Dear Struggling Young Entrepreneur

Some words of peace & practical advice for continuing onward

Emily Steele
4 min readFeb 3, 2023

In the spring of 2016, my boss at the time — an elementary school principal — slipped an “Intent to Return” letter in my teacher’s lounge mailbox.

Below a paragraph of information and legalities, were 2 lines of text, each preceded by 2 checkboxes. It was literally “Check Yes or No.”

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The only consideration I had towards checking “Yes, I intend to return for the 2016–2017 school year” was about the money. I was 22 years old at the time and getting somewhere around $1800 (after taxes) delivered to my checking account via direct deposit every two weeks. It was the most money I’d ever made.

But one day that same year, I left school after teaching 1st period math class because I was “sick” and spent the day crying under the covers until I, quite literally, was sick.

In attempts to comfort me, my mom asked, “What’s the worst part? Maybe if we make the worst part a little better, the rest will feel better too.”

“That I have to go back tomorrow,” I said.

For years my story was that I was just another millennial who hated her job and couldn’t hang.

But I realize now only half of that story is true: I was, indeed, another millennial who hated her job, but my ability “to hang” can not be questioned.

Because after I checked the little box beside “No, I do not intend to return for the 2016–2017 school year,” I resolved to replace my income through part-time jobs and exploring things that both paid my bills and felt fulfilling. And that turned out to be infinitely harder than sticking it out for another year as a 5th grade teacher.

I had the ability to hang all along, I just ended up applying it elsewhere.

Cut to me consuming endless content from YouTubers and Instagram “influencers” before we really even knew what influencers were, and before long I was head over heels in love with the idea of starting a business.

What kind of business, you ask?

a life-coaching business


Me, a ripe 23-year-old, promising to life-coach you through all those big problems and woes I had but only sniffed or read about in Cosmo. But I had seen all these girls doing it on Instagram and YouTube! Why not me?

I took out a hefty loan to pay for one of those online “How to Be a Coach” courses (not knocking all of them, just the one I fell for) and thought I was just a mere hop, skip and jump away from part-time cash-register-girl / personal trainer to six-figure life coach!

**Spoiler alert: it didn’t happen like that for me.**

But something different happened instead:

I replaced my income and supported myself through several different avenues and offerings and pieced together “a career” like a mosaic tabletop.

I continued to amass knowledge, skills, lessons, and little nuggets of wisdom, until suddenly — not by accident but rather by a grand design beyond my own — I had a unique but useful package of Things I Can Do (That I Like To Do), That Some Other People Can’t/Won’t Do But Need Done.

And that’s, essentially, the core of a business.*

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It was a loooooong, long road there, my friends.

I did my share of shape-shifting and crying, and I have absolutely no intentions of saving anyone from any of that. Not because I want to see young business owners suffer, but because:

A) I cannot do that
B) the birth is in the mess.

If there’s anything I hope entrepreneurs or business-owners walk away with after sitting down for some advice or encouragement from me it’s this:

  • do what feels good, and keep doing it
  • have patience and trust that things will add up one day

Steve Jobs said it best, and I have referred back to this countless times on my own journey:

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.”

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I make no promises of your success.

I offer no clickbait headline about “the one thing you need” or “how to make your first million.”

I’m not here to bail you out or sell you on any “tricks,” “secrets,” gimmicks or “hacks.”

I’m just here to do what I can do, that I like to do, that you can’t/won’t do but that you need or want done.

And that is: to teach what I can and share what I believe, in hopes that as you swim out and grasp whatever it is you’re looking for, you enjoy the journey.

As the French say, “Courage.”

To learn more about what I do, click here. To hang out online, find me here. I love learning about others’ career mosaics. Let’s connect.



Emily Steele

lifter of heavy things: thoughts, words, weights, burdensome beliefs