Lessons Learned in 40 years, Ep #86

Upthinking Finance™ is now trademarked

This episode is my reflection on nearly four decades in the financial services industry. I want to share some of the most important lessons I’ve learned—from portfolio management missteps and tax planning pitfalls, to the value of flexibility, liquidity, and real client relationships. Over the past four decades, the financial industry has evolved enormously, and these days, experience and adaptability matter when you’re building a practice rooted in trust and personal connection may outshine growth-at-all-costs strategies.

You will want to hear this episode if you are interested in...

05:08 Reallocating investments to manage risk07:47 Understanding alternative investments risks12:10 Embracing trend following strategies13:47 Discovering niche management firms22:49 Discussing real-life financial planning25:28 Working with outside consultants28:43 Navigating financial crises together32:08 Connecting with industry influencers36:51 Investment strategies and risks

The Perils of Letting Taxes Guide Every Decision

Tax efficiency matters in any sound financial plan, but letting tax consequences drive every decision can backfire. Complex strategies like irrevocable life insurance trusts (ILITs) and Roth IRA conversions, which, while once advantageous, have later become obsolete or even detrimental due to shifting laws or unforeseeable changes.

Overemphasis on avoiding taxes—such as refusing to rebalance a portfolio for fear of triggering capital gains—can leave clients worse off if market conditions change unexpectedly. Prioritize flexibility and liquidity over the lure of perfect tax avoidance. Sometimes, a slightly higher tax bill is a small price to pay for maintaining the ability to adapt to life’s unpredictables.

The Cost of Inflexible Investments

Locking up assets in illiquid programs—such as certain private credit products or non-listed REITs—may offer the promise of higher returns or tax benefits, but they come at the cost of flexibility when life throws a curveball. Divorce, illness, or sudden opportunities can necessitate access to funds that are tied up, sometimes indefinitely. Thus, every investment should be scrutinized not just for its upside, but for the accessibility of capital when it's truly needed.

Personalization Over Commodity

The financial advice industry has trended towards commoditization, driven by “best practices” that prioritize scalability and efficiency—sometimes at the expense of individual cl