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4 things I Wish I’d Known Before I Start Being a Freelancer

Jacob McMillen

I’ve been freelancing for around 5 years now… full time for the last 3. I enjoy the freedom, the high pay I’ve been able to achieve, and perhaps most importantly, the diversity of activities.

Of course, you can’t do something for 5 years without learning a few things, so I wanted to take a moment today to share a few of the things I wish I’d known back at the beginning. I’ll also mention a few things I managed to avoid that seem to be common tripping points for many freelancers.

I hope that’s enough intro for you, because we’re diving right in.

1. Pricing Has Nothing to Do with Service Quality

A lot of people tend to think that price is directly related to quality. Sure, you know of some exceptions, but on average, people to tend to earn what they’re worth, right?

No. Not with freelancing. In fact, you need to completely get out of that mentality if you want to make real money as a freelancer.

The reality of capitalism is that pricing has nothing to do with quality. Pricing is 100% determined by what people are willing to pay. As a freelancer, my service cost is based entirely on what I can negotiate from a client as opposed to the actual value of my work.

If you want to make more money as a freelancer, you don’t need a better service, you need better negotiating skills. Here’s the cliffnotes for making that happen:

How to Negotiate Higher Pay

Quality is important, of course, and we’ll talk about that next, but it has virtually nothing to do with your pricing. I’ve made $12 and $800 for essentially the exact same article. If you can change your mentality and understand that price is a matter of how much your client is willing to pay, you can immediately begin making more money for the exact same amount of work.

2. Your Long-term Success Will Depend Entirely on Quality

While the quality of your work will not determine how much you earn on any given project, it WILL determine how many projects you get from repeat and referred clients, which tend to make up the bulk of a successful freelancer’s income.

Don’t let this detract from my previous point. You can do $800 quality work and get paid $12 the rest of your life if you fail to grasp point #1.

If, however, you are successfully charging $800 for $12 quality work, you will typically find yourself failing to attract recurring business. There are always exceptions, of course, and if you are in a market where clients tend to have limited understanding of the service provided, you might be able to get away with scamming. But honestly, if your goal is simply to rob people, becoming a freelance service provider is a horribly inefficient way to accomplish that.

The best way to succeed over the long haul is to provide consistent value to everyone you work with. When a client comes away thrilled with your work, there’s a fantastic chance that will turn into additional work and a referral or two down the road. When this happens with EVERY client you work with, you are essentially building a passive lead-generation network.

Focus on doing quality work and continue to improve as your career progresses. This is THE best way to achieve long-term success as a freelancer.

3. One-Time-Only Free Work is the Easiest Way to Open Doors

I’ve seen two opposite but equally dysfunctional trends among both new and experienced freelancers alike.

On the one hand, there are a lot of insecure freelancers who will do tons of free or underpaid work in the hopes of landing new gigs or higher pay down the road. On the other hand, there are freelancers who scoff at the idea of ever doing something for free, and they miss out on a lot of gigs as a result.

Free work can be one of the best (and ultimately cheapest) tools for opening doors, but you have to utilize it correctly. Here’s what I mean.

When someone is evaluating whether or not to hire you, they are essentially trying to make an educated guess about whether or not you can deliver what they need. They are trying to guess whether hiring you will result in a positive ROI. If you can answer that question for them, you can add them to your list of paying clientele.

This is where a one-time free service can come in handy. You can remove the question by delivering something upfront that proves your value. If you are doing quality work, this is a great way to grab recurring business.

For example:

  • Writers can write up a free article and pitch a recurring gig
  • Developers could build a free landing page and pitch a full website
  • Designers could create a logo and pitch a full design package

You may have noticed that the free work is followed with some sort of pitch for additional services. This is really important.

Don’t just do free work for anyone. Only try this with people who have a high potential of giving you more work.


If you produce a positive ROI for someone and they respond by asking for more free work, they have zero interest in hiring you for paid work. You can ALWAYS find people willing to take advantage of you.

4. There’s a Mix Somewhere That Will Give You Both Passion & Profit

There’s kind of a myth out there that says you should just pursue your passion and the money will follow. This simply isn’t true.

When I first started writing professionally, I was really interested in writing about sports. But guess what? So was every other twenty something guy who fancied himself a writer. And thanks to the supply-demand relationship that drives pricing, this means if you make $15 per article as a freelance sports writer, you are actually doing pretty decent.

So instead of writing about sports for $15 per article, I write about marketing for around $600 per article. And I enjoy it.

It’s not my favorite thing to write about, nor is the most profitable topic I could write about. It IS however, a topic that produces the perfect mix of passion and profitability for myself. It’s enough for me on both spectrums.

That’s really the key to running your own freelance business – finding the perfect mix that allows you to stay interested while generating the income you desire.

A lot of people will spend a lot of time trying to “make it” in an area where there is very little money to be made – where people making a decent living are one in a million. I suppose if that’s your biggest dream and money is no option… go for it.

But the reality is that there is a probably a mix out there that will give you both the satisfaction you need from your career AND the income you need to have a life outside your career. Why not go for that mix from the beginning?


These are a few of the pointers I wish I’d had at the beginning of my freelance career.

  • You can lose a lot of money if you don’t have negotiation skills.
  • You can lose a lot of clients if the quality isn’t there.
  • You can lose a lot of time doing free work with no payoff.
  • And you can lose the work/life balance you want if you don’t find the right job mix.

If you’re a freelancer, I salute you and wish you the best. It’s a great career if you can avoid the pitfalls and keep up the hustle.