A Love Letter to Women Entrepreneurs Over 50

My dearest entrepreneurial sisters,

How are you?

I’m writing to let you know I’m thinking of you and that I’m so glad we’re on this entrepreneurial journey together. Because, as you know, it can definitely have its ups and downs.

We share so much, you and I — including memories of what life was like before cellphones, the internet and streaming video.

When we were growing up, there weren’t video games or texts or emails that kept us glued to screens. Instead, we played outside from morning until dusk during the summer—only going in the house for absolute necessities (like food and bathroom breaks). We turned our bedrooms into forests or distant planets or veterinary offices — making tents out of blankets and performing operations on our stuffed animals.  No one had to tell us to use our imagination. We just did. And it was magical.

Most of us had one television in the house. And the local ABC, NBC and CBS stations made up the extent of our choices. If we were lucky, we also had the local PBS channel and maybe a UHF channel.

Rotary phones were the only phones we had. There was no call waiting. The only waiting going on was waiting your turn to use the phone. And there was the cord that ran from the handset into the wall or table unit, tethering you to a distance of about three feet or so — five if you really stretched it.

This was the world we grew up in. And it was enough.

For some of our younger entrepreneurial sisters, all of this probably sounds like something from another century. (Oh, wait, it IS from a different century!) They probably can’t imagine living in an analog world that didn’t include all of the technologies today’s kids are seemingly born knowing how to use. And it might even sound a bit scary.

But here’s what they don’t realize: Growing up when we did helped us develop superpowers that put us ahead of the game in being successful entrepreneurs. We have advantages over younger entrepreneurs who never had to do things like ask a friend for a quarter to call their parents from the payphone at the mall.


The Advantages of Being a 50+ Entrepreneur

According to an article on the U.S. Chamber of Commerce website,  a recent study found thatsuccessful entrepreneurs are middle-aged, not young. We find no evidence to suggest that founders in their 20s are especially likely to
succeed. Rather, all evidence points to founders being especially
successful when starting businesses in middle age or beyond, while young
founders appear disadvantaged.”

How about them apples??

Frankly, I was completely shocked when I read this piece — written by Robert Roy Britt.  And I also felt so SEEN.

As I prepare to turn 57 this year, I’m certainly no longer showing up in the “young” category—unless you’re comparing me to someone who’s around 140. But, guess what? I don’t care.

As an entrepreneur, being 57 makes me what the cool kids call “fire” — which is a good thing, BTW. And, if you’re thinking about starting a business (or have already made the jump) — then you’re “fire”, too, my friend.

So, what does being “fire” look like for those of us who are embarking upon entrepreneurial ventures at “a certain age”? It looks like this:
 

We know how to figure things out.

“Don’t know how to spell it? Go look it up in the dictionary.”

I don’t know about you, but I heard that response MANY times when I was a kid who was just trying to get her homework done. Webster’s New World Dictionary was my friend — even though it didn’t always feel that way. I mean, how do you look up a word if you don’t know how to spell it?

This is the dictionary my parents pointed me to on MANY occasions. It's a bit worn. But, overall, it's still lookin' good!

We also had a set of World Book Encyclopedias sitting on the bookshelf in our den. (We were missing a volume, though. I think it was the “M” one.) My brother and I were constantly using them for school projects — or just because we were interested in something.

We couldn’t just do a quick search on the internet to find an answer. (Internet? What’s that?) Instead, we had to really LOOK for it using the prehistoric tools we had at the time — including the beloved card catalog in the school library. Answers didn’t come instantaneously. And we didn’t expect them to.

My point here is that we grew up knowing that we had to figure things out — often on our own. And we did. 

As entrepreneurs, this serves us well. Why? Because there’s a LOT for us to learn and so many new skills for us to develop. But none of that scares us. Because we know we can figure it out — just like we always have.

 

We have more (and often better) stories to tell.

 

One of the best things about growing older is the stories that we accumulate over the years.

Just think about all of the things that have happened in your life. Celebrations, disappointments, friendships, marriages, divorces, successes, failures, heartbreaks, joy, moments of awe, and moments of utter disbelief.

Collectively and individually, every experience you’ve had during the decades you’ve lived in this world makes you more understanding, more empathetic, more insightful and more courageous.

As a woman — and as an entrepreneur — who’s over 50, you have an endless supply of stories you can pull from to create amazing content that will help you connect with your audience.

Even if you’re much older (or younger) than those you serve, there are still ways to use your own stories to teach, enlighten and inspire.

 

The richness and depth of our story supply is something that can only be built with time and experience. And we’ve got TONS of both!

As a woman — and an entrepreneur — over 50, you have an endless supply of stories you can pull from to create amazing content that will connect you to your audience.

 

We don’t have the time OR patience to pretend we’re someone we’re not.

 
When I look out into the world of online content creators, I see so many youthful faces looking back at me. Most of them are male. Almost all are under 40. And none of them look like me or anyone I know.
 
Don’t get me wrong. Many of these folks are AMAZING at what they do. I’m a subscriber to their newsletters and I’ve bought programs and products from several of them.
 
But, try as I might, I’m not like them. At. All.
 
