Now, that your retirement date is quickly approaching. You’ve got your financial team lined up (Financial Advisor, Tax Pro (CPA), Estate Attorney (Lawyer), the whole crew.
Are you sure you’re asking the right questions?
Could your dream retirement be at risk because your team’s still playing an old pre-retirement game?
Let’s see if we can fix that.
When retirement begins, the game changes.
- Old retirement plans often are not good enough once you start retirement. It’s easy to miss crucial details for this new life chapter.
- The big worries begin to change. Outliving your money, surprise medical bills, overpaying taxes, or no solid income plan replace the concern of “Do I Have Enough to Retire”.
An Allianz Life study even found most of us fear running out of savings more than death! That’s why these specific questions are vital.
Your team must pivot with you. If they’re not asking the right questions for this stage, your peace of mind is at stake.
The good news? You’re the coach of your team! It’s about knowing the right questions to ask to ensure your team is on YOUR page for what you need now and later.
Let’s dive into those key questions you need to ask now!.
The Reality Check – Are We Really Ready for Retirement, Like, Right Now?
Key Question #1:
“Okay, team, looking at today’s actual numbers and some conservative future guesses, am I truly financially set for retirement? Can I keep my lifestyle, especially with inflation and healthcare costs?”
Why it’s vital: “Almost there” isn’t enough when paychecks stop. Think of a bridge that’s 90% complete – still unusable. You need a clear, stress-tested ‘yes,’ not a vague ‘you’ve saved a lot.’
Your team must show a solid income plan: Social Security, pensions, withdrawals. What are your expected costs, and how will inflation affect them over 20-30 years? Healthcare is a big one: a 2024 report flagged $413,000 for a couple’s healthcare in retirement, excluding long-term care!
You need a clear cash flow projection. They should discuss safe withdrawal rates and how your plan handles market swings. Vague answers? Red flag! Demand real figures. If there are gaps, find them NOW and discuss fixes. Honesty first!
The Portfolio Pivot – Are My Investments Set Up for Spending, Not Just Saving?
Key Question #2:
“Now that I’m in the spending phase, how have we adjusted my investments to lower risk and generate dependable income? And what’s our specific plan for managing ‘sequence-of-returns risk’?”
The game shifts from just growing money to creating income and protecting it. Aggressive growth plus withdrawals can be disastrous if markets tank early in retirement. That’s ‘sequence-of-returns risk’ – like a runner stumbling badly right out of the starting blocks; it can spoil the whole race, even if they could recover. Your portfolio must change.
Your advisor should explain how your investment mix is now more conservative but still allows for some growth against inflation. Ask about diversification, accessing cash without selling low, and review frequency. What are your safety nets for market dips? A solid answer shows a cautious, income-first approach. If they still sound like you’re 45 and growth-obsessed, that’s a warning.
The Tax Tightrope – How Do We Keep My Tax Bill as Low as Possible in Retirement?
Key Question #3:
“What’s our annual strategy to minimize taxes on all my retirement income – from Social Security, investment withdrawals, and those RMDs?”
Surprise! Taxes don’t retire when you do; they can actually get trickier! Imagine juggling different types of fruit – some are taxed now, some later, some hardly at all. You need a plan.
Your team, especially your tax pro, needs a smart withdrawal strategy. Which accounts do you tap first? Ask about Roth conversions: could paying some tax now save you more later, especially with tax laws potentially changing? Understand how your Social Security benefits will be taxed. And RMDs (Required Minimum Distributions) usually kick in at 73 – miss those, and you’re looking at hefty penalties. You want a proactive, year-round tax plan.
The Healthcare Maze – What’s Our Full Plan for Medical Bills and Possible Long-Term Care?
Key Question #4:
“Beyond Medicare, what’s our specific financial plan for all other medical expenses, and especially, how are we addressing the massive potential cost of long-term care?”
Healthcare in retirement is a big unknown. Medicare helps, but it’s not a free pass – think of it as basic car insurance; it covers some things, but you’ll likely need more for full protection. You’ve still got premiums, deductibles, co-pays, and often no coverage for dental, vision, or most long-term care.
Your team needs to help you estimate these out-of-pocket costs. And long-term care? That’s the potential budget-buster. Many retirees will need it, and it can be incredibly expensive. Ask your team about options: LTC insurance, self-funding (which needs a hefty sum), or other strategies. What you need is a clear, honest plan, not a vague ‘we’ll figure it out later.’ Address this now while you have more options.
Your Legacy Plan – Is My Estate Plan Up-to-Date and Smart for My Heirs?
Key Question #5:
“Are my will, trusts, powers of attorney, and especially my beneficiary designations totally current? Do they accurately reflect my wishes and are they structured to be tax-smart for my heirs?”
Your legacy is part of your retirement plan. These documents aren’t something you sign once and then stuff in a drawer for 20 years. Like your car, they need regular check-ups, especially if life or tax laws change. An old plan can cause real heartache and unintended consequences for your loved ones.
Your financial advisor and estate attorney should work together here. Super important: beneficiary forms on IRAs, 401(k)s, and life insurance often trump what’s in your will. Make sure they’re correct! Discuss trusts for asset protection, minimizing estate taxes, and ensuring your wishes for your legacy are crystal clear.
The Team Check-Up – How Do You Get Paid, How Do We Talk, and Are You Really on My Side?
Key Question #6:
“Can you clearly explain how you get paid? Are you fee-only, fee-based, or do you earn commissions? How often will we meet to review my plan, and what will those reviews cover? And, most importantly, will you put in writing that you are acting as my fiduciary?”
You need to know your team is truly on your side. How they’re paid is critical. Fee-only (a set fee, hourly, or a percentage of assets) typically means fewer conflicts of interest, as they aren’t earning commissions by selling you specific products. Be wary if an advisor is vague about their compensation.
Also, clarify your review schedule: How often will you formally connect, and what will those meetings entail?
And the absolute deal-breaker: Are they a fiduciary? This means they are legally and ethically bound to act in your best interest. Period. You want a clear, unequivocal ‘YES’ to this, preferably in writing. Think of it like hiring a personal trainer – you want someone focused on your fitness goals, not just selling you the most expensive supplements. Anything less than a clear fiduciary commitment is a serious red flag.
Recap
Phew! These questions are your key to unlocking vital conversations. Talks that can mean the difference between a stressful retirement and a secure one. You’re covering true financial readiness, income-focused investments, smarter tax strategies, healthcare and long-term care planning, your legacy, and how your team operates. You’re taking control!
Call to Action
So, what’s your next move? Don’t delay – schedule that meeting with your retirement team.
If you have no team, or not confident in yours? It’s time to find qualified, fiduciary advice.
Please check out other articles I’ve written on the Need for a Retirement Team and Not Going it Alone.
Got other pressing retirement questions? Pop them in the comments below!
Wrapping Up
Look, your retirement is way too important for guesswork or outdated strategies. By asking these tough, specific questions NOW, you’re building that secure, happy future you’ve worked so hard for. Take the lead, ask the questions, and walk into your retirement feeling confident and truly prepared
Thank you for taking the time to read this article.
If you would like, please leave a comment below or you can email me at www.feedback@wewaonthenet.com.
I’ve also begun a YouTube channel, www.youtube.com/@wewaonthenet where I will be discussing various retirement topics and topics I come across that I think may be of interest. Check it out!
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