Planning in a Time When Planning Is Impossible


Planning is nearly impossible right now. Will schools be back in the fall? Is it safe to fly, and even if we decide it’s safe, will flights be canceled? If you’ve been furloughed, when will you get called back? Will you get called back? How long will COVID be part of our mental calculations. There are just so many things we don’t know. And that is a really tough place to be. 

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I live in Providence, RI which is a college town. We are friends with a couple who work for one of the local universities. They were planning to spend next year abroad as they are on sabbatical. And they were going to leave next month and come back next year. They had their kids enrolled in school, they gave up their apartment. They were outta here.

Now, their plane tickets have been canceled three times. They’ve realized they don’t want to spend that precious year in such an uncertain time—what if they aren’t allowed in? Or allowed back? What if the kids won’t have school, are they going to distance learn in a different language? But if they don’t go, where will they live? While they’re thankful to be healthy and employed, pretty much everything else is in flux. And we’re all facing some version of their situation–it may be better or worse but still, uncertainty is our reality. 

A Buddhist Parable

There’s a buddhist parable about a woman who goes out for a walk along a pretty ridge. And as she’s walking she looks down over the side of the ridge and sees a delicious strawberry growing just over the edge. She leans down to pick the strawberry, loses her step, and is left dangling from a branch. That’s when she looks down and sees tigers pacing on the floor of the valley below. And that strawberry that got her to take the risk is just out of her reach up above her. And that’s it! Ha.

That’s the whole parable. It’s supposed to show that this is where we always live—the tigers are the unknowns about the future that we’re scared of, and the strawberry is the sweetness we remember from the past that we can never get back to. And we’re just hanging in the balance, always, relegated to the present where actually although it may feel perilous, we’re OK. We’re always there but I think this parable feels extra relevant now when the stakes feel higher. 

Keep Planning

And so we naturally want to start planning because that would help us feel like we’ve at least got a roadmap to getting to the strawberry. But it’s like the universe is telling us NO YOU SHALL NOT PLAN. 

Well, I say, you go ahead and start planning anyway, but you also have to be crystal gosh darn clear that those plans are not going to go the way you, well, planned. What this particular facet of this particular moment is here to teach us is flexibility. If you’re really a planner and can’t stand not knowing what’s going to happen, well, make a plan B and a plan C. Maybe plan B is if things work out better and plan C is if they work out worse. 

Regardless, now and always, we have to build our tolerance for not knowing how things are going to work out. It’s a huge piece of being able to be flexible. I know it’s hard. But you know what, it doesn’t just help you roll with disappointment. It also keeps you from limiting yourself—because a lot of times things can work out better than you ever could have planned for yourself. 

Some Things Are Out Of Your Control, And Thats Ok

Which reminds me of the time in my 20s when I worked for an internet start up in the days of the dot com boom. We knew nothing. Options. Going public. Had to decide strategy. What price we wanted to sell them at. Really didn’t know how to choose. Lots of IPOs the stocks were debuted way above their listing price So we collectively came up with double, triple, psycho. Double the listing price. Triple the listing price, and then a price that just seemed bananas to us.

Well, guess what, we blew right past our psycho price. And that is how I came to have enough money to buy my own condo in Manhattan, albeit at a time when you could buy a studio in a prewar building in Chelsea for 100,000 — those days are loooooong gone. BUT it’s an example of this idea that things CAN work out even better than you dared hope. 

So when you find yourself fretting that you can’t plan or that your plans will change, remind yourself, I just don’t know how it will work out. It takes some of this onus off you of figuring everything out and bending the universe to your will. It helps you remember that certain things are just out of your control, which paradoxically, helps you relax. 

Daily Tiny Assignment

And that’s your tiny assignment for the day: when you notice yourself thinking about the future and feeling stressed, remind yourself, “I just don’t know how it will work out.” let’s build our muscles around being OK with not knowing. 

Calm The Eff Down

If you need help quieting your nervous system in the midst of all that’s happening, I pulled all the tips from my 21 Day Calm the Eff Down Challenge (that I ran at the end of April beginning of May here on the podcast) into a pretty mini e-book that can be yours for FREE by going to and entering your email address so I’ll know where to send it.


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