25 Questions From 2025

Many people think wealth managers spend their days picking stocks and watching the market. That is part of the job, but it is not the part that matters most. The conversations that really move the needle rarely begin with “What should we buy?” They usually begin with “What should we do?” The biggest financial decisions are not just about investments. They are connected to your career, your family, your goals, and the tradeoffs that come with each stage of life. Those decisions shape outcomes far more than any single holding in a portfolio. Real wealth management is about helping families think clearly, plan with intention, and make smart, coordinated choices across their entire financial lives. 

Below are real questions that we received in 2025:

  1. We are inheriting money that we do not need, what should we do with it?

  2. How do I structure my portfolio to minimize taxes over time?

  3. What would it look like if we bought a second home?

  4. I need to borrow money, can I use my investments as collateral?

  5. How much would we save if we moved to a state with lower income taxes?

  6. I don’t need any income, what should I do with the RMD’s?

  7. How much can I put down to start this business with a friend? Should I do it?

  8. I am paid via W-2, is there anything we can do to lower my tax burden?

  9. My business is doing well, what should I do with the cash?

  10. Are we making a mistake giving up our 2.5% mortgage?

  11. Can I fund my backdoor Roth for this year and last year?

  12. Do I need long-term care coverage?

  13. What is the best way to give to charity?

  14. I’m retiring this year. How will retirement work logistically?

  15. What’s the best way to put money aside for our kids?

  16. Should we keep our old house as a rental?

  17. I’m leaving the corporate world, what do I need to think about?

  18. Should I leave my business to my kids or sell it?

  19. As a 1099, how can I save for retirement?

  20. I turn 65 this year, how do I enroll in medicare?

  21. When should I take social security?

  22. I’ve been granted more company stock, what should I do with it?

  23. I have another liquidity event in the next 5 years. What should I be doing now to prepare?

  24. Is my family covered if something happens to me?

  25. Are our estate documents aligned with how our assets are titled?

If any of these questions resonate with you, feel free to schedule a quick call here.

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What HENRYs, Business Owners and Near Retirees Have in Common (And Why it Matters More Than You Think)