How to Emotionally Prepare for Retirement

How to Emotionally Prepare for Retirement
Elliott Appel, CFP®, CLU®, RLP®

Elliott Appel, CFP®, CLU®, RLP®

Welcome! I'm Elliott, the founder of Kindness Financial Planning, LLC, a fee-only, fiduciary advisor located in Madison, WI working virtually with widows and caregivers across the United States. When I'm not helping people live their ideal life, I'm often cooking for my wife, playing tennis, or hiking.

Have you started to emotionally prepare for retirement?

If not, now may be the time.

It’s not enough to only prepare financially. 

I’ve met people who have prepared financially for retirement and found the beginning part of retirement a challenge because they didn’t prepare emotionally. 

Retirement is one of the few events in life where your world turns upside down. Not taking time to prepare for that change is a mistake.

Whether you are going to retire in the next few years or already retired and are trying to find new meaning in retirement, let’s talk about the ways you can emotionally prepare for retirement. 

Why Retirement Can Feel Overwhelming

First, let’s start with why retirement can feel overwhelming. 


Imagine working for thirty or more years with structure, deadlines, colleagues, compensation, and a place to be every work day.

Now, imagine that it’s gone tomorrow. 

Your first thought may be, “That sounds great! I can do whatever I want.”

That’s how many people feel. 

It can be exciting at first. You have freedom to do anything you want when you want. You can sleep in, exercise, and take a long lunch. You have the option to do all of the things you never got to do while working. 

It can also be difficult to do. It’s like starting a vacation and trying to turn off your “busy mode” and relax. Some people can do it quickly while others take time.

how to emotionally prepare for retirement - lack of structure

Whether it is exciting or takes time, eventually, the novelty wears off. 

You likely will start to find a new routine and new normal. The free time that felt abundant feels less abundant. 

That’s usually when people start trying to find meaning in their new life if they haven’t prepared, and potentially, even if they have prepared. It’s a huge transition. 

Many retirees report feeling a loss of identity. Work was a part of their identity, and it’s gone. 

Colleagues and Belonging

You may feel less useful. Nobody is relying on you to supply them with your ideas, thoughts, or progress updates on projects. 

It can feel strange being surrounded by a close team of colleagues one day and then at home full time the next. 

There is a sense of camaraderie at work and being a part of a community. When you retire, you are no longer a part of that community. If you don’t have other communities you are a part of because you’ve been mostly in your work community, it can feel like you don’t belong anywhere.

That feeling of not belonging is important to work through in order to emotionally prepare for retirement.

Not Earning Money

Then, there are the feelings around not earning money. 

Many retirees have told me that earning an income gave them a sense of purpose. In a world where we often measure our incomes, or at least our perceived incomes, compared to others, it can be a daunting task to go from earning a salary to having to say, “I earn nothing now.” 

That can be a radical shift. 

Imagine for a second that the paycheck you are accustomed to earning stops in the next pay period. You don’t receive it, and you may never again. 

How does that feel? 

For many retirees, it takes time and careful planning to determine how they are going to recreate that paycheck feel.

I help design strategies for people to get them the income they need without worrying about where it will come from. 

Even with those plans in place, it can be an adjustment to go from earning money to using assets and other sources of income for everyday spending. 

Retirement can feel overwhelming for a variety of reasons. Whether you are worried about not earning money, missing your colleagues, or the structure provided by work, it’s an emotional adjustment. 

Start Planning Early

One way to emotionally prepare for retirement is to start planning early! 

Don’t wait until you put in your retirement papers to start this process. 

Although you can and there is nothing wrong with waiting until retirement to explore these ideas, the transition may be more jarring. 

The people I’ve seen successfully transition into retirement with the least amount of anxiety and confusion have already thought about how they will spend their time, where they will get their sense of identity, and tried hobbies they plan to explore. 

If you can, do a test run of retirement. There are a few ways to do it:

  • Transition to part-time work
  • Take a sabbatical
  • Take a longer vacation 

During that time, treat it like retirement — not a temporary vacation. 

As you go about your day, think about this being a permanent reality. Who will be around? How will you spend your time? Are there old hobbies you want to pick up again?  

You may find there is novelty the first few days as you go from work mode to relaxation mode. As the novelty disappears, do you find yourself bored?

If so, you may need to think about other ways to spend your time. 

Whenever possible, it’s ideal to do a retirement test run. It won’t be perfect because there is no substitute for retirement, but you can do a mini retirement test run. 

The key is to start planning early. 

Develop Relationships Outside of Work

One of the most critical ways to start planning early is to develop relationships outside of work. 

There is a good chance, whether you realize it or not, that friends at work give you a sense of belonging. 

You probably spend 8 to 12 hours around these people every work day. That’s a third to half of your day. You probably spend more time around your work colleagues than your significant other, children, or other family members. 

How to emotionally prepare for retirement - develop relationships outside of work

Work connections are a meaningful part of life. Those connections may not entirely disappear the moment you retire, but they are changed. You can still see them, but it may only be each week or every few months. 

The social connections you had during the work day may be gone. How will you create those social connections again? 

You may even miss that person who tended to annoy you. 

Many people report that it’s challenging to develop relationships outside of work. The good news is that once you are at retirement age, there are more activities available to you that naturally set you up to meet people. 

