When to meet with a Financial Advisor
Jason Stolz CLTC, CRPC
Life changes fast—your financial plan should change with it. Whether you’re switching jobs, receiving an inheritance, approaching retirement, or navigating divorce, each milestone creates tax, cash-flow, insurance, and estate implications. Knowing when to meet with a financial advisor helps you capture opportunities, avoid expensive mistakes, and stay on track when life doesn’t go exactly as planned.
At Diversified Insurance Brokers, we help clients align retirement income planning, annuities, insurance, and long-term protection—then revisit the plan whenever life changes. If you’re within five years of retirement, start with our Pre-Retirement Checklist to make sure the essentials are handled before you lock in a retirement date.
20 Life Events That Should Trigger a Meeting
1) New job or career change
A job change usually brings new retirement plan options, employer benefits, and tax adjustments. Review your old 401(k) or 403(b) to decide between rollover, conversion, or consolidation. A review can also coordinate employer life and disability benefits—so you’re not relying on group coverage alone. If stability is a priority, a rollover may also involve exploring an IRA-to-annuity approach for conservative, tax-deferred accumulation depending on your goals and timeline.
2) Pay raise, bonus, or stock compensation
When your income jumps, lifestyle tends to follow unless you redirect part of the increase. A meeting is a good time to increase retirement plan contributions, build a tax plan, and consider how to create predictable future income. If you want a more conservative bucket alongside market exposure, compare guaranteed options such as short-term MYGA annuities or explore structured income planning using annuities for a portion of retirement assets.
3) Starting a business or side practice
Entrepreneurs face unique risks: uneven income, tax complexity, and lack of employer benefits. A planning review helps evaluate retirement plan choices and income protection. If your business depends on you showing up to work, consider Business Overhead Disability Insurance to help cover fixed expenses if you can’t work. This is also the time to structure buy-sell planning and fund it efficiently through life or disability coverage.
4) Marriage or domestic partnership
Marriage combines more than hearts—it merges financial responsibilities. Coordinating insurance, estate planning, and tax filing status early prevents later surprises. This is also when couples often evaluate predictable retirement income options like joint-life annuity income scenarios, especially when one spouse plans to retire earlier than the other.
5) Divorce or separation
Divorce affects retirement accounts, beneficiary designations, and sometimes annuity ownership. A review helps divide assets strategically to preserve tax advantages and minimize surrender charges. If annuities are involved, start with How Annuities Are Divided in Divorce and What Happens to Your Annuity in a Divorce? so you understand the common pitfalls before paperwork gets finalized.
6) New child or adoption
Parenthood changes priorities overnight. A meeting should tighten life insurance coverage, disability protection, and beneficiary structure. If the family depends on your income, income protection matters as much as life insurance. Professionals and business owners may also explore key-person coverage such as Key Employee Disability Insurance to stabilize cash flow if someone essential can’t work.
7) Major purchase or sale (home, business, property)
Big transactions change liquidity, taxes, and debt ratios. A review helps avoid over-committing to a payment while underfunding retirement. Some clients reposition part of equity into safe-growth solutions like fixed indexed annuities with lifetime income riders to reduce market risk while still keeping a path to growth.
8) Inheritance or windfall
Sudden wealth can trigger rushed decisions. A meeting helps slow the process, build a tax-aware plan, and decide what portion should stay liquid versus what portion can be positioned for predictable long-term income. Many clients allocate part of a windfall toward stable retirement income planning and compare options using current annuity rates as a starting point.
9) Health change or new diagnosis
A health change impacts insurance eligibility and long-term care risk. A review should look at cash reserves, deductibles, and long-term care coverage. Planning early gives you more options; if you want a “use it or benefit later” structure, explore hybrid long-term care policies or return-of-premium LTC solutions depending on your priorities.
10) Caring for aging parents
Family caregiving can strain finances and time. A review helps coordinate budgets and evaluate long-term care options such as Partnership-Qualified long-term care insurance, plus contingency planning if a caregiver reduces work hours. It’s also a good time to verify beneficiary and estate documents across the family to reduce chaos later.
