Do This Before Starting A Side Hustle

Two Pennies Worth
Fortune For Future
Published in
4 min readNov 15, 2020

Suggestions to improve the odds of becoming successful at a side hustle

Throughout the years I’ve tried countless side hustles to no avail. It always starts the same; First, I scour the web in search of an idea that resonates. Then I read a couple of success stories and think: “Hey, if they could do it, so can I”.

At this point I am completely invested and I dive in, researching as much as possible, building up some momentum … and then life happens, deadline at work, family responsibilities or I realize it’s not as easy as it seems. This leads to me eventually getting unmotivated and calling it quits.

The definition of insanity is doing the same thing over and over again and expecting different results.

— Albert Einstein

After many trails and errors, I‘ve realized that the only reason I started these side hustles was to create an additional income stream. Furthermore, the “promise of extra income” does not provide sufficient motivation, at least for me, to push through when it starts to get tough. This was the moment I decided to change how I approached side hustles.

Before starting again, I tried to understand what’s motivation of others to keep pushing through even when things seem discouraging. The main takeaway from these success stories is to only start something when you’re passionate about it … well to be honest I am not passionate about filming myself and posting it on Youtube or developing my own course, dropshipping, social media marketing, affiliate marketing or creating my own e-book. I could care less about Amazon FBA or Upwork.

I always considered myself a relatively apathetic in this sense, I don’t really feel pulled to a particular subject or job. If you put a gun to my head and tell me to choose something that I’d have to do for the rest of my life or else … I’m gonna be in a lot of trouble. This does not necessarily mean that I feel lost. On the contrary, there are a lot of things that I want to try out, I guess I just get bored easily.

To summarize, I believe that you can improve the chances of becoming successful by finding sufficient reasons to not get discouraged and keep pushing through! This definitely is easier said than done, however it did give me a new perspective. So, these are the two suggestions I have that can keep you motivated.

Plan for failure

So given that in my case, I am (mainly) financially motivated, I started to think: “if money is the core reason to start a side hustle, couldn’t I do something that complements my current skillset and would increase my value as an employee”.

In this case, even if I fail, I win! As the experience gained could be leveraged to increase my value as an employee and improve salary negotiations. As a result, my side hustle would lead to “additional income”.

This not only greatly strengthened my motivation to push through when I get discouraged, but also narrowed my focus with regards to which side hustles to pursue.

Redefine your definition of success

Aside from planning for failure, I also redefined what I considered as being successful. Initially, I considered being successful at a side hustle tied to monetary gains.

Based on previous experience this definition of success is rather counterproductive as I would get fixated on short term results and if these targets are not hit, I would get discouraged and this marks the start of the downward spiral, which ultimately ends in me quitting.

Instead of primarily focusing on making money, I redefined success as learning the required skills and being able to apply these skills. This became my priority and monetary gains came later. As a result, I measured my progress in my ability to understand and apply these skills, which kept me motivated much longer as opposed to focusing on the financial results.

So, did I become a success story?

Short answer: I did start a side hustle, however I am not making a ton of money…not yet.

Long answer: For the past two years I have started a side hustle that complements my current skillset as an employee. I have leveraged this new skill to add value as an employee and increase my salary. Furthermore, I am still motivated and looking forward to continue learning, gain experience and hopefully make additional income. So my answer is yes, I do believe I have achieved success!

Conclusion

The journey to starting a side hustle and becoming successful is arduous and most likely will take a couple of attempts. To try to beat the odds, the following suggestions helped me to stay motivated and hopefully can help you too!

  • Plan for failure
  • Redefine your definition of success.

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Two Pennies Worth
Fortune For Future

An inquisitive quant/actuary that wants to share his two pennies worth on several subjects.