Finding My Way in Early Retirement: A 30 Month Check-In

What is early retirement really like? In this episode, Eric checks in with Jason two and a half years after he left his career behind. They discuss his recent financial moves, the impact of inflation, how Jason spends his time, and what’s truly important to him.

Show notes may be found below the video


Show Notes

Essential Background:

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. This is the calculator that Jason referenced in today’s episode.

Buying Treasury Bills and Notes at your brokerage is one of the financial moves we discussed in this video. This article by Harry Sit (“The Finance Buff”) is a really great summary of how you can do that yourself. The well-written post goes through all the details and includes walkthroughs of the process at each of the major brokerages.

Tax Loss Harvesting is a concept we’ve discussed on the show before. This Investopedia article is a good summary of the topic. 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.

CAPE-Adjusted Safe Withdrawal Rate – We talked about this idea in the episode without much explanation. As background, we interviewed Karsten “Big ERN” Jeske previously about safe withdrawal rates (SWR) – this is definitely content you will want to check out if you haven’t before! Subsequent to that conversation, Karsten wrote several blog posts concerning a new “better” CAPE ratio. This first 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 his Safe Withdrawal Rate calculator now can use this factor to model withdrawal rate in retirement.

The Series 65 Exam is “designed to qualify candidates as investment adviser representatives. The exam covers topics that have been determined to be necessary to understand in order to provide investment advice to clients.” If you’re interested in more information on this test and the curriculum it covers, you’ll want to check out this link. Here’s the Kaplan exam prep course that Jason has been taking.


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.

FIRE and Holding Cash – What We’re Doing

These are the show notes for both our original discussion on holding cash, and our follow-up episode where we react and respond to the feedback from our viewers. You’ll find links to both videos below as well. Show notes may be found below the two videos.

Original episode:

How much cash in your portfolio is enough – or too much? In this episode, Eric + Jason discuss the idea of holding cash allocations pre- and post-retirement. Topics covered include emergency funds, the temptation to invest in a down market, bonds, and building cash reserves. Join us as we discuss this essential retirement topic.

We respond to your feedback:

Are you worried about holding cash in this high inflation environment? In a recent video, we talked about the role of cash pre- and post-retirement. In this episode, Eric + Jason review and react to YOUR ideas that you shared with us. Topics covered include bond ladders, high yield savings, real estate, gold and other cash alternatives, and emergency funds. See the links below for the show notes and our earlier episode about what we’re doing about cash.


Show Notes

Essential Background:

Bucket Strategies are a topic we’ve covered numerous times on the show. If you’d like to learn more, we’d recommend the article “How To Build A Retirement Paycheck“.  This is the first of three great posts on Fritz Gilbert’s (The Retirement Manifesto) implementation of this approach. The other two articles in the series are linked here too.

Equity Glidepaths are a type of dynamic asset allocation plan often discussed in retirement planning. In Karsten Jeske’s words, “if we start with a relatively low equity weight and then move up the equity allocation over time we effectively take our withdrawals mostly out of the bond portion of the portfolio during the first few years. If the equity market were to go down during this time, we’d avoid selling our equities at rock bottom prices. That should help with Sequence of Return Risk!”. He covers glidepaths in Part 19 and Part 20 of his Safe Withdrawal Rate series of blog posts.

How does gold perform vs. stock indices? Many people believe gold and other precious medals are “safe havens” to run to during periods of stock market volatility. This chart from Index Fund Advisors shows the reality of the situation. In this example capturing data from 1978-2021, the y-axis shows the rate of return, and the x-axis the annualized standard deviation. You’ll see gold has similar volatility (SD) as the S&P 500, but about half the annual return. Silver is much worse, at twice the annual volatility as the S&P index but twice the volatility.

Bond (or CD) Ladders are one of the topics we touched on in todays episode, and are commonly used by many retirees as part of their fixed income strategy. This post from the Bogleheads wiki is a good resource to understand this instrument better. These days most brokerages make it easy to set up ladders, via simple to use tools you can access on their websites.

