Being independently employed has many benefits. For one, you get to set your own hours, which is incredibly handy if you are passionate about writing or any other art. There are pits found on the dark side of contracting, though. If you’re not careful, you’ll fall into one and collide into the icy water below.

Welcome To Another Edition of Unprocessed Thoughts

For this month’s unprocessed thoughts, we’re looking at the dark side of contracting, which applies to small business owners too. I’ve been freelancing full-time since 2014 in the graphic design and web development industries. I would be lying to you if I said there haven’t been significant downers with the benefits of flexibility.

With freelancing, we commonly hear it’s about “lifestyle” or “being your own boss” or “embracing hustle culture,” and my favourite, “do what you love, and you’ll never work a day in your life.” There’s some truth to these generalized statements, but they’re too broad of a stroke. We don’t hear about the dark side of contracting because there’s nothing sexy about hearing bad news.

As mentioned, you can set your own hours. You can also set your rate, decide to take on a project or not. The elasticity is immense. It also benefits companies to seek out freelancers opposed to hiring an employee.

Benefits for The Company

Businesses today are hiring contractors for specific skills on a project-to-project basis. It is cheaper in the long run than hiring someone and worrying about human resources, healthcare, employment liability, etc.

If a business sources niche skills for specific jobs, they drastically cut costs, finding these freelancers in their own network or from a gig site like Fiverr. Discussing quality and cost is another topic, especially with gig sites.

I’ve had colleagues warn me about these gig sites in the past. They have said there’s cheaper competition out there. These gig sites have never impacted my work because I maintain happy clients through top-notch work and transparency.

This is great for a company, but what does that have to do with the dark side of contracting? Well, for starters, let’s look at what it’s like to be on the flip side of the company.

Contractors Need Thick Skins and a Sturdy Backbone

Some companies are intentionally malicious by squeezing out every bit of drop they can from their workers, contracted or employed, while others are oblivious to the actual work involved. Leads may attempt to haggle the contractor’s price down too, and freelancers fall for this. At times, contractors don’t have the confidence to properly negotiate the terms of the agreement. They can spend many hours and do additional work on a project beyond the original scope and quote.

To avoid this dark side of contracting, one must maintain a thick skin and a sturdy backbone to ensure a project doesn’t derail from the original conditions. This keeps everyone is happy with the results. Of course, there are times you just can’t please specific clients.

Politics and Bullies

You would be surprised to learn that office politics don’t stay in the employment realm. There are plenty of politics that can be found when freelancing. Projects can mutate due to the internal politics of your client’s company which will alter how your work is done. Or you’ll have some clients you have to tread lightly with due to their personalities.

Bullies don’t just appear in the playground. They follow us well into adulthood and morph into politics where egos and pride play critical roles. People try to secure their importance within a company to prove their value which can affect you as the contractor if they push you around for their own benefit.

Opposite of a sturdy backbone, stay flexible enough to work with unforeseen circumstances because no one has a crystal ball. Be sturdy enough to know when to stand your ground and flexible enough to adapt.

Here is a quote from Bruce Lee, which you’ve likely heard, that is more poetic:

“Be like water making its way through cracks. Do not be assertive, but adjust to the object, and you shall find a way around or through it. If nothing within you stays rigid, outward things will disclose themselves.

Empty your mind, be formless. Shapeless, like water. If you put water into a cup, it becomes the cup. You put water into a bottle and it becomes the bottle. You put it in a teapot, it becomes the teapot. Now, water can flow or it can crash. Be water, my friend.”

― Bruce Lee

I’ve been quite fortunate to have a consistent client base and have rarely run into the two topics mentioned above. They do exist, and like any contractor who has been in the business long enough, I have had my run-in with them. Thankfully they don’t last long, and we part ways.

These aren’t the only pits on the dark side of contracting. Cash is king, and with freelancing, there are challenges with it.

Getting Paid

This is the second biggest pit in the dark side of contracting. Unlike employment, freelancers are required to fetch the money themselves. And it’s up to you to follow up when you need to get paid.

There are many reasons why clients are late or never pay. Here are some scenarios:

  • Their accounting team has changed, and your invoice gets lost.
  • The person you’re working with has quit or been fired, and no one knows about your project, and it dissolves.
  • They do not have the money to pay you and are avoiding it.
  • They don’t ‘feel’ the work is worth paying anymore.
  • They forget.

Believe it or not, clients forgetting is the most common reason why you’re unlikely to get paid. Do the best you can to keep them pleased, and they’ll be keen on paying you quicker.

