I Kept a Client for Two Years. It Was A Terrible Mistake.

When I first launched into freelancing about five years ago, I did so under the auspices – some might say romance – of the literal and historic origins of the term. The story goes that the word “freelance” comes to us from back when battles were fought with swords and shields. The “free lance” was a skilled soldier not bound to any king or lord. Rather, his services were available to the highest bidder. He would fight for whoever was paying him until the work was done, collect his coin, and move on.

For someone who had reached the end of his rope with the monotony of day-to-day corporate life, the freelance life was incredibly appealing to me; especially when I could talk about it using those kinds of words and ideas. Sure, I would need to define a skillset that allowed me to achieve the necessary level of authority to earn the freedom and independence I so desired in my work. But once I had created something that was viable and marketable, the notion of going into a situation, fixing it, and moving on to the next challenge was about as close to an ideal way of making money as I could imagine.

“Maintenance” would cease to be a part of my vocabulary. “Status quo” would be for everyone else. Settling in, getting comfortable, and plodding through the day-to-day would be for those who hadn’t been asked to resolve something the company was otherwise unable to resolve on its own.

After all, if they could, I wouldn’t be there.

This is how things went for the first few years of my endeavor. I’ve had the pleasure of working with clients around the world to overcome a wide variety of issues. I’ve elevated businesses and their leaders. I’ve helped to secure millions in investment and even more than that in revenue. I had successfully become the person working behind the scenes that no one knows about – the one who goes in unseen, affects the necessary change, collects my coin for a job well done, and moves on to the next battle.

And then they entered my life. For confidentiality reasons, I obviously can’t discuss who they are. For readability reasons, we’ll call them The Client.

The Client initially contacted me with a very specific set of needs. They had launched a new initiative, and the very nature of that initiative meant that someone had to handle it from the outside. This was very much a “come in and shake some shit up” kind of engagement – one of my favorite kinds. There was internal resistance, there was conflict, there was everything you’d expect to see when you’re trying to get a cruise ship to change direction with the agility of a jet ski.

I’d be lying if I denied that it was ridiculously fun. And, even better, it worked. Our mission succeeded and I was asked to do the same thing for a couple of other projects The Client had in the works. Failing to see the harm and enjoying the longer-term stability of a client that had a lot of work to be done and paid on time (otherwise known as hitting the freelancing jackpot), I accepted.

Anyway, after a while I finished those jobs, got paid for my efforts, virtually shook hands with my former employer, and walked away in search of my next temporary king.

See, that’s how this story should have ended. But it’s not. In reality, I became a de facto employee of The Client, allowed myself to become integrated into a full-time team and organizational structure, attended a multitude of meetings where I quite literally never said a word, took my orders, and woke up day after day feeling like I…had a job.

Mind you, this was not an “oh look, I have a new contract job to do” kind of feeling. No, I had a full-on job. A “roll out of bed in the morning and get ready for another day at the office” kind of job. The kind of job where the only thing missing was forced office birthday celebrations and a hellish commute either stuck in traffic or stuffed into a subway car with no option but to endure other people’s music through their shittily-fitting ear buds; a fate I was spared only because I worked from home.

The machine that fueled the maintenance of the status quo and squashed anything that tried to shake it up began firing on all cylinders once again within The Client’s walls, and I went from being an intentional wrench in the works to just another cog. I was no longer expected to fight and challenge and change. My role was now to shut up, get in line, and do what I was told.

This post, however, is not an indictment of The Client.

Quite the opposite really. I’ve written this post to indict myself. I’m indicting myself on charges of complacency, laziness, and greed and I’ve already found myself guilty on all counts. But, like the criminal who apologizes not out of remorse for their actions but out of remorse for getting caught, I must now also repent.

The Client paid well. They paid on time. The work was simple and the money was easy and they were willing to continue sending me barrels of cash in return for a minimal emotional or intellectual investment, so what kind of moron would I be to walk away from what others would say was the perfect work situation?

