Moving On


Painting by Doug Webb, “Moving On”, 2021
Acrylic on linen, 20 × 16 in | 50.8 × 40.6 cm

Autumn has come to the Magic City.

The last of the avocados has fallen; the plumeria trees, which many weeks ago shed their blossoms, are now busy shedding their leaves; the coffee shop down the street has been playing the holiday hits—on endless repeat—for many weeks now.

All this signals the obvious:

It’s time to start saying good-bye to 2023!

About good-byes

I was looking through an art magazine a few days ago when I came across a Doug Webb painting that really hooked me.

It’s a scene of a boy, all of 11 years old, maybe 12, standing on a rocky sea shore looking at his beloved teddy bear sail away from him, forever. Teddy’s tiny sailboat is being swept away by the wind and the sea. He’s headed towards a distant horizon somewhere off in the uncertain distance, far outside the painting’s frame of view. Teddy seems to wave good-bye to the boy. In turn, the child’s right hand is positioned above his eyes in what I imagine to be a shaky, teary-eyed salute to his old and faithful friend.

The painting is titled, “Moving On.”

According to Webb:

The painting depicts a young boy saying goodbye to his faithful childhood companion, Teddy Bear, as he begins his transition to adulthood. It was inspired by the Bible scripture:

“When I was a child, I thought like a child, I reasoned like a child. When I became an adult, I put the ways of childhood behind me.”
-Corinthians 13:11

My Aha moment

True confession. I’ve been an entrepreneur for a good long time. I’ve spoken to thousands of small business owners in the past 15 years and I’ve coached hundreds of them one-on-one. All this experience, my own and that of others, led me a few years ago to a eureka moment.

I’ve come to realize that it’s not the technical aspects of launching, running and growing a small business (or a business of any size) that is the obstacle to growth.

By technical aspects I mean all the hard-skills they try to teach you in MBA programs.

Stuff like:

  • How to write a proper business plan;
  • Calculating your COGS;
  • How to put together a balance sheet, profit and loss statement, and cashflow analysis.
  • How to calculate your break-even or ROIC.
  • Price elasticity, choosing a pricing strategy, or the 4 Ps of Marketing.
  • And Porter’s five forces;

On and on, yada yada…

In case you haven’t noticed, we’re drowning in how-to information. Just Google any of the above topics and see what I mean. None of it is a mystery. Knowledge abounds! So do MBAs.

And yet, despite this oceanic reservoir of knowledge, the struggle or failure rate of businesses of any size remains steady and too high for my taste.

It’s not, of course, that technical know-how doesn’t matter. Of course it does, but the lackluster results despite all that wealth of readily accessible knowledge suggests that it’s not the paucity of technical knowledge that’s blocking our thriving as entrepreneurs.

It’s something else entirely.

But what?

One word.

Mindset.

According to Merriam-Webster, a mindset is “a mental attitude or inclination; a fixed state of mind.”

In other words, mindset is the compendium of stories we tell ourselves about ourselves and the word-at-large. Too often those stories are crafted to help us stay in our well-explored comfort zones, where we can effortlessly maintain a sense of safety.

These comforting but limiting stories are the Teddy Bears we need to move on from.

Before the year’s end…

A useful exercise might be to take a hard look at Doug Webb’s painting and ask ourselves:

What are the Teddy Bears we need to say good-bye to?

What childhood thoughts or childhood reasoning are we clinging to that we need to move on from?

What stories are no longer serving us that we should let go of in 2024?

Too often I hear things like:

  • “I’m not good with numbers.
  • “I can’t write.”
  • “I’m terrible with money.”
  • “I could never be a good public speaker.”
  • “I don’t have anything to say that people would be interested in.”

But none of that is actually true.

Those are all excuses, often created during our early years. They’re the Teddy Bears or security blankets that we cling to because it can be scary to try something new and unknown. It can be frightening to muster the courage to step into a new field of possibility.

This inner friction is what Stephen Pressfield calls “the resistance.” It’s the scared part of us who wants to let go but just can’t.

Identifying this, and moving on, just might make all the difference in 2024.

Maybe we should give it a try?

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