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The Most Inspiring “Problem” with Starting a Business in Midlife

Young entrepreneurs might get all the press, but midlife entrepreneurs — sometimes known as “encore entrepreneurs” — are a category that’s showing explosive growth.

Starting a business in midlife is in vogue. And there are lots of great reasons for it which we’ll explore here.

According to a study by Paychex, there has been a massive surge in people seeking midlife career change since 2007. Here’s what they found:

“In 2007, there were two 50-plus year old entrepreneurs in every 10. Today, the rate stands at three in every 10.”

That’s a 50% increase in entrepreneurship for this age group!

If you’re looking for a career change at 40-50-60 and beyond, keep reading. You are fortunate to bring some important assets to the table.

There are a few challenges you may encounter, too — but awareness (and the tips here) will help you navigate them successfully.

Bonus: How to explain your online business to family and friends

This short video will help you explain your online business to people who have no idea what it is you do.

At 01:14 I’ll give you a great tip about what to do before the conversation even starts.

And I’ll give you 3 examples to help you talk about your online business!

Subscribe to my YouTube channel for weekly online business guidance.

Why starting a business in midlife gives you massive advantages

If a job change in midlife is in the cards for you — especially if you plan to create a new business — you can count on having a lot of advantages.

Here’s what you can tap into:

  • Deep expertise that’s anchored in real-life experience
  • Empirical knowledge based on lived experience
  • Full appreciation of the challenges and opportunities your topic presents 

There are a few intangibles I’ll bet you have, too:

  • Patience, built on years of experiencing the ups and downs life brings
  • Contacts: You likely have a solid professional network you’ve built over the years
  • Capacity for learning: You’ve had to learn new techniques and technologies to stay current

Here’s the beautiful thing about hitting midlife:

You know yourself and your strengths — and you know what motivates you.

Couple that with the fact that you don’t put up with “a lot of nonsense” (as my mom says) either from others or from yourself. You get to the heart of things and ignore the rest.

This makes you a powerhouse business owner waiting to be born, my friend!

Photo of Pamela Wilson showing advantages to starting a business in midlife: You are able to anticipate what's coming ahead and react to it accordingly.

The challenges of starting a business in midlife

By this age, you know that life is not a box of chocolates, a bed of roses, or a field of daisies.

You know this because you manage some of life’s harshest realities, including:

  • You may have more financial responsibilities than before
  • You have less time ahead of you to make your business successful
  • You may have more fears (that are based in reality!)

But there’s one more insidious challenge that might keep you from starting a business in midlife …

The REAL challenge to online business builders in midlife

I believe that the biggest midlife challenge is the difficult choice we must make between all the possible business ideas we could develop.

We’ve achieved mastery in a lot of things, so there’s lots we could do.

When we were younger, we lacked experience, authority, and gravitas. Now, we have all of these things in spades — and sometimes in more than one field of expertise!

As Barry Schwarz talks about in The Paradox of Choice, it’s more difficult to make decisions when we have an overabundance of options.

Here’s the most important sentence in this article …

Midlife business building is about should rather than could.

There are a lot of topics we could build a business around.

The question is …

What should we build our business around? Who should we aim to serve? Which option should we pursue?

In this article’s headline, I call this an inspiring problem because of how it can make you grow as a person and a future business owner.

Here’s an example:

James Irvine signed up for my BIG League program just a few short weeks ago.

James was starting from scratch — he was in the PLAN stage (learn more about my Plan & Grow BIG stages and get your free Online Business Success Roadmap here).

Within three weeks, James got through the PLAN stage by using the BIG League training and resources.

Here’s what James said just today:

A close up of text on a black background

How to choose your best business idea from the dozens you’re juggling now

Settle in with a cup of your favorite beverage and a place to write. Ask yourself these three questions:

  1. How do I want to spend my time? Think through what your day-to-day life will look like with the business ideas you’re considering. Does it sound like fun?
  2. What will I not get bored of? You know yourself well enough to know that there are certain activities you could do aaaallll day long, and others you’d rather avoid. Will this new business idea hold your interest for years?
  3. What topic do I want to go deeper with? Do you have a never-ending curiosity about a topic you’d love to explore more deeply? A business built around that topic will give you the opportunity to expand your knowledge and build your expertise.

Finally, ask yourself this game-changing question:

Is there a demand for this offer? This is not a question you can answer without a little digging.

Once you’ve narrowed down your ideas to one potential winner, I highly recommend Pat Flynn’s book, Will It Fly?: How to Test Your Next Business Idea So You Don’t Waste Your Time and Money. Pat walks you through a step-by-step approach to answering this crucial question.

Take the time to work through his process so you can feel confident about starting a business in midlife.

Get guidance, support, and proven systems

I would be honored to support you as you build a business during this stage of your life — and you’d be in excellent company.

BIG League members are professionals just like you who have deep expertise, curiosity, and a willingness to learn new things. And many of them are starting a business in midlife — if that’s what you want to do, you’ll be in great company.

Learn more about the BIG League when you grab your free copy of the Online Business Success Roadmap.

Editor’s note: This article was originally published on April 3, 2019 and has been updated with two videos with helpful information for online business owners. Enjoy!

Pamela Wilson

Pamela Wilson is the Chief Marketing Officer at DCS. She’s the creator of the Offer Accelerator Program. Learn more about Pamela’s content marketing books, and read reviews of the tools used to run this site.
Pamela Wilson coaches people in midlife to build profitable online businesses
I’m Pamela Wilson

In 2010, at the age of 45, I started this site and grew it into a business that offers freedom, flexibility — and consistent revenue.


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