How Do I Figure Out Who I Want to Be After I Retire?

You’ve spent decades being the person people call for important decisions. Now retirement is one, two, maybe three years away, and the financial plan is coming together. Yet a quiet question keeps surfacing, often when the house is still: How do I figure out who I want to be after I retire?

If that’s on your mind, you’re in good company. A helpful place to start is determining the kind of person you want to become before you start filling the calendar.

This is for executives, business owners, and senior professionals who’ve worked through the money side, but still can’t picture an ordinary Tuesday after their career ends. Without the title, the structure, and the clear purpose a career gave you, it’s natural to feel uneasy. Some people quietly worry that leaving work also means leaving behind their community and their sense of self.

Thinking about these questions well before your last day at work is worthwhile.

Preparing for retirement means thinking beyond income and investments. Considering what will replace the structure, relationships, and sense of purpose your occupation has provided is also important.

Danton Troyer, Kyle Luetters, and Thomas Auffenberg, founder of The Next Chapter Institute, have seen how these questions can affect people approaching the end of a long career. Their perspectives offer a useful starting point for planning what comes next.

Is it normal to feel lost about retiring even if my finances are fine?

Yes, and it may be more common than you think.

Danton Troyer notes that people often underestimate the retirement transition and the loss of identity, even after their financial plan is in place.

Most clients come to his team with money questions. One he hears all the time: “I’ve always gotten a paycheck. How do I get a paycheck after I retire?”

That question has a planning answer. Turning savings into income is familiar ground for a retirement planner. But Danton has noticed that once those pieces are in place, other questions are still lingering.

As he put it, there are “all these little things like, ‘What do I do every day now that I can?'”

So if the numbers look sound and you still feel unsettled, you simply have another important part of retirement to consider.

Knowing you can afford to retire doesn’t necessarily tell you what you want retirement to look like.

How do executives deal with losing their identity in retirement?

Thomas Auffenberg knows this ground personally. He taught high school, practiced law for about 12 years, and then owned a business for 25 years before selling it in 2016.

Since 2017, he’s led a program for people nearing retirement or recently retired.

He says the people who join the program tend to be successful and busy. Many are executives and business owners. Others are doctors, lawyers, accountants, engineers, and professors.

By his estimate, about 35 people a year go through the program in St. Louis, with a similar number in St. Paul, Minnesota.

The worries he hears are remarkably consistent. Common non-financial retirement concerns include loss of identity, loss of community, boredom, health worries, lack of structure, and lack of meaning and purpose.

• Identity: For years, your role answered the question, “What do you do?”
• Community: Colleagues provided daily connection through your working life.
• Structure: Your calendar was largely decided for you.
• Purpose: Your professional responsibilities gave you a reason to get up each morning.

Naming these concerns is the first step.

Tom has also seen how much it helps to face the concerns alongside others. Year after year, he says, participants tell him how glad they are that they went through it with people facing the same transition, “rather than just trying to go it alone.”

What should I do with my time after I retire?

Most people start with this question.

Tom, founder of The Next Chapter Institute and author of Discerning Retirement, says most participants start out focused on filling their time, but eventually become more interested in who they want to become. The pattern is worth noticing.

Tom asks early in his program: How many people joined mainly to figure out how to fill all their free time?

Why does the time question feel so big?

Thomas points out that for people with adequate financial resources, reasonably good health, and no significant caregiving responsibilities, retirement brings “probably the most radical freedom you’ve ever had in your life.”

Then he adds:

“And that can be daunting.”

After decades of full calendars, all that open space on a blank page is alarming.

Many people approaching retirement assume their main challenge will be filling their free time, but a deeper question is who they want to be in their next chapter.

How do I find purpose in retirement after a long career?

Tom suggests a different starting point before asking what you’ll do. Ask yourself:

What kind of person do I want to be in my next chapter?

He describes it as “more the being question than the doing question.”

And he says the being question “really helps answer the doing question.”

For example, someone who wants to be more generous might begin looking for ways to share their time or experience with others.

Say you decide you want to be more generous with your time, talent, and treasure. Or more patient. Or, for some people, more prayerful.

Each answer starts to shape your days.

Deciding who you want to be in retirement guides how you choose to spend your time.

Tom has also seen purpose influence other areas of retirement. Finding a sense of purpose may help reshape your identity, create new opportunities for community, and ease concerns about boredom.

He also suggests that having a purpose may support overall well-being, although individual health outcomes depend on many factors.

If you’re working on finding purpose in retirement after a long career, the following questions may help turn common concerns into personal reflection.

If you’re worried about…A question to reflect onHow your answer might shape your daysLosing your identityWho do I want to be known as now?Points you toward roles that fit that personLosing communityWhat kind of friend, neighbor, or mentor do I want to be?May lead to groups, service, or hobbies to share with people who have similar interestsBoredomWhat do I care about enough to devote time to?Helps you choose meaningful commitmentsLack of structureWhat rhythm helps me feel like my best self?Shapes a weekly routine you choose intentionallyLack of purposeWhere can my talents serve others?May point to volunteering or new kinds of workGetting too busyWhat does a balanced life look like for me?Helps you decide when to say yes or no

What do I do every day after I retire?

Once you have a sense of who you want to be, daily life gets easier to picture.

But Tom raised one more point that’s easy to miss: balance.

“People can get as busy in retirement as they were in their work life.”

Many high-achievers fill every open slot and lose the balance they hoped for.

His suggestion is to decide what balance you want first, then build your days around it.

