Good things happen to those who hustle.

— Anaïs Nin

One of the most empowering—and detrimental—aspects of a freely accessible internet today is the paradox of too many choices. You can sift through thousands upon thousands of side hustles available at your disposal. There are hundreds of freelancing sites, millions of Facebook groups, and billions of websites. Even on a site like Fiverr.com, there are over 550 different services that can be offered by freelancers.

Sounds amazing, right? In the lens of opportunity, it has never been better. Yet too many choices can create a psychological phenomenon in which we either delay making a choice altogether, or we feel dissatisfied with the one we did make (Krockow 2018). It's why looking at a menu with over 100 different entrée options can, in a lot of ways, stress you out. We feel comfortable looking at a one‐page menu, especially if we are sitting across the table from someone we are trying to engage with. It can feel overwhelming—I get it.

Understanding this psychological phenomenon when heading into the world of side hustling can help you avoid falling into one of the two traps listed earlier. Analysis paralysis prevents most people from engaging in the gig economy, overthinking the choices you could have made, or wondering if the one you did was the “right” one.

I want you to approach side hustling with an open mind. We're going to look at how to approach such a bustling and expansive industry so that you feel content, fulfilled, and confident in the decisions that you've made.

Breaking Down the Time You Have

When choosing what side hustle makes sense for you, the very first thing you should do is a time audit. Sit down and go over where you have pockets of free time in your days. Maybe you have a couple of hours hanging out in the morning, or a long lunch period. Maybe you get off from work at 5 p.m. and don't really have anything else to do before you fall asleep at 1 a.m. after bingeing Netflix. Maybe you have completely free weekends, or maybe you are a single parent trying to somehow make all this work with a child at home.

First, write down your estimate of the available time you have each day of the week. Once that's done, add it together for a grand total. Don't worry, even having just three free hours throughout the entire week can still lend itself to productive side hustling.

Now, I am going to push you out of your comfort zone. Ready? You are going to map out how you spend the rest of your time each day, down to 30‐minute intervals. You may think you are busier than you actually are. I wouldn't be me if I didn't give you all a little tough love in this book. Write down how much time you spend sitting on social media, playing video games, watching Netflix, or, yes, even commuting (the remote work economy does not require commuting, saving participants dozens of hours every month).

This book is not designed to be part of that toxic hustle culture where writers encourage readers to hack their productivity and basically never have a social life again. I am merely asking you to become aware of how you spend your time. Let's say you estimate spending about 14 hours every week on social media and playing video games. My rule of thumb is trying to cut that 14 hours in half. That way, you're still leaving an hour every day for one of your time wasters, yet you have seven new hours you can now use on a side hustle. With seven hours used every week, you can manage just about any side hustle.

Add this new amount back to the amount you totaled at the top. I am going to guess your original total was around seven or eight hours, and it's now at the 15‐hour mark. Good! The more time you can set aside for side hustling, the better.

Over time, once you master your side hustles and learn how to leverage software, chatbots, and virtual assistants to replace you, then you, too, can enjoy that four‐hour workweek.

Analyzing Your Stomach for Risk

When compared to other forms of investment, side hustling in general is not particularly risky. Still, the risk required for different side hustles can vary greatly, which is why you want to think about how much of a risk‐taker you really are.

When I was first starting out in the gig economy, I had zero stomach for risk. That's why I started with the least risky thing of all: freelancing. I did nothing but freelance for years. I didn't want to rock the boat. But, as I learned more and more about how money grows and wealth is accumulated, I realized some risk is required to really make that money work for you.

I started with less risky side hustles, like selling an ebook I wrote myself (saving the $500 cost associated with paying a freelancer to do it for you) and taught myself how to upload it to Amazon Kindle Publishing. Another year went by, and I finally decided to onboard my first freelance writer. Still, another year transpired, and I finally started to sell online course packages that I filmed with a videographer. It wasn't until 2020 that I really went for it with the “riskier” investments, like dropshipping/ecommerce and cryptocurrency.

