10 Things to Consider Before Leaving Your Job

Retirement. You’ve looked forward to it for years and dreamed about what you’d do with all that free time. Now that it’s becoming more realistic for you, what do you need to consider before leaving your job to be ready for retirement?

What is your daily life going to be like without work? What questions should you ask yourself before you make the transition? As “work-like” as it may sound, creating a retirement plan can be an essential step to make this transition successful.

Here’s a list of ten things you should consider and some suggested resources to help with your retirement planning:

  • How will you define yourself? When you are working, it’s very common to identify yourself by your career. Once you stop working, will you say you are “retired,” in “transition,” or a “VIP” (Very Important Person)? You can be anything you want. Recognize that figuring out your new identity may take some time and self-reflection.

Resource: How to Retire Happy, Wild, and Free by E. Zelinski – Chapter 2

  • Who will become your community? Chances are, there are some people you work with who you like and others who you tolerate. No doubt there are some you will be happy to never see again after you retire. Being at work offers a level of social interaction and companionship that you may miss once you’ve left the workplace. You’ll need to find a way to create new connections once you retire.

Resource: How to Make New Friends in Retirement from US News, May 05, 2015

  • How will you feel about aging? It’s one thing to look forward to retirement and all that you’ll be able to do. But once you actually begin looking at retirement as a realistic next step, it can make you suddenly feel old. Where did all that time go? You can get caught up in feeling sad about your age. You may need encouragement to adopt an attitude that the best of your life is coming and isn’t in the past.

Resource: Growing Older Has Its Benefits from NextAvenue.org

  • How will your family relationships change? Will you want to spend more time with your partner or grandchildren? If one partner is already at home (or one currently works at home) how much time together is too much? Is your family expecting (or hoping) you’ll take on additional childcare responsibilities? Your anticipated “me” time has the potential of becoming more “we” time. Don’t assume all members of the family have the same expectations.

Resource: A Couple’s Guide to Happy Retirement by Sara Yogev – Chapter 8

  • Will you miss having structure? When you are working, weekends and days off usually feel very special. This is “your” time to get things done and on be your own timetable. After retirement, will you be effective managing your time — or will you even care? If you hope to write a book, exercise, volunteer, work part-time, or renovate your house, will you be able to motivate yourself to get it done?

Resource: Smart Women Don’t Retire – They Break Free by The Transition Network and Gail Rentsch – Chapter 2

  • Who will recognize you? In your profession, there is a level of recognition associated with your position. As a retiree, you may find this disappears along with any self-esteem you may have derived from your career. Many retirees struggle with this loss and often enter into retirement believing it won’t affect them. Awareness of this potential problem allows you to take steps to prevent it.

Resource: How to Manage Retirement Disillusionment from WikiHow

  • How will you challenge yourself? Work can often make you feel like you’re on a hamster wheel: you are always running towards the next goal, sale, profit, break-through or cost reduction. This ongoing cycle can be rewarding and you may measure your success by all that you have accomplished. Once work is done, you’ll need to create your own challenges to continue feeling rewarded.

Resource: What Color Is Your Parachute? for Retirement by John Nelson and Richard Bolles – Chapter 9

  • What will give your life meaning? Work can be fulfilling for a number of reasons; among other things, it creates meaning for your life. Retirement may represent your opportunity to replace work with a more rewarding method to achieve life meaning. Just what choices will you explore in the future to give your life meaning?

Resource: 7 Strange Questions That Help You Find Your Life Purpose by Mark Manson

  • How will you play? Working full-time gives you limited time for leisure activities. Family or home obligations may have further limited your choices. Once you’re retired, you’ll finally have time to take on new activities. Just what will you do with this new time to play?

Resource: Awaken Your Creativity in Live Smart After 50! by Natalie Eldridge

  • Will you move? Commute time is no longer a major factor for you once you retire. Will this be the time to move? Are you ready to make this change? Do you know where you’d like to go? If you do have thoughts about the ideal retirement location, will it allow you to do all the things you are interested in?

Resource: Enter your criteria to screen places to live at FindYourSpot.com

How will you make all these choices? We typically move from childhood, to adolescence, and possibly to college as we get our start in life. Before long we’re making choices about a partner and establishing a family. Work fits in as appropriate. It’s one choice that builds on another and they typically follow an expected sequence. When you retire, it may feel like everything in your life is up for consideration and there’s not an established path to follow.

With so many aspects of life to think about, it can feel overwhelming. You may seriously consider staying longer in your current position just to avoid making decisions. You’ll feel conflicted until you finally accept that it’s time to take the big step and plan for retirement.

Retirement Style is here to help you create a retirement plan so you are prepared for what’s next.

As Dr. Suess famously said, “You’re only old once!” How much longer do you want to work?

Many of our readers prefer to print these tips in order to take notes or have an ongoing reference. We’ve made a PDF version available here for that purpose.

Looking for more resources on achieving your best retirement? Be sure to browse our Retirement Success Series, take our retirement personality quiz, read about the retirement coaching process, or contact us below for a free consultation.


For more information on preparing for retirement and Retirement Coaching, contact Deborah Williams.

Call: 503-317-4059
Email: deborah@retirementstyle.com

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