Why Retirees Hold Back On Entrepreneurial Thinking (And How To Change It)

Entrepreneurial thinking! Why should you complicate life when finally reaching retirement?

The classical idea of retirement as a slow down and relaxing time is chasing, and it’s going fast. In this article, we will knock down all barriers and undergo a re-engineering process.

If you read to the last line, we will turn your “holding back” attitude into one where your entrepreneurial thinking flourishes more than ever.

Before starting our reinterring process, have a look at these figures:

In the U.S., 79% of small businesses are owned by people over 50, either by baby boomers (30%) or Generation X (40%). Probably the figures are similar in other similar countries.

In Mexico, where I’m living, 6 of 10 companies are classified as informal entities. No matter the size or niche, the leaders of these informal companies wouldn’t have achieved what they have without entrepreneurial thinking.

Holding Back on Entrepreneurial Thinking

Holding back entrepreneurial thinking — Image by Anna Shvets on Pexels

There are five principal obstacles to taking the leap and becoming an entrepreneur when passing the retirement line.

In many cases, it’s a result of the long-awaited day to finally be released from a job you didn’t like very much, and perhaps even hated. The job was necessary to earn a living.

In other cases, I belong to this group, we loved the job we were dedicated to, but it didn’t leave enough time for the family life we wanted. Or there was a favorite hobby we couldn’t devote as much time to as we’d like.

There can be many other reasons as well, but the point here is that suddenly you get 40, 50, or 60 hours per week, and you can use it however you prefer. In this context, you easily focus on all the activities you missed out on during your corporate life, rather than going deeper into your thoughts and bringing out the entrepreneurial mindset we all have somewhere in our heads.

Time for endless vacations

First out is the “vacation mode.” After a long period of time working hard to earn your money, you deserve a “cool-off” period. Waking up to the kiss of your spouse or the sunshine sneaking in through the window. No alarm clocks, no breakfast stress. Just relaxing and stress off.

Perhaps you do funny things with your partner, your children, and your grandkids. You meet other retired friends and do things together. Life is just marvelous.

Then, after a while, without even noticing, this relaxing lifestyle becomes a routine. And your daily routine becomes a habit. What else could you add to make your retirement life complete?

Before this happens to you, let your entrepreneurial thinking get the space it deserves. Imagine how developing your skills, experience, and knowledge can lead to new personal growth and fulfillment.

No experience

We all know that most things are happening online today. Just go to yourself and count the hours you scroll on Facebook daily. Ads of all types bombard you, and algorithms find you faster than you can imagine.

With entrepreneurial thinking, you could start imagining that the person behind those ads was you.

But no! The monkey behind your ear is there faster than your mind can even reflect on the possibility.

“You have no experience, so forget it!”

When I started my online business over a decade ago at the age of 62, I didn’t know anything beyond opening Facebook and sending emails. But a voice inside me said I was being stupid if I didn’t turn my experience, skills, and knowledge into an online business.

Long story short. I started my blog, and all of a sudden, I became a passionate blogger. As you are still reading, apparently, I had some experience to share with the world.

The bottom line is:

Do not dig into what you don’t know, but focus on your experience and develop it.

No skills

“But I have absolutely no skills in this online business thing.”

When you were hired for your very first position in your career, what skills did you have? Nothing more than a diploma from the university means that you are now a professional engineer, economist, or whatever it was in your case.

But you were hired for a reason, and the company invested in you. They gave you all the necessary training to become productive as soon as possible.

In today’s online world, you can access affordable, beginner-friendly training in any field with just a click, making skill development accessible and straightforward.

With my “no skill” background, I quickly learned everything I needed to know. Honestly, I was really proud of myself after creating my first website in a couple of weeks.

The takeaway:

Obtain the skills you are missing by clicking on the correct link, and let your existing skills flourish.

No investment capital

If your monkey behind your ear is still alive, it will whisper:

“You have no money to invest. It costs too much!”

Before the digital era, when franchising was the trend for enthusiastic entrepreneurs, how much did a franchise cost? We are talking about a 6 to 8-figure investment. If you weren’t willing to spend all your savings or break the bank, the franchise opportunities were limited to a very small number of wealthy people.

In today’s online world, opportunities are open to anyone. With a couple of hundred dollars, you are in. By seriously working on your business, that tiny investment will be recouped in a few months through the revenues your new business generates.

Conclusion:

Money is not an obstacle to starting an online business; your entrepreneurial thinking is.

Too risky

Life is surrounded by risks, anytime and anywhere. When stepping out of bed in the morning, you could make a wrong step, fall down, and break your leg. So if you’re afraid of risks, stay in bed (LOL).

When you invest your money in the stock market, there is a risk that you will lose money.

Understand that online business risks are manageable; with proper planning, you can minimize failures and feel more secure in your entrepreneurial journey.

Add to this that in today’s competitive online business environment, every serious company offers a money-back guarantee within a certain period, if you, for any reason, aren’t satisfied with what you invested in.

Thus, an online business tryout is today a low-risk project, with the probability of losing close to zero.

Thought on this one:

The risk of losing in an online business adventure is low or close to zero, and is often used as an excuse not to let your entrepreneurial thinking evolve.

Mastering Retirement by Entrepreneurial Thinking

After re-engineering all obstacles holding you back from becoming a full-time or part-time entrepreneur, one piece is still missing.

How to make it happen?

As my time in the corporate world neared its end, I didn’t just wait for the day to come. Instead, I started well in advance to figure out how to maximize my retirement lifestyle. Watch the video where I explore my journey, which can also inspire you to follow a similar path.

Let this free training unleash your entrepreneurial thinking!

Imagine the kick of learning new digital strategies, even if you start from a blank sheet—the joy and satisfaction of helping and connecting with people who appreciate your work.

“The way to get started is to quit talking and begin doing.”

Walt Disney

Key Takeaways

Usually, retirement is seen as the end of a career, a time to slow down and relax. However, retirees are abandoning that old playbook and embracing new challenges by applying entrepreneurial thinking.

Do not dig into what you don’t know, but focus on your experience and develop it.

Obtain the skills you are missing by clicking on the correct link, and let your existing skills flourish.

Money is not an obstacle to starting an online business; your entrepreneurial thinking is.

The risk of losing in an online business adventure is low or close to zero, and is often used as an excuse not to let your entrepreneurial thinking evolve.

As we are approaching the end of the year, give this article a thought. Why not include “entrepreneurial thinking” in your New Year’s Resolution for 2026?

Happy Holidays!🪅

—