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The challenges of starting a side hustle

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Brooke Joly Article 3

Side hustle culture has been exploding for the last few years. Across the country and around the globe, people everywhere are stepping into alternative part-time employment by side hustling. This classification of work generally consists of creating products or providing services that are done on an ad hoc, or part-time basis.

I first decided I wanted to explore starting a side hustle back in 2015. I always loved to write and tell stories, so what better way than by starting a blog to share my thoughts with the world? I was drawn into developing my own side hustle because:

  • I wanted to do something that mattered in my free time. I realized I was squandering away my nights and weekends watching television or doing other mindless activities that were contributing to my waistline instead of my bottom line.
  • Side hustles have no schedule. Nobody tells you when to drive for Uber, accept jobs walking dogs on Rover, or create greeting cards for your Etsy shop. You can work when you want, for how long you want.
  • Success is determined by a personal drive to succeed. This is great for people like myself, who tend to be intrinsically motivated. If you’re going to have a successful side hustle, you need to work hard and get it done. It’s up to you and nobody else.
  • A fun way to earn extra income. One of the biggest draws to the side hustle is the opportunity for additional income outside of traditional employment. Making a few bucks on the side means you can use that money for things like bills, savings, or discretionary spending.

While the pros of starting a side hustle very much outweigh the cons, there are still many challenges a new gig economy worker faces that could prevent someone from getting started. Below are a few of the many challenges I faced trying to start my hustle, which ultimately resulted in a multi-year gap between deciding to do it and getting it done. I’m hopeful that by sharing these challenges and how I overcame them, it will present you with an opportunity to get going faster if a side hustle is something that’s calling your name.

Overcoming imposter syndrome

The feeling of being an imposter was hands down the most significant hurdle I faced in starting my side hustle. I felt a pull towards blogging for ages, even going so far as to create articles on weekends that didn’t see the light of day for years. I would write (what I thought was) great content, but then I still thought to myself, “What right do I have to be telling people how to live their lives when I’m still figuring things out myself.”

Imposter syndrome is the feeling that you’re not worthy of speaking about or doing the very thing you’re trying to do. These toxic thoughts can stop you before you even start.

What helped me is to remember that we are all unique. The only person that can provide your gifts to the world is you. Even if 17 other bloggers have written about the challenges of starting a side hustle, I bring a viewpoint to the table that the world hasn’t seen yet. The markets for side hustles are only saturated if you believe you can’t bring a different talent to the game.

Finding the time

This barrier is a huge one for a lot of people. This same excuse pops up anytime someone wants to try something new, like start an exercise routine, or take a night class. Any new habit needs someplace to exist in your life, and most of the time, that means you’ll need to make space for it by sacrificing something else.

What helped me scale this hurdle was tracking my time for a week. I entered blocks of time on a spreadsheet in 15-minute increments and holy moly the results were disappointing. I realized how much time I spent doing nothing of value, like watching tv or playing on my phone.

The outcome of my endeavor in time-tracking is that I uncovered hours each week to pour my efforts into a productive side hustle. I encourage anyone who wants to find time in their schedule for a new adventure to do this simple tracking task for one week. The results will shock and awe, and hopefully present opportunities for you to tackle a new gig.

Figuring out what to do

I hear from many people looking to start a side hustle that they’re unsure what to offer or create. There is so much opportunity out there for different side hustles. You can do anything from delivering goods to crafting, babysitting to dog walking, and even writing to reading books for money. If you don’t have an immediately apparent passion, try a few different things. The beauty of the side hustle is that it’s not your full-time job, and you’re by no means married to it. 

It’s important to remember that the majority of side hustles also have extremely low barriers to entry. This means the cost, both time and money, is relatively small, and you can change a side hustle if it’s not working for you with minimal waste. Most of the sites that facilitate freelance arrangements are free to join and will only take a cut of profits after services are rendered.

After beginning my hustle, I rested on the fact that if at any point I didn’t want to do this anymore, I wouldn’t be in the hole for more than $25. That’s a small enough amount I don’t have issues parting with, should the need arise.

Actually getting started

If you’ve ever tried to establish a new habit, you know that getting started is the most challenging stage. I started and stopped creating content for a blog for years before I committed to doing it as a regular part of my life. Once I had the momentum, though, it was easy to continue.

Something that helped me get past this roadblock was to tell only a few people in my life about my side hustle. Once I said to family and close friends, “I’m starting a blog,” they, in turn, would ask me about it, which kept me accountable. These types of daily or weekly accountability check-ins pushed me to move forward. I didn’t want to disappoint myself, but I also didn’t want to disappoint the people in my life who were now committed to supporting my new endeavor.

You have to put yourself out there

The moment that you start a creative endeavor be it creating greeting cards, website design, or contract work, you’re opening yourself up to criticism. One of the hardest things I’ve done in recent memory was hitting the “Publish” button on my blog, thereby setting it live for the world to consume. It was terrifying. Never have I felt so exposed.

What helped me overcome this fear of failure and criticism is realizing that I was doing my side hustle for me. Yes, of course, I want others to read my blog and support my craft, but I wasn’t doing it purely as a money-making activity. I genuinely enjoy writing and putting my heart out there for the world to receive. If you’re genuinely doing a side hustle that you’re passionate about, you care not about the criticism of strangers, positive or negative.

There is no instant gratification

There are very few side hustles that are going to reward you for getting started instantly. It will likely be weeks or months before you begin to see returns for your hard work. In a society that thrives on instant gratification, immediate connections, interactions, feedback, likes, etc., it can be extremely challenging for people to accept that they will need to put in a lot of time and hard work to get results.

Many people who begin a side hustle, and realize the effort it takes, will quit rather quickly. The ones who power through, remain consistent, and deliver quality work, will be the ones who prevail. If you’re serious and willing to commit to your side hustle, keep Dory’s image & motto from Finding Nemo in mind and just keep swimming.

Side hustles are brilliant ways to spend your time doing something productive, and hopefully lucrative so that you can start building wealth both on the inside, and out. I encourage everyone to at least examine what’s out there that aligns with your interests. I’d be willing to bet that if you’re able to overcome the challenges outlined in this article, an enjoyable, and profitable, side hustle is waiting for you just around the bend.

Contributor’s opinions are their own. Always do your own due diligence before investing.

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