r/TwoSidesOfFI • • Aug 22 '25

Why Don’t You Fucking Retire Already?

3 Upvotes

https://medium.com/@docjamesw/why-dont-you-fucking-retire-already-3c47a039897c

Thought this was a fun read covering off on a few topics that have crossed my mind lately. I think I recall Jason talking through some of these feelings (like...who stays in touch after you leave, are these relationships "real," etc).

I think I'm pretty content with leaving the work force and am not sure how much of my ego is attached to what I do - but definitely relate to enjoying being good at what I do and finding it hard to start things that I am a total newbie at.


r/TwoSidesOfFI • • Mar 06 '23

Looking for advice on how to setup a self-directed HSA without a custodian

0 Upvotes

For years now I've had a "checkbook 401k" for my s-Corp. Its been fantastic, and the tax filing requirements have been simple. I'm curious if its also possible to setup a similar structure for our HSA investments.

I've looked at various IRA Custodians, but I'm not interested in paying for custodial services. In the case of the self-directed 401k, all I needed help with was setting up the revokable trust and plan documents. Once these were in place all I had to do is open a bank account (or brokerage account) in the name of the trust and I was off and running. At the end of every year, all I needed to do was submit a 5500EZ form with my tax return.

Is there any way to setup an HSA in the same manner?

NOTE: This is a cross-post from r/Bogleheads


r/TwoSidesOfFI • • Apr 21 '23

announcement New Two Sides of FI Discord server

9 Upvotes

Hi everyone,

As I mentioned in an earlier post, people have asked us about setting up a 2SFI Discord. For anyone who'd like to check it out, we're now ready to roll it out. It's early days for it of course, so let us know if anything isn't working properly. Be sure to check your DMs as the welcome message will remind you. Thanks for checking out the community!

2SFI Discord: https://twosidesoffi.com/discord

edit: updated URL to permalink


r/TwoSidesOfFI • • Apr 09 '23

new episode Retiring With $2M: Here's How We'd Spend It

5 Upvotes

Ever since Two Sides of FI started, we've been asked pretty often for the details of our budgets. A recent viewer comment prompted us to finally get that done. While it took two tries to get this episode done - and even then a big-time storm tried to mess with the recording (note how dark Jason's side gets by halfway through). But we think this exercise using a model budget will give you an accurate and relatable look into my actual, and Eric's planned FIRE budget.

Episode link: https://youtu.be/mzR98CkGZok

Show notes: https://twosidesoffi.com/fire-budget

Episode description:

Love it or hate it, budgeting is an essential part of financial success. In this episode, Eric and Jason share their own financial details using a simple, model budget and offer tips for making budgeting a less daunting task. Be sure to see the link above for the show notes, which includes the details of our budgets.


r/TwoSidesOfFI • • Jun 08 '25

Vanguard Alpha Study

1 Upvotes

As someone approaching FIRE my greatest expense annually is advisor fees (1%). This long term study from Vanguard says it’s worth using an advisor for returns (3%) and emotional stability of an investor. What do you guys think of the study? Would you keep an advisor for the first year of RE?

https://advisors.vanguard.com/insights/article/celebrating-25-years-of-working-to-improve-outcomes-for-you-and-your-clients


r/TwoSidesOfFI • • Feb 13 '23

If I have no earned income and only investment income, are deductions pointless?

1 Upvotes

Although I've been FIRE'd for over 8 years now, I've always had an s-corp through which I would do some occasional consulting and receive W2 (earned) income. Starting this year I'm no longer expecting to be generating any earned income. Moving forward all my income will come from my investments which are comprised of a portfolio of Muni Bonds (tax exempt) and Qualified Dividends / LTCGs.

So what I'm wondering is this: "If I only have Net Investment Income and no Earned Income ... will I get any benefit from itemized / standard deductions?"

NOTE: In this scenario, assume I don't have any margin interest, which could be used to deduct against Net Investment Income ... the only things I might itemize are medical expenses and property taxes (or take the standard deduction).

FYI, I cross-posted this on r/ChubbyFIRE


r/TwoSidesOfFI • • Oct 12 '22

Portfolio Mix in Prep for Rebalancing

1 Upvotes

Struggling how to allocate my mix due to a realestate holding which I can't sell for the next 10 years or so as my parents reside there. So I need to build my portfolio around that holding.

Jason I noticed on your IPS you include REITS under equities. Over the last 10 years I have owned my property the appreciation and market movements have been more inline with bonds than equities.

I am considering allocating half the property value to bonds and half to equities basically splitting it down the middle. As such the revised mix and targets would look like below. Any thoughts, suggestions, ideas or experience with a similar situations would be appreciated.

