I once sat on a finance committee with the CEO of a large brokerage company. In one of the meetings, we did an icebreaker with the question, “What one skill do you wish you had?” I was 29 at the time, while the CEO was closer to 59.
I was remodeling a little condo my wife and I had just bought. The CEO looked at me and said, “I don’t know how to swing a hammer. I can’t do what you’re doing.” He had bought 500 acres in upstate New York and wanted to learn how to swing a hammer.
He already had the 500 acres. What he was talking about now was what he wanted to do there. He wanted to learn to swing a hammer and build something himself.
Here was a man running a large brokerage company, interested in becoming a beginner at something I was already doing in my little condo. The money had bought the land. It couldn’t do the learning for him.
And that is where the retirement conversation needs to go next: beyond what you can afford to have, to what you actually want to get up and do.
In the last article, we worked through what goes into figuring out whether you have enough money to retire. The travel, the house, helping family, the everyday spending, and the conversations that need to happen when your spouse has a different picture of retirement than you do.
Now let’s say we have done that work. Your financial plan supports retiring, based on the spending, income, and assumptions we have worked through. There is still another question to answer.
What are you going to do Monday?
Not the Monday when you board the plane for the trip you have been putting off. The one after you get home. There is no office to go into. No co-workers to talk with about the weekend. The problems that used to land on your desk are landing on someone else’s.
What does that day look like?
What Are You Actually Leaving?
In the first article, we spent time figuring out what it would take to replace your income. But the paycheck isn’t the only thing you have been getting from work. There are people you know, problems you have learned to solve, and responsibilities that give some shape to your week. You may complain about parts of it and still care quite a bit about others.
We can have a plan to replace the income without having a plan for any of that.
Some of the comments I hear from clients approaching retirement are, “My friends and colleagues are at work,” or, “I like the challenge of work. The idea of sitting at home doesn’t appeal to me.” Others like the routine. Those aren’t financial objections. They are telling me something about the life they don’t want to lose.
Think about the person who is tired of the pressure but still enjoys solving a difficult problem. Or someone who is done with the commute but looks forward to seeing the people at the other end of it. They can be ready to leave the job and not be ready to give up those parts of their day. That isn’t a contradiction. The problem is that, up until now, those things have all come together.
This is where the word “work” can get in our way. We use it to describe earning a living, but also teaching someone, building something, helping solve a problem, or taking responsibility for something we care about. When we say we are done with work, are we talking about all of that? Or are we talking about the particular job we have been doing, with its particular demands?
I’ve watched several women I know, including my wife, return to the workplace, not because they needed to, but because they wanted to. They went back to do something different than before. What they found was a new challenge, a sense of purpose and belonging, and structure.
Going back to work by choice is quite different from having to go back because you need the income. Being able to stop earning a paycheck doesn’t mean you have stopped wanting what else a job might give you.
And maybe you are reading this thinking you won’t miss your job at all. You already have friends outside of work, interests you want more time for, and people you want to spend that time with. Or you are worn out and need some room to breathe before deciding what comes next.
I am not suggesting you immediately fill every empty hour with another obligation. We are trying to understand what you want your life to contain, not recreate your work schedule without the pay.
So I would ask two questions together:
What am I ready to leave, and what would I be sorry to lose?
Put those answers next to each other. You might be ready to leave the deadlines but still want a challenge. Ready to stop managing a department but still enjoy helping someone learn. Ready to leave the office but not the friendships.
Now we have something more useful than “I want to retire, but I’m not sure I’m ready.” We can start looking for ways to leave what you are finished with while finding other places for what you still want.
Getting Those Things Outside of Work
I have a longtime family friend who retired from being a fireman. For years, he has volunteered with a couple of different programs related to dogs. That is where he found community, but he also found a challenge, new learning, structure, purpose, and friends outside of work.
You could describe what he did as “volunteering.” But that one word doesn’t really explain all that he found there. Look back at the things people tell me they will miss about work. Quite a few of them are on his list.
