8 Questions to Ask a Financial Advisor Before You Retire in San Diego
Sam's List Editorial | 2026-07-14
8 Questions to Ask a Financial Advisor Before You Retire in San Diego Most people pick a financial advisor the way they pick a dentist. A friend mentioned a name, the office was close, and that was that. Retirement is the wrong place to run on vibes. The questions to ask a financial advisor before retirement are not complicated, but almost nobody asks them in the first meeting. San Diego adds its own wrinkles: a high cost of living, a lot of pensions and equity comp mixed together, and a retiree population that skews toward wanting someone local. These retirement planning questions are the ones that separate a real plan from a sales pitch, plus two more that catch people off guard. 1. How Are You Compensated? Ask this before anything else. Some advisors work on commission, some charge a flat fee, some charge a percentage of assets under management, and some blend two or three of those. Each structure creates different incentives, and none of them are automatically bad, but you need to know which one you are dealing with. A commission-based advisor gets paid more when you buy certain products, which does not mean the product is wrong for you, but it means you should ask why that specific product over another. A fee-only advisor is paid the same regardless of what they recommend, which removes one layer of conflict but does not remove all of them. Get the compensation structure in writing, not just a verbal explanation. 2. How Will You Manage Sequence-of-Returns Risk in My First Five Years? The five years around your retirement date matter more than almost any other stretch. If the market drops 20% in year one or two of retirement and you are pulling money out at the same time, that loss compounds in a way it would not if you were still working and adding to your accounts. This is sequence-of-returns risk, and it is one of the most underexplained concepts in retirement planning. Ask specifically what the advisor does about it. A real answer sounds like a cash reserve to ride out a downturn, a bucket strategy that separates near-term spending from long-term growth, or a flexible withdrawal rate that adjusts in a bad year. A vague answer about "staying diversified" is not a plan, it is a hope. 3. How Do You Coordinate With My CPA on Withdrawal Order? The order you pull money from taxable accounts, traditional IRAs, and Roth accounts changes your lifetime tax bill by tens of thousands of dollars in many cases. Getting that sequence right requires an advisor who actually talks to your CPA, not one who treats tax planning as someone else's job. Ask whether the...
