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Top 10 Reasons Why First-Time Freelancers Fail

Success over Failure

There’s quite a fetish for failure-as-fodder these days. Search “failure” on popular business sites like Forbes, Entrepreneur, or Inc, and you’ll get loads of articles on how it can be a great teacher.

I have to admit: I used to party on this bandwagon. Rally people to feel free to fail, as if it encourages higher-levels of creativity. Self-destruct certain projects just to see what happens.

Then the Harvard Business Review released their Failure issue. And I saw the cult of failure for what it was: a misguided attempt to ease anxiety.

This got me thinking. Do I have to fail at being a first-time freelancer to learn to be a successful freelancer? The answer is an unequivocal NO.

Listen, failure can be a great teacher—especially if you learn from someone else’s failure.

So, if you are a first-time freelancer and would like to become a seasoned one without having failed—then read on to learn the top ten mistakes first-time freelancers make and how to avoid them. Achieving success doesn’t require you to fall flat on your face first.

1. Too Much Competition

Creative people are confident. Cocky. Inside the creative board room at the agency they bristle with enthusiasm for their craft. But no matter how clever you think you are, you are going to have to work very hard to convince people to work with you when you are on the outside by yourself.

Just look around you.

The field is full of very talented people. Like it or not—they are your competition. And the sad truth is not every determined and talented freelancer can become a rock star. There are other people you have to compete with. You have to work harder than they do to get attention, land jobs and reap referrals. Otherwise the competition will eat you alive.

2. Obscurity Dogs You

Speaking of working hard to get attention…think of the most successful people you know. Doesn’t matter what field they are in: real estate, bartending or graphic design. The degree of their success is often proportional to the degree in which they are famous within their niche.

The degree of their success is often proportional to the degree in which they are famous within their niche.

People know their name. They refer their work. They know how to pick up guest posts and speaking gigs easily. This is the reward of popularity.

Without popularity and attention you won’t get leads. Without leads your business will die. See, your problem isn’t so much lack of money. It’s lack of attention. It’s that you are mired in obscurity.

This is where good marketing comes in. Good marketing breaks through the clutter, competition, and confusion. Good marketing starts with building a reliable brand—and promoting that brand like mad.

3. Lack of Hustle

When it comes to freelancing, execution is everything. Everybody likes ideas. But more importantly we like it when those ideas become a reality. Laziness, lack of organization and lack of prioritization do not mix well with freelancing. You can talk a great game as a freelancer, but you need to deliver on game day, which is every day.

Each work day you need to do the hard stuff first—then the fun work. Meet deadlines and then some. Keep your promises. Show your clients and the world that you can rock – that you have a motor. And as a rule of thumb you should always under promise and over deliver for your clients.

4. Poor Rate Model

One of the most common questions I get asked from freelancers is how much should I charge? To be honest, I can’t really answer that question for you. I can only give you some advice.

Here’s three pieces:

  • Experience: You get to charge less if you have minimal experience. You get to charge more if you have a lot of experience (which includes endorsements from big brands).
  • Customer’s Budget: You get to charge less if you work with non-profits and small businesses. You get to charge more if you work with big brands and their deep pockets.
  • Customer’s Expected Profit: You get to charge less if the client doesn’t expect to make much money off of your work. You get to charge more if they can expect to make a killing from what you do.

You will fail if you don’t price right. Price it too low and you could be making minimum wage before you know it. Price it too high and you may lose jobs.

Pricing is an art, you get better with it over time. And you get better at it the more you negotiate.

5. Can’t Negotiate

Ah, conflict. The essence of a negotiation. And what most creatives dislike most. We wouldn’t have jumped into our creative fields if we liked people and dealing with them everyday—especially on contentious terms.

But sweaty palms or not, you need to negotiate. You need to seek a win-win relationship with a prospect through tactics like these:

  • Building value first before mentioning price.
  • Suck in your teeth.
  • Shut your mouth.
  • Always go high.
  • Float a trial balloon.

Those kinds of things take guts. A little grit. But you can do it. If you don’t, then you’ll leave money on the table or get taken advantage of. And that’s a hard way to make a living.

