Many are familiar with medical age milestones. For example, mammogram at age 40, and colonoscopy starting at age 45. Similar to these medical milestones, you will want to be aware of key financial ages, especially as you plan for retirement. 

From our experience turning 50, 55, 59½, 65 and 73 are important milestone ages for many investors and savers. We've compiled a list of key financial variables to consider at each age.

Catch-Up Contributions

Starting the year you turn 50; you can make catch-up contributions to several different retirement plans. Contributions can be made anytime throughout the year, as long as you turn 50 by year-end.

Taking advantage of catch-up contributions is a great way to set aside additional dollars for retirement (both pre-and post-tax) and may also help individuals who potentially didn’t save early enough in their careers.

The catch-up contribution amounts shown below are all associated with the 2026 tax year. Furthermore, if you are married, these limits also apply to your spouse.

IRAs and Roth IRAs

The annual contribution limit between these two accounts (aggregated) is increasing to $7,500 per individual. For those over age 50, an additional $1,100 catch-up contribution is allowed, bringing the maximum to $8,600.

401k, 403b & 457b Plans

The annual contribution limit is increasing to $24,500. For those over age 50, an additional $8,000 catch-up contribution is allowed. If you are between the ages of 60-63 in 2026, you are likely eligible to make a catch-up contribution of $11,250 (instead of $8,00).

Special catch-up rules may apply to 401k plan participants aged 60-63, as well as certain 403b plan contributors who have 15 or more years of service and government employees during the final three years before retirement (generally defined as age 65).

Simple IRAs

For participants in these small employer retirement plans, the annual contribution limit is currently $17,000. For those over age 50, an additional $4,000 catch-up contribution is allowed.

Similar to 401ks, 403bs and 457b plans, Simple IRAs also offer special catch-up rules to individuals aged 60-63 in 2026.

Health Savings Accounts

If you are covered by a high deductible health insurance plan and would like to make pre-tax contributions into a Health Savings Account (HSA), the contribution limits have increased in 2026. The new contribution limits are $4,400 (Individual) and $8,750 (Family). If you are at least 55 years old, you also have the ability to make catch-up contributions to your HSA.

In the calendar year 2026, the annual catch-up contribution is $1,000. If you and your spouse each have a Health Savings Account, you may both be eligible to make this catch-up contribution, essentially doubling present and future tax benefits.

The Health Savings Account is a great savings mechanism since it offers what we refer to as “Triple Tax-Free Benefits," which can consist of the following:

Pre-Tax Contributions

Your contributions to an HSA are made on a pre-tax basis. That means you avoid paying ordinary income tax on whatever amount you contribute to the HSA during the applicable tax year.

Tax-Free Growth

You can invest the balance in your HSA, much like you would with your 401k, IRA, Roth IRA, and taxable accounts. The benefit of investing money in your HSA is that the growth is tax-free. Considering the projected future costs associated with health care, this is a great way to build your portfolio to cover medical expenses during your retirement years.

Tax-Free Withdrawals

As long as your distributions are used for qualified medical expenses, they can come out of your HSA on a tax-free basis—both now and in the future.

Exceptions to Early Withdrawal Penalties

As a general rule, distributions from a retirement plan before the age of 59½ are subject to ordinary income tax and a 10% early withdrawal penalty.

Now that you are 55 years old, you may be able to avoid the early withdrawal penalty on distributions from specific retirement plans. However, before initiating a withdrawal, we highly recommend you connect with your Financial Advisor and Tax Professional to ensure that the distribution qualifies for an exception.

Some of the more common early withdrawal exceptions include:

401k/403b Plan (Age 55 and Separation from Service)

The keyword here is “AND.” To be eligible for this unique exception, you must separate from service (i.e., retire, quit, termination, layoff) after age 55. Assuming separation from service happens after age 55 (and before age 59½), you may find that you are eligible to take penalty-free withdrawals from your former workplace retirement plan. The distributions would still be subject to ordinary income tax, however. Another key variable in this situation is that the assets need to be retained inside your former workplace retirement plan (i.e., they cannot be rolled over to an IRA).

72(t) IRA Distributions

If you aren’t yet age 59½, but you have already rolled your workplace retirement plan into an Individual Retirement Account (IRA), you may still be eligible to avoid the 10% early withdrawal penalty. One way to avoid the fee can be by setting up a 72(t) IRA. This strategy allows IRA holders to access funds in their account without incurring the 10% early withdrawal penalty, assuming the following conditions are met:

• Substantially Equal Periodic Payments – as long as distributions are set up as part of a series of substantially equal periodic payments, which need to last until age 59½ or 5-years (whichever is longer), you may be able to avoid the 10% early withdrawal penalty.
• Any changes in the substantially equal periodic payments that are made within 5-years of the date of the first payment (or age 59½ if longer than 5-years) will negate the benefit of avoiding the 10% early withdrawal penalty.

