Is "Retirement" the Only Answer? Take Time to Rethink the Possibilities

As a financial advisor, you would think I’ve seen a million definitions of retirement. What’s surprising to me is that I haven’t! In fact, not all, but certainly most of the people I work with tend to see retirement as an absolute goal and an endpoint. That’s why I’ve made it one of my primary goals to break that definition wide open and help every client rethink their possibilities.

At 52, Leslie is well into a very successful and lucrative career in aerospace. When we sat down for her financial review last summer, she hit me with the question almost before I’d said hello: “When can I retire?” I was taken aback for a moment. The last time we’d talked, she’d seemed satisfied with her job, and she was bursting with excitement about a new project she was working on at the time. “You’re only 52 Leslie,” I said (with just a little envy!). “What’s the urgency?”

She slumped back in her chair, and every part of her seemed to collapse. “I’m just so tired of it all. The corporate craziness. The fighting for each new project. The hamster wheel. I love the actual work , but I don’t know how much longer I can stand the process I have to go through to roll up my sleeves and just do my job.”

Anyone who has ever worked in the corporate world can commiserate.


But I’ve known Leslie for years, and she looked and sounded like she was truly at the end of her rope. Suddenly what I expected to be a pretty eventless review meeting was carrying much more weight.

The first thing I did was look at the numbers, and they looked pretty good—so good, in fact, that my calculations showed that Leslie could realistically retire in just two years, at age 54. For many, that would be a dream come true, but I knew that for someone like her, it could be a recipe for discontent, if not downright disaster. So I started asking some important questions. I didn’t focus on budgets or savings or future expenses. What I wanted to explore was what she wanted the next 50 years —or even the next 10—to look like. Here are just a few of the questions I asked:

If you aren’t going to an office every day, what do you see yourself doing—every day?

Do you see yourself living in the same place you are today? Do you have a dream destination?

How do you socialize? Are most of your friends work colleagues, or do you have other circles of friends? What about extended family? When and where do you get together?

What activities do you do outside of work? Is there anything you do that might become a second career?

Are you active in any charitable work? Do you volunteer?

You seem to love what you do. Is there a way to transfer your skills to another organization? Would you be interested in teaching?

If not, will you be happy not doing the work you’ve been passionate about for years?

Is there something else you love that could replace that passion?

If you could have chosen a different career, what would it have been? Is there anything you’ve always wanted to explore but never had the time to pursue?

As we sat sipping our coffees and chatting, I didn’t maneuver Leslie’s thinking; I just worked with her to paint her picture of her future. Her frustration at the office had prevented her from looking beyond her “day job.” At first, this type of “playing” wasn’t easy. Toying with the ideas felt like breaking out of a well-sealed box. But once she got there, we were suddenly onto something! “I’ve always wanted to write,” she confessed. “Not a novel or anything like that. Not fiction. But I’ve never seen a textbook that clearly explains the concepts we use every day in aerospace engineering. It’s this vacancy of information that would be so valuable for anyone entering the field.”

As soon as the words were out, everything about her seemed to change. She was literally on the edge of her seat, her eyes were bright with excitement, and her voice was as happy and clear as the last time we’d met when she had gushed about that old project. What a transformation.

It’s been a year since that meeting. On the surface, not much has changed. Leslie is still working at her job in aerospace. She’s still frustrated with corporate politics and the battle for projects. Yet her outlook has changed dramatically. She is planning to leave her job next year, and she’s headed for anything but a traditional retirement. After our talk, she began to research the process of writing a textbook. She shopped around a proposal to multiple publishers, and one has already expressed interest in her book. It’s a long, multi-year process from proposal to publication, but Leslie is well on her way to making her “retirement” dream come true.

No matter how near or far retirement is for you, I invite you to take a good look at yourself—your goals, your passions, your dreams—and rethink how you envision living your own retirement.


And no matter what size your nest egg may be when the time comes, I hope you make choices that bring the most thrilling opportunities to life.