Stop asking the world what you should do next. Start asking yourself when you were happiest. The answer has been sitting there the whole time.
It’s the question I get more than any other. People sit down, we get through the small talk, and out it comes. What should I do next?
I understand it completely. You have time and energy and maybe more runway than you expected, and you want to spend it well. So you go looking for the answer the way you’d look for a set of keys. Like it’s out there somewhere and you simply haven’t found it yet.
I want to give you the best question I know. But first, let me tell you what the old one does to people.
What That Question Quietly Assumes
“What should I do next” assumes there’s a right answer waiting somewhere, and that somebody else is holding it. A title. A slot you could be talked into if the right person described it well enough. It turns the rest of your life into a problem to be solved, and then hands the solving to someone who isn’t you.
It also assumes you can see forward. You can’t, not from here, and that’s not a flaw in you. You’re asking a version of yourself who doesn’t exist yet to choose the route.
A caterpillar cannot plan the butterfly’s flight path. It has no idea yet what it’s going to be able to do.
You are in the natural, necessary messy middle of your becoming. Nobody plans well from the middle.
A Word About the Word
There’s a name for this part of the work. The vocational terrain. I almost hate saying it out loud, because the second people hear it they think job. Career. Paycheck. Something with a title and a start date.
That isn’t what this is. This is about discovering what’s next for your life, and then for your work, your purpose, your contribution. Life comes first on that list for a reason. Work lives inside a life, not the other way around.
So it might be work. It might also be a garden, or a grandchild, or a guitar you haven’t picked up since 1974, or something you do on Tuesdays that nobody pays you a nickel for. It doesn’t have to be grand. It doesn’t have to be Purpose with a capital P. It has to be yours.
The Best Question
When I was stuck in exactly this spot, my own coach didn’t ask me what I wanted to do. She asked me to look backward.
“Go back through your life. When did you feel the most joy?”
Notice what that question does. It doesn’t ask you to invent anything, or be visionary, or know something you don’t know. It asks you to read evidence you already have. Seventy years of it, in my case. You have been collecting data on what lights you up your entire life, and most of us have never once sat down and read it.
So I did. What came back wasn’t a job title. It was a verb. The thing that had brought me joy over and over, in every setting I’d ever been in, was teaching and coaching. Sitting with somebody while they worked something out.
That’s why I do this now. Not because I finally found the right slot, but because I looked back and believed what I saw.
Why the Answer Tends to Surprise People
Here’s what I’ve noticed. When people answer that question honestly, the answer is almost never the thing they’ve been chasing. It’s usually smaller than they expected, and better.
It’s rarely the promotion. It’s the young person they mentored on the side. It’s rarely the title. It’s the Saturday mornings, or the stretch of years when the house was loud, or the season they spent building something with their hands. Ask people about joy and they almost always answer with a scene, never a résumé line.
That gap, between what you’ve been chasing and what actually brought you joy, is why the forward question keeps coming up empty. You’ve been asking the world for a bigger version of a life you already outgrew.
Stay Interested
A fixed mindset hears all this and decides it’s too late, that the best work is behind you. A growth mindset hears the same thing and gets curious. What would I like to learn now? What have I never tried? People who age well aren’t the ones who found a perfect second act. They’re the ones who stayed interested.
And there’s something available to you now that wasn’t before. The caterpillar consumes. The chrysalis (the cocoon) transforms. The butterfly pollinates. It gives back to the world in a way it never could before, and that’s the part almost nobody tells you about. Not a smaller life. A more useful one, to the people you love and to everybody downstream of you.
I won’t tell you what your next chapter is supposed to look like. That’s yours to discover, and the discovering is the work. But I will tell you to stop asking the world what you should do, and start asking yourself when you were happiest. The answer has been sitting there the whole time, waiting for somebody to ask.
Most people try to sort this out alone. Few succeed, and not for lack of intelligence. It’s just very hard to read your own evidence. I couldn’t do it by myself either. I needed someone to ask me the right question. Now I’m the one asking.
With you on the journey,
Holly
PS — Sign up for your free 30-minute clarity call here. No pressure to enroll on the call. We’ll just talk about where you are and whether this is your moment.