You may remember study hall as social hour—I know I do.

With minimal supervision, my friends and I wrote notes to each other, passed around headphones to listen to music, chatted, and flirted.

But that was in high school, when our study habits (or lack thereof) were firmly established and socializing was our priority. When we went home, some of us did the work and some of us did not. Where did we learn these habits? In middle school. And that’s where educators have a unique opportunity to teach students not only the material under study, but how to study, setting them up for successful careers in high school and beyond.

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I am grateful to my longtime mentor, Neil Bainton, for his perpetual nudges toward clarity.

We’d meet for a meal where I’d talk about my plans for my business or whatever, sharing the various options and possibilities I was considering.

Neil would never get mired in the details. He always brought the conversation back to one simple question: “What do you want?”

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Working with fellow business owners, I see patterns arise in the concerns and insecurities we share.

It is common for these leaders, be they entrepreneurs or freelancers, to believe that they aren’t real business owners for one reason or another.

Their website still needs work. Their social media accounts are placeholders. They haven’t figured out how to file their quarterly taxes. They’re just winging it when it comes to sales.

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As a business owner, I often hear from friends (and friends of friends) who are headed down that path. They’re looking for advice and encouragement.

Often, I can’t help very much — we have a mismatch of values and priorities.

One woman called wanting to learn about finding commercial space for a school she hadn’t started yet. She was disappointed in my recommendation that she start humbly (for instance, leasing from a church) instead of forging ahead with a multi-year commercial lease in a high-traffic area. Her plan was to raise money, which sounded terrifying to me.

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One of the things I enjoy about life in 2020 is how easy it is to travel light.

I can run multiple businesses from a laptop and smartphone. I’ve got a camera, calculator, address book, and anything else I might need, right in my pocket.

Under such circumstances, I might be able to get away with the illusion that I’m independent — self-sufficient. But nothing could be further from the truth.

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