In this episode of ThimbleberryU, we step behind the curtain of financial planning to unpack what makes a financial plan succeed—and just as importantly—what can derail it. We kick things off with a discussion about structure and intentionality. Amy Walls explains how her team at Thimbleberry Financial organizes their schedules to be proactive and client-focused. By setting clear availability and reserving space for strategic planning and internal work, they're able to show up fully prepared for client meetings and respond effectively in between.
We then explore how life events, especially the big and unexpected ones, impact planning. Medical diagnoses, large expenses, home changes, or receiving an inheritance—all of these can affect a financial strategy. We emphasize the importance of timely communication: the sooner we know, the better we can adjust the plan. Amy also reminds us that “big” is subjective. Our financial mindset and values shape how we define major changes, and that’s part of the data that matters, too.
Speaking of data, we clarify that every document request serves a purpose. Whether it's retirement summaries or tax returns, we ask only for what might improve the accuracy and depth of our advice. Sometimes, those pieces of information reveal benefits or pitfalls that clients weren’t even aware of, significantly shifting their trajectory. Taxes, in particular, often catch people off guard, and without returns in hand, it’s tough to diagnose the real issue.
As we dig deeper, we confront ambition versus reality. When clients want to retire early but aren’t on track for a more standard goal, we stress the importance of honest evaluation. If you're not ready to make the changes needed to hit the baseline, it's not useful to explore stretch goals. It’s not about being harsh—it’s about using everyone’s time wisely and avoiding decision fatigue.
We close by highlighting what a successful client-advisor relationship looks like. Clear communication, timely data, and realism about trade-offs are essential. When clients are engaged, responsive, and honest about what's possible, we can offer not just sound advice, but advice that truly improves lives. Financial planning works best when both advisor and client show up ready to collaborate with transparency and intention.
ThimbleberryU 135 - What Makes a Financial Plan Work and What Gets In The Way
Speakers: Jon Gay & Amy Walls
[Music Playing]
Jon Gay (00:08):
Welcome back to ThimbleberryU, I'm Jon Jag Gay. I'm joined as always by Amy Walls from Thimbleberry Financial. Hello, Amy.
Amy Walls (00:13):
Hi, Jag.
Jon Gay (00:14):
I have to say before we start today, I work with a bunch of podcast clients. As you know, I work on a bunch of podcasts, and you may be my most organized client of all of them.
You have systems in place for everything. You book your podcast recordings for the entire calendar year before the year starts. You are so well-organized, and I'd recently took an entrepreneurship class and I have to admit, I'm envious of you and your organization and your systems.
Amy Walls (00:42):
Thank you, Jag. That's a huge compliment.
Jon Gay (00:44):
And that actually leads into our topic today, which is going behind the scenes of financial planning and the way you work with clients, what actually helps a plan succeed, and what things can kind of get in the way and unintentionally slow them down.
Amy Walls (00:55):
Well, Jag, that is the reason we have systems, because we have to be able to be proactive. We know that people's lives can be messy at times. There's so much we can do to help, and by being proactive, we can do even more. And I'd say we can only build great financial plans for our clients with good input.
So, this episode, as you've alluded to, it's all about how to make your plan work better. And just by understanding a few key parts of the process for clients, I think they can play an even better and more active role in getting more out of the relationship.
Jon Gay (01:33):
We'll come back to that data piece as the old cliche goes, garbage in, garbage up. Let's talk about process first. Let's start with the planning schedule. How does your team manage its time?
Amy Walls (01:43):
So, our schedule is quite structured. It's structured in order to give each client thoughtful, high-quality advice. So, we look ahead, we know we have a maximum number of clients that we will work with.
We hold up meetings Tuesdays through Thursdays during business hours. Mondays and Fridays we reserve for other things, case work. That's what we call analyzing data modeling situations, planning behind the scenes, improving these processes that allow us to better serve clients.