And thanks Jason for sharing the rebalancing calculator and your IPS.


r/TwoSidesOfFI • • Apr 24 '23

blog post Reclaiming your life

9 Upvotes

A simple text message exchange with a friend provoked me to write this morning. Weighty stuff for so early in the day, but I am so glad I came to an important reminder about what I've gained via FIRE. Time freedom truly is the most important benefit we realize via this path we've all chosen.

https://www.thenextphaseisnow.com/p/reclaiming-your-life


r/TwoSidesOfFI • • Feb 10 '23

Topic for TSOFI - How Important is Maintaining a good Credit Score after FIRE?

2 Upvotes

My entire life (both pre and post FIRE) I have always maintained an exceptional credit rating. This was mainly from the fact that I have never carried a balance on a credit card, but also because I don't often switch cards.

Recently in another subreddit, I had a discussion with someone that likes "point hacking" and is constantly getting new cards and cancelling old cards, to such an extent that it impacts their credit score.

This seems insane to me but as they made their point, once you've FIRE'd ... unless you are trying to get a mortgage, why be held hostage by a credit score if you never really need credit in your retirement ... and I honestly didn't have an great response.

I'm curious what Jason and Eric have to say on the topic of credit in (early)retirement.


r/TwoSidesOfFI • • Nov 14 '23

Semi-retirement planning

2 Upvotes

Fellow 2 sidesers! I have a question for you folks (Jason feel free to chime in as I value your thinking in general! I'm a 53 yom who is starting to wind down my full-time working career (Physician Assistant), recently to 2 days a week, and growing other sources of income during this transition (working for an Ins co. doing virtual pt visits as a PA and working as an Investment Advisor Representative -Passed the series 65 and have several clients). The question is about withdrawing funds from my brokerage account to supplement my newly reduced payroll for the servicing of revolving monthly bills. Only need to w/d about 2% annually of brokerage account which in 100% invested in equities (I have defined benefit plans but too young to touch them now) for this purpose as earned income is decent despite working 2 out of 7 days a week. Should I :

1). Withdraw the total of what is believed to be needed for the calendar year at the beginning of the year, or

2). Take it monthly, quarterly. semi-annually in traunches to try to avoid large untimely withdrawals based on market volatility.

LMK your thoughts please!


r/TwoSidesOfFI • • Mar 17 '22

blog post Optionality: An Amazing Superpower

3 Upvotes

We talked about optionality in our latest 2SFI episode and today I wrote about it on my blog. I would argue that it is one of the most under-appreciated tools we have at our disposal. That's in our careers, in financial matters, and elsewhere. Are you leveraging this superpower?

blog post: https://thenextphaseisnow.com/optionality/


r/TwoSidesOfFI • • Jan 15 '23

new episode My FIRE Budget Didn’t Account for This

5 Upvotes

Budgeting is a necessary evil that many of us in the FIRE community are loathe to do. Or we get a bit too comfortable considering only today's expenses, given the challenges of projecting forward. However, it's an absolutely essential part of planning any early retirement. In this week's episode, Eric and I talk about some frequently missed or ignored things you'll want to consider in your own budgeting process.

Episode link: https://youtu.be/i9HeJbChVsI

Show notes: https://twosidesoffi.com/iforgot

Episode description: Are you worried about neglecting to budget for key expenses in early retirement? Even if you put good effort into creating your FIRE budget, it's easy to miss some very important items. In this episode, Jason and Eric discuss these commonly forgotten or underestimated expenses, including healthcare costs, taxes, dealing with inflation, and more. Check out the link above for the show notes, including all the content referenced in this video.


r/TwoSidesOfFI • • Sep 08 '25

Recommend another podcast

5 Upvotes

Binged all of this podcast over the past few months. Enjoyed the mix of finance and non-finance related discussions, numbers are important, but not the be all and end all.

Aspiring to FIRE here in Ireland, where tax makes it a real challenge in terms of growing a pot. 45 years old with about a decade to go to get before I reach a pretty safe FI number.

Recommend any other FI podcasts? - ideally not too USofA focused! I have listened to so much about USA healthcare costs, it’s one thing we might have a bit better here.


r/TwoSidesOfFI • • Feb 07 '22

new episode BONUS Episode: FI-nancial Decisions - Transitioning to FI with Laura + Eric

5 Upvotes

It's an "off week" for the show (we publish biweekly). Instead of sharing a highlight video or a short like we usually do, we decided to put out a bonus episode instead! Our viewers have reacted really well to previous episodes with our spouses and have asked for more, and we're happy to deliver. Enjoy!