Below are a few ideas:

  • Join a club or group (hiking, biking, fitness classes, book, religious, art, etc.)
  • Invite someone to an event or grab coffee
  • Reach out to old friends you may have not talked to in a long time
  • Volunteer
  • Get a fun part-time job
  • Attend a meetup
  • Move to a retirement community or join communities that have regular events
  • Attend other local community events (colleges often put on regular events)

Relationships don’t happen after a week. 

You may need to invest time, be friendly, and continually invite others to develop meaningful relationships. 

Create a Schedule with Activity/Exercise

Physical activity and movement are key to a fulfilling retirement.

How many stories have you read about someone retiring, spending most of their time indoors, and then quality of life declines? 

Movement is critical. 

I use physical activity and movement interchangeably because some people read physical activity and think they need to be running a 5K. If that’s you, great!

If not, walking is a great way to get movement. If you aren’t used to walking a mile, start small and build up to longer distances. 

One of the best ways to encourage yourself to walk farther is to walk in nature, new places, and with a friend. 

Walking around your neighborhood, although convenient, may not be the most interesting walk that inspires you to keep going, but if you can find a trail and friend who can chat with you as you walk, there are better odds you increase how far you go. 

I’ve seen this in my own life. 

Hiking 10 miles with a friend up a mountain is far more fulfilling and easy to do than trying to walk 2 miles around my neighborhood. 

Here are other ideas for physical activity and movement:

  • Yoga
  • Stretching
  • Muscle strengthening (lift weights, resistance bands, push-ups, etc.)
  • Gardening
  • Dancing
  • Sports (tennis, pickleball, swimming, golf, etc.)
  • Kayaking and canoeing
  • Biking
  • Playing with pets
  • Playing with grandchildren
  • Aerobics classic

Exercise can mean different things for different people. The key is to find enjoyable activities that you can do regularly that are good for your body. 

I’ve seen plenty of retired people not prioritize movement, and they become stiff, lack energy, and find it challenging to do everyday life activities. 

Movement can help delay many health problems, increase energy, and increase your independence for longer. 

Explore Other Passions and Try New Things

Retirement is an ideal time to explore new things. 

I’ve seen retirees do really cool things in retirement. 

I remember one retiree was auditing classes at a community college. Although he was a retired physician and had done years of schooling, there were other topics he wanted to learn more about. Plus, he had the opportunity to spend time around younger people and learn from them. 

Another retiree was learning to sail a catamaran. They were sailing around the Caribbean, diving, and had plans to buy a boat of their own once they felt comfortable captaining their own boat. 

Many retirees pick up musical instruments. They may have played guitar many decades ago and came back to it, or are picking it up for the first time. 

Other retirees spend it volunteering. They go to the animal shelter regularly and walk dogs. They may join a gardening club to do weeding and planting for local parks. 

I’ve known retirees that wanted to learn a second language. I remember one person who wanted to learn French to get around France easily when traveling. Others decide to learn a second language and become an expat.  

If you aren’t sure where to start, perhaps start with an old hobby. Try it again or take lessons. How does it feel now? 

If you don’t have an old hobby or don’t want to start with it, try something new. Start anywhere! 

There are plenty of activities to try in retirement. You are bound to find one you enjoy. 

Develop a Routine After the First Year

Adjusting to retirement is a big transition. It can take time. 

For those who don’t have a clear idea of what they want to do, I usually suggest seeing what happens in the first year. There is something magical about having free time and seeing what unfolds. 

You spent an entire career with a schedule. You don’t have to do that to yourself at the beginning of retirement.

Relax. Take a breath. Enjoy having an entire year of free days. 

Do things you would never get to do while you had work. Most people only get to experience the first part of retirement once. It’s the time to travel, explore, and enjoy while you are healthy. 

After a year, I normally suggest developing a routine and schedule. The first year provides an opportunity to see what should be in the schedule. This doesn’t have to be a permanent schedule, but structure is helpful.  

Without it, you may find yourself on the couch watching more television than you wanted. 

You can always revise the schedule, try a new hobby, or live somewhere else part-time. 

I’ve found that people who have a schedule with regular commitments have more of a sense of belonging. It’s usually followed by the comment, “I don’t know how I ever worked. I feel like I am busier than ever!” 

Those are the people who are making the most of retirement, and I want that for you. 

One of the best ways I see people get there is by having a schedule that includes time with friends, family, and physical activities. 

Final Thoughts – My Question for You

Emotionally preparing for retirement is not an easy task. 

One day you have work. The next, you don’t. 

The colleagues you saw everyday are no longer around, and you have the option to spend your days as you wish. 

The key to emotionally preparing for retirement is to start early, develop relationships outside of work, create a schedule with physical activity, try new things, and develop a routine after exploring the first year.  

I’ll leave you with one question to act on. 

How will you emotionally prepare for retirement? 

Disclaimer: This article is for general information and educational purposes only and should not be considered investment, financial, legal, or tax advice. It is not a recommendation for purchase or sale of any security or investment advisory services. Please consult your own legal, financial, and other professionals to determine what may be appropriate for you. Opinions expressed are as of the date of publication, and such opinions are subject to change. Click for full disclaimer.

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