What Is It Like To Own A Business In Your Older Years?

What’s the prime age to open a business? If you ask most young entrepreneurs, they’ll tell you that the earlier the better. They’ll say that younger people are more open to adapting to the quick pace of change in the modern world. That older people are more likely to be technophobes who have an outdated understanding of how business works.

But if you are thinking about starting or buying a business in your later years, you may disagree. Whether you’ve just hit fifty or are well into your seventies, you know you have a lot to give. Your age is not a disadvantage but rather gives you experience and wisdom.

Which narrative is true? Are older entrepreneurs overly optimistic about what they can achieve in the modern world?

What do the stats say?

We can debate the question in hypothetical terms indefinitely. However, assumptions mean nothing in the face of facts. As such, looking at what the stats say is far more useful.

A 2021 study looked into the makeup of US small businesses, paying particular attention to ‘encore entrepreneurs’. Encore entrepreneurs are defined as entrepreneurs over the age of 55.

The report provided fascinating insights on who is really running the show in the small business arena. While this demographic makes up just 21% of the population, they own just over half of all small businesses. This is in sharp contrast to the idea of young bucks leading the way by building exciting tech startups.

Keep in mind that this study was carried out shortly after the worst of the COVID-19 lockdowns. At the beginning of those lockdowns, encore entrepreneurs were expected to fare the worst out of everyone. The idea that they owned ‘mom and pop’ brick-and-mortar stores – and as such wouldn’t handle the transition to online business – was compelling. As it turns out, that has been far from the case.

Business longevity

There is another pertinent study regarding older entrepreneurs. This is a pre-COVID study (from the halcyon days of 2019), but its findings are certainly still relevant. This study was carried out by JPMorgan Chase Institute. It found that businesses run by older people are less likely to go under.

A business run by a 60 year old has a 8.2% probability of going under, compared to a 9.6% risk for 45 year olds and an 11.1% risk for businesses started by thirty year olds.

The argument that the experience and wisdom of older people is an advantage clearly has a leg to stand on.

But let’s look into the actual experience. What is it like to own a business when you are in your later years? Where do you find the motivation and is there a reason to avoid getting into business later on in life?

What motivates older business owners?

There is another assumption many people make when it comes to age in the business world. This is that younger people are more motivated to start businesses and have more ambition. They have decades ahead of them and the energy of youth.

While there is truth to this, it leaves out a lot of important context. Someone starting a business at the age of thirty is stepping out into the unknown. Their experience is primarily learnt. They have a lot to lose – both in terms of money and their own self-esteem.

Older people do not have as much to lose, even if they don’t have all the money in the world to spend. Their success or failure does not determine the course of their lives. Their identities are more fixed, and they don’t feel the same need for validation that hovers over young people.

This lack of jeopardy leaves them open to trying things that might not work simply because that’s what they want to do. Instead of playing it safe and going into a business that is likely to succeed financially but does not excite them, they can pursue their true passions. Their business then does not rely on their drive to make more and more money, but rather persists due to their enjoyment and the meaning they find.

Of course, there are other considerations that provide challenges to older (or encore) entrepreneurs. Debt in particular takes on a very different complexion.

Business debt for young vs old entrepreneurs

One of the common fears for people approaching the end of their careers is the prospect of retiring with debt. The concern is that they will have to continue paying off mortgages, auto loans, and the like, while no longer earning an income. The debt may eat into their savings and affect their quality of life in what are supposed to be their golden years.

For this reason, it is reasonable to assume that taking on new business debt in retirement could have a negative effect on wellbeing. After all, you are introducing risk into a time of life which is supposed to be risk free. Is it worth it?

There is no one-size-fits-all answer to this question. For some encore entrepreneurs, the belief in their own success is enough. They do not worry about debt because they know that they will reap the financial rewards. For others, taking on debt sounds like a terrible idea.

There are many in between, as well. This is especially true for entrepreneurs who have spouses relying on the same retirement income sources. While one partner may feel comfortable with new debt, it may make the other extremely uncomfortable.

How does this compare to taking on business debt in your younger years? The concerns are of a very different nature. A younger person is likely to have more opportunities to turn their fortune around if one business fails. On the other hand, they are also likely to have people relying on their income, which increases the associated anxiety.

Another big difference is that for many younger people, this is a necessary course whether they like it or not. They need to earn an income one way or another and relying on their business savvy while avoiding a business loan default is better than chasing promotions in someone else’s company. In contrast, someone who already has the income they need for retirement does not have to face the same anxieties.

