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The Financial Planning Process, Step-By-Step | AMA #13 - E129

February 04, 2026 / 41:18

This episode covers financial planning, the differences between a portfolio and a financial plan, and advice for young investors. Jesse Kramer answers listener questions about financial planning processes and strategies.

Jesse begins by clarifying the distinction between a portfolio and a financial plan, emphasizing that financial planning encompasses more than just investing. He highlights common misconceptions and the importance of aligning financial goals with personal life.

Listener questions from Mary and Bob prompt discussions on how to build a financial plan from scratch and what young adults should focus on financially. Jesse outlines key elements of financial planning, including understanding cash flow, setting goals, and the importance of investing early.

Jesse also addresses a question from Bernard, a financial planner from Ireland, regarding the challenges of getting clients to prioritize retirement planning. He shares insights on human behavior and the emotional aspects of financial planning.

The episode concludes with Jesse encouraging listeners to submit their questions and subscribe to his newsletter for ongoing financial education.

TLDR

Jesse Kramer discusses financial planning fundamentals and answers listener questions about investing and retirement strategies.

Episode

41:18
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Welcome to personal finance for long-term investors, where we believe Benjamin Franklin's advice that an
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investment in knowledge pays the best interest both in finances [music] and in your life. Every episode teaches you
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personal finance and long-term investing in simple terms. Now, here's your host,
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Jesse Kramer. Welcome to Personal Finance for long-term investors, episode 129. I'm Jesse Kramer. By day, I work at
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a fiduciary wealth management firm helping clients nationwide. You can learn more at bestinterest.blog/ blog
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back/work. The link is in the show notes. By night, I write the best interest blog and I host this podcast.
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[music] I also put out a weekly free email newsletter, all of which help busy professionals and retirees avoid
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mistakes and grow their wealth by simplifying their investing, their taxes, and their retirement planning. By
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the way, what is financial planning? Is it just a a fancy word that people throw
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around for investing? What does a financial planner actually do? What does the financial planning process look like
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in detail? Those are the kind of things we're going to be diving into detail
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today on today's AMA episode. Thanks to great questions from listeners like you.
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Before we get into that topic though, we do have a quick review of the week from
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Nick Reviewer 77. And Nick says, "Top tier finance education podcast. Jesse
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has a knack for making even the most difficult and complex financial topics easier to learn and understand. He
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covers great topics and has on fantastic guests. I especially liked his recent episode with Andy Hill. Well, Nick,
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thank you for the kind words. I'd be happy to send you a super soft t-shirt.
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Just shoot me an email to [email protected]. And by the way, listeners, that episode
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that he referred to with Andy Hill, that was episode 123123. And now, let's get going with the AMA,
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the basics of financial planning. That's kind of what I'm calling this in my
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head, but we'll get into some serious detail. It's not that basic. And we
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start with a great question from Mary. And Mary's question is, are a portfolio
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and a financial plan the same? I mean, it's just a terrific question. A great
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way to start this episode, Mary. I think it's easy to think that a portfolio and
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a financial plan are the same thing. They're certainly not. But the misunderstanding totally makes sense.
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And I think this misunderstanding exists, you know, in in everywhere you look really. And the main reason why or
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at least one of the main reasons why is because the most popular personal finance topics that you see on the
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internet, in books, in print journalism, anywhere, the most common topics are budgeting one and investing two. I mean,
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investing is for sure one of, if not the single biggest topic. I think the term financial planning doesn't often get
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used when someone is just starting out and putting together their budget. You know, that's not really where financial
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planning gets applied, but then suddenly you're introduced to investing and you
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start hearing this phrase financial planning. And I'm happy to, you know, confess that I certainly use the term
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financial planning without always explaining it. So, we don't hear the explanation of what financial planning
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is. We hear it associated with the idea of investing and next thing you know we think that investing and financial
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planning are one and the same kind of 100% overlapped with each other. By the way, I actually conferred with some of
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the the AI large language models, you know, chat, GBT, Gemini, those guys. And I asked them actually to scour the
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internet and rank the most popular personal finance topics. And they came back to me and said, "Number one,
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budgeting and saving. Number two, investing. Three, retirement planning, then debt management and credit, taxes
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and tax planning, emergency funds and financial safety nets, insurance and risk management, financial goal setting
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and planning, estate planning and wealth transfer, and last was banking and financial products like accounts,
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mortgages, and loans. So, are they right, are they wrong? I'm not sure. But the point is that investing is a topic
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that gets talked about a ton. After all, who doesn't enjoy the idea of multiplying their money? Who doesn't
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want to turn $1 today into $10 tomorrow, I suppose, as long as tomorrow as 30 or
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40 years from now? Investing is cool, right? Investing is cool. And investing is certainly necessary. It's very
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important. It's definitely part of financial planning. So, that's a big reason why investing gets so much press.
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And allow me to be a little bit meta here. Investing is where the money is. Literally, the US stock market is at $62
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trillion of value. As I write this, the whole world, the global stock market is about double that, on the order of $125
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trillion in value. That's a lot of money. And if you can tap into that pool of money in some way, wow, do you open