A few questions may help:

• How much of my week do I want to give to family, service, rest, learning, reflection, and fun?
• What will I say yes to? What will I turn down?
• What daily rhythm would help me feel steady?

Tom offered an example.

Someone might decide to give 25% of their time to a significant volunteer activity. That’s a clear decision. But figuring out which activity, exactly, can take real work.

The point isn’t to fill every hour, but to decide what deserves a place on your calendar.

When is the right time to start thinking about the non-financial side of retirement?

Tom usually works with people one to three years from retirement, or one to two years past it. He’s noticed that people who have been retired for five or 10 years can become more set in their ways and less open to a fresh look.

Starting while the transition is still ahead of you gives you more room to shape your retirement in a way that will be fulfilling to you. Allow yourself time to consider how you could implement various priorities in ways that you value and enjoy.

What does a Next-Chapter Plan actually include?

Tom’s approach focuses on several areas:

• Self-awareness: Looking honestly at your talents and identifying which common retirement challenges may affect you most.
• Thoughtful decisions: Making important choices slowly, with time for personal and spiritual reflection.
• A written draft: Everyone who completes his program leaves with a draft next-chapter plan.  Tom notes that, like a financial plan, this will need to change as life unfolds.

Tom describes his program as a spiritual journey, grounded in Ignatian spirituality, a tradition associated with St. Ignatius of Loyola, who founded the Jesuits.

Participants are encouraged to pray daily and use a reflective decision-making process called Ignatian discernment.

When Kyle asked how a diverse group responds, Tom explained that most participants are Christian and that daily prayer tends to become part of their practice over time.

He was also clear that his program is a good fit for people interested in a spiritual approach, and probably not for those who aren’t. While faith-based retirement planning will resonate for some professionals, others may prefer to reflect on their next chapter in a different way. Regardless of the religious aspects, the basic focus areas – self-awareness, thoughtful decisions, and drafting a plan – can help anyone consider who they want to be in retirement.

How do I actually stick to a retirement life plan?

A plan on paper is a start.

Putting it into practice takes ongoing attention.

After Tom’s program, participants often form small implementation groups of about three people.

These groups choose their own parameters and may meet monthly to help members turn their written plans into action through brainstorming, encouragement, and accountability.

An accountability group for retirement goals doesn’t have to be formal. A few trusted people in the same stage of life, checking in once a month, may be enough to help you revisit your priorities and follow through.

How does my financial plan connect to the life I want?

Tom’s program doesn’t cover finances; he expects participants to have that side handled with a financial planning firm.

Danton sees the same transition from the other side.

A financial plan can be more personally relevant when it supports a life you’ve actually pictured.

When you know who you want to be, conversations about retirement income, charitable giving, and timing can begin with what matters most to you.

No plan can guarantee how things will turn out, and concerns about outliving your savings can linger even when the numbers look reasonable.

Those worries are worth raising openly with your financial planner, alongside the bigger questions about your life.

Frequently Asked Questions

I’m a business owner retiring in two years, and my financial plan is in place, but I can’t picture my days. Where do I start?

Many people in your position find it helpful to start with who they want to be before deciding what they’ll do.

For most people, two or three years before retirement may be a useful time to begin reflecting.

Questions about generosity, patience, relationships, and balance can help you picture a daily rhythm.

Talking through these ideas with your family, trusted peers, and financial planner so your financial decisions support the life you envision.

What questions should I ask myself before retiring besides whether I have enough money?

Some questions to consider include:

• What kind of person do I want to be in my next chapter?
• Where will I find community once I leave my colleagues behind?
• What structure or rhythm helps me feel steady?
• Where can my talents serve others?
• What does balance look like for me?

Your answers may differ from anyone else’s, and that’s expected.

How can I shift from filling my time in retirement to thinking about who I want to become?

Try asking the “being” question first.

Instead of listing activities, describe the person you hope to be, such as more generous, more patient, or more present with family.

Then consider which uses of your time fit that person.

Tom observes that while most people in his program start out focused on filling time, many end up focused on who they want to become. That answer often helps them decide how to spend their days.

What emotional challenges do executives face when they retire, and how do people work through them?

Common concerns include loss of identity, loss of community, boredom, health worries, lack of structure, and lack of meaning and purpose.

People can work through these concerns by identifying them early, reflecting on who they want to be, and talking with others experiencing a similar transition.

Many appreciate going through this process with a group rather than trying to figure everything out alone.

How can a small accountability group help me stick to my retirement life plan?

A written plan often requires additional work to put into practice. A small group of two or three peers who meet about once a month can offer a place to brainstorm, share encouragement, and maintain accountability.

For example, if you decide to devote a portion of your time to volunteering, the group may help you consider which specific activity fits your interests and values.

Regular check-ins can provide an opportunity to revisit your commitments, discuss challenges, and make adjustments as your retirement unfolds.

Continue the conversation

You may know when you want to retire and how you’ll pay for it. But what will make those years meaningful to you?

That’s a question worth exploring while you’re still working. Knowing who you want to become can help you make better decisions about how to spend your time.

In this episode of Wit, Wisdom, and What Matters Most, Danton and Kyle explore that transition with Tom, including the role of identity, community, purpose, and personal reflection.

Are you preparing for retirement but still wondering what your next chapter will look like? The Gast Freeman Troyer team at Moneta can help you align your financial decisions with your personal goals, values, and vision for the future.

Ready to start planning a retirement that reflects what matters most to you? Connect with Danton Troyer and Kyle Luetters to discuss your retirement goals, and listen to the full episode for more insights on finding purpose, identity, and fulfillment beyond your career.

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