Dinner in my house is often from the kitchen’s massive island, savoring the western view of the Santa Ana Mountains. In the winter, at least. In the summer, the sun hasn’t yet set so the shades are usually closed. But when the daylight shortens, and the sun is setting early enough, we get some spectacular dinner-time sunsets.
In Southern California, winter is the “rainy season” and that means there are clouds. Anyone who’s ever played the cloud-watching game knows that they are in constant states of change and what might appear to exist one instant is gone or transformed in moments. And when the sun sets, the sky darkens, unless there’s a full moon to continue the game.
The next morning brings a new opportunity, and with it the chances for more cloud-gazing. Or not.
In my effort to make something productive of the image captured on my iPhone while fueling my old body with a BLT and sweet potato fries, I’m drawn to the ever-changing nature of our industry and the lives of those we serve. No two weeks are alike. No two clients face the same challenges. This past week was a perfect example.
First, it marks the beginning of our semi-annual investment colloquium and summit. We do a deep dive into our asset allocation models, the economic and market situations, and evaluate new investment ideas. But interacting with clients is always the primary function, and personally, the past week saw a huge dispersion of topics.
For the first time in my 30+ years in this industry, a fund company’s remediation solution—sending tangible checks directly to our clients—created untold confusion. We didn’t hear about this until after clients started calling, and by then, others had used their phones to deposit them into their bank accounts. Unfortunately, most of these checks were payable to their IRA custodian and the banks should not accept them.
Lots of clients saw the benefits of topping out their current tax-bracket bucket last year with Roth conversions. One had an unusually large one-time tax deduction in 2025. However, he missed his 457-plan sponsor’s internal conversion year-end deadline, so we helped him engineer an indirect Roth conversion. He took the distribution before year-end and must redeposit the funds within 60 days of that distribution.
An aging client has decided it is time to move out of her paid-off single-family home and into a senior living facility so that she’ll have more social interactions and fewer annoying maintenance problems at the old house. She’s got to decide about turning it into a rental or creating liquidity to help fund her decision. We’ll discuss the financial aspects with her and the estate planning attorney next month.
A mid-career project manager just got a severance package and is frantically looking for another position. Their kids are grown, the spouse works retail, and while mom’s health is declining, they’re trying to get her affairs in order. We’ve discussed healthcare, liquidity, rightsizing, mom’s situation, and the job hunt.
A couple in their 60s contemplates claiming Social Security. They expect to live long lives—both are very active and medically attentive. We’ll model their claiming options while determining how they align with their goals. The difference between claiming at 62 versus 70 could be worth hundreds of thousands of dollars in lifetime benefits for this couple.
A long-term client contemplates retirement and needs projections evaluating pension options, plus Social Security and significant 401(k), IRA, taxable accounts and some rental properties. Planning a 30-year life after a successful aerospace engineering career is about more than the numbers. He’s doing some things that I’d like to do but won’t prioritize in my own life. So, I get a vicarious experience through him!
A senior client recently began taking random, excessively large, and uncharacteristic distributions. After investigating, I’ve filed a report with our Senior Investor Protection team to help protect this widow’s money from a highly manipulative con artist. There are limits to our resources, but it’s good that the industry is finally taking some action. My first published trade industry article titled “Disrespecting our Elders” prepared me to recognize the signs of elder abuse.
Finally, a business owner is working through the sale of his business and we’re modeling his family’s future sources of income. After 30 years building something from nothing, he’s ready for the next chapter—but the tax implications and income structuring are complex.
That’s this week.
Next week it’ll be a different set of issues, challenges, and opportunities. Watch our blog as I dive deeper into several of these situations—the mechanics of Social Security claiming strategies when you expect to live to 90, the financial considerations when aging parents need to move, navigating a mid-career layoff, protecting vulnerable adults from financial exploitation. But I wanted you to see what comprehensive planning actually looks like. It’s not just investment management or tax planning or retirement projections. It’s all of it, customized to where each client is in their life.
Tomorrow brings new challenges, new opportunities, and new cloud formations. That’s what makes this work compelling—and what makes comprehensive planning essential. You can’t predict what situations you’ll face, but you can have a guide who’s seen enough sunsets to know what’s coming.
Now it’s time to do the dishes.
Research and development of this article included the use of artificial intelligence tools.
Categories: Featured – Blog, Client Stories, Financial Plan, Retirement, Lifestyle
The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual.
Traditional IRA account owners have considerations to make before performing a Roth IRA conversion. These primarily include income tax consequences on the converted amount in the year of conversion, withdrawal limitations from a Roth IRA, and income limitations for future contributions to a Roth IRA. In addition, if you are required to take a required minimum distribution (RMD) in the year you convert, you must do so before converting to a Roth IRA.