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some doors. Perhaps you're an individual investor like many of you listening.
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Maybe you run a TV channel like CNBC or a service like Bloomberg or you run a brokerage like Fidelity or Vanguard. You
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work as a stock broker on commissions or the list goes on. But when you're tapping into trillions of dollars, even
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in some small way, you might have a vested interest. You do have a vested interest to make this thing investing,
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you know, seem important. A vested interest to get people to care, to pay attention, to participate, to compete,
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to win. And one of the results from this line of thinking is that there are many
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lay people who out there, they think investing is the thing, right? Investing is the thing. That's what I've been led
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to believe. I've been led to believe it by Bloomberg and by CNBC and by the Wall
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Street Journal. All these people are talking about investing like it's the most important thing. And my profession,
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the the professional financial services industry, hasn't exactly done too much
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to avail itself of that reputation. For decades and decades, the financial services industry meant exactly two
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things. It meant people slinging insurance products for commissions. And it meant stock brokers slinging the hot
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stock picks again for commissions. Retirement planning or digging into your cash flow or estate planning, when to
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claim social security, right? That was so far down the priority list for most financial adviserss that it literally
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never came up. Even today, despite everything we know, and I mean everything you and I know about the
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world of investing, the average financial adviser is still leading with either a product like whole life
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insurance or an annuity or they're leading with investment management. You know, we build a better portfolio than
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the other people. The vast vast minority of financial planners and financial adviserss lead with some sort of process
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instead of a product. aka let's actually build a financial plan together before
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we for example make investment decisions for you. Something like about 10% of the
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industry operates under some sort of fee only management structure. The other 90%
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is in some form working off a commission or incentivized to sell a specific product or a product set. And that 9010
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split, it's not a perfect model to separate the good planning focused advisers from the others, but it is a
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decent place to start because if someone is in that 90% incentivized to sell certain products, there's a better
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chance that any sort of financial planning they offer is going to be steered toward that particular product.
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And that right there, that's the whole reason why are you a fiduciary? That's
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why it's a good question to ask because at the very least, that's not a perfect
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filter. I've talked about that here before, but it's a solid filter. It's a
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good place to start. But anyway, digressing a little bit back to the program. I get why the world thinks that
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investing is the main course, right? I get why people think that investing is financial planning. But here's a
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definition of financial planning that I love and I think it goes way beyond just
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investing. A very simple definition is that a financial plan aligns your money with your life. A more nuanced
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definition is that a financial plan aligns the many elements of your personal finances and it aligns them
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with your goals and your desires and your dreams. A portfolio alone does not do that, right? An index fund alone
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certainly does not do that. So, think of this. I I like to dive into some questions that a financial plan does
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answer, but that a portfolio does not answer. So, here's the first one. Can I
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actually afford my lifestyle now and in the future? A financial plan will model cash flows and spending and inflation
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and income to answer whether your lifestyle is sustainable over decades. How about uh when can I safely stop
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working or at least when can I start to work less? A good financial plan connects savings rates and future income
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needs and future tax needs and longevity risk to determine some sort of realistic
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retirement timing or realistic glide path timing. how much risk do I need to take instead of just kind of how much
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risk do I need to tolerate. A financial plan should measure the required rate of
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return of a portfolio and shows whether aggressive or conservative investing is mathematically necessary. And the list
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goes on from there. You know, where should each dollar be saved or invested and why? How much can I safely spend
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each year without running out of money? How will taxes impact my wealth over my lifetime? Are my insurance decisions
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right? Insurance, is it protecting my plan or is it actually harming my plan? What happens with my money when I'm
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gone, when I die? And is that aligned with my wishes? In that list of questions, we've aligned the personal
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financial ecosystem of a person and in some way we've thought about their goals, their dreams, their desires, and
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and the timeline to get there. We're thinking about cash flow both today and
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in the future. We're thinking about all sorts of different risks and how to mitigate them. We're thinking about
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work. We're thinking about retirement. We're thinking about death. We're
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finding the balance between some different options to get people from not only A to B, but also maybe to C and to
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D and maybe a little bit to F2 if they want. Now, many of those questions, all those questions can lead to answers that
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then get incorporated into portfolio decisions. Absolutely. This whole example, it's a little bit like saying,
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is a meal the same thing as a diet? And is a diet the same thing as a healthy lifestyle? I bet most of us might
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answer, well, you know, good nutrition is certainly part of a healthy lifestyle and and one healthy meal is this small
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but solid building block into good nutrition, but we should still differentiate between one healthy meal
