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The Unlikely Job that Made Me a Master Freelancer

You learn skills from the unlikeliest of places sometimes.

I said I would never do it.

That thought rang in my head for two full years as I waited tables at a popular, high-end fondue restaurant while in college.

I didn’t think I would ever wait tables. And yet, there I was: picking up drinks from the bartender, melting cheese at tables, and readjusting the apron around my waist.

But while I spent those years stumbling out of the restaurant at midnight or 1am, limping, hungry, and wishing I was hanging out with my friends on a Friday night…

…those two years set me up for the success that I have had in the 15 years since I put in my notice.

A successful waiter vs. A successful freelancer

I know many people who think that being a waiter is beneath them.

Heck, as you see above, I was one of those people.

But waiting tables is the ultimate “in the fire” job.

Once you get the hang of things, you’re in it.

There isn’t much time to “go easy on you” when it’s Friday night and the bar area is overflowing with patrons who want to be seated.

And if you want to make as much money as possible, you have to take on as many of those tables as you physically can.

Freelancing is the same way.

When bills are piling up, you need to make money.

And that means taking on as many clients as you can.

Too often I hear from beginner freelancers, “How can I make more money without taking on more clients?”

Sure, you can raise your rates.

But the fact is, the fastest and most effective way to do it is by figuring out how to handle more clients.

A waiter can’t say, “I want to make more in tips but take on less tables.”

Any other waiter would say that sounds stupid.

Being a waiter is like being a freelancer.

The job helped me build valuable skills I draw on to this day.

8 Things I Learned from Waiting Tables that Made Me a Successful Freelancer

#1. You need to develop the “soft skills”.

Every freelancer is Googling around to find strategies and tactics that they can use to get clients and get paid.

That’s fine… but there are skills they need to build first.

I chuckle whenever somebody says, “I want to get clients but I don’t want to be on the phone with them.”

To that I say: too bad!

Clients want to know who they are working with. That means you gotta jump on the phone with them from time to time – and that’s where soft skills come into play.

  • Being likable
  • Holding a conversation
  • Connecting with someone emotionally
  • Building a relationship
  • Establishing trust

These are things you have to do as a waiter at every table.

If you are mildly funny, pleasant to be around, and presentable, people will tip you… and they’ll hire you.

#2. You need a dose of humility.

You know what I’m doing after I finish writing this essay?

I’m going to go send out 30-50 DMs to prospective writers.

It’s tedious. It’s time consuming. It feels “beneath” a writer like me that is making such good money.

But I’m doing it anyway.

See, that’s where you and I are different. You see the drudgery and you try to make it more efficient.

I see the drudgery and I dig in and get to work.

Only one of us is going to see results.

As a waiter, you have to deal with lots of tasks that might be beneath you.

You might have to clean up a bathroom, suck up to rich people, wipe down kitchen counters.

It builds character. And it reminds you that hard work is worthwhile.

There’s no “optimizing” that. If you carry that attitude into your freelancing work, guess what happens? You get sh*t done, and you get paid more often.

#3. The customer/client is “always right”.

Note that I put that in quotes.

The customer can be wrong a LOT.

It was common to deal with customers who claimed they ordered something different, even though I know they didn’t.

And what happened when we had that conflict?

I apologized, took the order back to the kitchen, and got the one they wanted.

It didn’t matter if I was right. If I wanted their tip, I had to let them be right.

Freelancing success often comes down to recognizing who signs your paychecks.

#4. The money isn’t yours. It’s theirs.

Related to the last point…

When you collect a paycheck from some retail store or whatever, the money is yours. You earned it, it’s calculated based on the hours you worked, and it is owed to you legally.

In other words, the money just kinda comes out of thin air.

When you wait tables, the money is coming directly out of somebody else’s pocket… and they are not legally obligated to give it to you.

What does that mean?

It means you have to spend every moment with that table making yourself worth it. You deliver value as much as possible.

Too many freelancers act as though they deserve money because they put in time.

But your value is only as much as what you provide the client.

They choose how much to give you.

And to that end…

#5. It doesn’t matter what you “deserve”.

