In this episode of ThimbleberryU, we dive into actionable strategies to make 2025 a banner year for financial growth. We focus on practical, often-overlooked habits that can help listeners tackle common hurdles in financial planning, like maximizing contributions, handling stock options, estate planning, and finding a healthier work-life balance.
Amy Walls begins by discussing the challenges of maximizing tax-advantaged contributions. She emphasizes the importance of building habits, likening it to brushing your teeth or exercising. A gradual increase—like raising 401(k) contributions by 1% each month—can make these adjustments manageable and sustainable. Small, consistent actions build financial momentum.
Next, we tackle stock options and RSUs, particularly for those in the tech sector. Amy recommends diversifying holdings to avoid placing all financial eggs in one basket. Planning how to reinvest proceeds from selling stock in advance can help manage the emotional hurdles of timing sales. She advises consulting trusted individuals with relevant experience and reframing decisions as part of a larger financial strategy.
For those with excess cash flow, Amy suggests breaking large decisions into smaller, less intimidating steps. Like planting a garden, starting small with investments and building over time allows for control and adaptability. Monthly transfers, for example, can help build confidence without feeling overwhelming.
Estate planning is another key area where procrastination reigns. Amy advises creating annual check-ins and starting small—like updating beneficiary designations—to make progress feel less daunting. Life changes happen frequently, making regular updates essential to ensure alignment with current goals.
We also explore the art of meaningful giving, whether to charities or family. Simplifying the process—such as focusing on a few causes or using donor-advised funds—can make giving more impactful and less stressful. Transparent family conversations around financial goals can further reduce misunderstandings.
Finally, we discuss achieving better work-life balance by prioritizing personal goals with the same importance as professional ones. Amy shares her own experience of scheduling personal tasks, like watering plants, alongside work obligations. She emphasizes making vacation planning and funding non-negotiable and leveraging delegation to minimize stress.
The overarching message is that financial success in 2025 depends on small, consistent changes, intentional planning, and balancing priorities. For personalized support, we encourage you to connect with Thimbleberry Financial, below.
ThimbleberryU 126 - Tricks to Make 2025 Your Most Financially Successful Year Yet
Speakers: Jon Gay & Amy Walls
[Music Playing]
Jon Gay (00:09):
Welcome to ThimbleberryU, I'm Jon Jag Gay. Amy Walls from Thimbleberry Financial is with me as always. Hello, Amy.
Amy Walls (00:15):
Hello, Jag. Happy New Year.
Jon Gay (00:17):
Happy New Year to you too. So, as we turn the calendar to 2025, a lot of folks have a New Year's resolution regarding finances, doing a better job with their finances – so today, we're going to talk about ideas you might not have thought of or know how to implement as we get into 2025.
Amy Walls (00:33):
I like the word “tricks.”
Jon Gay (00:37):
Or hacks even.
Amy Walls (00:38):
Yep. Exactly. What are the things that might be right there that we just don't think to do?
Jon Gay (00:44):
The usual stuff, we'll get that out of the way. We always hear save more, spend less, plan ahead. That's like table stakes here. But what are some of these tricks or hacks that go beyond the basics? We'll start with the idea of maximizing tax advantage contributions. Why is this so tricky for people, and how can they make it easier?
Amy Walls (01:04):
So, here's why I think it's tricky, is to save more, we're giving up something else, meaning life today, and that's hard. So, I'm going to say I sometimes am comfy and cozy, and the last thing I wanted to go do before I actually turn on the lights is go brush my teeth.
Jon Gay (01:26):
I see where you're going here.
Amy Walls (01:29):
And so, maybe in the new year, I should set a goal of, “Hey, brush my teeth at night. I'm really great about it in the morning. Brushing at night, not so much, so I need to start with a goal and a reward.” So, I'm going to brush my teeth at night for five nights in a row.
Boom, I give myself a reward to do that, and we can build those habits. Now, really, I'm not that bad at brushing my teeth, but we do small things like brushing our teeth regularly, it becomes the norm. It's not a big deal.
Jon Gay (02:03):
You're developing a habit. For me, it's like working out. If I get out of the routine, it's so hard to get back on that bike behind me, but if I do it enough days in a row or work out in general, enough days in a row, my body starts to do it.
Amy Walls (02:17):
Absolutely. So, in this area, if there's room to be contributing more, and you're not there yet, maybe that is every month on the first of the month, you increase your contribution by 1%, or maybe it's every quarter you do that.
So that you get used to it, but you have a pattern and you set that into your calendar to make it a habit. Just like I might set an alarm on my phone to brush my teeth at night, rather than getting into bed, to remind myself I am building this.
Jon Gay (02:51):
You're establishing a habit that future you will thank present you for.
