The Challenges For Side Hustlers and Side Hustle Investigators

We did some research a while back to understand the Side Hustle market and its participants a bit more. We know that many people are looking to supplement their incomes, want to start a business on their own, and want to understand more ways to make $ and save $. Almost 60% of working aged Americans fall into one of our Side Hustle profile categories.

Here were the principle challenges they called out along with a couple of points on each that might help one address these challenges.


Which side hustle opportunity is right for me? This is primarily among those looking to find the right model; to tap into an existing opportunity and earn an income right away. Should I drive for Lyft? Should I consider Herbalife? Should I become a tutor? etc.

Top Challenge: Evaluating which option is right can be daunting, but here are a couple of sites that might help.\

  1. Here's a nice post to get the wheel's spinning by Simone Du Toit on Career Karma:

  2. This is a pretty extensive list from Lauren Bennet on MoneyPantry of some side hustle apps to consider in 2022:

  3. Here's another list of some different side hustles to consider from Scott Lieberman on the


Challenge: How much effort is going to be needed for this side hustle?

Time is the one unifying factor across all humans and that time is valuable. We all need to assess what return we'll get back for the amount of effort needed. Plus when evaluating a second income source we need to make sure it can be done without completely sacrificing that ever important "me" or "family" time.

  1. Passive income is a popular topic - how can I make money with minimal effort over time. Truth is, passive income isn't quite as labor free as we might think. It requires "up front" labor to set up, but the good news is that if you do develop something that can work over time, the money can indeed start to come in without significant labor "long term".

  2. is a nice little post that gets at some passive income ideas that might give you some ideas.

  3. Being organized and setting up a good schedule for your side hustle is important. American Express offered some good tips in this post by David Rodek:

  4. Looking for ideas of side hustles that don't require a ton of time commitment? Here's an article from a couple of year's ago on Vital Dollar by Marc Andre: . Transcriptions may not be relevant as much given AI alternatives getting better and better, but there are some interesting things in here to get some ideas.


Challenge: Economic factors and money needed to pay bills

Maybe you are thinking about making extra money to pay off specific bills or debt. Identify the goal (like paying down student debt, or paying specific bills like rent, mobile, internet, television, etc.). That will give you a goal to work towards and then you can look at what kinds of opportunities or second jobs could help you pay those bills quicker / easier.

  1. The first step likely means taking your budgeting more seriously. Personally I hate this step, but every time I have done it, I get a lot more out of it than I thought. Knowing where your money is going is never a bad thing - except that if you are like me you discover that your money has been going to places you wish it wasn't...But in this case, you want to get a better handle of what you "need" to feel better. A budget calculator like this one on Quicken can really be a good place to start:

  2. Also, this post on Credit Karma's website is a great place to start when thinking about jobs or side hustles that might help you pay off a specific debt faster (like student debt).


Challenge: What market should I look at or What will it cost to get started?

The first step in investigating your own startup or startup side hustle should be to define your concept and business plan. Going through this process will help you define the market, identify costs and budgetary needs, and then help you to get a better feel for what will be needed. You can always tweak the plan, but if you don't have a formal plan in place, you really should start there.

There are a ton of great resources out there but here's a couple:

  1. SBA (Small Business Administration):

  2. Shopify:


Challenge: Am I too old? Is it OK to start something considering the pandemic health environment?

Short Answer: You're never too old and there's no time like the present. This is especially the case as inflationary and other economic concerns loom large in our minds. Starting a business is kind of like having kids - there's rarely a perfect time to do it, but if you know you want to, then start. As with the other challenges, planning helps and make sure you know your risks, but don't be afraid.

Some articles:

  1. 5 businesses to start in retirement for under 5K:

  2. Marv Valladares of Pinstripe Magazine posted this article on Legal Zoom about adapting when starting a business in a pandemic:

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