And also, the internal meetings that of course, every organization needs to have to help keep our team aligned. And so, that schedule is incredibly intentional. I absolutely understand that Tuesdays through Thursdays don't work for everybody. We also know we aren't here to serve everybody. And I don't mean that rudely, I mean that in a very positive way. We can't be all things to all people.
We do have a limited schedule with the intention of carving out time to take care of our clients outside of when we're in meetings. And what it means is when you're in a meeting with us, we're fully prepared. And when you reach out between meetings, we're better able to respond with care.
Jon Gay (03:00):
I read somewhere that if you are trying to multitask and say you're working on email and then you have to take a phone call about something else, it takes not only the time it takes you to get off task, but then you have to reorient yourself and refocus on the previous task you're working on.
So, I like that idea that you have dedicated time set aside for certain tasks. And you and I have talked about this in the podcast before, when you say you're not the right financial advisor for everybody, you have a really structured system- that is a proven system- that works well for you and your clients, and that might not be a good fit for all clients.
So, if someone tries to book a meeting last minute or outside your schedule, I've got to imagine that's going to interfere with your work for your other clients.
Amy Walls (03:39):
It can. Now, that said, if somebody has something big going on, we'll jump on a quick phone call. We can schedule those last-minute phone calls for a short period of time to understand what's going on, get details, talk through something. Maybe someone's had a life-changing medical diagnosis. And we need to talk through that, their kid's going through something – whatever it is, we're happy to do that and we reserve time in the calendar to do that.
One of the things that sometimes comes up is clients may be delayed on getting us their annual data. And when that happens, yes, that means that we’ll kind of flow over into time allocated for other clients. And what that might mean is that client's going to end up waiting longer to get their information to get recommendations back.
Jon Gay (04:27):
You mentioned a major issue if something comes up, you mentioned a medical diagnosis as one example. What other kinds of life events that would pop up and should a client immediately contact you and your team about?
Amy Walls (04:39):
I'm going to be pretty generic on this, Jag. Any big change that could affect their financial life, So, medical issues, obviously, one; large expense, another – those could be the medical care, family support. Maybe it's a home change for some reason. But it's important to know the cost, at least an approximation of the cost.
We understand clients don't always have that nailed down. We're going through a remodel right now, we had a pretty good idea of what that was going to cost and a few things have popped up, and that budget has changed.
And in addition to the cost, what the timeframe is. Some things are one time, some things are ongoing annually, some things maybe every so often, it's going to pop up. But some idea of generally what as a client you're thinking something is going to cost.
Another big one that comes to mind would be receiving an inheritance. One, to know you're going through the death of someone that you are close to. That's important. But we also need to know what kinds of accounts are involved.
Are these all IRAs or employer-sponsored retirement plans? Do you have money coming to you from a trust or from taxable brokerage accounts where you were named as a beneficiary? All of that plays a role.
Jon Gay (05:52):
So, you mentioned big changes, big life events. Big is a subjective term. I'll say it depends before you can say it this time Amy, but big means different things to different people, right?
Amy Walls (06:02):
Absolutely, correct. Some clients feel panicked about a $15,000 surprise. Others think $75,000, no big deal. It'd be easy to jump to the conclusion that, well, that's a matter of how much money you have.
Yes, that can be true. It's also about mindset. We've talked about ants and grasshoppers before. Ants collect and collect and collect, and grasshoppers spend. The mindset of how you think about your money and think about these expenses in relation to your values also defines “big.”
So, let me tell you kind of a generic story. A client wasn't sure if a possible inheritance was relevant to their plan, but they let us know anyway. They said, “Hey, this is likely going to happen at some point.”
The early heads up and just understanding the dynamics of age and health of the person the money was coming from (not that anybody was absolutely saying we are counting on it, but it's here kind of potentially in the back pocket) let us design their plan knowing that that was a possibility and prepare really for their goals in a little bit of a different way.
It also let us provide some education ahead of time so that when the family member passed and they started receiving information, and dare I say paperwork, they weren't nearly as overwhelmed. Jag, earlier we talked about we want to be preparing people ahead of time for what's coming and this is a great example of how we might do that.