11) Approaching retirement (5–10 years out)
This is often the best time to lock in predictable income sources. A meeting should stress-test your plan against a market downturn, inflation, and health costs. Many clients compare lifetime income rider strategies and coordinate them with Social Security strategy so your baseline income stays dependable.
12) Retirement date is set
Once the countdown begins, your focus shifts to distribution planning: Social Security timing, pension election, and withdrawal sequence. Many clients want a clear picture of predictable income, so we review annuity payout scenarios such as how much a $1 million annuity can pay and coordinate that with claiming decisions.
13) Market volatility or rate shocks
Volatility matters most when you’re withdrawing. A review can create a “paycheck floor” so essential expenses stay funded even when markets are down. Some clients use a portion of assets for contractually predictable income, then let the rest stay invested for growth. If legacy matters, combining income strategies with beneficiary-focused planning like annuity beneficiary and death benefits can reduce surprises.
14) Paying off major debt
When debt disappears, cash flow opens up. A review helps redirect the old payment into long-term savings or predictable income planning. If you want to understand “real dollar” scenarios, compare examples like how much a $500,000 annuity can pay based on age and options.
15) Tax law changes
Tax changes can affect RMD planning, Roth conversions, and distribution sequencing. A review helps coordinate account types and withdrawals so you’re not surprised by taxes later. Some clients also compare strategies like bonus annuity structures when they want to strengthen long-term income planning while staying conservative on principal.
16) Beneficiary or estate updates
Outdated beneficiaries can override your will. A planning review should confirm beneficiaries on retirement accounts, annuities, and life insurance. If annuities are part of your plan, start here: Annuity Beneficiary & Death Benefits.
17) Insurance coverage gaps
Life and income protection should be reviewed as income and responsibilities change. Many higher earners rely too heavily on employer coverage, which often isn’t portable and may not be enough. If you want a stronger base, explore profession-specific planning and high-limit options like high-income disability insurance.
18) Considering long-term care solutions
Planning early expands your options. A review can compare traditional LTC to hybrid solutions and evaluate tax considerations like tax benefits of long-term care insurance. If asset protection matters, Partnership-Qualified LTC planning can be a major advantage depending on state rules and your situation.
19) Charitable or legacy planning
If you want to give efficiently, a review can coordinate gifting with tax strategy and retirement income. For IRA owners, explore Qualified Charitable Distributions as a way to support causes while reducing taxable income in the right situations.
20) Any “gut-check” moment
If you’re uneasy about taxes, spending rate, market direction, or retirement timing, it’s time for a check-in. A short review can prevent big mistakes—especially around Social Security timing and realistic retirement income projections like annuity payout scenarios.
What to Do After You Identify a Trigger Event
Reading a list of “trigger events” is helpful, but the real value comes from what you do next. Most financial mistakes don’t happen because people lack intelligence—they happen because people act quickly during stressful transitions. After a life event, the best next step is to slow down and organize the decision into a short sequence: confirm what changed, list what the change impacts, choose your priorities, then align your accounts and protections to match those priorities.
For example, if you changed jobs, you might be focused on your new salary and benefits, but the real planning risk is often the “loose ends” you left behind: an old 401(k), an old life policy, a disability plan you can’t take with you, and beneficiaries that were never updated. If you received an inheritance, the biggest risk is not “choosing the perfect investment.” It’s making an irreversible tax decision, overcommitting to an illiquid strategy, or letting emotion drive the timeline.
A good planning meeting turns the trigger event into a checklist of actions with deadlines. It clarifies which decisions are reversible and which ones are not. It also helps you avoid the common trap of doing “something” just to feel productive, when the smartest move is often to first build a simple framework and keep liquidity until the plan is clear.
What a Good Financial Advisor Meeting Should Actually Produce
Many people schedule a meeting expecting a product pitch. That’s not what a useful review looks like. A strong meeting should produce clarity and next steps. When the meeting is done, you should know what accounts need attention, what risks are currently uncovered, how taxes should be handled, and which decisions matter most in the next 30–90 days.