Let's break down the 10 side hustles listed in Chapter 9 based on my perceived risk levels associated with them:

• Risk Level: Easy
  • Online tutoring: Freelancing is as risk averse as it comes.
  • Starting a blog: You can do this very cheaply if you make the blog yourself and buy a domain that's only $12–$50 for the year.
  • Launching a podcast: You can do this by signing up on a site like RSS.com for free and talking straight to your laptop or phone using a software like Audacity. If you want to hire audio editors and graphic designers to make your cover art, that can increase the “risk” associated with it.
  • Become an influencer: It has cost me $0 to become an influencer. It's hard work and requires consistency, but it costs nothing. All you need is a smartphone.
• Risk Level: Moderate
  • Selling Online Courses: Considerable production goes into selling online courses, so either plan to partner 50/50 with a videographer, or set aside some money to make this happen. You will then need to market the course to get sales.
  • Selling ebooks: If you outsource the writing/formatting of the book, ebooks can cost a moderate amount of money. You need to then market the ebooks to get sales.
  • Launch a YouTube Channel: You technically need a smartphone and a YouTube account to make this happen, costing you nothing. But, if you want to really leverage the account and make some serious sponsorship dollars, you will need a fair amount of electronics and some assistance with video editing.
  • Become an Affiliate Marketer: Running paid ads to your affiliate marketing campaigns can come with some risk if you are not familiar with managing ads online.
• Risk Level: Hard
  • Starting a Dropshipping Business: You will have to front the most amount of money when compared to other virtual side hustles. From time to time, you will also be communicating with suppliers that may have problems with communicating in English.
  • Becoming an Airbnb Host: Buying investment properties comes with a slew of risk. Yet, when done correctly, real estate + Airbnb can be a double investment that quickly sets you financially free.

These risk assignments are not permanent per side hustle. If you go with the DIY approach, many of them can be done for close to no money. It's up to you how “risky” you want to be with your initial investment dollars.

Identifying What Will Make You Happy

This isn't all about the money and financial freedom. Sure, those are some nice side effects, but this isn't corporate America. You can do what you want to do for a living. You can manage a side hustle that makes you feel fulfilled based on your personal interests, skill sets, and personality. You know the old saying: do what you love and never work a day in your life. That saying, from my experience, could not be truer.

How can you analyze your personality in a way that helps you pair up with the right side hustles? Instead of breaking this down in an introvert‐vs.‐extrovert way (I very much dislike how people use their self‐identification as being introverted or extroverted as crutches when pursuing things today), let's look at some of the major personality traits needed to be successful in different kind of hustles:

• Verbal/In‐Person Customer Service: Side hustles like being an Airbnb host and working with dropshipping suppliers is going to require you to be able to make a phone call and communicate with authority to the other person on the line. It may even require you to meet up with clients/partners in person.
• Virtual Customer Service: Freelancing is hugely based on virtual customer service. Being able to communicate with polite efficiency and proper email etiquette is important for freelancing and dropshipping/ecommerce clients.
• Marketing/Social Media Marketing: Being able to create marketing campaigns, content, and concepts is a very creatively demanding endeavor: ebook sales, course sales, and influencing reach are largely based on marketing.
• Sales: Cold, hard sales pitches, landing pages, and outreach can be part of affiliate marketing, freelancing, and even blogging when reaching out to partner with other bloggers.
• Editing/Refined/Detail‐Oriented: The finer, more intricate details are a massive part of managing a successful blog (no typos allowed), editing ebooks if you write them yourself, and video editing/script writing for YouTube.
• Front‐Facing Filming/Audio: Podcasting, influencing, some forms of affiliate marketing, YouTubing, and filming online courses require you to get on camera. Fear not, if you have no prior experience doing this; remember, we all started at the same place.

Putting It All Together

Based on the personality attributes you consider yourself to have, you should be able to identify a few different side hustles that best align with your psyche. Remember: this is just my initial list of 10 proven side hustles based on my personal experience. There are so many other side hustles you can consider and bring through the process here when identifying if they are right for you.

After going through this three‐step process, breaking down your time, analyzing your stomach for risk, and identifying your personality traits, a few side hustles above should be jumping out at you. Consider more than one side hustle when starting out—you may find yourself loving the side hustle you initially ruled out.

Regardless of the available time you have for your side hustles every week, time management is going to be incredibly important for maximizing every extra minute you have. Let's look at time management expectations so that you are not caught off guard when becoming an official side hustler.

Chapter 10 Key Points

• Every person is different when it comes to side hustles that are right for them.
• Start by calculating your available time every week.
• Analyze your stomach for risk and how much money you want to initially invest.
• Spend some time identifying your unique personality traits and how they align with the available side hustles.