Retirement Q&A: 3 Reasons Why You Shouldn’t Retire

by | Aug 5, 2019 | Retirement, YouTube

Key Takeaways

The timing of your retirement is perhaps one of the most important financial and life decisions that you will make. Period. The timing decision about when you retire has a tremendous ripple effect on your financial situation, psychologically and your health.

And a lot of times the clients will ask me, Ashley, when can I retire? But the question that I am never asked, almost never asked, which I am covering today, is why shouldn’t I retire?

In today’s video, I’m discussing:

  • Why your 60’s are the new… well, whatever you want them to be when it comes to your retirement age.
  • What no one is telling you about post retirement.
  • The benefits of extending your retirement age – work longer, live longer!

Click here to watch the full video or read the full video transcript, below.


I think all of us eventually want to stop working and transition into retirement. And I don’t think that a lot of clients and a lot of people I talk to consider the financial aspect of “do I have enough money to retire?” But as I’m going to talk about in today’s video, there are a lot of reasons why you might want to keep working.


Reason number one, why you shouldn’t retire, is that you truly enjoy your work! I had this happen several times with clients where they get to their early to mid-60’s and they start thinking about retirement because isn’t that what you do when you’re in your 60’s? Right? We should stop working.

There are still people who cannot physically work. They have a very physically demanding job and they get to their early sixties or late fifties and they’re just done. But if you sit at a desk and your work involves your mind, thinking and solving problems and doing those things, we can work now a lot longer.

I recently saw an article in the New York Law Journal about an attorney in New York. This guy is 106 years old and he is still practicing law. In fact, I think he only goes into the office a couple of days a week. He had to scale back after he got pneumonia a couple of years ago and it really threw him for a loop on his health there.

But this is a guy who is 106 years old. He’s one of the founding partners of the big law firm in New York and he still goes to work. I’m pretty sure he just chats with people in the office. I don’t think he’s doing a lot of work, but his work is still meaningful to him. It gives him purpose and he enjoys work.

I think a lot of people feel this pressure that they must retire when they can because they can. But keep in mind that for Americans today, for most of us, we derive a lot of our personal sense of identity from our work. And so, if you really enjoy your work, you love what you’re doing, there’s no reason why in a lot of cases you should retire.

Reason number one, why you shouldn’t stop working is, you enjoy your work. Keep working if that’s you!


Reason number two why you shouldn’t stop working, has to do with your vision that you have for retirement. What I mean by this is, if you are getting close to retirement, you should have a very clear vision of what retirement is going to look like for you. How are you going to spend your time? What are you going to do? What are you going to do to replace the 40 hours of work that you were doing before?

A big problem, that is very prevalent for a lot of Americans that most people don’t realize is, depression and anxiety can set in about 6 to 12 months after you have transitioned in to retirement. After the initial- Woo! I retired, and the luster of retirement wears off, is when a lot of people become bored and depressed because they didn’t realize that they didn’t have a vision for their retirement.

They just wanted to stop working and transition into retirement. And now that they’ve sort of cleaned out the garage, remodeled the kitchen and did all the things that they really wanted to do, because they couldn’t before when they were working, they’re like “what now?”

The takeaway here is to get crystal clear on your vision of your retirement before you transition into retirement.


Reason number three, why you shouldn’t stop working is because of the health benefits. There has been numerous studies that point to the fact that if you work longer, you will live longer. There’s a statistical significance between working longer and living longer.

And this makes a lot of sense because if you’re working longer, not only are you usually being more physically active just by working, but you’re also keeping your mind active too. Having that sort of constant training and sharpening of your mind through problem solving, reasoning and all the things that you need to do when you’re on the job every week, is incredibly beneficial for your health and your longevity.

Consider working longer if you want to live longer!


If you want to know more about transitioning into retirement, you can click on the link below and sign up to get our free white paper which covers the “5 Unexpected Things Every Small Business Owner Must Do Before Retirement.” Head over to our home page and scroll down to the bottom to sign up >>>

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Ashley helps business owners exit their business and retire with financial security. As a Certified Exit Planner she specializes in helping business owners navigate the maze of decisions that need to happen from full-time running their business to retirement.

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