Me? I’m a single, gay woman in her 50s that has a beautiful son, a black Labrador named Zach and a moody (but sweet) cat named Ollie.
 
I love my family and friends.
 
I find teaching one of the most rewarding things I’ve ever done.
 
I crave alone time — but treasure the time I spend with those I love.
 
I enjoy tennis and reading and Marvel movies and NPR. I even picked up pickleball recently.
 
Fancy cars? Fancy food? Fancy clothes? Nope. Not for me.
 
Give me a dependable car, a plate of spaghetti with marinara, and a sweater, jeans and comfortable shoes. Those things make me happy.
 
For a long time, I was really self-conscious about not “looking the part” when it came to creating an online business. I questioned where I could possibly fit in. And I also wondered who would want to listen to me when all of these other really cool, really beautiful, really smart, really successful, really young entrepreneurs were already killing it in the online space I wanted to be in?
 
But, finally, I’m in a place where I’m like, “Hey. This is me. Take it or leave it.”
 
Frankly, I don’t have the energy to try to be someone I’m not. Do you?
 
If someone doesn’t like me or what I stand for, they’re free to scurry on along. The way I see it is that those who like what I’m doing and how I show up will want to join me on this journey. THEY’RE the ones I want to hang out with, anyway. It’ll be a lot more fun for ALL of us — that’s for sure.
 
You be you. The world needs the real [insert your name here].
 
So, come as you are. That’s what I’ll be doing.
 

 

We don’t let change throw us off our game — at least not for long.

 
Whether we’re talking about technology, politics, society, or anything else — you and I have seen so many changes over the past decades. Not just little ones, either.
 
There have been HUGE changes that have reshaped our world over and over and over again.
 
But we’re still standing — and thriving.
 
Change is hard — really hard. And thriving because of it or in spite of it doesn’t happen immediately. It takes time. It requires patience. And it demands a willingness to keep learning and growing.
 
You and I understand this because we’ve had to pivot in our personal and professional lives more times than we can count — and certainly more than we can remember. And, as a result, we’ve become quite adept at successfully navigating it.
 
For 21st century entrepreneurs, change has been and will continue to be a constant companion. You and I? We’re ready. So, bring it!
 

 

We understand that “overnight success” is total B.S.

 
I’ll admit it.
 
When I was younger, I totally fell for the promises of super fast success. I wanted to know all of the “secrets” that were touted as being the keys to easily and quickly reaching my goals.
 
I just needed to buy one more book, one more course, one more program and I’d blast by everyone who didn’t know the secrets I was learning.
 
Well, you can guess how that turned out.
 
I’m not saying I didn’t learn some really useful things from all the different products I bought. I did.
 
But — at least for me — I finally realized that I was going to have to focus on old-school business fundamentals and put in the work if I really wanted to succeed.
 
There were no shortcuts.
There was no simple path.

There was no overnight success.

 
With quite a few bad buying decisions under my belt, I’m now very picky about how and where I spend money to further my entrepreneurial education.
 
Continuing to learn new things is essential to success. No doubt about it.
 
But, now, I have a very short list of people whose advice I seek, whose products/programs I purchase, and who I trust to deliver substantive and accurate information.
 
You and I know that we have to work really hard to reach our goals. Technology hasn’t replaced hard work. But it can certainly help us do things more efficiently.
 
At the end of the day, though, sweat equity is still essential to building a business — whether it’s online or brick-and-mortar.
 

 

We’ve earned the right to do things OUR way.

 
Let me ask you something: When you first set out in your career, did you ever keep a great idea to yourself because you were sure (or afraid) someone would wave it off as silly or just plain wrong?
 
Even when you had a seat at the proverbial table, did you sometimes (or oftentimes) feel unseen and unheard?
 
Did you wonder how some people landed in prestigious positions within an organization when you knew they were completely unqualified? (Oh — and they continued to rise through the ranks unimpeded.)
 
If you never experienced anything like this, that’s great. (Also, I’m jealous.)
 
But if any of these examples ring true for you, here’s some great news:
 
As a business owner, you’re the boss of you. Now, it’s you who’s making the calls, determining what’s best for the company, for your employees, and for yourself. And it’s your vision that will drive your business forward. You’re finally in control — which is exactly how it should be.
 
And one more thing: YOU’VE EARNED THE RIGHT TO DO THINGS YOUR WAY.
 
Justice Ruth Bader Ginsburg once said, “Women belong in all places where decisions are being made. It shouldn’t be that women are the exception.”
 
You, my friend, are NOT the exception. You are now the RULE.
 
You’ve put in the work and the sacrifice to be in a position to build your own empire — whether that’s a one-person business or a global conglomerate. This is YOUR time. So, take it and show the world exactly how amazing you are.
 

In closing, I just want to offer you my sincerest congratulations — regardless of where you are on your entrepreneurial journey. You’ve FINALLY reached the PERFECT age to start a business of your own! Plus, being 50+ looks AWESOME on you!

 
 

With much love and admiration,

Michele

Header photo by Liam Truong on Unsplash

Picture of Michele Lashley

Michele Lashley

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