks.
Amy explains that many investors want a “set it and forget it” approach because they want peace of mind. That is understandable. The problem is that simple and unattended are not the same thing. A target date fund may feel passive to the investor, but there is still a process behind it. Your fund is being rebalanced and adjusted over time. That is very different from building a portfolio once and then never checking whether the risks still fit your life.
The biggest issue for you could be concentration risk. This is when too much of your financial life is exposed to the same company, industry, or type of investment. This risk often builds slowly. It may not come from one bad decision. It can come from you saving consistently, investing responsibly, holding company stock, and buying familiar tech names on the side. During strong markets, that can feel great. But when layoffs, downturns, or sharp drops hit, your risk becomes much more obvious.
Jag compares it to gambling, where early success can make someone feel like their strategy is working even when they are taking on more risk than they realize. Amy agrees: success itself can quietly create concentration. A stock or sector does well, becomes a bigger part of the portfolio, and starts to feel normal. That is exactly why rebalancing matters.
Rebalancing is not about you trying to predict the market. It is about managing risk. It keeps yesterday’s winners from becoming tomorrow’s overexposures. For tech professionals, this can be especially important because strong performance in the sector may increase both your confidence and concentration at the same time.
We also talk about the emotional side of company stock. Amy explains that once shares vest, they become part of your investment portfolio. At that point, holding them should be an investment decision, not just an emotional one. One helpful question we ask clients is this: If your company paid you the same amount in cash instead of stock, would you use that cash to buy company shares? For many people, the answer is no.
Your long-term investing should feel calm, simple, and intentional. It does not require reacting to every headline. But it also should not mean abandoning your portfolio for years at a time. A healthy strategy includes periodic reviews, rebalancing, checking concentration risk, and making sure your investments still match your goals. Calm requires attention, not abandonment.
(00:00) Intro
(00:49) Why tech workers want simplicity and peace of mind.
(02:00) Target date funds vs portfolios that are built once and ignored.
(03:42) A seemingly diversified portfolio can have concentration risk
(05:52) How success can quietly create concentration risk.
(06:44) Rebalancing
(08:22) The emotional attachment people can have to company stock.
(10:39) The healthy middle ground: calm, simple, and intentional investing
ThimbleberryU 162 - Simple Investing vs Ignoring Your Portfolio
Speakers: Jon Gay & Amy Walls
[Music Playing]
Jon Gay (00:08):
Welcome back to ThimbleberryU, I'm Jon Jag Gay, Amy Walls from Thimbleberry Financial joins me as always. Hey, Amy.
Amy Walls (00:14):
Hey Jag, good to talk to you today.
Jon Gay (00:16):
Always a pleasure. Today, we're talking about “set it and forget it” investing, specifically for people in tech. I know this is a specialty of yours at Thimbleberry.Amy, this feels especially relevant right now because a lot of people in tech may already have most of their financial life tied to the same industry.
We're talking their paycheck, their RSUs, their future career growth, even their investments through index funds.So, someone can feel diversified while actually carrying a lot more concentration risk than they realize.So, when people in tech say they want a simple “set it and forget it” investing strategy, what do you think they're really hoping for?
Amy Walls (00:49):
They're really hoping, I believe, for simplicity and peace of mind. They want confidence that things are moving in the right direction without feeling like they need to constantly monitor markets. And that's very reasonable.The important distinction is whether there's still a process underneath the simplicity.
I'm going to talk about target date funds for a moment.You can love them or you can hate them. What they do is they feel passive to the investor. But underneath that, it's still being rebalanced and the allocation is being adjusted behind the scenes.
So, the investor doesn't have to think about how all of those changes are happening or second guess should they happen compared to if they have a portfolio where they would need to make those choices.
And that's very different from building a portfolio once and revisiting whether the risks still fit your life. So, I think the message I'd want our listeners to walk away with is simple and unattended are not the same thing.