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and a complete healthy lifestyle. Similarly, I'm going to say that, you know, a lowcost, broadly diversified
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index fund, that's a great building block of just about any good portfolio. And I would also say that investing and
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portfolio management and all the little assorted investing topics like rebalancing and gain harvesting and
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those are all important aspects of financial planning. Absolutely 100%. But a portfolio is not the same as a full
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financial plan. So awesome question, Mary. Here's a quick ad and then we'll
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get back to the show. Every January we make the same promises. Eat better, work out, read more books, and of course
00:09:59
something about money. You know, this year is the year I finally get my retirement plan organized. Personal
00:10:05
financial planning is one of the most common resolutions out there. So, if 2026 is a year you want real clarity,
00:10:11
serious financial planning, a full review of your complex financial picture, or just someone to help you
00:10:15
make good decisions with confidence, I'm currently accepting new clients. You can
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head to bestinterest.blog/work and fill out the short form. Let's make better finances the resolution that
00:10:25
actually sticks this year. And let's continue this topic as we pivot to Bob.
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Bob asked, "Jesse, we're pretty far along in our financial plan. At least I
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like to think so, but my two kids are mid 20 years old and at the other end of the spectrum. I'm encouraging them to
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start investing and they are listening. But where else would you recommend they focus their financial energy?" And I
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picked this question out because it allows us to continue talking about financial planning process, but Bob's
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children give us um like a blank slate to work from. So, let's think about building a financial plan from scratch.
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And rather than saying Bob's kids a million times in this answer, I'm just
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going to be talking to you, the listeners. And and quickly before I get into this answer, I'm also going to give
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a shout out to John from Pittsburgh. John wrote in and asked, "Jesse, as an
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engineer, I feel like you probably have a system or a process in your head when you're working on a client's financial
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plan. Do you mind sharing that on an AMA or is that spilling the secret sauce?"
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So, John, great question. It aligns very much with uh Bob's question about his
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kids. So, I'm going to walk through my financial planning process here, helping
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both Bob's kids and John from Pittsburgh and you, the listeners. Now, I'm an
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engineer at heart. I'm a numbers guy, and my brain is naturally wired to dive
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into the numbers first. But I would really encourage you to start a little bit with the soft side. You know, this
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doesn't have to be some sort of deeply personal philosophical meditation, but
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in simple terms, I would ask you to ask yourself, what's the big goal? You know,
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what's the point? Why are you working hard? Why are you saving money? Why are
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you listening to this podcast in the first place? Right now, at the end of the day, there's a there there, as they
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say, there's a real substance. There's meaning or significance behind why
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you're doing this. Now, being honest, the most common answer that I hear from
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you all and and the answer that I receive in my financial planning practice, it usually has to do something
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with a comfortable retirement or some version of a comfortable retirement. The goal is to set oneself up to live, you
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know, decades of of a good retirement. But that's certainly not the only answer. I literally had lunch today with
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a a great couple and right now they're at a point in their life where their biggest one and two goals involve buying
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what they hope to be their forever home and paying off medical school debt. Like
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those are the big two things that they want to get done right now. Number three somewhere in there is retirement
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planning and and they they know it's important and they know that long-term investing is important and they do want
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to get started on that, but that's not their number one goal right now. They're
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a younger couple recently, one of them's recently out of medical school. And
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yeah, so the goal doesn't have to be retirement. And I think it was really good and really important that we
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grounded their conversation with that first before we really even got into too many numbers. Um, and right, so
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retirement isn't the only answer. Maybe you have a goal around helping your kids. Um, maybe you want to gift them
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money while you live or after you die. Maybe you have a big goal of just reducing your financial stress and your
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financial fragility, you know, as soon as you can while you're still in your
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working years. Maybe you have lifestyle goals. You know, maybe that's really the
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thing that drives you. You want to see the world. You want to golf 100 times a year. You want to spend the summers in
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your camper van. Maybe you want one spouse to be able to stay home with the kids while the other spouse works. And
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you need your finances in such a way so that you can kind of back into that end goal. Maybe you want to start a small
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business. Maybe you want to figure out what to do with all the RSUs that your big tech job keeps giving you. I've got
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one client who I think wants to worship at the feet of Ein Rand and pay no taxes
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for the rest of of their life. You want to reach Coast Fi or Barista Fi or Chubby Fi or maybe some combination of
00:13:50
all three. You know, Chubby Coast to Barista FI, which I imagine is like a a former defensive tackle slinging lattes
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in Santa Barbara. That's chubby coast barista fi. But the point is when you start your financial plan, you want to
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have some idea of what you're working towards. It's like Creed from The Office
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when he asks, >> "If I can't scuba, then what's this all been about? What am I working toward?"
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>> You want to know what it's all about. You want to know what you're working
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toward. That's your first job. And I think it's cool to be a little critical.
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I'm working with a family, for example, who when I first spoke with them, they
