The Secret Thoughts of a Serial Freelancer

“Stop thinking of [talent] as either family or free agents. Think of them instead as allies.” — Tim O'Reilly

You could say that I’m a serial freelancer. Yes, the dreaded “f” word.

It’s probably not what you are thinking. I wasn’t forced to become a freelancer. And I don’t specialize in design or SEO. I chose to become a freelancer. And I chose to become a comprehensivist, or in my specific case, a full-stack marketer.

Because I’ve been freelancing since before it was cool, I’ve experienced my fair share of difficult clients. Fortunately, the pain of working with difficult clients eventually transformed into happiness from landing phenomenal clients.

Fifty shades of clients later, I have a few candid, insider secrets that I want to share with those of you hiring and managing freelancers. And before you count yourself out of this article, keep in mind that by 2020, 40% of America’s workforce will be comprised of freelancers — that’s 60 million freelancers.

According to Harvard Business Review’s Agile Talent, more of the world is headed in the freelancer’s direction, focusing less on traditional employment arrangements and more on talent however it is best found and arranged.

The time to understand freelancers is now. Here’s what you need to know.

1. You don’t need all those specialists.

I always find it sort-of comical (and totally dreadful) when I begin work with a new client, and all of these specialists come out of the woodwork.

A recent client, and arguably the most reputable brand I’ve worked with to date, hired me to grow the online presence of one of its side-projects. The internal stakeholder hired a blog editor to publish two to three posts per week, loads of staff writers to write one article per month, an outreach specialist to secure interviewees for these staff writers and me to write copy for its newsletter and social media channels.

Not only was this a complete waste of resources, but it also provided an annoying experience for people not on the company’s payroll, such as the abovementioned interviewees. Think about it. These big-name influencers, who have very little time, don’t want to deal with an outreach specialist, only to be introduced and cc’ed to the writer and then eventually the editor, if edits are needed. Not to mention, it takes wildly longer to get anything accomplished.

Good luck getting an influencer to respond to your emails ever again after employing a clunky process like this one.

A more productive use of resources would have been to hire a comprehensivist — the opposite of a specialist — to manage the blog, conduct outreach, and manage social. The only additional freelancers needed would be writers, who should conduct their own outreach, and pull social media “quotables” from their articles.

2. Freelancer isn’t synonymous with virtual assistant.

Unfortunately, most clients see freelancers as a cheap pair of hands, who do exactly what you want exactly how you want it done. If you want a freelancer like that, I highly recommend Fiverr.

If you want a freelancer that gives you a competitive advantage, don’t think like this.

Really good freelancers typically chose to freelance for two reasons — both of which are not to be your poor VA. Instead, they opt for the untraditional route because they can make more money, and they can have more autonomy over their work.

In fact, more than 40% of freelancers said that the freedom of choice in their work is the most appealing feature of freelancing.

You can tell us what to accomplish, but you can’t tell us how to accomplish it. Eric Schmidt puts it beautifully in a piece from 1999.

“You might as well say to a great artist: ‘I’ll describe to you what a beautiful painting is. Then I’ll give you an idea for a particular painting. I’ll tell you which colors to use. I’ll tell you which angle to use. Now you just paint that painting.’ You’d never get a great painting out of any artist that way — and you’ll never get great work out of your geeks if you try to talk to them like that. You need to give them a problem or a set of objectives, provide them with a large amount of [resources], and then ask them to solve the problem.”

Let’s forget the fact that freelancers despise being told how to reach their goal(s), and consider a more pressing one.

According to the IRS guidelines, behavioral control is a key differentiating factor between independent contractors and company employees.

Behavioral control means that while employees must follow your methods of madness, contractors don’t, unless of course, you want to give them all of the benefits that come with full-time employment.

3. Freelancers want to be included.

Freelancing is lonely so it really sucks when you get invited to a company Slack group of a new client only to have its full-time employees refer to you as an “insultant” or merely tolerate your presence.

According to Agile Talent, freelancers want to be included.

“Like full time employees, externals want to do meaningful work; grow in competence and opportunity; be respected, trusted and engaged; be treated as part of the team; receive ongoing communication about the issues that bear on their work and feel rewarded fairly and recognized for their contribution and effort. Too often they feel instead merely tolerated or treated as suspect by organization employees with whom they work. They feel unappreciated by management and powerless in dealing with the administrative bureaucracy of partner organizations.”

4. You can’t handle feedback.

While we’re on the topic of “insultants,” let’s chat about a sparingly appreciated term, known as radical candor.

According to First Round Review, radical candor results from a combination of caring personally and challenging directly.

As consultants, it’s our job to tell you, sometimes in grave detail, where and how you’re screwing up. We try to do this as nicely as possible, but most of the time it’s ill-received, and the client retreats with hard feelings.

Some freelancers will try to avoid this by simply telling you what you want to hear and complying with every thought and/or conclusion that falls out of your mouth. Trust me, you do not want a freelancer who does this. It either means, they have no idea what they’re doing, or they only care about the benjamins — and getting those benjamins as fast as possible.

The best freelancers will tell you the truth — even when the truth is hard to tell.