Chapter 8
Supplement Your Job to Explore New Opportunities
Slash careers. Side hustles. 20% projects. Whatever you choose to call them, more people than ever are supplementing their primary jobs with a second gig. In fact, according to a 2018 Bankrate.com report, nearly 4 in 10 Americans work more than one job.1
Extra cash isn't the only reason why people are increasingly pursuing side hustles. Many side hustlers use additional projects to fulfill their creative needs. For example, I've met people who have started photography, writing, and Etsy businesses on the side to develop artistic talents that they don't use in their regular day jobs. Other side hustles serve as testing grounds for potential full-time gigs. In his book The 10% Entrepreneur, author Patrick McGinnis highlights many successful business leaders whose ventures began as side projects, including Luke Holden, founder of the popular seafood chain Luke's Lobster.2 Holden initially launched the business while working as a Wall Street analyst. What began as a 200-square-foot hole-in-the-wall lobster shack has since grown into a global enterprise that generates tens of millions in annual sales.
The Perks
Side hustles might be an attractive and highly effective strategy if you are looking to gain more satisfaction in your professional life. Among the many benefits, supplementing your current job can allow you to:
- Safely Test Drive New Areas: Quitting your job to explore new areas may be extremely stressful and financially infeasible. But by pursuing a side hustle, you can try out new career paths or passions with the safety and security of your existing job. This way, you don't have to worry about making money immediately and can simply focus on whether you enjoy other key elements of the work.
- Explore Entrepreneurship: Starting a side hustle can provide you an opportunity to explore whether you would like entrepreneurship and being your own boss. We all hear about the potential upsides of owning a business, but starting a side hustle allows you to see for yourself, in a relatively risk-free environment, whether you would enjoy the ups and downs of overseeing all aspects of a business.
- Gain New Skills: Taking on a side hustle may allow you to gain new skills that you are unable to build or hone in your day job.
- Satisfy Unmet Job Needs: In Chapter 3, you analyzed the key job areas for your existing role. A side hustle may allow you to address those areas that were less positive – some of which may be impossible to improve otherwise, based on the realities of your role, organization, or industry. For example, if you dislike the basic content of your job but enjoy other aspects, you may be able to find a more engaging subject matter through a side hustle.
- Earn Extra Money: In the long term, taking on a side hustle allows you to explore new areas and gain real-world insights into which paths may be most viable. But in the meantime, your side hustle may also allow you to supplement your income so that you can improve your quality of life or help achieve your personal financial goals.
- Meet New People: A side hustle can also allow you to expand your network. In particular, you'll likely develop new connections both online and in person through the process of researching, building, and marketing your side hustle. These new contacts could become mentors, partners, allies, or even friends.
- Diversify Your Life: Adding a side hustle allows you to diversify your life, which may help you reduce your exposure to just one employer. That's important because putting all of your eggs in one basket can be risky from both a financial and an emotional perspective. For example, if you are receiving negative energy or feedback in your day job on a particular day, other activities may help you feel more balanced and even-keeled, decreasing the likelihood of experiencing severe lows.
Now, Some Practical Points
While there are many benefits to starting a side hustle, you should consider certain practical points before hanging up your shingle. In particular, keep in mind that in a side hustle:
- You Need Time: Blogs and articles often make having a side hustle sound so easy. But the truth is, researching, building, and marketing a new venture takes time. Extra time is something most of us don't have, so you'll need to create a schedule of your typical week and then ask yourself:
- Which of the activities that currently take up my time are required (such as working my day job or spending time with my family), and which ones are voluntary (for example, binge-watching Netflix shows or playing fantasy football)?
- Which voluntary activities would I be willing to forgo in order to pursue a side hustle?
- Am I efficiently using my time right now? Are there ways I can fit in a side hustle without devoting less time to my current personal and professional activities? (For more tips on this topic, refer to Chapter 15.)
