Ask an Early Retiree Anything! Live Q&A with Jason from Two Sides of FI

Are you on the FIRE path or interested in learning more about early retirement? Three years ago I retired from my career at age 47 after reaching financial independence the prior year. This video is from a livestream where community members had the opportunity to ask me questions about what my experience has been like. Thanks to all who joined!

Don’t miss the extensive show notes below, which list all the episodes and resources discussed in the episode.

Show notes may be found below the video


Show Notes

Essential Background:

Here are links to the episodes Jason talked about in the show. In many cases these point to show notes, which contain not only the episode video itself, but also a variety of associated content meant to help support the content. Check them out!


Resources Mentioned:

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In this episode we talked about the new Two Sides of FI Discord server. If you’re not familiar, this is an instant messaging social network. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests!

Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first 1.5 years after he retired from his career, and started even before Two Sides of FI began. Get more information on those archived posts here.

In this episode, Jason mentioned Empower (formerly Personal Capital) for summarizing his portfolio performance as a part of rebalancing. Both him and Eric really like this free tool for tracking investment accounts, understanding asset allocation + rebalancing opportunities, and monitoring net worth. Empower employs a simple account linking process to make it a more automated experience. Give it a try risk-free! (affiliate link; free program )

Do you have a copy of our free Rebalancing Calculator? This simple tool can help you make your own decisions about buying and selling in order to rebalance your portfolio. If you’d like something more DIY, this is a calculator you should consider.

In case you missed the link above, our popular three-part tutorial series on the Safe Withdrawal Rate (SWR) Toolbox can be found here.

The Retirement Income Style Awareness (RISA) is a tool by Wade Pfau (mentioned today) and the team at Retirement Researcher. It came from research performed on individual styles, risk tolerance, and other factors, and is aimed at deriving a personal retirement income strategy. Fritz Gilbert at Retirement Manifesto posted a nice write up on this last year, which we’d recommend. If you’re interested in learning more about this assessment, check out Wade’s book: “Retirement Planning Guidebook: Navigating the Important Decisions for Retirement Success”.

Die with Zero: Getting All You Can from Your Money and Your Life by Bill Perkins, is discussed often in the FIRE community – so no surprise it came up in this episode. It’s intended as a “practical guide on how to get the most out of your money—and out of your life”. If you like the aim of prioritizing memorable experiences far ahead of simply accumulating money for later in life, you’ll definitely want to check it out.


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

Never Run Out of Money in Retirement – Use This Free FIRE Calculator!

Show notes may be found below the videos, all of which are also available on our Safe Withdrawal Rate series playlist.

Part 1: Walkthrough of the SWR Toolbox

Do you want to avoid the biggest retirement risk? This simple to use tool will let you model your safe withdrawal rate and help ensure you don’t run out of money. In this walkthrough video, we teach you how to use this powerful, flexible, and FREE tool created by Karsten Jeske. Using the SWR Toolbox, you can ensure that you have a personalized plan that works with your own financial situation.

Part 2: Eric + Jason discuss how they’re using the SWR Toolbox and how Jason is struggling to spend as much as he can safely do in early retirement

How much money can you safely spend in retirement? In part two of this series on safe withdrawal rates, we discuss the #1 tool we’ve found to help you answer that question. Topics covered include the SWR Toolbox, our thoughts on Social Security, the challenges of spending in retirement, and how to get comfortable with increasing your withdrawal rate.

Part 3: Walkthrough of the CAPE-Based Rule tab in the SWR Toolbox

Do you like the idea of a portfolio withdrawal strategy that can’t run out of money? This walkthrough video is the third part in our Safe Withdrawal Rate (SWR) series, and teaches you how to model a variable withdrawal strategy based on the CAPE ratio. Using this powerful and FREE tool created by Karsten Jeske, you can design a personalized plan that works with your own financial situation.

Part 4: How Jason builds his retirement paycheck using the SWR Toolbox

How do you plan to set up your retirement paycheck to avoid running out of money? In this episode, Jason talks with Eric about how he uses a free online tool to manage his finances in early retirement. Topics covered include his variable withdrawal strategy, managing cash, portfolio rebalancing, and much more.


Show Notes

Download the Safe Withdrawal Rate (SWR) Toolbox

  • The Safe Withdrawal Rate Toolbox is available via Karsten Jeske’s Early Retirement Now blog. The current version can be downloaded via Part 28 of the SWR series. This is also the post where the revisions to the calculator are described. To see the history of this tool, you’ll need to go back to Part 7. We found reading both posts to be essential to really understand how the tool works. Please ensure you follow the directions in the video to make your own copy of the tool. There’s no need to email Karsten to request edit rights!

Essential Blog Posts

Safe Withdrawal Rate series: This is the landing page for the 61-part SWR series (it will surely continue to grow) for which Karsten is best known. Be sure to start with the guidance he provides on how to navigate this great but expansive content. Many essential topics are covered in the series and not all of them involve deep dives into math! While we think all of his posts are interesting, you’ll find guidance below about the specific articles we think are most important to the topic of this video – in addition to Parts 28 and 7 listed above.