Are there other concerns for encore entrepreneurs?

There are certainly other concerns for encore entrepreneurs that don’t impact younger people. When you are at retirement age, the people around you are settling into their retirement years too. A young entrepreneur moves in a society made up of other entrepreneurs. An older entrepreneur is generally plotting a different course from their peer group.

It is also important to acknowledge the prejudice society has regarding older people. Many younger people do not take older people as seriously as they would someone still in their ‘prime’ working years. They may disregard what an older business partner says or choose not to work with a business run by an older person for fear that they will be inflexible and overly-traditional.

We’ve also mainly spoken about encore entrepreneurs who are otherwise comfortable. There are unfortunately many people who cannot afford to risk going into business during their retirement years as they are just eeking by as is. There are also people who stay in business or choose to go into business in their older age because they need the money and see no other choice. For these encore entrepreneurs, the sense of jeopardy is real and can have a significant impact on wellbeing.

All that being said, encore entrepreneurs have a lot of advantages. Experience is not something you can learn. One of the main reasons businesses run by older people are less likely to go under is because they know how to interpret signs and situations that younger people are blind to.

Older people are also less impulsive, making decisions based on a wealth of data rather than going on instinct. Our society has the habit of extolling instinct, especially in youth, even though instinct very often leads entrepreneurs to make terrible decisions.

How has the shift to online business affected encore entrepreneurs?

We’ve mentioned that older entrepreneurs managed to weather the pandemic much more effectively than many expected. They were able to move online when it was necessary. But how has that shift affected encore entrepreneurs? Is it something they have merely weathered or embraced?

A major reason that people saw the pandemic as the end for an older generation of business owners is that we have an outdated perspective of the types of businesses older people run. Our minds immediately go either to mom-and-pop stores or to big, traditionally-run corporations.

Many mom-and-pop stores closed down and corporations struggled during the pandemic. But these were far from the only type of businesses older entrepreneurs owned. Furthermore, the shift to a more online life that affected people of all ages has led many encore entrepreneurs to consider ideas they previously wouldn’t have thought possible.

Some retirees working on their own artistic pursuits were simply looking for connection and started getting their art out there on online platforms. This led them to create new online stores and artistic endeavors.

Others spent more time online and saw the ways in which others were making money and positive business moves. They realized the potential to pursue the opportunities that seemed too idealistic or risky in their youth.

There are also plenty of encore entrepreneurs, who would have started businesses regardless, who used the shift to online commerce in order to create something more substantial. They have flourished by using their business nous while taking on the benefits of modern enterprise.

To a large extent, the shift online benefited encore entrepreneurs. However, this wasn’t the case across the board.

The struggles of owners of old businesses

The shift to a more online marketplace was necessary due to the pandemic, but it did leave some businesses in the dust. This was especially true for particularly old businesses that had resisted the pull of modernity for years or even decades. Encore entrepreneurs who were not able to adapt simply had no option but to go out of business.

It is easy to blame them for their own rigidity, but the reality is that the ability to adapt is far more natural to some than to others. There are plenty of people who would love to adapt to a modern way of doing business but just cannot get their heads around the new technology.

This difficulty was compounded by the impact the pandemic had on the health of older individuals. COVID-19 has been far more dangerous to the older population. People who have lost loved ones around the same age as them have struggled to go on as normal. Running a business can start to feel overwhelming and retirement may just seem like the more natural option.

The lingering physical effects for people who suffered from COVID-19 and recovered have also pushed people towards retirement. Their businesses may be thriving, but when your body is struggling, going to work each day is a whole lot harder.


Ultimately, the perception that older entrepreneurs are rigid and less likely to succeed in a modern world is patently untrue. The stats show that older entrepreneurs are more likely to succeed than younger ones. There are a number of reasons for this, including their wealth of experience and the lack of a need for validation.

Nonetheless, some older entrepreneurs have struggled as we’ve shifted to an online world, and the health effects of the pandemic have played a part in that.

If you’re considering starting a business in your later years, it is worthwhile to know that you have a good chance of success. There is always risk, but your experience and wisdom will get you far.


Dee is a well-respected business journalist with a deep understanding of global financial markets and a talent for uncovering the stories behind the numbers. With over 20 years of experience covering the business beat, Dee is known for his in-depth reporting and analysis of industry trends, as well as his ability to make complex financial concepts understandable to a wide audience.