Workplace Retirement Plan Rollovers (In-Service)

Once you reach age 55 (while still actively employed), your employer-sponsored retirement plan may give you the option of doing an in-service rollover of your workplace retirement plan into a separately managed IRA. If you prefer the customization, consolidation, and professional advice available through your Investment Advisory Firm, this may be a consideration.

Turning age 59½ is an important milestone for many as it is the magic age associated with accessing funds in your retirement plan without being subject to the 10% early withdrawal penalty. However, there are some instances where investors still need to pay attention to applicable rules and regulations to make sure Uncle Sam doesn’t show up with a surprise tax bill!

Retirement Plan distrubutions

You’ve spent the better part of your career setting aside money into pre-and post-tax investment accounts to help fund your various retirement goals. Now that you’ve turned 59½ years old, you’ll need to determine the most tax-efficient way of tapping into your investment portfolio to reduce the impact of taxes and, more importantly, penalties!

The following accounts are common amongst retirement investors, but some of these carry a few distinct rules associated with taking penalty-free distributions:

401k, 403b and 457b plans

Generally speaking, once you turn 59½ years old, you are eligible to take penalty-free distributions from these employer-sponsored retirement plans.

Workplace Retirement Plan Rollovers (In-Service)

Once you reach age 59½ (while still actively employed), your employer-sponsored retirement plan may give you the option of doing an in-service rollover of your workplace retirement plan into a separately managed IRA. If you prefer the customization, consolidation, and professional advice available through your Investment Advisory Firm, this may be a consideration.

IRAs

Generally speaking, once you turn 59½ years old, you are eligible to take penalty-free distributions from your IRA. If your IRA consists of 100% pre-tax money, you can expect 100% of your distributions to be as fully taxable as ordinary income. However, to the extent you’ve made nondeductible contributions into your IRA, you should be able to refer to IRS Form 8606, which indicates your aggregate basis within IRAs. In this instance, distributions will be pro-rated between the taxable and tax-free (return of basis) portions during your retirement years.

Roth IRAs

You can always take out whatever you’ve contributed to a Roth IRA
(both tax and penalty-free), regardless of your age. With that said, if you’ve done a good job of saving for retirement, hopefully, you’ve retained the assets inside your Roth IRA so they’ve enjoyed the benefits of compound growth over several decades.

At retirement, you may now find yourself in the position of wanting to tap into your Roth IRA to cover ongoing expenses. Before doing this, take into account the two major components of proper Roth IRA distribution planning (to tap into the growth component tax and penalty-free):

1. The Roth IRA must have been established for at least 5-years AND…

2. The Roth IRA owner must be age 59½.

As long as these two critical components have been met, tax and penalty-free distributions (including those tied to the growth portion of the Roth IRA) can be taken.

Health Savings Accounts

Unfortunately, age 59½ has no bearing on distributions from an HSA. Instead, tax-free distributions can be taken anytime during the account owner’s lifetime, as long as the funds are used to pay for qualified medical expenses. If distributions are taken for non-qualified expenses, they are subject to ordinary income tax and a 10% penalty. One important exception to the 10% penalty, would be distributions that are taken post-age 65 for non-qualified expenses. In these instances, ordinary income tax is due, but there is no 10% early withdrawal penalty, essentially making the distribution equivalent to that of a 401k, 403b or 457b plan withdrawal.

Social security: choices begin

While you can claim Social Security retirement benefits as early as age 62, claiming early results in permanently reduced monthly benefits. The decision about when to claim should take into account your health, other retirement assets, marital status, and long-term income needs. For many households, taking time to evaluate these trade-offs may be one of the most important retirement planning decisions they make.

Turning age 65 is an important milestone as you are likely now eligible for Medicare and are eligible to take HSA distributions penalty-free. 

Medicare

Enrollment into Medicare is done through the Social Security Administration, and you should begin this process roughly three months prior to turning age 65.

Medicare Part B and D carry a monthly premium that is based on your MAGI (Modified Adjusted Gross Income).  Medicare Supplemental Plans help fill the holes associated with needs not typically covered by Medicare and also require a separate monthly premium.

If you fail to sign up for Medicare in the appropriate timeframe, you may become subject to a late-enrollment penalty. This penalty can be as high as 10% for each year you could have signed up for Part B, but didn’t.  Similar penalties are in place for those who don’t sign up for Part D within the appropriate timeframes.

If you are 65 years old, still working, and your employer has 20 or more employees, your company would remain your primary insurer, and you can delay enrolling in Part B without worrying about a late enrollment penalty. If your company has fewer than 20 employees, however, Medicare is considered your primary insurer, and you will want to be sure to sign up as soon as possible in order to avoid penalties.

