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9 to FI - Financial Independence Conversations episodes
- The Hardest Thing About Early Retirement | 9 to FI 049
The Hardest Part of Early Retirement: Mental Health, Rumination, and Finding Happiness
Josh and Elliot discuss common challenges of early retirement—shifting from saving to spending, boredom, healthcare uncertainty (ACA subsidies and planning), loss of identity and guilt when saying you’re retired, social isolation, and fear of running out of money (Monte Carlo simulations, one-more-year syndrome, expense lumpiness, and flexibility). Fourteen months into early retirement, Josh says most of these weren’t major issues for him, but his biggest struggle has been mental health and happiness: after an initial honeymoon, stress from helping with a newborn granddaughter in the ICU, sleep disruption, recurring funks, irritability, and rumination over trivial and family/tenant issues. He describes using reframing, reducing complaining, reading self-help and mental-health books, drafting an “It’s a Wonderful Life” personal policy statement, and focusing on controlling what he can; Elliot shares returning to therapy and the idea that money only solves money problems.
00:00 Early Retirement Struggles
01:10 Saver To Spender Shift
02:58 Boredom And Purpose
06:05 Planning The Tuesday Life
10:18 Healthcare And ACA Fears
13:16 Identity And Guilt
21:31 Isolation And Community
24:48 Running Out Of Money
34:15 Mental Health Reality Check
42:01 Tools To Stop Rumination
45:10 Therapy And Taking Control
57:33 Closing Thoughts
Do you have feedback or suggestions? We want to hear from you!
Contact Elliot: [email protected]
Contact Josh: [email protected]
Josh’s other podcast: Stuck In Beta
Josh’s YouTube channel: How To Fix It Workshop
Any of these products help the show. Thanks for your support!
Buy Us a Coffee - One time donation or monthly, it’s up to you
We both use Mint Mobile and save a ton on our phone plan:
Empower is Josh’s choice for Net Worth and Budgeting
Wanna create a podcast? We use Descript
Looking for a new credit card? We’re big fans of Chase
Want to save money on gas, groceries and dining out? Try Upside!
Books mentioned in this episode:
Come find us and subscribe on YouTube: http://www.youtube.com/@9toFI
58 min - Why we didn't save for our kids college. | 9 to FI 048
College Planning, 529 Tradeoffs, and Flexible Ways to Support KidsElliot and Josh chat about summer heat, an upcoming Colorado trip for Camp FI, and how long emails get ignored, then segue into college expenses and planning. Elliot references an Inside Out Money episode contrasting underfunding vs. heavy 529 saving (including a $600,000 example) and discusses 529 flexibility alongside concerns about over-saving and restrictions. Josh explains why his family avoided 529s, noting his children took varied paths (one degree, two partial, one no college), and describes focusing on controllable cost reducers like Missouri’s A+ scholarship (two years community college tuition) and earning credits in high school, plus covering books/fees and encouraging tuition reimbursement jobs. They debate ROI of expensive schools, the value of the “college experience,” alternative careers, and ideas for gifting money with guardrails or paying loans later to create “skin in the game,” acknowledging uncertainty about timing and kids’ choices.00:00 Summer Heat Banter00:54 Camp FI and Manitou Incline01:52 TLDR and Email Overload03:29 College Planning Kickoff04:19 529 Plans and Flexibility10:02 Scholarships and Community College12:56 Debt, ROI, and College Value21:35 Rethinking the Traditional Path28:14 Kids Finding Their Own Way37:53 Gifting Money and Skin in Game45:26 Wrapping Up and Next Time
Do you have feedback or suggestions? We want to hear from you!
Contact Elliot: [email protected]
Contact Josh: [email protected]
Josh’s other podcast: Stuck In Beta
Josh’s YouTube channel: How To Fix It Workshop
Any of these products help the show. Thanks for your support!
Buy Us a Coffee - One time donation or monthly, it’s up to you
We both use Mint Mobile and save a ton on our phone plan:
Empower is Josh’s choice for Net Worth and Budgeting
Wanna create a podcast? We use Descript
Looking for a new credit card? We’re big fans of Chase
Want to save money on gas, groceries and dining out? Try Upside!