The simple fact of the matter is that I kept this particular relationship going for far longer than I should have because I sold out. I traded my soul for a paycheck and I abandoned the very thing that made me start doing what I do in the first place: my desire to use words to create opportunities for my clients and help them exploit those opportunities for everything they’re worth.

It was clear that my help in that context was no longer needed by The Client for quite some time. I knew it and they knew it. In the context of creating change and opportunities, my assistance wasn’t even wanted by the end. As time between contacts dwindled, drama reached a crescendo, and the river of tasks that was once swollen to its very limits dried up, I finally did what I should have done so long ago and formally terminated the relationship.

Having had some time to process, analyze, and learn from all of this, I’ve resolved to apply the experience’s lessons to my business from this point forward. I’m sharing them here for anyone else who might find themselves in the same situation.

First, I will never promise and/or dedicate all of my available bandwidth to a single client. That was one of the first things I did for The Client and I did it because of how much work they were promising. They also had limited experience working with a freelancer and I wanted to allay any fears they might have of my departure before getting it done. While I may have promised to forsake all others when marrying my wife, I’ll never do it for a client again.

Second, I now understand the power of recognizing the feeling of “this isn’t why I started doing this.” Frankly, if you’re in business for yourself and you’re not enjoying executing on that business, then why the hell are you doing it?

If I ever have to work with a client in a way that makes me wonder why I rolled out of bed that morning, then I will cease doing business with that client. Sure, there will be highs and lows. But when the lows start trouncing the highs, it’s time to walk away.

Third, I will never again compromise my business and professional needs for a paycheck. Was it nice not having to wonder about the next deposit into the bank account for a while? Absolutely. And, my time with The Client happened to coincide with a very expensive long-distance move. Having The Client’s money as a steady source of income did wonders to help pay for that move.

But the truth is that things with The Client should have ended long before the move even became a factor. Had I severed ties and moved on when I should have, The Client would have been a memory and “just another client success story” instead of a vivid example of what happens when you keep a relationship going long after its expiration date has come to pass, and the subsequent blog post about it.

As freelancers, we are in business to accomplish our tasks, collect our payment for achieving our employers’ goals, and move on to the next kingdom that requires our assistance (and is willing to pay our price for it). It is a key principle of doing what we do for a living.

I forgot that for a while, but I assure you I’ll never forget it again.

How (not) to Write a Job Listing on Upwork

Contrary to the view of many freelancers, I believe that sites like Upwork can be very helpful in introducing a freelancer to a market that he or she may not have otherwise had access to.

Now, does Upwork have its problems? Absofuckinglutely. But there are also benefits to the platform, particularly when talking about the new freelancer. A new freelancer who might be testing the waters or working on building their business during nights and weekends is not going to be able to invest the time and effort necessary during normal business hours. Having access to a global marketplace full of people looking for particular skill sets can make a tremendous difference – especially when that marketplace is open 24 hours a day, 7 days a week.

At the same time, the freelancer who already has a steady book of clients and no issues finding new work may use these platforms on occasion to simply see what else is out there. Networking, referrals, and other methods for finding, and keeping, work certainly have their place. But, frankly, there is nothing wrong with opening the laptop every so often and just taking a peek at what is available. You may find a dream client that wanted to give using freelancers a try and that was the only way they knew how at the time.

The flip side of this, however, is the employers’ side. Spend enough time looking through various job postings on freelance marketplaces and you’ll see posts that run quite the gamut. And, it will become painfully obvious that some employers, quite honestly, just have no idea what it’s like to work with a freelancer. They insist on applying classic business principles and ideas to a non-traditional method of getting work done.

To help resolve this quandary, I’ve created a short list of dos and don’ts for you to follow the next time you decide to wade into the freelance pool in search of the right person to get your project completed.

Do state the actual task in the listing. If you are looking for someone to write content for your website about growing catnip, then state that you are looking for someone to write content for your website about growing catnip.

