7 Things I Learned In 7 Years of Freelancing

By RJ McCollam


Freelancing has seen a pretty impressive rise in popularity over the past couple of years as brave souls leave the promise of a steady paycheck in order to do their own thing. Most freelancers can’t make it their career and often times end up with a job again. This doesn’t mean that they failed as a freelancer, because working for yourself isn’t for everyone.

I turned to freelancing when I had nothing to my name. I was newly married, had just gotten my car repossessed, and knew it was time for a change. Now I support my family entirely from my freelancing income.


Here are the 7 most important things I have learned since I began freelancing 7 years ago:

1. Freelancing Requires A Lot Of Self Discipline

I remember the comments I got when I told people I was going to quit my job and start working for myself at home.

“Oh man, that’s so cool I’m jealous”
“Are you totally going to work in your underwear?”
“It must be nice to not have a boss constantly nagging you to get things done”
and many many more…

From the outside, working for yourself looks awesome. The reality of it is that when you are in control of what you do and when you do it, it is all too easy for you to waste away your days. When you know you don’t have a boss checking for when you make it to your desk, it is all too easy to hit that snooze button a couple extra (try 10) times.

Everyone is different in how they work, and understanding what your optimum work situation is, is important to being a successful freelancer.

For me, I worked to find when I was most productive during the day and then set a routine around that. I keep mostly normal business hours, but maybe for you night is when you get your best work done. That’s 100% OK as long as you find a routine and stick to it.

If you can keep yourself disciplined on a regular basis, you will deal with less stress and also be able to schedule and manage your time more efficiently.

2. It Takes Money To Make Money

Remember how I had nothing to my name and just had my car repossessed when I decided to start freelancing? Money was something I didn’t have and the thought of spending the money I did have on a business seemed impossible. I think a lot of freelancers try to watch the money they spend and often think of services or tools that might help them as a luxury. I know I did.

Over time, I started to mature as a freelancer and really started to understand the idea of paying for convenience.

I started looking at purchases I wanted to make from a standpoint of ‘how much time will this save me’, or ‘how will this make my life easier’ instead of ‘how much does this cost’.

Here’s the secret — the things you can do to save you time or make your life easier give you more capacity to put out better work. Let me give you a recent example.

Almost a month ago, I spent $1000 on two things. A course about freelancing and a lead service. I actually feel like this is a steal because if I land one client from what I learned in this course or one of the leads I am sent, I already make my money back and then some.

I didn’t get held up on the fact that my bank account would be $1000 smaller after the purchase; I looked at it as an investment to make much more money than I spent.

3. You Need To Be Flexible

I tend to think I know the best way to do everything. Ask my wife, she will 100% agree. This is not my best personality trait because it can be very off putting. As a freelancer, I work with many other people who prefer to do things their way and ask that I adapt to them.

Being flexible as a freelancer means that you are able to work in a style that best suits who you are working with. Most of the time, that person being the client, a.k.a the person who is paying you.

I am not saying you need to be a doormat for people to walk over, but it is important to take into account the other party’s situation. You don’t want to make things harder than they need to be for them, so learn to be flexible.

4. Communication Is Key

This one is easy. Clients love working with freelancers that communicate well.

Sounds obvious I know, but how many times have you worked with someone and they have a horror story about another freelancer they worked with — usually based around the freelancer not getting back to them or being difficult to deal with.

Make sure you respond to your emails, even if it is just to say “Letting you know I got this and will get back to you in the next couple of days.”

Good communication is something that is very easy to overlook, but it is also something that can lead to lots of referrals and more work.

5. Honesty Always Wins

At the beginning of my career I never wanted to deliver bad news to a client. Maybe that meant agreeing to a project timeline that really spread me thin, or telling them something was ready to go when I knew it still had bugs in it.

Working that way only got me in trouble. It also put me in a constant state of stress dreading seeing a clients name pop up in my email because they found the thing that was wrong.

Our parents were right — honesty is the best policy. Don’t overcommit yourself and even if it means you are going to miss a deadline, just be honest. In my experience, clients appreciate the honesty much much more than a crappy end product.

6. Want To Do A Good Job

I already talked about clients telling you their horror stories of working with other freelancers. It’s unfortunate that there are freelancers out there only out to make a quick buck without much regard for the work they do.

There is something to be said for wanting to do a good job and that usually comes through in your end product. Clients want to work with someone that genuinely cares about what they do and will do a good job for their business.

Take pride in your work. It shows and is appreciated by others.

7. Building Relationships Is Your Best Form Of Marketing

I attribute the majority of my success to the relationships that I have made with other freelancers and agencies. It is because of these relationships that I have been able to enjoy steady work, but how do you find and create these relationships?

Treat everyone you work with as a potential new relationship. If you work hard to impress and deliver, that can help form a new relationship that then produces more work.

When dealing with clients, that means referrals; when working with other agencies, that means more consistent work.

What have you learned?

In your years of freelancing, what have you learned? I’d love to hear what you have to say. Tweet me at @rjmccollam and let me know!

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