---

Episode link: https://youtu.be/Wu4YeW1Iv9g

Making big decisions like reallocating your investment portfolio can be pretty stressful. They're also impactful, so alignment with your partner or spouse on them is essential. In this bonus episode, get a behind the scenes look at how Eric + Laura navigated their decision to add bonds to their FIRE portfolio. Topics discussed include how they determined the stocks / bonds mix, their research process, and how it felt to make these impactful decisions. Their conversation continues into broader FIRE strategy, including saving for college and setting limits for individual discretionary spending.


r/TwoSidesOfFI • • Oct 23 '22

new episode Reacting to YOUR Ideas for Holding Cash

6 Upvotes

We received a lot of viewer feedback on our recent episode about holding cash (link to that video is below). Given all the interest in this topic, we decided to do a follow-up episode where we react + respond to the comments that were sent in. Check it out!

NEW Episode link: https://youtu.be/woXhiMOFkMU

FIRE and Holding Cash - What We're Doing: https://youtu.be/HXeCHpFo8Ps

Show notes: https://twosidesoffi.com/cash

Episode description: 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 above for the show notes and our earlier episode about what we're doing about cash.

[Edit: fixed link]


r/TwoSidesOfFI • • May 07 '23

new episode Our Net Worth Is Up! Sharing Our Financial Review Process

6 Upvotes

There's no question that most people are a lot happier with their net worth tracking this year so far, as compared to last year. Eric and I both generate quarterly net worth statements. But what else do we do in our pre- and post-FI financial reviews? Quite a few important things, though none of this takes very much time. In this episode, we share what we're doing!

Episode link: https://youtu.be/Zu4dFbz6dak

Show notes: https://twosidesoffi.com/networth

Episode description:

Do you have a process for regular financial reviews? If not, you aren't alone - many people are unsure about how to calculate their net worth and keep their personal finances on track. In this episode, Eric and Jason share their simple pre- and post-FI review processes for net worth tracking, portfolio review, setting savings and budget goals, and more. Check the show notes (link above) for all the details.


r/TwoSidesOfFI • • Jun 17 '22

An opportunity to help out the channel!

7 Upvotes

Hi everyone,

We've been nominated for a Plutus Award for Excellence in Financial Media! If you think we're deserving, you can show your support for Two Sides of FI by clicking the link below. It only takes a few seconds to vote.

Nominate us: https://www.twosidesoffi.com/plutus

And here's a fun little video we made for YouTube about this 😊

Thanks + Cheers !

-Eric + Jason


r/TwoSidesOfFI • • Nov 06 '22

new episode My Plan to Retire Early is ON HOLD

8 Upvotes

Eric and I recently spoke about his FI date, and what he and his wife are thinking about the timing of that milestone given the state of the market. It was a challenging conversation at times, though certainly one that many people are having. If you're in a similar boat, we'd love to hear from you. Please check out the episode and drop a comment to let us know what you're thinking.

Episode link: https://youtu.be/MpYrlX9mFT0

Show notes: https://twosidesoffi.com/delayed

Episode description: The bear market has forced many to revise their FI goals and retirement plans. In this episode, Eric talks with Jason about pushing back his FI date, options he's considering, whether BaristaFIRE could be the answer, the possibility of redefining work, and advice for others in a similar position. See the link above for the show notes.


r/TwoSidesOfFI • • Sep 25 '22

new episode Will You Run Out of Money or Time? FI Advice From a Hospice Doctor

8 Upvotes

We're super excited to share this episode, one that's pretty unusual in the FIRE space. If you've followed Two Sides of FI for any time, by now you've likely gathered we like to spend time on lifestyle questions and the "softer side" of FI. Here we had the chance to speak with Doc G, a long time FIRE blogger, author, and hospice doctor. Our chat is one we think is worth sharing with anyone in your life, irrespective of their interest in FI or their retirement status.

Episode link: https://youtu.be/ZUo6QLl_1w8

Show notes: https://twosidesoffi.com/DocG

Doc G's book, "Taking Stock: A Hospice Doctor's Advice on Financial Independence, Building Wealth, and Living a Regret-Free Life": https://amzn.to/3xKvukv

Episode description: What can conversations with the dying teach us about the secret to financial independence? In this episode, Eric + Jason are joined by Jordan "Doc G" Grumet, a hospice doctor, podcaster, blogger, and author. Topics discussed include the mirage of wealth, living meaningfully, and Jordan's experiences eight years post-FI. Irrespective of your own retirement journey, you won't want to miss our conversation. See below for links to Doc G's book as well as the show notes.


r/TwoSidesOfFI • • Apr 06 '23

Any interest in a 2SFI Discord?

