When Should I Retire? With Steve Lopez

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[130] – Are you excited to retire, or are you a little reluctant? Whatever your stance is, you shouldn’t retire until you’re both financially and mentally ready.

In this episode, Jeremy Keil speaks with Steve Lopez, best-selling author and Los Angeles Times columnist, about how to answer the question, “When should I retire?”. Steve shares examples from this book, Independence Day: What I Learned About Retirement from Some Who’ve Done It and Some Who Never Will, and the individuals he interviewed when writing it.

Steve discusses:

  • Why what you do is such a big part of your identity
  • His pros and cons list to retirement 
  • The importance of going where life is and doing whatever provides fulfillment 
  • The various huge life adjustments that come along with retirement 
  • And more

How Do You Know When It’s Time To Retire?

We talk about the various ways you can prepare to retire financially throughout our podcast episodes and blog posts, but you also have to be mentally ready to enjoy retirement. Read on to learn how identity, pros and cons of retirement, fulfillment, and big life changes all contribute to being ready for retirement.

Renew Your Identity

Many people identify with what they do for a living.

If a nurse, bank teller, police officer, teacher, author, psychologist, etc., retire, they lose their title and need to find a new identity.

So, after 50 years of working in your field, who will you be? Having a clear idea of who you are and what you want to do when you retire is crucial if you decide to leave your profession.

Steve Lopez, a best-selling author and Los Angeles Times columnist, shared the same anxiety about who he would be and what he would do if he stopped writing and retired. His hesitancy led him to interview a variety of people who were either hesitant to retire, ready to retire, or already retired. Based on what he discovered, he wrote a book about determining if you’re prepared to retire called Independence Day: What I Learned About Retirement from Some Who’ve Done It and Some Who Never Will.

Create A Pro & Con List

A lot of people might begin with a pros and cons list of retiring to determine whether they’re ready to retire or not.

Considerations about why you should retire include:

  • You’ve worked long enough already
  • Being young enough to do the things you want to do when you retire
  • Not having to deal with deadlines or stress from work

Following this list is a list of considerations for why you shouldn’t retire:

  • If you enjoy working
  • If you’re not yet financially stable and ready
  • If you feel like you should retire only because you you hit a certain age that society says you should retire

The most impactful summary of the retirement decision Steve shared with us is from a pen pal he met at a Los Angeles retirement community who said to get out while you can and do things while you’re young enough and healthy enough to enjoy them.

So if you have a bucket list for retirement, don’t let a pros and cons list hold you back from being able to experience and enjoy your retirement, but it’s a good place to start when you’re making your decision.

Seek Fulfillment, Not Just Happiness

Along with the pros and cons list, an important thing to consider when you decide if you’re ready to retire is fulfillment.

When you retire, where will you get your fulfillment?

For many, their career gives them a source of fulfillment, for others, their family does. Whether it’s a hobby, your family, or your job, you need to identify what makes you feel fulfilled before you retire to help ensure you have an enjoyable retirement.

If you have an idea of what you think you want to do when you retire, but aren’t sure if it will give you the same satisfaction as you have right now, the best option is to have a test run.

If you can sample the dream, you might find that it’s exactly what you want to do when you retire and help confirm your decision, or you might discover that it’s not what you thought it would be like. In that case, it gives you a little time to tweak and change your plans before you dive into being fully retired.

Retirement Is A Series Of Big Life Changes

Whenever you retire, everything changes, including your relationship with friends, colleagues, and your family who will get to spend more time with you than they ever did before.

These adjustments can be difficult for a lot of people. You might be ready to retire but your spouse might not be ready for that change, so you’ll have to figure out what to do with your newly-found time.

Another significant change many people struggle with is the shift from being a saver to becoming a spender.

A common source of anxiety about spending the money they saved their entire lives is not knowing if it will last them throughout their retirement. 

There are many variables that can affect this, such as your life expectancy, medical expenses, and how you spend your money in your retirement plan. If you’re worried about calculating an accurate life expectancy for your retirement plan, check out our episode The Biggest Risks To Your Retirement (Part 1): Longevity.

Speaking with a financial advisor and building a secure retirement plan can help ease these anxieties and make your transition from a saver to a spender a smoother one.


To learn more about retirement, check out the resources below!

If you have any questions, feel free to contact us or our guest, Steve Lopez, using the contact information provided below!


Connect With Steve Lopez:

Connect With Jeremy Keil:

About Our Guest:

Steve Lopez is a Los Angeles Times columnist, four-time Pulitzer Prize finalist and best-selling author. He has been a columnist for Time magazine, the Philadelphia Inquirer, San Jose Mercury News and Oakland Tribune, after beginning his career in 1975 as a sportswriter. He is the winner of more than a dozen national journalism awards, including the H.L. Mencken, Ernie Pyle and Mike Royko awards.

Lopez has written three novels and a best-selling non-fiction book, The Soloist, a New York Times bestseller and winner of the PEN USA Award for Literary non-fiction. The book was the subject of a Dreamworks movie by the same name. His latest book, Independence Day: What I Learned About Retirement, from Some Who’ve Done It And Some Who Never Will, is scheduled for publication in September.



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