As such, don’t be vague. “I need someone to write content” is a brilliant statement of the obvious – you wouldn’t be posting a job if you didn’t need someone to write content for you. The question is what kind content do you need written? Does it fall within my skills, abilities, and interests?

If I don’t have the answers to those questions I won’t know if we can work well together and I’m not going to apply to your posting. Instead, I’m going to invest my time in reaching out to posters who clearly state their needs because I’ll know, from the start, that I can make an impact on their business.

Do understand that you are hiring a freelancer and not a full-time employee. The freelancer who views your post may be working with one, two, or ten other clients at that particular moment. Regardless of the number, however, the freelancer operates in this arena because they do not want to be an employee.

I saw a job listing a while back that stated that the freelancer needed to be available on Skype for all 9 hours of the business day. They were required to attend every morning meeting and afternoon wrap-up. Tardiness to these meetings would result in immediate dismissal. Repeated failures to answer Skype messages would result in immediate dismissal. Taking too long to respond to an email would result in immediate dismissal.

Not only is that a company that I would never freelance for, it is a company that I would never work for. Don’t lose sight of the fact that you are hiring a freelancer to solve a specific problem for you. Our days can be incredibly varied. Some days may mean that I’m at my desk from the time I wake up to the time I realize that I haven’t eaten yet and my cats want dinner. Other days, I may have errands to run or want to get out of the house for a while and go for a bike ride or a hike.

If you want to know the key to working with a freelancer it is this: Give me a task and tell me when you need it completed. Understand, however, that how that task gets completed will be left up to me.

Don’t be grandiose in your posting. “We are only looking for the very best. If you’re not the best, don’t even bother applying. If you’re mediocre, we don’t want you. We’re the best and we only work with the best.”

Oh just stop.

The reason that you’re not hearing from people on posts like this isn’t because there’s a limited amount of talent available – it’s because those of us who are good at what we do have no desire to work with someone who would make this their introduction.

Don’t ever ask for free work. Look, I get it. There are a lot of bad freelancers out there. And, there are a lot of people out there calling themselves freelancers who are basically just trying to turn a quick buck at your expense.

But asking for free work as a trial is not how get around this problem.

As a freelance writer, I have no shortage of work that I can present to you as an example of what I am capable of. They are called writing samples and every one of us has them. I will gladly go through my writing samples and I will find something that presents my skills in a way that shows whether I am a match for you or not. If you want something that shows my ability to research, ask for a sample that involved a lot of research. If you want something that shows my ability to evoke emotions, ask for something that I wrote for that purpose.

But, my time, and my skill set, is valuable. Producing free work for you in hopes of getting your job is simply not an option.

Do be responsive. If a freelancer that you are interested in gets in touch with you, provide them the courtesy of a timely reply. It will show that you value their potential impact and that you are serious about the work you need done. It will also increase the possibility of you booking that freelancer before they find work elsewhere. If you found their reply to your post appealing, odds are that a few other companies did as well. The odds that they replied only to you in their last search session are incredibly low.

Lastly, don’t forget that you get what you pay for. If you’re a bargain-basement client looking for 2000 words for 10 dollars, then understand the caliber of work you are setting yourself up to receive. If you want quality, then you’re going to have to be willing to pay for it.

Hiring a freelancer is not the journey into the unknown that you think it is. By understanding just a few key differences, you can increase the odds of setting a relationship in place that will pay for itself tenfold, for you and for the freelancer. And, when both sides are happy with their arrangement, amazing things can happen.

The Folly of False Feedback

“Criticism may not be agreeable, but it is necessary. It fulfils the same function as pain in the human body. It calls attention to an unhealthy state of things.”

Winston Churchill

I’ve been part of quite a few freelancing groups online. They’ve been based mostly on Facebook and they’re the kinds of groups that revolve around some blogger’s ability to have created a community around her- or himself.

