If You Want Financial Freedom You Can’t Ignore This (Parts 1 and 2)

We avoided estate planning for a long time; here’s why you shouldn’t. Without an estate plan, you’re giving over the control of what happens to all your assets to others. In part one of this two-part series, Eric + Jason talk about what they did to – finally – get their respective plans in place. Topics discussed in this episode include the elements of estate planning, why people delay + how to get started, living trusts, and taking care of your heirs. Don’t be like those who put this off “until they’re older”: join us now for the first episode of this two-part series.

Note: This content does not constitute investment advice and is being presented for informational and educational purposes only.

Part 1

Part 2


Show Notes

Essential Background: If you’re not familiar with our family situations, check out our earlier videos where we’re joined by our spouses (part 1 and part 2), and the recent episodes about our kids (part 1 and part 2). Note that each is a two-part series, and separate links are provided for all videos.

Estate planning FAQs: After viewing these videos, you’ll be better equipped to ask deeper questions about your own estate planning needs. We found this resource from the American College of Trust and Estate Counsel (ACTEC) to be really helpful. All of the high level topics discussed in our series are covered here.

What is a trust? This Investopedia article is a good starting point for clarification on the different types of trusts and other pertinent details. This is a subject where it’s easy to fall down a very deep rabbit hole, and having a good foundation first is always helpful. Be sure to research the particulars of your state or country as well, as things differ substantially.

Advanced care planning is an essential element of estate planning, and one we touched on in part 1 and expand upon in part 2 of this series. Thinking through your own preferences can be difficulty, but planning for them is vitally important.

Umbrella Insurance is among the most important (and least expensive) tools available to protect your assets. These policies sit on top of your existing liability coverage (auto, home, etc) and extend it. To learn more about umbrella policies, check out this Investopedia post.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

Breaking Up With My Financial Advisor?

Did you know that financial advisor fees can eat up HALF of your portfolio’s value over time? While happy with the good support and great relationship he had with them, Jason was thinking about leaving his financial planners late last year. In this episode, we capture a conversation Eric + Jason had on this topic, as they discussed the merits and downsides of paying assets under management (AUM) fees. Topics covered in this episode include why he stuck with them over the years, the value advisors can bring, more cost-effective options for financial advice, and how Jason is making his decision. Get the facts and make the right choice for yourself!

Note: This content does not constitute investment advice and is being presented for informational and educational purposes only.


Show Notes

Essential Background:

  • Have you seen our two-part series (part 1 and part 2) on asset allocation? These episodes provide context from Jason on his portfolio and work to date with advisors.
  • The Bogleheads wiki contains some great content about investment advisors and financial planners, helping to clarify the differences between them. In these two articles you can learn some important definitions and information that provide key background to this topic.

10 Questions to Ask Your Financial Advisor was put out by the Certified Financial Planner Board of Standards, Inc. (CFP Board), which is a “non-profit organization that serves the public by fostering professional standards in personal financial planning”. This document is a must-read for anyone even considering financial planning services, and helps to arm you with the information you need to have any conversations.

Interested in researching financial advisors? This link will take you to one of the better resources we’ve seen for investigating potential options. As described on the site, XY Planning Network’s member advisors ascribe to fiduciary and CFP standards, earn no commissions, and require no minimum assets. They have convenient filters to allow searching by advisor specialities, including those with FIRE experience. Many work under multiple fee models, including advice-only, which can be a good source for one-time consults without any ongoing feels. [Two Sides of FI has no relationship with XY Planning nor do we receive any compensation from them.]

BrokerCheck is a resource by FINRA (Financial Industry Regulatory Authority), which allows you to research individual financial planners and brokers, as well as firms. This is a key site for looking into the details of a potential financial advisor or perhaps one with whom you are already working.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

Our FIRE Portfolios Are Down 20%, What Now?

