Imagine sitting at your desk, reviewing your retirement portfolio that you've carefully built over decades.
Despite having over $1 million in assets, you can't shake that nagging question: "Am I really ready for retirement?" If this sounds familiar, you're in good company.
A recent Harvard Business Review study revealed that 28% of investors surveyed experience depression and significant anxiety about their retirement readiness – and it's not just about the numbers.
Here's the thing: retirement planning for high-net-worth individuals isn't just a matter of having "enough" saved. It's about orchestrating a symphony of investment strategies, tax planning, healthcare considerations, and lifestyle choices.
Think of it like planning an extended vacation – except this one could last 30 years or more!
You need to consider everything from which accounts to tap first (hello, tax efficiency!) to how you'll maintain your lifestyle while preserving your legacy for future generations.
Whether you're five years from retirement or already enjoying your post-career life, asking the right questions now can make all the difference between a retirement that's merely comfortable and one that's truly fulfilling. We've compiled 25 critical questions that our high-net-worth clients consistently find valuable in their retirement planning journey.
Need additional help with your retirement planning? Be sure to download our free retirement cheat sheets to potentially help you save money, reduce taxes, and optimize your portfolio for retirement.
Key Takeaways: Retirement Planning Questions
Think of retirement planning like building your dream house – you need a solid foundation (investments), good insulation (tax strategy), and proper protection (healthcare planning)
Smart tax planning isn't just for your working years – it's actually more critical in retirement
Your retirement strategy should be as unique as your fingerprint, reflecting your personal goals and lifestyle
Don't let market swings keep you up at night – a well-designed portfolio can help you sleep better
Healthcare planning isn't just about Medicare – it's about protecting the wealth you've worked so hard to build
Investment and Portfolio Questions
1. Is my portfolio properly diversified for retirement?
Let’s be honest – many successful professionals end up with a lot of eggs in one basket. Maybe it’s company stock from years of equity compensation, or perhaps it’s that real estate investment that’s done really well. But here’s the reality check: retirement isn’t the time for concentration risk. Think of diversification like a well-balanced meal – you need different types of nutrients (or in this case, investments) to stay healthy within your investment portfolio.
💡 Pro Tip: Ever notice how some investments zig while others zag? That’s exactly what we’re looking for! Check how your investments work together during different market conditions – it’s like having both an umbrella and sunscreen in your bag. If all of your investments are going up (or down) at the same time, you are likely doing something wrong.
2. What's my optimal asset allocation given my risk tolerance?
Remember that feeling in your stomach during the last market downturn? That's your real risk tolerance talking! Your asset allocation, or your mix of stocks, bonds, cash, and other assets should help you sleep at night while still keeping pace with inflation. It's like adjusting the thermostat – you want it just right for your comfort level.
3. How will Required Minimum Distributions (RMDs) impact my investment strategy?
Think of RMDs as Uncle Sam’s way of saying, “Hey, remember that tax break you got years ago? Time to pay up!” Withdrawals from tax-deferred accounts, such as 401(k)s and traditional IRAs, are taxed as ordinary income. As your 72nd birthday approaches (that’s the magic RMD age), you’ll need a game plan.
“I often see clients caught off guard by their first RMD,” notes Scott Hurt, CFP®, CPA at Covenant Wealth Advisors in Richmond, VA. “It’s like getting an unexpected dinner guest – you need to prepare for it!”
Tax Planning Questions to ask
4. How can I optimize my tax strategy in retirement?
Think of tax planning in retirement like playing chess – each move matters! Having different types of accounts (traditional IRAs, Roth IRAs, and regular investment accounts) gives you the flexibility to pull from different “tax buckets” based on your needs.
It’s like having multiple faucets to control your water flow – you can adjust based on the situation.
For personalized tax advice, consider consulting a CERTIFIED FINANCIAL PLANNER™ (CFP®) who specializes in tax planning in retirement.
5. Should I consider Roth conversions?
Here's a fun way to think about Roth conversions: it's like paying your taxes during a sale. If you're in a lower tax bracket now than you expect to be later (maybe because you're between careers or recently retired), converting some traditional IRA money to a Roth could be smart. It's like buying your favorite wine when it's on discount!
💡 Pro Tip: Don't try to convert everything at once – it's like eating an entire cake in one sitting (not recommended!). Consider spacing out your conversions over several years to keep your tax bill manageable.
6. How will state taxes affect my retirement planning?
Location, location, location! It's not just a real estate mantra. Where you plant your retirement flag can have a huge impact on your tax bill. Some states roll out the red carpet for retirees with tax breaks, while others... not so much. We help clients run the numbers on different scenarios – think of it as comparison shopping for your tax home.
Income Planning Questions to Ask
7. What's my optimal retirement income withdrawal strategy?
Creating retirement income is like conducting an orchestra – you want all your instruments (income sources) playing in harmony to ensure a steady annual income.
Which accounts you tap first and the order of your withdrawals matters a great deal.
“We help our clients develop what we call a ‘retirement paycheck’,” explains Matt Brennan, CFP® at Covenant Wealth Advisors in Reston, VA. “It’s about making your investments sing together to create reliable, tax-efficient income.”
