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Leadership Lessons From the Bottom: A Freelancer's Perspective

Topics relating to managing people and relationships

Chx

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It was a tough decision. Starting out as a freelancer, rather than going straight into a scalable business. It went against much of the advice here — bypassing CENTS for my first venture.

I dream of being a leader. A visionary. Shaping the world through business, taking care of my employees, and setting myself free in the process.

So why on earth have I been freelance copywriting for two years?

One of the main reasons — I needed to see how a real company operates and how real leaders lead. I'm a 17-year-old guy, and the extent of my work experience is "odd jobs": math tutoring, cleaning up a horse barn (yuck), etc.... AKA, I've never had a real, sustained job.

So I envisioned that freelancing would teach me about leadership and operations... from the worker's perspective.

And teach me it did. During my freelancing career, I've learned a lot about good leadership, bad leadership, and everything in between.

Lesson 1: The Best 'Language' for Leaders to Speak (hint: it's not English...)

As a leader, it doesn't matter if you speak English, French, or Chinese...

Because if you aren't speaking this language, you're losing. Losing your employees' trust. Losing their enthusiasm. Loosing their best work.

The language: appreciation.

Speak appreciation into your employees' lives. If you don't, they will do sh*t work, leave, or both.

Consider two scenarios. Both based on my real experiences.

Scenario A

You need a 10-email sales sequence.

And you need it fast. 3 days.

So you call me, your freelance copywriter, to get it done.

We get on the phone. You brief me on the project, your sales objectives, and some basic guidelines for the copy.

The 3-day deadline makes my heart jump, but whatever. I like this company, I like what they do and the value they provide, and hey, writing a sequence in three days is exciting. So I agree.

Day 1 is research. I dive into your product. I search for reviews online. I look at your past copy and how it performed. All the while, I am brainstorming email ideas. I come up with a funny idea for email 2, a value-packed email for number 6, a great way to create urgency towards the end, and so on...

Day 2 is drafting. I turn on my pomodoro timer, planning on working in 25 minute intervals with 5 minute rest. But once I start writing, my plan goes out the window. I don't need to take any breaks; the words are effortlessly flowing onto the screen. By the end of the day I have done it. I have ten emails.

Day 3 is editing. I check for clarity. I fix tone and voice. I add emotionally charged phrases. I agitate problems, emphasize solutions, and make little tweaks so that the emails work together.

I finally reach a point where I am done. I create a short write-up about my thought processes, and paste it at the top of my Google Doc. Then I put the Google Doc link in Slack and tell you it is done.

At this point, I feel kind of burnt out.

But then you give me a thumbs up in the Slack chat.

Then you say, "Thanks Chx! Looks good so far, loving your work. Will take a closer look sometime tomorrow morning."

Two days later I get an email from your marketing coordinator, at the bottom of which he mentions how highly you spoke of my emails.

And later you call me, and tell me how much you appreciated the quickness and quality of work. You tell me your favorite parts of the sequence. You also have some constructive feedback: tighten up the narrative details in some of the first few emails.

Eventually you tell me how the emails performed double your expectations, and headlines were especially strong.

(Notice how all of this only took you 15, 20 minutes?)

Any burnout I had before was now gone.

After hearing your appreciation, I am rejuvenated and ready for more work. Even ready to do 10 emails in 3 days if need be. I think, I love this work, I love my client, I love what I do. (Then I remember I'm still a freelancer trading time for money, but let's ignore that for now...)

Scenario B

You need a 10-email sales sequence. You need it in 3 days. You hand the project off to me. I agree.

For three days I write the best copy I can muster and make it as strong as I can.

I wrap the assignment up into a Google Doc.

I send the link into your Slack. My three days' work, in one link.

And I wait for a response.

...

...

...

...

...

Radio silence.

No thumbs-up, no thank-you, no ecstatic marketing guy, nothing.

No appreciation. I work my a$$ off for three days and all I get is the abyss staring back at me.

Seven days later, you call me again. This douchebag again? I think.

You mumble something about the old sequence (which I've forgotten about by now) and then you propose a new project. A sales page.

I need the money and the experience, so I agree.

But this time, I don't give my 100% effort. Not even 80%. All my enthusiasm is gone. I have no reason to go above and beyond like I did last time. So I sh*t out some mediocre-effort copy and get it to you before the deadline.

Of course, you're none the wiser. I'm the expert copywriter, not you. That's why you hired me. But your sales take a hit, and some simple appreciation could have averted it.

When earned, speak sincere appreciation into your employees' lives.

It's a simple time investment that will maintain the enthusiasm, morale, and effort of the people working for you.

Before I wrap up this lesson, let me go over two ways to screw appreciation up:

1. Dishonest appreciation. If you give me an eight-paragraph thank-you when I tell you about a simple edit I made to an old sales page, I know you're bullsh*tting and I won't believe any other appreciation you give.

2. Passive aggressive appreciation. I ask you to increase my retainer fee. You say, "Not possible. Sorry. I appreciate you being flexible with a lower fee at this time." Who said I was being flexible? You can't use appreciation to mask a confrontational situation. Just be honest.