You know the types – read the site, sign up for a newsletter or two, and then BLAM – join my private Facebook group (like there’s actually some barrier to entry) to get even more information and meet other like-minded entrepreneurs. We can all celebrate the awesomeness of our lives together!!

I quickly realized that I’m not cut out for these groups. They’re too….touchy-feely. They exist solely to prop people up when, in reality, a lot of the people involved need reality checks more than they need support. When you’re a “writer” and you post a link to one of your typo-ridden blog posts for circulation and no one calls attention to its shortcomings for fear of “tearing you down,” well, that’s a problem. (like this last sentence…holy run-on, right??)

Yet comment after comment in these groups is the same:

“Oh, this is great!”
“I really needed to read this today! Thanks!”
“Sooooo good!!”

and, my personal favorite….

“OMG – totally adding this to my Buffer.”

OMG, kill me.

In reality, the comments should go something like:

“Decent start, but your sentence structure needs a little work…keep going!”
“I got a little lost on the point you were making in the third paragraph. Otherwise, it’s a great start and I’m looking forward to seeing the finished version!”
“D’oh! There’s a typo in the second paragraph. Fix that, re-work the fourth sentence in the fifth paragraph, and fix that big block of text in the middle of the page. But you’re on to something!”

Ok, so by now you’re probably asking if I’m in a particularly bad mood as I write this. Truth be told, I might be feeling a bit snarky. But that doesn’t negate a very important fact of life and the thread that will run through today’s post. And that is…..

People don’t learn unless they are criticized.

Tell someone that they’re good at something when they’re not and they will continue to do that thing badly. You haven’t propped them up – you’ve done them an incredible disservice.

Now, I understand when friends do this for other friends. I operated as a professional photographer a few years ago and, like most people with a camera, I loved taking pictures and sharing them with my circle. The feedback was always amazing:

“Sooooo good!!”
“WOW!! Absolutely gorgeous!”
“Love this!!”
“Beautiful pictures, Eric!”

Admittedly, this was great for the ego. But, I was also self-aware enough to wonder if the same feedback would be possible from complete strangers. And, sure enough, it wasn’t until I sought the advice and criticism from those who didn’t actually know me that I started to get better at my craft. It would take years of this particular kind of growth before I would have the audacity to charge for my work.

The same thing has happened with writing. I’ve shared a few pieces with friends along the way. They were, of course, very supportive. But it wasn’t until I started putting my words in the public eye and seeking out true criticism that I started discovering the things that I really needed to improve upon. Because, guess what…there actually were faults in the writing. There were cracks and there were things that needed my attention. Hell, there were full-on holes. There was massive room for improvement.

This is what puzzled me about these Facebook groups. These are people who don’t technically know each other. They’re not friends, per se. They are merely people united under the common flag of having started working as freelancers. They are looking for some sort of common bond to share with others. They are looking to learn, to grow, and to make themselves better and give themselves a better chance at success.

So, why do they decide to spend that time lying to each other??

Here’s what happens in a situation like that.

Our freelancer in question posts blog post after blog post to their group. Week after week, they post their little “tidbits” and life stories and week after week they’re told how good their posts are. Never mind that it’s work that probably wouldn’t make it past a 7th grade English teacher. No, we’re going to keep telling our freelancer that their posts are great and we’re going to comment on them and maybe even share them with others.

Then the freelancer decides to go after a job. Propped up by months of positive feedback for mediocre work, the freelancer confidently goes after a job, somehow gets a win – probably based on personality – and starts working.

Two weeks later, the client is livid.

The work is mostly unusable and will require the client to go find another freelancer to fix it – spending even more money because they are now effectively having to buy this work twice.

The freelancer is crushed. Literally….crushed. They have no idea what just happened. Every single word they’ve ever heard about anything they’ve ever produced, even from the strangers in their Facebook groups, has been positive. But, when it came down what matters, they failed miserably.

So what was the difference? What was that thing that mattered? It’s simple.