Jon Gay (02:00):
That's a really good point. I think about those target date funds. My first full time job in my 20s,I didn't know anything. I was born in 1980, I'll probably retire 2040, 2050.That date fund, I'll just pick that one.
But yeah, having that set where somebody else is doing the work behind the scenes versus something you've set up and don't touch, you're right, totally different. And I think this is the part that surprises people: someone can own index funds and genuinely think, “Okay, I'm diversified.” Check! But when you zoom out, maybe the bigger picture tells a different story.Why does that happen so often in tech?
Amy Walls (02:33):
Well, a lot of tech professionals already have several parts of their financial life connected to the sector. Their income depends on tech, their RSU or stock options depend on how the company does and their way in tech.Their future earnings potentially may depend on tech, too.
And so, then their investments may also heavily lean towards technology companies through indexes or maybe they also bought some stocks. And I can say from people coming to us for initial meetings, we see a lot of this in tech where they are comfortable with tech, so they have a portfolio that is tech-heavy.
And during strong markets, that can feel incredibly rewarding. But it's why the concentration risk can be really easy to miss. And the concern becomes much more visible, even though it's always there when there's layoffs, sector downturns, or sharp drops in a single company stock.
Jon Gay (03:41):
That makes sense.
Amy Walls (03:42):
So, I think the point is a portfolio can look diversified while someone's overall financial life is still heavily concentrated.
Jon Gay (03:50):
Yeah, and I think that's a mistake a lot of folks make. And I imagine this usually doesn't happen because somebody made one big mistake setting it up. It's probably something, Amy, that kind of slowly builds over time and doesn't feel too dangerous in the moment.
Amy Walls (04:02):
You're exactly right. Most concentration risk builds gradually. I was actually looking at a portfolio yesterday where a client had a Play account and they have some other investments, and I did an analysis and they had over 12% in a single company.
And it wasn't the company they work for. It was just one they felt good about, bought it on the side, in what was a small company but because so many of their other holdings already held it too, it was about 12% of their portfolio.
So, in this case, the person consistently saved, invested responsibly. Now add, if it's your own employer, maybe you accumulated stock over the years too.Nothing really is feeling risky because the company is growing and the market is doing well. That's not where risk hits us, it's when all of the sudden, that company or that sector don't perform as well.
And we know right now with tech, there's a lot of concern about the layoffs and what's happening there. So, it's a pretty common question right now of what do I do?What makes sense? And revisiting the strategies.
Jon Gay (05:23):
I feel like this is a little bit whether it's in a casino or sports betting or whatever it is right now, it's that the worst thing that can happen for a new better is to be successful early. “Oh, this is working. I don't have to change anything.”
They're missing the underlying issue, which is many risks or other things like, “Oh, I just hit black on the roulette wheel five, six times, or all five football teams I bet on won today, it's working for me right now.”Well, guess what? That's not always going to be the case.
Amy Walls (05:52):
Yep. We need a strategy that works today and will work long term. And a lot of times with these passive strategies, we forget that they still need adjustments in order to work for the long term.What you're also getting at Jag, with that story or that point, is success itself can quietly create concentration risk.
You've built and built and built through that activity and you're willing to take on more and more, but you don't even think it's more and more because you've just gotten used to it.
Jon Gay (06:26):
Yeah, for sure. So, we talk about concentration risk and that brings us to rebalancing. It's one of those investing terms that people hear all the time, but I think a lot of listeners probably associate it with trying to outsmart the market.Can you disavow us of that misnomer? We'll use some big words here.
Amy Walls (06:44):
(Laughs) Well, let's talk about its real purpose. Rebalancing is primarily about managing risk, not about predicting markets. It helps us prevent yesterday's winners from quietly becoming tomorrow's overexposures.
And it's especially important in tech-heavy portfolios because this strong performance, as we've said, especially that we've had over the last few years, can naturally increase concentration and comfort over time. So, rebalancing helps maintain the level of risk that you originally intended to take. So, rebalancing is not prediction, it's process, it's a safety feature.
