.avif)
Finding the right financial advisor as you approach retirement is one of the most important financial decisions you'll make. The stakes are high — this is the person who will help you answer the questions that matter most: when you can retire, how much you can spend, how to minimize your tax bill, and how to make sure your money lasts.
The flat fee financial advisor model is still relatively new to the industry, and many people considering it have never hired an advisor this way before. Whether you're evaluating Arcadia or another firm, these are the nine questions we believe every prospective client should ask before signing on — along with our own answers for context.
This question matters more than most people realize. Some advisory firms operate at scale — one advisor managing hundreds of client relationships simultaneously. Others deliberately limit their practice to ensure every client gets genuine attention.
The size of an advisor's client base affects how much time they can actually spend on your situation. An advisor managing 200 clients probably isn't thinking about your Roth conversion strategy or your Medicare premium exposure — they're too busy returning phone calls.
At Arcadia: We deliberately limit our practice to approximately 40 households. That number isn't arbitrary — it's what allows us to proactively think about each client's financial situation year-round, not just when they call us. When a tax law changes, when the market moves, or when a planning opportunity arises, we want every client to be top of mind. At 40 households, that's achievable. At 200, it probably isn't.
This one catches some people off guard — but think about it. Would you trust a chiropractor who never went to a chiropractor themselves? A financial advisor who doesn't use a financial advisor is either overconfident in their own objectivity or hasn't thought carefully about the value of an independent third party.
Even the most financially knowledgeable people benefit from having someone who can step back, look at the full picture without emotional attachment, and give honest advice — especially a spouse or family member who may not be equipped to manage finances if the primary financial decision-maker is no longer able to.
At Arcadia: Yes. We work with trusted advisors for our own financial lives. Not because we can't manage our own investments and tax planning— we certainly can. But because we understand firsthand the value of having someone who knows our full financial situation and can step in quickly for our families if we're ever unable to do so. It also keeps us sharp! Walking in our clients' shoes makes us better advisors.
There are two primary investment philosophies: active and passive. Active managers try to outperform the market by picking stocks and timing moves. Passive managers build a diversified portfolio appropriate for the client's goals and risk tolerance, keep costs low, and let the markets do the work over time.
The data on this is not subtle. According to the most recent SPIVA Scorecard, over 90% of active U.S. equity fund managers underperformed their benchmark on a risk-adjusted basis over the last 20 years. The odds of your advisor being among the exceptions are very low — and the cost of being wrong is paid entirely by you.
At Arcadia: We implement a passive, evidence-based investment strategy for every client. We build globally diversified portfolios using low-cost index funds and ETFs, aligned to each client's risk tolerance and time horizon. We review accounts at least quarterly, rebalance when appropriate, and implement tax-loss harvesting strategies when they add value. We don't try to predict markets — because nobody can do that consistently — and we don't charge you for the attempt.
This is one of the most important questions on this list — and the one where you need to dig deepest. The wealth management industry is notorius for fee structures that look simple on the surface but are considerably more complex in practice.
Some advisors advertise themselves as 'flat fee' for financial planning but then charge assets under management once you become a client — effectively layering fees on top of each other. Others earn compensation by placing clients in specific products like annuities or permanent life insurance policies that may or may not be appropriate for the client's situation. Many charge assets under management (AUM) fees where your fees grow as your investment portfolio grows.
Ask specifically: What will I pay? How is it calculated? Are there any other ways you or your firm are compensated — directly or indirectly — from my account or from third parties?
At Arcadia: Our fee is straightforward: $18,000 per year ($4,500 per quarter). That fee covers a complete household — both spouses, every account, all planning needs. There is no separate fee for investment management. There are no commissions. There are no product sales. No assets under management (AUM) fees. We are compensated exclusively by our clients, which means our only financial incentive is to give you the best possible advice.
The word 'fiduciary' gets used a lot in financial services. What many people don't realize is that some advisors are only fiduciaries some of the time. These are called dually registered advisors — they can operate as a fiduciary when providing financial planning advice, but switch to a lower standard of care when selling financial products like annuities, insurance policies, or private investments.
This matters because the advice to buy a particular product and the recommendation to implement a financial plan are not always the same thing. An advisor who can shift their standard of care depending on the situation creates a conflict that may not be obvious to the client.
