The Barber Career I Wish Existed When I Started

Why I believe the future of barbering needs more craftsmanship, more structure, and a clearer path to ownership.

I have been cutting hair for more than 16 years, and one of the things I have become increasingly convinced of is that barbering has started to confuse art with craft.

There is nothing wrong with artistry. Individuality is important. Creativity is important. Personal style is important.

But barbering, at its core, is a craft.

Craft requires repetition. It requires constant improvement. It requires doing the same fundamental things thousands of times and continuing to look for the small ways they can be done better.

There is no shortcut to that.

You cannot manufacture mastery through branding, social media, a great portfolio, or opening a shop.

It compounds over time.

And I think we have started to lose touch with that.

The client isn't looking for an artist

A lot of modern barber culture is built around independence and artistic expression.

Those things can be great for the barber.

But I think we sometimes forget to ask what the client actually needs.

Most people walking into a barbershop (barber shop) aren't looking to become part of someone's artistic experiment. They have a job. A family. A meeting next week. A wedding. A date. A normal life.

They want to look good within that life.

The salon industry has always had a place for extreme artistic work. There are runway shows, beauty shows, editorial shoots, tours and film sets where someone might create a hairstyle that is intentionally dramatic or impractical.

That is a legitimate career.

But it is different from standing behind a chair and taking care of somebody every four weeks.

The person sitting in your chair needs a craftsman.

Someone who can listen, assess, make a recommendation and consistently execute.

That distinction matters to me.

At a certain point, the haircut isn't enough

Technical skill obviously matters. It is the admission price.

But there eventually comes a point where your fade cannot become infinitely cleaner. Your photography cannot become infinitely better. Your models cannot become infinitely better looking.

If everyone at the top has excellent technical ability, something else has to separate them.

I learned early in my career that the answer was hospitality.

The haircut might be why somebody finds you.

Hospitality is often why they return.

It is remembering what you talked about at their last appointment. It is noticing when something about their hair has changed. It is understanding when somebody wants conversation and when they would rather sit quietly.

It is care.

That is why I think the best barbers become something closer to what I would call Masters of Coolness.

A great barber should be so comfortable with who they are that they don’t need to imitate each other.

Your taste, interests, style, music, perspective and life experience should make you more distinctly yourself.

Clients are attracted to that confidence. In some ways, they are choosing a barber because they want a small piece of that person's point of view.

But individuality sits on top of the craft.

It cannot replace it.

A consultation should actually mean something

One place where this philosophy becomes practical is the consultation.

A consultation is not simply standing behind somebody and asking, "What are we doing today?"

To me, it is closer to an assessment.

You ask questions.

What happened with the last haircut?

What did you like?

What didn't you like?

How do you actually style your hair?

How often are you willing to maintain this?

What happens when it grows out?

Then barber and client collaborate on an outcome.

That takes more thought than simply knowing how to perform a haircut.

It requires understanding people.

That is the kind of barber we are trying to develop at Oliver Club.

I don't think young barbers lack ambition

Hiring while trying to grow a small business has forced me to think about this more than I expected.

When it becomes difficult to find the right people, it is easy to start believing they no longer exist.

I don't believe that.

I know they exist because I was one of them.

Unless I somehow had a once-in-a-generation level of motivation, there are young barbers out there right now who are willing to work hard, accumulate repetitions, learn the business and become exceptional at what they do.

Our responsibility is not to complain that we cannot find them.

Our responsibility is to build something they can recognize themselves in and make sure they can find us.

That means being clear about what we value.

Drive matters to me.

We initially placed a tremendous amount of emphasis on personality when thinking about hiring. Personality still matters. Hospitality depends on it.

But personality without drive isn't enough.

There are people in every industry who want the rewards associated with being successful more than they want the process required to become successful.

Barbering does not work particularly well that way.

This has traditionally been a humble profession.

You stand behind the chair.

The client sits in it.

There is a famous type of photograph we have all seen: a celebrity sitting in a barber chair with a barber working behind them.

Nobody remembers the photograph because of the barber.

The client is the star.

That doesn't diminish the barber. I think there is something honorable about it.

Your job is to use your ability to make somebody else feel good.

Real ambition in this profession has to coexist with that humility.

I spent a long time not being successful

I worked six days a week, open to close, early in my career.

I accumulated repetitions.

Then I accumulated more.

There were periods when the rational decision probably would have been to quit.

I didn't.

That experience is part of what eventually allowed me to build businesses and understand the patterns behind a barber's career: client retention, booking behavior, acquisition, seasonality, pricing, marketing, service consistency and the dozens of other things that determine whether someone actually develops a sustainable clientele.

None of those things are taught when you learn how to perform a fade.

Historically, a barber often learned them through trial and error.

You worked for years. You built your book. You made mistakes. You saved money. Maybe after ten years or more behind the chair, you finally had enough experience and resources to open your own shop.

I understand that path because I lived a version of it.

But I don't believe every generation needs to repeat every hardship of the generation before it.

The repetitions cannot be skipped.

The craft cannot be skipped.

But some of the uncertainty can.

