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The Question to Ask Yourself Every Time You Start a Project

A two-step system to end everything you do on the right note

Illustration: Dora Godfrey/Medium

Early in the pandemic, I started a podcast called The New Corner Office, featuring a short daily tip on how to work successfully from home. When I began this project, I assumed that it, and the pandemic, would be short-lived: Everyone would hightail it back to the office in a few months, and I’d adjust accordingly.

Then “two weeks to flatten the curve” stretched into months. Eventually, 200 episodes in, I realized I was going to need to make a conscious choice. In November, I decided to end the podcast with 2020, and I published my last episode — what I called “The New Corner Office Manifesto” — on New Year’s Eve.

The experience got me thinking about endings generally. Beginnings are sexy and fun and easy to get excited about. But whenever we start new projects, we should also be asking ourselves the question: “How will this end?”

There are two steps to the process.

Step 1: Schedule a checkup

In her book The Art of Gathering, event organizer and facilitator Priya Parker notes that “too many of our gatherings don’t end. They simply stop.” We’ve all been there. Things peter out. Book club gets harder to schedule, and fewer people show up. A no-longer-useful weekly meeting clings to the calendar, with people scheduling over it, hoping the convener will eventually put it out of its misery.

As Parker writes, “Great hosts, like great actors, understand that how you end things, like how you begin them, shapes people’s experience, sense of meaning, and memory.”

I like to set a scheduled checkup date, at which point the purpose of the event/meeting/project can be reassessed. For example, if you’re starting a book club for the first Wednesday of each month, you might schedule the first six months: dates, hosts, agenda format, book choices. Then, after six months, you decide as a group whether to keep going. If so, schedule the next six months. If not, then the last gathering can be a celebration that you had a good six-month run. You’ll think of this last meeting as you might a graduation ceremony, rather than as a failure.

Likewise, the new Monday morning staff meeting might come with its own expiration date. You try it for the next 12 weeks and then evaluate whether it’s adding enough value to your organization to justify the cost in staff time. If so, great. If not, you try something else.

Step 2: If you’re done, end things mindfully

To paraphrase Brad Paisley, we might not even know when we’re doing something for the last time. There will be a last time your kids wake up at the crack of dawn to see what Santa brought, and a last time you visit your grandparents, and a last time a friend or client calls before the relationship peters out, but we rarely recognize the last time when we’re in it. When you can shape the experience, you might as well.

So, with my podcast, as I stared down some new commitments in my life, I decided to consciously wind it down, even though we’d just turned a profit and I hadn’t run out of things to say. I chose a meaningful final date and produced a last episode summing up what I’d learned. That way it felt more like the end of a series, rather than something chucked unceremoniously aside because I got too busy or ran out of steam.

I think my listeners felt this was a good approach. I certainly felt better about it. And since all things do end, the more endings we can feel good about, the better our lives will be.



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