As a freelancer, keep track of all the invoices you send out, split by the month, to ensure that you are on top of all the work you did and the money owed to you. Speaking of keeping track of things, this leads us to our next section.

Biting Off More Than You Can Chew

Contractors supply quotes for projects. On the dark side of contracting, this pit is supplying too many quotes, and they are all approved. This can occur from submitting RFPs, too many client referrals, or an influx of projects from existing clients. Even if you can negotiate timelines and the pay is good, sometimes there is too much work for you to deal with on your own.

There are ways of handling too many projects, such as:

Subcontract Someone You Trust

As a freelancer, you should develop a professional network of colleagues you can rely on hiring if you have too much work or team up with more significant projects. With subcontracting, you can tax a project management fee as well.

Pass The Work to a Colleague

You may have no time to play project manager and want to entirely remove the project. This is another reason why keeping professional relationships within your industry is helpful.

Negotiate Time or Throw Your Hands Up

Try to negotiate an extended timeline. Perhaps the timeline is too tight, or you have no colleagues to pass the client onto. Worst case, you can tell them you can’t help them and pass on quoting. In the end, they’re not your boss. They’re your client. Careful, though. You can burn bridges this way.

Even Then . . .

There are times when you simply can’t do any of the above and have too much work. Maybe you need the money or none of the other options available to you, and you must do all of the projects. In this case, you will be working many hours and long days. Your quality of work will degrade because it’s inhuman to work long weeks. We’re not designed to be production machines.

There’s more to life than simply working, and it’s important to remember that as a freelancer because we can get lost in our own heads. This leads us to the final and most giant pit.

Personal Life Suffers

This is the enormous pit on the dark side of contracting. Not having thick skin with a sturdy backbone will put stress on you. It increases the chance of not getting paid, leading to politics and bullies or biting off more than you can chew. These pits will cause a decline in your health and quality of life.

Make sure you set clear boundaries, realistic pricing for your skills, and stick to timelines while doing excellent work. It’s the best way to avoid any of these pits. If you do fall in one of these pits, you can climb out of them.

Personal Experience

Here’s a short example of some of the above that we’ve discussed: All of 2022, I have bitten off more than I can chew. Since January, I have worked 70 hours a week, Sunday through Friday. It made me scattered, lose track of project details, reduced my quality of work, and impacted my personal life. Amazingly enough, I’ve still been writing short stories on Patreon and am near completion for my next book release.

No one is to blame for my scenario. It was an accumulation of many things, from timelines bleeding over, scopes mutating, an influx of new projects, and the world opening back up again after two years of a pandemic.

Life is Beyond Control

We all make mistakes and end up making rookie moves which are embarrassing when we are seasoned in our line of work. You can’t predict unforeseen circumstances in business, such as timeline extensions for the client, being paid, scope mutations, personal tragedies, etc. You can do everything right to the best of your abilities, and the universe will go completely against you.

Freelancing adds another layer to the complexity of life’s random nature. Steady and reliable work tends to be for people employed by the government, while freelancing is everything opposite of that. It has many benefits, but you can still fall into the pits on the dark side of contracting.

There are other holes here, too, which we haven’t covered. Here’s a short list of some:

  • Managing the admin business paperwork and messing it up.
  • Accounting. Unless you’re an accountant, I’d highly recommend hiring someone for that.
  • Additional expenses like healthcare and tools.
  • Holidays and sick days equal no pay (no work, no invoice).
  • Office space.
  • You set the labour standards.

As a contractor, the best way to stay clear of the pits is to be lean, vigilant, and remember your humanity. Business is cutthroat, and it is easy to forget who we are. Before you know it, you’ll fall to the bottom of one of these pits and be swallowed up in the icy waters. What was once human will become a shark, preying on others who fall into the dark side of contracting.

Beer Note: The Est. Brave Noise Pale Ale

The Dark Side of Contracting Beer Note: The Est. Brave Noise Pale Ale. Unprocessed Thoughts March 2022

I tried the Est. ‘s Brave Noise Pale for this month’s Unprocessed Thoughts, a 4 .5% alcohol volume. The beer comes in a four-pack set. It’s a little hazier than I usually like, but I enjoy its lightness compared to some beers claiming to be pale ales and are usually IPAs. These go down easy, and it is worth having a few if you’re not drowning in the ocean of work.


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Konn Lavery

About Konn Lavery

Konn Lavery is a Canadian author whose work has been recognized by Edmonton’s top five bestseller charts and by reviewers such as Readers’ Favorite, and Literary Titan.

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