The worst mistake freelancers make

It’s Thursday and today there is just one call on my calendar.

I’m talking to a guy I’ve messaged with sporadically in the past. 

But, in some ways, I feel I know him very, very well. 

Here’s what I know…

He’s a copywriter. 

And he’s pretty good at it. 

Good enough to land two big retainer gigs last year and keep them.

Until they both ended suddenly last month. 

Leaving him with no revenue.

And a baby on the way. 

I know that he’s clever, charismatic, and follows advice well. 

In fact, I interviewed the guy who hired him for one of those gigs. 

He was blown away at how this guy showed up so differently than the rest of the copywriters who applied for the job he posted in Copy Chief. 

He said, “I forwarded his cover letter to the CEO and he replied, ‘Hire this guy immediately!’.”

I also know that this copywriter is scared. 

He committed one of the most common mistakes freelancers make, and it came back to bite him at the worst possible time. 

In the comfort of getting paid to promote other people’s businesses, he gave up on promoting his own. 

Now, there are no leads. 

Very little network. 

Too few former clients to reach out to about doing new work. 

So, he’s stuck on an island. 

He knows there is safe land just beyond the horizon, but with time ticking, and limited funds, he needs to choose the perfect path to getting himself there.

He’s got one shot to get it right.

There are traditional paths, UpWork, LinkedIn, etc. But those are bridges he’d need to build while he walks them. 

Slow, unsteady, subject to change at any given moment.

One storm and you’re screwed. 

Vulnerable to the elements. 

Wishing you were back on the island under your palm frond hut. 

That’s not going to work. 

What he needs is someone with a boat.

He contacted me because he knows I have a boat. 

A big, shiny boat with a powerful motor. 

And, I know exactly where he’s located. 

I’m happy to come get him. 

Ride him to safe land in luxury.

This boat though, it’s expensive to run. 

It’s not a government boat. 

It’s private.

It cost ten years and over a million dollars to build this boat. 

And while it’d be nice to drive around rescuing people all day as a charity, this would cause the boat to fall apart.

Very quickly.

We’ve all seen those boats in the form of free groups. 

Nice for a minute. 

Broken before you know it. 

Then gone. 

So, this copywriter, he feels strongly that agreeing to have me come get him is the smartest choice. 

And, of course, I know this to be true. 

We’ve discussed the fee and he can afford it. 

But, he’s still scared. 

Understandably so. 

Because when you’re stuck on an island, with limited resources, and a new child arriving soon, survival instinct tells you to hoard what you’ve got.

And hope things get better. 

I’ve been on that island, and I have felt that instinct. 

It’s a strong one. 

But, then there’s a new instinct. 

One that every entrepreneur feels – and remembers feeling – for the first time. 

An instinct to double down.

To not hoard.

To not turn and run. 

To not feel scared anymore. 

It’s a strange and powerful feeling. 

It shocked me when I felt it. 

I remember the exact moment and where I was standing when it happened. 

But the thing I’ll never forget is the way it felt to finally believe in myself.

Everyone else that mattered already believed in me. 

My wife, my peers, my friends, most family, 

The only doubt I had was internal. 

I trusted the person with the boat. 

I trusted the boat. 

I had seen the treasures waiting on land. 

But, until that moment, I did not believe that I had what it took to get there. 

You see, outside conditions can always change, but inside your head the truth remains. 

And you’re the only one who truly hears it. 

The voices of doubt. 

Instilled in ways we can’t always identify. 

They ring louder than even the most encouraging words. 

Ruthless bullies. 

They’ll rule your life, until you choose to fight. 

That feeling, when you finally decide to fight back. 

To double down. 

To run towards the future, instead of being ruled by your past. 

It changes everything. 

Forever.

One call. 

We’ll see what happens.