Why Women Over 40 Are the Most Underestimated CEOs

Her Counsellor Laughed at Her Dreams.

Now She Runs a Nine-Figure Tech Company and Raises Six Kids.

Why Women Over 40 Are the Most Underestimated CEOs in the Room.

When a high school counsellor looked at a bright, ambitious teenage girl and laughed at her dreams, she made a decision. Not to shrink. Not to find something smaller to want. She decided to prove him wrong. And she has been doing exactly that ever since.

This week on the podcast I sat down with someone who is running a nine-figure tech company, raising six children across completely different life stages, writing her second book, hosting her own podcast and doing all of it with a kind of calm and grounded presence that honestly made me stop and think about how I am running my own life.

But here is the thing. This conversation is not really about how impressive her list is. It is about something that I think is far more important and far more personal than that. It is about what we as women, as mothers, as women stepping into our next chapter, have been doing our whole lives without ever understanding how powerful it actually makes us.

 

We have been running organisations all along. We just never called it that.

One of the first things she said that really stopped me was this. We haven’t empowered ourselves with the proper language to own what we do at home as the high level skilled labour that it actually is.

Aimee Rickabus - Her Counsellor Laughed at Her Dreams. Now She Runs a Nine-Figure Tech Company
Think about what you actually do on any given day. You manage people. You manage systems. You manage calendars, budgets, emotions, conflict, inventory, relationships. You project manage constantly and often invisibly. You solve problems before anyone even notices there was one. You create the culture that your entire family lives inside of every single day.

If someone was doing all of that inside a business they would have a title. A salary. Probably a team underneath them and a seat at the leadership table. But because we do it at home, because we do it as mothers, we have been conditioned to call it nothing. To wave it away. To almost apologise for it when someone asks what we do.

She asked her therapist to help her write down everything she was managing at home and she said she wasn’t even sure she could make the list long enough. Because there are so many intricacies to the work we do that we don’t even register them anymore. We just do them. Automatically. Constantly. Without ever stopping to recognise that this is genuinely skilled work that the world could not function without.

And that has to change. Not just for our own confidence. But because every single one of those skills, every bit of that invisible expertise, is exactly what it takes to build a business. To lead a team. To show up as a visible credible woman in your next chapter.

Presence is not a luxury. It is a skill and it needs to be practised.

Something that really stayed with me from this conversation is how she thinks about presence. Not as a nice idea or something she aspires to. As a genuine daily practice that she protects fiercely.

When she is with her children she is with them. Phone away. Do not disturb on. Fully there. When she is working she is completely in it. No crossover. No half attention. And she talks about this not as something that comes naturally but as something she has had to learn and keep choosing.

She gave herself nine uninterrupted hours to finish her book and got it almost completely done in that one block. Nine hours of full focus versus the same nine hours fragmented across a week of interruptions. The output is completely different. The quality of it is completely different. And so is how she felt at the end of it.

And I think about how rarely most of us actually do that. How often we are half in a conversation with our kids while checking a message.

Half in a work task while thinking about what needs to happen at school tomorrow. We are everywhere at once and nowhere fully. And then we wonder why we feel so depleted even when we haven’t stopped moving all day.

Presence is the thing that makes everything else possible. One focused hour with your children matters more than a whole distracted day.

One deep uninterrupted work block moves things forward more than a week of fragmented effort. This is not about doing more. It is about actually being in what you are doing.

The technology conversation nobody is having honestly enough.

Here is the thing that genuinely surprised me in this conversation. She works in tech. She runs a nine-figure technology company. And she turns the wifi off at ten o’clock every night. Phones go on airplane mode. Screens go away. Her children sleep without devices in their rooms and they have healthy sleep patterns because of it.

And then she said something that I haven’t been able to stop thinking about. The higher up you get with the people who actually build this technology, the stricter the rules they have around it in their own homes and especially around their children.

The people who build the apps know exactly what they do to our attention. They know because they designed it that way. And the most senior among them have quietly built walls around their own families while the rest of us are still sitting in the boiling water wondering why we feel so anxious and distracted all the time.

She has a master’s in film and television production and she talked about how media has been shortening our attention spans for decades. From episodic television to music videos to the relentless cut cut cut of early 2000s filmmaking to social media and now reels and short form content. Our brains have been systematically rewired for shorter and shorter bursts of attention and we walked straight into it without realising what was happening.

The solution she talks about is not dramatic. It is a power strip on a timer. Phones in a drawer for one hour. Notifications off. One hour where you are just there. She says everything will be okay for one hour. And she is right. But we have to actually decide to do it.

The patterns we inherited that are quietly working against us.

Something she said that really resonated with me is this idea that we are allowed to audit what we have inherited from our mothers. We are allowed to look at the way we are doing things and ask honestly, does this still serve me? Does this still serve my children? Or am I just carrying it because nobody ever told me I could put it down?

She talks about toxic female traits. And I know that phrase sounds harsh but she means it kindly and I think she is right. The not asking for help. The not admitting when it is hard.