This is not rebalancing if we go back to that target date example earlier. That's the thing that when people have a portfolio of index funds quite frequently, and do-it-yourself investors (I'm talking to you here) it's, “Ooh, well, I don't want to rebalance that because I'm on a roll, or the portfolio's on a roll, and I don't want to pay the taxes that might come from that.” So, this simple investing strategy that we're talking about really isn't simple, it's “ignore.”
Jon Gay (08:05):
I can see this being difficult emotionally too because company stock doesn't just feel like an investment. For a lot of people, it's kind of the fruits of your labor. It represents years of hard work and career success.
So, Amy, how should someone think about company stock more objectively without feeling like they're somehow betting against the company they work for?
Amy Walls (08:22):
Just like receiving an inheritance with certain investments, there is emotional attachment. The same is true quite frequently with the stock someone gets from their employer. People believe in the company.They feel grateful for what the stock has already provided to them, if they've used some of it, and they connect it to their identity and career success.
I've heard, well, my employer's going to know if I don't have this stock because they're connected to all of these accounts.That might play into my performance review because they will think I'm not committed if I don't maintain this.
Jon Gay (09:07):
Oh, wow, yeah, “I'm not all in.” That is an interesting thought.
Amy Walls (09:10):
But the reality is once these shares vest, become part of the investment portfolio, that's what they are, and we need to have a strategy to handle our emotions that might get us into trouble.
Jon Gay (09:24):
Like so many other things in personal finance (chuckles).
Amy Walls (09:28):
So, continuing to hold them should be (and I'm sorry to use the word should) when done correctly, an investment decision. One thing I think about is, if your company paid you the amount of cash today that they pay you in stock, would you use that cash to buy your company's stock?
Jon Gay (09:53):
Right. That's a great way to look at it.
Amy Walls (09:56):
And most people, when asked this question, are emphatically no. And I might ask it, let's say you get a bonus of 30%, 40% each year, would you buy stock with that?Absolutely not, without missing a beat. Well then, why are you going to continue to hold all of these shares?
Jon Gay (10:21):
Alright, so Amy, if somebody listening wants investing to feel simpler and less stressful, but also wants to avoid drifting to that sort of neglect that we talked about earlier-
Amy Walls (10:31):
Jag, let's just say it, ignore.
[Laughter]
Jon Gay (10:33):
Okay. Where is the healthy middle ground here?
Amy Walls (10:39):
The healthiest version of long-term investing is calm, simple, and intentional. It doesn't require reacting to every headline or constantly changing investments. But it also doesn't mean ignoring the portfolio for long stretches of time.Those are two ends of a spectrum. Healthy habits include periodic reviews, rebalancing, even though it can cause a tax bill, evaluating concentration risk, and revisiting goals to make sure that your investment strategy aligns over time.
And so, especially in tech, where compensation investments become so deeply connected and emotional, it helps to occasionally zoom out and look at the full picture. Long-term investing should feel calm, and calm requires attention, not abandonment.
Jon Gay (11:37):
There you go (laughs). Alright, so the takeaway here is not that “set it and forget it” is wrong, Amy. It's that the healthiest version of it is kind of between the extremes.It's got some intentional structure underneath it, especially for people in tech, whose careers and investments are so closely connected oftentimes.
Amy Walls (11:56):
Jag, that's it. Exactly. I've taught you well.
Jon Gay (12:00):
You have. I have been at the feet of my sensei for six years now (Amy laughs).
Amy, if somebody wants to talk to you and your team at Thimbleberry Financial (I didn't think you'd like that line that much, but okay), how do they best find you?
Amy Walls (12:14):
They can find us online at thimbleberryfinancial.com or by giving us a call at (503)-610-6510. And I was laughing at the line because it was silly (laughs).
Jon Gay (12:28):
I'm glad after all these years, I can still surprise you. Take care, and we'll talk again soon.
Amy Walls (12:32):
Yes, sounds good.
[Music Playing]
Jon Gay (12:33):
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.