Amy Walls (02:56):
Absolutely. And so, with that, it's one, defining what the thing is: I'm brushing my teeth more frequently at night, I can say I've done it. I'm going to save more into my 401(k) by increasing my contributions 1% every month. Now, the next question is, how do I do that? How do I make myself remember? If it were just that easy, I'd have already been doing it. So, “Hmm, I'm going to brush my teeth after dinner. That will also stop me from snacking.”
Jon Gay (03:32):
Theoretically.
Amy Walls (03:34):
Theoretically – before I get too cozy and don't want to get up to go do it, I can do this each month when I pay the credit card bill that I put all my regular expenses on.
I will take the step of increasing my contribution to my 401(k) 1%. I will give up my coffee three times a week, and that will allow me to feel more comfortable with increasing that when I pay that credit card off.
Jon Gay (04:04):
Okay. You're giving yourself permission to do something.
Amy Walls (04:07):
Absolutely. And you're setting a path for how you're going to do it.
Jon Gay (04:11):
I like it. Amy, I know at Thimbleberry, you do a lot of work in the tech sector, and in that tech sector, stock options, RSUs, those topics can be overwhelming. I would suggest if you're not familiar with those terms, go back and listen to many, many previous episodes we've done on them. But what are some tricks as we head into 2025 to handling them strategically?
Amy Walls (04:32):
This is one of the most emotionally charged areas of financial planning, especially for those working in tech. People feel really loyal to the company they're working for, or they're worried about selling at the wrong time. They're not worried about selling at the right time.
But especially when you know these conversations are happening around the water cooler, or the coffee pot, or in the Slack channel. What I think we can do here is we can reframe it. Think of company stock like eggs in a basket, if all of your eggs are in that basket and you drop it, boom-
Jon Gay (05:04):
That’s a mess.
Amy Walls (05:05):
You risk losing everything, and then that has bigger disasters. As I was actually saying that, I'm imagining a day that a blackberry smoothie when I only had a moment that I made for breakfast, dropped all over our white kitchen and it needed to be cleaned up and I had a meeting to run to, it's a disaster.
So, diversifying maybe in this case, eggs and toast might have been a better option-
Jon Gay (05:37):
Or smoothies and toast.
Amy Walls (05:38):
Having more than the company stock is a different … it's just the way to reframe and think, “I don't want to have everything in this one company.”
Another way is look to the people you know that you also value. Whether that's your financial advisor or it's someone else within the company who you know has done a good job, and who you know has done the thing that you know you need to do.
Don't ask the person who hasn't done it; ask the person that you know has done it and how they approached it and why they thought about it the way they thought. That can help you feel less alone, and obviously, give you some new ideas to consider.
Another trick here, and I think this is the big hack on this once you get past the emotional – is to already know where the proceeds are going to go from selling that stock before you sell it. So, perhaps, this money is for my future. I have a diversified portfolio over here on the side, I sell it, I get rid of this one orange egg, lots of this one orange egg, and I'm going to go buy eggs of all sorts of colors.
And that can really make that transition so much easier because one of the fears I often hear is that, “Ooh, I might spend it in the meantime.” So, know where it's going and know how you're getting the money over there.
Jon Gay (07:08):
Yeah, that planning certainly helps and let's zoom out on that topic, actually. Planning could really help with the emotional side when it comes to this stuff in general.
Amy Walls (07:17):
Absolutely. Planning reduces “what if” scenarios, and I think most of us can say our minds have raced at some point with “what if” scenarios. They are the rabbit hole of rabbit holes.
Jon Gay (07:30):
It's the anxiety character from “Inside Out 2.”
Amy Walls (07:34):
Absolutely. So, when you know your sale and reinvestment plan, it's so much easier to let go of, “But what if the stock goes up the day after?”
Jon Gay (07:45):
What if it goes “to the moon” as the memes say, for sure.
Amy Walls (07:47):
Absolutely.
Jon Gay (07:50):
And it seems like not a bad problem to have on the surface, but what about people who have excess cash flow but are uncertain about investing or maybe worried, like you said, that anxiety, that they may not have the same extra cash later?
Amy Walls (08:01):
It's a great question. It is a definite big mindset hurdle. The trick here, the hack, is to make decisions feel smaller and less permanent. For me, even with a hack, I like knowing the psychology behind it, some people may not want to. So, sorry if I am telling you how to talk yourself out of this, but I happen to find that to be something really valuable.
Think of investing like you're planting a garden. You aren't going to go out and plant everything in your garden at one time. You're going to go out and you're going to start with your first crop of the season, and you're going to put a little bit in and you're going to leave room for the next things.
Jon Gay (08:48):
So, what you're saying is you're going to diversify.
Amy Walls (08:51):
Well, yes. But even beets, for example, there's a couple different times of year when you can plant them because you don't want to eat beets nonstop when they're ready. You want to be able to have that food at different times during the year.
