Rebuilding Resilience And Self-Assurance: Working Online As An Older Entrepreneur

Updated: August 12, 2023
by TJ Salvatore

Your life's wisdom, paired with the strength to face difficulties and the confidence to believe in yourself, can turn these challenges into opportunities. You become more aware of that as you age, don’t you?

If you're in the latter half of your life stage, looking to start a new venture or take your existing business to the next level, there are still lots of possibilities. You can do everything that youngsters don’t easily come up with and make a difference. So build resilience and self-assurance as you navigate this dynamic landscape. You can do this! 

Rebuilding Resilience And Self-Assurance: Working Online As An Older Entrepreneur

Why Online Business Is A Great Option For Older Entrepreneurs

Online business can be a great choice for older entrepreneurs for several reasons, and I'll try to explain it in simpler terms.

Leveraging Lifelong Experience

Older entrepreneurs have years of wisdom and expertise in various fields, which can be turned into an online consulting or mentoring business.

For example, if you've spent 40 years in the construction industry, and now you provide online consulting to young entrepreneurs starting in the same field.

Flexible Lifestyle Compatibility

As an older entrepreneur, you might seek a flexible lifestyle to enjoy retirement or family time. An online business can be managed from anywhere and at any time.

You want to spend more time with your grandchildren, so you create an online course on gardening that you can manage on your own terms.

Less Physical Strain

Starting an online business might be appealing if you prefer work that doesn't require physical exertion.

You've been a physical therapist, and now you create an online platform offering video-guided exercises for people needing gentle home workouts.

Opportunity to Share Knowledge

Many older entrepreneurs have a wealth of knowledge that they want to share. Online platforms allow for this distribution of wisdom.

You were a, say, history teacher and decide to create an online educational website offering history lessons for students worldwide.

Financial Security with Low Risk

Online businesses often require less capital, providing an opportunity for income without a huge financial risk.

If you want to supplement your retirement income, so you start an online book club, charging a subscription fee for curated reading lists and discussions.

Connecting with Similar Age Groups

Older entrepreneurs may wish to connect with others in their age group. An online business can help facilitate this connection.

You create an online community platform focused on travel for seniors, for example. Then you can utilize your own travel experiences and share your tips with more inexperienced travelers.

Pursuing Late-Life Passions

Sometimes, older entrepreneurs want to explore new hobbies or interests. Online businesses allow them to turn these passions into profitable ventures.

For example, you've always loved woodworking, so you decide to sell your handmade wooden crafts through an online store, sharing your passion with others.

Providing Accessibility and Convenience

Physical commuting might be less appealing or feasible for some older entrepreneurs. An online business can be run from the comfort of home.

For example, you have insights into healthy cooking for seniors, so you start a YouTube channel and website offering recipes and cooking tutorials, all from your home kitchen.

The Challenges of Being an Older Entrepreneur

The Challenges of Being an Older Entrepreneur

They say age is just a number, but still, running an online business at a later stage of life is challenging. 

Not Used to New Tech:

A lot of business today uses modern technology. Some older folks might not have grown up with this tech, making it a bit harder for them.

Example: While a young entrepreneur might easily use an app to track sales, an older entrepreneur might find it confusing and time-consuming.

Health and Energy:

As we get older, we might not have as much energy. Starting a business takes a lot of work, which can be tough.

Example: A full day of managing an online store might leave an older entrepreneur feeling more tired than a younger person.

Getting Money Can Be Tough:

Sometimes, people who lend money (like banks) might worry that older entrepreneurs won't have as much time to pay back loans.

Example: A bank might hesitate to give a loan for a new cafe because they're worried it'll take too many years to be successful and pay back.

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Older =/= Outdated:

Sometimes, people might wrongly think that older entrepreneurs are stuck in old ways and not open to new ideas.

Example: Suppliers might offer a younger business owner the latest products first, thinking an older entrepreneur isn't interested.

Starting Fresh Takes Time:

When you're older, you might feel like there's less time to make a business successful, especially if it's a brand-new field for you.

Example: Learning about and starting a business in new technology, like solar energy, might feel like a race against time.

Different Priorities:

Older entrepreneurs might have other things in life they want to focus on, like family or hobbies.

Example: Balancing time between growing a new online business and spending time with grandkids can be challenging.

Changes Come Fast:

Business trends change quickly. If you've been out of the game for a while, catching up can feel like a whirlwind.

Example: An entrepreneur who once sold products in a physical store might find the rapid shifts in online shopping trends hard to keep up with.

