By Jamie Bosse, CFP®, RFC, CCFC
A relaxing, fulfilling retirement doesn’t happen by chance. It takes years of careful retirement planning to get there. If you are like many of the people I work with, though, you may already be worn out by the sheer number of choices in front of you.
When the list never seems to end, picking the right option starts to feel impossible. I start by sorting retirement decisions by age, because the tax code and Medicare both run on birthdays. I use a framework with my clients that puts the decisions in order instead of piling them up.
What Is the Retirement Decision Roadmap?
Think of retirement planning as a roadmap, not a checklist. You don’t need to make every decision at once. Some decisions belong on the road ahead, some need your attention now, and others can wait until you get closer.
I group these decisions into three levels based on how much attention they deserve right now.
Level 1: Decisions with deadlines. Medicare enrollment and required minimum distributions live here. Miss the date, and it costs you money.
Level 2: Windows of opportunity. Catch-up contributions and Roth conversions belong here, along with the timing of your Social Security claim. Each one stays available for a limited stretch.
Level 3: Decisions you can revisit. How much you spend, where you live, and how you spend your time. These carry real consequences, and you can review them as your circumstances change.
Once you know which level a decision belongs to, the list stops feeling like one long emergency.
Level 1: Decisions With Deadlines
These come with a penalty or an unexpected bill attached if the date passes without action.
Medicare enrollment. For most people, Medicare eligibility begins at 65, though it can begin earlier for someone with a qualifying disability or illness. What you do at that point depends on your employer. If you or your spouse are covered by a group health plan based on current employment and the employer has fewer than 20 employees, Medicare generally pays your claims first, and postponing Part B can leave you owing bills your employer plan expects Medicare to cover. At companies with 20 or more employees, the group plan usually pays first, and you can often delay Part B without a late enrollment penalty. Confirm which situation applies to you with your benefits administrator before your 65th birthday rather than after.
Required minimum distributions. This is when you must begin taking money out of traditional retirement accounts, and your birth year decides which year applies:
- Born 1951–1959: RMD age is 73
- Born 1960 or later: RMD age is 75
These distributions do not happen automatically; you must proactively withdraw the funds yourself, and missing a deadline triggers IRS penalties. Whether you need the money that year or not, taking the distribution is required. This is precisely why working with an advisor is so valuable: we oversee the timing, calculate the precise amount, and arrange tax withholding ahead of time to help keep your strategy on track and work to avoid unnecessary penalties.
Level 2: Windows of Opportunity
These decisions stay available for a limited time, and the value depends on using the right stretch.
Your 50s. This is an important decade for making meaningful changes to your retirement plan. If you wish you had saved more in earlier years, catch-up contributions start at 50 and give you room to close some of that gap.
Ages 60 to 63. These four years offer one of the most valuable retirement savings opportunities available to employees. In 2026, savers who turn 60 through 63 by December 31 can add $11,250 in catch-up contributions to a 401(k), 403(b), or governmental 457(b) plan. That amount replaces the standard $8,000 catch-up rather than adding to it, and it comes on top of the $24,500 base limit for a total of $35,750. Your employer’s plan has to offer the feature, so confirm it with your benefits contact. The year you turn 64, the limit reverts to the standard catch-up amount.
Beginning in 2026, if your Social Security wages from that same employer topped $150,000 last year, your catch-up dollars now must go into the Roth side of the plan instead of the pre-tax side. Your base $24,500 can still go in pre-tax, and only the catch-up portion is affected. That $150,000 test counts vested stock compensation along with salary and bonus, so your salary can be under $150,000 while your total for the year is over it.
Age 62 and beyond. This is when you become eligible to claim Social Security, though eligibility doesn’t mean you need to claim. You can generally delay your retirement benefit until age 70, and you should evaluate the decision based on your health, longevity expectations, spouse or survivor benefits, other income, taxes, and how much your portfolio needs to provide. Claiming at 62 permanently reduces your monthly benefit for the rest of your life, which is why the timing of this decision calls for more analysis than almost any other on this list.
The years between your last paycheck and your first required distribution. For many people, this is the best stretch to consider a Roth conversion, which means moving money from a traditional retirement account to a Roth account and paying the tax now. If you retire at 67 and your required distributions begin at 73, that leaves six years when your income is often far lower than it was during your peak earning years, and a conversion often costs less in those years. Once you satisfy the five-year holding rule and the age requirement, future growth and withdrawals from the Roth account are not taxed again. Our in-house tax team runs the numbers with your advisor first, because a conversion raises your income for the year and can raise your Medicare premiums two years later.
Level 3: Decisions You Can Revisit
These decisions still matter. What you spend in your first year of retirement is a starting point, and many of my clients adjust it after a couple of years of real expenses. Housing works the same way. A house that fits at 66 can be more than you want to keep up at 76. Paying off the mortgage early has no deadline on it either, and the answer changes with your cash flow. Because you can make these calls with better information later, they come last on the roadmap.
