Why Side Hustling?: Overcoming The Freedom Deficit & The Pursuit of Alternative Currencies

article side hustling Jun 15, 2022

Through the lens of the 9 to 5 workplace, side hustling is seen as something like this:

“Work performed for income supplementary to your primary job.” 

In the 1950s, they called it moonlighting. 

Second gigs worked in the evening, literally by the light of the moon. 

People have had multiple lines of income for decades. 

It’s no secret that this trend exploded during the pandemic. For many, the linear, singular employment model that defined the workplace of the 20th century broke amidst COVID 19. The mirage of job security evaporated, and the all-eggs-in-one-basket approach to income generation was exposed for the fragile system that it is. Millions have moved on from this past model of work and are now in pursuit of multiple lines of income through side hustling.

However, after working with over 400 side hustlers over the past two years, it has become clear that while this definition might speak to why some people start some side hustles (for supplementary income), it certainly doesn’t define the why for all of us. Money isn’t the only motive. It isn’t even necessarily the primary motive. We value multiple, alternative currencies: time and freedom, social impact, skills, social capital and relationships, etc. Side hustling creates a pathway to each of them. I have multiple pursuits as an entrepreneur because the things I value over everything are freedom & relationships. I want to own as much of my time as possible. And, I want to choose not only what I spend my time doing, but who I spend my time with. The 9 to 5 workplace of the past is terrible at providing access to the capital I value most - when I had a job, I was operating with a freedom deficit. 

That side hustling is pursuing a supplementary line of income, while your primary thing must be a job, that we must participate in the 9 to 5 system, is the second outdated element of the normcore definition of side hustle that needs to be reimagined. I haven’t had a job since 2012. I am an entrepreneur with one solo business and two small businesses. Multiple lines of income. Multiple pathways to the alternative currencies that matter.  I absolutely identify as a side hustler. While many have part of their portfolio of income generated by a job, that’s not the case for a lot of us. 

To really get at why folks choose to side hustle, a necessary first step is getting aligned as to what the term means in the current context of the early 2020s. Side gigs for extra income - that’s the system’s definition of side hustling. That’s 20th century thinking about a 21st century idea. Like many of our systems and world views, our preconceived ideas about side hustling specifically, and entrepreneurship + hustle culture more broadly, need to be dismantled, re-imagined and re-built.  

Let’s start here: side hustling is not a singular, fixed thing. It is a spectrum. And our experience within that spectrum is alive. It evolves over time. It might include full-time employment with freelance work done on the side. It might include part-time employment, creating a Shopify store to sell something you make, and then selling a course to teach others how to sell products like you. Or, it might mean being a full-time entrepreneur with a thriving small business, who starts to grow a second business, while writing a book and opening up more passive income. Side hustling is not a singular, fixed thing, and neither is the motivation to side hustle. It’s not just about extra income. You have multiple currencies you value and your decisions are driven by your need / desire to acquire more. 


It’s also not about the hustle. Traditional hustle culture and embracing the grind 🤮 are precursors to burnout. This glorifies the output obsessed, nose-to-the-grindstone mentality that causes harm to so many entrepreneurs. These are toxic, outdated, cubicle, 20th century ways of thinking about the workplace. Of course, there have to be moments of serious hustle and hard work. But it’s not a single paced sprint - that’s short-sighted. It’s a journey with varying paces - moments of going fast, and slow. Intention is the name of the game. 

Side hustling is much more than work performed for income supplementary to your primary job. Side hustling is a way of life, one in which individuals choose to leave the linear, singular workplace of the past, and instead embrace being  multi-passionate, multi-talented humans who pursue multiple things in pursuit of multiple currencies.

In that way, I encourage you to think of side hustling in this way: 

Side Hustling is growing an adaptable portfolio of work that provides multiple pathways to alternative currencies. 

So why are so many people choosing this path? Why are so many pursuing portfolios of work in pursuit of alternative currencies? 

After helping to launch over 400 side hustles in the past two years, we've identified 4 main factors that propel folks to adopt a portfolio approach to their lives:

