The Dark Side of Freelancing

By Stephen Godfrey - Reading Time: 8 minutes

vader head shot Source:

We often hear that freelancing is great.

And it is. I love working from home, taking naps after lunch, and having the freedom to set my own schedule.

But there is a dark side to freelancing.

True, once you’ve figured out your niche, have enough clients, and have money coming in then freelancing is great. But what about if you are still learning the craft? What if you are still struggling?

So let’s talk about the darkest side of freelancing. Here is are the five hardest parts about freelancing:

  1. Not having enough money.
  2. Not enough time.
  3. Not staying on task.
  4. Loneliness.
  5. Fear of famine.

1. Not Having Enough Money.

star wars empire money

Not having enough money is hard.

When cash is tight you might be tempted to take any job that you can get. You’ll be tempted to drop your rate so you can land the gig. You might be inclined to put in extra hours just because you need to keep this client.

What a soul sucking idea.

So what is the cause of not having enough money? Usually it’s because your rate is too low. Or it’s because you don’t have enough clients. It could be that you have too many expenses, or that you aren’t saving enough to ride out the slow times (November and Christmas can be hard to find work).

The Fix

So how can you fix this? How can you get more money? Well, to find the answer we need to ask some questions. So ask yourself:

  1. Do you have a system or process to get new leads?
  2. Do you network and connect with other people?
  3. Do you have a skill that people value?
  4. Do you charge enough for your work?
  5. Do you manage your finances well?

If you answered no to any of these then you know where to start. And these items are listed in this order for a reason.

So pick the first no in your list, and work on that. Just find a way.

And soon enough you’ll have enough money.

You won’t have to struggle so much, and it will all be okay. But you need to work at it.

So… hustle.

2. Not enough time.

death star construction

Not having enough time is another vice of freelancing. Sure you might have client work, but that is time spent working on someone else’s idea. Someone else’s dream.

And often, if you are too busy, then you don’t have enough time to look for other clients. And if you only have one client then you are in one of the most dangerous positions of all.

And it’s an easy trap to fall into. Should you make $XXX for a day’s worth of work? Or do you spend time working on your own website? One of them gets you money now, but the other helps get you money tomorrow. And you need to balance both.

The Fix

So how you fix this?

You need to treat your freelancing business like a business. You need to always be thinking about the next client, and how to contact more leads. And if you are already busy working on client projects then have a side hustle–a side hustle of working on YOUR business.

Think about it. Even though you are busy, schedule every other Saturday to work on your website. Soon enough you’ll have the redesign finished. Then you can rework the messaging on your site. And you’ll be able to add a few testimonials. And then add some case studies. And perhaps even setup some facebook ads.

Then that can help you have the confidence to setup some referral systems in place. Or perhaps a method for outreach.

And all of this will help you get new clients. New clients that you can charge a higher rate. And a higher rate means that you can work less, but still bring in the same amount of revenue.

It’s a good place to be in.

3. Too Hard to Stay on Task

star wars death star operators


It can be hard to stay on task. There’s social media, Youtube, emails, texts, and a whole host of other distractions. And this can be deadly for the lone freelancer.

You see, when you work for an employer you have a lot of outside accountability and influence. It’s hard to waste all day watching videos at work when your coworkers can see your screen, and where your boss is walking around.

But what about when you work at home? What if you work remotely? It can be really tempting to waste time when you are just by yourself.

The Fix

First you need to decide what you are going to do in a day. But you need to decide the night before.

Second, enter it in your calendar or just have a todo list on a piece of paper. Either way the trick is to write it down, and to decide when you’ll do it.

For instance, my schedule might be: 8-8:30am Writing. 8:30-9:00 Outreach. 9:00-12:00 client work 12:00-1:00 lunch 1:00-4:00 client work. 4:00-5:00pm Emails and flex-time.

Third, work in sprints. Personally, without the Pomodoro method I’d be useless. But with it, I can get a LOT of work done. For me, I work in 45 minute sprints for almost everything but writing. For some strange reason I write faster in a 25 minute Pomodoro. So I just do that. Regardless, find out what works for you.

4. Loneliness

star wars lonely

Source: Pinterest

Freelancing can be lonely.

For me, I work all alone in my home office. And though I see my wife and kids throughout the day I usually don’t see other people.

But what if you are single? Or what if your spouse works? Well, that can be really hard. It’s hard when my wife takes the kids out to the mountains and I’m home alone. But I have it easy. I know that she’ll come home.

Not everyone has someone who will be home tonight.

The Fix

But loneliness can be fixed. If you want to destroy loneliness then there is a simple fix: connect with other people. Call a friend on the phone and just talk. Call your parents and have a good chat with them. Take the initiative and reach out

Or you can change up where you work. Go work in a library, coffee shop, or a coworking space. This way you’ll be surrounded with other people, and have ample chances to connect.

And connect you must.

But what if you feel like you don’t have any friends, or you don’t have family you can talk to?

Then start serving other people. Not only will you forget your own worries, but you’ll start to become friends with the people that you serve. Or, if you serve with other people you’ll become friends with them. It is human nature to gravitate towards people who are good, kind, and generous.

So serve. Be good, kind, and generous. And people will gravitate towards you.

At last, make sure that you get out of the house at night. Go to a meetup, an event, or just get together with some friends.

And if you do these things you’ll cure your loneliness. You’ll meet other people and connect with them.

The surest way to cure loneliness is to serve someone worse off than you.

5. The Fear of Famine

star wars milk

The fear of famine is real. Too often there is a feast of freelance work, followed by a disasterous famine of epic proportions. For me, I’m having a feast right now. Last month I made over $10,000, and I’ll make more than that this month.

But, just like Joseph in Egypt, the famine will come.

And that’s when most freelancers quit. They just go back to an employer because they are scared that they won’t make enough to make a living.

And there are times when the fulltime job is the right choice. But, remember that full-time work is an illusion of security. At any time your boss could fire you and you’ll need to find more work.

Yet it’s different for freelancers. Instead of having one client (your boss at your fulltime job) you can have many clients. And if one of those clients fire you or runs out of work then you can scale up work with your existing clients, or just get some new ones.

In short, if you want real financial freedom you need more than one client. Ask yourself. If you had to lose some revenue, would you like to lose 100% or just 20%? That’s the difference between having one client, and 5.

The Fix

The fix is to have more than one client. Try to shoot for 3-5 clients. If you have 1-2 clients then you lack the financial protection you need, and losing one client will be a blow. So, start connecting. Keep up with your outreach. Always be willing to help, and ask often for referrals. And soon enough you’ll have enough clients.

Wrapping Up

The fears of freelancing are real.

But you can’t overcoming them without effort. So, do yourself a favor. Pick the fear in this list that scares you the most, and defeat it.

And until you do, you won’t have what you really want. You’ll just be sitting in fear, waiting for the perfect moment. Instead, move at the right moment. And that moment is now.

See you on the other side.

“The best things in life are on the other side of terror, on the other side of your maximum fear, are all of the best things in life.” - Will Smith

-Stephen Godfrey

P.S. If you want to start freelancing you have two options. You can wait, patiently, while I post new articles. Or, if you want to start freelancing and earning money this week, I have a course you can take. By taking the course you’ll learn how to specialize, how to find clients, and how to price your services. So sign up now, and I’ll teach you how you can earn more money freelancing and have more time to do what you want to do in life.

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