The Ultimate Guide to Winning in the Gig Economy

Oh the joys of gig working in your local sunny cafe. Credit: Bonnie Kittle

Spare me the hype about the ‘awesome new gig economy’ and how it’s ‘disrupting employment’ while creating ‘the new future of work.’ It’s certainly nothing new. Not too long ago we called it being self-employed. Only three things have changed in the self-employed space in the last twenty years:

  • Large-scale global unemployment means there are more previously-employed people making their skills available as self-employed, independent workers;
  • An entire generation of millennials have decided (for good reason) that the old model of working 9-to-5 in an office needs a revamp;
  • We now have platforms that more effectively connect service providers with buyers.

Admittedly, these are significant shifts, so let me demystify and demythify what it takes to remain valuable and indispensable as an on-demand professional in a rapidly changing world — assuming, of course, that demand for your skills and expertise is already high.

If you compare this whole ‘gig thing’ to skiing, you can choose to be either a novice who ambles down red slopes, a professional who takes on black slopes with ease or an extreme skier who has perfected their art to become one of the top 1%.

Let’s dive into what it takes to be a ‘1% gigster.’

According to an October 2016 McKinsey study, there are 162 million independent workers in the United States and Europe alone. With so much competition, the reality is that making it big in the on-demand economy — earning a consistent flow of income that exceeds your salaried earning potential — is nowhere near as easy as many proponents of the gig economy claim it is. But it is doable. If you’re serious about making it as an independent worker, it will take more than simply registering on sites like Fiverr, TaskRabbit and Elance (now called Upwork) to work 80-hour weeks on low-paying, infrequent and unpredictable gigs. The key is to find high-paying, strategic pockets of work that you and you alone can do because you’re the best in the world at it.

Do high-paying, strategic, independent assignments exist?

Absolutely, yes.

Fortune 500 organizations and well-funded tech startups alike have realized that on-demand or contract hiring is a more effective way of getting project-based work done. This method of work allocation allows them to be leaner and more responsive to market forces. They have found that their on-demand workforces are more motivated and engaged than their salaried counterparts. Computer science professor Cal Newport has identified the reason independent workers are more motivated than empoloyees in his book Deep Work:

“To build your working life around the experience of flow produced by deep work is a proven path to deep satisfaction.” — Cal Newport, Deep Work

Employees are simply too distracted by administrative interruptions, office politics and endless meetings. Flow simply cannot flourish in the office.

Research backs up the rapidly rising use of independent workers in corporations. A 2016 WorkMarket survey found that 27 million people form part of the corporate on-demand economy and 56% of executives surveyed said they planned to increase their use of on-demand professionals.

To download the full report, visit WorkMarket.

Deloitte’s concurred in their 2016 Global Human Capital Trends analysis, revealing that 51 percent of the executives surveyed intended to use more flexible or independent workers in the near future.

So, how do you become an invaluable independent worker to well-funded corporations and lean start-ups? Develop these four traits:

#1 Be the best at what you do (and believe that you are)

In an epic 1981 The American Economic Review paper, titled The Economics of Superstars, Sherwin Rosen says:

“Hearing a succession of mediocre singers does not add up to a single outstanding performance. If a surgeon is 10 percent more successful in saving lives than his fellows, most people would be willing to pay more than a 10 percent premium for his services. A company involved in a $30 million law suit is rash to scrimp on the legal talent it engages.”

What Rosen is saying is that talent is not simply a commodity that can be bought in bulk and combined to create a masterpiece. Companies know this and those wanting to work longer term with on-demand workers actively seek out (and pay more for) exceptional talent. Rosen also explains that there’s a premium to be enjoyed when you’re the best at what you do.

Naturally, then, if you’re in a marketplace where the buyer has access to all the performers, the buyer will choose the very best. It’s your task to educate and inform the buyer what makes you better than others. Include bold (but factual and provable) achievements and credentials in your profile, show examples of previous work, have glowing testimonials from people you’ve worked with in the past. Most importantly, when you respond to a proposal, do it with intensity, commitment and passion.

I’ve been on both sides of the on-demand economy for many years. By far the vast majority of proposals I’ve received in response to tasks posted have proven to me that the average gig worker doesn’t believe they are the best person for the job. If you don’t believe you’re the best, why should the buyer?

#2 Make soft skills like critical thinking, empathy, communication, collaboration and self-reflection a priority

Our education system — that hasn’t changed since the 1800’s — has taught us that academic prowess is the only way to get ahead in a competitive world. But how do you differentiate yourself when you’re competing against 162 million other academically strong remote workers?

The solution is to work on problem solving, relationship, communication, collaboration and self-directed leadership skills. None of these skills are taught in schools, colleges or universities and yet they’re the skills most needed in the new world of work.

Source: The Economist Intelligence Unit report “Closing the skills gap: companies and colleges collaborating for change” (2014)

It’s highly unlikely that soft skills will be included in the education curriculum in the near future, because of how difficult it is to assess them. So, how do you develop soft skills yourself? Here are seven resources:

  1. CASEL’s Social and Emotional Learning
  2. Center for Building a Culture of Empathy
  3. Cleverism’s Ultimate Guide to Soft Skills
  4. CPA Center of Excellence
  5. MindTools’ Developing Empathy
  6. Stanford University Graduate School of Education’s Challenge Success program
  7. University of New Mexico’s Innovation Academy

#3 Take the company’s success personally

Co-founder of WooThemes, South African-born Mark Forrester, says passion is so critical when making hiring decisions that, “A strong attitude and desire to share in our success is more important to us than experience and aptitude.” He says that the single difference between good and great is passion. Passionate people live and breathe the work they do. They don’t even think of it as work, rather an extension of themselves.

