4 Questions You Need to Answer to Enjoy a Rewarding Retirement

“Where do you see yourself in five or ten years?”

You’ve probably heard this question many times during job interviews throughout your career – especially from interviewers who weren’t very skillful at conducting job interviews.

One of the biggest problems with this question is that you have no way of knowing what opportunities may be available in five or ten years. At the rate technology is advancing, opportunities will exist in ten years that you have no way of envisioning today.

Still, it was better to have a career plan and remain adaptable and open to new possibilities than to have no plan at all and drift aimlessly through your work years.

You had a career plan. Now, you need a retirement plan!

The question of where you see yourself in five or ten years becomes more relevant when you’re considering how you’re going to live your life after you retire.

Thanks to our increasing lifespans, it is now possible to enjoy retirement for thirty years or more – which is almost as long as your career! Your retirement could easily comprise one third of your life. Don’t you think it makes sense to have a retirement plan?

To be clear, I’m not talking about a financial plan. Of course, you need a financial plan too, so that you can be assured that you’re saving enough money while you’re working, and that you don’t withdraw money too quickly after you retire.

I’m talking about a plan for what you’re going to do with your life after you retire.

You probably set career goals. You created a professional identity. You developed a set of skills and pursued the right training and experiences that would allow you to reach your career goals.

No doubt your career goals changed throughout the course of your career, due to a variety of factors. Still, they provided direction for your next steps forward. Without any career goals, you would have languished in the same job for years, or drifted from one unsatisfying job to the next.

Just as your career plan changed over time, your retirement plan will change too. 

Create one anyway!

My retirement plan changed within a year after I retired. One element of my retirement plan was to teach presentation skills courses and offer presentation coaching. That business never gained traction and it went nowhere.

But thanks to two of my best friends who asked me to officiate their wedding, I discovered a new use for my public speaking skills as a wedding officiant. That has been rewarding and profitable, and I ended up doing that for over five years.

You may be tempted to simply view retirement as a giant chill-out. That’s fine for the first few months. But after a while, you will find yourself becoming depressed and unhappy if your life has no focus or purpose.

If you are working, you may still be entertaining the fantasy that retirement is like a full-time vacation. It’s not. Even if it was, a full-time vacation would lose its allure once it became the day-to-day norm.

The realities of daily living, such as grocery shopping, cooking, cleaning house, and paying bills will remain with you even during retirement. Sorry if that bursts your bubble.

After you leave the work world, your life is truly your own. 

Now what are your life goals? What is your personal identity? What experiences would you like to have during the rest of your life?

You may have found it necessary or advantageous to develop a work persona in order to fit into your work culture. If you are a minority of any kind, be it gay or lesbian, a religious minority, a racial minority, a person of a different nationality, or a woman in a male-dominated environment, you probably became very skillful at adapting your persona in order to succeed.

You probably value your professional network and your sense of peer recognition and accomplishment. If you are (or were) in a management role, you are accustomed to being able to delegate work to others and provide leadership and organizational direction. Having people depend on you bestows a sense of importance and responsibility.

If you have heavily invested yourself in your career, perhaps your life goals were the same as your career goals, and your work identity became indistinguishable from your personal identity. But once your career comes to an end, then what?

The two most important days in your life are the day you were born … and the day you find out why.

You will be happiest if you create some new goals for your life and rediscover or reinvent yourself on your own terms.

As you approach retirement (or if you already retired) and you start anticipating the remainder of your life, here are several questions you might want to consider.

1. Looking back on your life up to this point, have you done all the things you wanted to do?
What haven’t you done yet?

2. Over the years, what sacrifices have you made in order to satisfy the demands of work and advance your career?
What can you recover or make up for now?

3. What rewards, both material and psychological, have meant the most to you during your career?
How will you feel when those rewards are no longer forthcoming?
What will provide you with purpose and meaning going forward?

4. In what ways does (or did) your work persona differ from the real you?
Are there elements of your work persona that you miss, or will miss?

I highly recommend having a plan for the first year of your retirement, and updating it at the beginning of each new year. Take into consideration ways that you can address some of the issues presented in the questions above.

If you are married, work on this together with your spouse.

If possible, create a five year plan or even a ten year plan. It may be a lot more open-ended and flexible, but it will help you formulate plans such as moving, taking vacations, or starting a new business.

You may not be able to create a plan for thirty years of retirement. I suppose you could, but there will be so many changes to your life and to the world that this may not be feasible. But a worthwhile five or ten year plan should be well within reach.

People are not happiest when their problems have disappeared and their life is nothing but carefree recreation. Life isn’t like that anyway. People are happiest when they have purpose and meaning in their lives, and they are finding fulfillment by pursuing their passions.

What does that look like for you? Please feel welcome to comment below.

This topic is explored in greater depth in my book Smooth Sailing Into Retirement. This book will guide you from your last few months of work through your first year of retirement. It identifies the many ways your life will change and prepares you for the emotions you may experience along the way. You will learn how to design your new day-to-day life in a way that will reflect your passions and interests. You will be inspired to create a new identity for yourself that embodies the way you plan to live in retirement and frees you from the limitations of your former job title.

Click here to learn more | BUY IT NOW!

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© 2015 Dave Hughes.  All rights reserved.

Photo credit: Alejandro Escamilla

3 Responses

  1. Marilyn says:

    My retirement kinda snuck up on me and then evolved over the years, and now I find myself enjoying activities and processes I never expected – but ultimately it’s all been good! Even the stuff you CAN make plans for, like finances and friendships, can surprisingly change in the twinkling of an eye!? But that doesn’t mean we shouldn’t face these questions and try them on for size! The biggest way my working persona differs from me-in-retirement is…. (drum-roll!) – I used to curb my language when I had a job or gig, and now… I just let it rip! 🙂

  2. William DeyErmand says:

    This has been the hardest decision for me. I finally decided I would seek part time work, in business for myself preferably, until I can physically no longer work. I need that sense of responsibility of being the bread winner. Seems the part time jobs are very hard for older people to get, so I am reviewing all options of things I enjoy doing.

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