Turning 40 or 50 and want to know what’s next? Ask yourself these questions.

A milestone birthday has a way of kicking up a LOT of questions. And turning 50 really gets those “Now what?” and “What’s next?” questions popping up like a game of whack-a-mole. You might try to knock them back in because they can feel scary and heavy, but they don’t need to.

Take these companion questions for a spin in your journal, a walk in the park, or with you to the shower.

What would be fun?

Once, when I was training to be a coach, I was sitting with a group during a meal break, and I heard myself say, “The problem with fun is…”. Everyone laughed because it sounded so absurd. How could fun be a problem? In reality, it wasn’t. The issue was that I had convinced myself that what was fun for other people “should” be fun for me, and that’s just not always the case. I started to catch myself lighting up and enjoying myself. I love exploring new places, meeting people, hearing their stories, falling down rabbit holes of connections, checking out small local art galleries, making collages, going on walks while catching up with a friend, listening to podcasts, reading, and whenever I find myself in a situation that makes me feel like I’m expanding, growing, learning. I recently had an appointment with Melanie at Vespertine, and putting together colours and figuring out my unique expression was so much fun.

I no longer think fun is a problem, but that took learning and accepting what fun is for me.

What’s the unexpected answer?

I love this exercise. Ask yourself what’s next and then challenge yourself to brainstorm only the unexpected answers. It could be deep sea diving or learning a new language. It could be moving to Paris for a year to study cooking. Let yourself write a list of the most outlandish, unexpected answers and then sit with what comes up.

So much of our stuckness comes from rigidly clinging to a few narrow choices. But when we bust that open, a world of possibility emerges.

What’s the selfish answer?

What would you do next if you had nobody to think of but yourself? What have you put off that might be time for? Suspend any sense of obligation and let yourself think of the most selfish answers. The more selfish, the better. Generate as many answers as you can, and when you’re done, review the list to see what might be possible if you gave yourself permission to put yourself on your list of priorities.

Who’s next?

Instead of focusing on the “what,” challenge yourself to think about the person you want to be now that you’re in this new chapter. What are your values? What are your deal-breakers? What are your priorities? How would you want someone to describe you or introduce you?

How can you be that person? What would you do?

What haven’t I felt ready for, but now I am?

Just because the timing hasn’t been right for something doesn’t mean it never will be. I started my business in my forties. My clients have written books, started podcasts, got into relationships after years of being single, ended marriages after years of being unhappy, taken improv classes, started painting, switched careers, explored their spirituality, and so much more. Years before, they would have told you that thing was impossible, but things change. You can, too.

I never thought I was the entrepreneurial type. That story can hold us back unnecessarily. Challenge your version of a limiting story and see what you have yet to be ready for but want to explore now.

You’re right on time.