- You Won't See Immediate Results: While you'll need to commit a certain number of hours each week to your side hustle, you won't see immediate results or receive positive reinforcement right away, which can be frustrating. Some of the most successful bloggers often talk about how when they originally launched their sites, they had maybe 10 visitors to their sites a day, which consisted of their own visits and some family.
- You May Need Extra Money: Starting a side hustle often involves a number of steps. For example, you may need additional training before you can begin actually side hustling in your target area. Even when you attain the necessary qualifications to begin a venture, you may need to cover certain administrative costs, such as buying a website domain name and hosting services for your website, printing business cards, investing in advertising, and registering your business, among other costs.
- A Side Hustle Shouldn't Threaten Your Current Job Prospects: One of the benefits of the side hustle route is that it provides you the opportunity to experiment professionally while still enjoying the stability of a regular paycheck. A key to making this strategy work is to avoid activities or commitments that would jeopardize the security of your day job. That means:
- Prioritize your day job first. Make sure you're still completing your tasks well and on time.
- Don't use your company's resources to benefit your side hustle. For example, refrain from working on your side hustle while at the office, using your work computer for your side hustle, or advertising your side hustle to work clients.
- Check your company's code of conduct, conflict of interest, communications, and moonlighting policies, to make sure you understand the in-bounds and out-of-bounds activities for your potential side hustle.
Getting Started: Figure Out What to Pursue and Make It a Reality
Launching a side hustle begins with quite a bit of research, reflection, and planning. Although this stage can feel tedious, it is arguably the most important part of the process. By carefully considering the many factors that will impact your side hustle, you will be able to identify foreseeable deal breakers and obstacles before getting too far along. The prelaunch phase includes the following steps.
Determine Your “Why”
Define what you want from a side hustle by thinking about the following:
- Purpose of Side Hustle: Is the purpose of launching a side hustle to 1) fulfill unmet job needs, 2) explore a new professional area, 3) earn extra cash, 4) a combination of the above, or 5) something else?
- Type of Side Hustle: Do you hope to make enough money from your side hustle to cover your operational costs plus perhaps a little extra (i.e., a hobby), or do you aspire to eventually replace your day job income with your side hustle earnings?
Explore Areas to Pursue
With your “why” in mind, you can start exploring the many possible paths for you to pursue. Some people may already have a side hustle they've been thinking about for a long time, and know they'd like to pursue that area. For everyone else, the following factors can help you focus on a few areas:
- Reflect on Your Past Work: You may be able to leverage a lot of the work you've already done in Chapters 3 and 6, where you identified missing elements of your current role, as well as the elements of your ideal role. Refer back to your work so you can refresh your memory on the interests and skills you pinpointed that are important to you, as well as topics or subject areas in which people often come to you for answers. Review what books, articles, or blogs you read in your spare time. All of this past work can give you hints about potential focus areas for your side hustle.
- Find Existing Case Studies: Next, you can perform online research to learn about types of side hustles from relevant industries that have proved successful. This approach may be especially important if you are embarking on a side hustle with the hope of creating a long-term business that eventually becomes your full-time job. Remember that a side hustle could either be broad in nature or highly specialized. Some examples of broad-based side hustles include blogging, freelance writing, consulting, teaching, tutoring, and advising – all of which you could customize for one or more areas of interest. Other side hustles focus on a single subject area or vertical, such as rental real estate management or fashion design.
- Explore Business Models: As you consider what area to pursue in your side hustle, you'll also want to figure out how you'll make money. Generally, you can generate revenue by: 1) selling your products, 2) selling your services, or 3) selling other people's/companies' products or services. Refer to Table 8.1 for some examples of these business models.
