Nicholas had it all. With a loving wife, healthy children, a condo in a vibrant neighbourhood, a strong track record in a leading organization, and multiple family vacations each year, he lacked for nothing.

Nicholas recognized his good fortune and was grateful—but he wasn’t happy. He wished he had explored his interests and passions more when he was young so that he could figure out what he wanted to do for the rest of his life. Instead, his parents chose his career for him.

Now, with a family and a mortgage, he was wrestling with the question: Is this all life has to offer? Is he to spend the rest of his life providing for his family and continue suppressing his unhappiness?

Nicholas hasn’t discussed a midlife career change with his wife because he feared she wouldn’t understand.

His coping mechanisms, like occasionally escaping for drinks, were already causing friction at home.

If he doesn’t lead with his passion, if he doesn’t break through the wall of expectations of what life should be as a man, husband, father, then both his wife and children will be deprived of the best version of him.

Together, we created a reversible roadmap that reflected his talents and passion, which he was already spending ample time on as a hobby.

Nicholas had some work to do before he was ready for an honest conversation with his wife about his midlife career change. Being his Sherpa, I held his hand, gently removing obstacles from his path.