Top Challenges Facing Older Adults in Entrepreneurship…

Explore the unique obstacles older adults face when venturing into entrepreneurship. Learn how to overcome these challenges and thrive in business.

It’s a challenge…

Let’s start off by saying that it is a challenge and can be hard for some older adults. Not only is it a time when most working older adults have grown up with technology and kept up with it to a degree. There is a growing trend of these adults also creating content as well! Look at some artists that have posted live feeds and such during Covid and continued with that trend.

The biggest part of this is that the entrepreneurial spirit is still alive and many have gotten into it as well. Some can say that is due to the state of the economy, but mostly it comes from a need to do something other than sitting on the couch or porch. We all want to have that desire to be creative and have someone like what we created. Just lately it seems to be on a more upfront and center type of approach.

So what are these challenges???

What are some of the top challenges you ask? I ask this question about every few months. Mostly because I am now in this demographic. From what I have read on LinkedIn, Reddit, and other social media channels.

  • Ageism- the biggest one that seems to be prevalent in topics these days.
  • Adapting to newer technology- Unless you grew up on tech, this would be the most difficult to master.
  • Work/Life/Health Balance- This is probably the most important yet often overlooked as you age and become an entrepreneur.
  • Fear of Failure- This challenge knows no age, race, or creed. This affects all entrepreneurs equally.


Yes, it’s that dreaded word for many of us. Many companies are dumping plenty of those with the skills and experience for their bottom line. While those entering and have been in for a short time are now trying to figure out how things work. Society now thinks if you are over 50 you are too old or slow for work. Yet, that chunk of experience will be lost, because many will not give back after such a sendoff.

Adapting to technology…

This is somewhat of an oxymoron of sorts. If you are older than 60 then I can see it. Since many did not grow up with such new tech. While we Gen Xers have, many either didn’t keep up or ended up creating some of the brands we know today. The biggest challenge with new tech is how well we figure it all out. Did we learn how to comprehend the concept and idea of such tech and how to easily learn how to use it? Always a question when something new comes in, yet once you do anything new and have experienced it, you now have experience in it.

Work/Life/Health Balance…

This one, each could be in its talkpoint, but as we get older these all come together in the end. A lot has to deal with the point of health issues, trying to work over 80 hours a week, and also dealing with life itself. The mental aspect can be a big challenge due to how you feel about your vision. What will your family think, about you going off doing something younger does? Do you have any health issues that now need your attention when before that was not the case? Plenty of questions here that seem not to get answered. Yet, for those still working and doing some sort of entrepreneurship on the side, taking care of your health becomes the biggest thing nibbling on your mind. You want to be able to make it but also have to ensure that all of your work is protected. Family will have their thoughts, while society will have theirs. It is up to you how much you want to push yourself, how healthy you are, and if work (if you’re working full-time or part-time) can handle it all. This may warrant another separate post, if you want a primer here is a link to a past post about balance, titled Finding Balance.

Fear of Failure…

This one has no challenges to show up for any entrepreneur. From the fear of losing all of your work, to not making anything work to just failing overall. The fear of failure is always on everyone’s mind when starting for themselves. Just because you are an older adult, that fear of failure is high, the retirement age is close and you do not want to lose out on money when you stop working. Not only having retirement money, financial ruin is always something any entrepreneur thinks about. Usually, as a younger entrepreneur, this is not the case, but once you reach a certain age, you look at it more as a way to add to it.

entrepreneur for an old adult

Other challenges…

Other challenges could be on the list. A lot of these other challenges are mostly centered around your particular situation. From having support but not the right kind, to having no support of any kind. Maybe it’s literally a housing or financial reason right now. For me, in my case, I live on a couch and still attempting to find something that works as an older entrepreneur. This is probably one of the biggest challenges I face, while others may have that corner spot in the spare bedroom to work.

The many other challenges can vary, I have seen issues with marketing analysis, to straight-up marketing in general. Or even interpreting social media trends or influencers’ lingo, etc. This list goes on and on. With all the different challenges out there, the biggest one is just not starting. Write out a list of pros and cons of a project to see if it will work. Don’t worry about the financials, worry about the vision and overall scope of the project to see if it’s workable.

Final Thoughts…

So you think this is hard, try just living these days! Seriously, this is only my opinion and thoughts about the experience. If you want a younger thinking post about entrepreneurship read this post about Entrepreneurship vs. Employment. I am a new older adult entrepreneur and I feel that it is more about not wanting to work for someone or some company that lately seems to not give a damn about you or your tenure there. For me, it’s all about trying to make enough to do other things. I look at being an entrepreneur as a way to fund my lifestyle of living life rather than just working to retire and enjoy things I enjoy doing now. Where I flip the script in doing things you normally see retired adults do, I already do. Feel free and confident that you are not alone in your thinking and that others are willing to help you out if you just ask.


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