HSA Distributions

Once you turn 65 years old, you are eligible to take money out of your HSA without fear of penalty–regardless of why the distribution is being taken. You will still be subject to ordinary income tax on the distribution. Another way of thinking about the age 65 rule is that the HSA can effectively act as a “bonus 401k plan.”

Suppose you take a distribution from your Health Savings Account before age 65 for a non-covered medical expense. In that case, the distribution will be subject to ordinary income tax and a 10% early withdrawal penalty. Again, this is why it’s very important to keep all of your medical receipts over multiple years so you can justify the distribution as being qualified.

Social Security: latest age to claim

If you've delayed claiming Social Security retirement benefits, age 70 is generally the latest age to begin. Delayed retirement credits stop accumulating after age 70, so waiting longer typically doesn't increase your monthly benefit.

Qualified Charitable DISTRIBUTIONS

Individuals age 70½ and older may be eligible to make qualified charitable distributions directly from an IRA to a qualified charity. QCDs can satisfy charitable goals while potentially reducing taxable income.

Required Minimum Distributions (RMDs)

The age at which individuals need to begin taking Required Minimum Distributions (RMDs) from their retirement plans is now 73. This change became effective with the passage of the SECURE 2.0 Act (passed by Congress in late-2022), which expands upon the original SECURE Act that was passed at the end of 2019.

The technical guideline is that an individual must take his or her first RMD by April 1st, following the year he/she turns 73. If the individual elects to defer the first RMD until April 1st of the following year, that individual must also take his/her second year RMD before the following year-end. This essentially means taking two RMDs in the same calendar year, which may not be wise from a tax planning standpoint.

Additional legislation included in the SECURE 2.0 Act is that the RMD age will be pushed out to age 75 starting in the year 2033.

The table below outlines the phased-in SECURE 2.0 Act RMD changes:

For those who are not yet subject to RMDs, but are over age 70½, you still have the ability to make Qualified Charitable Distributions (QCDs) from your IRA to charity. This can be an excellent way to accomplish your charitable and philanthropic goals since the amount donated out of your IRA is excluded from your taxable income.

Estate planning review

Your estate plan should evolve as your life changes. Reviewing your documents periodically can help ensure your wishes are clear, the people you've chosen for important roles are still appropriate, and your plan reflects current family dynamics and financial circumstances.

Some financial milestones arrive on schedule. Turning 50, becoming eligible for Medicare, or beginning Required Minimum Distributions are all examples of age-based planning opportunities. But many important financial decisions are tied to life events rather than birthdays. Getting married, changing jobs, welcoming a child, caring for aging parents, or navigating the loss of a loved one can bring new questions and responsibilities. These transitions often happen quickly, leaving little time to consider the financial implications. While every situation is unique, taking time to revisit your financial plan during these moments can help you identify opportunities, avoid unintended consequences, and make decisions that align with your goals and values.

Below are several life milestones that may warrant a conversation with your financial advisor.

Marriage

Combining your lives often means combining financial priorities as well. This may be a good time to review beneficiary designations, update insurance coverage, discuss spending and saving goals, and revisit your estate planning documents.

Divorce

A divorce can affect everything from cash flow and taxes to retirement savings and estate plans. Reviewing your financial picture during this transition can help ensure important details aren't overlooked.

Welcoming a Child or Grandchild

Whether you're becoming a parent or grandparent, this milestone often brings new planning considerations. You may want to review insurance needs, update estate documents, revisit your savings goals, or explore education funding strategies.

Changing Jobs or Careers

A new opportunity can also bring new decisions. Consider reviewing workplace benefits, retirement plan options, stock compensation, and how the change may affect your overall financial plan.

Moving to a New State

Relocating can be exciting, but it may also bring financial considerations that aren't immediately obvious. A move could affect your state income taxes, estate planning documents, insurance coverage, healthcare providers, and retirement cash flow strategies.

Caring for Aging Parents

Supporting a parent often involves balancing emotional and financial considerations. Conversations around healthcare, long-term care planning, powers of attorney, and family responsibilities may become increasingly important.

Receiving an Inheritance

An inheritance can create opportunities, but it may also come with complex decisions. Understanding tax implications, beneficiary rules, and how these assets fit into your long-term goals can help you move forward thoughtfully.

Selling a Business

For business owners, a sale may represent both a significant financial event and a major life transition. Planning ahead can help address tax considerations, retirement income strategies, and what's next after the transaction.

Loss of a Spouse or Partner

The loss of a loved one often requires navigating important financial decisions while grieving. Reviewing cash flow needs, beneficiary updates, Social Security considerations, and estate settlement responsibilities can provide clarity during a difficult time.

Retirement

Retirement isn't simply the end of a career. It's the beginning of a new chapter. This transition may involve decisions around income planning, Social Security, healthcare, taxes, and how you envision spending your time in the years ahead.