8. How should Social Security fit into your income plan?
Think of Social Security as the backup singer in your retirement band – it might not be the lead, but it plays an important supporting role. Reaching full retirement age allows you to earn more without reducing your benefits, which is crucial for maximizing your monthly payouts.
The timing of when you start taking benefits can make a difference of hundreds of thousands of dollars over your lifetime. It’s like choosing when to cash in a winning lottery ticket – timing matters!
9. Should I consider annuities as part of my retirement strategy?
Let's talk about everyone's favorite dinner party topic – annuities! (Just kidding, but stick with me here.) Think of annuities like hiring a retirement "employer" who promises to send you a paycheck no matter how long you live.
They can be useful tools for some situations, but like that fancy kitchen gadget you bought last year, you need to be sure you'll actually use what you're paying for.
We've seen plenty of bad annuities and they aren't for everyone. But, they can be great in certain situations. It just depends.
Healthcare and Insurance Planning Questions to ask
10. How should I plan for healthcare costs in retirement?
Remember when a doctor’s visit cost you a $20 copay and that was it? Those were the days! Healthcare in retirement is more like a complex puzzle with pieces called Medicare Parts A, B, D, and don’t forget those Medigap policies! Planning for healthcare costs, including purchasing health insurance, is like saving for a second house – it’s a significant expense that deserves its own strategy.
💡 Pro Tip: Think of an HSA as a “healthcare piggy bank” with tax superpowers. If you can contribute now, your future self will thank you with triple tax advantages!
11. What role should long-term care insurance play in my plan?
Nobody likes to think about needing help with daily activities, but it’s like buying travel insurance for your retirement journey – you hope you won’t need it, but you’ll be glad to have it if you do. Consider your options:
Traditional long-term care insurance (the classic approach)
Hybrid policies (getting something back even if you don’t need care)
Self-insurance (if your nest egg is large enough)
Additionally, it's crucial to plan for purchasing health insurance to cover long-term care costs, especially since employer-sponsored plans may not be available and Medicare eligibility starts at age 65.
Estate and Legacy Questions to Ask
12. How can I minimize estate taxes?
Estate planning isn’t just for the British aristocracy anymore! If you’ve built substantial wealth, managing your financial resources effectively can prevent Uncle Sam from becoming your primary heir – unless you plan ahead.
Think of estate planning like playing chess – you need to think several moves ahead and position your pieces (assets) strategically.
13. What's the best way to transfer wealth to the next generation?
Remember teaching your kids to ride a bike? Transferring wealth requires similar patience and careful guidance in managing financial resources.
Consider these strategies:
Annual gifting (like giving your kids a financial “allowance”)
529 plans (because education is the gift that keeps on giving)
Trust structures (think of them as financial “training wheels”)
Family limited partnerships (the family business 2.0)
💡 Pro Tip: Family meetings about money don’t have to feel like episodes of Succession. Regular, open discussions can help ensure everyone’s on the same page.
Lifestyle and Personal Consideration Questions to Ask
14. How will my spending patterns change in retirement?
Spoiler alert: Your spending in retirement probably won’t look like your parent’s retirement budget, as personal finance is highly individualized. Maybe you’ll trade your work wardrobe budget for travel expenses, or your commuting costs for golf club memberships.
We help clients create what we like to call a “lifestyle blueprint” – because retirement should be about living, not just existing.
15. Should I downsize or maintain multiple homes?
Ah, the great housing debate in personal finance! Should you keep the family home where you can host holiday gatherings, downsize to that trendy condo downtown, or maybe split your time between two locations?
Consider:
Will you really use that guest room more than twice a year?
Does maintaining a large home spark joy or anxiety?
Could that home equity be better used elsewhere in your retirement plan?
16. What role should charitable giving play in your retirement plan?
Want to make a difference while saving on taxes? (Now that's what we call a win-win!) Charitable giving in retirement can be like having your cake and eating it too.
Consider these smart giving strategies:
Qualified Charitable Distributions from your IRA (skip the tax bill entirely!)
Donor-Advised Funds (think of them as your personal charitable savings account)
Charitable Remainder Trusts (the gift that keeps on giving – to you and your favorite causes)
💡 Pro Tip: Time your charitable giving with your RMDs for maximum tax efficiency – it's like getting a bonus tax break!
Risk Management Questions to Ask
17. How should I protect against market volatility?
Financial challenges, such as market volatility, are like New England weather – if you don’t like it, just wait a minute! But seriously, protecting your nest egg requires more than just crossing your fingers.
Consider:
Building a “weather-resistant” portfolio with different types of investments
Keeping a cash cushion for rocky times (your financial umbrella, if you will)
Regular portfolio check-ups (like taking your financial temperature)
18. What insurance coverage should I maintain in retirement?
Financial challenges in retirement can be daunting, but having the right insurance coverage is like having a good security system – you hope you’ll never need it, but you’ll sleep better knowing it’s there. Review these key areas:
Life insurance (does your coverage match your current needs?)