The performing okayness when everything is falling apart. The doing it all quietly so nobody feels burdened.

These patterns go back generations. She talked about germ cells, about how these stories of what we are supposed to be and how we are supposed to cope are carried in our DNA from ancestors who genuinely could not afford to be seen as difficult because the stakes were survival.

But we are not in that world anymore. We are not going to be left behind

by the tribe for saying this is hard. For asking for help. For putting something down that was never really ours to carry in the first place.

And the women in our lives, our mothers included, they weren’t doing it wrong.

They were doing what they knew. But we know more now. And we get to choose differently.

The blind spots that show up where we least expect them.

One of the most honest and vulnerable moments in this conversation is when she talks about the blind spots she discovered through journaling and through working with AI as a thinking tool.

She said something that I found really striking. She carried a childhood wound of feeling insignificant straight into her marriages. Not her business. Not her parenting. Her marriages.
She grew up with a mother who worked constantly and was not always present even when she was there.

And that feeling of not quite mattering, of not being seen, sat quietly inside her and then walked into every intimate relationship she had. Twice. The same pattern twice before she was finally able to see it.

And she only saw it by writing it down. By journaling.

By being honest enough with herself on paper to make connections she could not make in her head. She even talked about using AI as a thinking tool because sometimes, she said, you can be completely honest with it in a way that is hard with other people. And sometimes that honesty is what finally lets you see what you have been carrying.

She talks about getting out of your own blind spots as one of the hardest things we can do because some of them have been there our whole lives. We don’t even know they are there.

They are just the water we swim in.

And the reason this matters for women building businesses and stepping into visibility in their next chapter is because those blind spots come with us. Into our work. Into how we show up. Into whether we believe we belong in the room or not. Doing that inner work is not separate from the outer work of building a business.

It is part of it.

Building something that actually fits your real life.

One of the most grounding parts of this conversation for me is when she talks about what building a business actually looks like for women over 40 who also have a family and a life and a whole other world that matters deeply to them.

She is not advocating for the 60 hour founder hustle. She is not telling anyone to sacrifice their family on the altar of ambition. She is saying something much more useful than that. Find something you are passionate about. Something small to start. Something that lets you still pick your kids up from school. Something that is yours.
And she points out something really practical that I think a lot of women don’t think about. When you have your own business, even a small sole proprietorship, you get tax benefits that an employee never sees. You get flexibility that a job will rarely give you. You get to build something on your own terms in your own time in a way that fits the season of life you are actually in.
She talks about women in her neighbourhood who made this work. A myofascial therapist who used to work 40 hour weeks as a dental hygienist and couldn’t make it to school events. She retrained, built her own practice, now works on her own terms and is one of the happiest most well-adjusted women she knows. That is what a next chapter can look like. Not perfect. Not a nine-figure company on day one. Just something that fits.

We do this better together.

One of the things she said that I loved is her vision for what changes when women stop competing and start cooperating. She talked about a group of five mums in a neighbourhood who each cooked dinner one night a week for all five families. Five families fed. One cooking session each. That is it. That is the whole thing.

And it sounds so simple but it points to something much bigger.

So much of what exhausts us is the isolation of it. We are trying to do work that for most of human history was done communally, with mothers and grandmothers and sisters and aunties all around us, and we are doing it alone on these little islands of nuclear family life and then wondering why we are running on empty.

She genuinely believes that women are going to be the ones who figure out how to use technology to build those communities again.

To find the cooperation. To solve the problems that are making women’s lives harder than they need to be. And I believe that too.

Your next chapter is not starting from scratch. It is starting from everything.

She started flipping houses at 22. Had five million dollars worth of real estate by 25. Started a production company. Then a nutraceutical company. Then a tech company with her husband. Grew it through COVID while he was seriously ill and she had to step in for everything. Built it to nine figures.

And when her high school counsellor laughed at her dreams, when neighbours came to her door asking where her parents were because surely this house couldn’t belong to someone who looked like her, every single one of those moments became fuel. That is the word she uses. Jet fuel.

She is not telling you your past pain is a gift in a soft greeting card kind of way. She is saying pick it up, use it, let it push you somewhere. Let the doubt of other people become the thing that proves them wrong.

Women over 40 are not starting over. We are starting with everything we have learned, everything we have managed, everything we have built and survived and adapted to. We are the most underestimated people in any room we walk into.

And that is actually an enormous advantage if we decide to use it that way.

The full conversation is live now. I think you are going to love it.

Our Guest:

Aimee Rickabus is an entrepreneur, author, and podcast host dedicated to redefining women’s leadership. As the author of The Manage Her and host of the podcast by the same name, she highlights how the invisible labor women perform every day translates into systems thinking, problem solving, and leadership skills that transform business and community. Aimee is also CEO of Tomahawk Information Solutions, a woman- and minority owned technology company. A mother of six and lifelong advocate for women, she inspires audiences to see their potential not just as professionals, but as whole, powerful individuals.

Aimee Rickabus – Instagram 

The Manage Her Book on Amazon 

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