In practical terms, here are outcomes we target for clients at Diversified Insurance Brokers: a clear retirement income picture (what’s guaranteed versus what’s variable), a map of where your savings sits (taxable, tax-deferred, tax-free), an assessment of insurance gaps (life, disability, long-term care), and an action plan that fits your time horizon. If annuities are part of your plan, the meeting should also clarify whether the annuity is being used for growth, for guaranteed income, or for a balanced approach—because the strategy selection is different depending on the goal.
If you are within five years of retirement, that “clarity” step becomes even more valuable because sequence-of-returns risk becomes real. A market drop right before retirement can permanently reduce outcomes if withdrawals continue. That’s why many clients who are close to retirement start with our Pre-Retirement Checklist and then build an income plan that includes a predictable baseline.
Why Reviews Matter: The 4% Rule Isn’t a Plan
Rules of thumb can be helpful, but they’re not a retirement plan. Static withdrawal rules ignore today’s realities: longer lifespans, inflation spikes, healthcare costs, and sequence risk. If a downturn hits early and you keep withdrawing, a portfolio can be permanently impaired. One common solution is carving out a portion of assets for contractually guaranteed income, so essentials are covered regardless of markets, while the remainder stays invested for growth and flexibility.
If you want to see real-world payout scenarios (instead of generic percentages), these resources can help: What Is the 4% Rule? and How Much Does a $1 Million Annuity Pay?. Those pages help you evaluate whether a portion of guaranteed income would reduce stress and improve the sustainability of your plan.
How Annuities Can Fit Into a “Two-Bucket” Retirement Strategy
One of the simplest ways to make retirement planning easier is to separate your money into “purpose buckets.” A common approach is using one bucket for predictable income and stability, and another bucket for growth. The stability bucket may include Social Security, pensions, and potentially annuities that can create a contractually defined income stream. The growth bucket may include market-based investments designed to outpace inflation over time.
This approach isn’t about choosing annuities instead of investments. It’s about making sure your essential expenses can be covered even when markets are down. Many people find they can take better long-term investment risk when the basics are protected, because they’re less likely to panic-sell during downturns. If you’re exploring options, start with current annuity rates, then compare the role of annuities in broader planning using the framework in how much a $500,000 annuity can pay and how much a $100,000 annuity can pay based on age and options.
Where Life Insurance Fits—Even If You Think You “Don’t Need It”
Life insurance is not only for parents with young kids. It is also a planning tool for couples, business owners, and families who want a cleaner transfer of wealth and a more predictable legacy. During many “trigger events,” life insurance becomes more important, not less—especially marriage, divorce, business changes, inheritance planning, and retirement planning.
For example, in retirement income strategies, annuities can be used to create dependable income, while life insurance can help protect heirs. That combination can be particularly useful for couples who want the confidence of a lifetime paycheck but also care about leaving something behind. If you’re a business owner, life insurance is often part of buy-sell planning and business continuity. If you have debt, co-signed obligations, or a spouse who depends on your income, the case for coverage becomes even clearer.
We also see life insurance matter most when health changes are on the horizon. If you are still healthy, it may be the best time to lock in coverage before underwriting becomes more difficult. That’s why a meeting after a health change is valuable: it helps you separate what should be addressed now versus what should be reviewed annually going forward.
Get a Life Insurance Estimate
If one of your “trigger events” involves new family responsibilities, debt, business planning, or protecting a spouse, it helps to start with a baseline estimate. Use the tool below to get a quick quote range, then we can help you shop options across carriers based on your health, age, and goals.
Don’t Overlook Long-Term Care & Taxes
A health event can derail even the best plan. The goal is not to predict the future perfectly—it’s to reduce the damage if a high-cost scenario happens. Long-term care planning is often ignored until it’s too late, and taxes are often ignored until the first large distribution surprises you.
If long-term care is a concern (for you or your parents), start by understanding solutions that preserve income and reduce taxes where appropriate. Many families compare traditional coverage to hybrid approaches depending on whether they prioritize pure protection, asset preservation, legacy planning, or premium flexibility. These resources can help you navigate your next step: Tax Benefits of Long-Term Care Insurance, Partnership-Qualified LTC, LTC with Return of Premium, and Affordable Hybrid LTC Policies.
