Anxiety management as a freelancing skill

Why reassurance might be a necessary part of the job

Daniel Rosehill
6 min readMar 4, 2021

Firstly, thanks to /u/Penguin-Pete, on the always interesting world of Reddit, for mentioning this Medium publication on the freelance writers’ subreddit.

Reddit may have connotations for being something of an edgy and aggressive part of the internet (sometimes that’s true), but the freelance writers’ subreddit (/r/freelancewriters) contains lots of level-headed discussion about the art and craft of making a living as a freelance writer. 65.6K members and growing. Check it out.

I mention that also to credit the subreddit which is where this thought originated. Sadly in the sleep-deprived state I’m writing this post in I can’t remember who exactly said it. But some wide soul put this out and I thought it was worth developing into a post.

Fact: Nobody Really Cares About Your Freelance Writing Portfolio

I tend to overthink things.

I’ve spent far too much unproductive time hemming and hawing over the best way to portfolio my freelance writing work (an endeavor complicated by the fact that most of it is ghostwritten; for how to tackle that issue, see below).

Should I separate things by content type (article, white paper)? By niche (IoT, MarTech)?

Should I go for a minimalist text-heavy style or try to make things look pretty with lots of fancy graphics?

I worry about technical concerns. Should I put the portfolio behind a password on Wordpress? Should I share clips through Google Drive? Or just go old school and email them?

After years spent periodically grappling with these futile and frankly trivial details, I finally had a moment of clarity:

It doesn’t matter! (Here’s why)

Your Average Internet Lead Is Anxious And Distrustful And Suspects You’re A Liar

I’ve been marketing myself through the internet for several years now, leveraging just about every channel in the book — from PPC to inbound — to attempt to keep my pipeline full and stay in business.

Internet marketing works, even though it takes a lot of effort to get going.

But there are two factors that I think those of us selling services online massively discount, to our own detriment. I’m writing this for freelance writers. But I contend that these factors are applicable for anybody selling to others in an online capacity (which, in today’s world, is an awful lot of people!)

Firstly, it’s really easy to make stuff up online. Like really easy. Trust me on this one. (Even if you do, read my guide to creating fake online identities anyway … this is going to be a growing problem in coming years).

Don’t think that your prospects assume that you’re above pulling all kind of tricks including faking testimonials, plagiarizing other writers’ work, and lying about what you know (and don’t know) about what you writ eabout.

Secondly, while more and more of us are working online in remote environments, ultimately the internet is …. still the internet.

Freelancing periodically makes me depressed — literally! The usual cause? Not business woes but clients who treat freelancers like garbage. I take it personally even though I know I shouldn’t. But you know why a lot of freelance clients treat freelancers like garbage? Because when you don’t share a desk with David the SEO guy you don’t tend to think of him as a human. He’s …. pixels on a screen. The corollary: he’s disposable.

Why does every freelance writing lead ever (almost) ask to see your portfolio?

To answer that, let’s step into the buyer’s shoes for a minute.

Does the buyer really care whether your portfolio has flashy images or is laid out in reams of text (those factors I spent years agonizing over)?

Perhaps marginally, from a readability standpoint. But not an ounce beyond that.

Instead your average buyer of freelance writing services, I propose, is anxious and distrustful of anybody he or she encounters through the internet.

This means that the onus is firmly on our shoulders — as freelancers — to prove to clients that we’re not the latest dodgy Upwork freelancer who is going to let them down.

Seen from the perspective of this innate anxiety bias, the whole act of freelance writing clients looking for portfolios begins to look starkly different.

It’s an exercise in proving potential value — sure. But equally it’s about rebutting a presumption of bad faith. Unpalatable? A bit. But that’s business.

Your average freelance writing buyer wants reassurance that:

  • You’re — broadly speaking — legit
  • You’re a competent writer
  • You know how to run a freelance writing business
  • You have the subject matter expertise necessary to pull off the project

Once you understand the above, you can see why sending on a link to a hundred clips to a lead is actually counterproductive. They don’t need that swarm of information.

Instead you can send them:

  • One piece of your best writing. Only one piece is necessary to show that you’re theoretically capable of writing great stuff.
  • One piece of writing in the subject you’re looking to write about.

To rebut the other inherent allegations — you don’t know what you’re doing and you’re a scammer looking to take them for a ride — you can rely upon traditional marketing tactics:

  • Testimonials demonstrate social proof and show that others have trusted you
  • Case studies demonstrate your ability to achieve concrete results
  • Client logos achieve much the same thing, particularly if they enjoy good brand recognition
  • Blogging about how to run a freelance business can help show that, broadly, you know what you’re doing

You possibly can’t do much about the fact that — as a collection of pixels on a screen — you’re not quite real in the client’s eyes (in the same way that the colleague they see in the office every day is.) But you can:

  • Try to meet your client in person if you’re in the same country
  • Share something about your personal life, or enquire about your client’s when appropriate to do so.

Small touches in relationship management can help the client see you as a human rather than as just a task executor.

People Are Nationally Cagey About Those They Encounter Online. Selling Online, We Have To Deal With That Skepticism

It’s true that the internet is revolutionizing our world and that there’s a growing willingness on the part of companies to hire both freelance and remote talent.

But that doesn’t mean that the picture is entirely rosey.

I contend that people are always somewhat distrustful of people that they encounter online. And for good reason. The internet makes it easy to hide who we are and whether or not we’re actually good at what we do. Many clients trusted online freelancers only to be burned. Their shields will be up the next time they’re in the hiring seat.

What can we do about this?

Instead of trying to dazzle your next freelance writing lead with 100 articles you’ve published, I suggest that it may be better to assume them to be anxious and suspicious and then do everything to proactively gain their trust and confidence.

It’s about trying to wow them — yes. But it’s also about providing them reassurance that they’re not walking into a trap by hiring you.

Show them that you’re a good writer. That clients are prepared to trust you with their projects. That you’ve delivered results previously. It should put your potential clients at east. And you.

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Daniel Rosehill

Daytime: writing for other people. Nighttime: writing for me. Or the other way round. Enjoys: Linux, tech, beer, random things. https://www.danielrosehill.com