FINANCIaL
FIELd NOTES
The Future of Social Security (2026 edition)
Will there be anything left when I retire? Will my benefits get cut? These are some of the most frequent questions I get when it comes to someone’s retirement plan. And the media loves to talk about the Social Security problems.
Fortunately, there is data to answer these questions. Every year the Board of Trustees for Social Security reviews the financial status of the trust fund that pays out Social Security benefits. Recently, the board released its 2025 report, and below is my summary…
Teaching Kids That Money Is Finite
If your children or grandchildren never feel the sting of running out of money, will they ever learn to manage it? For families with wealth, this is one of the more underappreciated challenges in raising up the next generation. I’ve seen this firsthand from many clients who express concerns that their grandchildren don’t seem to share the same financial values they do…
How Many Hours Should Your Teen Really Work?
Most clients I’ve met with have two reactions when their teen child or grandchild lands a job. The first is pride, and the second is worry about time management and homework.
How much work is too little? Too much? It turns out, this question has been researched. I recently came across this article from The University of Minnesota and a few other institutions that have followed this topic for decades…
Optimizing Tax Lot Selling
Many clients have spent decades building a brokerage account by consistently saving, reinvesting dividends, and staying invested through the bumps. Now, as they approach retirement, they are ready to start drawing it down. The question most people never think to ask until they are actually selling: which shares do you sell first?
The answer can save you thousands of dollars a year in taxes…
When Tax Brackets Lie to You
On paper, a retiree can look like they are firmly in the 12% bracket. In practice, their next dollar of income can cost nearly three times that. The reason is due to the way the tax system works, particularly something called “income stacking.”
Take a retired couple, the Smiths. Their income this year looks like this: $48,000 in ordinary income from Social Security, a small pension, and interest, alongside $130,000 in long-term capital gains and qualified dividends from their brokerage account…
When Pre-tax (not Roth) 401k Contributions Can Make Sense
Most people think of the Roth vs. pre-tax 401(k) decision as a simple bet on future tax rates. But there is a more specific opportunity hiding in that choice, particularly in the years leading up to retirement, and it has everything to do with where in the bracket structure your deduction lands versus where your Roth conversion starts…