Should I Retire? 9 Exercises to Help You Decide if You Should Call it Quits

Should I retire? It is a big question.

Some of us can’t wait to retire and do so as early as possible. Others are not so sure about life without work. Reluctant retirees might be worried about money or they might be concerned that they will just really miss work. The fear of missing out (FOMO) can be strong for both work and leisure.

should i retire

If you are torn between the idea of retiring and continuing to work, here are 9 exercises to help you get clarity on the big decision: Should I retire — or not?

1. Choose which quote best describes your feelings about retirement

Select which quote resonates with you. It may help reveal whether you should retire or not.

1. Sit back and relax and do the things you never got a chance to do. — Julie Hebert

2. Work is the basis of living. I’ll never retire. A man’ll rust out quicker than he’ll wear out. — Colonel Sanders

3. Retirement is not the end of the road. It is the beginning of the open highway. — Unknown

4. Musicians don’t retire; they stop when there’s no more music in them. — Louis Armstrong

5. I’ve crunched the numbers in your retirement account. It’s time to figure out who will be wearing the mask and who will be driving the getaway car. — Unknown

6. I think that retirement is the first step towards the grave. — Hugh Hefner

7. Often when you are at the end of something, you’re at the beginning of something else. – Fred Rogers

8. To retire is to die. — Pablo Casals

9. The trouble with retirement is that you never get a day off. — Abe Lemons

10. There is never enough time to do all the nothing you want. — Bill Watterson, Calvin and Hobbes

11. To find joy in work is to discover the fountain of youth. — Pearl S. Buck

12. Work saves us from three great evils: boredom, vice, and need. — Voltaire

What your quote means

If you chose quotes 1, 3, 6, 7, or 10, then you are probably ready to retire.

Did you find quotes 2, 4, 9, 11, or 12 to be most appealing? This suggests that work is where you get the most satisfaction from life and there is nothing wrong with continuing to do what you are doing.

Is quote number 5 the most meaningful? This probably means that no matter what you want to do, some kind of income is probably going to be necessary. But, remember, it doesn’t need to be nose to the grindstone! Switch jobs and do something you like doing. Explore the best jobs after retirement or retirement business ideas for after 50.

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2. Build a detailed retirement budget

Nothing will make either the financial or the lifestyle part of retirement more real for you than creating a detailed budget for the rest of your life.

Figuring out what you will want and need to spend and when is the most important part of creating a retirement financial plan.

The NewRetirement Planner makes it easy to create a detailed retirement budget. You can either:

  • Budget for different phases of retirement and set overall spending levels for different time periods
  • Build a detailed budget for how your spending will evolve in over 75 different categories, even specifying must-spend and discretionary spending amounts for better planning

Of course, you actually need an overall financial plan, but your future budget defines how much you need in savings and income.

Use the NewRetirement Planner to do better with your expenses, income, savings, investments, taxes, time, and more…

Create two budget scenarios

Create one scenario for your life with continued work. Build another for life in retirement.

Compare how you feel about the imagined life and finances in these two very different futures.

3. Think through your purpose in life

Study after study shows that defining your purpose in life is a key to happiness.

Once you have defined your purpose, then you can make a better decision about retirement or continued work. Here are a few resources to help you define meaning and purpose:

4. Consider how you feel on vacation

I have vacationed with someone who I think will never ever want to retire.

  • Luxuriating makes him antsy.
  • Activities (e.g. sightseeing, surfing, meeting new people) are an enjoyable distraction, but never where his heart resides.
  • He looks forward to going home and back to the office as much (or more) as he looks forward to getting away. (And, this after just a week. I shudder to imagine how he would feel after two weeks, a month, or more.)

If you are like this guy, then you might want to stop worrying about retirement and just enjoy what you enjoy — work, solving problems, creating value, building teams…

However, if you love vacations of any type, then retirement might suit you just fine.

5. Create a “bucket list”

Are you ready to retire? Only if you have a plan for what do you want to do with the rest of your life!

  • Do you have things you want to experience? Ride in a seaplane? Try surfing?
  • Places you want to go? The Grand Canyon? Visit all 8 wonders of the world?
  • A financial legacy you want to leave?
  • A career benchmark to achieve?
  • An accomplishment to finish? Helping people through your work?
  • Is there something you want to do physically? Run a marathon? Create a vegetable garden?

What will you regret not having done? Create your list and assess if it is more compatible with working or retiring.

6. Think about who is important to you

The decision for how you want to spend the rest of your life is yours. However, your relationships are perhaps what is most important in life.

It may be critical to your happiness to ask who is important to you and how will your decision to retire or keep working will impact your relationships.

7. Envision a weekly retirement calendar

So, pretend for a moment that you made the decision to retire. Now, imagine what the next week looks like. When do you wake up?  Whom do you meet up with and where? What do you eat? What do you do?

Try writing down a full retirement schedule for yourself for Monday–Sunday and decide if you like what you see. Assess if it is a realistic and desirable future for yourself.

8. Create a pros and cons list — including thinking about what you will regret the most

This is the classic decision-making exercise and it can really help you understand the potential impact of your decision.

A couple of things to keep in mind:

  • There is no right answer, just a right-for-you answer
  • Consider which option will cause the least amount of regret

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9. Assess what one more year of work really means

A lot of people who are on the fence about retirement keep putting it off for “just one more year.” The problem is that “one more year” often turns into 10 more years.

If this is you, explore what one more year really means.

Ready to take the leap into leisure? Or, keep enjoying the labor?

The good news? There are no right answers.

You can take the leap into leisure or you can keep enjoying labor. It is all good. And, no matter your goals, the NewRetirement Planner can help you build and maintain the financial plan that is compatible with the future you want.

Plan to:

  • Fund the retirement you want
  • Build a financial legacy for your heirs
  • Balance today’s financial priorities with tomorrow’s possibilities
  • Slowly glide into a life of leisure
  • Some combination of the above

Anything is possible with the right plan.

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NewRetirement Planner

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