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If you’ve saved a million dollars or more and you’re approaching retirement, you’ve probably asked yourself this question: do I actually need a financial planner?
I’m a financial planner, and you’d probably expect me to say yes. But I don’t think the answer is that simple.
Not everybody needs a financial planner. If you can honestly check four boxes, I think you can manage your own retirement and do it well. Let’s walk through what those four boxes are, so you can run the audit on yourself.
Box 1: Do You Have the Skill?
If you’ve saved $1 million or more in a 401(k) or IRA, you clearly have some skill already. It takes discipline and emotional regulation to build that kind of nest egg, especially as you get closer to retirement, when market swings translate into bigger dollar losses.
But it can be a bit more complex than just accumulating $1million+ in an account. The skills that got you to retirement aren’t the same skills you need once you’re in it.
While you’re working, the rules are fairly stable. You save, you contribute, you let the account grow. Once you retire, nearly everything shifts.
- How you collect income changes.
- How that income gets taxed changes.
- Your flexibility around withdrawals changes.
- You go from thirty or forty years of doing it one way to needing a completely different playbook.
This is where a lot of retirees get caught off guard. Take a taxable IRA withdrawal without thinking it through, and you could push yourself into a higher tax bracket, cause more of your Social Security benefit to be taxed, or trigger a higher Medicare premium surcharge two years down the road through IRMAA.
One withdrawal decision can ripple across your income, your taxes, and your investments all at once. I think of this as a triangle: move one corner, and the other two move with it.
The rules also change more often than people expect. The One Big Beautiful Bill, passed in July 2025, introduced an enhanced senior deduction of up to $6,000 for eligible retirees. Do a Roth conversion that’s a little too large, and you can phase yourself out of that deduction. And it’s only available for a limited number of years unless Congress extends it. Staying current with changes like this is now part of the skill set retirement demands.
The question to ask yourself
Do you understand how your income, taxes, and investments interact with each other, and are you staying current as the rules change?
Box 2: Do You Have the Will?
This one is harder to measure, but it matters just as much.
Think back to 2008. The market correction wiped out a significant amount of wealth for people who were retired or close to it. It wasn’t just the drop itself. It was the fear that came with it. If you had sold everything and moved to cash at the bottom, you would have missed the recovery that followed.
The same test showed up again during the COVID crash in 2020 and the 2022 downturn. In both cases, retirees who held steady and avoided panic selling came out ahead. Some were even able to use the dip for tax planning moves like Roth conversions at lower valuations.
The question to ask yourself
When the market drops 20% in a matter of weeks, can you sit still without making a move you’ll regret?
Box 3: Do You Have the Time?
Managing your own retirement finances is a bit like gardening. If you enjoy it, you can grow your own produce and skip a lot of grocery store trips. But gardening only pays off if you put in the time, week after week, season after season.
Retirement finances work the same way. If you’re willing to invest the hours to learn the rules, monitor your accounts, and keep re-educating yourself as things change, you probably don’t need to hire anyone.
But if you’d rather spend that time with your grandkids, traveling, or doing literally anything else, someone still has to do the work. That’s usually where a financial planner comes in.
The question to ask yourself
Is managing your own retirement income the way you actually want to spend your time?
Box 4: Do You Have a Succession Plan?
This is the box I think gets overlooked the most, and it might be the most important one.
What happens if you’re suddenly unable to manage your own finances, whether from a health event or worse? Your financial plan is only as good as what happens after you’re no longer the one running it. At that point, it falls to whoever is left, a surviving spouse, adult children, whoever it may be, to answer the same three questions: do they have the skill, the will, and the time?
If the answer for them is no, that’s a real reason to have a professional in place now, before the transition happens under stress.
I see this play out often with surviving spouses. They move from married filing jointly to single tax brackets, sometimes called the widow’s penalty, and the tax hit can be significant if there’s no plan in place to soften it.
The question to ask yourself
If something happened to you tomorrow, does the person left behind have what they need to carry the plan forward?
Running the Audit
If you can honestly say yes to all four, skill, will, time, and a succession plan, I don’t think you need to hire a financial planner. You’re set up to handle your own retirement, and you can do it well.
If you’re struggling with one or more of these, it’s worth exploring what kind of help fits. Not all financial planners work the same way. Some charge hourly. Some work on a flat fee. Some charge based on assets under management. Some sell products. The right fit depends on which of the four boxes you’re missing and what kind of support actually closes that gap.
Actionable Steps:
- Test your skill honestly. Pull up your last IRA withdrawal or planned Roth conversion and ask whether you fully understood its effect on your tax bracket, your Social Security taxation, and your Medicare premiums two years out.
- Test your will with a real number. Ask yourself how you’d react, not in theory but specifically, if your portfolio dropped 20% in six weeks the way it did in 2020.
- Block real time on the calendar. If you can’t name the last three hours you spent studying retirement tax rules, time may be your weak spot.
- Write down your succession plan today. Name who takes over your financial decisions if you can’t, and make sure they know where to find your accounts, your advisors, and your intentions.
If you’re approaching retirement or already there and want help building the structure that supports real financial peace, we can help. At Hyperion Financial, we work with our clients to build plans that reflect their actual lives – not just their balance sheets. Because the numbers matter, but the peace matters more. Click Here to schedule a conversation.