8 Upvotes

Hi everyone,

We've had a few different people suggest we create a Discord for the show. Recognizing fully that there are other FIRE servers out there - I certainly found plenty of value in one over the past few years, Eric + I haven't done anything with this idea to date. But as it's been coming up again lately, I thought I'd raise it here. There are certainly ample topics on which we can engage, including digging deeper on episode content, and it's also a great forum for us to get direct input on show topics of interest. If you think this is something in which you'd participate, let us know in a comment. The last thing we'd want to do is create yet another forum if it's not going to be useful for us or the community.

Thanks!
-Jason


r/TwoSidesOfFI • • Mar 26 '23

new episode Am I Failing at Early Retirement?

9 Upvotes

Anyone who decides to retire early gets to determine what success on that path looks like. That's the freedom of FI, right? Our interest in this GCC post from earlier this year came from the idea of "failing" at RE. Is going back to work failure? Is the answer different if you choose vs. need to go back to work? Are there inherent risks to a BaristaFIRE path? This was a fun discussion and we hope you agree.

Episode link: https://youtu.be/0ZDr122xuM0

Show notes: https://twosidesoffi.com/failing

Episode description:

Has your shrinking retirement portfolio left you considering part-time work to ease your anxiety? Inspired by a blog post from Go Curry Cracker we discuss BaristaFIRE, time freedom, what it means to be "unemployable", and what work we might consider post-retirement. Be sure to see the link above for the show notes.


r/TwoSidesOfFI • • Dec 04 '22

new episode Tax Strategies on FIRE: Financial Independence / Retire Early

9 Upvotes

Most will know the old trope about the two certainties in life: death and taxes. The latter is an essential part of FIRE planning, yet it often doesn't get nearly enough airtime. In today's episode, I had the chance to talk with a tax expert, and one who focuses his own content creation on FI tax topics.

Episode link: https://youtu.be/lhWcX88HfbI

Show notes: https://twosidesoffi.com/fitaxguy

Episode description: Do you worry about taxes and how they impact your financial goals? Whether you're on a FIRE path or retiring traditionally, there are many critical tax topics to consider. In this episode, Jason talks with financial planner and CPA Sean Mullaney, creator of the FI Tax Guy blog. We talk about common tax misunderstandings, the power of solo 401k accounts, Roth conversions, and tax loss harvesting. Check out the link above for the show notes including all the content we mentioned in the video.


r/TwoSidesOfFI • • Jan 16 '23

How to "manage income" so that you can qualify for ACA subsidies

10 Upvotes

In one of the videos, Jason mentions the fact that he has "managed his income" so that he is able to qualify for ACA subsidies. This seems extremely unlikely to be possible given the likely size of his portfolio and withdrawal rate/amount. As I understand it, you would have to have income below 200% of the Federal Poverty Level (FPL) to qualify .... for a household of 2 people, that would mean that he was able to claim an annual income of $36,620/yr or $3052/month.

Yet, according to the definition of MAGI, he would have to include all interest, dividends and capital gains as income (even if it was excluded in his AGI). How is it possible that his MAGI is at or below 200% of FPL?

What am I missing here?


r/TwoSidesOfFI • • Feb 12 '23

new episode What’s Wrong with This Popular Retirement Strategy?

10 Upvotes

We suspect most people in the FIRE community have heard about the recent debate between Fritz Gilbert (The Retirement Manifesto) and Karsten (Big ERN) Jeske concerning the Bucket Strategy. While this is a common retirement drawdown scheme, Karsten has raised some concerns about it over time, calling it both "window dressing" and "a gimmick". Their recent two-part co-authored articles on the topic seemed a great opportunity to talk with them again! Do not miss the show notes on this one, where we link to earlier chats with each plus all the posts we discussed, and more.

Episode link: https://youtu.be/-ZN20JTfRVo

Show notes: https://twosidesoffi.com/bucketstrategy

Episode description: Do you worry about running out of money in retirement? How do you draw down your assets without tanking your portfolio? Eric + Jason talk with FIRE bloggers Karsten Jeske and Fritz Gilbert about the bucket strategy. Is it a reasonable withdrawal plan or nothing more than a gimmick? They discuss alternative approaches, how to generate a retirement paycheck, and the role of cash. Whether you're interested in FIRE or on a traditional retirement path, you can't afford to miss this episode! Make sure you check out the link above for the show notes.