What Questions Are You Not Asking?

I’ll start — I wasn’t asking myself any of them. Like none.

Solo time during quarantine led to restlessness pretty quickly. After a baking hour here or time setting up Zoom calls there you start realizing that you run out of things to fill time with when you have a surplus of time and a finite number of things.

Eventually that restlessness became a call-to-action to stop filling time with things to do. Instead, something happened — I can’t tell you how it came to be— but I started asking questions. The kind that sit well with your soul, but definitely don’t please your ego because it definitely thought it already knew everything.

But when the questions started landing on:

Did I like New York?

Did I like my job?

Did I want to achieve the dreams I’d been working towards or did I just like having dreams to work towards?

And I realized the answers weren’t immediate affirmations, my ego got real uncomfortable. I kept pushing though because the discomfort didn’t feel wrong, it just felt unfamiliar.

The answers I landed on, for now, are irrelevant. I want to stick to the questions and why I had never asked them. Why we never really ask them.

Along the way of growing up we place ourselves on a conveyer belt of events that are supposed to happen. The to-do list we inherit includes going to school, learning enough about subjects that you don’t like to land on one that you do, going to school some more, finding love, getting married, having a family, getting a house, and growing old there. Then we’re split into groups.

There are those who follow the to-do list blindly and maybe never jump off the conveyer built.

Those who know enough of themselves take the list and customize it based off who they believe they are then. In their mind who they will be in the future won’t (shouldn’t) stray too far. So they’ll move one item up or cross out the ones they definitely don’t think apply.

I’ve been in that group up until this year.

I knew enough of myself at 21 years old to give myself a roadmap. I wanted to build my career before I built a family. I wanted to be a creative. I wanted to write and live enough to have things to write about.

I failed myself though — I never baked in rest stops. I didn’t account for moments where I could stop, get to know myself again, and reassess if where I was going was still where I wanted to go or if I still wanted to get there by way of the road I’d chosen.

Quarantine demanded this of me. I think we should get in the habit of demanding this of ourselves. Constantly. Vigorously. Honestly.

***

On Sunday, I was talking with one of my best friends about her job and where she would go next if she was to get laid off.

“I don’t know what I would do if it happens,” she said.

I was perplexed. I knew exactly what she would do.

“That’s a lie, you know exactly what you would do — you’d cry for a bit and then you’d find another job,” I said.

Then I added,

“I think you shouldn’t ask yourself what you would do in that moment — instead ask yourself if that’s even what you want to do.”

I was a hundred percent propelled to say this to her because of the biggest questions I started asking over the last two months — Do I want this? If yes, why? If no, that’s fine, but what do I want instead? — topped my list.

My friend has the chops, the expertise, and the outlook on life that would make starting her own business not only a viable option, but a successful, fulfilling, and happy one. It’s not her only option, but it is one available to her if she asked. She’d just never asked herself if she’d reached her stop on the conveyer belt or if it was time to switch to a different one.

She did a version of what I did. Like me, maybe she took her 21-year-old self’s word as the end all be all to where she’d always have to go. I knew myself enough at 21 to know where “there” needed to be.

“I’m working to go there.” Fill in the blank for all the things I’d attached there to.

Today I am 27.5 years old. It’s a world of new questions and drastically different answers. It will always take getting to know yourself to know how to answer them for yourself, but don’t just get to know yourself and leave the information on the back-burner.

Ask yourself what questions you aren’t asking yourself.