How has the recent market downturn changed our plans? Jason + Eric candidly discuss their pre- and post-FI moods in this volatile time. Learn what they’re doing and thinking about right now as Jason nears the two-year post-FI mark and Eric contemplates pushing his 2024 FI date back.

Note: This content does not constitute investment advice and is being presented for informational and educational purposes only.


Show Notes

Essential Background: Let’s start out with some definitions. Terms like correction, market crash, and bear market are thrown around casually at times and knowing their meaning is important. This Fortune article is a brief and effective summary.

Buying Stock in a Down Market is a part of show guest, Fritz Gilbert’s, post-FIRE strategy, which he discussed in a recent conversation with us. In this episode highlight, we discuss how he felt during the 2020 market decline and learn about his approach to continue buying in order to take advantage of low equity prices.

The Psychology of Money (Morgan Housel), is the book Eric discussed in this episode. Subtitled “Timeless lessons on wealth, greed, and happiness”, it recounts 19 short stories “exploring the strange ways people think about money and teaches you how to make better sense of one of life’s most important topics”.

Fixed Income has an essential role to play in any portfolio, particularly as you approach your retirement date. Did you miss our two-part series on Eric’s recent efforts to change their asset allocation from 100% stock? As he referenced in the current episode, that was an important part of increasing his confidence in this down market. Be sure to check out part one and part 2 of our conversation, as well as the behind the scenes conversation Eric and his wife Laura shared on this essential topic.

Tax Loss Harvesting is a concept we’ve discussed on the show before, but haven’t dug into deeply. This Investopedia article is a good summary. In brief, TLH is an approach by which investors can sell an asset at a loss, reducing the total amount of capital gains taxes due from the sale of profitable investments. You can then use the sale proceeds to purchase a similar asset or security, maintaining your asset allocation.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

Teaching Our Teens About FI and Money (Parts 1 and 2)

Having children comes along with many necessary expenses, but also provides a key opportunity to provide them with a solid financial education. In part one of a two part series, we tackle a topic that’s been requested many times by viewers: all things relating to kids. Topics discussed in this episode include our own financial upbringing, early attempts to teach our kids about saving + investing, the value of teens having jobs, and talking with them about FIRE. Join us for the first episode of this two-part series.

Note: This content does not constitute investment advice and is being presented for informational and educational purposes only.

Part 1


Part 2

Show Notes

Essential Background: If you haven’t watched our very first episode of Two Sides of FI which contains much of our own financial backstory, this is definitely material relevant to our discussion here.

UTMA custodial accounts may be useful investment vehicles for you to consider for your children, particularly when they don’t yet have earned income and are not eligible for a Roth IRA. These accounts are very flexible by design, and unlike with a 529 plan, the funds in a custodial account do not have to be used solely for higher-education expenses. 

529 Plans are tax-advantaged savings plans designed to encourage saving for future education costs. There are many different places that can host these accounts including but not limited to the same brokerages you may use for your own investments. Be sure to look into whether there are (tax or other) advantages in your state of residence before deciding where to invest.

Roth IRAs are well known by most viewers of our channel, but did you know there are compelling reasons to consider them for your kids? For minors, these will need to be custodial accounts just like a UTMA and most brokerages offer them.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

Buying Bonds. Still Not Convinced I’m Doing the Right Thing! (Part 2)

I reallocated my investment portfolio, sold out of my 100% equity position and I’m not happy about it. Part two of a two-part series, you’ll learn why and how I’m making peace with it. Ensuring that your investment portfolio can fund your lifestyle for the duration of your lifespan is essential to success in FIRE. One of the most impactful elements of that is how your portfolio is constructed, or your asset allocation. In this episode, Eric discusses his desire to reduce the risk of his portfolio with Jason, and ensure he + Laura are set up for success. Topics discussed include the role of bonds + fixed income, the types of investment risk, seeking feedback from internet forums, and tax considerations. Join us for the second episode of this two-part series on Eric’s reallocation experience.

If you missed Part 1, which includes a link to a behind the scenes conversation with Eric + Laura, be sure to check it out first!