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said, "Our goal is to retire with $10 million in investable assets outside of
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their home, $10 million." And yeah, that's certainly a goal. But I was genu
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like it just made me curious the way they kind of um stated their goal. And so I really wanted to know surely some
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thought went into that number. How did you guys arrive at $10 million? Why that number? And the answer was well that's
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puts us in about the top 1% of households. So then I asked another question. Well, okay, yeah, fair enough.
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But like why why exactly do you want to be in the top 1% of households? In my mind, I was wondering is this
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competition? And is that really the family's underlying motivation? But the answer in actuality was, well, we figure
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if we're in the top 1% and we can't retire comfortably, then nobody can retire comfortably. So, if we achieve
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that top 1% net worth level, then we'll be comfortable kind of by definition.
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So, you see what happened there? As we're peeling back the layers of the onion, the real goal wasn't really $10
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million. The real goal was to retire comfortably. And even then, that might not be the true center of the onion for
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them because what exactly does comfortably mean? I'd argue it's kind of a subjective term that every family
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defines a little bit differently. Are they retiring to a particular level of comfort? Are they more concerned about
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running from a certain level of discomfort? Because I'll tell you this, some people say, "Hey, Jesse, we want to
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retire to the lake." But other people say, "I just don't want to have to be a
00:15:43
part-time cashier at Wegman's out of desperation." Right? The first family,
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they're retiring to a particular lifestyle at the lake. The second family simply wants to avoid what they see as a
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negative outcome. And those are very different mindsets. Those are different goals and both of those people might say
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something like, "I need 10 million to achieve my goal, but the underlying financial mindset and and goal setting
00:16:05
is pretty different in those two situations. So again, I encourage you to to be your own critic and uh find the
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center of the onion, if you will, or to sit with your spouse or sit with a best friend. Ask them to interrogate your
00:16:15
thoughts. Why? Why? Why? It makes me think there's the one rule out there to
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ask why five times and you'll discover the real reason for something." I think
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that's worth doing here. Uh, and again going back to the original question, let's say you've asked why enough to
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define why you're doing this. What am I working toward? And next, we need to get
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into the numbers. So, I always start with what I call the big four. Your assets and your debts, your income and
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your spending. Your assets minus your debts, they go on a balance sheet or net worth statement. Your income minus your
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spending. That leads us to net cash flow. And that's the foundation from which everything else flows. From there,
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I'd like to go a little bit deeper into the the current snapshot of what's going
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on. I want to review things like your current account statements from any investing accounts where I look for
00:16:58
things like investment allocation and security selection. I'd want to look at
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your most recent tax return so I can understand more about the money that moves into and out of your life in a
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typical year. Uh your insurance details so I can understand what risks are occurring in your life. Your estate plan
00:17:12
so I can understand what happens upon your untimely passing. and also kind of what some of your underlying motivations
00:17:17
are and and to make sure that what you've told me out loud actually matches what's going on in your estate plan.
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You'd be surprised how many times someone says, "Yeah, you know, it's all
00:17:26
going to the kids." And it's like, well, your will still says it's going to your
00:17:30
wife, so you might want to address that. Anyway, once I feel like I have a good grasp of the current snapshot of
00:17:35
someone's life, I then want to understand how that snapshot will change over time. And I know that your crystal
00:17:41
ball is as foggy as mine. But in terms of your life, you do know more about that than I do. So, you know, you know
00:17:47
the conversations you've had with your spouse. You know about that recurring
00:17:51
anxiety dream that wakes you up too often. You know about what all your friends are doing, how they're all doing
00:17:55
the cool thing, and you've been thinking about doing the cool thing, too. So,
00:17:58
some interesting typical examples might be, you know, you know that your career is going to change in some big way,
00:18:04
likely affecting your income. You know, your family will change, affecting how you spend money, how you save. affecting
00:18:10
your insurance needs, affecting your estate plan. That's really a big one. You know, you're going to receive an
00:18:14
inheritance someday, maybe soon, and that'll inject a bunch of assets you never really considered before. You
00:18:19
know, you'll get married or maybe unfortunately, you know, you'll get divorced. You know that you're getting
00:18:24
sick, that you are sick, and that that maybe will get worse. It's chronic over
00:18:28
time. You'll hit a certain age and be forced to slow down either because that's just the way the rules are
00:18:33
written. You know, maybe at a law firm, you have to retire by 60 at your particular law firm. Okay, that's
00:18:38
interesting. Or you're a contractor. You're a physical laborer in some way
00:18:42
and you know you can't really work until you're 75. Here's a pretty common one
00:18:46
that affects retirees or even some pre-retirees with grown kids is that people in your life will move and you
00:18:52
know that you'll want to follow them. It's pretty common to hear of empty
00:18:55
nesters who say, "Yeah, well, three of my four kids ended up in Sacramento, so
00:18:58
we're moving to Sacramento." The point is that your life is dynamic and the
00:19:01
numbers in your financial plan will certainly be dynamic, too. you know that about better than anyone else. Even if
00:19:07
you aren't precisely sure, that's okay. Any color that you can provide in terms
00:19:11
of how your current state might change over time, that's really good to know.
00:19:16
And then we start to look at things like, you know, if you're saving enough to hit your goals on time, if you've
00:19:20
invested in a manner appropriate for the timelines to your goals. We look at your
00:19:24
tax situation from now until, you know, the end of time, the end of your life, and determine if you're set up in a way
00:19:29
to minimize your lifetime tax bill as best we can or if we need to make some changes there. We make sure you're
00:19:34
properly insured against the various risks in your life. We make sure that your estate plan matches up with what
00:19:39
your wishes actually are. And with all those kind of numbers on the table, the current snapshot and at least a little
00:19:44
understanding of how that snapshot might change over time, the next step really is to fill in the gaps. And you know,
00:19:50
what are some of those gaps? Well, how do you get from your current state to the point where you achieve your goals?
00:19:56
How much do you need to save? How should you appropriately invest those savings?
00:20:00
