I would send you a bouquet of newly sharpened pencils
I’m a huge movie buff. I love everything from stupid comedies to black-and-white classics to gory horror. Cinema tells us stories about the human condition of living.
Every fall, I think about a line from one of my classic favorites, “You’ve Got Mail”:
“Don't you love New York in the fall? It makes me wanna buy school supplies. I would send you a bouquet of newly sharpened pencils if I knew your name and address. On the other hand, this not knowing has its charms.”
In Florida where I live, the weather doesn’t cool down until October, so the only way we know it’s time for the season to change are the Target and Wal-Mart displays of colored pencils and binders.
I don’t know a single person who can walk past those school supply displays and not feel something. If you were like me and really loved school, maybe it’s a bit of happy nostalgia. (Maybe it’s more like “remembered dread”, if school wasn’t so fun.)
But no matter how you feel, going back to school is a universal American experience. Whether you are sixty or six, you feel that combination of nerves and excitement that came with the start of a new school year.
Starting a new school year hits upon a deeply human feeling – the ache and thrill of starting again.
Starting a business feels a lot like the first day of school
If you’ve ever launched a business or new product, you know that strange combination of excitement and nerves. Your brain says, okay, let’s do this exciting thing, and also how am I going to survive if this doesn’t work? You’re standing at a threshold, about to walk into something you’ve never done before.
After all, it’s a tough time to run a small business. The 2026 Bluevine Business Owner Success Survey (BOSS) Report found that a large share of small business owners regularly lose sleep over their finances specifically. The delicate timing between income and expenses is particularly weighty. 49% of small business owners reported questioning at least monthly whether entrepreneurship or running their own business was worth it.
But most small business owners got into their ventures because they wanted a different way of living, where someone else didn’t dictate how high they could rise or how they could manage their time.
While it can feel tempting and nostalgic to go back to an easier time when someone else worried about payroll and the bottom line, there’s a reason that business owners started in the first place.
Fear is just what comes when you care deeply about how something is going to turn out.
Why new businesses need the teacher in the doorway
What does this have to do with going back to school, you ask?
I invite you to think about the best teacher you ever had. He or she was probably calm and confident. Warm and passionate about the work they did in the classroom.
The best teachers know that twenty students walk into their room with twenty different types of nerves from twenty different home lives. And they are happy to meet them right where they are at, knowing that they’ve done this before even if it may look different for this class.
My first best teacher (and I’ve had many) was my kindergarten teacher, Mrs. Harris.* Contrary to who you see today, five-year-old me was a basket-case of shyness and fear. Like a lot of bright kids, I had a very rich internal world that in no way showed up on the outside.
And she literally took my hand and walked me around the classroom to let me know how much fun we were going to have. She exuded the confidence of a dozen first days, while holding the tension that today was each of these children’s first day.
Your favorite teacher knew that you could do this and their calm energy had you believe it too.
An experienced teacher acknowledged the discomfort that comes with starting or learning something new. They recognize that their students are doing the hard thing, but then push them to do it anyway. They hold the room steady with their belief in the capacity for human growth.
(On a side note, based on global data from the Gallup CliftonStrengths assessment, approximately 10% to 12% of people have Belief in their Top 5 strengths, which is in the middle of the pack for Strengths. It often goes hand-in-hand with Responsibility, and you can see why. I really love working with people who have this Strength, even though it isn’t one of mine!)
Business owners deserve their own version of that teacher
New business owners need someone like the best teachers by their side to help eliminate the fear of starting something new through warm confidence. Fear is baked into the process of starting a business or launching a product. You’re not going to talk a founder or CEO out of their fears. Their fears serve a purpose.
But what they do need is a steady person who has walked these hallways enough times to know where it leads, even when you can’t see around the corner just yet.
So don’t go it alone. Remember to cultivate mentors, team members, or partners who come alongside you and remind you that fear is normal but that it will be okay.
It can mean the difference between white-knuckling your way through a tough year to having someone beside you to say, I’ve seen this before. Here’s what happens next. We’re going to be okay.
Don’t stand in the doorway by yourself.
One lesson from the back to school season
There’s lots of lessons I can write about related to the back-to-school season.
But today’s is: it matters who’s in the room with you. A calm, present, experienced hand can turn a nerve-wracking first day into the first step in a long journey.
It’s the whole reason I like working with small businesses – because together, we can do something really amazing.
So here’s to new pencils, new ventures, and the good people who do the work.
And remember: “this not knowing has its charms.”
With pencil shavings and good company,
Laney
*A footnote to say that Mrs. Harris promised us when we graduated kindergarten that she’d come to our high school graduation if we invited her. She was true to her word: there at my IB graduation ceremony in May 2005, just as she promised. And we’re Facebook friends to this day!