🙌 50 Actionable Lessons to Upgrade Your Travel, Finances, Relationships & More

After 230 episodes, here are the 50 most actionable strategies I’ve learned, tested, and used to optimize travel, money, productivity, investing, relationships, and more. These aren’t just generic tips—they're the exact mindsets, tools, and tactics I use every day to get more from life without spending more time or money than necessary. You can also listen to Ep #231 if you prefer the audio format. 

🛬 Travel Hacks: Maximize Savings & Your Adventures

💳 Leveraging Points & Miles

1. Welcome Bonuses Always Win: While it's fun to optimize for categories like dining, the most important thing to remember is that welcome bonuses on new cards often yield around 17x points on your initial spend, far outperforming category bonuses. More on Ep #170.

2. Play the Points Game with Others: You can multiply your earnings by involving your spouse, partner, parents, family, or friends. Not only can everyone earn welcome bonuses, but you often get referral bonuses too, turning 1+1 into much more than 2. More on Ep #221.

3. Be the Group Travel Agent: Offer to book hotels and flights for group trips (family, friends, reunions, work events) on your card. Most people hate the logistical work, and you can accumulate a ton of points by having them Venmo/Zelle you the cost.

4. Leverage Award Search Tools & Alerts: These tools have gotten incredibly good at helping you maximize your points and find outsized value for flights. Use them not only to search but also to set alerts for better prices or routes so you can rebook. More on Ep #166 and #167.

5. Buy Points When They're on Sale: Even if you don't have enough points for a great deal, points often go on sale (e.g., Hilton points 6-12 times a year, Avianca LifeMiles frequently). You can buy points at a discount and immediately book incredible value redemptions, like a $3,000/night hotel for $600 worth of purchased points. 

6. Explore Hidden Credit Card Benefits: Download your card's guide to benefits and check your card issuer's website (Visa Infinite, MasterCard World Elite). You'll be amazed at the purchase and travel protections, and other crazy perks you might be missing. More on Ep #113.

7. Military Fee Waivers: If you're active duty military or a spouse (sometimes including reserves), you can get most credit card annual fees completely waived. This can save thousands of dollars and unlock benefits like free nights, hotel credits, Priority Pass, Global Entry, and Clear.

🧳 General Travel Tips

8. Don’t Let the Trip Plan You: Be conscious of whether you're intentionally planning the trip you want, or if you're letting a deal or opportunity dictate your entire itinerary. It's okay to build a trip around a deal, but make sure it aligns with your desired experience. More on Ep #187.

9. Reverse Image Search Vacation Rentals: For Airbnb or VRBO listings, use Google image search or a tool like Hichee.com to find if the property is listed elsewhere, potentially for a lower price and with fewer fees.

10. Monitor for Price Drops Post-Booking: Use tools like Google Flights alerts, AutoSlash (for rental cars), HotelSlash (for hotels), Autopilot (for flights that rebook for you), or TripIt to track price drops on your booked travel. You can often rebook and get credits or refunds.

11. Email the Hotel Before Your Stay: Book directly with the hotel and send a friendly email introducing yourself, mentioning if you're celebrating something, etc. Hotels are in the hospitality game and often respond with upgrades, perks, or special touches.

12. Use eSIMs for International Data: Ditch expensive roaming plans. eSIMs (like Airalo) make it incredibly easy and cheap to get high-speed international data without finding a local SIM card.

13. Take Free Walking Tours: These are an incredible, low-cost way to get oriented in a new city, learn about the culture, and get local recommendations. Remember to tip your guide, as that's how they earn their living.

14. Apply the Peak End Rule: When planning a trip, remember that you'll primarily remember the highlight and the very end of the trip. Try to save something special for the end to create a lasting positive memory. More on Ep #5.

💸 Money Hacks: Earn More, Save More, Invest Better

🧾 Navigating Expenses

15. Audit and Slash Your Bills Regularly: Regularly review and reprice your recurring bills, especially insurance policies (auto, home/renters, umbrella, life, disability, pet, and travel). This often leads to finding comparable or better services for less money. More on Ep #104 and #34.

16. House Hack: Find creative ways to offset your largest expense – housing. Whether you rent or own, you can rent out a spare room, a separate unit, or even consider multi-unit properties to significantly subsidize costs. More on Ep #14.