Income Protection: Your Ability to Earn Is Often Your Biggest Asset
Many people insure their home, car, and phone before they insure the thing that pays for everything: their income. Disability coverage becomes especially important during career changes, business launches, salary increases, and family milestones. A planning meeting should confirm whether your current coverage is portable, whether it’s enough, and what happens if you cannot work for months—or years.
Profession-specific disability planning matters because definitions of disability and benefit structure can dramatically affect outcomes. If your income is high or your job requires specialized skills, you typically want coverage designed to protect your specific occupation. Start here if you want to explore deeper: High-Income Disability Insurance. If you’re a business owner, revisit Business Overhead Disability Insurance to see how it can keep the business stable during a medical event.
What to Bring to Your First Planning Review
A productive meeting doesn’t require a binder full of documents—but it does require enough information to see the full picture. The fastest way to get value from a planning review is to bring (or list) the basics: current income sources, retirement account balances, insurance policies, debt payments, and any upcoming life transitions you’re anticipating.
If retirement is within ten years, also bring a rough estimate of monthly expenses. If you don’t have an exact number, an estimate is fine. The goal is to identify what spending must be covered no matter what, and what spending is optional. That single distinction drives better decisions around guaranteed income planning.
If you have life insurance, bring policy type and face amount. If you have disability coverage, bring the monthly benefit amount and whether it’s employer-provided. If you have an annuity, bring the contract type and whether it includes an income rider. If you don’t know, that’s fine—we can help you interpret it. The point is to avoid guessing, because the fine print matters more than the marketing name.
What to Ask a Financial Advisor in the First Meeting
Most people ask: “What do you recommend?” A better first question is: “How do you make recommendations?” A good advisor should explain how they evaluate your goals, risk tolerance, timeline, and tax situation. They should also be clear about what they do and do not manage. That clarity prevents misunderstandings later.
Other useful questions include: What are the biggest risks you see in my plan right now? What decisions are time-sensitive? Where am I overexposed to market risk? Where am I underinsured? If I retire earlier than expected, what breaks? If taxes rise, what breaks? If I need long-term care, what breaks? Those questions quickly separate “generic advice” from a plan that’s built for real life.
Finally, ask what a review cadence should look like. Many people don’t need constant meetings. They need a good plan and consistent check-ins at the right times—especially after major life events like the ones listed above.
Lifetime Income Calculator
If your plan includes retirement income, it helps to see what different premiums and ages can produce in guaranteed lifetime income options. Use the calculator below to explore scenarios, then we can help compare strategies that align with your timeline and goals.
Compare Today’s Best Annuity Rates
If one of your life events involves retirement timing, income planning, or protecting principal, it helps to compare conservative options side-by-side. Use the links below to review competitive rates and structures from top carriers.
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If a life event is forcing decisions about income, taxes, insurance, or retirement timing, we’ll help you identify gaps and map the next best step—without guesswork.
How Often Should You Meet With a Financial Advisor?
For most people, the right cadence is not monthly meetings—it’s structured check-ins based on your life stage and the complexity of your finances. During stable periods, an annual review can be enough. During transition periods, you may need a few meetings close together so decisions don’t drift and deadlines don’t sneak up.
If you’re working and building, reviews often focus on contributions, protection, and tax diversification. If you’re within ten years of retirement, reviews tend to shift toward income strategy, risk reduction, and healthcare planning. If you’re retired, reviews become about distribution planning, tax efficiency, and making sure your plan still works when markets, rates, and life inevitably change.
The simplest rule is this: whenever a life event changes your cash flow, taxes, responsibilities, or timeline, it’s time to meet. That includes good changes (raises, inheritance, business success) and hard changes (health issues, divorce, layoffs). The goal is to keep your plan aligned with reality, not with the version of life you expected five years ago.
