Mailbag: PTO, Vacation Pay & Social Security

TaylorMade Retirement with Taylor Demars, CFP® · May 21, 2026 · 11m · transcript

A listener question came in with a deceptively simple retirement question: Should you start Social Security right away if you don’t actually need the income yet? Taylor explains why the answer involves much more than math, touching on PTO, retirement lifestyle, flexibility, and long-term planning decisions. Before you claim a single dollar, make sure you’re not walking into a Social Security timing trap.

Here’s what we discuss in today’s show:

💸 Social Security Triangle: Three ways to evaluate timing

🧠 Psychology Matters: Confidence changes spending habits

🏖 PTO Test Drive: Practice…