Books mentioned in this episode:
Come find us and subscribe on YouTube: http://www.youtube.com/@9toFI
47 min - Net Worth vs Investable Assets - There's a BIG DIFFERENCE! | 9 to FI 047
Net Worth vs. Investable (Liquid) Assets: What Really Funds Financial IndependenceJosh and Elliot discuss the difference between net worth and investable assets (liquid net worth) and why confusing them can mislead financial independence planning. Net worth is assets minus liabilities and can include a primary residence, cars, and real estate equity, but those assets may not be easily tapped to fund living expenses without selling. Investable assets—such as a 401(k), Roth IRA, and brokerage accounts—are the liquid holdings typically used for withdrawal-rate calculations like the “$1M for $40k at 4%” baseline. They explore how real estate adds complexity because equity doesn’t translate predictably into cash flow due to rents, appreciation, vacancies, repairs, and capital expenditures, and they emphasize the importance of decumulation mechanics, withdrawal strategy, and understanding where retirement income will actually come from.00:00 Net Worth Basics02:03 Defining Investable Assets03:06 Liquid Net Worth Explained05:36 The Million Dollar Myth06:52 Real Estate Equity Limits09:10 Returns and Leverage Tradeoffs11:28 Real Estate Cash Flow Reality15:29 Baseline FI and Projections21:51 Decumulation and Drawdown Plan26:46 Wrap Up and Take Action
Do you have feedback or suggestions? We want to hear from you!
Contact Elliot: [email protected]
Contact Josh: [email protected]
Josh’s other podcast: Stuck In Beta
Josh’s YouTube channel: How To Fix It Workshop
Any of these products help the show. Thanks for your support!
Mint Mobile - We both use Mint Mobile and save a ton on our phone plan: https://my.mintmobile.com/refer/aEWp5rL
Empower is Josh’s choice for Net Worth and Budgeting
Wanna create a podcast? We use Descript
Looking for a new credit card? We’re big fans of Chase
Buy Us a Coffee - One time donation or monthly, it’s up to you
Want to save money on gas? Try Upside!
Books mentioned in this episode:
Come find us and subscribe on YouTube: http://www.youtube.com/@9toFI
28 min - WHY Pursue FI?: Our Personal Journeys | 9 to FI 046
Finding Your "Why" for Financial Independence: Security, Time, Health, and Giving BackJosh and Elliot open with a humorous aside about “newspapers,” then discuss a Choose FI podcast episode featuring Allen Hansen and Kristen Knapp that raised the question of why people pursue financial independence beyond the math. They share how early experiences shaped their motivations: Josh describes childhood money trauma, being teased for Walmart clothes, and later bankruptcy, foreclosure, and divorce, leading him to seek financial security and better money habits; Elliot recalls private-school comparisons with wealthier peers and wanting to ensure he had enough. Their “why” evolves to autonomy and buying time, being more present for kids (including the value of FU money), improving physical and mental health by escaping sedentary screen-based work, and helping others through volunteering and sharing lessons. They emphasize planning what FI life will look like, expecting change, and using intentional, flexible time-bucketing.00:00 Cold Open Banter02:10 Why Pursue FI04:05 Money Trauma Origins10:19 Autonomy And Time12:09 A Perfect Retired Day14:28 Parenting And FU Money16:47 Health Wellness Benefits22:06 Giving Back And Service29:16 Retire To Something36:07 Planning Time And Change40:30 Wrap Up And Farewell
Do you have feedback or suggestions? We want to hear from you!
Contact Elliot: [email protected]
Contact Josh: [email protected]
Josh’s other podcast: Stuck In Beta
Josh’s YouTube channel: How To Fix It Workshop
Any of these products help the show. Thanks for your support!
Mint Mobile - We both use Mint Mobile and save a ton on our phone plan: https://my.mintmobile.com/refer/aEWp5rL
Empower is Josh’s choice for Net Worth and Budgeting
Wanna create a podcast? We use Descript
Looking for a new credit card? We’re big fans of Chase
Buy Us a Coffee - One time donation or monthly, it’s up to you
Want to save money on gas? Try Upside!
Books mentioned in this episode:
Come find us and subscribe on YouTube: http://www.youtube.com/@9toFI
41 min - Asset Allocation vs. Asset Location: Yes, There’s a Difference
Asset Allocation vs. Asset Location: Building Flexibility and Tax EfficiencyElliot and Josh discuss the concepts of asset allocation and asset location, noting that financial terminology can be unclear and that fee-only fiduciary advice may be useful, while the AUM model is discouraged. They review common asset types (stocks, bonds, cash equivalents/treasuries, real estate, alternatives like gold, derivatives, crypto, and collectibles) and why cash can be a depreciating asset due to inflation, though it can serve as an emergency fund. They explain allocation as the mix of assets based on time horizon and risk (more stocks when younger, de-risking toward bonds/cash/fixed income nearer retirement), sharing their aggressive allocations and Josh’s real-estate-heavy net worth. They define location as placing assets across taxable, tax-deferred, Roth “tax-free,” and HSA accounts, highlighting tax impacts (e.g., bonds in tax-advantaged accounts), ACA subsidy cliffs, and withdrawal flexibility, and they reflect on the complexity of decumulation strategies such as Roth conversions and 72(t).00:00 Welcome and Setup02:15 Why Finance Feels Vague05:09 Asset Types Overview07:45 Cash as an Asset11:06 Allocation Basics and Risk14:09 Their Current Allocations17:33 Fixed Income Explained20:57 Asset Location Accounts25:41 Tax Efficient Placement34:41 Decumulation Mindset Shift38:41 Wrap Up and Farewell
Do you have feedback or suggestions? We want to hear from you!