Rebuilding resilience and self-assurance as an older entrepreneur


Rebuilding strength in facing difficulties (resilience) and confidence in oneself (self-assurance) is vital for any business person. But for an older entrepreneur, these qualities might be especially significant in the online business world. Here's why:

Learning New Technology

Online businesses often require some understanding of new technologies. As an older entrepreneur, you might find this challenging, especially if you're not used to using the latest tools and platforms. Building resilience helps you face these challenges without giving up, and self-assurance will provide the confidence to believe that you can master these new skills.

Imagine you've spent most of your life using traditional methods of selling products, but now you want to set up an online store. You'll need patience and belief in your ability to learn new technologies. With resilience and self-assurance, you can overcome the initial difficulties and run a successful online business.

Facing Competition

The online world is full of competition. Older entrepreneurs may feel at a disadvantage compared to younger individuals who have grown up in the digital age. Being resilient allows you to withstand competition, learn from failures, and keep moving forward.

For example, if your online crafting store faces stiff competition from younger entrepreneurs with flashy websites, resilience will help you keep improving and adapting, while self-assurance ensures you trust your unique qualities and experience.

Understanding the Fast-Paced Environment

Online business moves quickly. Trends come and go, and customer preferences can change overnight. For an older entrepreneur, adapting to this pace may be challenging. Resilience will help you roll with the changes without getting discouraged, while self-assurance lets you trust your judgments and decisions.

If you start an online blog sharing life wisdom, you might find that the popular topics change rapidly. Your ability to adapt and keep faith in your unique perspective will be crucial.

Building a Connection with Different Generations

Connecting with various age groups, especially younger customers, can be difficult for older entrepreneurs. But having confidence in your ability and being persistent in building those connections can make a significant difference.

Suppose you're selling vintage fashion online. Younger customers might be interested, but you need to understand their preferences and communicate effectively. Your resilience in learning their needs and self-assurance in presenting your products can bridge the generation gap.

Managing the Uncertainty of Entrepreneurship

Starting a new business, especially online, is full of uncertainties. As an older entrepreneur, you might be worried about the risks. But resilience helps you face these uncertainties head-on, while self-assurance ensures that you have the confidence to make wise decisions.

Consider if you're offering online coaching services. The market might fluctuate, client interests may vary, but your ability to stay strong during tough times and trust in your expertise will guide you through.

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Tips for Building Confidence as an Older Entrepreneur

Old age sucks. You feel that way especially when faced with new challenges like starting an online business later in life. But you know that your wealth of experience is your incredibly valuable asset. Here are some tips for building confidence as an older business owner online:

1. Utilize Your Lifetime of Connections

Your decades of experience have likely provided you with a rich network of contacts. Use these connections to help you navigate the online world, get testimonials, or even forge partnerships.

2. Translate Offline Skills Online

You've honed a set of skills over your career. Identify how these can be translated into an online environment. If you've been a sales expert, consider online consulting or creating a sales training course.

3. Consider Collaborating with Younger Partners

Partner with younger entrepreneurs or tech-savvy family members who can complement your strengths with their online know-how.

4. Focus on Niche Markets that Value Experience

You may find success in markets that appreciate the wisdom and experience that come with age. For instance, you could offer consulting or coaching services tailored to professionals in the middle of their careers.

5. Embrace Technologies Designed for Ease

Many online platforms are user-friendly and designed for people who aren't tech experts. Sites like Shopify or Wix can help you establish an online presence without needing to know coding.

6. Provide Products/Services Tailored to Similar Age Groups

Use your understanding of the needs and preferences of your age group to offer products or services specifically tailored to them, like online retirement planning or health and wellness coaching.

7. Set a Comfortable Pace

Recognize that learning new technologies might take longer than it used to, and that's okay. Allow yourself a comfortable pace to adapt and grow.

8. Health-Focused Workspace

Consider ergonomic and eye-friendly setups for your workspace. As vision and comfort might be concerns, invest in quality seating and screen settings to make extended computer use more comfortable.

9. Emphasize Trust and Reliability

Leverage the trust and reliability often associated with age. Highlight your years of experience in your field to foster trust with online customers.

10. Seek Support Groups Specific to Older Entrepreneurs

Join or create online forums specifically for older entrepreneurs. Sharing experiences and tips with peers can foster a supportive community, making the online transition less intimidating.

11. Emphasize Human Interaction

If you value human interaction, consider video consultations or webinars, allowing a more personal connection with your clients or customers online.

12. Mind Your Energy Levels

Balance your online business pursuits with rest. Break your tasks into manageable portions, aligning them with your energy levels throughout the day.

Whatever you do, take care of yourself physically, mentally, and emotionally. No matter what age you are, rebuilding confidence always takes time. You’ll be doing alright.

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About the author 

TJ Salvatore

A freelancer. A nomad. An LGBTQ and animal rights activist. Love meeting new people, exploring new styles of living, new technologies and gadgets, new ways of making money.

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