In Part 3 of this series, we covered the CAPE-Adjusted Safe Withdrawal Rate tab in the Toolbox, and described what the Shiller CAPE is. For those who want further details, there’s ample material available on Karsten’s blog for you to review. In addition to the introduction to the feature provided in Part 28, Big ERN recently wrote several posts concerning a new “better” CAPE ratio – i.e. CAPE model 2 in the SWR Toolbox. This article introduces the concept, while the next, “The 4% Rule Works Again! An Update on Dynamic Withdrawal Rates based on the Shiller CAPE – SWR Series Part 54” dives into details on how the SWR Toolbox employs this factor to model a variable withdrawal strategy. To go a level deeper on the foundations of this approach, including how to evaluate these types of strategies, you’ll definitely want to read Part 18: Flexibility and the Mechanics of CAPE-Based Rules.

Sequence Risk is more important than your average return rate. Surprised? Be sure to check out Part 15: More Thoughts on Sequence of Return Risk. As mentioned in the video, SWR is overwhelmingly determined by the first 10-15 years of portfolio drawdown.

Are you the kind of person who wants all the gory details about the math underlying the SWR Toolbox? If so, you won’t want to miss Part 8: Technical Appendix. It’s got all the information you need to fully understand how Karsten’s approach works. There are also some good references at the bottom of the post on related material found elsewhere.

Did you know we’ve spoken to Karsten twice before? “What the FIRE Community Gets Wrong” was the first time he came on Two Sides of FI. We covered a lot of ground in this episode about safe withdrawal strategies – so much so that we also released a follow-up video called “Karsten Spoke, We Listened. Here’s What We Learned”. These two episodes are popular with our audience for a good reason and are definitely worth viewing for anyone interested in SWR strategies.

Our second conversation with Karsten also featured Fritz Gilbert (from The Retirement Manifesto), in a continuation of their debate about the merits of bucket strategies. In “What’s Wrong with This Popular Retirement Strategy?” we covered a lot of ground that you won’t want to miss!

Other Show Notes

We get a lot of questions about portfolio rebalancing. Would you like a free tool to help you rebalance your portfolio using the same approach we do? This calculator provides a convenient mechanism to enter and track your asset allocation, flag when any assets exceed your allocation targets, and model any rebalancing that may be needed. It’s really easy to use as you’ll see in our introductory video.

In Part 4, Jason mentions his “IPS” or Investment Policy Statement. Chasing short term market conditions adds a lot of risk to reaching your long term investing goals. In “Is This a Part of Your FIRE Plan?”, we talk about how an IPS can help ensure you stick to your strategy, and avoid market timing and other investing pitfalls. Topics covered include defining portfolio makeup + objectives, the mechanics of cash generation + rebalancing, and why you might consider implementing an IPS yourself

cFIREsim (or  Crowdsourced Financial Independence and Retire Early Simulator) is a very popular and powerful FIRE calculator created by Lauren. We found a lot of value in this tool throughout our FIRE journey, and clearly many others do as well. In the developer’s words, “What can cFIREsim do? At its core, you can enter information in the a few simple inputs and return the basic simulation. At its most complicated, it can determine your portfolio success based on 80 individual portfolio adjustments, multiple types of inflation, multiple types of market returns, and graphically show you the results. There are many options to choose from outside of the ‘Basic Inputs’ “, including a number of variable withdrawal strategies under “Spending Plan”.

Variable Percentage Withdrawal (VPW) is another method besides CAPE-adjusted WR for allowing market conditions to influence the amount you take out of your portfolio in drawdown. As mentioned in parts 2 and 4, VPW is popular among some adherents the Bogleheads approach to investing. As you’ll read at this link, this method “adapts adjustments to portfolio withdrawal amounts to the retiree’s retirement horizon, asset allocation, and portfolio returns during retirement… to allow the retiree to spend most of the portfolio using return-adjusted withdrawals. By adapting withdrawals to market returns, VPW will never prematurely deplete the portfolio.”

stickK is the app Eric mentioned in Part 2 to help track adherence to a goal – like keeping to spending your planned withdrawal rate. Created from a behavioral economics framework, stickK allows you to create “Commitment Contracts, [which are] a binding agreement you sign with yourself to ensure that you follow through with your intentions—and it does this by utilizing the psychological power of loss aversion and accountability to drive behavior change.” We’ve not tried this yet but this is a pretty appealing (an a little scary) idea!


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

You Asked, We Answered. FIRE Q&A

Answering your financial independence, retire early (FIRE) questions, including the one we’re asked most often. This special Ask Us Anything format commemorates the 50th episode of Two Sides of FI. THANK YOU to all who submitted questions and for your continued support of the show!

Show notes may be found below the video


Show Notes

First, THANK YOU so much again for all your support of Two Sides of FI. We’d never have achieved this 50 episode milestone without all the engagement and encouragement we receive from you, our community. We truly appreciate you and are thankful for your constant support.

