Why Do Women in Leadership Still Feel Trapped? - Box of Chocolate Mindset

Today’s world presents women with opportunities that previous generations could only dream of. For the first time, we have access to career paths and choices that our grandmothers never thought possible, and we’re encouraged to aim for the stars and achieve anything we desire.

But despite these advancements, why do so many women still feel stuck? Maybe this sounds like you—you feel empowered, knowing the possibilities are endless, but at the same time, you’re unsure where to begin. People say, “You can do anything,” yet you’re left thinking, “I don’t see a perfect choice for me.”

In our last episode, we discussed the impact of Limited Role Models and Shifting Values. Today, we’re diving into what I call the Box of Chocolate Mindset—an outdated framework that many of us still lean on when making decisions about our careers.

For decades, the formula for success was straightforward: go to a good school, get a job at a reputable company, and you were set for life. This was the path for my father’s generation—choices were pre-defined, and success was measured by titles and the name of your employer.

But today’s world has changed. With increased life expectancy and more fluid career paths, many of us find ourselves reinventing our careers multiple times. We’re no longer confined to one job for life. Personally, I’ve navigated from academia to the tech industry, navigated from bottom to top in data science, and now I’m an entrepreneur. None of these paths (aka chocolates) existed in the box of chocolates. I had to create my own chocolate (aka path), based on my own desires and vision for the future.

This experience isn’t unique anymore—it’s becoming the new norm. The traditional “safety” of a big company is fading with the rise of frequent reorgs and layoffs. Many people feel trapped, holding on to jobs that no longer fulfill them out of fear. But here’s the hard truth: clinging to the familiar doesn’t guarantee security anymore.

While this uncertainty might feel daunting, it also presents an exciting opportunity. The people who will thrive are those who figure out what truly excites them and use that as their anchor. Relying on old ways—choosing from limited options or accepting whatever comes our way—will only lead to lateral moves with little growth. However, by anchoring yourself to your ideal role and creating your own path, you’ll spiral upward, even through uncertainty.

I'm hosting a workshop exactly for this: "I know I should do something, but what?!" You'll walk away with a clear action plan for your success. Ready to do something now? Join me: https://forms.gle/EJeNrxkpXhwQ7W5P6