Jon Gay (07:40):
Makes sense. You mentioned details. What are the typical times of documents you're going to ask for from clients and why?
Amy Walls (07:47):
Here's the deal, we will never ask for something unless it might impact your financial plan. We don't want extra data (laughs). We don't want to know things we don't need to know. We're not looking to waste your time or our time.
So, basically, it's that we either know it's information that affects a financial plan or we think it may impact a financial plan. So, a client may not know why we're asking. Typically, we'll try to explain why or think it's very obvious why, and sometimes, we're not a hundred percent sure that we we're asking for matters yet, but we ask because it might matter.
So, if we paint an analogy here, think of your financial plan like your health. If you go to your doctor, let's say you call your doctor because you've had a stomach ache. You don't want that doctor prescribing you medications over the phone. They wouldn't really be doing their job, but they might give you some generic advice. If they think it's serious, you're going to go in and they're going to do a physical and they may get some lab work.
Sometimes, they do that physical or they do that lab work, and everything looks great. But the important part here is if there is something important, we want to catch it. And that's why they do the physical and the lab work.
We're looking for the anomalies, and that's sometimes why we will ask for data that we are not entirely sure we need or how we're going to use it because there's something that could be there that plays a role.
Jon Gay (09:27):
Bottom line, better to have data that you don't need than not have data you do need.
Amy Walls (09:31):
Absolutely. So, another example, we had someone wait months to send us a summary of their retirement plan. When we got it, we discovered that they had a very important to them benefit that they didn't know they had. Ultimately, that changed their retirement planning quite a bit.
So, I think the takeaway here that I hope our listeners get is that if us, as your financial advisor, financial planner or someone else is asking for the data, it's not to create busy work for you. It's because your plan might be better with the information.
Jon Gay (10:06):
Very important. You mentioned retirement plans and other pieces of data that you need as a team. Something I think that really catches people off guard is taxes.
Amy Walls (10:15):
Yes. Here's something that can happen somewhat frequently. A few years ago, when the current tax bill went into place, we added a lot of these calls that particular year, last minute. Someone calls shocked because they got a $20,000, $25,000 even bigger tax bill. But we haven't yet seen the tax return. And that means we don't know what generated the tax bill, we don't know if the tax bill is federal or state.
When I said we don't know what generated it, what I'm really saying is, was it stock compensation like RSUs? Was it something related to business income? Did something get counted incorrectly on their taxes? Maybe it's because we didn't realize with something changed that we didn't know about and they stopped their retirement plan contributions and that shot up their tax bill.
So, without having the tax return and its schedules to be able to review and understand more of the situation and maybe how it aligned with what we were expecting, all we can really say is talk to HR, your CPA. And we know that's not very helpful, but it's what we're limited to without information.
Jon Gay (11:25):
This speaks to having an entire team, having a financial planner, a financial advisor, but also having a CPA to sort of work in tandem because you each handle different pieces of this and having all that information together is key.
Amy Walls (11:38):
Yeah. The more we know, the more accurate and proactive our advice can be. And we can work with those other professionals.
Jon Gay (11:45):
Okay. So, stepping back a step, Amy, what happens when somebody wants to hit an ambitious goal but they're not even on track for like a more modest one?
Amy Walls (11:53):
Jag, I try to always be honest, and here's where I'm going to be really honest. If you're not on track for a less aggressive goal, what you're calling a modest goal, like retiring at 65, and you say you can't or won't make the changes necessary to hit that goal of retirement at 65, then quite frankly, it's not a good use of anyone's time, yours or ours, to explore something even more aggressive like retiring at 55.
Jon Gay (12:20):
Harsh but makes sense. Can you give me a little bit of an example here?
Amy Walls (12:23):
Yeah. So, a client says, “Hey, can I retire at 55?” In the planning we've already done we say, “Remember how you were going to need to reduce expenses and save more? We talked about it being this much for those numbers to get on track for 65. And you'd said, ‘I just can't do that. I don't have enough wiggle room. Like my expenses aren't going to change, so I'm not going to be able to save that extra.’”