You want me to believe you. You want me to believe in you. You want me to follow you to hell and back. You want me to know we're on the same team.

And appreciation can be uncomfortable, especially if you don't actually appreciate your employees. (In that case, you have bigger problems)

But still make an effort. Learn the language of appreciation — your team and business will thank you. No pun intended.

If this thread is well received, I will post Lesson 2: The "Post-It Note Monster" Method that Makes Employees Respect You (and not Resent You)
 
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ZF Lee

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Jul 27, 2016
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It was a tough decision. Starting out as a freelancer, rather than going straight into a scalable business. It went against much of the advice here — bypassing CENTS for my first venture.

I dream of being a leader. A visionary. Shaping the world through business, taking care of my employees, and setting myself free in the process.

So why on earth have I been freelance copywriting for two years?

One of the main reasons — I needed to see how a real company operates and how real leaders lead. I'm a 17-year-old guy, and the extent of my work experience is "odd jobs": math tutoring, cleaning up a horse barn (yuck), etc.... AKA, I've never had a real, sustained job.

So I envisioned that freelancing would teach me about leadership and operations... from the worker's perspective.

And teach me it did. During my freelancing career, I've learned a lot about good leadership, bad leadership, and everything in between.

Lesson 1: The Best 'Language' for Leaders to Speak (hint: it's not English...)

As a leader, it doesn't matter if you speak English, French, or Chinese...

Because if you aren't speaking this language, you're losing. Losing your employees' trust. Losing their enthusiasm. Loosing their best work.

The language: appreciation.

Speak appreciation into your employees' lives. If you don't, they will do sh*t work, leave, or both.

Consider two scenarios. Both based on my real experiences.

Scenario A

You need a 10-email sales sequence.

And you need it fast. 3 days.

So you call me, your freelance copywriter, to get it done.

We get on the phone. You brief me on the project, your sales objectives, and some basic guidelines for the copy.

The 3-day deadline makes my heart jump, but whatever. I like this company, I like what they do and the value they provide, and hey, writing a sequence in three days is exciting. So I agree.

Day 1 is research. I dive into your product. I search for reviews online. I look at your past copy and how it performed. All the while, I am brainstorming email ideas. I come up with a funny idea for email 2, a value-packed email for number 6, a great way to create urgency towards the end, and so on...

Day 2 is drafting. I turn on my pomodoro timer, planning on working in 25 minute intervals with 5 minute rest. But once I start writing, my plan goes out the window. I don't need to take any breaks; the words are effortlessly flowing onto the screen. By the end of the day I have done it. I have ten emails.

Day 3 is editing. I check for clarity. I fix tone and voice. I add emotionally charged phrases. I agitate problems, emphasize solutions, and make little tweaks so that the emails work together.

I finally reach a point where I am done. I create a short write-up about my thought processes, and paste it at the top of my Google Doc. Then I put the Google Doc link in Slack and tell you it is done.

At this point, I feel kind of burnt out.

But then you give me a thumbs up in the Slack chat.

Then you say, "Thanks Chx! Looks good so far, loving your work. Will take a closer look sometime tomorrow morning."

Two days later I get an email from your marketing coordinator, at the bottom of which he mentions how highly you spoke of my emails.

And later you call me, and tell me how much you appreciated the quickness and quality of work. You tell me your favorite parts of the sequence. You also have some constructive feedback: tighten up the narrative details in some of the first few emails.

Eventually you tell me how the emails performed double your expectations, and headlines were especially strong.

(Notice how all of this only took you 15, 20 minutes?)

Any burnout I had before was now gone.

After hearing your appreciation, I am rejuvenated and ready for more work. Even ready to do 10 emails in 3 days if need be. I think, I love this work, I love my client, I love what I do. (Then I remember I'm still a freelancer trading time for money, but let's ignore that for now...)

Scenario B

You need a 10-email sales sequence. You need it in 3 days. You hand the project off to me. I agree.

For three days I write the best copy I can muster and make it as strong as I can.

I wrap the assignment up into a Google Doc.

I send the link into your Slack. My three days' work, in one link.

And I wait for a response.

...

...

...

...

...

Radio silence.

No thumbs-up, no thank-you, no ecstatic marketing guy, nothing.

No appreciation. I work my a$$ off for three days and all I get is the abyss staring back at me.

Seven days later, you call me again. This douchebag again? I think.

You mumble something about the old sequence (which I've forgotten about by now) and then you propose a new project. A sales page.

I need the money and the experience, so I agree.

But this time, I don't give my 100% effort. Not even 80%. All my enthusiasm is gone. I have no reason to go above and beyond like I did last time. So I sh*t out some mediocre-effort copy and get it to you before the deadline.

Of course, you're none the wiser. I'm the expert copywriter, not you. That's why you hired me. But your sales take a hit, and some simple appreciation could have averted it.

When earned, speak sincere appreciation into your employees' lives.

It's a simple time investment that will maintain the enthusiasm, morale, and effort of the people working for you.

