Retiring Soon? Common Questions People Ask a Financial Advisor
Most retirement questions show up wearing a money mask.
People ask about Social Security, taxes, budgets, and whether they have “enough.” Those are important. But after decades of sitting across the table from future retirees, I have learned that the question underneath the question is often this:
What if I retire and I do not like retirement?
A good retirement plan should help you answer the math, but it should also help you build a life you actually want to live. Below are common questions I hear, and the practical framework I use to help people work through them.
If you prefer to listen instead of read, here is the episode this post is based on: Listen to the podcast.
1) “What does retirement actually look like for me?”
This is the most valuable question on the list, and it is rarely the first one asked.
Financial independence creates options. It does not automatically create structure, meaning, or community. Work provides built-in routines, social interaction, and a sense of progress. When that disappears overnight, some people feel unexpectedly adrift.
A simple exercise I recommend is building a “retirement week” draft before you retire:
- 3 anchors: 3 recurring commitments that get you out of the house (volunteering, grandkids, classes, fitness group, faith community, part-time role)
- 2 social touchpoints: planned time with friends or peers
- 1 growth lane: something that keeps you learning (mentoring, coursework, a new skill)
- 1 recovery lane: rest and leisure you protect on purpose
This is not about filling every hour. It is about making sure your days have rhythm.
Research supports the general idea that meaningful engagement matters in retirement. For example, studies have found associations between volunteering and improved well-being for older adults, including lower depressive symptoms in some populations. This is not a prescription, just a reminder that purpose and connection are not “soft” issues in retirement planning.
Sources: ScienceDirect (volunteering and depression in early retirement) and related academic literature on volunteering and well-being.
2) “Why do hobbies feel different once I retire?”
A surprising dynamic I see: once you have unlimited time, the hobby can stop feeling like a hobby.
When something moves from “I get to do this” to “I should be doing this,” it can turn into pressure. That is one reason some retirees find their “wish list” activities feel more like obligations than fun.
A helpful fix is to mix performance hobbies with restorative hobbies.
- Performance hobby examples: golf handicap goals, training for events, competitive leagues
- Restorative hobby examples: walking, fishing for pleasure, photography, reading, travel planning, casual volunteering
Performance hobbies are great. Just do not make your entire retirement identity ride on them.
3) “Can I work in retirement, or do I have to work part-time?”
You can work as much or as little as you want, but there is an important nuance if you claim Social Security before full retirement age.
The key rule: the Social Security retirement earnings test (2026)
If you claim retirement benefits before full retirement age and have earned income above certain thresholds, Social Security may temporarily withhold some benefits. For 2026, the Social Security Administration lists these exempt amounts:
- $24,480 if you are under full retirement age for all of 2026
- $65,160 if you reach full retirement age during 2026 (this higher limit applies only to earnings before the month you reach full retirement age)
Withholding formulas:
- Under full retirement age: $1 withheld for every $2 earned above the lower exempt amount
- In the year you reach full retirement age: $1 withheld for every $3 earned above the higher exempt amount (before the month you reach full retirement age)
Important clarification: withheld benefits are not “lost.” SSA explains that your benefit is adjusted upward at full retirement age to account for months in which benefits were withheld due to the earnings test.
Sources: SSA exempt amounts page and SSA program explainer, plus SSA publication “How Work Affects Your Benefits.”
Why working in retirement is common
A lot of people do not go back to work because they “need” to. They do it because they want structure, social contact, and something that feels useful.
Government data backs up the broader trend that many older Americans remain in the labor force. The Bureau of Labor Statistics has reported that in 2024 about one in five people age 65+ participated in the labor force (working or looking for work), and among employed people age 65+, 38.3% worked part-time.
Source: U.S. Bureau of Labor Statistics (The Economics Daily).
Practical note: rules can be nuanced, especially for self-employment, partial-year retirement, and how earnings are counted. When Social Security is involved, I encourage people to review the details directly with SSA or a qualified professional.
4) “My spouse and I do not agree on spending. How do we make retirement work?”
This is more common than people admit.
Retirement amplifies existing money dynamics because:
- both spouses are home more often
- spending becomes more visible
- the paycheck rhythm is gone
- decisions shift from “saving for someday” to “spending with confidence today”
In my experience, the best path is not policing line items. It is agreeing on guardrails.
Examples of retirement guardrails:
- a target monthly spending range based on the plan
- an annual “fun budget” for travel and hobbies
- a shared rule for large purchases (example: anything over a set amount requires a 24-hour pause and a joint yes)
- separate discretionary accounts for “no-questions-asked” spending
The goal is clarity, not control.
5) “Should we tell our adult kids what they might inherit?”
This question is loaded because it is not just about money. It is about expectations, responsibility, and family dynamics.
There is no universal right answer. But there are two principles I think matter:
Principle 1: Your kids should know the plan for an emergency
Even if you never share account balances, consider making sure your adult children (or the right trusted person) know:
- who to call (advisor, attorney, CPA)
- where key documents are (estate documents, insurance policies, account list)
- what your wishes are (health care directives, executor, beneficiaries)
Principle 2: Do not let inheritance expectations drive your retirement
If you want to leave a legacy, that is a valid goal. But it should be intentional, not accidental.
Estate planning is a legal topic, and it should be handled with a qualified attorney. As values, accounts, and laws change over time, it is also worth revisiting periodically.
The “Retiring Soon?” Question List
If you are nearing retirement, here is a clean set of questions to bring to your planning conversation:
- What does a great retirement week look like for us?
- What spending level is sustainable, and what assumptions is that based on?
- What are our income sources, and what is the timing for each one?
- How should we think about Social Security timing, especially if we plan to work?
- What are the biggest retirement risks for us (longevity, inflation, health care, market volatility)?
- How will taxes change when we shift from earning to drawing income?
- What do we want our legacy to be, and what is the simplest way to document it?
Sources
- Social Security Administration, “Exempt Amounts Under the Earnings Test” (includes 2026 limits): https://www.ssa.gov/OACT/COLA/rtea.html
- Social Security Administration, “Program Explainer: Retirement Earnings Test”: https://www.ssa.gov/policy/docs/program-explainers/retirement-earnings-test.html
- Social Security Administration, “How Work Affects Your Benefits” (publication): https://www.ssa.gov/pubs/EN-05-10069.pdf
- U.S. Bureau of Labor Statistics, The Economics Daily (older Americans working part-time): https://www.bls.gov/opub/ted/2025/38-3-percent-of-employed-older-americans-worked-part-time-in-2024.htm
- Research example on volunteering and well-being in retirement: https://www.sciencedirect.com/science/article/pii/S0277953625001194
Disclosures
Fortress Financial Group LLC is a registered investment adviser. Registration does not imply a certain level of skill or training. This material is for general information and educational purposes only and is not intended to provide specific investment, legal, or tax advice. Any references to planning strategies are general in nature and may not be appropriate for all individuals. Investing involves risk, including the possible loss of principal.
Social Security rules are complex and subject to change. For questions about your specific benefits, consult the Social Security Administration or a qualified professional. For legal or tax matters, consult your attorney and tax professional.
