Twelve Ways To Destroy Loyalty With Freelancers

Freelancers and contractors will give one thousand percent to a client. The best way to get it is to show them a bit of consideration, decency and respect. Treating them like Uber drivers leads to poorer outcomes. (Photo of Falls Park, Belfast, Northern Ireland, by John Flood)

Freelancers and contractors will give one thousand percent to a client. The best way to get it is to show them a bit of consideration, decency and respect. Treating them like Uber drivers leads to poorer outcomes. (Photo of Falls Park, Belfast, Northern Ireland, by John Flood)

Holiday spending might have been strong this year, but for the contractors and freelancers that I know, it’s been a long dry season, laden with sharply reduced holiday spending, and deep uncertainty.

Several of my freelancing friends are coping with significantly reduced gigs and writing assignments. Two are completely out of work with few prospects. I’m even coming up short, due to unexpected reversals from several clients.

So, after sharing our common plight and discovering a remarkable similarity in our gig experiences, we’ve come up with a mission statement for the bloodless and unfeeling who couldn’t care less about those of us who live in a world of constant financial uncertainty.

Twelve Steps To Ensure You Never Instill Loyalty With Freelancers

1) Create complicated billing systems that ensure the single mom who’s writing for you doesn’t get paid around the holidays and can’t buy gifts for her kids. Don’t offer an apology of any significance.

2) Use Bric as a time tracking tool. Exporting Bric data is difficult. This will ensure that every week when your freelancer has to submit her invoice, she’ll have to struggle with Bric, which ensures she remains frustrated - and completely vexed by your fascination with lousy apps. 

3) When a freelancer joins the weekly virtual team meeting, don’t acknowledge them by saying, “Hello, it’s good to see you. I hope you’re doing well.” Simply ignore them and get down to business. Common courtesies (among the staff) are no coin in your realm.

4) Make sure your freelancers have to use at least seven apps and project management tools. A recommended list includes: Bric, Gmail, Basecamp, Wrike,, GoToMeetings, Nelson Staffing, Slack, Asana, and Toggl.

5) Use Wrike like it’s a panacea for all your missteps and failures. You see it as a miracle cure while your team is entrapped in its endless cycle of Wrike updates and notifications, new Wrike assignments, all the dashboards, calendars and reports - segmented by clients - and a dozen tasks and sub-tasks. In other words, Wrike the world until the world bows into submission.

5) As you stoke your start-up, never ever offer stock options or bonuses to your freelancers. Never give a freelancer a chance to be inspired by such notions. By doing so, they’ll only give you their mediocre best, which is what you’ll eventually pass on to your customers - mediocrity.

6) Welcome the New Year by reminding everyone that there are a lot of not-dones in Wrike.

7) Never give a wage increase - even to the most loyal gig contractor who, for years, has navigated your fickle Don Quitoxe-like twists and turns in direction; the unexpected and unannounced management resignations; the new hires that aren’t clearly defined for other team members; the unannounced strategy pivots; the changes in staff roles that are not announced; the new marketing goals; and let’s not forget the constant change of apps. 

8) Never reach out to a gig worker contractor for a one-on-one. Eschew phone calls. That way, your freelancer will feel like an Uber driver, on call at your every whim. There’s no rule that says you have to discuss the journey with them. They are, after all, a disposable resource. Think Uber. They’re there to get you down the road, advancing your own goals, and not for the common good.

9) Absolutely vow to never provide a head’s up that the company is going off a cliff, that assignments are being shut down, and that holiday season will suck for almost everyone on the team. Refrain from holiday greetings and bonuses.

10) Be the sole CEO without a partner, COO, or co-founder. That way, you can run your business open loop without brakes, and you won’t have to deal with a strong prevailing counter opinion. In other words, you are the CEO and the Emperor (with no clothes).

11) Run your start-up (or projects) with part-timers and fractional-time contractors spread out all over USA timezones. And, demand that they act like full-time employees. This will lead to a massive case of gig contractor cognitive dissonance, while ensuring your final products to your clients are mediocre, which will accelerate your company going off a cliff.

12) After you merge the company with another one, disappear.

If this manifesto doesn’t appeal to you, please contact us. We’d like to work for you.

Keeping Your Word Is Hard

In the frantic mix of our virtual meetings and Tweeting and emailing, “Slack-ing,” and “Wrike-ing” and “Toggl-ing,” there’s always a moment when we commit to something.

And, so the question is, do you keep your word?

As a freelance writer, I’ve had situations come up when, after a client has committed to a project, they suddenly didn’t live up to their commitment. Recently, a client offered me a research project that was supposed to be five to ten hours of work per week. But then, without warning, she disappeared for three weeks. And, as it turned out, she ended up doing most of the research herself.

Social platforms, texting, emailing and project management apps have made it easy to forget that freelancers are real people living on a precarious edge of financial uncertainty.  (Photo by John Flood, Albert Bridge, Belfast, Northern Ireland)

Social platforms, texting, emailing and project management apps have made it easy to forget that freelancers are real people living on a precarious edge of financial uncertainty. (Photo by John Flood, Albert Bridge, Belfast, Northern Ireland)

Early this year, another client committed to an ongoing writing and social media project that represented up to 10 hours per week. Her commitment had all the markings of a handshake agreement, and I took her at her word.

Instead, I woke up one Sunday morning to find an email that included the following, “My new Linkedin consultant and I, we find we’re really in synch . . . I’ve realized it would be easier (to work with her) . . All the best, and in thanks for your friendship.”

In both these cases, they’ve lost nothing. But in my case, I had declined other gigs in the process - all because I took them at their word.

