
5 Big-Picture Questions to Help High-Net-Worth Families Tackle Complex Financial Challenges
Life comes at you fast, especially when you’re responsible for managing significant wealth. Whether you're running a business, preparing for retirement, or thinking through your family legacy, you’re likely juggling a mix of financial decisions that feel anything but straightforward.
When things get complex, the instinct is often to act quickly. But reacting without the full picture can lead to unintended consequences. Instead of jumping to a solution, it can be far more effective to pause and reframe the problem.
Here are five key questions we encourage our clients to ask when navigating uncertainty. They're designed to shift the conversation from reactive to intentional—and to help you make decisions that support your long-term vision.
1. What could derail my financial future?
Understanding risk is one of the most overlooked steps in protecting wealth. The biggest risks we see for high-net-worth families often include:
- Tax policy changes
- Market volatility
- Illiquid assets or concentrated holdings
- Cybersecurity breaches
- Family dynamics (especially around inheritance or business succession)
Identifying and naming those risks is the first step toward building a strategy that absorbs shocks instead of succumbing to them.
2. Am I prepared for change?
The rules of the game are constantly shifting—especially when it comes to taxes and the economy. Whether it’s the sunset of the Tax Cuts and Jobs Act, changing estate tax thresholds, or higher interest rates, adaptability matters.
Ask yourself:
- How would a shift in tax policy affect my estate or investment strategy?
- Am I diversified enough to weather market swings?
- Do I have advisors who are proactively monitoring these changes for me?
Planning ahead means staying a few moves ahead.
3. Do I have my financial house in order?
It’s one thing to build wealth. It’s another to organize and protect it.
Make sure you can answer:
- Are my key documents (wills, trusts, insurance, tax records) up to date and easily accessible?
- Do I know where everything is stored—physically and digitally?
- Who else knows how to access important accounts or information if something happens to me?
Organization is peace of mind, not just for you but for your loved ones too.
4. What do I want my wealth to stand for?
Legacy planning isn’t just about estate taxes or legal documents. It’s about articulating your values.
Consider:
- How do I want my wealth to support my family, community, or causes I care about?
- Are the right people in place to carry out my vision?
- Am I having the right conversations now—before decisions become urgent?
We believe the most successful legacies are the ones planned with intention.
5. When was the last time I zoomed out?
Your financial world isn’t static. What made sense three years ago might not serve you today.
That’s why we encourage clients to:
- Revisit their goals and strategies at least annually
- Make updates after major life or business changes
- Use their financial plan as a living document, not a one-time project
Success isn’t about having all the answers today. It’s about consistently asking the right questions.
At Totemic Wealth & Planning, we help our clients create clarity in complexity. By grounding your decisions in purpose and process, we empower you to move forward with confidence—no matter how uncertain the landscape feels.
Ready to have a different kind of financial conversation? Let's talk.
Sources
- Harvard Business Review, 2024 [URL: https://hbr.org/2024/01/to-solve-a-tough-problem-reframe-it]
This content is developed from sources believed to be providing accurate information. The information provided is not written or intended as tax or legal advice and may not be relied on for purposes of avoiding any Federal tax penalties. Individuals are encouraged to seek advice from their own tax or legal counsel. Individuals involved in the estate planning process should work with an estate planning team, including their own personal legal or tax counsel. Neither the information presented nor any opinion expressed constitutes a representation by us of a specific investment or the purchase or sale of any securities. Asset allocation and diversification do not ensure a profit or protect against loss in declining markets. This material was developed and produced by Advisor Websites to provide information on a topic that may be of interest. Copyright 2025 Advisor Websites.