I’ve been telling the story recently of the $4,000 refund I was forced to give one of my clients.

I could have fought him.

I put in half a month’s worth of work. I could have kept half of the monthly retainer.

I deserved it.

Instead, I fought tooth and nail to give him back the full amount.

He was already being difficult and making threats that could have posed a real problem for me.

Sure, I deserved the money. But it didn’t matter in the real world. 

As a waiter, you’re not paid based on the amount of time you spend. Or even the effort, to an extent.

If a customer signs the credit card slip and then takes both slips when they walk out, guess what? No tip for you!

You have to deal with that realization as much as possible.

#6. You have to work under pressure.

When you go to a restaurant, you don’t want to wait around for your food.

So as a waiter, it’s your responsiblity to make sure patrons are getting their meals in a timely fashion.

Now imagine you’re juggling four tables. One table needs their check, one needs their cheese fondue made, one is waiting for a round of drinks from the bar, and one is waiting for their dessert.

Your brain has to keep all of them straight, prioritize them, and knock them out as fast as physically possible.

There is zero time to feel sorry for yourself.

As a freelancer, there is also zero time to feel sorry for yourself.

On an average day, I have to do bookkeeping, analyze and adjust my marketing strategies, serve my writers, reach out to new writers, continue conversations I’ve already started, write copy for other clients…

It gets to be a lot.

But my brain is still honed from waiting tables that I can largely keep track of the important things.

#7. Life – and work – ain’t fair.

My wife did not wait tables in her life.

One thing that mortifies her is when I talk about my shifts, which consisted of:

  • No ability to take off of work unless I could find someone to take my shift (or I was out of luck, even when sick)
  • No place to sit down in the kitchen, so I was routinely on my feet for 8-12 hours
  • No breaks
  • No meals, except for an included salad – though we rarely had time to eat it so it wasn’t ordered that often
  • No bathroom breaks. If nature called, you had to squeeze it in between checking on your tables. Then you hoped to the good Lord himself that you didn’t have to take too long in there

None of that is fair. It almost sounds inhumane to the Internet World.

But it toughened me up.

Freelancing isn’t fair, either. I’ve been screwed out of time and money. I’ve been fired for no reason.

Some days, especially in the past, I’ve had to work deep into the night just to stay on top of things.

Fair doesn’t matter in the real world.

#8. Generally, more hard work = more $$$.

There are exceptions, but as a waiter, if you are working hard, you’re developing your skills.

And if your skills are strong, you’ll get more tips.

It’s that simple.

Freelancing is the same way.

If you work hard, you develop writing and communication skills that help tremendously.

Slack off and you won’t make that moolah.

Now, one of the most frustrating aspects of freelancing is this last one.

I’ve never been one to avoid hard work. But there have been times when I felt like I was bashing my head against a brick wall because I didn’t know WHAT to work on.

How was I supposed to know the best uses of my time? Or what would get me clients faster?

It took me years to crack that code… but I did.

And once I did, my income grew.

I rode the “roller coaster” of income until 2018. That year was the bottom: I only made $18,000.

In 2019, I made $99,000+.

In 2020, $125,000.

In 2021, $209,000.

In 2022, $260,000+.

Because I had the skills I developed as a waiter, combined with a clear framework for getting and keeping clients based on my 15 years as a freelance copywriter, I ripped the ceiling off of my income.

And I want to help you do the same.

As you read this, I’m working with 145+ writers to help them get new clients faster, keep them longer, and get paid more.

Whether you’re a seasoned pro or a wet-behind-the-ears beginner, this is for you.

  • Since I worked with Alan, he’s banked five figures in a matter of months.
  • Sara is now making more than $100,000/year and still gets to stay home and take care of her kids.
  • LB and Trent are booking retainers like crazy.

And they’re not alone.

It’s your turn to be a part of this.

You can get your first clients.

You can land your first retainer paychecks.

You can scale up to $5,000-$10,000/month in income.

I have the tools and resources, and I’ll help you build the skills, too.

Just click HERE and I’ll get you set up.