Then if let's say that was $40,000, they needed to reduce expenses by and save the difference, well, to retire at 55, that might be $80,000. So, if $40,000 wasn't possible, what is the benefit to looking at what it takes to get to 55 at this point? I'm all for looking at those goals, but let's also take incremental steps if we know something's not possible to get to the next closest thing that you are willing to do.
Jon Gay (13:26):
I think you hit the nail on the head a moment ago when you talked about time. This isn't about just being harsh for the sake of being harsh. It's really you want to protect the time of the client to not spend that time- time is a finite resource- on something that's really not feasible.
Amy Walls (13:40):
That's absolutely it, Jag, along with another concept. So, not only are we protecting that client in terms of time, but the time to analyze all of these things when there isn't something that can actually be done actually takes away time from all of our clients. And so, we're going to draw that line in the sand for any client who wants to explore something that they've already told us they're not willing to take the steps to reach.
I said there's one other piece to that, and that is frustration. I think one of the hardest things for people from my experience as a financial advisor is to be living in limbo. When people are living in limbo, they feel like they can't make decisions. And one of our core values is to simplify.
So, if I say to you, Jag, “Hey, you need to save $40,000 a year to get on track to retire at 65.” That means you're going to have to reduce some expenses, we're already being very efficient with the savings you're doing. You also want to look at 55, well, here you need to do 80,000, maybe even 90,000, and here's where that would all go.
What I've really just done to you psychologically is very likely overwhelm you and given you decision fatigue. And so, now, you're just going, “I don't have any clue what to do because I'd really love this 55, but I can't even do the 65, and so I might as well just throw up my hands rather than focusing on, okay, here's what it takes for 65, what baby steps can we take to start building towards this as our starting point.”
Jon Gay (15:17):
So, we've talked about some common areas where there can be friction and where it may not be a good fit. Let me flip it around before we wrap up, Amy, and say, what does a successful partnership between a planner and client really look like?
Amy Walls (15:28):
Before we bring on a client, we always talk about fit. That involves communication. Every relationship is about communication. Clear communication, say what you mean, do what you say, all of those things.
So, a little bit outside of that, tell us what's going on. Tell your financial advisor what you have going on, what you think may be coming because not everything is a straight road. And so, those things could be beneficial and may allow you to make some really great choices and decisions and pivot. Send the documents that are requested even if you don't know why they matter.
And then be realistic about what you're willing to change. The numbers won't move if nothing else does. And so, it's important to say, “I am drawing a line there.” You also have to understand that if you draw the line, there may not be anything else the financial advisor can do in terms of strategies to get you on track for the goal that you're aiming for.
And with that, we'll do our part with strategy insight and the planning. Bottom line there is that your actions as a client do drive the results of being on track for your goals. And that's true whether your goal is to retire early, help family financially or just have more peace of mind about money.
Jon Gay (16:46):
Absolutely fair. This has been really helpful today, Amy, because it kind of gives a look at that advisor client dynamic. And when it comes to financial planning, it really isn't just what your advisor does, it's how you show up yourself as a client in the process.
Amy Walls (16:59):
Jag, I like how you just said that. And you're right, when you're open, responsive, and honest as a client about what's possible, we can give the best advice. And that advice isn't just good, it's meaningful and real, and that's when financial planning actually changes lives.
Jon Gay (17:15):
That is a great place to leave it. If somebody's interested in working with you and your team at Thimbleberry Financial, Amy, how do they best find you?
Amy Walls (17:21):
They can reach us at (503)-610-6510 or by going online to thimbleberryfinancial.com.
[Music Playing]
Jon Gay (17:29):
Talk again in a couple weeks.
Amy Walls (17:30):
Sounds great, Jag.
Voiceover (17:31):
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 FINRA/SIPC, advisory services through Cambridge Investment Research Advisors, Inc., a registered investment advisor. Cambridge and Thimbleberry Financial are not affiliated.