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Why Smart People Are Terrible at Business

How a simple google search challenged everything I learned in business school at Stanford

Photo by Joshua Hoehne on Unsplash

In 2014, I was a bright-eyed newly untested entrepreneur.

I had a dream.

It wasn’t as profound as Martin Luther King Jr’s dream but it was a dream, nonetheless. What made it special is that it was mine.

I had a dream of starting my own business.

Unplugging from the corporate cubicle nation.

Reporting to no one but myself.

So I quit my job but got a soft landing. I hedged my bet and went to one of the best business schools in the world. Stanford GSBoomshakalaka!!! I went all in, coasting on the Silicon Valley dream. I could have focused my time plugging into the business models there but no, I had a dream.

A dream of going back home, and industrializing Africa.

In 2016, I moved back to Nigeria.

I started off my business as a resource for entrepreneurs to share valuable information with one another.

Within three months, I realized no one was willing to pay for that. After discussions with multiple people I got the response: “it’s nice to have but…errmmm…would I really use it?”

My dream started fidgeting before me like a faulty daffy duck toy.

All those Entrepreneur and Fast Company magazines filled with success stories of companies that started post-financial crisis in 2008 that got me on this path had receded to the faintest part of my memory.

I went from “I have a dream” to “it was all a dream, I used to read entrepreneur magazine. Dangote and Richard Branson on the TV screen.”

I was confronted with reality.

I pivoted. Then pivoted. Then pivoted once again.

Until I landed my first client.

It was an automotive paint company that needed local distributors in Africa’s largest population.

The client said: “Let’s get started, Nifemi. Send us an invoice.”

I said “Definitely, you’ll get it in your inbox soon.” Then hung up and Googled: “How do you create an invoice.”

For a business school student from Stanford, you’d think “Come on, you must know how to create an invoice.”

But I didn’t.

And there was a big humbling lesson there.

Why business education gets it backwards

Most people want to figure it all out in their minds before starting.

Consuming endless info.
Reciting stories with friends.
Practicing pitches about the future.

With each step, we delude ourselves.

Most books, classrooms, and content online is filled with success stories.

They give you a snapshot of what worked for a company, and a team, in a certain market, at a particular time.

When we read, listen, and watch, we begin to recite the tried-and-tested playbook for success. MBAs in curated classes, learning from academic professors who haven’t been humbled by crushing reality of market friction and failure, draw strategic lines through constructed case studies, with the hopes that pattern recognition becomes apparent through repetition.

Although pattern recognition is invaluable, and when you can connect the dots, it’s all great.

However, here’s what they don’t teach in school:

What to do when the pattern doesn’t make sense.

How to calibrate your internal state, as a builder, when clarity crumbles into chaos.

It’s easy to tell a success story looking backwards.
It’s hard to predict success looking forward.

The reality is that you don’t know what you don’t know until you start.

No one told me that a multi-billion corporation (my client) would sign a 90-day payment term with me (the vendor), and I’d have to fight through hoops and complex procurement processes to receive that payment.

Nah. I didn’t see that in any business case study.

In fact, I had no clue what payment terms were until I signed my first deal. I was just an engineer that could build stuff.

I didn’t realize what currency risk was until I had international clients.

I didn’t realize some of the best businesses in emerging markets didn’t have an online presence until I had to drive around to their office to meet and verify in-person. That in itself was an opportunity that I bridged.

I had no clue I had to send out close to a thousand emails to get on 38 calls to get to 14 proposals, just to close one deal.

ONE Deal!!!

That I only got paid for 90 days after delivering a 3-month long project. That’s a whole half-year from signing the contract to payment. (Sorry I’m still traumatized)

But now I’ve learned.

I have templates for my invoices.
I negotiate payment terms before signing.
I know the effective channels to reach customers.

This evolution did not come from reading. It came from doing and learning along the way.

Pattern recognition from case studies is useless without coping skills for when patterns break.

That’s why for anything you want to learn well, you need to start it as a project.

The value of learning through mini-projects

Starting a project is easy.

Finishing one is hard.

I was working with a client recently. In one of our sessions, I mentioned how she could make her content more organic by just focusing on the problems her target audience faced.

She said: “Oh wow, that’s a lightbulb moment. That makes it a lot easier.”

Now, I didn’t realize that could shift someone’s thinking because I thought most people knew that. This is the other side of what you learn from experience. However, my client is filling her knowledge gap because she has committed to a 3-week project to build her organic brand for her business.

Projects require commitment.
Projects force you to clarify your intention.
Projects put guardrails on your attention.

Here’s what I’m noticing on the practice ground of building: most people get excited about starting something but don’t know how to push through when they hit the project plateau – the den filled with dead unrealized ideas.

When you start a project, you are enthusiastic on day 1.

Perhaps you still have some excitement by the end of the week. But then week 2 comes, that excitement fades. Week 3 – things are not working out. This is when it becomes easy to fall for the distraction trap of a “brand new idea.”

The biggest threat to an idea is a brand new idea.

Why?

Because your body and mind seeks a dopamine hit and immediate gratification.

The people that make it through the project plateau only get there with persistence.

Here’s what works: do shorter project sprints.

You want to write a 12-chapter book by the end of next year?
Do a one-chapter by the end of the month.

You want to create your next one-hour DJ set.
Start with a 6-minute DJ set.

You want to write a weekly essay?
Write a daily subsection.

Overcoming the need for immediate gratification requires a good amount of mental rewiring but you can begin the practice by shortening the gratification loop.

Ask yourself: “What do I want to learn in the next year?”

Let’s make that more concrete: “What do I want to learn by December 2026 that would make me extremely proud of myself?”

Then ask, “What project can I do to help me learn that?”

Then ask yourself, “What mini-version of that project can I do before the end of this year?”

You will learn when you can follow through on a project.

Make it approachable.

Instead of taking on more than you can chew, start with something you can complete.

Final thoughts:

There’s no perfect playbook for you.

You just have to start. However, you can minimize your risk by taking little bets in the form of short project sprints to learn along the way as you build momentum.

Keep practicing,
Nifemi

P.S. Speaking of mini-projects – I’m putting together something this week to help a small group get clarity and accountability on their next learning project. It’s designed around the principles I just shared about beating the project plateau.

If you’d rather not hear about it, click here to opt out of just the project-related emails (you’ll still get the weekly newsletter).

Who is Nifemi?

Hey I’m Nifemi of NapoRepublic

I help busy people fit in a creative practice to bring to bring order to their reality and help them live a more meaningful life through writing and reflection.

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