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There are plenty of stories about women age 50+ becoming entrepreneurs. Some of them work online so they can take their work with them while they travel.

Should you take the plunge and join the growing Self-employment and Digital Nomad trend?

When I presented the idea for a Talk on this topic to Royal Roads University, I told them I was thinking of it as a Public Service Announcement.

While I believe everyone can have a stream of income from self-employment, I’m not convinced that an Online Business is a good fit for all of us. ( Something like a Dog Walking service is much easier to launch. )

It is a good idea to make your decisions about self-employment with your eyes wide open - not with visions of sugar plums dancing in your head.

There are lots of folks teaching how to launch an online business for Digital Entrepreneurs. They tend to promise you a 6-Figure Business and they want to sell you their Blueprint.

Reality Check: Only 3% of female entrepreneurs in Canada will make $100,000 or more a year. Many people know how to live well and travel Abroad on less than $40,000 a year.

I thought an Online Biz would be a good fit for me because I like to Travel and I’d like my work to be Portable. I want to share my experience with you so you can be better-prepared than I was if you decide to go this route.

It’s not that the Online Business Experts don’t have good information to share with you. It’s that they tend to over-share - so much so that if you sign up with one of them you are likely to feel swamped - much like in the Disney Movie, Fantasia.

Do you remember when Mickey was the Sorcerers’ Apprentice - and he used his Magic Wand to get a broom to help him carry buckets of water?

The trouble came when the broom kept carrying water and Mickey wasn’t able to stop it. Before long, Mickey was drowning in all the water his “Helpful Broom” was delivering.

So, that’s my experience with Online Business Experts.

Once I’d bought their Business Program - I was overwhelmed with their “helpful information” - that arrived in never-ending buckets via email.

No-one wants to be overwhelmed. In fact, we usually seek out Experts so we can simplify things.

In the Beginning …

I had a Simple Plan.

Four years ago I wrote a book called, Work On Your Own Terms in midlife & beyond. I wrote my book to help Boomer women enjoy their Life and Work past “retirement.”

After 20+ years as a Career Counsellor, I wanted to share what I thought would help women live a more flexible lifestyle with enjoyable work to support it.

My Simple Plan was as Easy as 1, 2, 3.

  1. Write my Book.
  2. Give Free Talks in Public Libraries.
  3. Host Retreats based on my Book so women could put my suggestions into Action.

That was it. That was my whole plan.

Then, I met a lot of Business Gurus who convinced me I needed help with Marketing so I could get the word out about my Book and Retreats.

And … that is when I
Rabbit Hole.

And it was a long, long, tunnel with lots of twists and turns.

This is what they told me I needed to do:

Choose a Domain name.

Set up a Website.

Decide on a WordPress Theme for the Website design.

Choose an email account for the Website - like MailChimp so you can keep in touch with people who want to hear from you.

Write Blog Posts.

Post them on your Website.

Get an Amazon account. Upload your Book to Amazon.

Get a FB account that matches your Website.

Get a LinkedIn account. Write articles for LinkedIn.

Get a YouTube account. Create some Videos for YouTube.

Get on Pinterest. Post a lot of pictures on it.

You want to Tweet, don’t you? Sign up for Twitter.

Create an etsy Store.

Get on Instagram.

Snapchat is popular. Grab that too.

Get both Skype and Zoom accounts.

Create a Funnel.

Find some Joint Venture partners.

Join an Online Forum and contribute to the discussion.

Learn about Google Analytics.

Buy a Plug-in.

Buy another Plug-in.

Why not buy a third Plug-in - just in case you need it?

This is an Incomplete List.

I just wanted to give you a taste of the joys of an Online Biz.

I don’t want to overwhelm you with everything I’ve learned.

Solopreneurship can feel like you are trying to run a corporation single-handed. It’s a lot of work to run a Business from scratch and can’t be done on your own without exhausting yourself.

I’m sure you can do it. But, are you sure you want to? You will need to hire others who have the skills you lack. Be prepared to devote more time and money than you initially believe you’ll need.

Technology can be a steep learning curve. Just when you think you’ve learned everything you never wanted to know about technology - something new will come along to replace what you thought you’d already mastered. As someone who grew up seeing an Etch-a-Sketch as “high tech” - I find it difficult to keep up with the latest gizmos.

So, I bought the expertise of several Online Business experts.

I got sucked in each time someone told me they had an Easy Peasy Plan to help my new business grow.

It turns out - they all have a similar 597-Step Plan!

They just gave it a New Name each time.

And not one of them is a 3-Step process.