Consider Your Funding Strategy
Nearly all side hustles require at least some upfront financial investment. Once you've determined the area(s) you'd like to pursue, you will need to estimate how much your side hustle will cost on an upfront and ongoing basis. You can do this in several ways, including:
Table 8.1 Potential Business Models for Side Hustles.
| Business Model | Examples |
| 1. Sell your products. |
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| 2. Sell your services. |
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| 3. Sell other people's products or services. |
|
- Search the Internet: I've found that running a couple of targeted online searches is typically a good starting point for estimating your costs. Often you'll find several articles outlining startup costs for various types of side hustles, based on other people's firsthand experience.
- Reach out to Industry Experts: After completing some preliminary research, you may wish to contact other people who have successfully launched the types of businesses you're considering. Reaching out to industry experts can help you verify your online research, improve your understanding of the likely costs, and even provide you tricks or tools for funding your business. I took this very approach when I was considering whether to launch my financial planning firm. After conducting a lot of online research, I contacted several financial planners in New York City to learn about the process they went through to fund and develop their business, the amount of time it took, the service providers they used, and any other helpful tips they would be willing to share.
- Enlist a Business Coach: When starting a new venture, a business coach could help you decrease the amount of online research you need to do to get started. In addition, coaches can brainstorm your potential venture with you, and for ongoing relationships, hold you accountable. Once your business is started, a coach may be able to give you suggestions on how to streamline your operations, and help you think about how to expand to new markets or clients.
Take Action
While you may have researched multiple side hustles, you should be ready to choose the initiative that most excites you now and is also viable. Since you'll already be taking away time from other personal activities, it's best to start with one side hustle and see how it works within your life rather than attempt multiple ventures. Evaluating your interest in a particular side hustle is much more difficult if you're stressed, overextended, and burned out.
Once you've selected a side hustle, develop a six-month to one-year plan that outlines what a “good” outcome looks like for you at the end of your initial testing period. A “good” outcome could include a concrete or quantifiable goal you would like to achieve, such as a revenue target, client goal, or education and skills milestone. Make sure to translate your large goal into bite-sized actions that you can complete on a weekly or monthly basis.
You'll also need to find the time to work on your new project. At a minimum, you should aim to work on your side hustle several hours a week. For me, on the weekdays, early mornings between 7 and 9 a.m., and after work between 6 and 8 p.m., are when I've mentally made time for my various side hustles. I prefer working on my side hustles in the early morning because I typically am relatively refreshed from the night before and reactive requests or fire drills have not come in yet from my day job. On the weekends, I typically spend a couple of hours in the morning at a coffee shop working on my side hustle. This small amount of time has allowed me to try out real estate, freelance writing, financial planning, and now, writing a book!
Use Table 8.2 as a guide to get you started on mapping out your side hustle (also available at www.workyourmoneybook.com).
Table 8.2 Sample Side Hustle Six-Month Plan for Real Estate Agent.
| Six-Month Goal |
|
| Monthly Actions/Goals | |
| Month 1 |
|
| Month 2 |
|
| Month 3 |
|
| Month 4 |
|
| Month 5 |
|
| Month 6 |
|
| Side Hustle Working Time | |
| Weekdays |
|
| Weekends |
|
| Where Will Time Come From? |
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| How Will You Make Sure You Stick to Your Plan? |
|
Evaluate and Make Adjustments
You're not going to like every activity you participate in, which is totally natural. The great thing about side hustles is that they allow you to dip your toe in the water of potential interest areas and gain a better sense of the day-to-day skills required to be successful, without needing to take the risks that a job change typically requires.
In order to maximize the benefits of a side hustle, you should reflect on your feelings periodically and make adjustments as necessary. That might mean deciding that a side hustle that you originally thought could someday be your full-time job would be better as a hobby. Or you might choose to ditch the side hustle entirely because you've realized you don't enjoy it after all.
Brock McGoff – founder of the Modest Man, a website dedicated to helping shorter men dress better – tried a side hustle in music production and developed a number of websites, before pushing forward with the Modest Man concept. He says, “Building niche websites was a great way to learn about content development, but I wasn't passionate about any of them. I was just working on those particular sites for the money, which I realized wouldn't be sustainable or fulfilling in the long term. As I started to get more into menswear and dressing better, I decided to create a website with content around what I would have wanted to read about men's style.” After working on the site for three years as a side hustle, McGoff made the leap and turned the Modest Man into his main gig – and he hasn't looked back since.