Clients expect value for the money they are giving in exchange for your work. They are enriching you financially so they damn well better be getting something in return. They’re not paying you in feedback or in slots in their Buffer queue. They’re paying you with cash. Legal currency that could do just as much for them as it can do for you.

Keep that in mind when you’re feeling like stepping outside of the guarded walls of your positive feedback loop. Seek out critical eyes that have no problem telling you that your work is just ok.

Opportunities to improve are everywhere – even in the places we don’t want to look.

Freelancing Might Not Be for You…And That’s Ok

I read a post by Salon’s Steven Hill the other day that got me thinking. The title?

The Uber-economy Fucks Us All: How ‘Permalancers’ and ‘Sharer’ Gigs Gut the Middle Class.

As a permanent full-time freelancer and a member of the middle class, I desperately wanted to know how my job, and the jobs of over one-third of the US workforce, was killing the country’s economy.

The title alone probably should have given me pause before clicking. First of all – he said ‘fuck.’ If this was going to be some sort of brainy academic analysis of the economic costs and benefits of this new way of working, then I think…well…I think that would have been the title. “A Brainy Academic Analysis of the Economic Costs and Benefits of Permalancing and Sharing Gigs, by Salon’s Steven Hill.”

Alas, it was not meant to be.

No, this was going to be an angry post full of angry words written by an angry man. And, sure enough, the first thing you see when the page comes up is an angry picture of a very angry Donald Trump.

Oh boy.

And so we begin with the first sentence:

A significant factor in the decline of the quality of jobs in the United States has been employers’ increasing reliance on “non-regular” employees — a growing army of freelancers, temps, contractors, part-timers, day laborers, micro-entrepreneurs, gig-preneurs, solo-preneurs, contingent labor, perma-lancers and perma-temps.

Hill goes on, over the course of the next 1200 words, to detail a laundry list of complaints that he has with this new reliance on non-W2 workers:

  • Companies aren’t responsible for contractor’s benefits, retirement, sick leave, vacation time, or any of the other perks that come with full-time employment.
  • It breaks the agreement that corporations made with workers during the New Deal, creating a dystopian world of “on-again, off-again” employees.
  • You only get paid for the work you’re actually doing. Mr. Hill no longer gets paid to go to the bathroom or chat at the water cooler, and this was a big enough problem for him that he included it as a complaint in his post.
  • You have to track multiple income streams and exert effort to make sure that you get paid for the work you do.

The list goes on and on. The “1099’ed” economy means the end of the “good jobs that have supported American families,” the end of the middle class, and the start of the decline of the United States as a world leader.

Oh please.

While I understand that most of his anger is directed at the companies that have triggered this shift and not so much with the people who now live and work it, I still have to ask a fairly basic question:

Mr. Hill, could it be that freelancing just isn’t for you?

And couldn’t you be ok with that rather than condemning the choice that millions of Americans have made in their method of work and “the sky is falling” your way to the end of American civilization as we know it?

Hill wrote his post as the result of having been laid off. And believe me; I understand the anger that comes with a layoff. When I was working in the technology industry I was laid off twice in less than a year. Both jobs were outstanding opportunities that evaporated because…well…what good does it do to try to place blame at this point. Business is business and the choices that businesses make have consequences for their employees. Anyone who has held a job in the past decade can attest to that.

But, in his anger, Hill has made some assertions about life in this freelanced economy that I, and those like me, have to take issue with.

I voluntarily left full-time employment to work for myself and become a full-time freelancer. I wasn’t forced out. It wasn’t a “resign or be fired” situation. No, my desk was empty the day after my final two week notice because I chose not to go back.

And, honestly, I don’t know what it would take to get me to go back to that life. Everything that Mr. Hill abhors about the freelance life is something that I adore because it has made me infinitely better at what I do.

I’m the person that gets called when companies don’t have someone on staff that can solve their problem. Every dollar I make is made because I’ve added value to a situation that required my assistance in order for it to become successful. While companies and corporations lumber their way through their day to day operations, carrying their full-timers on their backs and paying for their best and their worst work, I have to create value 100% of the time or my clients will find someone else who can.