Contact Elliot: [email protected]
Contact Josh: [email protected]
Josh’s other podcast: Stuck In Beta
Josh’s YouTube channel: How To Fix It Workshop
Any of these products help the show. Thanks for your support!
Mint Mobile - We both use Mint Mobile and save a ton on our phone plan: https://my.mintmobile.com/refer/aEWp5rL
Empower is Josh’s choice for Net Worth and Budgeting
Wanna create a podcast? We use Descript
Looking for a new credit card? We’re big fans of Chase
Buy Us a Coffee - One time donation or monthly, it’s up to you
Want to save money on gas? Try Upside!
Books mentioned in this episode:
Come find us and subscribe on YouTube: http://www.youtube.com/@9toFI
40 min - Is Early Retirement still achievable for a 25 year old starting now? | 9 to FI 044
Is Financial Independence Still Repeatable? Talking “Beating the System,” Time, and Modern OptionsJosh asks Elliott about co-presenting an FI 201 session, which Elliott says went well with positive feedback and a turnout in the mid-60s to 70s, and they discuss continuing educational events to complement the group’s social focus. Josh then shares a comment from his 25-year-old son Caleb after Josh’s one-year “quitiversary,” saying Josh “beat the system” and implying retirement is getting harder, prompting a discussion about generational doom-and-gloom versus broader historical data. Elliott argues time is a 25-year-old’s advantage and that FI remains achievable by creating a savings gap and investing rather than holding cash, while Josh notes past high mortgage rates and today’s broader lifestyle options enabled by the internet and gig work. They discuss Caleb’s low-cost van-travel lifestyle, investing for long horizons, ignoring market-prediction headlines, and avoiding speculation like crypto or gambling.
00:00 FI 201 Recap
02:31 Quitiversary Reflection
05:44 Is FI Still Possible
08:32 Boomers Rates And Housing
10:07 Caleb Van Life Economics
14:14 Alternative Paths To Work
20:45 Spending Less Superpower
25:38 Markets Headlines Noise
30:06 Wrap Up Advice
Do you have feedback or suggestions? We want to hear from you!
Contact Elliot: [email protected]
Contact Josh: [email protected]
Josh’s other podcast: Stuck In Beta
Josh’s YouTube channel: How To Fix It Workshop
Any of these products help the show. Thanks for your support!
Mint Mobile - We both use Mint Mobile and save a ton on our phone plan: https://my.mintmobile.com/refer/aEWp5rL
Empower is Josh’s choice for Net Worth and Budgeting
Wanna create a podcast? We use Descript
Looking for a new credit card? We’re big fans of Chase
Buy Us a Coffee - One time donation or monthly, it’s up to you
Want to save money on gas? Try Upside!
Books mentioned in this episode:
Come find us and subscribe on YouTube: http://www.youtube.com/@9toFI
31 min - FI 201 - Moving to Crypto and Gambling | 9 to FI 043
Previewing FI 201: Investing, Risk, Accounts, and SpeculationJosh and Elliot discuss Elliot’s upcoming FI 201 presentation for their local Choose FI group, co-presented with Alan Hansen, after their well-attended FI 101 session drew about 75 people and was later shared within the Choose FI community. Elliot outlines FI 201 topics including saving vs investing vs speculating, investment risk and risk tolerance, market-history return graphs and whether to panic during downturns, types of accounts (tax-deferred, Roth/after-tax, HSA), asset types, asset allocation and asset location, and sharing real examples of their households’ asset distribution (taxable, tax-deferred, cash, equities, 529s) plus mistakes and resources. Taxes are being moved to a separate future class, and they mention the book “Tax Planning To and Through Early Retirement.” They also note covering crypto, gambling, options/futures, and hard assets, and discuss compounding and long-term comparisons among inflation, T-bills, and the S&P 500.00:00 Welcome And Setup00:04 Why FI 201 Now01:34 FI 101 Recap Impact03:39 FI 201 Agenda Overview07:07 Asset Location Questions09:51 Future Classes And Taxes11:57 Terminology And Nomenclature15:09 AI Slides Experiment18:00 Speculation Crypto And Gambling22:20 Young Investors Day Trading26:25 Net Worth Milestones27:51 Compounding And Returns Demo29:06 Wrap Up And GoodbyeDo you have feedback or suggestions? We want to hear from you!