Before I wrap up this lesson, let me go over two ways to screw appreciation up:

1. Dishonest appreciation. If you give me an eight-paragraph thank-you when I tell you about a simple edit I made to an old sales page, I know you're bullsh*tting and I won't believe any other appreciation you give.

2. Passive aggressive appreciation. I ask you to increase my retainer fee. You say, "Not possible. Sorry. I appreciate you being flexible with a lower fee at this time." Who said I was being flexible? You can't use appreciation to mask a confrontational situation. Just be honest.

You want me to believe you. You want me to believe in you. You want me to follow you to hell and back. You want me to know we're on the same team.

And appreciation can be uncomfortable, especially if you don't actually appreciate your employees. (In that case, you have bigger problems)

But still make an effort. Learn the language of appreciation — your team and business will thank you. No pun intended.

If this thread is well received, I will post Lesson 2: The "Post-It Note Monster" Method that Makes Employees Respect You (and not Resent You)
Great thread topic!
I was wondering if I should post something like this, after doing freelance copywriting for a fair bit of time.
You beat me to it haha.

Yup, sincere appreciation helps...as long as you continue updating your work processes to make your employees/freelancers/ lives easier.

Otherwise, they'll begin to wonder if you really mean well for them, or you are just talking fluff.
(Another case of 'dishonest appreciation')

Example?

A recent client I fired early this month was very appreciative of my work many times. Talked about how I actually responded to calls and updated him faster than many of his full-time staff (be specific on WHAT the employee did right). Still keeps some of my sales copy taglines on his FB ads and various other emails.

However, revision requests continued to be F*cking disorganized, continued giving feedback that actually made deliverables out-of-whack, and I found myself working all day, around the clock beyond reasonable.

The compliments did give me the emotional boost, even in stressful times...but at the end of the day, I returned to rationality and started worrying about the actual workflow.

When I tried to discuss better terms or even book a 5-min call, he'd say something like 'Yeah, but I'm busy. Can I follow up tomorrow?' and then he never did. And I'd have to chase him like a fox with a sheep...

Also, do your best to not outsource personal leadership.

You can delegate some stuffs to managers or department heads, but leaders, at some points, should find time to speak to the employees themselves.

Better face-to-face. Cut down the memos. And make it regular-like even a few times a week or every day, depending on your culture and nature of your business.

That client I mentioned started having his assistant do 90% of the leading, and there were times I couldn't get a peep from the WhatsApp from him, even though he was the one who hired and directed me at first. That was a death-flag.
 

Chx

Bronze Contributor
FASTLANE INSIDER
Read Fastlane!
Read Unscripted!
Speedway Pass
User Power
Value/Post Ratio
308%
Feb 6, 2018
109
336
United States
Great thread topic!
I was wondering if I should post something like this, after doing freelance copywriting for a fair bit of time.
You beat me to it haha.

Yup, sincere appreciation helps...as long as you continue updating your work processes to make your employees/freelancers/ lives easier.

Otherwise, they'll begin to wonder if you really mean well for them, or you are just talking fluff.
(Another case of 'dishonest appreciation')

Example?

A recent client I fired early this month was very appreciative of my work many times. Talked about how I actually responded to calls and updated him faster than many of his full-time staff (be specific on WHAT the employee did right). Still keeps some of my sales copy taglines on his FB ads and various other emails.

However, revision requests continued to be F*cking disorganized, continued giving feedback that actually made deliverables out-of-whack, and I found myself working all day, around the clock beyond reasonable.

The compliments did give me the emotional boost, even in stressful times...but at the end of the day, I returned to rationality and started worrying about the actual workflow.

When I tried to discuss better terms or even book a 5-min call, he'd say something like 'Yeah, but I'm busy. Can I follow up tomorrow?' and then he never did. And I'd have to chase him like a fox with a sheep...

Also, do your best to not outsource personal leadership.

You can delegate some stuffs to managers or department heads, but leaders, at some points, should find time to speak to the employees themselves.

Better face-to-face. Cut down the memos. And make it regular-like even a few times a week or every day, depending on your culture and nature of your business.

That client I mentioned started having his assistant do 90% of the leading, and there were times I couldn't get a peep from the WhatsApp from him, even though he was the one who hired and directed me at first. That was a death-flag.

100% agree on your first point. For me it comes down to whether you're working into an abyss or not. Are your efforts and troubles being recognized and addressed? If not, there's a problem.

On your second point, about outsourcing personal leadership, it depends on the size of the business and the CEO's obligations.

One of my clients is a big-name podcaster in the self-improvement space. I've been working with his company for three months, but I hadn't even met the guy until yesterday. But it makes sense for him. If he spends his time recording episodes and networking with future guests, his time is worth $1000s per hour. If he spends his time talking to me, that figure plummets. Which is why he hires a COO, marketing director, etc. to communicate with me.

(Though, it was very gratifying to finally get to chat with him.)

And for those of us who want to eventually detach ourselves from the business, I'd say getting managers is an essential step.

But if you have 3 employees and you refuse to talk to them, that's an issue.
 

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