I come back to three things: health, community, and purpose.
The trick is to find things that bring more than one of them into your life. You don’t necessarily need a separate activity for every box.
I also have a client who, while still working, was already hiking all over the place with her hiking group. There is an activity she enjoys, people to enjoy it with, and something that gets her moving. She didn’t have to wait for retirement to start finding that part of her life.
This is also why I don’t think “go volunteer somewhere” is a complete answer. I have known people who volunteered only to find that the particular commitment created stress and anxiety. The organization and the role need to fit you. A good cause doesn’t automatically mean every job within it is the right job for you.
What Have You Wanted to Learn?
When my grandma retired, she became a regular at the local junior college. She took everything from poetry to painting. I think she ended up with about 70 units in art and writing classes.
What have you wanted to learn that has nothing to do with what you have done for a living? Is it something as simple as learning to swing a hammer? Or perhaps there is a part of your profession that you always enjoyed but rarely had enough time to explore.
There is another direction to consider, too. What do you already know that might be useful to someone else? Could you teach it?
You may be ready to stop doing your particular job without wanting to leave behind everything you have learned along the way.
Start With Something Small
When I coach, whether it is kids on the soccer field, young people starting out, or people preparing for retirement, I like to find the “easy wins.” Those are the ones that build confidence.
With retirement, we can start identifying what connects you to work and gradually find other places for those things in your life.
That is the idea behind the work-satisfaction exercise in my retirement material. We look at what work provides: identity, contribution, learning, structure, purpose, community, challenge, routine, and friends. Then we identify which of those things matter most to you.
Here is a place to begin:
- Write down what you would miss about work. Be specific. “The people” is a start, but is it the friendships, having someone to solve a problem with, or simply being around others during the day?
- Put a possibility next to each one. An actual class, group, organization, or person, not just “I’ll get involved in something.”
- Try one before you retire, where practical. Go to the class. Meet the group. Find out what the volunteer role involves. See whether you enjoy the activity and the people.
You can start this exercise after retiring, too. You are not committing the next 20 years of your life to the first thing you try. You are learning something about what you want your days to contain.
And if you are married, compare notes with your spouse. Just like the spending exercise in the first article, you may discover you have been imagining different things. What will you enjoy doing together? What will each of you do independently?
Your spouse may already have a routine they like. Your retirement needs to make room for that, too.
Back to Monday
I often describe money as banked time. Part of what we are doing when we save for retirement is trying to reach a point where our savings and other income can support our lives without our having to keep earning a paycheck.
But that still leaves the question of what we want to do with the time that is now available to us.
Travel belongs in that picture. So does rest. There is nothing wrong with enjoying the things you worked and saved for. But alongside those plans, think about the people you want to spend time with, the things you want to learn, and the responsibilities you would actually like to have.
One of the questions in my retirement material is, “You are more than what you do at work. Who else looks up to you, relies on you, and wants your connection? Why?”
Spend a little time with that one.
Then look back at the parts of work you would miss and the things you have been saying you will get around to someday. You don’t need every day figured out before you leave. But you should be starting to see a life outside of work that you would like to move toward.
So, what would you like to do Monday?
Once that picture starts taking shape, we can come back to the money with a better understanding of what we are asking it to support. And if the life you have in mind costs more than you expected, the conversation doesn’t have to end at “save more” or “spend less.”
There is another question to work through:
Are we making the best use of what you already have?
In Part 3, How to Make Your Retirement Number Go Further, we’ll look at the planning around taxes, income, and how you draw from your savings. Not to pretend that every item on the wish list can fit, but to explore whether different choices could make more of it possible.
We have talked about having enough and what you want to do with it. Now let’s look at how planning can help what you have support more of that life.
This article is for general educational purposes and is not a recommendation that any individual retire or change an investment strategy. Retirement decisions depend on personal circumstances and planning assumptions, which may change over time.