And why? What are the major risks that you're currently exposed to that either
00:20:03
you're not aware of at all or that you are aware of but simply haven't addressed sufficiently? Where are the
00:20:09
leaks? Right? Frivolous spending, insufficient tax planning, poor kind of subpar investment choices. In short, we
00:20:16
want to identify a whole slew of edits and changes and recommendations to what you're currently doing. And then you
00:20:24
need to implement those changes. Some of those changes can be implemented immediately. Some take time. Some might
00:20:30
take an introduction to another professional to help you out. Some might take, you know, months if not years of
00:20:35
conversations internally, right, with your spouse, with your family, things like that. Everyone's list on in in
00:20:41
terms of the changes and how to implement those changes. Everyone's list is going to look unique to them. It's
00:20:46
actually kind of fun, pretty cool. And you might go through the process, and this is just like an example of some
00:20:51
things that honestly it's probably from like the last month of work alone that
00:20:55
you could go through the process and see that, oh, you need to start saving an additional $500 a month, which really
00:21:01
means you need to start spending $500 a month less, and you need to determine where that $500 a month is going to come
00:21:06
from. You just realize that, man, your your spouse could open and start contributing to a Roth IRA right away,
00:21:12
and there's no reason for him not to have one. You need to start putting $200
00:21:16
a month into a syncing fund like a high yield savings account to pay for your annual camping trip. You need more term
00:21:21
life coverage. You know, at least a million dollar policy over the next 15 years. And you should probably speak to
00:21:26
a independent life insurance broker or go, you know, shop around yourself for that coverage. Uh you find out that your
00:21:32
estate documents are outdated because now you have multiple children and multiple grandchildren and you need to
00:21:38
review those with an attorney. you find out your investment allocation is way too conservative and you need to make
00:21:43
immediate changes to all your qualified accounts, but you probably won't take
00:21:47
any action in your taxable account until the fourth quarter of this year. And then you're going to look at your tax
00:21:52
projection at that time and you'll kind of rebalance accordingly. Then you need
00:21:57
to ask your spouse's parents about their inheritance planning. They've been vague
00:22:00
before and clarity there would be really helpful to you because it's kind of a
00:22:04
touchy subject. Like those are all the kind of uh action items or implementation items that can fall out
00:22:10
of the financial planning process and you put a plan together to implement those changes. Changes to your
00:22:16
portfolio, changes to your documents, changes to your spending habits, to your saving habits, on and on and on. That's
00:22:22
what deep dive financial planning looks like. It is more than build a portfolio.
00:22:26
It is more than start buying index funds. But back to Bob's question about his mid20s children. I narrowed it down
00:22:33
to four big things that I would recommend young adults earlier in their career focus on. Like eventually you can
00:22:40
get to estate planning early on. I would one get in the habit of measuring your spending. Know how much money leaves
00:22:48
your life every month. It does not mean that you have to budget. It just means that you're aware of how much money is
00:22:53
coming in which everyone is usually aware of because they know what their salary is. But you have to become aware
00:22:58
of how much money is going out of your life on a monthly basis. That's the first one. The second one I would say is
00:23:04
think about those goals. Again, the exercise can take the form of some deep intertwined philosophical process. Why
00:23:11
am I here? What is this all about? Is it about scuba? >> If I can't scuba, then what's this all
00:23:16
been about? What am I working toward? >> But it can also be really simple. It can
00:23:20
sound something like, I'm 25 years old and I'd love to spend a few hundred a
00:23:24
month on fun things, but also I would like to save twice as much as I spend on fun things for the long run. I'm not
00:23:31
even sure why I need to save that much yet, but I just want to start saving because it feels like a good thing to
00:23:36
do. I think that's fine. I think that's a fine goal, a fine thing for a 25-year-old person to say. So, the
00:23:42
second thing was to think about some of those goals. The third thing is yes, start investing now. Even in small
00:23:47
amounts, even if only in a couple accounts, likely an employer retirement account like a 401k and perhaps a second
00:23:54
one like a Roth IRA or a taxable account. And even if it is just one simple index fund, the the reason why
00:24:00
we're investing here isn't because it's in alignment with some kind of grand
00:24:04
master financial plan. It's simply to get some skin in the game and start learning about the process of investing.
00:24:10
I think that's important. And I also think it's important just to start,
00:24:13
right? get some sort of compounding working early. You can figure out some of the finer details later on. That is
00:24:19
totally okay. And the fourth one, we'll have a little pop quiz here. The pop
00:24:23
quiz is what asset do all young people have huge amounts of? And if you're thinking time, you're on the right
00:24:30
track. I would call it human capital. The economic value of a worker's skills
00:24:34
and knowledge and experience and health and and other personal attributes that contribute to some sort of productivity.
00:24:40
Well, time is a really big part of that. And young people have lots of time ahead
00:24:44
of them. So I would consider learning more or focusing on increasing your income over time. It's not a requirement
00:24:51
and it's not easy, right? In fact, it's pretty rare that it's easy. For example,
00:24:56
my parents were both public school teachers. Their teaching salary was set by the state. They had very few dials to
00:25:02
turn to increase their income. You know, they could coach at school. They could run the chess club, something like that
00:25:06
for a little extra income. But looking at them as an example, kind of continuing the example, my dad started a
00:25:12
a small software company in the late 90s and early 2000s, basically in his spare
00:25:17
time. Not that he had that much of it, but the software was test review software for the New York states, they
00:25:23
they call them the regent exams, kind of the state school science exams, biology,
00:25:27
chemistry, physics, earth science. So, he kept on teaching full-time, but he found this small little way on the side
00:25:32
to earn some extra income. So whatever your career and your interests allow, I think as a young person, you can
00:25:39
consider how you could improve or increase the remaining human capital in their career, it's not necessary. And I
00:25:46
I don't think everything has to be about earning more money, making more money,
00:25:49
money, money, money, money, money. That's not it. But if someone in their mid20s is interested in improving or
00:25:55
optimizing their finances in some way or they just want to see what options are out there for them, if you think about
00:26:00
the compounding effect of a 10 or 20 or 50% raise or a 100% raise or higher and you think about that compounding for the
00:26:08
next 30 or 40 years, it's pretty impressive. So Bob, great question. Thanks for writing in and thanks to John
00:26:14
from Pittsburgh for asking about the financial planning system or process. Here's a quick ad and then we'll get
00:26:20
back to the show. Serious question. Why do podcasters constantly ask for ratings
00:26:26
and reviews? Yes, they do help highlight our shows to new listeners. They help strangers find us on Apple Podcast and
00:26:32
Spotify. It's totally true and a good reason to ask for ratings and reviews.
00:26:36
But I have something more important, at least more important to me. I want to know if you like this stuff. I want to
00:26:43
know if you like my podcast episodes, my monologues, my guests, the information I
00:26:47
share with you and the stories I tell. I want to improve and make your listening
00:26:51
more enjoyable in the process. So yeah, I would love to read your reviews. And sure, if you throw a rating in there,
00:26:57
too, that's great. If you like what I'm doing, please share it with me. It's
00:27:01
such a great feeling to read your feedback. I'd love to read your review or see a rating on Apple Podcast or
00:27:07
Spotify. Thank you. And the last question today is from Bernard from Ireland. Always love it when we get
