Why Your Freelancing Life Doesn’t Seem Real
By: Daniel Rosehill
Tags: Career Development, Freelance, Freelancing, Professional Development, Careers

Why Your Freelancing Life Doesn’t Seem Real

This super cheesy graphic was courtesy of Pixabay

In another interesting thread from the freelancer writers’ subreddit, /u/StuBermann asked (paraphrased, especially to keep the language PG-friendly for you younglings):

“What’s the end goal for a freelancer? There’s no corporate ladder to move up, no promotions, no partnership or managerial position you can work towards. Even though it’s much better than being a corporate robot, I’m still just trading time for money.”

Stu (I’m going to assume it’s a Stu) then floated a few ideas. He could:

Create a content agency

Build and grow his own network of sites

Go down the course route, developing a writing course (don’t do it, Stu!)

Create a lead generation site for writing work and sell the leads

Keep writing but invest the earnings in something else

Write an epic fantasty series and sell the rights to HBO

Create a software tool for freelance writing

Build and sell content websites from scratch

How Can We Ensure Growth?

Stu’s thread caught my attention because I spent a good chunk of Friday evening discussing this very topic with my reluctant unwitting business strategist (that happens to be a family member). This chat lasted three hours which means that I’ll probably need to do some private journalling time before I can inflict that kind of misery again.

I also thought it was interested that although I know nothing about /u/StuBermann (isn’t that the odd beauty of Reddit?) that it seems as if we’re doing a lot of the same thinking.

For instance I also dream of writing a series and selling it to a television network ( — my script is roughly for a satirical series laughing at the ridiculousness of moving to Israel. I have the opening scene clear in my end which is exactly what happened to me: you get to the airport and the guy who’s supposed to greet you doesn’t show up and then some burly Israeli taxi driver strings your worldly possessions to the roof his taxi with some lanyard that looks like it fell off the back of a truck somewhere in Ashdod while he drives you across the country, to a dingy absorption center, at what feels like twice the legal speed limit. The target audience is probably an Israeli station rather than HBO. But I digress — ).

Like the original poster (OP), I’ve also thought frequently about starting an agency.

But more than those similarities, I also feel like /u/StuBermann and I are going through the exact same thought process — despite the fact that we’re probably thousands of miles away and probably also have relatively little in common besides the fact that we’re both freelance writers.

Perhaps, like me, Stu is inwardly surprised that he (or she) is succeeding at making a living while working from home on the internet. Like me, Stu might struggle with imposter syndrome and wonder if the day is nearing when his clients will realize that he’s actually a massive fraud.

Maybe Stu also feels at times like he’s living his own real life version of The Matrix. He might wonder, at times, whether somebody slipped him a red pill while he was sleeping one night and whether his clients aren’t actually real but rather some clever AI bot that have been imbued with the ability to provide feedback and master corporate speak. (About three months ago, I actually jokingly told a client that I wasn’t sure he was actually a human. “I’m real!” was the pleading message I got back. But it took actually meting for coffee before I was fully convinced…)

Perhaps, like me, Stu periodically pauses after a grueling day at the computer, maybe with his favorite alcoholic concoction in hand (is Stu a beer guy or a whiskey man?) and wonders why — despite making an objectively reasonable salary doing this — there is a voice inside his head that says “WTF am I doing with my life!”

Are You Creating Meaningful Work?

Firstly, I think that ensuring growth as a freelance writer is essential.

My post above covers the various ways in which I think we can engineer that. Here it is again.

Secondly, I’m perfectly fine stating for the record that freelance writing probably isn’t my ultimate goal. Writing is a long term goal of mine in the sense that I love the process of writing and love trying to influence people with words (I also love reading other writers’ work). But writing for corporate clients, at least as a freelancer, might not be.

When I “dream big,” I tend to think more along the lines of running a startup or managing communications for some famous politician (my first career dream was becoming a speechwriter!). Periodically I have great ideas but haven’t found time yet to action them — between client work and writing I’m, well, usually too busy. That time, I hope, will someday come.

All that aside, I think that Stu’s post teases out a few very important observations. And this is where I think we find common ground and probably many others do too:

Firstly, I think that as creatives, us writers need passion projects. I don’t think my clients would be offended if I told them that content marketing, and helping them write it, isn’t my ultimate passion in life, even if I’m perfectly good at it. Although there’s a good chance that they mightn’t hire me again. Has anybody actually dreamed about becoming a corporate blogger when they’re all grown up? Is it okay if we can admit, publicly, that that also includes many of us freelance content marketing writers? I would guess that there are few writers for whom that is truly the case. My hunch is that both Stu and I aspire to creating greater and more meaningful work than the type we currently do for clients. This is why, I’m guessing, we’re both drawn to the idea of creating some of our own work. I think if we’re both wondering “where is this going?” it’s fair to assume that we’re both not feeling a creative itch that our day to day work doesn’t satisfy. It’s leading us to question, in the small hours of the night, where is this going? This is what we’re doing now. But what do we ultimately aspire to do?

I don’t think my clients would be offended if I told them that content marketing, and helping them write it, isn’t my ultimate passion in life, even if I’m perfectly good at it. Although there’s a good chance that they mightn’t hire me again. Has anybody actually dreamed about becoming a corporate blogger when they’re all grown up? Is it okay if we can admit, publicly, that that also includes many of us freelance content marketing writers? I would guess that there are few writers for whom that is truly the case. My hunch is that both Stu and I aspire to creating greater and more meaningful work than the type we currently do for clients. This is why, I’m guessing, we’re both drawn to the idea of creating some of our own work. I think if we’re both wondering “where is this going?” it’s fair to assume that we’re both not feeling a creative itch that our day to day work doesn’t satisfy. It’s leading us to question, in the small hours of the night, where is this going? This is what we’re doing now. But what do we ultimately aspire to do? Freelancers need growth as much as in-house people do. I’ve made this point before. There’s a very real threat that freelancing will turn into the work for yourself version of a dead end entry level job if you let it. I’m currently strategizing how I can upgrade the type of work that I do in the next calendar year. Everybody has ambitions. Few are happy to do the same thing year in year out. In a paradigm in which growth isn’t a built-in feature, it’s vital that we devote time to making it a reality.

Does This Feel Real To You?

Does your freelance work feel like The Matrix?

Let me be brutally honest.

Although I’ve about to enter my third year as a full time freelancer — and my average salary this year has been above the national average where I’m based — freelance writing doesn’t yet seem real to me.

Part of the cause is that I have prioritized working with international clients over local ones. That means that I haven’t gotten out of the office as much as I’d like to meet and great clients and attend things like conferences and trade shows. Increasingly, I realize that this is an unsustainable approach, or at least an inherently unsatisfying approach (for me).

I have a social life — sure. Am I a hermit? No. But if all working life can be conducted from a home office behind a monitor — then I think there’s something deeply unfulfilling about that.

So if you’re in the same boat, I don’t think it’s surprising that you might be thinking along the lines of where this leads to. Because evolution is necessary or you would eventually go crazy.

I have no idea about /u/StuBermann’s work life. But in my case, running an online business —albeit a relatively thriving one — also simply doesn’t feel secure. Again, this prompts me to think about evolution.

If I can’t meet my clients for a drink, get the inside scoop on what’s going on for them, and establish a real-life camaraderie, then I know that I remain but an amalgamation of pixels to them. As they are to me. To succeed in the long term, that needs to change.