Note: This content does not constitute investment advice and is being presented for informational and educational purposes only.


Show Notes

Essential Background: If you haven’t watched our previous episodes on asset allocation (part 1 and part 2), this is highly relevant material to our discussion here.

Series I Savings Bonds (I Bonds): These assets are rightfully getting a lot of interest in the moment given their unusually high returns (for now). Get all the details via Treasury Direct. For more details, check out this recent Money Guy Show episode as well.

Investment Policy Statements (IPS) are key guiding documents for your investment portfolio. Don’t have one? Have a look at this Bogleheads wiki article for all the details that you’ll need to help put one in place.

How To Build A Retirement Paycheck:  This is the first of three great Retirement Manifesto posts on author Fritz Gilbert’s implementation of the Bucket Strategy, which we have touched on in several episodes to date. Here you’ll find guidance on how to determine the asset allocation you’ll want to have in place by the time you retire early. The other two articles in the series are linked here as well.

A Bond Tent strategy is one of the common approaches used by the FIRE community to mitigate both Retirement Date + Sequence of Returns Risks (RD and SRR in the images below). As is often the case, Michael Kitces has a great article on the topic. We couldn’t cover sufficient depth on this important topic in our episode, but this post has all the details you need. See the graphics below:


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

I Rebalanced My FI/RE Portfolio and I Hate It! (Part 1)

Eric reallocated his investment portfolio, sold out of his 100% equity position and he’s not happy about it. In this two-part episode, you’ll learn why and how he’s making peace with it. Ensuring that your investment portfolio can fund your lifestyle for the duration of your lifespan is essential to success in FIRE. One of the most impactful elements of that is how your portfolio is constructed, or your asset allocation. In part one, Eric discusses his desire to reduce the risk of his portfolio with Jason, and ensure he + Laura are set up for success. Topics discussed include the role of bonds + fixed income, the types of investment risk, seeking feedback from internet forums, and tax considerations.

Note: This content does not constitute investment advice and is being presented for informational and educational purposes only.

Pick up where part 1 leaves off with a bonus, behind-the-scenes look at Eric and Laura’s decision-making process (video below).


Eric + Laura Discuss Their Reallocation

Show Notes

Essential Background: If you haven’t watched our previous episodes on asset allocation (part 1 and part 2), this is highly relevant material to our discussion here.

Vanguard’s Principles of Investing Success is a really great read. It’s chock-full of information, including the chart showing average returns by asset mix (pp. 10) that Eric referenced in this episode. Whether you’re just getting started with investing or are very experienced, we suspect you’ll find something of value in this easy read.

How To Build A Retirement Paycheck:  This is the first of three great Retirement Manifesto posts on author Fritz Gilbert’s implementation of the Bucket Strategy, which we have touched on several episodes to date. Here you’ll find guidance on how to determine the asset allocation you’ll want to have in place by the time you retire early. The other two articles in the series are linked here as well.

Financial Independence: How Long Will It Take? We showed visuals from this Go Curry Cracker post, which highlights the dramatic impact that your overall savings rate has on determining your FI timeline. This concept is also covered in the “Principles of Investing Success” article linked above.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

Retirement Is Nothing Like I Thought It Would Be

We all daydream about what retirement will be like, but will reality live up to expectations? In this episode, Eric and Jason are joined by Fritz Gilbert, who blogs at The Retirement Manifesto. Now nearly four years after retiring early, Fritz brings valuable experience + perspectives to this question. Our discussion goes well beyond the numbers, covering topics including finding your purpose, working “one more year”, determining your FIRE timing, and the keys to success in retirement.

Note: This content does not constitute investment advice and is being presented for informational and educational purposes only.


