Oh, the Lengths We’ll Go: Extreme Stories on Getting the Job Done

Joshua Kraus
Joshua Kraus

A stressed dog handcuffed to his workstation

Freelancers, entrepreneurs, and other self-governing creatives may be the envy of their nine-to-five peers, but being your own boss can put a strain a different set of muscles.

With no one to manage your schedule and no co-workers to pick up the slack, these tetherless titans must sometimes go to extreme lengths in order to get things done.

Here are a few examples.

Eric Brantner

Eric Brantner

Role: Freelance Copywriter, Founder of Scribblrs

When launching my last site, Scribblrs.com, my team was waiting for me to provide the final piece of the puzzle. My job was to write the copy for our main landing pages. Everything else was there waiting, but I kept hitting my head against a wall. Not only that, other projects kept getting in the way.

Finally, it got so ridiculous that I needed to do something drastic. That’s when I went to my wife. I convinced her to agree that all sex would be cut off until I finished the copy. After all, that time with her is one of the most valuable things there is in my life. And dammit if it didn’t work like a charm. You better believe I fired out that copy within the next 24 hours.

Definitely appreciated my wife playing along with that one!

Melody Van De Graaff

Melody Van De Graaff

Role: Freelance Web Content Writer & Blogger

I have been working as a freelance web content writer since December 2015. Right when I started, I got mono, and had it for three weeks. This was right when I was starting to get samples and put my website together.

For those who haven’t had mono before, it is one of the most dreadful experiences. Everything hurts, but especially your armpits, which makes any sort of movement incredibly painful. Your body shuts down and you find yourself falling asleep doing the simplest things. Most people with mono sleep for 16–18 hours a day because their body is so exhausted.

But I made myself stay awake, even though I wanted to do nothing more than sleep. I practiced writing blog posts, reached out to my network, and starting forming relationships. I even did client work while I was ill.

I now have five clients and no longer have to work a real job. I’m continuing to build my business and get more clients.

Gillian Small

Gillian Small

Role: Owner of Gillian Small PR

I had to get an impacted wisdom tooth removed last November, but I had a conference call scheduled for a few hours after the appointment, so I couldn’t take any strong medicine during the process. Needing to distract myself from the impending pain, I decided to focus on catching up on my e-mails while sitting in the chair.

A few minutes into the drilling and hammering, I received a strong media lead, so I quickly typed out a client pitch—mid wisdom tooth extraction.

It all worked out. The writer bit on my pitch, my client was featured in the story a few days later, and I walked away with one less wisdom tooth.

Any passionate publicist would do the same … right!?

Ryan Robinson

Ryan Robinson

Role: Freelance Content Marketing Consultant

For the past couple of years, I’ve been taking on freelance writing clients on the side and spending a lot of my free time making sure I drive meaningful results for them. Most of my freelance clients have introduced me to other great new clients, and the good will has continued building from there. In conjunction with leveraging the content I create for my blog, I’ve been able to build my personal brand to a place where most new work comes to me, which was my ultimate goal.

All of this finally allowed me to quit my job last month, and launch into a freelance career where I’ll be making almost twice as much as what my full-time job paid me.

Now for the extreme part. For 3–4 days during each work week, I’ve gotten up at 4:15 am to start working on freelance client projects. Completing four hours of focused client work before heading into my day job has been absolutely crucial to my success as a freelancer.

When I first started taking on freelance clients, I would try working on their projects during the evenings and late nights, but I was already exhausted from a full work day, and I was starting to burn out big time.

Shifting my lifestyle so that I could get to bed between 9:00 pm and 10:00 pm every night allowed me to put in my best work for my clients before getting mentally exhausted from a full day’s work. If I had to point back to a single decision that’s had the biggest impact on my career, this would be it.

And if you’re wondering, here’s how I get up so early and stay awake. On the days when I’m up at 4:15 am, I use a FitBit vibration alarm to wake me up a bit more peacefully than the blaring iPhone alarm, which my girlfriend appreciates. I immediately get myself out of bed and don’t look at my phone (this takes conscious effort still) so that I don’t feel reactive at the start of my day.

I brush my teeth, shower, and have breakfast—usually two eggs. During breakfast, I’ll do a quick sort through my emails from overnight and prioritize what I’m going to work on in the hours before I get into my office. At 5:15 am, I bike about two miles to a coffee shop near my office in San Francisco, have a cup of coffee, and get to work on a freelance project.

Listening to music while I work is an essential part of my early morning routine, as it helps get me into the right mindset and stay mentally fresh. Right now the early morning tunes are mostly St. Lucia, Mayer Hawthorne, and Lord Huron.

Sebastien Dupéré

Sebastien Dupéré

Role: President & CEO of Dupray Steam Cleaners

When we were redoing our website, my development team was constantly getting held back because of my inability to get the content written. It was becoming such a problem that our lead developer wanted to quit because I wasn’t supporting him enough.

I solved this issue by getting my CFO to literally handcuff me to a desk in a private room in our office. The only way that he would let me loose was when I had written what we needed to write.

A few days later, I was pleasantly surprised at our progress, and I thought I didn’t actually need the handcuffs anymore. I was wrong. Long story short, my partner returned to “locking me up” again.

Jessica Mehta

Jessica Mehta

Role: Freelance Writer, Owner of MehtaFor

One hundred percent of my income is generated from writing, and some clients and projects are extremely demanding. I was facing a routine deadline two years ago while vacationing in Manhattan (working on vacations is the norm for me). Within a few hours, my arm had mysteriously doubled in size and a dark purple “snake-like rope” seemed to be growing and moving below the skin’s surface.

I was staying with a friend and took the subway to the ER while she was at work. After 13 hours in the ER with no doctor able to make any sort of guess, I demanded to know what the “worst case scenario is.” The attending doctor said, “Well, the WORST case is we’ll have to amputate your arm. But I’m going to try and avoid that.”

I was in the ICU for 72 hours before getting a diagnosis: cellulitis with unknown origins. It’s actually a rather common and easy “fix” if you can get it diagnosed, but can look terrifying. However, as soon as I was admitted (and still thinking amputation was on the table), I made my friend get my laptop from her apartment, bring it to the hospital, and I proceeded to finish all my deadlines, typing thousands of words with my less dominant hand. My right arm was full of IVs and so swollen and sore it was useless.

(Note: The client DID ask why the quality wasn’t as high as normal … I don’t think she believed me when I told her).