If you can work remotely as a passionate evangelical of the company you represent, you’ll stand head and shoulders above other independent workers. Make it clear that you want to use your talents for more than generating income. Show that you yearn to be part of something bigger than yourself — that you believe in the company’s vision, values, and mission. Show through your actions that you’re dedicated to making their success a reality.

Entrepreneur and investor Paul Graham describes that kind of person like this:

“An ‘animal’ is a salesperson who just won’t take no for an answer; a hacker who will stay up till 4:00 AM rather than go to bed leaving code with a bug in it; a PR person who will cold-call New York Times reporters on their cell phones; a graphic designer who feels physical pain when something is two millimeters out of place.”

The key to ‘being an animal’ as an on-demand worker is to be clear on your own purpose. Once you’re clear on what you stand for in life, choose to only work with companies who align with your purpose.

How do you become clear on your purpose? Here are five resources:

  1. Imperative’s Purpose Economy
  2. Oprah Winfrey and Eckhart Tolle answer questions on finding purpose
  3. Peaceful Warriors’ Life Purpose Calculator
  4. Seven TED Talks on Finding Purpose
  5. William Damon, Professor of Education at Stanford University interview on Path to Purpose

#4 Consistently practice and develop strategic agility

The world has seen more change in the last decade than it did in the entire century prior. The next decade will have even more change than the last one. We are truly in an age of unprecedented, rapid change, driven by what Ray Kurzweil and Peter Diamandis call “exponential technology.”

The number one quality that separates the very best entrepreneurs and remote workers from the rest is agility — the ability to change with the times, shift at a moment’s notice, and pivot when needed. It’s not something that can be taught. Even worse, it’s a quality that naturally wastes away over time.

“To remain valuable in our economy, therefore, you must master the art of quickly learning complicated things.” — Cal Newport, Deep Work

How do you develop agility as a future-fit skill in the gig economy? Here are seven resources:

  1. INSEAD’s interview with Yves L. Doz, Professor of Technological Innovation, on Strategic Agility
  2. London Business School’s 13 Agility Disciplines
  3. Lumosity, a brain training app created by scientists and game designers
  4. Recommended reading on strategic agility from Microsoft
  5. INSEAD’s reasearch on how Strategic Agility will help you stay ahead of the game
  6. Think on Your Feet, a workshop that trains you to analyze, organize and present your ideas
  7. Tim Ferriss’ The Art & Science of Learning Anything Faster


The top 1% of gig workers focus on excellence in their craft; developing soft skills like problem solving, collaboration and empathy; being crystal clear on their purpose and choosing to only work with companies that align with their purpose, and strategic agility.

The top 1% of gig workers focus on excellence, soft skills, purpose and agility.

On-demand platforms

Think you have what it takes to become a ‘1% gigster?’ Here are some of the more popular platforms to connect with buyers of your service, together with a summary of user reviews for each platform:

  • Founded in 2007, offers high-quality custom logos, print design, web design, and naming suggestions primarily for startups and one-man bands. High level of satisfaction among buyers; high chance of rejection among providers i.e. work must be done up-front and buyer selects preferred result.
  • Launched in Australia in 2009, this is the largest marketplace by number of users and projects (over 24m users and 11m jobs posted). Customer service can be slow and payments are often delayed because of “investigations.” Service providers are required to pay to “certify” yourself on your skills. Number of bids per month are limited.
  • Kriya.AI: A new chatbot-based platform launched in beta in 2016. Connects startups with developers, product or graphic designers, data scientists and growth marketers globally. Differentiators: uses Artificial Intelligence to match gigs to workers (as a service provider you don’t have to wade through projects and pitch, which saves time), chatbot-driven milestone tracking and payment.
  • Launched in 2007 in the UK, PPH is the leading freelance marketplace in Europe, with 1.5m users and 1.1m jobs posted. In October 2016, they exceeded $100m paid to freelancers. No certification quizzes required. Offer “Hourlies”, which are pre-packaged offerings at set prices.
  • (formerly Elance-oDesk). Full service platform founded in 2015 offering invoicing, time tracking, and payment. With millions of jobs posted on Upwork annually, freelancers are earning more than $1 billion via the site each year and providing companies with over 3,500 skills. The marketplace is ideally suited to low-cost entry-level work. Some freelancers are dissatisfied about the high fees (starting at 20% and scaling down the more work is done for a client). Some clients don’t like the high number of service providers who don’t use English as their first language.

If you’re looking for a full list and comparison of freelance platforms, here you go:

Enjoy your journey to becoming one of the top 1% of on-demand, remote workers. Please share any other strategies you’ve discovered that have made you a 1% gigster.

Michael Haupt is the best in the world at translating a company’s vision, mission, goal or objective into compelling, meaningful, empathic purpose-driven stories that excite and inspire action. Reach him on Twitter @michaelhaupt or use Artificial Intelligence to connect with him on



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