Property protection (because stuff happens)
Umbrella liability coverage (for those “just in case” moments)
19. How can I protect against inflation risk?
Remember when movies cost a nickel? Okay, maybe not, but you get the point! Inflation is like a stealth tax that can slowly eat away at your purchasing power. Think of protecting against inflation like planting a garden – you need different types of investments that can grow along with rising prices.
20. What's my plan for cognitive decline?
Let's talk about something nobody wants to talk about – but everyone should. Planning for potential cognitive decline is like creating an instruction manual for your financial life. You need to:
Set up a "financial fire drill" with trusted family members
Create clear powers of attorney (your financial backup quarterback)
Document your wishes while you're sharp as a tack
21. How should I prepare for potential tax law changes?
Tax laws change about as often as smartphone models – which is to say, frequently! Building flexibility into your plan is like having an adjustable mortgage rate – but in a good way. We help clients create strategies that can adapt to whatever Congress throws our way.
Technology and Communication Questions to Ask
22. What technology should I leverage in retirement?
A financial advisor can help you leverage technology to make retirement life easier. Consider tools for:
Tracking expenses (because spreadsheets are so last century)
Monitoring investments (without becoming a day trader)
Managing healthcare appointments
Staying connected with family (grandkid video calls for the win!)
23. How should I communicate my financial plans with family?
Think of this as creating your family’s financial user manual with the help of a financial advisor. Clear communication can prevent future headaches and ensure everyone understands your wishes.
24. What's my plan for staying mentally and physically active?
Retirement isn't about sitting in a rocking chair (unless that's your thing – no judgment here!). Budget for activities that keep you sharp and healthy:
Gym memberships or personal training
Educational courses or workshops
Travel and exploration
Hobbies and social activities
25. How often should I review my retirement plan?
Think of your retirement plan like your car – it needs regular maintenance, not just emergency repairs. Schedule check-ups to review:
Whether your investments still match your goals
If your income plan is working as expected
Whether tax law changes affect your strategy
If your estate plan still reflects your wishes
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FAQs
Q: When should I start taking Social Security benefits?
A: Timing Social Security is like playing poker – you need to know when to hold ‘em and when to fold ‘em! For many high-net-worth folks, waiting until 70 makes sense because of the guaranteed 8% annual increase in benefits. But everyone’s situation is unique.
Q: How often should I review my retirement plan?
A: Think of your retirement plan like your favorite streaming show – you don’t want to miss any important episodes! We recommend a thorough review at least annually, plus “special episodes” when big life changes happen or markets get especially dramatic.
Q: What’s the best way to prepare for market volatility in retirement?
A: Remember the old saying about not putting all your eggs in one basket? Well, we like to add that you should also know which eggs you’ll need for breakfast tomorrow! Build a retirement strategy that includes both growth potential and protection for your retirement savings.
Conclusion
Whew! We’ve covered a lot of ground here, haven’t we? But here’s the thing about retirement plans – it’s not about having all the answers right now. It’s about asking the right questions and building a plan that can grow and adapt with you.
At Covenant Wealth Advisors, we’ve helped hundreds of high-net-worth individuals turn these questions into personalized strategies. Whether you’re still in the “gathering information” phase or ready to put rubber to the road, we’re here to help you navigate your retirement journey.
Remember, retirement planning isn’t a one-and-done task – it’s more like tending a garden. The more attention you give it, the better it grows. And just like a garden, the best time to start planning was yesterday. The second best time? Today.
Would you like our help designing a personalized plan for your retirement? Contact us today for a free retirement assessment.
About the author:
CEO and Senior Financial Advisor
Mark is the CEO of Covenant Wealth Advisors and a Senior Financial Advisor helping individuals age 50+ plan, invest, and enjoy retirement comfortably. Forbes nominated Mark as a Best-In-State Wealth Advisor* and he has been featured in the New York Times, Barron's, Forbes, and Kiplinger Magazine.
Disclosures: Covenant Wealth Advisors is a registered investment advisor with offices in Richmond, Reston, and Williamsburg, VA. Registration of an investment advisor does not imply a certain level of skill or training. Past performance is no guarantee of future returns. Investing involves risk and possible loss of principal capital. The views and opinions expressed in this content are as of the date of the posting, are subject to change based on market and other conditions. This content contains certain statements that may be deemed forward-looking statements. Please note that any such statements are not guarantees of any future performance and actual results or developments may differ materially from those projected. Please note that nothing in this content should be construed as an offer to sell or the solicitation of an offer to purchase an interest in any security or separate account. Nothing is intended to be, and you should not consider anything to be, investment, accounting, tax, or legal advice. If you would like accounting, tax, or legal advice, you should consult with your own accountants or attorneys regarding your individual circumstances and needs. This article was written and edited by a CERTIFIED FINANCIAL PLANNER™ professional with the assistance of AI. No advice may be rendered by Covenant Wealth Advisors unless a client service agreement is in place. Hypothetical examples are fictitious and are only used to illustrate a specific point of view. Diversification does not guarantee against risk of loss. While this guide attempts to be as comprehensive as possible but no article can cover all aspects of retirement planning. Be sure to consult an advisor for comprehensive advice.