Fear of Retirement Boredom | 7 Cures [Videos]

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For those planning to retire soon, retirement can feel scary from both a financial and a lifestyle perspective. 

Fear of retirement boredom is a very legitimate reality, especially for certain personalities. Here are 7 ways to address that subtle and almost embarrassing fear that you could be bored to tears in retirement.

Read my own story about retirement boredom below or scroll right down to the tips on how to avoid boredom in retirement.

My Story about Retirement Boredom

The year I turned 30, I tried to retire after working at least part time since I was 14 years old.

I had moved from the chaos of Houston, Texas, where I was working as a commercial real estate broker, to be with my new husband on the beautiful island of Bermuda. 

I knew I had a fear of retirement boredom beforehand, but I didn’t anticipate how real it would be.  I remember going for my daily walk down Harbour Road, where we lived in an amazing little green waterfront house, with tears streaming down my face.

I missed the mental stimulation, challenge and growth of work! This is when I made a definite commitment to immerse myself into learning everything I could about investing in stocks and bonds and become the family investor.

My always supportive husband was consumed with his demanding work, so this suited him fine. 

By learning how to invest, and consulting very part time, I entered an unofficial retirement. I call it “unofficial” retirement because I have always considered investing enjoyable but real work.    

Fast forward 3 decades. I still love the challenge and stimulation of endeavors around investing, small business and personal development. I’d trade a good chat about online business strategies or comparing alternative investment yields over idle chit chat any time. 

But I was truly in the depths of despair when I tried to retire early from demanding, full time work. By finally learning to accept that it was okay to actually desire at least some form of work in retirement, I found these solutions to overcome retirement boredom.  

It is from this place that I am inspired to write this post. I truly get it. But I can also say that after about 3 decades of unofficial retirement, my “unofficial retirement” work is more stimulating, rewarding and opportunistic than ever. 

If you are suffering from fear of retirement boredom, fear not. We are living in an incredible time to do or be anything you want after you retire.

Here are 7 fear of retirement boredom paradigm shifts that are sure to leave you excited to trade in your alarm clock for a fantastic retirement lifestyle.  

Investment Opportunities in Retirement

Where to begin addressing the investment opportunities in retirement?

For anyone wanting to live outside the conventional retirement plan of scraping by on less income, social security, and spending down your hard earned retirement savings with a retirement withdrawal plan, wealth building opportunities are abundant.

Someone has to manage your retirement money. Even if you hire a financial advisor or wealth manager, there are many wealth building and income generating opportunities outside their wealth management duties.

Plus, there’s staying abreast of financial news to hire a good financial advisor and monitor the job they are doing for you. While it doesn’t feel like it, that’s your job as an investor when you hire a financial advisor.  

And if you manage your own investments, there are so many wealth building strategies that also generate retirement income, such as dividend investing outside the usual funds, covered call writing and other“slightly” alternative investments such as MLP’s, REIT’s and preferred stocks.  

Serving on Boards in Retirement

Serving on boards in retirement is an excellent way to experience personal development and help others overcome challenges while making the world a better place.  By networking online, in your community, or place of worship you can find opportunities to serve on boards. 

Angel Investing

Angel investing is the way that people invested in local small business startups before the startup business craze. Many communities, like Austin, still have strong angel investing networks

Angel investors frequently get involved with the companies in which they invest. Sometimes this is more out of necessity than desire, however. 

But angel investing can be a great way to avoid boredom in retirement. Note that, in general, the rule of thumb for small business investing is 10 to 1 due to the high failure rate of small business startups which you can read more about in my article.  

Also, angel investing is typically limited to accredited investors as I explain in the video below. 

While angel investing may not be available to you, here are more ways to overcome a fear of retirement boredom. 


As an investor or as a volunteer, you can mentor someone in a skill area where you excel. This can be anything from small business marketing to teaching someone how to read or speak a second language. 

You don’t have to teach a rare or high level skill.  In my later years, for example, my dad had the rewarding volunteer opportunity of teaching a bank employee how to read, something this man had to hide in shame for years to keep his job.  

There are organizations such as Score that provide business consulting for free.  

Starting or Buying an Online Business

Starting an online business or buying an existing online business is one of the best opportunities I see today to increase income while doing work that can be very rewarding. 

In this post I explain how to choose an online business to start, so have a read or watch my video if this interests you. 

Before you think this is too alternative or difficult, let me share that online business has been our favorite income generating asset over the past 15 years. 

We never even suspected online business as a retirement option in our late 40’s and early 50’s having been previously committed to traditional retirement models in stocks and bonds and being non techies, but we love it. 

While online business has not generated entirely passive income, we enjoy the learning and mental stimulation, probably much like you if you’re here at Retire Certain.   

Offering a Service in Retirement

You can offer a service which you enjoy as a volunteer or to make money in retirement. For example, the amazing handyman who helps with our rental properties is a retired financial executive in his mid 70’s who prefers the outdoors. 

My last (and by far best) dog trainer was a retired executive in his early 50’s. He was sure expensive at $185 an hour! 

But I only needed to hire him once to get the results I wanted with Blanco vs the woman who sold me a package that didn’t work and demanded a lot of our time for all her sessions. 

There are 115 cool ideas in my post Businesses to Start Later in Life If this appeals to you, brainstorm services you could offer to help you overcome your fear of retirement boredom? 

Tackling Your Bucket List

Who doesn’t put aside their dreams for the daily grind during decades of employment and raising children? We can easily get to the point where we lose touch with what we really want to do that brings us joy during those busy years. 

What have you always wanted to do? And if you haven’t done it yet, how could you possibly be bored in retirement?

We can’t all be hospital roommates with a billionaire like the Jack Nicholson character in one of my favorite movies, The Bucket List. But if you don’t have the means to do the things on your bucket list, do one of two things. 

  1. Change your retirement bucket list. 
  2. Create a wealth plan that allows you to do the things on your bucket list. 

I talk more about this in my video Wealth Building after 50. 

Summary for Fear of Retirement Boredom 

Now you have 7 ways to annihilate fear of retirement boredom. 

You may have read here that I was fortunate to have had my dad as a role model for an early retirement in his 50’s, which sparked my passion for investing, especially income investing.

He immersed himself more into investing, golf, and volunteering in his retirement years until his early death from a brain tumor at age 68.

There was zero room for boredom in retirement for Dad.  And those last 10 years in living retirement had to have been among the best years of his life.  It’s all a matter of perspective and choice.   

The best place to start is with my Ultimate Wealth Plan. You can get it here now.

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The information on this website is for education only and is not to be construed as personal financial advice.