Sitting out market volatility may sound like a good idea to some people, taking their money out of equities seeking less volatile investments. But this is really just attempting to time the market. And articles like this one from CNBC demonstrate just how risky a strategy that is. Considering market data going back to 1930, a Bank of America study found that if an investor sat out and missed the S&P 500′s 10 best days each decade, their total return would be 28%. If, on the other hand, the investor stayed in the market all through the ups and downs, the return would have been 17,715%!

Interest rates on savings accounts are always a hot topic when thinking about holding cash – particularly when these far trail the rate of inflation (i.e. cash losing value over time). As an example of how quickly things can change, the interest rate has already doubled in the few months since we originally recorded this episode. Today, there are banks offering >2% interest on high yield savings accounts!


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

Do I Wish I’d Worked One More Year?

With all of the volatility in the market, should you delay retirement by a year? A viewer asked Jason if he would feel more secure had he worked another year or two before retiring early. In today’s episode, Eric + Jason discuss that question and the merits of considering “one more year”. Join us as we discuss this idea and the reasons you might consider that option, what Jason would have missed out on if he had worked longer, and the value he found in retiring when he did.

Show notes may be found below the video


Show Notes

Essential Background:

  • For context on what Jason has been up to since retiring early in June of 2020, don’t miss our episodes discussing his early retirement milestones. The first, What I Learned in My First Year of Retirement is foundational to understanding his RE experience. Not everything went smoothly as you might expect. Here Jason discusses what’s changed, what’s been better, what’s worse, and – importantly – has it lived up to his expectations.
  • A few months ago we published a year two update titled My New Life: Two Years After Early Retirement. In this episode, Eric traveled to California to shadow Jason and find out what his FIRE life is like nearly two years into early retirement. We learn how Jason fills his days, hear his concerns pre- and post-FI, discuss the merits of part-time “fun” jobs, and the reality of finances. It’s interesting to compare this video to the one-year milestone for sure!
  • In today’s episode, Jason talked about his long (five weeks, not seven – he misspoke!) family vacation as one of the most important things that happened since retiring early. Jason discussed this trip as a part of How We Travel: Pre + Post Financial Independence. In this video, Eric + Jason compare notes from their two respective sides of FI and their recent vacations: 7 days for Pre-FI Eric and 5 weeks for Post-FI Jason.
  • Many people claim they’ve achieved financial independence (FI) yet they fall prey to repeated “one more year” extensions. In our experience, this is often due to a lack of confidence in their financial strategy. In Have Enough to Retire (Early)? 10 Steps to Make Sure we discuss ways you can prepare for this key decision, and proceed with confidence.

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 two years since he left his career behind. As he + Eric talked about in today’s episode, it’s almost inconceivable for him to imagine not having had these experiences. If there’s a specific topic you’re seeking, don’t miss this list of all his blog posts to date.

The One More Year Syndrome is a blog post is a post by Fritz Gilbert from Retirement Manifesto. In this article, Fritz discussed why “one more year” made perfect sense for him. Perhaps just as interestingly, this post also collects the thoughts of many other familiar voices from the FIRE community on this topic. It’s definitely a worthwhile read. On a related note, if you haven’t seen our interview with Fritz, be sure to check out Retirement Is Nothing Like I Thought It Would Be. It’s one of our most popular episodes to date for good reason!


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

First Year of “Early Retirement” Lessons Learned

Retiring at 47 is early by any definition. In this episode, Jason reflects on his first year in early retirement after reaching his FI goal in 2020. Not everything went smoothly as you might expect. Learn what’s changed, what’s been better, what’s worse, and – importantly – has it lived up to his expectations? If you’re excited to reach this milestone but still harbor some reservations about crossing into “retirement”, Jason offers a grounded, thoughtful perspective on what to expect and how to prepare for such a life-altering transition.

Be sure to read Jason’s milestone post for additional thoughts and details not covered in the video.


Show Notes

Eric here, checking in with a little behind-the-scenes detail. If you’re a long-time viewer, you’ll have noticed we switched sides in the edit. The reason? I joked with Jason after we finished recording the original episode that his next “skill development task” was to learn Final Cut ProX and cut the episode together. He agreed, not knowing the depth and form my critical feedback would take nor the time and effort making changes would entail! The editing switch was a subtle “tell” that we switched roles. And, although I don’t think this marks a permanent shift in our roles for this project, it did give each of us a better perspective on the skills we bring to the collaboration.


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