Rich Habits Podcast – Q&A: Feeling Behind on Life Goals, Work Bonuses, & Medical Challenges

Hosts: Austin Hankwitz & Robert Croak
Date: February 19, 2026

Episode Overview

This episode of the Rich Habits Podcast features a Q&A format, with Austin and Robert tackling seven listener questions covering urgent financial hardships, investing windfalls, handling work bonuses, navigating real estate dilemmas, starting over in the workforce, optimizing 401k allocations, and strategically managing loan repayments. Designed to provide practical blueprints rooted in experience and empathy, the hosts deliver honest, actionable advice for those pursuing financial stability and wealth-building—whether they’re just getting started or already making strides.

Key Discussion Points & Insights

1. Recovering from Medical & Financial Hardship (Jessica K.)

[01:51 – 11:21]

• Situation: Jessica’s family faces severe financial and health challenges: her husband’s disabilities prevent consistent work, they have no savings but expect a good tax refund, and are living off-grid with relatives to pay down debt.
• Austin’s Blueprint:
  • Emergency Fund First: “The first thing I would do is I would create a little bit of buffer between you and life…$1,000, 2,000, …maybe $5,000 sitting in a high yield savings account.” [03:12]
  • Budget Ruthlessly: “Audit your spend…audit your bank accounts, audit your credit cards. Any Netflix, any…at T95 bucks? Heck no. See you later.” [04:45]
  • Three to Six Months’ Expenses: “You need to have three to six months of expenses in an emergency fund sitting for you, because disaster is going to strike again.” [06:04]
  • Husband’s Work Options: “Perhaps there’s a world where he can start doing some sort of customer support job with call center stuff or maybe something on his computer…” [07:33]
  • Leverage AI for Job Solutions: “Go to Gemini, chatgpt, Claude, whatever and just do a ton of homework to find what is best for your situation.” [11:21]
• Robert’s Perspective:
  • Mindset Matters: “I know your mindset is in the right place. You had all the buzzwords and all the things. …You are ready to fix this problem and do whatever you need to do.” [09:39]
  • Prioritize Income, Not Reinvention: “I would not worry about your husband reinventing himself…get a job, any job.” [09:58]
  • Consider Your Roles: Suggests potentially Jessica works a second job while her husband stays home if feasible.
  • Summing Up: “Get the budget in order, get the additional revenue up and running, start saving toward the future.” [11:04]

2. Investing a $65,000 Settlement at Age 25 (Ben B.)

[13:11 – 16:43]

• Situation: Ben, injured in an accident, receives a $65,000 settlement and wants to invest for maximum long-term returns.
• Robert’s Advice:
  • Let Compound Interest Work: “Put this money away, get it somewhere safe. Let compound interest work its magic.” [14:08]
  • Pretend You Never Got the Lump Sum: “Try to pretend you didn’t get it because if you start spending it, it’s hard to stop.” [15:26]
• Austin’s Math:
  • Illustrative Returns: “If you had that 65,000 [and] invested all…you’re looking at $2.2 million over a 40 year period of time…adjusted for inflation.” [15:48]

3. Maximizing a Work Bonus: Splitting Fun & Future (T.)

[17:08 – 21:17]

• Situation: T receives a $30,000 annual bonus and is weighing how to split it between fun, savings, and investments.
• Austin’s Framework:
  • Emergency Fund Comes First: “If your emergency fund…is already fully funded…there is no reason to add more money to it.” [17:51]
  • Celebration is Earned: “I would probably spend several thousand of it enjoying my life. You’ve done a great job so far.” [18:45]
• Robert’s Rule:
  • 10-20% for Fun: “My general rule of thumb is 10 to 20% is fun, vacation, upgrade the car, whatever it is…and the rest gets invested.” [19:44]
• Budget System Takeaway:
  • Live Like the Bonus Doesn’t Exist: “All of your monthly expenses are in this normal, you know, your salary…when you get the extra 30…it’s free money essentially.” [20:36]

4. Real Estate Crossroads: Raise Rents or Sell? (Raul P.)

[22:00 – 25:44]

• Situation: Raul owns a rental below market rate. His wife wants to sell for $100k equity; he’s hesitating, considering raising rent instead.
• Robert’s Input:
  • Leaning Toward Selling: “I would probably sell the property…allows him to probably outperform the rental and the growth…of the property.” [22:49]
  • Pitfalls of Raising Rent: “You might lose that tenant and you might spend months and months getting a new one…make sure when you’re basing your rent increase…they are equal comps.” [23:46]
  • Cash Flow Warning: “If you go 3, 4, 5 months without any income…that could set you back two years in cash flow.” [25:23]
• Austin’s Reminder:
  • Tax Implications: “First thing you want to do is…spend some time here talking about the tax implications of this gain.” [25:44]

5. Returning to the Workforce Remotely at 56 (Lily)

[26:35 – 31:22]