00:27:13
international questions. My brother lives in Ireland. Actually, Bernard, he's in Cork. So, if you ever find
00:27:18
yourself in Cork and you see a chatty guy in a bar who looks and sounds like me, it might be my brother. But Bernard
00:27:23
is a uh financial planner from Ireland. And he said, "Jesse, one challenge I
00:27:27
face is helping clients to take the time to plan for retirement. The busier, the
00:27:32
wealthier, the harder it is to get them to sit down and put proper plans in place. any guidance on the subject would
00:27:38
be appreciated. So, thanks for the question, Bernard. I love again it goes back to the engineer in me. I love when
00:27:44
I can create a concrete objective answer to a question and this one I think is the opposite. What follows are some of
00:27:50
my subjective observations when I dig into the way that people tend to work in psychology and behavioral finance and
00:27:56
some of that. Some of those answers seem to um not maybe be repetitive or they seem to rhyme over time. And so what I'm
00:28:04
about to describe is just some of that that I've picked up over time. And I think whether you're a financial
00:28:08
planner, which I think somewhere maybe 15 20% of my audience are are financial professionals, or you perhaps find
00:28:14
yourself in a position where you're providing financial guidance to a friend
00:28:17
or a family member in your life, which I do know that the other 80% of you listening, many of you, you know, smart,
00:28:23
capable DIYers who listen, I know that you guys do often play that role for other people in your life. I hope that
00:28:29
my subjective experiences that I'll share with you now and the thoughts from
00:28:33
other really smart advisers out there like a a Michael Kitsis or a Carl Richards or many other industry voices
00:28:39
can help you out. So my first thought is that well yeah people are busy. It's
00:28:43
true for many people time is one of if not their their number one scarce resource. So asking them to sit down and
00:28:51
plan might be like asking them to create time that doesn't really exist. I found
00:28:55
it does help to acknowledge that reality pretty explicitly. Not really a to give
00:29:00
them an excuse, but as context. Planning has to feel efficient. It has to feel focused. It has to feel worth the
00:29:06
interruption or else it simply won't happen. There's this great YouTube video
00:29:10
of a Goldman Sachs banker or attorney. I I know he was he has a law degree and he's speaking at a law school. So that's
00:29:17
why I think he might be an attorney as well as a Goldman Sachs investment banker. One thing he talks about is uh
00:29:23
as an adviser is your meetings ought to have an agenda. They ought to be with a you know a set agenda with a bunch of
00:29:29
tasks that clearly you're going to get done. It's not just you know hey come in
00:29:33
for an hour and let's just shoot the breeze. It's you're you're there to be
00:29:36
efficient. You're there to be focused. You're there to get stuff done to to use
00:29:40
everyone's time wisely. I think about myself and you know over the past month
00:29:44
I felt like I haven't had any time to exercise. I've had to have this deliberate, intentional effort just to
00:29:50
move my butt a few times a week. People often feel like they don't have time to
00:29:54
maintain relationships or friendships. They don't have enough time to get adequate sleep. They don't have enough
00:29:58
time to sit down and write the great American novel or whatever that big project is they have on their mind. So,
00:30:04
I think the point is it's really common and and really human to simply not have
00:30:08
enough time or, you know, in quotes, not have enough time. So, one big takeaway from my time working as a financial
00:30:14
planner is that 99% of the time they genuinely don't have the time and it's
00:30:18
it's nothing that you have done, Bernard, right? And also 99% of the time, they appreciate you gently nudging
00:30:24
or badgering them into action. And for what it's worth, if it's helpful, I have
00:30:28
this little rule, it's probably the math nerd in me, this little rule for when
00:30:31
I'm badgering people to get responses back to me, especially if I don't know
00:30:35
them very well yet and I'm not sure how they tend to operate. So, here's an
00:30:38
example of of my rule in practice. I have a good conversation with someone. Usually within 24 hours the next day,
00:30:44
I'm sending them an email to to follow up with them with some action items. Okay. And then they don't respond to me.
00:30:49
So, usually I wait about a week. I send a follow-up, a reminder email. Let's say
00:30:53
they don't respond to that one. And now the rule is kind of kicking in. So, I
00:30:56
waited 1 week after the first bit of radio silence. I give them two weeks. Now, let's say they still have no radio
00:31:02
silence. No. I send them an email, no call, nothing. I double the waiting time again to four weeks. I double the
00:31:08
waiting time again to 8 weeks. So now it's been a full three or four months since they've actually gotten back to
00:31:15
me. I'm not badgering them every day. I'm not even badgering every week. Every
00:31:19
time they don't get back to me, I expand the time until I badger them again. And
00:31:24
then at that point, if they still aren't getting back to me, the person enters a
00:31:27
a once per quarter contact pattern. Personally, I think if if someone's reaching out to you once every 3 months
00:31:33
and and especially if you hired them to help you, that's not bad. It's not like
00:31:37
you're really bothering the person. But I will say if that person's a client, if
00:31:41
they've been really gung-ho about working with me, and then they go silent for a whole quarter, they don't answer
00:31:47
three or four or five calls or emails, usually I'm going to go out and make some sort of special effort to have a
00:31:53
kind of a hey, what's going on? What's happening kind of conversation. Mainly
00:31:57
cuz I don't want their expectations to be disappointed by the fact that we're
00:32:01
not really making any progress and not really communicating at all. If they're
00:32:05
okay with that and if that's how they want to operate, well, at least now I know that. But still, I think the bigger
00:32:10
point here is that people are busy. Second, you can lead a horse to water, but you can't make them drink. No matter
00:32:16
how competent or caring we are, we can't want retirement planning more than the
00:32:21
other person wants retirement planning, the client or the person we're helping.
00:32:24
Our role isn't to to drag people across the finish line, right? We have to make
00:32:28
the path visible. We have to make it accessible. Hopefully, we have to make it compelling. And that's always a hard
00:32:32
part is to try to make it compelling. And I've really, yeah, I've struggled
00:32:36
with it at times, but slowly I'm learning that I think sometimes success is just planting a seed that grows later
00:32:42
on. It's certainly not always forcing a decision today. One takeaway for me and
00:32:46
and one little lesson I've learned over time is that I think I can now start to
00:32:50
notice the pattern when a client is really interested in getting stuff done. When they really feel that thirst,
00:32:55
continuing maybe the horse metaphor, that thirst to get something done. And sure enough, they get right on it.
00:33:00
They're right on all the action items and getting back to me and and the process of going back and forth and
00:33:05
getting them answers is really efficient. And that feels great, right? To get a lot of work done and answer
00:33:10
someone's burning questions and to get it done promptly. But over time, I've
00:33:14
noticed that some people just don't have that kind of short-term burning desire
00:33:17
for answers. And I just genuinely think it's hard to to make them drink. And so
00:33:22
we just need to level set our expectations and realize it's not always going to work out as quickly or with as
00:33:28
much efficiency or desire as maybe you want it to. The third thing I think is yeah retirement and money are definitely
00:33:34
these emotionally loaded topics. And that's important for a lot of people. Retirement planning triggers fear,
00:33:40
uncertainty, guilt, fear of not having enough, uncertainty about the future, guilt about who knows any number of
00:33:47
things, right? past inaction, guilt about even being able to retire. Especially, you know, maybe some people
00:33:52
are out there retiring at 48 or 52 or 57 and their peers, their siblings, their parents, they didn't get to retire until
00:34:01
70. And people feel guilty about that at times. The point is that people can often avoid intimidating conversations,
00:34:08
uncomfortable, emotional conversations even when they know they're important,
