How Karen Robertson’s ‘wrong wall’ story might help you climb the right one!

Recently, Second 50 Co-Leader Karen Robertson shared a fascinating story about success, with an important lesson for any woman considering building something new in her Second 50.

Karen first told this story in our Possibilities Lab, and it surfaced again as she developed the Right Wall Workshop for Second 50 women.

It shows why, before investing our precious time, energy and talents in bringing any dream to life, it pays to consider whether our ladder is leaning against the right wall.

The Adventures of Treasure Kai (and Karen)

In 2007, Karen literally woke from a dream with an idea for an interactive children’s book that could make reading more engaging for reluctant readers, including her dyslexic sons.

“I wrote the book as a choose-your-own-adventure story, where toys hidden in treasure chests became clues,” she says.

Treasure Kai combined story, clues, toys and an illustrated treasure map to engage reluctant readers.

Self-publishing was unusual at the time, so bringing her idea to life involved much more than writing a book. Karen had to create an entire product and business around it.

“I created the business, built and packaged 5,000 books, and then sold every one of them,” she says.

The physical reality of a big idea: Karen with 5000 packaged books ready for sale.

She loved the creativity, learning and challenge of turning her idea into something real. But gradually, she recognised something about her success: Being a children’s author was not quite her jam.

What truly energised Karen came next. After transforming the book into one of Australia’s early children’s book apps, people began asking her to show them how she had done it.

“I went on to write guides, run workshops and help more than 50 authors bring their own children’s books to the iPad,” she says.

Karen’s next chapter: teaching and helping other authors bring their books into the digital world.

Through that experience, Karen discovered the combination that fitted her: writing, teaching, coaching, marketing and helping other people bring their ideas to life.

We can climb the wrong wall more than once

Karen’s story is worth sharing because the wrong wall does not always look wrong. It can be exciting, worthwhile and successful, but still not suit the life we want to live.

Also, book publishing was not the only wrong wall Karen has built her ladder against. She did it again, more than once, and in different ways, many years later.

Each time, she didn’t know what questions to ask about her new possibilities beforehand.

She applied what she had already learned, but each new possibility had a new wrinkle she hadn’t seen coming.

In our Second 50 years, we should be less willing to spend precious time, energy (and money) discovering this too late.

That does not mean avoiding new possibilities, not making mistakes or shrinking our dreams.

It means testing our possibilities before investing deeply, and paying attention to what the everyday reality might give or take from the life we truly want.

Karen’s book publishing climb was not wasted.

In fact, it became a steppingstone towards work that suited her better and helped her gain an understanding of what genuinely energised her.

The right wall will look different for every woman, but the opportunity to evaluate and know what we are getting into fits us all.

How Karen keeps writing her own next chapter

When Karen said yes to leading our Solopreneur Mentoring Group in early 2025, it reawakened her curiosity about how she could use everything she had learned to help other midlife women explore their possibilities.

“It was hearing women in the group describe that very same pattern of stepping into something that looked right, but wasn't, that got me so curious,” she says. “I had done this myself, more than once.”

So, she started asking a simple question out loud: is this possibility up against the right wall?

Eighteen months later, Karen has found a new expression of her "jam".

As a Co-leader of Second 50 and creator and facilitator of the Second 50 Possibilities Lab, she is helping midlife women (like her) take their ideas forward — testing them, gathering honest feedback and evaluating whether they truly fit.

Sometimes an idea grows stronger; sometimes it changes direction; and sometimes a woman realises that the wall she was preparing to climb was not the right one after all! Phew.

Gaining that clarity is incredibly valuable. Too many programs encourage us to move quickly: to invest in fancy platforms, launch quickly and add all sorts of bells and whistles to attract attention. What they often don't tell you is how expensive and energy-sapping that process can be, or help you truly evaluate what you are building and why.

It is only recently that Karen has taken her big question and turned it into something concrete: a methodology women can use, rather than just a feeling to sit with.

“I don’t want to just help Second 50 women bring ideas to life,” she says. “I also want to help them decide which ideas are genuinely worth building.”

There is something wonderful about the fact that Karen has chosen to do what she does inside our Second 50 ecosystem.

"Second 50 women energise me, and it is so rewarding to lead the Possibilities Lab space, where none of us have to work everything out alone," Karen says. "Women bring their emerging ideas forward, think out loud in a structured format, draw on the wisdom of the brains trust and take their next step with more clarity."

As Karen keeps writing her own next chapter, she is passionate about helping herself and others make sure the wall ahead is truly worthy of their precious time, energy and talents.

I am deeply grateful to have met and befriended Karen through Second 50, and that she is so generously and authentically helping us shape what comes next, together.

Karen Robertson is leading this learning workshop for Second 50 members.

Sage Advice Live: The Right Wall Workshop - How To Make Sure Your Next Possibility Truly Fits Your Life
Tuesday 11 August : 1pm-2pm AEST (on Zoom)

Join Second 50 to be part of the The Right Wall Workshop to learn and take-away a practical framework for evaluating any new possibility + powerful questions to help you decide what is right for you.