Common Mistakes People Make When They Wait Too Long
Waiting too long often turns a small decision into a costly one. People miss employer benefit windows, lose portability options on coverage, fail to update beneficiaries, or lock in a retirement date without testing how income will actually work. Sometimes the biggest mistake is simply failing to create a predictable baseline, then being forced to react to a market downturn at the worst possible time.
Another common issue is making tax decisions without understanding the downstream effect. A rollover decision, an inheritance distribution, or a large withdrawal might look harmless in the moment, but the tax impact can last for years. That’s why we encourage clients to treat major transitions like a “planning event” and schedule a review before decisions become permanent.
Even a brief planning review can prevent the most common problems: overconcentration, underinsurance, unnecessary taxes, and poorly timed withdrawals. The goal is not to overcomplicate your life—it’s to make the big decisions simpler and more confident.
Related Topics to Explore
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FAQs: When to Meet with a Financial Advisor
How often should I meet with a financial advisor?
At least once per year, plus anytime a major life event occurs—job change, marriage/divorce, inheritance, market shock, or within 5–10 years of retirement. Use our Pre-Retirement Checklist if you’re approaching retirement.
What life events should trigger a review?
New job or compensation, starting a business, buying/selling a home, marriage or divorce, new child, inheritance, health changes, or caring for parents. If retirement is near, compare guaranteed income options on Current Annuity Rates.
Is the 4% rule still reliable?
It’s a starting point, not a plan. Longevity, inflation, and early-retirement market drops can make it risky. Learn more in What Is the 4% Rule? and compare lifetime income options.
When should I talk to an advisor about retirement income?
Five to ten years before retirement. That’s the window to layer Social Security timing, pensions, and guaranteed income. See How Much Does a $1 Million Annuity Pay?
What should I bring to my first meeting?
Recent statements (investment, bank, annuities), tax return, insurance policies, estate docs, and a list of goals and concerns. If you own annuities, bring the contracts so we can review income riders and surrender terms.
Do I need an advisor if I’m still working?
Yes—benefits elections, rollovers, disability coverage, and tax planning are most impactful during high-earning years. Explore income protection options like High-Income Disability Insurance.
Should I meet after receiving an inheritance?
Absolutely. Coordinate taxes, titling, and risk. Many clients earmark a portion for guaranteed income using annuities—compare options on Current Annuity Rates.
How do long-term care needs affect the timing?
Discuss LTC earlier than you think. Evaluate traditional LTCI, hybrid LTC policies, and Partnership-Qualified LTC while you’re still healthy.
What if markets are volatile—should I wait?
No. Volatility is exactly when to review risk, cash reserves, and income safety nets. If needed, carve out guaranteed income so essential expenses are covered regardless of markets.
Can an advisor help with divorce and annuities?
Yes. Annuities have riders, surrender periods, and tax rules. Start with How Annuities Are Divided in Divorce and What Happens to Your Annuity in a Divorce?
How do I know if I’m saving enough?
Stress-test your plan against longevity and inflation. Use our annuity income series—e.g., $500k, $750k, and $1M—to benchmark lifetime income.
How do I get started?
Request a review on our Contact Page or call 800-533-5969. If you’re retirement-focused, begin with the Pre-Retirement Checklist.
About the Author:
Jason Stolz, CLTC, CRPC and Chief Underwriter at Diversified Insurance Brokers, is a senior insurance and retirement professional with more than two decades of real-world experience helping individuals, families, and business owners protect their income, assets, and long-term financial stability. As a long-time partner of the nationally licensed independent agency Diversified Insurance Brokers, Jason provides trusted guidance across multiple specialties—including fixed and indexed annuities, long-term care planning, personal and business disability insurance, life insurance solutions, and short-term health coverage. Diversified Insurance Brokers maintains active contracts with over 100 highly rated insurance carriers, ensuring clients have access to a broad and competitive marketplace.
His practical, education-first approach has earned recognition in publications such as VoyageATL, highlighting his commitment to financial clarity and client-focused planning. Drawing on deep product knowledge and years of hands-on field experience, Jason helps clients evaluate carriers, compare strategies, and build retirement and protection plans that are both secure and cost-efficient.
