As fee-only financial planners in Cary, NC & Chattanooga, TN we work with individuals and couples preparing to retire in the next 5–10 years. This article is meant to address and help you think through common questions like:
When can I retire?
Do I have enough money to retire?
When should I take Social Security?
How do I turn my savings into income in retirement?
How should I plan for healthcare related costs in retirement?
While every retirement plan is unique, there are several core areas everyone should evaluate before they step away from work.
Here are five essential things to consider before retirement:
1. Define Your Retirement Goals & Lifestyle
You need to plan out your goals in retirement
How much can you spend every month in retirement?
What do you want your vacation or home improvement budget to be?
What are you going to fill your free time with? Family, hobbies, new ventures?
2. Retirement Income Planning
You do not have a steady job income anymore - so what are you going to live on?
When is the best time to take Social Security? - This is a massive decision and needs to be taken with immense care
What investment account should you pull money out from first in retirement? Taxable Accounts? IRA Accounts?
What are the tax impact from withdrawing from different types of accounts?
How will distributions from your investment accounts affect Social Security and Medicare benefits & taxation?
3. Are Your Investments Aligned with Retirement Risk?
Concentration Risk: Almost 40% of the S&P 500 is in 10 stocks. The majority of these stocks represent the technology sector as well. This type of concentration exposure is a massive risk to your retirement plan.
Asset Location: What type of investments are in each of your investment accounts? They should not all be invested the same – based on your retirement income needs and age – your IRA, Roth IRA, and Taxable Brokerage Accounts should take tax considerations in their objectives.
What should my Asset Allocation be in Retirement? What percentage of your funds are in stocks? What about bonds? What is your withdrawal strategy when the market sees a downturn, and you need to take money from your portfolio?
4. Healthcare & Medicare Planning
Health Insurance: Will you need health insurance between your retirement age and Medicare (Age 65)?
Medicare Costs & Income-Related Monthly Adjustment Amount (IRMAA) Surcharges: How does your retirement income impact your Medicare premiums? Are you required to pay an IRMAA surcharge based on your income level? If so – what are strategies you can implement to avoid higher premiums and surcharges?
Long-Term Care strategies: Do you have long-term care insurance? If not, are you aware of the cost of long-term care?
5. Have You Reviewed Your Estate & Legacy Plan?
Wills & Trusts: Do you have a clear Will and Trust outlined to dictate where your assets are going?
Probate: Do you have assets that will go through probate? Probate can be costly (2%-5% of your estate). Probate can also take upwards of a year to get your assets distributed.
Healthcare Directives: Do you have your health care directives drafted and filed?
Beneficiary Designations: Have you checked your beneficiary designations on your investment accounts and insurance policies? The number of times we see incorrect beneficiary designations or ex-spouses on beneficiary designations are staggering.
Charitable Gifting Strategies: How can you give to the causes you care about while also lowering your tax liability? How can you lower your Required Minimum Distributions (RMDs) by using Qualified Charitable Distributions (QCDs)? Should you open a Donor Advised Fund?
Final Thoughts: "Can I Retire Today?"
Answering the question, “Can I retire today?” is never simple. As we have discussed, there are many moving parts — income planning, investments, taxes, healthcare, estate planning, and more. That is why it is essential to have a fee-only financial advisor in your corner to help you navigate each of these critical decisions with confidence and transparency.
Retirement is not a one-time event — it is an ongoing process. It is not just about deciding when to stop working; it is about staying engaged with your financial plan as life evolves. Your goals, risk tolerance, and tax situation can change year to year, and your retirement plan should adapt right alongside them.
At our firm, we meet with clients throughout the year to review their retirement strategy, identify opportunities, and make sure they remain on track to reach their goals. That consistent guidance helps turn uncertainty into clarity — and keeps your retirement plan working for you, not against you.
Choosing to retire is one of the most important decisions someone can make in their lifetime. Read this article to learn about all the things you should consider prior to making this life-changing decision.
Are you a tech employee with an equity compensation plan? If you want to learn more details about RSUs, ISOs, NSOs, & ESPPs, take a look at this article.
