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Forget The Old Definition of Retirement And Define Your Ideal Lifestyle

In my work as The Retirement Coach, I make it clear to our members: our goal is not to get you to stop working. Our goal is to get you situated so you never have to work—or do anything you don’t want to—ever again. A truly relaxing retirement is one in which you do whatever you want with whomever you want where, when, and however you want with no anxiety about money. Your ideal retirement is customized to your ideals.

For some people, that means quitting work the next day, but many end up staying at their jobs because they love what they do. Many, with no financial necessity driving them, keep doing their work but stop going into the office every day. They work from home or from their second house down south during the winter.

Others go half time. Still others completely redefine their professional lives. They leave one business and launch a completely new one, sometimes in the same field, sometimes in an entirely different one. I’ve seen an operations officer become an entrepreneur and a software engineer go to work for a theater company. But they were both doing the same thing—exactly what they’d always wanted to.

A Hybrid Retirement

Many retirees create a hybrid working retirement. They sit on boards or consult in their industries—doing so only on their own terms. They arrange their lives so they can go to warmer weather for six months a year and conduct their important meetings by phone.

They apply their business and leadership skills to charitable organizations, or they become mentors. Some hire a weekly landscaping service because they never want to do yard work again. Others mow their own grass into their eighties because they like the exercise. A relaxing retirement is one that frees you from chores and obligations that annoy you, not one that makes you give up any of the work you enjoy.

Retirement doesn’t have to mean you stop working. It can mean anything you decide you want it to, and what you want can change over time. You’re not locked into anything. You redefine what you do; you don’t retire from doing it.

Defining the Ideal Lifestyle

Drilling down to what “ideal” means to you requires that you set aside any fears and misconceptions you may have. Look at things you think are facts and question if they’re really true. Call on your imagination to paint your perfect lifestyle. Since you’re probably not going to live another ninety years, it’s crucial to get started on this process now.

Even as an exercise, it’s a massive mindset shift to go from thinking about your responsibilities and constraints to imagining your dreams and freedoms. But that’s what your savings can purchase. You prepaid then for choices now.

In our work with our members, we find it helps to ask them a slightly morbid question. We have them imagine it’s the day before their last day and ask them to reflect on any regrets they think they might have. In twenty-nine years of doing this, no one has ever told me their vision of the future includes more time doing menial work.

Try to come to this exercise without preconceived notions of what you think you can do. Resist basing your expectations on what your friends are or aren’t able to afford. Come to it with a completely different mindset. Go in thinking you can have anything you want.

Later, we’ll put a price tag on it and let The Relaxing Retirement Formula determine whether or not you can afford it all.  Because if you could, wouldn’t you like to know?

Never and Forever

We do this exercise with every new member, but I invite you to try it out for yourself at home. Think about the things you’re unwilling to miss any longer and everything you want to stop doing. List all the things you’d regret not having done. What do you never want to do again? What have you wanted to do forever but didn’t think you could?

Create a picture of your ideal retirement that’s as detailed, as exciting and inspiring as you can. Do this without putting any financial constraints on your imagination.

Don’t worry whether or not you can afford it right now, just whether or not you’d enjoy it.


The following is adapted from The Relaxing Retirement Formula by Jack Phelps.

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Jack Phelps
Jack Phelps, president at The Relaxing Retirement Coach, left a career with a large financial services firm in order to offer independent advice in the best interests of his members rather than his employer. In the twenty-five years since, he’s become an impassioned advocate and guide for people facing the complex transition from a lifetime of working hard and saving smartly to spending and enjoying what they’ve built. A college athlete, Jack knows the profound difference a great coach can make, and combines a coach’s rigor and gift for explanation with years of education and hands-on experience in finance. Jack Phelps is an opinion columnist for the CEOWORLD magazine.
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