The crazy thing is - the Online Business Experts KNOW most people won’t be able to follow their 597-Steps. Once you’ve bought a program, it’s sink or swim for you. They’ll throw you a life line now and then - but if you drown - it’s too bad, so sad.

Do Not Fall Down the Rabbit Hole.

However, if you love technology and are attached at the hip to your iPhone - being a Digital Nomad may be ideal for you. It can also be for you if you have a devoted family member who enjoys sitting behind a computer all day.

Technology will Test you.

Be prepared! You will need to learn some of it even if you are able to delegate tasks to someone else.

Here’s some Good News - Learning all this stuff helps rewire your brain which is said to contribute to healthy aging! ( So, it’s not All Bad! )


But, if you’re in your 60s -
this may not be how you want to spend your time!


So, let’s do a little QUIZ to see if you are cut out for Entrepreneurship.

Daniel Isenberg is a Professor of Entrepreneurship.

He created a Quiz he calls the 2-minute Isenberg Entrepreneur Test

Source: Harvard Business Review
Should you be an entrepreneur? Take this test.
by: Daniel Isenberg
Feb. 12, 2010

Answer YES or NO to each question.

Be honest with yourself. No point trying to fool yourself.

1] I don’t like being told what to do by people who are
less capable than I am. YES / NO

2] I like challenging myself. YES / NO

3] I like to win. YES / NO

4] I like being my own boss. YES / NO

5] I always look for new and better ways to do things. YES / NO

6] I like to question conventional wisdom. YES / NO

7] I like to get people together in order to get things done. YES / NO

8] People get excited by my ideas. YES /NO

9] I am rarely satisfied or complacent. YES / NO

10] I can’t sit still. YES / NO

11] I can usually work my way out of a difficult situation. YES / NO

12] I would rather fail at my own thing than
succeed at someone else’s. YES / NO

13] Whenever there’s a problem, I am ready to
jump right in. YES / NO

14] I think Old Dogs can learn - even invent - New Tricks. YES / NO

15] Members of my family run their own business. YES / NO

16] I have friends who run their own businesses. YES / NO

17] I worked after school and during vacations
when I was growing up. YES / NO

18] I get an adrenaline rush from selling things. YES / NO

19] I am exhilarated by achieving results. YES / NO

20] I could have written a better test than Isenberg
( and this is what I would change … ) YES / NO


If you answered YES to 17 or more of these questions, Entrepreneurship may be a good fit for you.

[ I got 15 YES answers. so, my suitability is a bit iffy. ]

IF YOU ANSWERED “NO” to most of these Statements,
Self-Employment may not be your best bet.


Isenberg wants you to notice what’s NOT on his list.

“I like to take risks” is Not on the list.

People don’t choose Entrepreneurship because they want a riskier Lifestyle. ( However, they are willing to step out of their Comfort Zone. )

What they do is weigh the Risks of being an Employee vs. being an Entrepreneur.

Risks of being an Employee


Bad Boss - As Career Counsellor - main reason people told me they left Jobs.

Lack of Autonomy

Lack of Control over your Fate

Worried about being Laid Off

Risks of being an Entrepreneur

Possible Failure

Financial Uncertainty

Shame or Embarrassment

Lost Investment


My own MA Thesis on The Future of Work verified this.

My Research uncovered very similar results.


People who are meant to be Entrepreneurs believe in themselves

They exhibit:

Leadership from Within


Pluck / Chutzpah / Guts

Hard Work - willing to work 24/7 as needed.

Have Assets - Money / Intellectual Property / Information

They Pay attention to their Intuition


Something else NOT on Isenberg’s List:

“I want to get Rich.”

On average, people who choose Self-employment don’t make more
money. [ Although, there is no Glass Ceiling in your own Biz. ]

The worst reason to start a business in your 60s is Just to Make Money.

You might be able to make a high income quickly if you have the Bulldog Personality of a Donald Trump - but don’t count on it.

The funny thing is that what he seems to be teaching us is - there are NO RULES we need to follow.

You can write your own rules and Live Life On Your Own Terms.

I encourage you to do that.

We’re moving into a time when the Sharing Economy is growing and Collaboration is connecting more and more of us around the world.


If your #1 Goal is Not Money - What’s the Reward?

It’s the Psychic Benefits



Recognition - esp. if a Former Boss took all the Credit.



These make Self-employment worth the risk.


From My Perspective, the #1 Reason to pursue Self-employment is …

You feel compelled to Share An Idea you Truly Believe can Help People Improve Their Lives.

You Feel it is your Mission to Share This!

It’s something you Can’t NOT Do.

You have to do it!

