In our culture, there’s a certain vision of what retirement is supposed to look like.

You see it in television commercials: The lovely couple with the silver hair, with polo sweaters over their shoulders, walking hand in hand on the beach, or riding together in a golf cart. Grandparents in sensible clothes with plenty of time to dote on their grandkids.

If you work hard and save a big enough nest egg then by age 65 you can retire and live off your savings, free to live a life of leisure with the few years you have left.

It is a lovely picture from the outside. But the disturbing view from the inside is the unspoken understanding that people who have reached a certain age are expected to gracefully exit stage right and fade into obsolescence. Society doesn’t have much use for them anymore, except perhaps for babysitting. They’ve reached their expiry date.

I took an unconventional approach in my youth, choosing entrepreneurship over a...

In my work as a transformation catalyst, I often work with women who want to change their professional direction but are unsure how.

They are fed up with their current situation. They know what they are doing now does not support the lifestyle they really want - financially, emotionally, aspirationally, or otherwise.

They feel stuck, caught between worlds.

If you resonate with any of the challenges below, let’s explore how to solve them so you can move forward with confidence in the direction you really want to go.

1. Fear of failure and starting over

Going from being proficient at something to being a novice is jarring. And being new at something means not only a lot of learning, but potential failure too. As you embark on your new future—or even simply contemplate it—you may be inundated with concerns like:

• Am I a fool for giving up something good enough for something unknown?
• What will people think?
• What if I fail? How will I recover if I fail?
• What if...