Do You Have Enough ‘Retirement Empathy’?

Encouraging clients to discuss their post-retirement fears can deepen your relationship and motivate them to take action.

By Dave Buck
Dave Buck
Dave Buck

Benjamin started out our conversation with, “I am going to retire in 2024.”

“Congratulations!” I enthusiastically stated.

Then just silence, no response.

Sensing there was more to that statement I asked, “When you say, ‘I am going to retire in 2024’, what’s the first emotion that comes to your mind?”

In almost a whisper, seemingly so no one else could hear (even though it was just the two of us), he responded, “I’m actually a little scared.”

Benjamin has held multiple leadership roles in multibillion dollar companies with many direct reports. Ask him about his work and with a noted air of authority he’ll confidently walk you through the details of his profession and his contributions. There’s no egotism, just a certainty about his abilities and satisfaction he gets from the job he does and the people he impacts.

As he inches closer to 70, Benjamin feels it is time to step away from corporate life. He’s financially ready (been that way for a while) but is struggling emotionally to stand aside and live a post-career life.

As financial professionals, you probably have a fair share of Benjamins as clients. In many cases, the “Benjamin types” have more than enough to maintain an excellent lifestyle with negligible financial risk. You may have even tested their attitude with a good-natured question like, “Come on, when are you going to retire already?” However, what your clients might be seeking is not humor or playfulness:  They could be searching for some retirement empathy.

The new year will bring new declarations of retirement. While there are a lot of factors around the decision, many business professionals wait until they receive their annual bonus to retire, which typically occurs in March. Therefore, the first part of the year can be a moment of retirement truth for many. While there will certainly be a fair share of celebratory assertiveness, know that behind the smiles of many will be misgiving, hesitation, and nervousness.

Additional Reading: Togetherness Doesn’t Have to Tear Retired Couples Apart

Therefore, when the client retirement announcement comes, before you dive into the financial metrics and details, invest in a little emotional understanding. It does not require a degree in phycology or special certifications. Practicing the concept of retirement empathy can be targeted and concentrated.

Employ Active Listening

Benjamin knows what I do for a living. That’s why he was talking to me. Nonetheless, he still hesitated to tell me his state of mind. Many declared retirees are wary to share their true feelings because retirement is seen by society as something to be attained and celebrated. They do not want to be perceived as smug, ungrateful, and even whiny.

A way of leading into the conversation  could be, “I am so happy to hear about your decision to retire. While I am ready to start to walk you through the financial process, tell me how you are feeling about your decision?” When listening, ask clarifying questions. Show them that you appreciate any conflicting emotions and that their feelings are normal.

Don’t Minimize

While on the surface client emotions might seem superficial and shallow, don’t minimize their feelings.  Acknowledge their anxieties and worries. Phrases like “That’s understandable” or “I’m not surprised you’re feeling that way” go a long way in building trust and rapport.

Even with me, Benjamin at first was guarded in what he shared. He’s used to being the leader, the one people came to for direction and advice. Naturally and comfortably sharing personal feelings will be difficult for many people (particularly when working with couples).

Normalize Their Life

Benjamin is going to go from a 50-hour-a-week job with regular business travel, to having 30% more free time in his life (50 hours divided by 168 hours). That is not normal for him. However, that is going to be his new normal.

Take the opportunity to talk with your clients who are in retirement now, and who do it well. Find out how they made the adjustment. See if you can create a list of “retirement mentors” who are willing to talk to your soon-to-be retirees about what makes post-career life satisfying and normal.

Highlight Values

Retirement planning isn’t just about financial projections; it’s about aligning finances with their desired lifestyle and purpose. Assist in unpacking what is important to them and what brings value into their lives, outside of their career.

Benjamin is starting his journey to envision his ideal retirement. He has so many strengths used in the corporate world that can be tailored to fit into his upcoming retirement life. Vaues do not need to change because a career is no longer there.

Emphasize Partnership

This is a wonderful opportunity for you, as the financial advisor, to be seen as the partner and not just the provider. Offer them not just financial advice but also emotional support and guidance. If you do not feel comfortable in that area, then work to partner and network with professionals who specialize in non-financial retirement planning.

The Empathy Reward

The more time you invest in understanding the post-career emotional concerns of your clients, the deeper you enhance the working relationship. You’ll be in a better position to provide them with tangible financial outcomes. While you are not a therapist, you can be a solid source to reduce anxiety. In a highly competitive financial services industry, genuine compassion followed by responsiveness can reward you with greater client satisfaction and growth.

I am really looking forward to seeing the lifestyle strategy Benjamin creates. He’s still uneasy about the next steps. However, just being able to articulate to someone else that he was a little scared about retirement made him feel better. Benjamin saw there was an empathetic person appreciating his hesitancy, opening him up to begin to take action. You can be that understanding somebody.

David Buck is the author of the book “The Time-Optimized Life, owner of Kairos Management Solutions, LLC, and founder of the Infinity Lifestyle Design program. As a certified professional retirement coach (CPRC), David works with financial services providers helping their clients create a post-career lifestyle strategy. To learn more, contact him at or visit Infinity Lifestyle Design.


Latest news

More Retirees are ‘Unretiring,’ Survey Reveals

Advisors say near-retirees and retirees are much less prepared for retirement than they think they are, according to Allspring.

Advisors Dabbling in DC Market Seek Greater Support: Cerulli

Providing them with tools, education and guidance would help them grow their retirement-plan businesses, says Cerulli Associates.

Executives Traveling on Corporate Jets Face IRS Scrutiny

Do you have executive clients who might be using a corporate jet for personal use? Tell them the IRS has announced a crackdown.

U.S. Solo Renters Age 50+ Way Up

The number living alone rose by more than half a million, but there’s been a growing trend of older people living with roommates.

SEC Settles Charges Against Former Advisor

The former advisor, Andrew Komarow, was known in the industry for working with special needs families and neurodivergent clients.

SEC Fines TIAA Unit $2.2M for Violating Reg BI

The SEC said a TIAA broker-dealer charged some retail customers too much to invest in mutual-fund choices in an IRA.