For many people, retirement is the reward for decades of hard work. Yet while most of us spend years saving for retirement, far fewer spend time planning for what retirement will actually look like. Retirement isn’t just about reaching a certain number in your investment account. It’s about creating a thoughtful plan that provides confidence, flexibility, and peace of mind.
Whether retirement is five years away or just around the corner, now is the perfect time to review your financial plan. Use this checklist to help ensure you’re prepared for one of life’s biggest transitions.
Define What Retirement Looks Like
Before discussing investments or income, take a step back and ask yourself:
- When would you like to retire?
- Will you work part-time or fully retire?
- Where do you want to live?
- How do you plan to spend your time?
- Will you travel frequently?
- Do you plan to help children or grandchildren financially?
- What are your biggest goals for retirement?
Your financial plan should support the life you want, not the other way around.
Understand Your Retirement Income
One of the most common questions we hear is: “How will I replace my paycheck?”
Your retirement income may come from several sources, including:
- Social Security
- Retirement accounts (401(k)s, IRAs, Roth IRAs)
- Pension benefits
- Taxable investment accounts
- Rental income
- Part-time employment
- Required Minimum Distributions (RMDs)
A thoughtful withdrawal strategy can help your savings last longer while reducing unnecessary taxes.
Create a Retirement Spending Plan
Many expenses change in retirement.
Some costs naturally decrease:
- Commuting
- Payroll taxes
- Retirement plan contributions
- Work-related expenses
Others often increase:
- Healthcare
- Travel and hobbies
- Home maintenance
- Supporting family members
- Long-term care needs
One of the biggest mistakes retirees can make is assuming their expenses will remain flat throughout retirement. Inflation continues to increase the cost of everyday living, making it important to plan for a retirement income that can grow over time. A realistic spending plan helps ensure your lifestyle remains sustainable not just during the early years of retirement, but throughout your lifetime.
Develop a Tax Strategy
Taxes don’t disappear when you retire. In fact, retirement often presents unique tax planning opportunities.
Questions worth considering include:
- Should you complete a Roth conversion before Required Minimum Distributions begin?
- Which accounts should you withdraw from first?
- How will Social Security affect your tax picture?
- Could Qualified Charitable Distributions (QCDs) reduce taxable income?
- Are there opportunities to recognize income during lower tax years?
Proactive tax planning can potentially save thousands of dollars over the course of retirement.
Have a Social Security Strategy
Claiming Social Security is one of the most important retirement decisions you’ll make.
The right claiming strategy depends on factors such as:
- Your health
- Family longevity
- Marital status
- Other retirement income
- Tax implications
There is no universal “best age” to claim benefits. The right answer depends on your unique circumstances and your overall retirement plan. As financial advisors, we regularly help clients evaluate different claiming scenarios so they can make an informed decision based on their individual goals.
Prepare for Healthcare Costs
It’s no surprise that healthcare is one of the largest expenses retirees face.
Be sure to understand:
- Medicare enrollment deadlines
- Medicare Parts A, B, C, and D
- Supplemental insurance options
- Prescription drug coverage
- Out-of-pocket healthcare costs
Planning ahead can help you avoid costly enrollment penalties and unexpected expenses. Be sure to check out the Bloom Advisor’s Medicare checklist for a helpful guide.
Plan for Long-Term Care
Many retirees will need some form of long-term care during their lifetime, whether it’s assistance at home, an assisted living community, or skilled nursing care. While no one can predict what the future holds, planning ahead can help preserve your financial independence and reduce the burden on your loved ones.
Topics to discuss include:
- How care might be funded
- Long-term care insurance or other funding strategies
- Family caregiving expectations
- Protecting assets
- Estate planning considerations
Having these conversations before they’re needed is one of the greatest gifts you can give your family. A proactive plan provides more choices, greater flexibility, and peace of mind.
Review Your Investment Strategy
As retirement approaches, your investment strategy should evolve alongside your goals.
Ask yourself:
- Is your portfolio appropriately diversified?
- Are you taking more risk than necessary?
- Do you have enough liquidity for short-term spending needs?
- Is your investment allocation aligned with your retirement income plan?
Successful investing in retirement isn’t about chasing the highest return, it’s about creating a portfolio that supports your long-term goals through changing market conditions.
Review Your Estate Plan
Every retirement plan should include an estate plan and it’s important to review these documents regularly:
- Will
- Revocable Living Trust (if appropriate)
- Durable Financial Power of Attorney
- Patient Advocate Designation / Medical Power of Attorney
- HIPAA Authorization
- Beneficiary Designations
Life events such as marriages, divorces, births, deaths, or significant financial changes often make it necessary to update your estate plan. To learn more, visit our website for estate planning resources and educational tools.
Organize Your Financial Life
One of the greatest gifts you can leave your family is organization. Maintain an updated record of:
- Investment accounts
- Bank accounts
- Insurance policies
- Estate planning documents
- Tax returns
- Online account information
- Professional contacts
At Bloom Advisors, we’ve seen firsthand how organization can reduce stress and almost certainly save you and your loved ones time and money. To get started, download our Document Locator tool, a simple but invaluable tool designed to organize your important financial, legal, and personal information in one convenient place.
Meet With Your Financial Advisor Regularly
Retirement planning isn’t a one-time event. Tax laws change, markets fluctuate, families grows and priorities evolve. Regular reviews allow your financial plan to adapt as your life changes and help you stay on track toward your long-term goals.
Retirement Is About More Than Money
A successful retirement isn’t measured solely by the size of your portfolio. It’s measured by the confidence that comes from knowing your finances support the life you want to live.
At Bloom Advisors, we believe financial planning is about so much more than investments. It’s about helping individuals and families make informed decisions through every stage of life, from preparing for retirement to navigating the years that follow. To learn more about some of the many ways we support our clients, view our 26 Ways We Add Value document.
If retirement is on the horizon, now is an excellent time to review your plan. A thoughtful conversation today can help you approach tomorrow with greater clarity and confidence.
Have questions about your retirement plan? We’d be happy to help you evaluate where you stand and identify opportunities to strengthen your plan for the years ahead.

