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8 Harsh Truths No One Tells you About Freelancing.

Renée Picard
Aug 24, 2017 · 5 min read

“The artist committing himself to his calling has volunteered for hell, whether he knows it or not. He will be dining for the duration on a diet of isolation, rejection, self-doubt, despair, ridicule, contempt, and humiliation.” ~ Steven Pressfield

Picture the digital nomad “working” from the beach, the millennial sipping espresso in a stark-white co-working office, or the single mom who appears to easily support herself while still spending quality time with her kids.

This is a realistic picture of the freelance life, right?

Anyone who’s been in it would probably beg to differ. While freelancers may have more control over their time, it doesn’t always lead to this freestyling, pretty fly kind of life.

It can be freaking hard — -but not in the ways that you might expect.

Don’t get me wrong: some people are really great at making it work. Some people take months to get to the phase where it feels easy and fruitful, but most people need more time than this to get where they want to be.

So if you’re in that place, don’t worry. It’s completely normal.

I started freelancing over six months ago, and since then it’s been a wild ride. In some ways it has been extremely rewarding, but it’s also been difficult in ways I never would have expected — -and I know it’s not just me.

One thing I know for sure is that, no matter how much time, money, skill or connections you start out with, running yourself as a business is absolutely not for the faint of heart.

If you’re newer to this lifestyle and struggling, you need to know that some of these emotional pitfalls are perfectly normal — but in the end, it’s how we work through them that makes us stand out.

Truth #1: You will need to fake it to make it (sometimes).

I am not a “fake it” person. I am genuine and up front about everything...but, there’s a place and time for some of this. I now understand that a little faking it can go a long way, and that being too open about things you aren’t feeling great about can also go long way, just in the wrong direction.

Truth #2: It’s not really about “time” management.

When we have to structure our own days, we are forced to look at the way we manage our physical, emotional and psychological energy throughout the day to be most effective. It’s not really about time so much as it is life-management.

Truth #3: You may need to intentionally work on developing your “boss” persona separately from your creative self.

Most of us grew up to be one of two types of people: the “boss” or the “employee.”

We are typically either the leaders who create the business, or we assist decision-makers in exchange for our daily bread — -aka, the money we need to live on.

Whether you call yourself a freelancer, solopreneur or entrepreneur, you must learn to position yourself somewhat separately as another person: the boss. The boss sticks to a schedule, makes sure things get completed, and takes no shit.

If you are a perfectionist (check) or an overthinker (check), you probably are also too attached to your work, which means that you will have a hard time completing and promoting your work unless you can become that objective observer.

As Steven Pressfield aptly puts it: “Madonna does not identify with ‘Madonna.’ Madonna employs ‘Madonna.’ ”

Truth #4: You have to learn how to value all of your work…not “only” the deliverables.

I’m still trying to unlearn a lifetime of being paid per hour — that is, an employee mindset of “I do what you say, you pay me,” rather than a business mindset of “here’s what I do, here’s what I charge.”

For me, this has been one of the most difficult mindsets to unravel.

Then you have all of the other tasks that don’t necessarily equate with immediate, tangible cash, but that you must do regularly regardless: pitching, research, networking, proposals, scheduling, blogging, social media, invoicing, strategy, marketing, learning more about the next new tool or technique…the list is infinite.

Part of the game is learning where to hone in on the squiggly and shifting profit-making curve when there are so many possibilities.

When we think of all of this in terms of possibility, then get clear on our priorities, the game can become completely exhilarating and empowering; but when we fall into the trap of seeing everything as an uncertainty, it can be a slippery downward slope.

Truth #5: Your ego will take regular beatings.

I’m pretty sure that 90% of freelancers out there has had a client “ghost” them in one way or another. The good news is that the risk of this happening gets lower the more experienced you are, so long as you’re learning from your mistakes.

Typically we’re brought up to show up “for” our family, our friends, our jobs. But when do we learn to really, truly, primarily, show up for ourselves?

Making mistakes like this and learning how to not take them personally is just one way that you are forced to learn how to show up for yourself as a freelancer.

This is not a choice — -it’s essential.

Truth #6: Well sheeey-it, it’s lonely in here!

Wait, where is everyone? Where did you all go?


(…cue tumbleweed…)

This is where genuine collaborating and networking comes in. Do it well, do it often, try different ways, and you will find crucial support, both professionally and emotionally.

Truth #8: Your victim mentality has no place here.

“Mindset” may seem like a trendy buzz word but there’s a reason behind its success: If you choose to work for yourself, there’s just no space for your victim mentality. This includes a mindset that thrives on lack, or just being stagnant.

The bottom line is that your bottom line is about exactly the opposite of this. Dwelling in perceived failure is not an option.

We all feel like failures sometimes (see truth #5).

So basically it’s buck up (I don’t mean be perfect, I mean be prepared to work on yourself every day) or do something else.

Through achieving connections and working with others, getting feedback, taking ongoing training, collaborating, networking, and heck, maybe even seeing a coach or counsellor, it’s imperative to develop practices that reinforce a certain mindset not of fakey “positivity” (or narcissistic ego) but an unwavering confidence about not only what you offer, but the who and the why behind that offering.

And that, my friends, might just be the ultimate challenge.


If you need help developing content that sticks to the bones of your biz, drop me a note — -I’d love to chat!

Renée Picard

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Content Marketing Writer & Editor