Why the Future of Work is Freelance

Closing the gap between personal and professional alignment

Imagine if we recorded a time-lapse of our relationship with work since the hunter-gatherer days.

It would reveal small spikes of change among a sea of plateaus. In 1817, Welsh manufacturer and labor rights activist Robert Owen coined the phrase “eight hours labor, eight hours recreation, eight hours rest.” Since then, not much had really changed.

Until now. A remote workforce, coupled with automation and a worldwide pandemic, is making us rethink the dynamic. Here’s how collaborating with freelancers gave me a glimpse into what to expect from the future of work.

Testing quick, failing fast, and moving on

Is this your first rodeo?

My roommate was the one who came up with the idea. After watching me spend countless weekends churning out newsletters for clients as a ghostwriter, he asked the question.

“Why not hire someone to help you so we can play more FIFA?”

It was time to make the leap and transition to an editorial role anyways. After all, this wasn’t my first rodeo — I had spent a few years managing others at a full-time job. But hiring on your own, as I quickly learned, was a beast of its own.

My first step was to tweak an old job description that my client gave me. Then, I prepared some thoughts on processes and compiled documents. Before I knew it, my mouse was clicking submit to post a job opening on Upwork.

Joe reached out with a proposal the very next day, along with a flood of unrelated requests. He seemed like the best fit based on his background. We jumped on a call, agreed to terms, and reviewed onboarding resources.

The next week, I received a deliverable in my inbox. It was missing key required sections and did not meet the level of quality I was looking for.

We discussed a prorated payment amount and quickly parted ways. That weekend sucked — I was still forced to write a draft, just to the tune of less money than usual.

“Failure does not matter. Success matters.” — Vinod Khosla

Let’s be honest, the first trial run felt like a setback. I was upset with Joe, then myself. Eventually, I realized that the chances of success on the first try were slim anyways. It was no one’s fault.

On the books, the excruciating journey was marked as a sunk cost. But underneath the surface was an important lesson. The experience provided clues on how to optimize my approach and prepare for the next opportunity.

Scaling and leaving room for good surprises

Not taking any chances this time.

The new goal was to find someone to work with long-term. At the same time, I didn’t want the application to feel too cumbersome or unwieldy. After being on the receiving end not too long ago, it just didn’t feel right.

Instead, I added two simple questions:

Describe a similar past project and the toughest obstacles you faced
Tell us more about yourself and why you want to work with us

Now it was time to play the waiting game. A week went by at a snail’s pace, without a single application in my inbox. I started to worry and wonder if finding other writers in this specific niche was a losing proposition.

Jess made it clear that was not the case. At five o’clock sharp, a notification popped up on my phone. It was attached to a well-crafted proposal with project samples and customer testimonials.

We got on a call the next week. The rest was history.

She came prepared with ideas, questions, and a plan. We worked together to iron out the details. By the next week, the project was on autopilot. She would send drafts on Wednesdays — I’d review and ship a final product to the client by Mondays. Like clockwork.

This continued for two more years until the client decided to bring some of the work in-house during the pandemic. However, this wasn’t the end of our partnership. Just a few months ago, someone found me through a referral and dialed for help.

Guess who my next call was with?

“If you don’t leave room for the unexpected to express itself in your life, you close yourself off from the possibility of miracles.” — Robert Stimanz

Instead of clamping down on years of experience or generalizing the job description, I tried to double down on what matters. Top talent that would be fun to work with. By shifting from a transactional to relational mindset and leaving room for surprise, an unexpectedly great teammate emerged.

Two simple questions made all the difference.

Getting creative with talent development

We don’t have much money, but we have…cool projects?

Jen and Pat were the next two “hires”. We created a website and ran marketing for an artist promoting his new album. Eventually, the project came to a halt, and so did the funds and excuses to spend time together.

But why did it have to be this way?

To keep the momentum going, my mind began conjuring up ways for us to collaborate. We started having coffee chats, taking on odd side gigs and jobs together, and brainstorming topics to write on Medium.

“In learning you will teach, in teaching you will learn.” — Phil Collins

Where I had experience, they had creativity. Where they were experienced, I could source clients and funds so we could build together sustainably.

Some of the projects were not new to me, whether it was running a small paid search campaign, designing a website, or conducting media outreach. But there was magic in learning from others, and humility gained in fumbling over words when trying to teach.

Establishing belief systems

We went from hunter-gatherers to farmers, then industrial workers. Today, many of us are digital natives engaged in knowledge work. The future is here.

Remote and on-demand, yes.

But also in dire need of personal and professional alignment. The gig economy offers clues into how employers and employees can search for such aligned incentives.

Akin to agrarian societies of the past, delayed gratification, teamwork, and growth mindsets that think in abundance are likely to pay off.