The Shift: From Specialist to Generalist to Specialist Again

_{[Read time: 3.5 minutes]}

When I first left my job to start my own business, I thought I was ready.

I had spent years honing my craft, building the critical thinking skills that made me an expert in strategy and finance.

My confidence was high.

But after a year of running my business, I felt like I had been thrown into the deep end of the ocean — without a life jacket.

(At the time I would have told you everything was going swimmingly, but honestly I was lucky to stay afloat at that point)

The Specialist Trap

In my corporate-like role at Harvard, I was a specialist. My expertise was clear, and my responsibilities fit neatly into my job description.

I excelled at zooming into problems, analyzing data, and finding solutions within the boundaries of my role. But those boundaries also gave me structure. They protected me.

When I started my business, that protective shield disappeared.

Suddenly, I wasn’t just solving strategic problems; I was the one selling the solutions, marketing them, pricing them, and delivering them.

It wasn’t my work that was the issue — it was my approach.

I was operating as if I were still a cog in a well-oiled machine, not the person building the machine.

Learning to Be a Generalist

This misstep forced me to face an uncomfortable truth: my expertise alone wasn’t enough.

Running a business meant learning how to wear every hat.

(which I enjoyed and wanted, but was naive to believe I was any good)

I had to figure out:

• Sales: How do I convince people to trust me with their money?

• Marketing: How do I stand out?

• Operations: How do I deliver great work without burning out?

• Finance: How do I manage money in a business setting, not a corporate one?

• Strategy: How do I re-apply principles and frameworks to a new landscape?

It felt overwhelming.

I spent months deep in learning mode, reading everything I could about sales funnels, pricing strategies, and marketing copy. I tried, failed, and tried again.

And still occasionally fail.

Slowly, I started connecting the dots between all the moving parts of a business.

I wasn’t just learning; I was unlearning, too. I had to let go of the idea that I could lean on my specialist skills and be “good enough.”

To survive, I had to become a generalist to my business.

Returning to Specialist — But in a New Way

Here’s the twist: once I started making progress as a generalist, I had to re-learn how to specialize.

Why? Because while you run your business as a generalist, your customers don’t want a generalist.

They want a specialist.

I always struggled with the question “What exactly do you do?”

Instead of giving a clear answer, I rattled off all some complex monologue of ways I could help: strategy, finance, operations, you name it.

People would nod politely — but my answer never landed well.

That’s when it hit me. People don’t hire you for everything you can do. They hire you for the one thing you can help them with (and hopefully its something you’re exceptional at).

So I changed my approach.

Instead of presenting myself as a jack-of-all-trades consultant to solve all business-related problems, I focused on one thing: helping business owners find hidden profit in their businesses.

That’s it.

I’ve since narrowed that even further to work with small service-based businesses (less than 5 people) and ways to further support them (like business coaching).

It’s worked.

But there’s still more work to be done.

The Cycle of Growth

Here’s what I learned from the experience:

As an employee, you start as a specialist. As a business owner, you transform into a generalist to run the business all while having specializing again — but this time, for your customers.

It’s not a linear journey. It’s a cycle of growth, one that forces you to expand, refine, and focus at every step.

When you nail both identities — generalist for your business, specialist for your customers — that’s when you see some momentum.

Thank you for reading.

See you next week.

— Peter