• Situation: Lily, 56, is looking to reenter the workforce ideally in a remote capacity.
• Austin’s Suggestions:
  • Leverage Experience or Certify in a New Skill: “Figure out a type of career that aligns with your existing work experience…or something you can get certified in.” [28:26]
  • Medical Coding as a Case Study: Offers example of his mother becoming a medical coder after a long work hiatus.
  • Remote Is Competitive & Tech-Heavy: “Remote aspect…I’d argue, has gotten really competitive…these types of companies are like tech startups that will hire you, but they expect you to like, understand tech really well.” [27:12]
• Robert’s AI Angle:
  • Let AI Help You Discover Job Paths: “Go to ChatGPT or Gemini…Given this skill set, what would be…give me 10 options that are best for me.” [29:51]
  • Local Creative Alternatives: If not tech savvy, try local networks, law offices, clerical work, or Facebook groups.
• Cost-Benefit of Retraining:
  • “If you are going to go get a certification…make sure there’s a clear ROI on that investment.” [31:22]

6. Best Split for 401k Matching: Pre-tax vs. Roth (Dante)

[32:28 – 35:20]

• Situation: Dante, 23, just started a job with a generous 10% 401k match; weighing pre-tax vs. Roth contributions.
• Austin’s Position:
  • Always Elect Roth If Possible: “I always elect for the Roth variant…I do not know what the tax law is going to be in 20, 30, 40 years from now…” [34:16]
• Robert’s Confirmation:
  • “The Roth…is one of the greatest wealth building tools known to mankind and available to everyone over 18.” [35:00]

7. Paying Off Debt with 401k Loan or Cash? (Evan)

[35:20 – 39:18]

• Situation: Evan is considering taking a new, larger 401k loan to pay off current higher-interest debt and set up an emergency fund.
• Austin’s Strategic Rethink:
  • Don’t Replace One Loan with Another: “It sounds to me like you’re trying to…what’s the phrase, Robert?”
  • Robert responds: “Rob Peter to pay Paul?” [36:25]
  • Austin’s Prescription: “Just pay off the 401k loan with your bridge account and a little bit from your high yield savings. Don’t go more into debt.” [37:55]
• Robert’s Closer:
  • “Robbing Peter to pay Paul never works…Do what Austin said, get free and clear of the high interest debt.” [38:20]

Notable Quotes & Memorable Moments

• Austin on starting from near-zero:
  “Something that we really strive to do with the show is give people hope. And Jessica, Robert and I are gonna do our best to give you hope. And, and that hope is going to come in the form of a blueprint…” [02:46]
• Robert on forward motion:
  “Get the budget in order, get the additional revenue up and running, start saving towards the future, and I think you guys will be able to figure this all out.” [11:04]
• Austin’s lump sum investing math:
  “You’re looking at $2.2 million over a 40 year period of time…adjusted for inflation…from a $65,000 settlement.” [15:48]
• Robert’s bonus-grounding rule:
  “If you get a lump sum, try to pretend you didn’t get it…because if you start spending it, it’s hard to stop.” [15:26]
• On real estate decision making:
  “If you go three, four, five months without any income on that property, that could set you back two years in cash flow.” [25:23]
• Austin on the Roth advantage:
  “If I can make sure that my money is going to grow tax free in retirement via the Roth retirement account…I'm going to choose that every single time.” [34:16]
• Robert, succinctly:
  “Robbing Peter to pay Paul never works.” [38:20]

Timestamps for Major Questions

• Medical/Financial Hardship Blueprint (Jessica): [01:51 – 11:21]
• Investing a Settlement Lump Sum (Ben): [13:11 – 16:43]
• Splitting a Bonus for Fun vs. Future (T.): [17:08 – 21:17]
• Real Estate: Raise Rent or Sell? (Raul): [22:00 – 25:44]
• Re-entering Workforce Over 50 (Lily): [26:35 – 31:22]
• 401k Pre-tax vs. Roth Split (Dante): [32:28 – 35:20]
• 401k Loan and Debt Strategy (Evan): [35:20 – 39:18]

Takeaways & Tone

• The tone is pragmatic but warm, mixing real-life experience with direct, actionable steps—whether listeners are climbing out of dire circumstances or fine-tuning a healthy financial plan.
• Both hosts stress the importance of budgeting, emergency savings, not over-leveraging, and letting time/compound interest work for long-term wealth.
• They repeatedly encourage listeners to celebrate wins, leverage technology (especially AI tools), and align decisions with both current needs and big-picture goals.
• Listeners at all stages—starting from scratch, managing windfalls, or optimizing ongoing investment—receive affirming, step-by-step guidance.

For Listeners Who Missed This Episode

This episode is a masterclass in financial triage and wealth building—packed with empathy, practical roadmaps for tricky situations, and clear frameworks to help you keep moving forward. Wherever you are in your journey, there’s something here to help you build your “rich habits,” one smart, hope-filled step at a time.