17. Optimize Your Energy Plan: Check with your state, county, and utility company for different energy plans. Depending on your usage (especially with an EV), you could get wildly different bills. Also, make your home more energy-efficient. More on Ep #135.

18. Adopt a "Die with Zero" Mindset: Focus on net fulfillment > net worth. Recognize that there are seasons in life where spending on experiences (especially those with a physical component, like hiking Kilimanjaro) makes more sense than continuously saving. Don't defer all your dreams to retirement if you might not be able to do them later. More on Ep #91.

19. Establish Money Rules: Create clear rules, ideally with your partner, to streamline financial decision-making. For example, "never question spending money on books" or "fly business class on overnight international flights using points." This removes friction and makes spending aligned with your values. More on Ep #9 and #112.

20. Negotiate (Almost) Everything: Don't be afraid to ask! This applies to salaries, Airbnb rentals (especially for longer stays or filling gaps in calendars), online purchases (ask live chat for promotions), and even appealing your home's valuation for property taxes (one listener lowered theirs by 25%). More Ep #19.

21. Monitor Online Price Trends: Before buying something online, use browser extensions like Keepa to see the historical price graph. This helps you avoid overpaying and wait for potential sales.

22. Always Stack Deals: For major purchases, layer on as many savings as possible: coupons, shopping portals, card-linked offers, discounted gift cards, and credit card points. You can save a significant percentage by combining these methods.

23. Install Browser Extensions for Shopping: Use extensions like Rakuten (for cash back/points) and CardPointers (to automatically activate card-linked offers and tell you which card to use) to ensure you're always getting a deal, even if it's just a small amount.

24. Leverage Gift Cards for Savings: Buy gift cards at a discount or earn bonus points when purchasing them at specific stores (like office supply or grocery stores). Use them for everyday purchases to save money. Just be mindful not to use them for items where you want credit card benefits like extended warranty. More on Ep #212.

25. Access Library Books Online: Use browser extensions and apps like Libby to check out ebooks and audiobooks for free from your local library, saving you money on book purchases.

26. Don't Forget to Grab Freebies at Hotels: Many hotels offer free bottled water and sometimes even fresh fruit in their gyms. Don't be shy about taking advantage of these amenities, even if you're not working out.

27. Consider a CPA for Complex Taxes: If your tax situation is complicated, hiring a proactive CPA can often save you more money on your overall tax bill than you'd save by doing it yourself with software. They can help you optimize deductions and strategies. More on Ep #147.

💰 Managing Investments & Income

28. Automate Everything: Set up recurring investments, savings, and use robo-advisors to automatically rebalance your portfolio and perform tax-loss harvesting. The less you have to think about your finances, the better.

29. Passively Invest in Low-Cost Index Funds: Instead of trying to time the market or pick stocks, build a diversified portfolio that invests in low-cost index funds. This strategy aims for consistent growth and helps you achieve long-term success without constant effort. More on Ep #168.

30. Optimize Your Accounts with Tax Advantages: Prioritize investing in accounts like 401Ks (especially with employer matches), Roth IRAs (even backdoor methods if income-ineligible), and Health Savings Accounts (HSAs) for their unique tax benefits. More on Ep #144 and #50.

Donate Appreciated Stock to Charity: If you donate to charity, give highly appreciated stocks or other assets instead of cash. You get the same tax deduction, avoid capital gains taxes on the donated asset, and can then repurchase the stock at its current price, resetting your cost basis.

Maximize Your HSA: Treat your HSA as a super-powered investment account. Contribute pre-tax, let the money grow tax-free, and withdraw it tax-free for qualified medical expenses later in life. It's a triple-tax-advantaged gem.

31. Earn Interest on All Your Cash: Don't let your money sit in a low-interest checking or savings account. Seek out high-yield savings accounts, money market accounts, or short-term US Treasury ETFs that offer much higher interest rates (e.g., 4% range), especially if you're in a high-tax state for tax-advantaged treasuries. More on Ep #177.

32. Turn Deals into Side Hustles: You can earn thousands of dollars a month by strategically finding and leveraging online deals, bank bonuses, brokerage bonuses, meal kits, and gift cards. It's a non-traditional "side hustle" that can significantly boost your income. More on Ep #181.

33. Search for Unclaimed Money: Check your state's unclaimed money database (and for your family members!). Companies turn over forgotten funds (refunds, old accounts) to the state, and many people have found hundreds, even thousands, of dollars waiting for them.

