If you’re a few years away from stepping back from your career, you may be asking yourself: “Am I really ready?” Not just financially, but in all the other ways that matter.
For many breadwinner women, retirement has been a date on a planning page for years. But as that date gets closer, the questions get more specific. Can I actually afford to stop? What happens to my health insurance? Should I sell the house? And what will I do with my days after decades of being needed at work?
Retiring isn’t as simple as picking a date and handing in your resignation. Your vision for this next chapter is likely completely different from anyone else’s, and planning for it is your chance to curate the life you want. For me, that means continuing to work for as long as I can while building more “life” into my work along the way. I now split my time between the U.S. and France, and thanks to a great team and a virtual client base, I can keep serving clients while spending time in places I truly love. That’s why our team treats retirement as a process, not a single event. For the breadwinner women we work with, taking time to define that vision and map out how to get there can help make this next chapter one of fulfillment and purpose, rather than the end of it.
October is National Retirement Security Month, making it a good time to walk through what the process can look like. Use this pre-retirement checklist as a guide for the years, months, and moments leading up to your retirement date and those right after.
Years Out: Set a Target Retirement Date and Build Toward It
Every retirement plan starts with a goal. At WealthChoice, our team works with clients to set an ideal target date to have the option to stop earning. The goal isn’t to force a finish line. It’s to build enough flexibility that when the day comes, stepping away is a choice.
During these years, the focus is on saving, investing, and adjusting the plan as life changes. Promotions, equity compensation, kids leaving home, caring for parents. All of it shapes whether that target date still makes sense.
12 to 18 Months Out: Confirm Your Retirement Date Still Fits
This is where the pre-retirement checklist really begins. About 12 to 18 months before your target date, it’s worth pausing to ask two questions.
Is the date still realistic? Revisit your projections with current numbers, including your portfolio, expected spending, and income sources.
Is the date still what you want? This one can be harder. Many successful women have been so focused on their careers that there hasn’t been much room to build a life outside of work. That’s not a reason to keep working, but it’s a common reason people do. Before committing to a date, it helps to picture an ordinary Tuesday in retirement. Where will your sense of purpose come from? Who will you spend time with? What have you been putting off?
Checklist:
- Reflect on your emotional readiness for the next chapter
- Schedule a dedicated pre-retirement meeting with your financial advisor
- Review whether your target date still works on paper
Building Your Retirement Transition Plan
Once the date is confirmed, the next step is turning it into a timeline of action items: what needs to happen, when it needs to happen, and who is responsible for each step. Here are some of the key areas to cover.
Healthcare coverage before 65
Medicare eligibility generally begins at 65. If you plan to retire earlier, you’ll need a way to bridge that coverage gap. Options may include COBRA coverage through your former employer, a spouse’s plan, or a policy through the ACA marketplace. Each comes with different costs and timing, so this deserves attention well before your last day. The good news is you don’t have to sort through it alone. WealthChoice has trusted resources who specialize in healthcare solutions for people in the pre-Medicare years, and we’re happy to connect you with them as part of your planning.
Your home
Do you sell and buy something smaller with cash? Keep the mortgage? Move to another state, or even another country? Rent? There’s no universal answer, but each choice affects cash flow, taxes, and flexibility. It’s important to consider things like state tax differences, proximity to family, and how long you plan to stay. We have a number of clients planning to retire abroad, drawn by the potential for a lower cost of living and a change of lifestyle. Whatever direction you’re leaning, we suggest renting first to test it out before a wholesale move, especially if you’re considering a new neighborhood, state, or country.
Gifts and family commitments
If you plan to help children, nieces, or nephews with education, a first home, or a head start, it may make sense to carve those dollars out of your retirement assets now. That way, your income plan reflects what’s truly available to you.
Taxes in your final working year
Your last year of work can come with surprises, like a special bonus, a large payout of unused PTO, or vesting equity compensation. These can push your income higher right before it drops. Planning ahead may help you manage the tax impact.
Employer benefits
Review what happens to your life insurance, disability coverage, deferred compensation, HSA, and any unvested equity when you leave. Some employers allow you to keep life insurance or other benefits after you retire, which may help you maintain coverage at a lower cost than buying it on your own. It’s worth comparing these options before your last day, since some decisions have short deadlines.
Retirement Day: Coordinate the Moving Pieces
When the day arrives, there’s coordination involved. This often includes:
- Rolling over 401(k) and other employer retirement accounts
- Opening or restructuring investment accounts to support your income plan
- Connecting with outside professionals, such as estate attorneys or insurance specialists
- Working with your CPA and financial planner on the year’s tax picture
A note on rollovers: timing and account type matter. For example, some employer plans allow penalty-free withdrawals if you leave your job in or after the year you turn 55, a feature that may no longer apply once those funds are rolled into an IRA. It’s worth reviewing before any money moves.
After Retirement: A Different Kind of Financial Planning
Retirement planning doesn’t end once you retire. It changes. Instead of saving and growing, the focus shifts toward generating reliable income, preserving principal, and helping you live the life you’ve worked so hard for.
As WealthChoice founder Bridget Venus Grimes puts it, “I’d venture to say as a planner, this is harder work for us than helping clients save and invest to get to this point.”
Checklist:
- Confirm your income strategy, including how much you’ll draw from your portfolio and when
- Look for tax planning opportunities. For many retirees, the years between leaving work and starting Social Security or required minimum distributions can be lower-income years. Some use this window to begin Roth conversions, often starting the year after they stop earning, in coordination with their CPA.
- Keep checking in. Our team meets with retired clients at least twice a year to review their income strategy, portfolio, tax opportunities, and whether the plan remains on track.
Your Pre-Retirement Checklist at a Glance
- Years out: Set a target retirement date and build your plan around it
- 12 to 18 months out: Confirm the date is still realistic and still what you want
- Transition planning: Map out healthcare, housing, family gifts, taxes, and employer benefits
- Retirement: Coordinate rollovers, accounts, and outside professionals
- After retirement: Review income, taxes, and your plan at least twice a year
You’ve Worked Hard for This Next Chapter
A smooth transition into retirement rarely happens by accident. It comes from starting early, asking the hard questions (financial and emotional), and knowing exactly what needs to happen at each stage. This pre-retirement checklist is a starting point, but every situation is different, and the right plan depends on your goals, your timeline, and the life you want to build next.
If you’re a few years from retirement and want a clearer picture of whether your target date is truly within reach, we invite you to book a complimentary consultation with our team. Let’s help you step into your next chapter with confidence.
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