Waypoint No. 9 · October 2026 · A Shetland Financial Publication Social Security for Married Couples: One Decision, Not Two For married couples, the most important Social Security decision is when the higher earner claims. That check becomes the surviving spouse’s income for life. A single retiree faces one question: when do I start? A…
Waypoint No. 8 · August 2026 · A Shetland Financial Publication Unwinding a Concentrated Position Without a Disaster The math is rarely the hard part. The sequencing, the constraints, and the calendar are. The problem Most large concentrated positions weren’t built on purpose. They’re the residue of something that went right. A company that got…
Waypoint No. 6 · August 2026 · A Shetland Financial Publication Beneficiary Designation Audits Your beneficiary forms override your will. Most people haven’t looked at theirs in years. The problem There’s a particular kind of estate planning failure we see more than any other. It doesn’t involve a contested will, an aggressive creditor, or some…
Waypoint No. 5 · July 2026 · A Shetland Financial Publication Trump Accounts Are Here After about a year of hearing about it, Trump Accounts are now finally off the ground. They were a part of the 2025 tax law and are a brand new type of savings vehicle. The idea is to give kids…
Waypoint No. 4 · June 2026 · A Shetland Financial Publication The Estate Tax Cliff That Never Came For years, nearly every estate planning conversation was shaped by a deadline. The Tax Cuts and Jobs Act of 2017 had roughly doubled the federal estate and gift tax exemption, from about $5.5 million per person to…
Mid-Year Tax Check-In: 5 Moves Before June 30 Most people don’t think about taxes until April. But if you wait that long, many of your best opportunities are already gone. The window between now and June 30 is one of the most valuable, and most overlooked, moments in your financial year. Half the year has…
SALT Deduction After OBBBA: Who Actually Benefits at $40K For the past several years, the $10,000 cap on state and local tax deductions has been one of the most consistent frustrations for clients in high-tax states. New Jersey income tax, Pennsylvania property taxes, Philadelphia wage tax. For many households, actual SALT liability was two or…
Waypoint No. 1 · May 2026 A Shetland Financial Publication Welcome to the first issue of Waypoint. As we mentioned in recent weeks, we are stepping back from weekly market commentary and toward something more useful: twice-monthly notes on the tax and planning decisions that actually move the needle. Our first issues covers Roth conversions….