Contact Elliot: [email protected]
Contact Josh: [email protected]
Josh’s other podcast: Stuck In Beta
Josh’s YouTube channel: How To Fix It Workshop
Any of these products help the show. Thanks for your support!
Mint Mobile - We both use Mint Mobile and save a ton on our phone plan: https://my.mintmobile.com/refer/aEWp5rL
Empower is Josh’s choice for Net Worth and Budgeting
Wanna create a podcast? We use Descript
Looking for a new credit card? We’re big fans of Chase
Buy Us a Coffee - One time donation or monthly, it’s up to you
Want to save money on gas? Try Upside!
Books mentioned in this episode: Tax Planning To And Through Early Retirement - https://amzn.to/4396bro
Come find us and subscribe on YouTube: http://www.youtube.com/@9toFI
30 min - Should I Take An EARLY WITHDRAW From My 401k to Fund Discretionary Spending? | 9 to FI 042
Should We Tap a 401(k) Early for Home Upgrades? A Middle-Class Trap Liquidity DebateJosh and Elliot discuss the “middle class trap” idea—having most wealth tied up in 401(k)s and home equity—and how it affects liquidity and flexibility. Josh is retired with nearly $2.9M net worth, outlines cash ($65K), taxable brokerage (~$95K), $1.4M tax-deferred 401(k)s, paid-off home with a $135K HELOC at 7.75%, rental property equity (~$600K), and his wife Lori’s income (~$4,500/month) and pension value. They consider funding roughly $60K of long-delayed home projects (deck, fence, hardscaping). Josh explores early 401(k) withdrawal while Lori works (12% bracket plus 10% penalty) versus using cash/taxable, HELOC, rental cash flow, Roth conversions, 72(t) strategies, or a margin loan, debating taxes, penalties, opportunity cost, and psychological comfort with liquidity and debt.00:00 Basement Backdrop Banter01:05 Hybrid Worker Setup02:09 Middle Class Trap Debate06:56 Real Estate vs Liquidity10:53 Home Projects Wish List12:15 Net Worth Breakdown14:18 Income and Rental Cash Flow17:39 Spending Goals and Timeline19:23 Why Spend Now22:03 401k Withdrawal Idea28:09 Elliot Runs the Numbers31:54 Lori Cash Flow Mindset33:54 Equity Return Reality Check35:08 Liquidity Options Beyond 401k36:44 Psychology Versus Math39:44 Early Withdrawal Penalty Math42:56 FI Tax Strategies 72t And Roth46:43 Opportunity Cost Of Cashing Out48:38 Option A Spend Taxable Cash49:55 Hybrid Plan And ACA Angle52:35 Replenish Reserves And Debt Aversion54:46 HELOC Bridge Versus Penalty56:18 Middle Class Trap And Money Trauma57:56 Drawdown Order And Account Strategy59:40 Margin Loans And Market Risk01:04:03 Wrap Up And Next Episode Tease
Do you have feedback or suggestions? We want to hear from you!
Contact Elliot: [email protected]
Contact Josh: [email protected]
Josh’s other podcast: Stuck In Beta
Josh’s YouTube channel: How To Fix It Workshop
Any of these products help the show. Thanks for your support!
Mint Mobile - We both use Mint Mobile and save a ton on our phone plan: https://my.mintmobile.com/refer/aEWp5rL
Empower is Josh’s choice for Net Worth and Budgeting
Wanna create a podcast? We use Descript
Looking for a new credit card? We’re big fans of Chase
Buy Us a Coffee - One time donation or monthly, it’s up to you
Want to save money on gas? Try Upside!