34. Pay Bills with Credit Cards (Strategically): Most bills can be paid with a credit card, even if there's a fee (e.g., Plastique for mortgage/tuition). While a fee like 2.9% might not make sense for everyday spending, it absolutely does if you're trying to meet the minimum spend for a valuable welcome bonus (e.g., 17% return). Just make sure you can always pay your bill in full to avoid interest. More on Ep 226 and #227.

35. Set Up a Will/Basic Trust: If you're building wealth and have a family, set up a will or a basic revocable living trust. This ensures your assets are distributed as you intend, avoids probate, and allows you to name guardians for your children. It's simpler than you might think and can be done in hours. More on Ep #62.

💫 Life Hacks: Time, Relationships, Health & More

⌛ Optimize Your Time

36. Leverage AI for Everything: Use tools like ChatGPT, Gemini, Claude, or Perplexity. They can act like an "army of interns" for travel planning, research, drafting, summarizing, and countless other tasks, saving you immense amounts of time.

37. Do a Calendar Time Audit: Go back and look at how you actually spent your time. Color-code activities by whether they gave you energy or took energy away. This helps you identify where you might be allocating time differently than you'd want and prompts you to re-evaluate. More on Ep #99.

38. Identify Your Daily Highlight: Each morning, ask yourself: "What's the one thing I want to accomplish today? What's going to be the highlight of my day?" Writing this down helps ensure you focus on what's most important and have an awesome day. More on Ep #185.

39. Apply the "Hell Yes or No" Filter: If something isn't a "hell yes," it's a "no." This powerful filter helps you decide how to spend your time and energy, allowing you to pass on things that don't truly excite or align with you. More on Ep #109.

40. You Don't Owe a Reply to Every Email: Just because someone sends you an email doesn't mean you're obligated to respond, especially if it's not from a close relationship or your boss. Don't let your inbox control your time.

41. Outsource Things You Don't Enjoy: Identify tasks or chores you don't like or don't have time for (like meal prep, cleaning, or mowing the lawn) and find ways to outsource them. This can free up significant time and reduce stress, even if it's just for a season. More on Ep #98.

🥰 Enhance Your Relationships

42. Practice "Us Listening": Beyond listening to yourself or just the other person, strive for "us listening," where you truly understand and empathize. Sometimes the best tactic in relationships is to just stop talking and listen. More on Ep #190.

43. Adopt the "80/80 Marriage" Mindset: Instead of keeping score in your relationship (the 50/50 model), aim for both partners trying to give 80%. This shifts the focus from tracking contributions to generously supporting each other, leading to a happier relationship. More on Ep #43.

44. Host "Two-Hour Cocktail Parties": Ditch the stressful dinner parties and host shorter, simpler cocktail parties (or happy hours). Nick Gray's formula makes it easy to schedule these regularly, fostering community and building relationships, especially in new environments. More on Ep #68.

🥗 Make Healthier Choices

45. Pre-Order Your Meals (Mentally): Before going to a restaurant, look at the menu when you're not hungry and decide what healthier option you'll order. This makes it easier to stick to your healthy choice when you're at the restaurant and more tempted.

46. The "Yes in Five Minutes" Rule: If you're tempted by an unhealthy treat, give yourself permission to have it, but make yourself wait five minutes. Often, in that five-minute period, you'll get distracted or the craving will pass, preventing overindulgence. 

🔒 Boost Your Security

47. Freeze & Delete Your Personal Data: Your credit reports, "The Work Number" report (which tracks your pay stubs/salary), and other similar databases to protect your financial information. Request removal of your address, phone number, and other personal information from data brokers and real estate sites (like MLS, Redfin, Zillow) to minimize your digital footprint and reduce your target profile. Services like DeleteMe can do this for you. More on Ep #78.

48. Use Password Managers and Family Safe Words: These simple tools significantly enhance your online security and family safety.

🧠 Improve Your Decision-Making

49. Burn the Boats Mentality: To overcome fear and fully commit to a goal, adopt this mindset. By not having a "Plan B" (even if just in your mind), you fully focus on making "Plan A" successful. More on Ep #105.

50. Ask Yourself: "What Advice Would I Give a Friend?": When you're unsure what to do, stepping outside your own perspective and asking what advice you'd give a friend often provides a clearer, less over-analyzed gut reaction that's usually the right path for you too.

Editor’s Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.