2027 Retirement Readiness Check: 6 Things to Discuss with Your Financial Professional Annually

Helen, a 59-year-old hospital administrator, was not behind on saving. She had a 401(k), a modest brokerage account, and a general sense that things were fine. She sat down with her calendar in early December and realized she had done this exact thing every year for the past decade: made a mental note to “look at retirement stuff” before the holidays hit, then let the note quietly expire by January.

What she had never done was sit down with a financial professional and walk through her full retirement picture as one connected plan, rather than a handful of accounts she checked separately and rarely together.

Helen’s habit is common, and the end of the year is a useful time to change it. Statements arrive, deadlines cluster, and the new year provides a natural reason to review the bigger picture. Rather than deciding on your own what, if anything, should change, consider using an annual conversation with your Investment Counselor to ask a simpler question: Does my retirement plan still reflect my goals, timeline, needs, and circumstances? The following six areas can help guide that conversation each year.

1. Retirement Savings Progress

One annual discussion point is whether your current progress in savings is keeping up with the retirement goals you have set.

Surveys have shown that retirement confidence has shifted recently. The 2026 Retirement Confidence Survey from EBRI and Greenwald Research found that worker confidence in having enough money for a comfortable retirement fell to 61%, down from 67% the year before. Retiree confidence also declined, from 78% to 73%.

Reviewing with Your Investment Counselor

It is worth checking where you actually stand rather than relying on a general expectation or feeling. A conversation with your Investment Counselor may help between your current savings trajectory and what your specific retirement goals could likely require.

2. Portfolio Allocation and Risk

A portfolio established five or ten years ago may no longer reflect your current risk tolerance or time horizon, particularly if your life circumstances or financial goals have changed.

Reviewing with Your Investment Counselor

This can be worth discussing directly with your Investment Counselor. Has your comfort with risk changed? Has your retirement timeline changed? Does your current allocation still reflect the objectives you originally established? An annual review can also help you see whether changes in market values have altered your portfolio’s balance over time.

This conversation works best when it starts with your own circumstances rather than a questionnaire completed years ago. How would you feel if the market declined significantly? Has the expected date of when you need retirement income changed? Have your family responsibilities or financial priorities shifted? Sharing these answers with your financial professional can help make the annual review more relevant to your current situation.

3. Retirement Income Needs

Another important annual consideration is how well your expected retirement income compares with the lifestyle and expenses you anticipate.

Savings totals only tell part of the story. The more useful question heading into a new year is what income your retirement accounts, Social Security, and any pension will actually need to produce, and whether that combination realistically covers your expected expenses.

Reviewing with Your Investment Counselor

Reviewing with a financial professional can help you look at income needs as part of a greater strategy, rather than one account balance at a time. This conversation can factor in when you plan to retire, how your expenses may shift once you do, and how long that income realistically needs to last.

4. Year-End Tax and RMD Considerations

Tax-related deadlines and distribution rules can change with age and circumstances, so it’s important to revisit them each year.

Generally, 73 is the age that IRS requires you to take required minimum distributions (RMDs) from your retirement accounts. If you are required to take an RMD, the IRS deadline is December 31 for most account holders (with a one-time exception allowing a first RMD to be delayed until April 1 of the following year).

Missing an RMD deadline carries a penalty of 25% of the amount not withdrawn, which makes this one of the more consequential year-end items to confirm rather than assume is handled.

Reviewing with Your Investment Counselor

Anyone turning 73 in 2026 may also discuss with their Investment Counselor whether taking their first RMD this year or delaying it makes more sense for their specific tax situation, since delaying can mean two taxable distributions landing in the same year.

5. Social Security and Medicare Planning

As retirement approaches, Social Security and Medicare decisions become increasingly important subjects for an annual planning conversation.

In 2026, retirees received a 2.8% cost-of-living adjustment (COLA). For 2027, the Social Security Administration announced that the COLA will be 3.6%. Since this adjustment responds to inflationary trends year-to-year, it isn’t something you can count on as a set amount when planning for retirement.

Instead, it may help to focus on what you can control, such as your claiming strategy. Claiming before full retirement age permanently reduces the benefit, while delaying increases it. Medicare decisions deserve equal attention, particularly for anyone whose income might cross an income-related premium threshold, since a large withdrawal or a Roth conversion can affect Medicare costs two years later.

Reviewing with Your Investment Counselor

Evaluating Social Security and Medicare with your Investment Counselor can help determine how much additional income may be needed to bridge to your retirement goals.

6. Beneficiary and Estate Plan Reviews

Beneficiary information and estate-planning documents should also be revisited periodically, especially after major life events.

Beneficiary designations on retirement accounts and life insurance operate outside of a will, which means an outdated form can override even a carefully written estate plan. A year-end review is a natural time to confirm that beneficiaries on every retirement account and life insurance policy, and any accompanying estate planning documents, still reflect your current wishes, particularly after a marriage, divorce, birth, or death in the family.

It is also worth confirming that every account lists a contingent beneficiary, not just a primary one, since accounts without one can end up moving through probate rather than passing directly to the people you intended.

Reviewing with Your Investment Counselor

Your Investment Counselor can be a helpful resource as you think through how your investment accounts fit into your broader estate plan and your goals for passing assets on to the people and causes that matter to you.

Why This Works Best as One Conversation

Most people do not experience these six areas as six separate issues. Savings, risk tolerance, income needs, taxes, Social Security and Medicare, and beneficiary decisions are all parts of the same retirement picture. That is one reason an annual conversation with an Investment Counselor can be valuable: it creates a regular opportunity to review the connections among them rather than looking at each item in isolation.

You do not need to arrive at that meeting knowing which questions matter most or what actions, if any, may be appropriate. The purpose of the conversation is to review what has changed, identify areas that deserve attention, and make sure your Investment Counselor understands the full context of your retirement goals. The six considerations provide a practical framework for that discussion.

“The biggest value I provide isn’t in any single one of these six areas, it’s in looking at all of them together as one connected picture,” says David Neuwirth, Senior Vice President, Investments at David Lerner Associates.

“Savings, risk tolerance, income needs, taxes, Social Security, and your beneficiaries all affect each other. A client may come in worried about one thing, and we may end up finding something completely unrelated that needs more attention, like a beneficiary form nobody has looked at in 15 years. That only happens because we’re looking at the whole picture, not just the question they walked in with.”

That human relationship matters. Online tools and account statements can provide useful information, but they do not replace a conversation about how your finances connect with your goals, family circumstances, retirement timeline, and concerns. A regular annual review gives you and your Investment Counselor an opportunity to revisit those factors together and identify questions that may otherwise be overlooked.

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Material contained in this article is provided for information purposes only. It is not intended to be used in connection with the evaluation of any investments offered by David Lerner Associates, Inc. This material does not constitute an offer or recommendation to buy or sell securities and should not be considered in connection with the purchase or sale of securities. These materials are provided for general information and educational purposes, based on publicly available information from sources believed to be reliable. We cannot assure the accuracy or completeness of these materials. The information in these materials may change at any time and without notice. The subject of this article is fictitious and created for illustrative purposes only. It is based on events of a similar nature and should not be interpreted as a direct depiction of any specific individual, organization, or incident. Any resemblance to actual persons, living or deceased, or actual events is purely coincidental. David Lerner Associates does not provide tax or legal advice.