The Hesitation

You know the sound that’s made when you drum your fingertips against a table? The drrrrrrrum-drrum-drrrrrummm? And then the rhythm that comes about when you keep drumming? Then the rhythm that forms in your head in between the thoughts now overwhelmingly punctuated by the drumming?


Should I do it?


What if it doesn’t work out?


What if I fail?

Druuuummmm... What if it all falls apart? What if I finally learn and possibly confirm that my skills were simply a work of inspired fiction? That I’d be a fool to think I could do anything but live an expected reality spawned from an office desk.

That final drum and final thought. How you react to that determines your next step.

The Reality

Before delving into the intangible probabilities of that decision, let’s look at some tangible facts of the independent economy, currently known or trending as “the gig economy”.

By 2020, contract work will account for 40 percent of the global workforce. In the US, 53 million professionals are freelancers with LinkedIn documenting a 43 percent growth over five years in members listed as freelancers.

The concentric benefits of the digital marketplace and the increasing number of coworking spaces take away the need for a formal workplace to identify what’s “work” and what’s not work. Add that to the stereotypes attached to being a millennial (a generalized term at best for an entire generation that forms a major chunk of the workforce), and you have a world perfectly ripe for a newly inducted independent worker.

Inducted? Yes, because freelancers today are effecting a force of their own where a 9-5 is not the only way to work and where those that choose to freelance are not boxed into the lazy, unambitious category. It is a force that propels a community of independent entrepreneurs and hustlers who have chosen to and have the privilege to rely on themselves and their abilities to see how far they can go. This is a community existing on chance, on going against the expected path to individual success. As would be the case with this induction, you’d have to be a self-inductee.

This choice does not take away the value of taking a conventional path to prosperity. That too requires thought, strategy, hard work, and sacrifice. Sometimes, even more so, because of the number of players involved in the road to success. Not all can waive financial needs and the comforts that a steady paycheck can afford.

In other words, instead of gauging the quality of your work against a predetermined criteria, you’ll need to make up a reward system of your own to move forward.

The Possibility

But, if you do have the capability to rely on yourself and find yourself repeating that final drum and final thought over and over, then this reality checklist of turning independent is yours to devour.

Nip the reactive growth bug

In a traditional work environment, things are usually done a certain way in order to guarantee certain results. One is expected to conform to that certain way to climb up

Develop your skills

The gig economy is prime territory for designers, writers, filmmakers, programmers, marketing managers and event planners among others. Regardless of whether you fall into one, all, or none of those categories, you’ll need to figure out the skills on which you’ll build your independent career. This will include spending hours consuming content on improving your skills, taking courses to perfect your skills, understanding how to share your skills with others and most importantly, zeroing in on how you and your skills will help others. You’ll also find yourself creating a list of role models who are already doing what you’re doing. Whether you are an independent worker or not, having a mentor or role model to follow is essential.

Mobility and Flexibility

Among the greatest perks of turning independent is the nomadic life it enables. That dream of working in your pjs is as much a reality as is putting on a suit for an afternoon meeting with a client. But, that reality of not having a routine could also be a tad bit painful, especially for those used to compartmentalizing work time and play time.

You’ll have to figure out a schedule that works best for you. This will require a ton of trial rounds and the only thing that should be constant is you not beating yourself up for not sticking to schedule. That conditioning we talked about earlier? This part is among the most integral steps of undoing it.

Challenges of the Hustle

Becoming an independent worker has a stunning likeness to becoming an entrepreneur. Except you are not looking to build a team. Instead, you are your team, you are your product, and you are your CEO. You will need to learn about budgeting, time management, admin work, marketing and decision making. You will also need to learn how to value your work, decide the worth of a project against your time as well as chase the client to make sure you get paid for your work and time.

To do this, you’ll need to honestly analyze your skill set, the market reality and the difference you can make to a project. This process could send you down a deep and maybe cathartic turn of self reflection, but you’ll come out more aware than ever of what you can offer.

You’ll also need to learn when to say no. Your portfolio represents you, so be sure to actively curate what stays and what goes.

The chance to recognize your greatness

If you choose to become independent, you are choosing an opportunity to peel off the layers to your core and understand what you are and what you can be in this world. All the time in your hands plus the freedom from a schedule and set exceptions allows for more creativity and the time for more creative solutions. You could be introduced to the adrenaline high that comes from building something of your own, something that you created, something you love. That high doubles when you realize you gave it the time it deserved and did it at your own pace.

If you have the privilege of even contemplating between becoming an independent worker and working a desk job, then choose the former. Choose the former to challenge yourself, see what you are made of and discover what you can make.

Sure, others might have done what you have done before. But, you haven’t done it yet. You are yet to use your skill.

You might fail. But, what if you didn’t? What if you made a different choice that took you away from life as you knew it? What if this choice worked? What if this choice led to you becoming the greatest version of yourself?


Most of us are wired this way because we are conditioned from the very beginning to associate reward with unpleasant work, a perfect foil for the ego. Remember school exams? We toiled for hours in hope of an excellent grade. The times we didn’t make the top tier led to disappointment, ambivalence or abandonment of any further effort to do. Becoming an independent worker asks for an active undoing of this


the success ladder.

Your next step is the choice you’ll make between building yourself into an enterprise, an independent worker, or working for another’s enterprise.

Credit: Paul Itkin

Credit: Lacey Raper

Credit: Coley Christine

Credit: Paul Itkin





observe. write. express.


Copyright 2016

Wandering Local. Design by Imagyne.


Copyright 2016

Wandering Local. Design by Imagyne.





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