00:34:12
right? Avoidance isn't laziness, right? It's just um it's very human self-p
00:34:16
protection. It's simple basic human psychology. It's the same reason why
00:34:21
some people use drugs and alcohol as a as a numbing avoidance. Some people use distraction like video games. Uh some
00:34:27
people are workaholics. Some people dissociate obsessively worry. Humans have lots of different ways and some of
00:34:34
them are totally subconscious ways to avoid these hard intimidating topics. and financial planning, retirement
00:34:40
planning, and money are for many people one of those hard topics. The fourth thing, Bernard, I think is that some
00:34:47
clients just truly genuinely don't get it. They don't get it. They don't
00:34:51
intuitively understand the the power, the leverage, the benefit of good planning. They don't understand the cost
00:34:57
of delaying. They don't understand the peace of mind that they could get from
00:35:02
clarity if only they had clarity. So, basically, there's an education gap here. It's not a character flaw. And and
00:35:08
so part of our job is to translate these often abstract future benefits that we talk about into concrete present-day
00:35:16
value that they can actually feel. It is cheesy and and it feels cheesy to say something like, "Well, what if I could
00:35:22
save you $10,000 on your taxes this year?" Feels cheesy to say. Or, "You
00:35:27
know, this decision is probably going to lead you to $100,000 between now and retirement. Would that interest you?"
00:35:33
What I'm telling you would allow you to retire four years earlier than you might
00:35:37
think. Is that something you care about? To me, those statements, they sound clickbay, right? They sound a little bit
00:35:43
like a used car salesman. Like, really? Are you're going to put you're going to
00:35:46
keep your family in that car instead of buying this this new safer model that I'm about to sell you? Like, it that
00:35:52
feels very salesy to me. But one of my guiding principles is to let the numbers be my guide. And if the numbers say
00:36:00
wonderful things, well then I'm not afraid to say that wonderful thing. And if someone genuinely doesn't get it,
00:36:05
I'll do my best to close that education gap. I'll ask them, well, what about
00:36:09
this $100,000 decision doesn't appeal to them? And it can be hard sometimes to
00:36:13
not come across in that used car kind of way. But again, the math is the math. And that's something I'll explain to
00:36:19
people, too, is I'll say, "Listen, this is this is math. And I'm not using this
00:36:23
in in a used car way cuz in this case, you know, quote unquote getting it, understanding it, that's absolutely in
00:36:30
in the client's best interest or in your friend's best interest or in your
00:36:33
family's best interest. So doing what you can to bridge that gap to getting it
00:36:37
is extremely helpful for everyone involved. The the next thing I think, Bernard, the fifth thing is that any
00:36:43
sort of urgency in these situations is going to be invisible when life is going well. When the going is good, a lot of
00:36:48
important topics can seem pretty abstract and pretty distant. nothing feels if if nothing feels broken I
00:36:54
should say then there's really going to be no sort of forcing function to get
00:36:57
people to act the way around this or at least one way around this is to remind people that financial planning isn't
00:37:02
about fixing an obviously broken problem in other words so you shouldn't be waiting for some sort of obviously
00:37:08
broken problem to start financial planning instead financial planning is about protecting optionality building in
00:37:15
flexibility uh building in future freedom for yourself and and that can be a little bit of a reframing of the
00:37:21
conversation And I think this one's pretty human, too. You know, the squeaky wheel does
00:37:25
get the grease. And if it ain't broke, don't fix it. These are these common
00:37:28
idioms and in ways that we live our life. And if the person you're talking to doesn't hear a squeak and they don't
00:37:33
see anything as broken, they probably won't fix it. So again, it can be challenging because you don't want to
00:37:39
twist anyone's arm. You don't want to lead with fear. It's broken and you're
00:37:42
screwed and I'm the only one who can help you out. You don't want to do that.
00:37:45
I think it's okay to gently say, "I know what I'm doing here. Uh, I see a few
00:37:49
things going on. A lot of things are going really, really well. I also see a few things that I think you ought to
00:37:54
improve on, and here's what they are. And the last one that came to mind, Bernard, the last of my little notes
00:37:58
that I took down is that progress isn't always perfection. It's not always what
00:38:02
you want it to be, but it is still progress. And so, I try, and it's not always easy, but I tried to not view
00:38:07
kind of this ongoing client engagement as some sort of all or nothing event. I think a short conversation is better
00:38:13
than no conversation. I think a a first draft plan is better than no plan. And I
00:38:18
think even a small a small win, clarity on some goals, getting someone to start saving a little bit more, getting
00:38:24
someone to understand some trade-offs going on in their life, that will build momentum over time. And I have a few
00:38:30
clients who I work with who they tend to be 3, four, 6 months of radio silence and then a twoe flurry of communication
00:38:38
where I spend 10 hours dedicated only to them over over a oneweek period of time
00:38:43
and then uh and then six more months of radio silence. and it it seems to just be that way over and over and over
00:38:48
again. I've learned over time that's just their MO. And and I'm glad we make
00:38:52
progress during those really brief flurries. And when asked, I usually tell people that the first 6 months we work
00:38:57
together will tend to have a higher concentration of communication as we get this baseline plan put together. And
00:39:03
then as time goes on, maybe we only have two big sitdowns a year. But some folks
00:39:08
I work with due to their preferred communication schedule which is a little more spread out. We're still kind of
00:39:14
talking through those initial details and we're two years into our working relationship but still there's progress
00:39:20
and that again is the important thing. Those situations to me they aren't perfect but they are progressing. And at
00:39:25
the end of the day, I want to measure success less by how many clients kind of fully engage immediately, and more by
00:39:32
whether I'm consistently creating clarity, lowering friction, keeping the door open for future action and and
00:39:38
helping people the way that they want to be helped. I still want to be able to put my head on the pillow at night and
00:39:43
feel good about what I do and feel like I'm really helping people. But again,
00:39:47
you can lead a horse to water. You can't make them drink. And if there's slow but
00:39:50
steady progress, that's better than no progress at all. So, thank you for the
00:39:54
question, Bernard. It was a really cool question and I think we have a great group of people listening here who
00:39:58
choose to spread you know smart financial ideas into their small corners of the world and I hope today's
00:40:03
conversation helped you all out and that's all I have today everybody. So thank you as always for submitting your
00:40:08
questions. Please keep them coming to jesse at bestinterest.blog. While you're
00:40:12
emailing me make sure to sign up for uh the free weekly newsletter over at the homepage at bestinterest.blog. We'll
00:40:17
talk to you next time on personal finance for long-term investors. And have fun scubaing. Did one of you tell
00:40:23
Stanley that I have asthma? Cuz I don't. If it gets out, they won't let me scuba.
00:40:28
If I can't scuba, then what's this all been about? What am I working toward?
00:40:33
>> Thanks for tuning in to this episode of Personal Finance for Long-Term Investors. If you have a question for
00:40:39
Jesse to answer on a future episode, send him an [music] email over at his blog, The Best Interest. His email
00:40:45
address is [email protected]. Again, that's jessevestinterest.blog.
00:40:51
blog. Did you enjoy the show? Subscribe, rate, and review the podcast wherever you listen. This helps others find the
00:40:58
show and invest in knowledge [music] themselves, and we really appreciate it. We'll catch you on the next episode of
00:41:04
Personal Finance for Long-Term Investors. Personal Finance for Long-Term Investors is a personal
00:41:09
podcast meant for education and entertainment. It should not be taken as financial advice and it's not
00:41:15
prescriptive of your financial situation.