Show Notes

Retirement Is Nothing Like I Thought It Would Be – This is Fritz’ post that inspired us to make an episode of Two Sides of FI together. As you may have gathered from our earlier episodes, Jason completely agrees with Fritz that it’s impossible to really know what retirement is going to be like until you experience it. Now in his fourth year of early retirement, Fritz has a lot of experience to reflect upon and we’re grateful that he’s chosen to share it with us.

Keys to a Successful Retirement – As we discussed in this episode, Fritz recently wrote a book capturing lessons he learned on his retirement journey so far. His own description of the book is a really apt summary: “Covering topics like finances, embracing your passions, and dealing with feelings of aimlessness, grief, and depression that may crop up, this in-depth guide to retired living answers all the burning questions you want to ask—as well as those you’re afraid to. Take a complete look at your newfound freedom and explore what it really means to have a successful retirement.” We highly recommend it!

In this episode, we referenced a number of different blog posts Fritz wrote that we found useful, inspiring, and impactful. Please be sure to check them out:

Freedom for Fido is the charity that the Gilberts started, whose stated purpose is to:
“Free the dogs who live on chains in the North Georgia Mountains. We are a charity which provides free fencing and dog houses for low-income residents of the Blue Ridge area.” This project is clearly an important part of their lives and we’d recommend you check out the great and impactful work they’re doing together with their volunteer community.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

Financial Independence, Retire Early…Go Back to Work?

Discussing the concerns, worries, and interests occupying our thoughts right now. A temporal look from their respective sides of FI, Eric and Jason discuss a new job prospect, while Eric is a little too focused on saving to achieve FI. They probe ideas about how “vacation time” is different post-RE, as well as their current favorite podcasts and books. 

Note: This content does not constitute investment advice and is being presented for informational and educational purposes only.


Show Notes

Eric’s “NOW” page @ 30X40 Design Workshop is where you’ll find links to some of the things that are inspiring Eric right now in his studio: tools, books, YouTube channels, podcasts and more. This includes links to the content he referenced in this episode.

Jason’s reading list – Here’s a list of all the books he’s read recently, is currently reading, or are up next. This is an example of a simple Notion page where you’ll find links out to learn more about these titles. Simply click on the triangles to the left of each section header to expand the respective lists.

Tenet was one of Jason’s favorite movies of 2021 and the link will take you to the film’s website. This movie can be a little challenging to wrap your brain around at times, so be forewarned. But once you get comfortable with “how the world works” in Tenet, it’s a really wild ride. It’s also visually stunning, so watch it on the largest screen you can. At the above linked you’ll find paths to digital copies and other purchase options. Depending on your region, you may also find it streaming on HBO or HBOMax, and potentially other services.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

Comparing our FIRE Portfolios + Asset Allocations (Part 2)

Choosing how to divide your assets among stocks, bonds, and other investment vehicles is a good first step, but asset allocation also impacts your tax rate, portfolio performance, and long-term ease of maintaining it all. In part two, Eric and Jason dig further into their own portfolios from their respective sides of FI and discuss the role of bonds, risk, tools you can use to assess your portfolio and model performance, rebalancing, and an interesting – not often discussed – case for financial advisors.

Did you miss Part 1? Check it out here.

Note: This content does not constitute investment advice and is being presented for informational and educational purposes only.


Show Notes

Portfolio Charts offers a wealth of different portfolio visualization tools and calculators for deeper analysis of your asset allocation, and other personal finance elements. As Eric mentioned in the episode, you’re not likely to find another resource with so many different visualizations available.

Morningstar is perhaps best known as a resource for analysis + ratings for mutual funds. However, the site also has a variety of tools for portfolio analysis and exploration. Some functionality is provided free of charge, while others come with a premium subscription. Importantly, the latter is offered as a 14-day free trial so you can readily use these tools to analyze your asset allocation and then cancel without risk prior to billing.

Big ERN’s SWR Spreadsheet (Early Retirement Now) is a comprehensive planning tool largely aimed at investigating safe withdrawal rate. In line with Big ERN’s standard approach, this is a resource aimed at those desiring detailed, quantitative analysis, and is a bit more “in the weeds”. But having the ability to input your asset allocation along and projected rates of return, is vital to do truly informed modeling. Other tools may be easier starting points, but this one has lots of power when you’re ready to dig deeper.