Alternatively, you could start off by pursuing a side hustle as a hobby, discover unexpected success, and eventually consider whether to make it your full-time job. That's exactly what happened to Jim Wang, who created a personal finance website called Bargaineering in 2005 while working as a software engineer. “I always had an interest in personal finance and how it worked, so I started the blog to help me understand it. I never thought it'd become something that other people would want to read.” But within just a couple years, Wang saw his Bargaineering earnings climb to $30,000. The website's rapid growth prompted Wang to rethink whether he should pursue Bargaineering as “just a hobby.” By 2008, with the site generating six-figure earnings, Wang decided to make Bargaineering his full-time gig. “When I was thinking about whether to go all-in, one concern was how long blogging as a business could last,” Wang explains. “But I decided that regardless of the staying power, I would look back with regret if I didn't devote all of my energy to growing the site.” Five years after launching Bargaineering, Wang sold the site for a multimillion-dollar payout. He is now developing another personal finance-focused website called Wallet Hacks.
Neil Pasricha, bestselling author of The Book of Awesome and The Happiness Equation, and Director of the Institute of Global Happiness, also saw his side hustle evolve over time in unexpected ways. He began writing and speaking while serving as Director of Leadership Development at Walmart. Initially, Pasricha had no plans to transition either side hustle into a full-time gig. He explains, “Writers write something like 1.1 books on average, so after I finished my first book, I thought that would be my 15 minutes of fame – end of story. When it came to speaking, I had heard that the average speaking career lasts about six years, which sounded way too short to quit a steady day job. I also appreciated the benefits that my day job provided me, including a sense of structure and a place to socialize with others.”
But Pasricha's feelings changed after six years of writing and speaking on the side. He reevaluated his situation and ultimately decided to leave his job at Walmart in order to give his side gigs his full attention. Pasricha says, “Part of my decision was personal – having kids took time away from nights and weekends when I would typically work on my writing and speaking. And part of my decision was seeing the viability of both – after writing five books and participating in 150 speaking engagements, I thought I could actually do these activities for a living.”
Deciding Whether to Go All-In
While many of the stories highlighted involve people who eventually turned their side hustles into their full-time jobs, the decision to make that leap should not be taken lightly. Many did so only after balancing their day jobs and side hustles for several years, and Pasricha believes there are many benefits to doing this balancing act as long as possible. “I believe having multiple things going on somewhat counterintuitively enables you to take more risk in each! For example, if you have a weekend wedding DJ business that you could see yourself leaning into, you might feel more empowered to speak up at your day job, which, of course, helps you get noticed and promoted more. And if you have a day job, then you may feel free to take more risks in your art.”
Financially, you'll also want to run the numbers to evaluate whether turning your side hustle into your main gig is feasible. Ask yourself the following questions:
- Do the net revenues from your side hustle cover your living expenses, which you outlined in Chapters 4 and 5? Make sure to adjust your living expenses upward for any expenses that may be artificially lower because of your employee benefits, such as health care costs.
- In a base case scenario, staying on your current trajectory, where would you shake out with net revenues in one year? What would net revenues look like in the best-case scenario? What about in a worst-case scenario?
- What if you quit your job, make your side hustle your full-time job and the worst-case scenario happens – what would you do? Can you stomach that worst-case scenario?
Notes
- 1. Amanda Dixon, “The Average Side Hustler Earns Over $8k Annually,” Bankrate, June 25, 2018,
https://www.bankrate.com/personal-finance/smart-money/side-hustles-survey-june-2018/ - 2. Patrick J. McGinnis, The 10% Entrepreneur: Live Your Startup Dream Without Quitting Your Day Job (Portfolio 2016), 43–45.