What if You Still Feel Stuck?
When clients feel frozen, I come back to a few things.
Many decisions can be revisited later. You can generally review and change Medicare Advantage or Part D coverage during Medicare’s annual Open Enrollment period, October 15 through December 7. Your spending can go up or down as your life changes, and a move to another state is a decision you can make at 70 as easily as at 65. Other choices are difficult or impossible to reverse, including a Social Security claim, a completed Roth conversion, and the sale of a longtime home, so those get the most analysis before you act. The year you spend deciding is a year the decision was already being made for you.
Your situation is also more specific than the guidance you find online. A 4% withdrawal rate might suit someone whose only resource is an investment account. It looks different once you add Social Security, a pension, rental income, or a health condition that will raise your costs later.
There is also a point where more research stops helping. A good decision made this year usually is better than a flawless one made three years too late. You don’t need every answer in advance. You need a way to tell which decision belongs to this year and which one can wait.
Sorting Your Retirement Decisions by Age and Urgency
Many people picture retirement as something they slide into after decades of work. Without real planning behind it, that transition is often bumpier than expected.
At CGN Advisors, we work with people in and around Manhattan, Kansas, to put these decisions in order and revisit them as the rules and your circumstances change. Our tax team works in the same office as your advisor, so we build tax planning into your retirement plan instead of handling it separately. We also work with your estate attorney so your documents line up with the rest of the plan.
To talk through which retirement decisions belong on your roadmap this year, call us at (785) 340-3434 or contact us online.
Frequently Asked Questions About Retirement Decisions by Age
At what age do I have to start taking required minimum distributions?
It depends on your birth year. Under SECURE Act 2.0 rules, individuals born from 1951 through 1959 must begin required minimum distributions at age 73, while anyone born in 1960 or later begins at age 75. Your first distribution can be delayed until April 1 of the year after you reach that age, though doing so means taking two distributions in one calendar year, which can push you into a higher tax bracket. You may also want to start before you are required to, which we cover in our guide to timing your RMDs.
When is the best time to consider a Roth conversion?
There is no single best year, though the stretch between retiring and starting required minimum distributions is often the most efficient one. If you retire at 67 and begin required distributions at 73, those six years may fall in a much lower income range than your working years did, which can make a conversion less expensive. Keep in mind that each conversion carries its own five-year holding rule, and the way that rule applies depends on your age at the time you convert. A conversion also raises your income for that year, which can raise your Medicare premiums two years later. Our in-house tax team reviews both with your advisor before anything moves.
Can I contribute more to my 401(k) between ages 60 and 63?
Yes. In 2026, savers who are 60, 61, 62, or 63 by December 31 can make a catch-up contribution of $11,250 instead of the standard $8,000. Added to the $24,500 base limit, that brings your own contributions to $35,750, separate from anything your employer puts in. Your employer’s plan must offer the feature. If your Social Security wages with that employer exceeded $150,000 in the prior year, your catch-up contributions must go into a Roth account rather than the pre-tax side of the plan. That test looks at wages reported for Social Security purposes, so vested stock compensation counts alongside salary. Whether filling that limit is the right move depends on your other goals, which we walk through in Should I Max Out My 401(k)?. The year you turn 64, the limit reverts to the standard catch-up amount.
Do I have to sign up for Medicare at 65 if I’m still working?
Not always. Whether you can delay Medicare depends on your employer’s size, your HSA status, and your Social Security timing:
- If you or your spouse have coverage through an employer with 20 or more employees, Medicare Part B can generally be delayed without a penalty, and you can enroll during a Special Enrollment Period when employment or coverage ends. If the employer has fewer than 20 employees, Medicare generally becomes your primary payer at 65, so delaying coverage can lead to insurance gaps or unexpected bills.
- Once enrolled in any part of Medicare, you can no longer contribute to a Health Savings Account (HSA). Premium-free Part A coverage is retroactive for up to six months when enrolling after 65, which can turn recent HSA contributions into penalized excess contributions.
- Receiving Social Security benefits at 65 triggers automatic enrollment in Medicare. Claiming Social Security at any later point automatically enrolls you in premium-free Part A, immediately ending your HSA contribution eligibility.
If you plan to work past 65, especially if you utilize an HSA, coordinate your Medicare and Social Security timing in advance with your benefits administrator or financial advisor. Medicare enrollment is one item on our 12-step retirement preparation checklist.
About Jamie
Jamie Bosse, CFP®, RFC, CCFC, is a Senior Advisor at CGN Advisors in Manhattan, Kansas, who specializes in helping parents in their 30s and 40s balance family life, career advancement, and financial goals. An industry veteran since 2004, she was named to the 2020 InvestmentNews “40 Under 40” list and is a passionate financial literacy advocate, authoring Money Boss Mom and the Milton the Money Savvy Pup children’s book series.
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