Books mentioned in this episode:
Come find us and subscribe on YouTube: http://www.youtube.com/@9toFI
1 hr 7 min - Continue MORNING ROUTINES in Early Retirement? | 9toFI 041
Morning Routines After FI: Slow Mornings, Habits, and StructureJosh and Elliot discuss the value of routines—especially morning routines—after retirement and in working life, sparked by Sarah sharing an Inside Out Money episode about compounding habits. Josh recounts the host’s early-retirement lack of structure and how adopting morning habits (sunlight, water, exercise) improved her feelings of laziness, prompting reflection on their own routines. Elliot describes minimal weekday routines shaped by hybrid commuting (up around 5:15–5:30 for office days; 6:30 for work-from-home) and weekends influenced by young kids, meal planning, and shared calendars. Josh outlines a long-standing 5:00 AM “slow morning” routine with water, coffee, reading/creative work, and workouts, plus consistent bedtime habits, limited news/social media, and discussion of experimenting with exercise schedules and subscription “money leaks.”
00:00 Why Routines Matter
00:17 Podcast Spark
02:10 Elliot Morning Schedule
04:54 Josh Slow Mornings
12:09 Habits And Motivation
19:05 Making Workouts Work
27:10 Evening Routine Talk
32:23 Social Media And Shopping
35:24 Streaming Subscriptions
38:41 Final Routine Takeaways
Do you have feedback or suggestions? We want to hear from you!
Contact Elliot: [email protected]
Contact Josh: [email protected]
Josh’s other podcast: Stuck In Beta
Josh’s YouTube channel: How To Fix It Workshop
Any of these products help the show. Thanks for your support!
Mint Mobile - We both use Mint Mobile and save a ton on our phone plan: https://fbuy.me/vgAmz
Empower is Josh’s choice for Net Worth and Budgeting
Wanna create a podcast? We use Descript
Looking for a new credit card? We’re big fans of Chase
Buy Us a Coffee - One time donation or monthly, it’s up to you
Want to save money on gas? Try Upside!
Books mentioned in this episode:
Come find us and subscribe on YouTube: http://www.youtube.com/@9toFI
41 min - Saying "NO" is hard | 9toFI 040
The Power of Saying No: Boundaries at Work, with Family, and with YourselfJosh and Elliot discuss how to say no to bosses, coworkers, friends, family, and oneself, reflecting on their shared people-pleasing tendencies. They open with accountability updates (Josh scheduling a colonoscopy; Elliot struggling to restart workouts after illness and foot pain), then share examples of difficulty setting boundaries, including Josh’s guilt over refusing Elliot’s brake help but spending a Sunday fixing another friend’s brakes after giving bad advice. Josh describes learning to say no at work by clarifying priorities and negotiating tradeoffs to avoid burnout, influenced by ideas like Cal Newport’s, while Elliot notes that extra effort isn’t always rewarded and emphasizes focusing on the most impactful work. They contrast work boundaries with the harder emotional challenge of saying no to friends and family, discuss regret and FOMO, and address saying no to oneself by limiting new projects, side hustles, and time commitments in early retirement.
00:00 Why Saying No Matters
01:14 Accountability Buddy Check In
03:59 The Brake Job Karma Story
06:28 Saying No at Work
11:15 Quality Over Quantity
15:53 COVID Era Boundaries
19:05 Declining the Return Invite
21:35 Friends Family Guilt
23:04 People Pleaser Guilt
24:06 Hell Yes Philosophy
25:28 Saying Yes Then Regret
27:02 Retirement Boundaries
28:28 Fence Favor Fallout
31:38 No To Yourself
32:35 Side Hustle Temptations
35:39 Time Value Debate
37:57 Babysitter Rate Reality
39:07 Practicing Better Nos
41:16 Closing And Feedback
Do you have feedback or suggestions? We want to hear from you!
Contact Elliot: [email protected]
Contact Josh: [email protected]
Josh’s other podcast: Stuck In Beta
Josh’s YouTube channel: How To Fix It Workshop
Any of these products help the show. Thanks for your support!
Mint Mobile - We both use Mint Mobile and save a ton on our phone plan: https://fbuy.me/vgAmz
Empower is Josh’s choice for Net Worth and Budgeting
Wanna create a podcast? We use Descript
Looking for a new credit card? We’re big fans of Chase
Buy Us a Coffee - One time donation or monthly, it’s up to you
Want to save money on gas? Try Upside!
Books mentioned in this episode:
Come find us and subscribe on YouTube: http://www.youtube.com/@9toFI
42 min
About 9 to FI - Financial Independence Conversations
From the publisher's feed
9 to FI is a Financial Independence podcast hosted by Elliot and Josh from St. Louis. Together, we share honest commentary on our journey to FI—covering wins, challenges, and lessons learned along the…
way. With real conversations and practical insights, we aim to help others navigate the same path, taking Financial Independence from dream to reality.