Theme 5: Option Generation

Chase the things that pull you and generously demonstrate your value to others.

“Strive not to be a success, but rather to be of value.”

Albert Einstein

Why is this theme important?

Help others and you’ll help yourself. Pursue things that excite you and be quick to demonstrate value. Act on your ideas, give generously and focus on demonstrating the value for others and you’ll open up new paths and exciting options for yourself.

Core Ideas

Understand the future of work and careers.

“Uber, the world’s largest taxi company, owns no vehicles. Facebook, the world’s most popular media owner, creates no content. Alibaba, the most valuable retailer, has no inventory. And Airbnb, the world’s largest accommodation provider, owns no real estate. Something interesting is happening.” Tom Goodwin, The Battle Is For the Customer Interface (Techcrunch)

The way the world works is rapidly evolving and it’s happening right before our eyes. The Internet has allowed us to challenge and reimagine everything we do. Even the concept of the full-time job altogether. A recent BloombergBusiness article stated that 6 million American workers are choosing to work part-time, “not for economic reasons but because they want to design their own careers.”

So the first step in generating new options and ideas for yourself is to realise that we live in quickly changing times. People and companies are working differently. The most influential organsiations in the world are no longer operating the way they were when we first entered the workforce. Opportunities are abundant if we know where to look and how to expose ourselves to them.

Explore a portfolio career.

If you haven’t heard the term “portfolio career” before, here’s how the site Quintessential Careers defines it:

“Portfolio careers are usually built around a collection of skills and interests, though the only consistent theme is one of career self-management. With a portfolio career you no longer have one job, one employer, but multiple jobs and employers within one or more professions… Instead of working a traditional full-time job, you work multiple part-time jobs (including part-time employment, temporary jobs, freelancing, and self-employment) with different employers that when combined are the equivalent of a full-time position.”

We’re now living in a world where a portfolio career is possible. In addition to more people working part-time deliberately, many are choosing not to commit to one employer, but choosing instead to apply their skills and talents across multiple employers and multiple projects. is one leading example of this trend into a “portfolio career.” Upwork provides an online marketplace for freelance workers, making it easy for any individual or organisation to find and hire professionals for almost any type of knowledge-based work. It’s not just for startups either; big corporates are beginning to tap more into freelance workers. According to Upwork: “90% of businesses are hiring contingent workers, and the independent contractor market is more than $1 trillion globally.”

People who tend to navigate this landscape successfully treat their career like a portfolio of projects and skills, whether they have one job or many. We’ll dive more into viewing the stepping stones of your escape as projects in Theme #7 – Experimentation & Projects. But the key to remember here is that we’ve entered a world of work never seen before.

Chase your tennis ball(s).

When you’re not sure how to start unlocking new ideas and options for yourself, remember the tennis ball analogy from Theme #3 – Values & Direction.

Every time you walk by a bookshop, do you feel pulled to walk in? When you hear someone talking about sailing, do you instantly perk up? If you hear about a new business idea and think “HELL YES!”? Those all sound like tennis balls.

The goal is to get in touch with that voice that perks up. We’ve been fantastically trained to quiet that voice and to ignore it, it often suggests silly, stupid, childlike ideas. But when we’re stuck and trying to figure out where to go next, that’s the exact voice we need to be paying attention to.

The next time you sense a tennis ball, go follow it. See where it takes you. It may lead you to a new person, a new organization or a new project that may be integral to your grand escape.

New opportunities will crop up as you let yourself be pulled by things that speak to you. Pay attention to the things that pull you; like a tennis ball pulls a dog.

Follow your frustrations.

Different people are driven by different things. If “chase your tennis ball” doesn’t work for you, it’s possible that you’re driven more by frustration, anger or injustice. That’s perfectly fine and it can be an equally effective indicator for you and your direction.

What frustrates you? What problems do you see in the world? What bugs you to no end?