Jon Gay (09:09):
I detest beets, by the way, but we'll go with the analogy here. I'll leave that out of it.
Amy Walls (09:14):
I'm a fan. So, you know you're going to plant a little of the garden now, it's not time for tomatoes. The tomatoes are going to come later and so on and so forth. And so, by taking those little steps, you have the option to stop, you have control. And as you start to see the first things grow in a garden, it's more exciting, and you become more ready to see the next thing.
So, if you've got excess cash and you're afraid to get it invested or put it somewhere, the more you set it there and the more you start to see it grow, and that you don't need to dip into it, the more inspiring that is to do more.
Jon Gay (09:55):
I like it.
Amy Walls (09:56):
Ways to now make that easier – and some people are okay with saying, “I've got $50,000 extra outside of my cash reserve, let's just get it all invested.” That is not right for everybody. So, maybe it's a monthly transfer into the investments. You say, “I'm going to start with $5,000 a month,” until you have it all there and you can turn it off at any point.
Jon Gay (10:25):
Here’s a big procrastination topic, Amy, and that is estate planning. Nobody wants to think about this.
Amy Walls (10:32):
Oh, you're so right, Jag. Alright. So, a couple things, do some annual check-ins. Have a pattern. I'm a huge process person, so if I have a plan and a checklist that every month these are the things I do, I'm probably going to be much more successful than if it's floating in my brain.
So, schedule a month each year that that's when you're going to review your estate planning documents. If it's overwhelming, pick one piece of it. So, these are conflicting hacks in what I'm saying, but maybe it's just, “I don't really want to tackle this. I'm just going to start by looking at my beneficiary designations, and I'm going to get those updated.”
70% of people don't update their beneficiaries after major life events. So, knowing that and knowing that American adults have a major life change on average once every three years means that doing this is very important.
Jon Gay (11:30):
Another thing people really have hesitation about Amy, is giving meaningfully to family or causes. They're not really sure how to do it. Any tricks on that side of it?
Amy Walls (11:39):
Yeah, giving doesn't have to be complicated, and I think this is where it often is. Sometimes people feel like they're setting an expectation, that they'll be doing this going forward, so I think the simpler you make this, the more rewarding it feels.
So, start by focusing on, if it's charity, one to three causes or goals, lets you just put your energy there and really see your impact. So, maybe use donor-advised funds. So, you got started with having money set aside for charity but you can decide actually what charity is going to get it later. So, it takes the pressure off of making decisions immediately.
I talked about when you're giving to family, it can set expectations, but maybe just have family conversations around goals and aspirations, and also, their charitable giving and their desires to give money to people that can help avoid some financial strain.
Jon Gay (12:38):
Alright. Final question, Amy: work-life balance. Oh, that is such a challenge for, I would assume everybody listening right now.
Amy Walls (12:45):
Absolutely. I think the trick here is treating personal goals with the same importance as your professional ones. Now, what our listeners can't see because we have not transitioned to video, is that behind me are a million plants.
And I have struggled with keeping plants alive in the past. But at work, I have a task list on a rotation each week, each month that I go through, as well as kind of the one-off tasks. You know what I did because my plants were important to me? I put watering them on my weekly list.
Jon Gay (13:22):
There you go.
Amy Walls (13:23):
For a very specific day, so that my office is happy. So, I'm happy looking around at the plants. So, work-life balance, treat your personal life like your professional life. Give your commitments the same importance. That means blocking vacation time on your calendar before you do anything else. Make it a non-negotiable part of your year, and then go seek that time off. Part of work-life balance means setting aside the money to have the fun.
Jon Gay (13:52):
For sure.
Amy Walls (13:54):
So, maybe earmark a bank account specifically for that purpose and set money aside on an ongoing basis.
Jon Gay (14:02):
I like that.
Amy Walls (14:03):
Another option: delegate. Hire someone to plan the trip for you so that you can enjoy it more and don't have the stress of needing to pick everything yourself, if that's what's getting in your way.
Jon Gay (14:14):
I'm so bad at delegating when it comes to work, but now, that's the great idea. Delegate work life and personal. It goes back to the same theme you're talking about here; put the same emphasis on your personal as you do on your professional.
Amy Walls (14:25):
Absolutely. The goal of this whole podcast is help you achieve what you want to your financial success in 2025.
Jon Gay (14:33):
And that's going to look different for everybody. So, if one of our listeners wants to come talk to you and your team, Amy, at Thimbleberry Financial, about their specific goals, how do they best find you?
Amy Walls (14:41):
They can reach us online at thimbleberryfinancial.com or by giving us a call at (503) 610-6510.
[Music Playing]
Jon Gay (14:49):
Awesome stuff as always. Again, Happy New Year, we'll talk soon.
Amy Walls (14:51):
Happy New Year. Thanks.
Voiceover (14:53):
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.