Subsequently, I’m able to charge for the value I provide, and my services are not cheap. However, as if following the tired “they’re taking our jobs!” battlecry to a T, Hill focuses his attention and energy on the lost income and “race to the bottom” aspects of freelance income generation. Try hard enough and you can actually see the same arguments used by the anti-immigrant community creep into Hill’s anti-freelance sentiment.

“Those with money,” he says, “will be able to use faceless, anonymous interactions via brokerage websites and mobile apps to hire those without money by forcing an online bidding war to see who will charge the least for their labor, or to rent out their home, their car, or their personal property.”

And later…

“Indeed, the so-called “new” economy looks an awful lot like the old, pre-New Deal economy – with “jobs” amounting to a series of low-paid micro-gigs and piece work, offering little empowerment for average workers, families or communities.”

For freelancers who focus on providing value to their clients and ensuring that they are functioning as valued members of their clients’ teams, this “race to the bottom” is a figment of the imagination. It doesn’t exist. We don’t compete in that space.

Having properly executed my plans, my freelance income levels are well above anything I ever made as a full-time employee of any one company. See, while Mr. Hill complains about not being paid for time not spent working, I spend my time figuring out how to become more valuable to my clients. Rather than talking about the weather while I wait for the Lean Cuisine that I pulled out of a disgusting shared freezer to finish microwaving, I’m figuring out new ways to make my clients successful.

I compete on value – not on price. And, as a result, I have been repeatedly tasked with “fixing” work that other, low-priced bargain basement freelancers screwed up. At times, I’ve been able to do things that a company’s full-timers simply couldn’t make happen. Why?

Because changing course on a jet ski is a hell of a lot of easier than turning a cruise ship.

And I’ve done this while enjoying all kinds of benefits.

While I don’t have sick leave or paid vacation time, I work when and where I want to work at times that are convenient for both me and my wife, who also happens to work a non-traditional schedule. As a result, we see each other more than we could dream of if I was forced into a standard 9 to 5.

I’ve set my own rate as a function of the value I provide to the clients that I work with, rather than laying down at my full-time employer’s feet and hoping that they can find it in their heart to give me a cost of living increase for the year…a function of inflation and economic conditions; not my organizational contribution or value.

I pick and choose the projects I want to work on. If I don’t feel a task or an employer is a good fit, I simply decline it.

I am talent for hire and my skills and abilities go to the highest bidder, not the lowest. I am the most professionally empowered that I have ever been.

And what do I give in return for all of this? I have to work to find jobs to fill gaps when I’m not working with my regular, repeat clients and, no, I don’t get paid for that time. I have to pay more in taxes and track the finances of my business rather than just checking to make sure that my direct deposit went through every two weeks. I have to be “on” 100% of the time. And, I have to constantly question and take inventory of whether my business is moving in the direction I envisioned when I started it.

If Mr. Hill ever found another full-time job, and I hope he did given how long ago the post was written, then I wish him the best in it. But that world is no longer for me and millions of people like me. We understand that corporate loyalty died with our grandparents and the freelancing economy is simply that death taken to its logical conclusion as seen from the workers’ side.

The wonderful thing that no one could have ever seen coming, however, is that we don’t need the full-time employment of those corporations and companies and the bullshit that comes with it. Rather than completely surrendering to a fate over which we have no control, we’ve chosen to seize the opportunity presented by living in this era and become our own businesses. Technology allows us to enjoy freedoms that we never could have considered while under the thumb of a W2. I don’t need an office park, a cubicle, casual Fridays, and an office manager tracking whether I’m two minutes late through the door in the morning.

I need my laptop or iPad, some wifi, and a decent cup of coffee.

My life is far from dystopian, Mr. Hill. In fact, it’s the closest I’ve been to Utopia in my entire professional existence.