Frustration is what drove Emily Penn to become the director of Pangaea Explorations, an organisation dedicated to studying ocean challenges in the most remote parts of our planet.

Emily wasn’t always interested in the health of the Earth’s oceans, but seeing firsthand the amount of plastics contaminating our oceans and cluttering our coasts disgusted her and she knew she needed to do something about it. It was a “tennis ball,” driven by a frustration. Since her initial interest in plastics, Emily has since organised the largest ever community led waste clean-up from a tiny Tongan island and trawled for micro-plastics on a voyage through the Arctic northwest passage. She’s become an expert in her field merely by following a frustration long enough.

If you’re bugged by a problem, a defect, a deficiency in our world, chances are other people are too. By listening to that frustration and giving more than lip service to it, you may create a new opportunity for yourself. By starting something, you may open a new door for yourself. Follow a frustration you just may forge a new path for yourself.

That is, after all, how Escape The City started. Feeling stuck in a meaningless corporate job was a frustration that has now rallied almost a quarter of a million people around the world who feel the same. Have the courage to stand up and be a voice for a frustration that doesn’t yet have a voice.

Create value regardless of financial reward.

Charlie Hoehn graduated at the height of the global recession in 2008 with a marketing undergraduate degree, no work experience, and minimal skills (“Proficient in Microsoft Office” was the gold star on his CV).

After an unsuccessful job hunt with zero prospects, he somehow managed to land work with a handful of high-profile entrepreneurs and bestselling authors he admired including Tim Ferriss, ‘Four Hour Workweek’, Ramit Sethi ‘I Will Teach You To Be Rich’, and Tucker Max, ‘I Hope They Serve Beer in Hell’, among others.

In his book, ‘Recession-Proof Graduate’, Charlie describes how he came to work with his heroes using a principle called “doing free work.” Essentially, Charlie reached out to his heroes and offered to work for free on a clearly defined mini-project as a means to display and communicate his potential value.

Doing free work sounds simple. But this isn’t just about taking an unpaid internship and volunteering on a community project. It’s more targeted and ambitious than that. Doing free work is about aiming high and offering to work on mini-projects for people you admire and from whom you can learn from.

“Doing free work is about building healthy relationships with people you want to learn from and work on projects you’re interested in… Whatever ideas I propose will somehow be tied to skills of mine, but phrased in a way that’s beneficial to the person I’m emailing.”

Doing free work works because it allows you to display your value FIRST, potentially without the expectation of return. In doing so, you’ll give yourself a better shot at a new opportunity.

Give, give, give. (Then ask).

Most people are afraid to give before they ask for what they want to receive. Doing free work holds a future unknown. Understanding clear return on investment for the time and effort that giving value away requires, can be difficult. While rationally sound, this kind of attitude is based in a ‘City’ mindset, and it’s largely unhelpful when you’re trying to escape into something new. Instead, we must practice giving freely, early and often.

Gary Vaynerchuk is the founder of Vaynermedia, WineLibraryTV (an online wine show), and the author of several books on entrepreneurship. He uses the phrase “give, give, give, ask” as a strategy for success in using social media as a marketing tool, saying you have to give more than you ask in return. But the same can be true for everything. Especially when trying to generate new options for ourselves.

Give before you ask. Give many times before you ask. Display and demonstrate your value. Build trust. Because trust is as important as it’s ever been. In a world where we buy from people we’ve never physically met, get into strangers’ cars we’ve never known, sleep in foreigners’ houses in places where we’ve never been — trust is our currency now.

And trust requires us freely giving and showing what we can do before we ask for anything in return. Giving is an invitation for the right people, opportunities and options to enter our lives.

Your Objectives
  • Explore the range of ways in which people are building careers and businesses today.
  • Learn new techniques for generating lots of ideas and new potential paths for yourself.
  • Understand the simplest, quickest ways of turning your ideas into small realities.
  • Build on your past experiences and future ingredients to generate ideas that are viable for you.

Useful Resources

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