Key Takeaways
- Thoughtful retirement planning incorporates a wide range of topics including income, spending, healthcare, taxes, and lifestyle priorities.
- Understanding your retirement spending needs is one of the most important steps in determining retirement readiness.
- Review all retirement income sources, including Social Security, pensions, investment accounts, and other assets.
- Healthcare planning, especially before age 65 and Medicare eligibility, can have a significant impact on retirement costs.
- A comprehensive financial plan can help determine whether your retirement goals are achievable and sustainable.
- Retirement is a qualitative decision just as much as a financial one. Having a clear vision for how you’ll spend your time is important.
A Practical Retirement Planning Checklist for Your Next Chapter
Our team at Curi Capital has retired hundreds of times.
No, not personally, but we have helped guide hundreds of clients into this exciting stage of life. Every retirement journey looks different. Some clients move south full-time for warmer weather. Others take up new hobbies, volunteer, start consulting businesses, or spend more time with children and grandchildren.
Personally, I aspire to travel abroad more and perhaps spend a year living in a new city—an idea inspired by one of our clients.
The reality is that you only get one retirement. While it’s often viewed as a financial milestone, retirement is also one of life’s biggest personal transitions. Preparing in the years immediately before retirement can help you enter this next chapter with confidence and clarity.
If retirement is on the horizon, here are several important steps to include in your pre-retirement checklist.
1. Determine Your Retirement Spending Plan
I don’t particularly like the word “budget.” It feels restrictive.
Instead, I prefer to think about retirement through the lens of a spending plan.
One of the most important retirement planning exercises is understanding how much you’ll actually spend once you’re no longer earning a paycheck. Start by evaluating your current cash flow and considering how your spending may change in retirement. While some expenses, such as commuting costs or retirement plan contributions, may disappear, others often increase.
Many retirees find themselves spending more on travel, hobbies, gifts for children and grandchildren, and experiences they’ve postponed during their working years. It’s also important to remember the larger expenses that don’t occur every month, such as property taxes, insurance premiums, home repairs, vehicle replacements, and vacations. Incorporating these costs into your retirement spending plan can provide a much more realistic picture of what your retirement lifestyle will require.
2. Understand Your Assets and Retirement Income Sources
As retirement approaches, it’s important to have a clear understanding of where your assets are held, how accessible they are, and how they will support your income needs throughout retirement.
Many people accumulate wealth across multiple account types over the course of their careers. These may include retirement plans, taxable investment accounts, cash reserves, pensions, and Social Security benefits. Each source of income can have different tax implications and withdrawal considerations, making it important to understand not only what you own but also how those assets fit together.
For many Americans, Social Security will become a meaningful component of retirement income. Understanding your projected benefit and evaluating the most advantageous filing strategy can have a lasting impact on your retirement cash flow. Likewise, if you have a pension, it is worth reviewing your payout options and survivor benefit elections well before retirement so you can make informed decisions.
3. Evaluate Your Healthcare and Medicare Strategy
Healthcare is one of the largest and most frequently underestimated retirement expenses.
If you plan to retire before age 65, developing a strategy for health insurance coverage should be a priority. Private insurance costs can vary significantly, and understanding your options ahead of time can help you avoid unexpected expenses during the transition from employment.
Once you become eligible for Medicare, the planning doesn’t stop. Medicare offers multiple coverage options, each with its own costs and benefits. Navigating those choices can feel overwhelming, particularly when considering prescription drug coverage, supplemental insurance, and long-term healthcare needs. Working with a qualified Medicare specialist can help you identify a cost-effective solution that aligns with your family’s healthcare requirements.
4. Build a Comprehensive Retirement Financial Plan
Thinking through spending, income, taxes, investments, and healthcare individually is helpful. The real value comes from bringing all of those pieces together into a coordinated retirement plan.
A comprehensive financial plan can help answer some of the most important questions retirees face. Can you afford to retire when you want to? Will your assets support your desired lifestyle for decades to come? How should you withdraw funds from different account types to manage taxes efficiently? What happens if inflation remains elevated or markets experience a prolonged downturn?