  1. A driving force for many of us is our natural want to do more than one thing. The systems around us encourage the pathway of narrowing your focus, finding one thing you can do as a full time job. But for many of us our natural disposition is to be interested in many different things. To spend our time doing many things. Many of us side hustle because we are multi-passionate, multi-talented people who want to acquire alternative currencies through multiple pursuits. 
  2. Valuing multiple currencies is also at the root of growing a portfolio of work rather than participating in the employee-centric, institution-led workplace of the past. While full-time jobs can provide avenues to $, they also create a freedom deficit. Within the confines of the 9 to 5, your time is under the control of someone else 40ish hours per week, 48ish weeks per year. We are taught that the best we can hope for is to own the edges of our existence: mornings & evenings, weekends & holidays, and retirement. In the workplace of the 20th century, we spend most of our lives having to ask permission to take ownership of our time. Overcoming this freedom deficit and taking back greater control over time is perhaps the most common driver for those who shift toward portfolio based living and abandon the 9 to 5. 
  3. While many folks reject the 9 to 5 in pursuit of more freedom, others have directly experienced the fragility of the 20th century workplace paradigm, which assumes throwing all of your eggs in one basket is a viable strategy to create the sustainable income needed to make the most out of the edges of your life. COVID brought to light the fragility of the modern workplace in the face of rapid, unpredictable change. Many have made the leap into side hustling because growing multiple lines of income creates resiliency and helps to defend against the workplace uncertainty that surrounds us. 
  4. In that way, portfolios of work allow you to play defense. But, they are also a great strategy for going on offense - for uncovering opportunities to exponentially grow your access to each of the currencies you value. You can’t double your income in one year with a full-time job. You can’t double the amount of control you have over your days with a full-time job. In the 9 to 5 world, we are confined by linear growth opportunities. Growing adaptable portfolios of work through side hustling puts you in a position to take much bigger leaps: it creates the conditions for us to become Exponential Individuals. 

Being multi-passionate, overcoming the freedom deficit, pursuing multiple lines of income to protect against uncertainty, & opening up opportunities for exponential growth, are all factors that drive folks to side hustle. People’s motivations for doing things are layered and complex, and it is likely that a blend of these factors have propelled you toward side hustling. The fascinating thing about side hustling is that while these range of motivations exist, each of these factors are driven by a first, causal change, one that takes place in the mind of all side hustlers. I am talking about a change in perspective.

First and foremost, as side hustlers we have changed the way we look at the world of work and our place within it. We have decided to actively reject the workplace of the past, to participate in dismantling that system, and to build something new in its place. Side Hustling is a movement, and like any movement, it starts with a shift in perspective:

The first change is when you change your mind about how you look at things. When you do that, you start to see that there might be another way, one that you have not yet been shown. 

We are a generation that has changed our minds about the world of work. We are seeing that there are other ways to work and to live. We are taught to be students and then to be employees. We are shown an institution-centric view of the world. That worldview is being dismantled. As side hustlers, we are rejecting that paradigm and we are building something new. 

Dismantling & displacing long standing world views is not a new phenomenon. We have often questioned the ideas that came before us, rejected them, and built something new in their place.

For generations, it was universally accepted that the earth was the centre of the universe. People around the world accepted that the stars, sun, and other planets revolved around the earth. While some folks questioned this perspective for generations, it wasn’t until the 16th century that this long held point of view was dismantled and displaced by a new truth - that the sun was in fact the force of gravity at the centre of the universe. New tools, better tech, and deep questioning, allowed us to reframe our understanding of the universe as a whole. Today, the idea of an earth-centric universe is archaic, ridiculous and laughable.

For generations, it was universally accepted that large institutions were at the centre of the universe. People around the world accepted the prescribed perspective that individuals were small cogs progressing through various institutional machinery, in service of the corporate institutional masters that were the centrepiece of the 20th century workplace. As students, we were small parts within the all-powerful system of education (we even had student numbers to identify ourselves as one of many thousands of cogs within the college industrial system). For generations, we accepted and followed the traditional pathway from the world of school, into the world of work, where once again we were pulled by the gravitational force of corporate orbits. As small cogs within the corporate machinery, we strive to climb ladders, to become more important small parts of the institutional powers that ruled the 20th century. 

While some folks questioned this perspective for years, and even departed from that worldview, it wasn’t until 2020 that this long held point of view was dismantled and displaced by a new truth - that Individuals are in fact the force of gravity at the centre of the universe. YOU are at the centre of your universe, and there are constellations of institutions, corporations, schools and other entities orbiting around you. You are the force of gravity. You pull opportunities into your world as you see fit, to build the life you desire. We were not born to be line items on a corporate balance sheet in service of institutional self-preservation and increasing value for shareholders. New tools, better tech, and deep questioning, allowed us to reframe our understanding of the workplace as a whole. In the not too distant future, the idea of an institution-centric workplace will be seen as archaic, ridiculous and laughable.

So, why do we side hustle? Why do we grow portfolios of work?

We are part of a global, generational shift in perspective. We have decided to reject the institution-centric world of work, and have embraced the human-centric workplace in which every individual is empowered to be in the driver's seat of their life.  

We side hustle because we reject the linear trappings of the 9 to 5. 

We side hustle because we have decided to take back control of our lives. 

We side hustle because we value more than money.

We side hustle because we want to work different and live different. 

We side hustle because we want to be free.

What's your why?

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