6. Lack of Maturity

From inside the cubicle freelancing is attractive. It’s seductive. It’s the party lifestyle of the working famous and unemployed rich. Who wouldn’t want to sleep as late as they want, take three hour lunches and work six months out of the year?

If that’s how you view freelancing, then you are immature, not emotionally (though I’m not eliminating that option), but certainly professionally immature. Being a freelancer demands a massive amount of maturity. It demands discipline, confidence, organization, and courage.

7. Failing to Count the Cost

I quit my job without a plan B, without much of a savings, and without much of a clue as to what I was getting myself into. I wouldn’t recommend that approach. There are better ways to begin your freelance career.

Do you have six months of living expense? If not, keep your day job, pick up a few freelancing jobs and sock away that money before you quit. You’ll also need money for advertising costs, too.

And don’t forget about the emotional and relational toll that working for yourself can take on you and your family. My wife and I covered some of the roughest road in our fourteen years of being married during my first year of freelancing.

Count the cost before you cut the cubicle cord.

8. Too Many Distractions

Part of the allure of freelancing is working to our own rhythms. We get to make our own schedule. We get to do with our time (as long as we are mature and are getting our work done) what we want.

We could tackle that book we’ve been dreaming of writing. Collect our best designs together for an art show. Learning how to surf.

However, these things could easily become distractions. We could easily find ourselves spending half a day on non-essential tasks. Or get tempted to put off for tomorrow what we should do today (that being work) so we can finish a fun project.

There are other things that can become distractions when you work for yourself:

  • People – I work at home. My wife home schools our children. It was very easy for my son or daughter to pop into my office or the wife ask me a question. It was very distracting. We needed to set boundaries so I could focus.
  • Blogs – When I worked for someone else I could only write for my blogs at certain times. The hour before work started. The hour over lunch. Maybe a couple hours before I went to bed. I had boundaries.

    Not so when you work for yourself. If I’m not careful I’ll spend WAY too much time on a blog post—because nobody is breathing down my neck and I feel like I have all the time in the world.

  • Debt – I don’t think I’ve ever met one freelancer who hasn’t had some sort of debt at some time in their yearly work cycle. Jobs fluctuate. You might be busy in the spring only to find yourself bored stiff in the winter.

    Bills pile up. And debt hangs over your head. We may start to take lame jobs because we are desperate. That is a downhill spiral, friend.

  • Part-time Job – I’ve scrambled to nail down a part-time job when work was scarce. It’s an instinct. I think we’ve all done it. But if you get that job, then watch out: it could take away from your core freelance business. Working for someone else means you can’t make calls or answer emails on your boss’ time.

9. Letting Your Emotions Bulldoze You

Freelancing isn’t for the faint of heart. It’s an emotional ride. I cried like a baby my first day on my own. I was sure six weeks from that day we’d miss our first mortgage payment. In three months we’d default. And another six and we’d be on the street.

You can get dropped by a client one day only to have that income replaced the following.

I wasn’t rational. And that’s an extreme case. The future looked very dark for me until I got a grip. But don’t expect that darkness to go away forever. It can come back.

It’s an occupational hazard. You can work so hard (because you took every job that came your way) that you find yourself dreading the computer screen. You can get dropped by a client one day only to have that income replaced the following.

The temptation is to self-medicate. Drink two beers in the afternoon to get you through, four to help you get to sleep, eight to help you enjoy the weekend. I like beer, but I like self-control better. And you can’t control your emotions when you are drunk.

10. Giving Up Too Soon

Quick story. About halfway through our 32-day journey of the West Coast I was going to get the opportunity to spend some time with a great uncle. He was financially independent after building and selling his own manufacturing business.

I wanted to talk to him about working for myself. Pick his brain about success. I was looking for something exotic. But his advice was basic: work hard. Okay. And when I asked him when do I give up if working hard wasn’t cutting it he responded: when you can’t afford it.


It was simple in his mind. You threw in the towel when you were losing money. You could run into setbacks. Struggle with difficult clients. Bang your head over accounting issues. Juggle dozens of projects. But you didn’t quit until you were losing a lot of money.

So, what other reasons are there that cause first-time freelancers to fail? How did you make it over the initial obstacles that face freelancers? What are you still struggling with?

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