We are often asked how to support + promote the show. Here are three simple ideas which we humbly suggest: 1) Share a link to our channel with people who you think can benefit – via social media, 1:1, or however works for you. 2) Use the ‘like’ feature on videos and subscribe (click here!) to the channel. The YouTube algorithm sees these signals as indications of merit, and they play a vital role in helping to promote our content. 3) Consider rating + reviewing the podcast – even if you always watch it on YouTube. Apple Podcasts is the most important tool out there to drive visibility on the audio format. We get thousands of podcast downloads each month yet have <80 total reviews at the time this episode went live. Thank you!

Essential Background:

  • Our first episode, “Our Financial Past and our FIRE Present – Two Sides of FI is where it all began for the show. 50 episodes later, there certainly have been plenty of changes – and improvements (particularly on Jason’s side of the screen, as he likes to point out). This episode is the best place to learn about our financial backgrounds a bit better.
  • So, What’s Your Financial Independence (FI) Number? was one of our early popular – and controversial videos. We’ve got a long history with this question, and you won’t want to miss the end of today’s episode to hear our current thoughts on it. But this earlier installment sets the stage for this essential question + many FIRE fundamentals.
  • We’ve actually done another Q&A episode: “Answering Your Financial Independence Questions”. In this video, we tackled topics including changing withdrawal rates, our FI numbers, redefining identity in early retirement, rental real estate, and more.
  • In today’s episode we referenced a fun experiment, captured in “We Each Hired a Flat Fee Financial Advisor. Was it Worth It?”. Prior to this video, we each hired the same fee-only, advice-only advisor to evaluate our portfolios and answer our questions. We then shared how we found this advisor, what the process was like, the specific questions + answers we had, and who we believe could benefit from such a service.
  • Safe Withdrawal Rate has been an ongoing topic for us on 2SFI, and naturally it came up here as well. Did you know we spoke with SWR expert, Karsten Jeske? To see that episode, our follow-up conversation, and get the best collection of all the resources we have on this topic (including the free SWR Toolbox), you’ll want to see this show notes page.

As a complement to Two Sides of FI, Jason’s milestones blog posts are perhaps the easiest way to understand what his journey has been like since retiring early. In these articles, he discusses candidly what he’s felt, experienced, and achieved in the 2+ years since he left his career behind. If there’s a specific topic you’re seeking, don’t miss this list of all his blog posts to date.

Top Five Regrets of the Dying: A Life Transformed by the Dearly Departing is a book by Bronnie Ware that we mentioned in this episode. It originally started as a blog post, outlining the most common regrets that the people she had supported through palliative care had expressed. The post quickly blew up and was viewed by more than three million readers worldwide in its first year. Bronnie subsequently wrote this fascinating and meaningful book capturing all that she learned.

CoastFI came up in a question we addressed in this video. This is a term used to describe someone who isn’t yet FI but has already put in the necessary effort to mathematically achieve that goal without further contributions. Did you know we talked with someone on this topic in an podcast-only episode last year? If you missed it then, you’ll definitely want to check out A CoastFI Path to Financial Security: An Interview with Catherine.

Eric has talked about his “Possible Futures” Notion page in several episodes to date. Here is a screenshot of the kind of information he and Laura track here

In today’s episode, we shared footage of what Eric’s filming setup looks like. For the full details on the equipment he uses, check out this page.

By his own description, Jason’s filming setup is more “bespoke”. They say a picture is worth a thousand words:


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

Answering Your Financial Independence Questions

You asked, we answered. Bringing the Two Sides of FI together to discuss changing withdrawal rates, Jason and Eric’s own FI numbers, redefining identity in early retirement, rental real estate, and more.

Want your question featured on an upcoming show? Drop a comment on the video or reach out on our contact page.


Show Notes

Given the diversity of topics and tools discussed in this episode, it was challenging to go into much depth on any one of them. We’ve shared more information below on several of these items so that you can get the full details on each.

  1. Our FIRE numbers: We only briefly touched on this topic in this episode, but we’ve actually done an in-depth two-part series in the past. “So, What’s Your FI Number? Sharing Ours Here” is the first, and addresses the question of how to determine how much you need to achieve financial independence. We decoded the math used to calculate our own FI targets, talked about the different flavors of FIRE, and shared where our numbers fall on the FIRE spectrum. The second part of this series, “Discussing our FI Numbers : Changing our Minds, Talking to Family”, goes a step further. There we talked about how our early FI goals and calculations underestimated today’s needs. We then went beyond the math of financial independence to discuss the psychological aspects, including important conversations we had along the way with family and friends.
  2. Modeling your FI plan’s success: In this episode we showed some examples of modeling using cFIREsim, one of our favorite tools for examining the likelihood of your assets lasting the duration of your retirement timeline. This is a commonly used and highly regarded tol among the FIRE community. Newretirement.com is another great site (with both free and subscription options) that provides similar functionality, while including more in depth planning options. Both can be found on the Tools section of our Resources page.
  3. Modeling rent vs. buy decisions: While this wasn’t a major topic in this show, it is a question that comes up often both pre-FIRE and when thinking about modeling housing costs post-FIRE. It’s easy to model scenarios using the Rent vs. Buy calculator at SmartAsset.com.

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