My Biggest Freelancing Mistake

Freelancing and climbing a tall mountain have more in common than you might think (in this freelancer’s opinion)

This summer, amidst the COVID chaos, I passed through my two year freelance anniversary.

There have been ups and downs along the way. Great projects and ones that I truthfully didn’t enjoy so much. And when I embarked upon the freelance journey, I probably wasn’t expecting to have made it even this long. But I did; and here I am to write this post.

During this two years, and the three years prior during which my freelancing was a side hustle, I have made just about every mistake in the book.

There have been plenty of conventional ones — like taking a while to figure out how to price my work — as well as plenty of more unique ones.

In the latter category, I would put things like:

  • Not trusting my gut instinct (repeatedly)
  • Prioritizing outbound marketing too much — to the expense of not developing a good enough inbound game
  • Not realizing, until recently, that most “freelancing problems” are in fact classic sales problems. And not picking up a sales textbook until about six months ago. (If you are a freelancer you are also a professional salesperson whether you realize it or not)

But I wouldn’t call any of these my biggest mistake (and note, I’m avoiding using the word ‘regret’ here intentionally).

Rather, that would be:

Not Realizing How Hard Freelancing Is From The Outset

A friend of mine recently changed his WhatsApp status to: “life is hard, that’s why noone surives.”

And that little humorous nugget actually contains a very large grain of truth when it comes to freelancing.

A damaging aspect of my self talk that I’ve come to understand over time is how much I beat myself up over what I have achieved (or haven’t achieved). I’m making an example out of my own faulty inner dialogue, but I’m doing so because I believe it’s reasonably commonplace.

This thought is usually preceded by an affirmation of how hard I have been working — because I usually have.

So the thought in its totality goes something like this:

“I’ve been pulling 70 hour weeks and I’m still only earning X. Surely, I deserve Y. If I’m working X hours a week and not earning Y then I mustn’t be very good!”

At the core of this deranged way of thinking, I believe, lies the following faulty assumption: freelancing (life?) isn’t all that difficult, so if you find that it is, then the problem must be you.  And if you’re also using this flawed stick to beat yourself up, then I’m here to gently request that you stop. I’m also here to tell myself — and you — that the underlying premise you’ve been weaponizing against your own psyche is completely flawed.

Freelancing, in my opinion, is one of the most difficult occupations imaginable. Especially so if you’re a freelance writer which has its own unique set of challenges. And particularly now when barriers to entry have been drastically lowered.

Competition is fierce. Freelancers compete in a worldwide marketplace. And sadly, the enormity of the supply flooding the market makes it very difficult to charge a viable rate.

Freelancers typically do not enjoy benefits — which means that they have to either battle even harder to incorporate those into pressurized rates or suck things up and work on weekends and sick days.

Freelancers have to do all this (mostly) alone — without colleagues to lean on for emotional support, accounting to deal with invoicing and payments, or a marketing and sales team to deal with attracting clients and getting them to sign along the dotted line.

In my opinion, the biggest antidote to the almost inevitable stresses of freelancing is a very simple one:

It’s okay that it’s hard. It’s almost meant to be this way.

Once you understand and internalize this you can do a few things:

a) Stop beating yourself up if you’re not achieving the level of success you believe you deserve. If freelancing is two times as hard as conventional employment — or three — then you might just have to be patient as your progress up the mountain might be two or three times slower.

b) Stop feeling like an underappreciated hero for putting in massive effort and getting back only normal return from the marketplace. As painful as admitting this to yourself might be, this is an insidious form of victim mindset that it’s better to get out of.

Now, I have to make another cup of coffee and get back to cranking out another piece of work for a client. I slept about 4 hours last night and could really use a nap right now but — between finishing this and the podcast I need to be on in about an hour — there simply isn’t time.

It’s bloody hard at times. Right now, I’m exhausted. But that’s okay. Because it isn’t supposed to be easy.

Freelancing is not supposed to be easy. But, paradoxically, I have found that accepting that actually makes it easier.

My advice to myself and to anybody else pursuing this path, whether temporarily or for the long term:

Accept the difficultly. Embrace it if you can. Accept that putting in extraordinary effort for ordinary return is normal much of the time (particularly early on). And continue unfazed with the climb.