M1 Pies (M1 Finance) are one of the visualizations Eric discussed to reference the investment approaches of others in the personal finance community, like JL Collins and Paula Pant, which we talked about in Part 1. These are M1 Finance’s flagship portfolio tool, allowing you to see the asset allocations of others and potentially invest in the same approaches.

cFIREsim – This popular tool is the “Crowdsourced Financial Independence and Retire Early Simulator”. cFIREsim is among our favorite sites for performing Monte Carlo analysis of a given FIRE strategy. While you can get started with just a handful of simple parameters, this site is extremely flexible and will allow you to do more complex modeling if that is of interest.

Portfolio Visualizer is a site containing a variety of modeling tools, including the one linked here which allows one to backtest different portfolio asset allocations. While past results are not necessarily predictive of future returns, this approach does allow one to understand the merit + drawbacks of various asset allocations. One useful approach this enables is to compare the performance of your current portfolio vs. a variety of others of your construction.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

Getting Your FIRE Asset Allocation Right. Here’s Ours (Part 1)

What is the best way to divide up your investments among stocks, bonds, and other vehicles? Asset allocation is an essential yet confusing topic. That said, it is an area of critical importance when thinking about early retirement. This is because decisions made about asset allocation can have huge implications on portfolio performance, taxation, and ease of maintenance. Join us for this first episode in a two-part series, as Eric and Jason talk about their portfolios, the merits of simple vs. more complex strategies, the role of bonds, and the risks they considered along the way.

Note: This content does not constitute investment advice and is being presented for informational and educational purposes only.


Show Notes

Our asset allocations:

I do have a very small crypto stake but it’s well below 1% – Jason

The Bogleheads Wiki is an excellent place to begin one’s research on the potentially complicated topic of asset allocation. Named after and inspired by Vanguard founder, Jack Bogle, the Boglehead philosophy is focused on a “small number of simple investment principles that have been shown over time to produce risk-adjusted returns far greater than those achieved by the average investor”. Most commonly these employ so-called “lazy portfolios” of only a few diverse funds that are low cost, easily managed, and capture the performance of the entire market. The site also has an excellent discussion forum.

An Investment Policy Statement (IPS) is an important starting point for any portfolio. The IPS is a document that – according to the Bogleheads wiki: “defines general investment goals and objectives. It describes the strategies that will be used to meet these objectives and contains specific information on subjects such as asset allocation, risk tolerance, and liquidity requirements.” See the link for more information and a template you can use for your own portfolio.

M1 Pies (M1 Finance) are one of the visualizations Eric discussed to reference the investment approaches of others in the personal finance community, like JL Collins and Paula Pant. These are M1 Finance’s flagship portfolio tool, allowing you to see the asset allocations of others and potentially invest in the same approaches.

Portfolio Visualizer is a site containing a variety of modeling tools, including the one linked here which allows one to backtest different portfolio asset allocations. While past results are not necessarily predictive of future returns, this approach does allow one to understand the merit + drawbacks of various asset allocations. One useful approach this enables is to compare the performance of your current portfolio vs. a variety of others of your construction.

“Our Retirement Investment Drawdown Strategy” (Retirement Manifesto) is a great article describing how Fritz employs the bucket strategy to build a retirement paycheck and manage his investment portfolio post-FIRE. This is just one element of our last episode – be sure to watch for helpful background – but is a great example of how one’s asset allocation very much informs how assets are drawn down in the de-cumulation phase of FIRE.

Preferred Stocks (Early Retirement Now) and associated funds, are one of the “hybrid” investment vehicles one could consider in a portfolio. In the linked article, Big ERN talks about how he invests in an ETF made up of preferred stock elements, which have features of both stocks and bonds.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.