Building the system I wish I had

That idea influences almost everything we are building at the Oliver Club Barber Shop.

I don't want a talented young barber who genuinely loves this profession to have to repeatedly decide whether they can afford to stay in it.

Our compensation structure was built from a simple question:

What would I have wanted when I was becoming a barber?

I wanted the opportunity to earn more as I became more productive.

But I also could have used stability while I was building.

Traditional barber compensation can put nearly all of the early risk on the barber. If the shop is slow, the barber is slow. If there aren't enough clients yet, the barber absorbs that uncertainty.

We are trying to build a different structure around that period of development.

The company should provide consistency, infrastructure, a professional environment, systems, marketing knowledge and a clean place to do excellent work.

The barber has responsibilities too.

Commitment.

Professionalism.

Consistency.

Development.

And being there for the client.

It has to work in both directions.

A barber should learn the business of being a barber

Technique is only part of what an ambitious young barber should leave Oliver Club knowing.

They should understand why clients return.

They should understand booking patterns.

They should know what a slow season looks like before it arrives.

They should understand acquisition costs, marketing, pricing and how a clientele develops over time.

They should know the difference between being busy because the shop gave them traffic and being busy because they have built demand for themselves.

These are lessons I accumulated through years of observation and trial and error.

A system allows us to teach them intentionally.

That does not remove the work.

It removes some of the unnecessary guessing.

I learned this philosophy at a coffee stand

Strangely, one of the experiences that influenced how I think about this happened before I ever became a barber.

My first job was at a small drive-through coffee company called The Daily Grind.

I was a freshman in high school.

Looking back, it seems unusual that they hired someone that young. Then I realized most of the group hired around the same time were freshmen too.

The company had a progression system.

You started as a junior barista.

After enough time and training, you could test to become a senior barista.

Then there was master barista.

Then manager.

Each level meant more responsibility and higher pay.

Some employees were perfectly comfortable remaining where they were.

I wasn't.

I took the tests.

What I didn't fully understand at the time was how intelligent the system was.

Hire someone as a freshman and they potentially stay with you throughout high school. Each year gives them another level to work toward.

By senior year, that teenager could potentially have management experience.

Then they leave for college and apply for another job with "manager" or "master barista" on their résumé while most people their age are applying with very little experience at all.

That business became successful in part by making its employees more successful.

I learned more about entrepreneurship from that first job than I understood at the time.

And that idea has stayed with me.

Employment should compound

I want Oliver Club to work similarly.

If somebody joins us at 22 and stays until 30, I don't want them to simply become an employee who has worked at Oliver Club for eight years.

Eight years should mean something.

Their technical ability should be dramatically better.

Their clientele should be stronger.

Their understanding of business should be deeper.

Their judgment should be better.

They should know how to lead people.

They should know how to develop the next barber coming behind them.

And eventually, I think the conversation should become about ownership.

My long-term goal is for members of our core team to have the opportunity to operate Oliver Club shops in which they have an ownership stake.

The exact structure may vary. It could mean a minority position, an equal partnership or another arrangement that makes sense at the time.

But the principle matters more than the percentage.

If somebody spends the better part of a decade helping create value in this company, becoming exceptional at their craft and developing into a leader, there should be somewhere meaningful for them to go.

Another raise cannot be the only answer forever.

Ownership should be the result of development

I am not against young people owning businesses.

I am a small-business owner. Entrepreneurship changed my life.

But access to capital and access to mastery are two different things.

Capital can accelerate ownership.

It cannot accelerate craft.

Traditionally, opening a barbershop often came after years behind the chair because those years were how a barber accumulated not only money, but judgment.

Today, somebody may have access to resources that allow them to become an owner considerably faster.

There is nothing inherently wrong with that.

But owning something and mastering something are not the same achievement.

What interests me is building a path where ownership becomes the natural result of development.

Learn the craft.

Develop the clientele.

Understand the economics.

Learn to lead.

Help build the business.

Then own part of what you helped create.

The future can still respect the past

I don't think changing barbering means rejecting its traditions.

I think it means understanding which traditions were valuable and which hardships were simply consequences of an industry that lacked better systems.

The humility is worth preserving.

The commitment to service is worth preserving.

The repetitions are absolutely worth preserving.

The idea that mastery takes years is worth preserving.

But instability does not need to be romanticized.

Lack of mentorship does not make somebody tougher.

Having no idea how to build a clientele is not a rite of passage.

And ownership does not need to be the only way for a talented barber to see a future for themselves.

I am trying to build the team I wish I could have joined when I was younger.

A place where individuality is encouraged, but craftsmanship is expected.

Where hospitality matters as much as technical ability.

Where ambition is welcomed, but service comes first.

Where the business accepts responsibility for developing its people, and its people accept responsibility for doing the work.

And where someone who gives years of their career to helping build the company has a path toward owning part of its future.

I spent more than 16 years learning how difficult this career can be when you have to figure everything out yourself.

The next generation will still have to put in the repetitions.

They will still have to earn mastery.

But they shouldn't have to guess where the road leads.