Karen, 55

Courageous, optimistic, resilient

“I'm at a place in my life where I don't feel like I have to prove anything. I'm smart, experienced. I know what it takes to get things done. I can see around corners to pitfalls that could impact our business and I know how to pivot when needed.

Twinsight: So many things about Karen’s story inspire us — using her magic hour to tackle a global social problem, not to mention her innovative leadership in a youth-driven tech industry. But perhaps most of all, we love how she’s bringing the best of different generations together to make all this happen and along the way, finding and striking common ground.  Check out her story, and share your multi-gen successes and challenges.


Three years ago, mid pandemic chaos, Karen Olsson felt alone caring for her aging mom in the mid stages of Alzheimer's — and all this while trying to run a business and raise a teenager. At the same time, a millennial mom of four faced her own challenges just miles away.  A public health nurse, Ashley Stone had just given birth to twins in a surprise third pregnancy.  Both women struggled with isolation and finding meaningful help with their different challenges. That’s when the two connected. And immediately, they bonded over one big idea. 

The Village App would be a go-to technology for creating kinder, more empathetic communities.  Unlike other attention-based social platforms that can perpetuate isolation, this would be intention-based. It would push online connections into the real world, connecting real people with real actions and solutions.

“We were at very different stages of life, but feeling the same need for help and with no real easy, clear way to access it,” explains Karen. “Ashley's idea was to create a simple app that would allow people to give and get support where and when they needed it without the toxicity of traditional social media. I ran a technology consulting company and had the capacity to build the technology.  Together we set out to create The Village App.”

Fast forward three years, the Village App launches. “A large part of our success is our age difference,” insists Karen.  “I'm at a place in my life where I don't feel like I have to prove anything.  I'm not in competition with Ashley. I'm smart, experienced. I know what it takes to get things done. I can see around corners to pitfalls that could impact our business and I know how to pivot when needed. Ashley appreciates those things about me. At the same time, Ashley is smart, focused and incredibly resilient.  She brings big ideas and boundless vigor to move the needle on our business.   Our ages are different. Our generational experiences are different.  Even our energy levels are different, but our values align and operate around trust.   It's one of the best partnerships that I've ever been a part of. Together, I think we’re unstoppable!”

 We agree.

Karen and Ashley. Our values align and operate around trust. Together we are unstoppable!

How old are you and how do you feel about this age?
Just turned 55 two weeks ago, TBH it's a bit terrifying, but I also have this big sense of coming into my own, and giving no shits about what other people think. 

What’s one life lesson that you wish you had known earlier?   

Everyone feels like an imposter at some point and most people are just winging it. 

Have you experienced ageism?
I work in tech, and ageism is there every day dealing with clients and partners. I find it is most pronounced in the efforts around getting our startup funded.  

What’s your message to the world?
Be you, fully.

What’s next for you? What does your future-self look like? 

More entrepreneurship, more collaboration, taking my company all the way to a successful exit, more hiking, more travel, more Canadian authors.

Do you feel visible? 

Not always, I feel like I don't do a good job of making myself known and because I'm a "modern elder" I feel like I'm naturally overlooked at times.

Are there things you are doing now that you couldn’t do before? 

I'm more confident and more in tune with my life, I don't let others stop me from doing what I want.

Learn more at The Village App and on LinkedIn

Our Twinquiry: What successes or obstacles have you had bridging generations — in work teams, a community group, in family, or just tackling any big new idea?  Let’s get the conversation started. Reach out to us here.

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Colleen, 65