Ultimately, financial success in retirement isn’t measured by the size of an investment portfolio. It’s measured by whether your resources support the life you want to live. A well-designed retirement plan can provide confidence that your lifestyle, legacy goals, and long-term financial security remain aligned.
5. Don’t Just Retire From Something—Retire To Something
This may be the most overlooked item on any retirement checklist.
Retirement is not solely a financial event. It’s also a significant emotional and psychological transition. For decades, work often provides structure, purpose, social interaction, and a sense of identity. Stepping away from that routine can be more challenging than many people expect.
That’s why I encourage clients to spend as much time thinking about their future lifestyle as they do their finances. What will fill your days? What activities bring you energy and fulfillment? How will you stay connected to your community, family, and friends?
The clients who seem to thrive most in retirement are those who enter it with a sense of purpose. Whether that’s travel, volunteering, mentoring, learning new skills, spending time with family, or pursuing long-neglected passions, having something meaningful to retire to can make the transition far more rewarding.
Start Preparing for Retirement Before You Need To
Retirement planning is most effective when it begins well before your last day of work.
The years leading up to retirement offer an opportunity to fine-tune your spending plan, optimize income strategies, evaluate healthcare options, and ensure your financial resources align with your goals.
Most importantly, they provide time to think intentionally about what you want this next chapter to look like.
Our purpose is to help financially prepare you to meet your goals so you can focus on what matters most: living your best life.
Frequently Asked Questions
What should I do five years before retirement?
Five years before retirement is an ideal time to evaluate your retirement savings, estimate future expenses, review investment allocations, create a retirement income strategy, and begin planning for healthcare and Medicare costs.
What is the most important part of retirement planning?
While saving is critical, understanding your expected spending needs is often the most important factor. A retirement spending plan provides the foundation for determining whether your savings and income sources can support your lifestyle.
How much money do I need to retire?
The amount needed for retirement depends on your desired lifestyle, expected expenses, income sources, longevity, and healthcare costs. A personalized financial plan can help determine an appropriate target based on your goals.
When should I start planning for Social Security?
Ideally, you should evaluate your Social Security strategy several years before retirement. Filing age can significantly affect lifetime benefits, especially for married couples.
What healthcare costs should I plan for in retirement?
Retirees should plan for health insurance premiums, Medicare costs, prescription medications, out-of-pocket medical expenses, dental care, vision care, and potential long-term care needs.
Should I pay off debt before retirement?
In many cases, reducing or eliminating high-interest debt before retirement can improve financial flexibility and reduce stress. However, the best approach depends on your overall financial situation and retirement goals.
How do I know if I’m ready to retire?
Retirement readiness involves both financial and personal factors. A comprehensive retirement plan can help determine whether your income and assets are sufficient, while thoughtful lifestyle planning can help ensure you’re emotionally prepared for the transition.
Disclaimers
This article was originally written in May 2023 and most recently revised for accuracy as of June 2026. Past performance is not indicative of future results, and there is a risk of loss of all or part of your investment. The opinions and analyses expressed in this newsletter are based on Curi Capital, LLC’s (“Curi Capital”) research and professional experience are expressed as of the date of our mailing of this newsletter. Certain information expressed represents an assessment at a specific point in time and is not intended to be a forecast or guarantee of future results, nor is it intended to speak to any future time periods. Curi makes no warranty or representation, express or implied, nor does Curi accept any liability, with respect to the information and data set forth herein, and Curi specifically disclaims any duty to update any of the information and data contained in this newsletter. The information and data in this newsletter does not constitute legal, tax, accounting, investment or other professional advice. Returns are presented net of fees. An investment cannot be made directly in an index. The index data assumes reinvestment of all income and does not bear fees, taxes, or transaction costs. The investment strategy and types of securities held by the comparison index may be substantially different from the investment strategy and types of securities held by your account.
The content contained herein was generated by Curi Capital with the assistance of an AI-based system to augment the effort.
Certified Financial Planner Board of Standards, Inc. owns the certification marks CFP®, CERTIFIED FINANCIAL PLANNER™ and federally registered CFP (with flame design) in the U.S., which it awards to individuals who successfully complete CFP Board’s initial and ongoing certification requirements.