Episode Highlights

  • Welcome to Personal Finance for Long-Term Investors
    Join Jesse Kramer as he simplifies personal finance and investing for busy professionals.
    “An investment in knowledge pays the best interest.”
    @ 00m 04s
    February 04, 2026
  • Understanding Financial Planning
    Dive into the differences between a portfolio and a financial plan with Jesse.
    “A financial plan aligns your money with your life.”
    @ 07m 00s
    February 04, 2026
  • The Importance of Goals in Financial Planning
    Explore the significance of defining personal financial goals beyond just retirement.
    “What’s the point? Why are you working hard?”
    @ 11m 49s
    February 04, 2026
  • The Importance of Asking Why
    Interrogating your thoughts can lead to deeper understanding and clarity in your goals.
    “Ask them to interrogate your thoughts. Why? Why? Why?”
    @ 16m 15s
    February 04, 2026
  • Understanding Your Financial Snapshot
    A comprehensive review of your assets, debts, income, and spending is crucial for planning.
    “Your life is dynamic and the numbers in your financial plan will certainly be dynamic, too.”
    @ 19m 00s
    February 04, 2026
  • Identifying Financial Gaps
    Recognizing the gaps in your financial planning can lead to actionable changes.
    “You need to start saving an additional $500 a month, which really means you need to start spending $500 a month less.”
    @ 20m 55s
    February 04, 2026
  • Emotional Barriers in Retirement Planning
    Retirement planning triggers fear and guilt, making clients avoid important conversations.
    “Avoidance isn’t laziness; it’s human self-protection.”
    @ 34m 10s
    February 04, 2026
  • Bridging the Education Gap
    Many clients don’t grasp the importance of financial planning, creating an education gap.
    “It’s not a character flaw; it’s an education gap.”
    @ 35m 04s
    February 04, 2026
  • The Challenge of Client Engagement
    Clients often go silent, making it hard to gauge their interest. Understanding their communication patterns is key.
    “I’ve learned over time that’s just their MO.”
    @ 38m 50s
    February 04, 2026

Episode Quotes

  • Investing is cool, right?
    The Financial Planning Process, Step-By-Step | AMA #13 - E129
  • What’s the point? Why are you working hard?
    The Financial Planning Process, Step-By-Step | AMA #13 - E129
  • If I can’t scuba, then what’s this all been about?
    The Financial Planning Process, Step-By-Step | AMA #13 - E129
  • Ask them to interrogate your thoughts. Why? Why? Why?
    The Financial Planning Process, Step-By-Step | AMA #13 - E129
  • You can lead a horse to water, but you can't make them drink.
    The Financial Planning Process, Step-By-Step | AMA #13 - E129
  • Progress isn't always perfection, but it is still progress.
    The Financial Planning Process, Step-By-Step | AMA #13 - E129

Key Moments

  • Listener Review01:02
  • AMA Episode01:37
  • Financial Planning Basics01:37
  • Financial Snapshot19:00
  • Identifying Gaps20:55
  • Client Silence31:45
  • Invisible Urgency36:43
  • Progress Over Perfection38:00

Tension Over Time

Words per Minute Over Time

Vibes Breakdown