You have a Burning Passion or Desire.

You want to Change Something to Make It Better.


Self-Employment is also a good path to follow if you are someone who Loves To Learn.

It’s the Best Personal Development Program you’ll find.

It will test your Limits, Grow You and Reveal Your Capabilities to Yourself.


Here’s the Truth about how to launch after age 50.

A lot of us just aren’t cut out for an Online Business - esp. with all the Technology involved.

I discovered this after Jumping in with both feet and hands!

We don’t want to be Chief, Cook, and Bottle Washer.

Hence, the trend towards Collaboration.

If you want an Online Business, plan to hire people to do the skills they do best so you can spend most of your time on what you do best. There is a growing co-operative movement of women in business supporting other women in business.

The GIG ECONOMY is encouraging collaboration on Short-Term Projects and is predicted to grow to 45% of our economy by 2020.

Intuit Canada says 45% of Canadians will be self-employed in the Gig Economy by 2020!

That’s less than 3 years away!

The Good News about the Gig Economy is - having more than one source of income from a variety of Projects can provide more financial security because you won’t have “all your eggs in one basket.”

If you think Entrepreneurship is for you - I’m sure you’ll agree there are lots of PROBLEMS in the world looking for SOLUTIONS.

Find Your Voice and use it to Create a Better World.

This is my 3-Step Advice for New Entrepreneurs

  1. I encourage you to Find a PROBLEM you can SOLVE - and hopefully create an Income from it down the road. Understand, this will take time.
  2. Once you have a SOLUTION to a PROBLEM - find the Most Enjoyable way for you to Deliver it. I prefer working with People Face-to-Face.
  3. Start with only ONE WAY to promote it. I began with Free Talks.


While struggling with Technology, I started to research how I could Save Money and Make an Income while I Travelled.

I have a Passion for SLOW Travel and I knew I hadn’t saved enough to fund a 30-year Vacation called Retirement.

I discovered numerous ways to Save Money and Make an Income while Travelling.

Once I began talking to friends about this, they were interested in doing the same.

So, I’ve narrowed my Focus and gone back to something closer to my Original Plan.

I help Women my age who want more time to TRAVEL but don’t want to Spend all of their Savings to do it.


If you want to Travel and need Money to do it …

There’s an Easier Way than being a Digital Entrepreneur.

There are Many Ways to SAVE MONEY and MAKE AN INCOME while you Travel - Both With and Without an Internet Connection.

A BONUS of TRAVEL is it can help create a BETTER WORLD through understanding OTHER CULTURES and MAKING FRIENDS AROUND THE WORLD.

Who doesn’t think we need to create a Better World?

Travel can create a deeper understanding of Other Cultures which can help create more Peace in the world.

Travel can also help us Find out Who We Are.

We can Find Our Voice while away from home in a new environment.

3 Common Reasons Why People Travel
These overlap with the reasons many choose Self-employment.

  1. Fulfill a Lifelong Dream.
  2. Realize their Potential.
  3. Find their Purpose.


A good Example is Julia Child.

Her time in France helped her Find Her Voice through Cooking.


I want to ask you a Very Important Question.

It’s a Simple Question.

Unfortunately, it may be hard to answer.

The Question is:

What Do You Want?

What Do You Want to Experience in Life? I asked myself this.


The answer is inside you.

Tap into your Heart and Intuition to find your answer.

I think it’s important to Decide the Lifestyle You Want to Live and then Decide How to Support It.



I’m sure you’ve heard of De-Clutter Queen, Marie Kondo and her Life-Changing Magic of Tidying Up.

Her Book is a BestSeller.

Marie Kondo went a bit overboard for me with her Sushi-Roll Sock Drawer - but Focusing on What Brings JOY into your Life is Good Advice.

Marie elevated SIMPLICITY & DE-CLUTTERING to a new High.

Many are now choosing Simplicity as a way to get to the Core of What They Really Want.

If you are ready for Midlife Reinvention…

Choose Simplicity.

Design your own Simple Plan and Stick With It.

Maintain your Focus.

So, I’ll ask again: What Do You Want?


Do you want to create an Online Business?


Would you prefer to FIND YOUR VOICE and Use Your CREATIVITY While you Travel?


“This time, like all times,
is a very good one,
if we but know what to do with it.”

Ralph Waldo Emerson


Janine L. Moore is a Midlife Reinvention Coach. After 20+ years as a Career Counsellor, she now helps women to reinvent their life and work while they travel. She can help you find your Purpose and why it matters.

You can Download a Free Copy of 10 Delightful Ways Travel Can Change Your Life at: