Dr. Preston Cherry, CFP
Flat‑fee fiduciary advisor and financial‑well‑being researcher; investing, retirement income, and plan‑life alignment.
Avoidance Costs More Than Effort; Seek Alignment
Avoidance is expensive. Not immediately—but over time. You can keep earning, investing, and moving forward and still feel unclear, because the issue isn’t effort. It’s alignment. Wrote about where that changes.
Stop Avoiding: True Clarity Begins with Facing Reality
Avoidance doesn’t look like failure. It looks like progress that doesn’t feel right. Clarity starts when you stop avoiding where you are.
Tax‑aware Timing Crucial when Bonus and Equity Vest Together
Stack a big bonus + equity vest in the same year and watch how fast taxes eat into decisions you didn’t plan. Most people aren't just asking about returns, they are asking about better tax-aware timing.
High Earners Need Coordinated Advanced Financial Planning
April is Financial Literacy Month Most high-income earners feel financial literacy isn't for them because it's too basic. You are right. You are past the fundamentals. Your financial confidence in topic areas, decisions, coordination, and executions are just different now. Retirement. Taxes....
Invest for Life Alignment, Not Market Beats
A mistake I see often with high-income professionals: “Am I beating the market?” It sounds like the right question. It’s not. I was recently featured in TheStreet Pro discussing what actually drives an investment strategy. Alignment. It’s not about chasing returns. It’s about structuring your portfolio...
Earn More, Spend Intentionally to Avoid Lifestyle Drift
A big income jump doesn’t automatically create financial progress. One person I spoke with is jumping from six to seven figures in one year. Lifestyle should grow as your life grows. But it should be intentional. Without a plan, spending quietly expands alongside...
Prioritize Living over Maximizing Every Tax Deduction
Optimize vs. Maximize You don’t need to win every tax year. You need to win the life you’re living. Chasing every deduction. Timing every Roth conversion. Micromanaging every IRMAA bracket. At some point, maximizing starts competing with living well. That’s when strategy needs recalibration.
Financial Harmony Aligns Personal Finance for Family Unity
Financial Harmony™ integrates accumulation, disciplined strategy, and intentional deployment to create your Return on Alignment™. It begins with the individual. It scales to the household. It strengthens relational unity.
Trust Drives Markets: When It Falters, Risk Rises
Trust is emotional. It’s also economic infrastructure. When it weakens, markets reprice risk and retirement plans built on stability require harder tradeoffs. Most people treat trust as sentiment. It isn’t. It determines how money moves. I sat down with George D. Kinder to...
Stop Maximizing, Start Optimizing for Sustainable Success
High achievers rarely struggle with discipline. They struggle with knowing when to stop maximizing. Trying to win every financial decision can quietly erode both wealth and well-being. For two years, our savings rate dropped to 5%. We were building a marriage across two countries. No...
