RetireVibes · Advisor guidance

How to find a retirement advisor who actually knows what they're doing.

What to look for, what to ask, and where to search — without wading through a sea of generalists who fit retirement in between college savings accounts and business insurance.

When to start

Earlier than you think. Much earlier.

The most common mistake isn't picking the wrong advisor — it's waiting until you're 18 months from retirement to find one. By then, the high-leverage decisions are mostly locked in.

10–15 years out

The real planning window

This is when Roth conversions, Social Security optimization, and asset location decisions can actually move the needle — sometimes by six figures over a 20-year retirement. An advisor at this stage is helping you build the foundation, not just manage what you've already built.

5–10 years out

Where most people start

Still plenty of time to adjust the plan. Key questions at this stage: Medicare timing, whether to do a final Roth conversion push, what the withdrawal sequence will look like, and — if you're moving — what state tax treatment means for your income sources.

1–3 years out

Transition planning

If you don't have an advisor yet, now is urgent — not because it's too late to do anything, but because this is when the irreversible decisions happen. Social Security start date, Medicare enrollment windows, and pension elections usually can't be undone. Get someone in the room.

What to look for

Five things that actually matter.

1

Fiduciary, always

A fiduciary is legally required to act in your interest — not their firm's, not their quota's. Ask directly: "Are you a fiduciary at all times, for all services?" Some advisors are fiduciaries only for certain services. You want "always" as the answer.

2

Fee-only, not fee-based

Fee-only advisors are paid by you directly — hourly, flat fee, or a percentage of assets. Fee-based advisors can also earn commissions from products they sell you. The distinction matters. Ask: "How are you compensated, and do you earn commissions on any products you recommend?"

3

Retirement specialist, not generalist

A generalist handles 401k rollovers, business succession, estate planning, and college savings all in the same week. A retirement specialist has built their practice around the specific phase of life you're entering — drawdown strategy, Social Security, Medicare, and late-stage tax planning. You want the specialist.

4

International experience (if retiring abroad)

Retiring outside the US adds a full layer of complexity that most domestic advisors aren't trained for: FBAR filings, FATCA, foreign tax credits, treaty provisions, and in some countries, local pension rules that interact with US Social Security. An advisor without expat-specific experience is learning on your dime.

5

Real client history in your situation

Ask for examples of clients with a similar profile — similar income sources, similar destination, similar timeline. "I've worked with clients like you" is not the same as "here's what that looked like and what we did." You want specifics, not reassurance.

Questions to ask

Six questions for your first conversation.

Any good advisor will answer these clearly and without hesitation. Vague answers are information too.

01
"Are you a fiduciary at all times, for every service you provide?"

The correct answer is yes. Anything else — "for investment advice, yes" or "as an RIA, yes" — means no for at least some of what they do.

02
"How do you charge, and what exactly am I paying for?"

Get the fee structure in writing before you sign anything. Common models: % of assets under management (AUM), hourly, or flat retainer. Each has tradeoffs — understand what you're getting for what you're paying.

03
"What percentage of your clients are retired or within five years of retirement?"

A specialist's practice skews heavily toward this demographic. If the answer is less than half, you're not their core client type — and that shows in how well-calibrated their advice is.

04
"Have you worked with Americans retiring to [destination]? What does that work look like?"

For international moves specifically. You want someone who has done this before — who knows the visa types, the tax treaty provisions, and which questions to bring to a local attorney vs. handle themselves.

05
"Can you walk me through how you'd approach my Social Security and Medicare decisions?"

Not hypothetically — as if you were their client. This tells you immediately whether they understand the nuance (spousal benefits, delayed credits, Medicare IRMAA thresholds) or are giving you a generic answer.

06
"What happens if I need to change course — can I get out, and what does that cost?"

Understand exit terms before you begin. AUM-based relationships in particular can have switching costs. Good advisors are transparent about this. It's not a red flag to ask — it's a red flag if they bristle at the question.