Credit Card Hacking Mistakes, Annual Fee Cleanup, and Early Retirement Doubts

Josh introduces a conversation with Elliot focused on credit card hacking and, later, Elliot’s thoughts about possibly extending his early retirement timeline. They discuss a St. Louis heat wave, their current FIRE stages (Elliot nearing retirement; Josh 1.5 years into early retirement after leaving work in April 2025), and listener feedback on fear of boredom. Josh shares a cautionary tale from years of chasing sign-up bonuses and referrals, accumulating a large stack of cards, failing to close unused accounts, and wasting an estimated $1,500–$2,000 per year in annual fees; they discuss tracking tools, closing cards, and temporary credit-score impacts. Elliot describes disliking his job, weighing an extra year to meet family goals, and interviewing internally to change his situation. They also cover post-retirement guilt, Elliot’s improving foot recovery while coaching soccer, and the growth of the St. Louis ChooseFI community activities.

00:00 Episode Setup

01:11 Heat Wave Catch Up

02:26 Where We Are Now

04:29 Boredom Before Retirement

07:09 Credit Card Hacking Pitfalls

12:13 Tracking Cards and Fees

15:00 The Stack of Cards

19:25 Elliot Weighs One More Year

24:46 Life After Retiring Feelings

33:00 Getting Active Again

35:20 ChooseFI Community Hikes

37:34 Thanks and Wrap Up

Do you have feedback or suggestions? We want to hear from you!

Contact Elliot: Elliot@ninetofipod.com

Contact Josh: Josh@ninetofipod.com

Josh’s other podcast: Stuck In Beta

Josh’s YouTube channel: How To Fix It Workshop

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Books mentioned in this episode:

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Spending on Convenience, Rental Deadlines, and a New Weekly Planning System

Josh and Elliott catch up after a short break and note that releasing episodes every other week has coincided with a spike in views, listens, and listener feedback. They revisit their “spending on convenience” challenge: Elliott tried Aldi curbside grocery pickup and found it saved weekend time, while Josh sought quotes to outsource drywall and painting on a vacant rental but declined after receiving a nearly $7,000 estimate and deciding the money was better reserved for repairs he can’t do himself. Josh shares reframing the frustration of house projects, dropping self-imposed rental deadlines, and creating a “rental real estate investor policy” with notes per property to guide decisions when vacancies occur. He also explains restructuring his weekly planner by moving non-urgent tasks into categorized electronic lists reviewed monthly, reducing stress and perceived busyness. Elliott discusses current life stress, a failing water heater, and getting a new puppy, which led to canceling an October trip.

00:00 Catch Up and Feedback

01:54 Convenience Spending Check In

02:34 Grocery Pickup Experiment

03:27 Rental Rehab Quote Shock

07:33 Time vs Money Mindset

09:58 Rental Deadlines and Policy

13:54 Weekly Planner Overhaul

21:44 Feeling Less Busy Lately

23:51 Elliotts New Puppy Update

26:18 Wrap Up and Thanks

Do you have feedback or suggestions? We want to hear from you!

Contact Elliot: Elliot@ninetofipod.com

Contact Josh: Josh@ninetofipod.com

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

Elliot’s Pre-Retirement Fears: Boredom, the Big Shovel, and Trusting the FI Math

Josh and Elliot decide to continue the podcast after receiving encouraging listener feedback and invite more comments via email and Spotify. They focus on Elliot’s approaching planned exit from his W-2 job after March 1, 2027, timed to a mid-February bonus and RSUs vesting March 1, while noting he may pivot if circumstances change. Elliot describes an “existential” unease about early retirement, mainly fear of boredom and fear of giving up a lucrative “big shovel,” especially with three elementary-aged kids and future education costs. They discuss how FI “only solves money problems,” the mindset challenge of trusting the math versus analysis paralysis, and how surrounding influences can amplify worries. Elliot feels excitement and terror about owning his time but believes he could earn money again if needed, likely outside corporate work. They agree to revisit additional fears and later discuss drawdown strategy.

00:00 Welcome and Feedback

01:19 Elliot Retirement Setup

03:12 Target Date and Work Factors

06:08 Josh Retirement Lessons

07:32 Elliot Fears Boredom

09:45 Doubt and FI Mindset

12:16 Thought Experiment Without FI

16:42 Social Circle and Life Stage

20:38 Fear of Unknown Time

23:57 Contingency Plans and Barista FI

27:52 Mindset Shift After FI

29:05 Wrap Up and Next Episode

Do you have feedback or suggestions? We want to hear from you!

Contact Elliot: Elliot@ninetofipod.com

Contact Josh: Josh@ninetofipod.com

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