December 4, 2025
Even at the highest levels of success, the most important questions are rarely financial. They’re personal. They’re generational. They’re about what gives your life meaning and how your choices shape who you are and the people you love most.
Even at the highest levels of success, the most important questions are rarely financial.
They’re personal. They’re generational. They’re about what gives your life meaning and how your choices shape who you are and the people you love most.
These 10 questions are designed to help you pause, reflect, and think about what matters most as we head into the new year.
1. What does “success” mean to me now and has that definition evolved as my life has evolved?
2. What experiences make me feel most alive, curious, or inspired?
3. Who challenges my thinking, broadens my perspective, and helps me grow?
4. How am I investing in my family’s emotional, spiritual, and intellectual capital not just our financial capital?
5. What do I want the next decade of my life to feel like, not just look like?
6. Which values do I want my children to inherit, and am I modeling them clearly enough?
7. Where am I craving deeper purpose, connection, or meaning?
8. Which relationships energize me, and which ones quietly drain me?
9. How do I want to be remembered by the people who matter most?
10. What bold step have I been postponing and what would happen if I took it now?
These questions don't need perfect answers—they're starting points for deeper conversations with yourself and the people who matter most.
Consider tackling one question at a time over the coming weeks or discuss them with friends and family who understand the unique challenges and opportunities that come with significant wealth.
Disclosure: R360 is not an investment adviser. Information provided within is for educational purposes only and should not be construed, nor is intended to be, investment advice or a recommendation to invest in any types of securities. R360’s views are subject to change at any point without notice. No investment decision should be made based solely on the content herein and only a financial professional should be engaged for providing investment advice and recommendations. Past performance is not an indication of future returns.