The Gig Economy Is One Big Tinder

In the gig economy, hiring a freelancer on a job site like Upwork has begun to feel a lot like looking for hook ups on Tinder. After all, both platforms arbitrage human capital. One for love, the other for money. Both run on the unquenchable need for acceptance, which is one of our most basic human needs.

And, while in trafficking in hope, Tinder and Upwork are prone to preying on some of our most vulnerable qualities - like believing someone when you really do need the gig.

Look at it like this. Freelancers go to Upwork hoping you’ll hook up - translate - hire them. People go to Tinder hoping for love and relationships. In the end, people are seeking people for all sorts of reasons, whether its to pay the rent, feed the kids, or for a night out with a handsome stranger.

In the professional realm, these job sites provide clients an endless selection of freelancers in an endless supermarket of talent for hire. But, for the freelancer, the gig life can present an endless flow of indistinct, indefinite, vague commitments. In this hazy mist of situational convenience no one freelancer holds a job for long.

“I’m a disposable resource,” a friend of mine recently lamented. He’s a contract project manager at a startup that just went through a merger. He’s concluded that his skills are now redundant. He also feels ignored and excluded from the new team. Last week, he resigned in disgust.

“Working on the internet, I face this subtle slap in the face every day. I chose to work this way, and that means I have to accept the current state of affairs.”
— Contractor writer, single mother, currently undergoing chemotherapy treatments.

The Fastest Way To Ghost

So, when it comes to keeping your word in the gig economy, why talk when you can “swipe right” and “delete?” It’s an incredibly useful way out these days.

But, one thing seems to emerge. In the workaday world, where 35 percent of the American workforce are hustling two or three side gigs, (do workers really desire this over a steady paycheck?) the pervasive influence of social media platforms, texting, virtual meetings, and project management apps have eroded the very notion of the face-to-face, real gritty world, where honest-to-God people struggle with deeply felt emotions and messy complex lives.

Our digital life threatens to sanitize us to point of ethical vacuousness.

The realm of apps has facilitated a tendency toward moral shallowness. What was once considered bloodlessly cold and clinically disconnected is increasingly becoming the new normal.

For instance, a friend of mine, who is a gig writer at a start-up, recently mentioned that her predictable ten-hour per week workload has suddenly dried up. Curiously, there was no warning or heads-up from the CEO. Over the years, my friend has been loyal to the firm in spite of multiple unexpected pivots and management upheaval. Her current situation is especially acute as she is undergoing chemo treatments while trying to finesse her loss of income. Meanwhile, the CEO has shown remarkably little interest in her situation, and he fully knows she is a single mom juggling many demands.

What was once an unthinkable betrayal of loyalty in business, today allows us to ghost anyone as the situation dictates. Looking someone in the eye, especially when we have to break our word, takes more courage and integrity than blithely issuing an email or Slack message.

Has social media and texting made us more inclined to break our word?

In his Pulitzer Prize nominated book, “The Shallows,” David Carr asserts that human culture stands at a crossroads of cognitive “shallowing” brought on by the pernicious effects of technology, social media and always-on entertainment. The threat pertains to a potential decline in everyday reflective thought. Not since Gutenberg’s printing press, he writes, has the human race faced such a profound cultural and neurological consequence. We have no idea how we are being remade.

This isn’t about love, it’s about paying the rent. So keeping your word in this moment-to-moment, on-demand workplace, where a gig-hustling single mom is a paycheck away from homelessness, is arguably more important than ever.

On Writing & How I Can Help Your Business

This first blog article is inspired by setbacks. I'll spare you the details. Just know that certain things fell apart.

Maybe you’ve been there - the financial issues, the rejections, the arguments, even betrayal. At one point, I ended up in the hospital. The strain had taken a toll.

But, this is about writing, not about me. So, let's look at a piece by a writer who went through his own experience.

"I first met Dean not long after my wife and I split up. I had just gotten over a serious illness that I won’t bother to talk about, except that it had something to do with the miserably weary split-up and my feeling that everything was dead. With the coming of Dean Moriarty began the part of my life you could call my life on the road."

“On The Road," Jack Kerouac

I’m no Kerouac. And this blog doesn’t dare attempt the brilliance of his writing. But, we all have something in common with him: our origin story. Broader still, we all have a story to tell. And, it’s in the telling that makes the story sing - or fade.

These days, I ghostwrite for attorneys, creating their blog content, marketing collateral, and social media. Why? Because lawyers do law. Writers do writing.

My Purpose Could Help You - And Your Business

My purpose is to connect with you and to inform. In the long run, my goal is to provide you examples of excellent writing, while helping you understand the urgent need to use compelling writing in your marketing campaigns.

The Opening Paragraph Of “On The Road.” Why’s It So Great?

So, let’s take a quick look at Kerouac's opening paragraph to his masterpiece. It sounds sad, doesn't it? It's also terrifically crafted, and it informs us that the narrator has an important backstory. Because great storytellers provide context.

In this case, even though the backstory of "On The Road" is vague, it is specific enough to provide a glimpse into the narrator's motivation, which actually defines the way "On The Road" unfolds.

So, what does all this have to do with excellent writing?

Well, if you've ever tried to write your own blog, you might have started with a lot of enthusiasm. A month later, it's not as easy as you thought. Besides, there's a lot on your plate, and it involves running your business. The blog can wait, you reason.

And what about that email promotion to your customers? You have about two or three seconds to grab their attention. How do you do that?

Your greatest skills are running your business, not being a writer.

That's where I come in. I can engage readers who could be your next customers.

Stay tuned for more.

Thank you.