Why People Come to Us: 5 Common Retirement Planning Questions
Christopher Mallon
July 8th, 2025
Planning for retirement brings a mix of excitement and uncertainty. Many of the people we meet have done an admirable job saving and investing over the years—but as they approach the finish line, new questions emerge. These aren’t just financial questions—they’re life questions, and understandably, there’s no one-size-fits-all answer.
Here are five of the most common questions we hear—and a look at how we help our clients find clarity.
1. Do I Have Enough to Retire?
This is, hands down, the most common question we get—and the one that often keeps people up at night. What they’re really asking is, “Am I going to be okay?”
To answer that, we gather a complete picture of their financial situation, including:
- Investment and retirement account statements (whether we manage them or not)
- Any outstanding debts or liabilities
- Annual household expenses
- Expected retirement income (including pensions, annuities, part-time work)
- A Social Security statement (the “waterfall” report)
- Estimated values of any illiquid assets like real estate
With that data, we create dynamic, easy-to-understand projections that show what retirement might look like. Want to factor in an annual $25,000 family trip for the next 10 years? We can model that instantly and show the long-term impact.
2. When Should I Take Social Security?
There’s no universal answer to this one. The “right” claiming strategy depends on your age, health, marital status, income needs, and broader financial plan.
Once we have your Social Security statement, we run side-by-side projections for claiming at 62, full retirement age, or delaying until 70. These projections help clients weigh the trade-offs between monthly benefit amounts and long-term lifetime income.
3. How Should I Invest Now That I’m Retired?
Many of our clients have been diligent savers and investors during their working years. But retirement changes the game—from accumulating assets to drawing them down.
We design portfolios that aim to balance two key goals:
- Providing reliable income to meet short-term needs
- Continuing to grow over time to combat inflation and support long-term goals
For many retirees, we’re planning for 20–40 years without paychecks. That’s a long time for assets to last—and the investment strategy must reflect that.
4. How Do I Plan for Taxes in Retirement?
This is one of the most overlooked (but critical) parts of retirement planning.
By reviewing your tax returns and asset locations (e.g., IRAs vs. taxable brokerage accounts), we can develop a withdrawal strategy that minimizes taxes and extends the life of your portfolio. For example, if a client has 70% of assets in IRAs and 30% in taxable accounts, we map out when and how much to withdraw from each “bucket” based on current tax brackets, Medicare thresholds, and RMD rules.
5. What Will Healthcare Cost Me?
Medicare can be confusing—and expensive, especially if you’re not careful.
We help clients understand the different parts of Medicare, evaluate supplemental and Advantage plans, and aim to avoid costly surprises. One key consideration is that your premiums are based on your income from two years prior. That’s why we incorporate income planning into our tax strategy to help avoid unnecessary premium surcharges.
Final Thoughts
Every retiree’s situation is unique. While these questions are common, the answers need to be tailored. That’s why our planning process is so thorough—and why our goal is for our clients to feel more confident when they walk out of our office than when they walked in.
If you’re 2–5 years away from retirement and find yourself wondering about any of the above, we’d love to help you get some answers.
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