At Arcadia: We are fiduciaries 100% of the time. We are not dually registered. We do not sell financial products. We do not earn commissions or have an incentive to gather assets. Every recommendation we make is held to the fiduciary standard — legally required to be in your best interest, not ours.
The financial industry has dozens of designations, and not all of them require the same level of rigor, education, or ongoing commitment. Some can be earned in a weekend. Others require years of study, a comprehensive examination, thousands of hours of experience, and ongoing continuing education.
Within financial planning, the most meaningful designations are the CFP® (CERTIFIED FINANCIAL PLANNER™), the CFA (Chartered Financial Analyst), and the CPA (Certified Public Accountant). For retirement-focused planning, the TPCP® (Tax Planning Certified Professional) designation reflects deep expertise in tax strategy — one of the most impactful areas of planning for retirees.
At Arcadia: Grant Webster holds both the CFP® and TPCP® designations. The CFP® represents comprehensive financial planning expertise — investments, retirement, estate, insurance, and tax. The TPCP® reflects advanced training in proactive tax planning, which is increasingly central to what we do for clients in or approaching retirement. We believe this combination is genuinely differentiated, and we'd be happy to explain what each designation covers in more detail.
The best financial advisors have deep experience with the specific situations and questions their clients face. An advisor who primarily serves business owners in their 40s isn't going to have the same depth of expertise in retirement income planning, Medicare strategy, and RMD optimization as one who has spent years working primarily with retirees and pre-retirees.
Ask specifically: Do you regularly work with clients at my life stage? What are the most common planning challenges you address for clients like me?
At Arcadia: The clients we serve are primarily in two groups. The first are those who are retired and want confidence that their financial plan is sound, their withdrawals are tax-efficient, and their money will last. The second are those who have reached financial independence — typically between ages 45 and 65 — but continue working because they choose to. Both groups share a common set of planning needs: retirement income strategy, Social Security optimization, tax planning, Medicare planning, and estate coordination. This is our specialty. We've spent nearly two decades helping hundreds of families navigate exactly these questions.
The frequency and quality of communication between advisor and client varies enormously across the industry. Some advisors send quarterly performance reports and schedule an annual review. Others are proactively reaching out throughout the year — when tax laws change, when market events create planning opportunities, or when something in a client's life warrants attention.
As you approach and enter retirement, proactive communication becomes more important — not less. The decisions that matter most in this phase of your financial life don't always follow a quarterly schedule.
At Arcadia: We typically have two formal meetings each year: one in late Spring (May/June) and in the Fall (October/November). At our Spring meeting we review your tax return and do an analysis to look at opportunities for the remainder of the year. We meet in Fall to implement tax strategies before year-end. At both meetings, we review your financial plan and investment portfolio. We are available for calls, emails, and “pop up” meetings as needed. Our clients have direct access to us throughout the year. We're not hard to reach!
This might be the most underrated question on this list. A good financial advisor should be able to tell you clearly what they're working toward — not in vague terms like 'growing your wealth,' but in specific, meaningful outcomes tied to your life.
If an advisor can't articulate what a successful client relationship looks like over a 5 or 10-year horizon, that's probably a red flag. It may mean they're focused on managing your investments rather than planning your financial life — and those are not the same thing.
At Arcadia: Success in our client relationships looks like this: you retire when you want to, you spend confidently in retirement without fear of running out, you minimize what you send to the IRS, and your estate passes to the people you love in the most efficient way possible. We want our clients to feel genuinely prepared — not just for the good years, but for the unexpected ones too.
Hiring a financial advisor is a significant decision — and it should feel like one. The right advisor isn't just someone who manages your investments competently. They're someone you trust to help you navigate one of the most financially complex periods of your life, with clarity, honesty, and genuine expertise.
The questions above won't guarantee you'll find the perfect fit — but they'll help you ask the right things, evaluate the answers honestly, and make a more informed decision.
Disclosure: This article is for informational purposes only and does not constitute personalized tax, legal, or investment advice. Tax rules are subject to change. Please consult a qualified financial advisor and CPA for guidance specific to your situation. Arcadia Private Wealth LLC is a Registered Investment Adviser in the state of California. Advisory services are only offered to clients or prospective clients where we are properly registered or exempt from registration.
Grant Webster, CFP®, TPCP®
Founder, Wealth Advisor