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How to Start a New Side Hustle Part 1

How to Start a New Side Hustle Part 1

In his 2014 New York Times bestselling book “Show Your Work”, author Austin Kleon encourages readers to take people behind the scenes. Taking people behind the scenes means allowing them to see the processes that lead to a finished product. Times sure have changed! When I was growing up, creators took pride in guarding the details of how “the sausage got made” and in unveiling said sausage only at the end when everything was “perfect.”

Today, we all recognize the advantages of documenting our journeys even while they don’t lead to the desired outcomes. For the creators, documenting and sharing their steps provides a sense of incremental fulfilment along the way to achieving their goals. For the observers, seeing someone else’s experiences accelerates their learning and motivates them to pursue their own ambitions. What are you in the process of pursuing that if showcased could benefit not only you but also your family, friends, and colleagues? I asked myself that question and thought of a few things worth sharing with you 😊.

I mentioned in my intro that I have taken pleasure in attempting to launch part-time business ventures over the years in addition to my career in corporate Information Technology. I’m grateful that the term “hustle”, used pejoratively almost exclusively in African-American newspapers in the 1920s, got a much needed upgrade to “side hustle” in the 1950s to signify any legitimate “work performed for income supplementary to one’s primary job”.  Fast forward to 2023 and nearly two in five (39 percent) of U.S. adults have a side hustle, according to a new Bankrate survey. Chances are if you haven’t thought of having one yet, a friend of yours has. In fact, they might be offering to pick up the bill at your next restaurant outing with money earned doing something other than their 9 to 5 job. 

Yet in my case, and I suspect the same for many others, my primary motivation for dabbling in side hustles isn’t pecuniary. Of course, any financial gain is as rewarding to me as the next man. But making additional money isn’t what’s driving me to keep trying these different things. I’m driven by an interest in applying and continuing the business and marketing education I received back when I thought I would go on to wear custom made suits and pitch campaigns for an ad agency like Don Draper in Mad Men. As much as I love being a public servant, there’s nothing like the thrill of developing an idea into a commercially viable product or service.

In response to Mr. Kleon’s call to show the whole creative process that is required to make a final masterpiece, I will let you in on my next commercial side hustle starting from the ground floor 😊. I will write a series of blog posts showing the entire process from ideation to commercialization and everything in between: the good, the bad and the ugly (and trust me, it’s gonna get ugly lol). If you want to quickly see and read my posts on this process in sequential order, just look for and click on this tag: About Side Hustles. While my aim isn’t to get rich from this venture, you may have a financial objective and wish to learn from my experience. For this reason, I will document my process in a way that applies some of the for-profit best practices I’ve learned from my formal business education and from my time as a business leader in the IT industry prior to joining the federal public service.

If I had to draw a diagram of circles in which each circle shows the basic question that you must answer on the way to creating a new venture (be it a side hustle, a hobby, or a business), the diagram would look as shown below.


Inspirational speaker Simon Sinek gave a now legendary Ted Talk on how successful leaders must identify their purpose, vision, or cause first before deciding how they will accomplish their aim with some product or service. I agree with him on this point. As shown in my diagram above though, I have a slightly different take on his Golden Circle that is informed by my experiences in non-profit community service in addition to the IT business. 

In this first installment of my side hustle series, I’ll tackle the central question: “Why am I doing this?” I will address the remaining questions in my diagram (For Who?, For What?, and How?) in subsequent posts. Defining your “Why” before launching your side hustle offers several benefits:

  • Having clarity on your internal motivation for starting a side gig will keep you persevering when obstacles arise and the going gets tough.
  • You’ll be able to self-evaluate the success of your venture by measuring its performance against your own goals and objectives.
  • Your purpose will serve as a moral compass by ensuring you don’t stray into actions misaligned with your intention.

I hinted at my motivation earlier, but let's use the “Five whys” technique for purpose discovery to unearth a more complete set of purpose statements. While my answers will of course be quite personal and unique to my circumstances, you'll find this questioning exercise just as useful to you if you open yourself to it. Here are five questions and answers to help clarify my “Why”:

  1. Why do I want to start a side hustle?
    • I want to continue to learn and apply the business knowledge that I don't get to fully apply in my day job.
  1. Why does applying my business knowledge outside of my day job matter to me?
    • I want to continue to learn new business practices.
    • I also want my girls to see that they too can pursue and fulfil various vocational and/or recreational aspirations at the same time as their "main career".
  1. Why do I want to pursue another vocation?
    • I want to do something that utilizes my unique combination of skills to make a direct and visible positive impact on people's lives.
  1. Why does making a direct and visible impact on people matter to me?
    • I want to experience the personal satisfaction that comes from seeing a customer benefit from my product or service.
  1. Why does seeing a customer make use of my product or service bring me satisfaction?
    • Seeing a customer benefit from my product or service confirms that I have correctly applied my business knowledge. That confirmation is rewarding!

Putting it all together then, I am starting this side hustle to:

  • Apply and continue to develop business acumen.
  • Demonstrate to my girls that they can do many things at once.
  • Utilize my unique combination of skills to make a meaningful contribution to people's lives.
  • Validate that I have correctly applied the business best practices I've learned.

Would you believe me if I told you this side hustle of mine is already on solid footing to become profitable even if none of my statements above have anything to do directly with making money? It is indeed a paradox that the most profitable companies are not the most profit-focused. Research shows that companies with a purpose more meaningful than profit tend to make the most money. So even if your new venture has a financial objective, which is totally ok, make sure you keep asking yourself “Why else?” until you get to reasons that run deeper than dollars. Your venture’s survival may depend on it.

Now that I've defined my “Why,” in the next post in this series I’ll address the “For Who” in my diagram. This process of "showing my work" will be fun 😊! Hope you stick around and help me build this side hustle into whatever it becomes. 

Onwards and upwards.

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