Many people ask Craig and me, “How did you step away from your traditional jobs in your twenties and thirties, respectively?” Our answer: intentionally. Our experience is that most people lack real clarity on what they truly want and are often unwilling to plan, commit, and clear enough things of lesser importance out of their life to genuinely create it.

Through our side hustle journey, it dawned on us that there’s not enough guidance out there for side hustlers specifically– those who have to keep their career afloat, manage their life, all while navigating building a business. Thus this article and our book, So You Want to Start a Side Hustle.

My thought process began to shift as I was transitioning from collegiate life to adulting. My dad wined and dined me (meaning he fed me pizza) and emphasized the importance of having more than one way to make money. It was casual but cautionary, and his advice connected the dots for me that if I genuinely wanted to create an exceptional life, I had to go out of bounds on the mainstream “go to school and get a good job” adage. Since I was not hardcore enough to quit my job and attempt to gut out a startup, nor did I have genuine business expertise, I instead jumped into the world of 𝒎𝒐𝒅𝒆𝒓𝒂𝒕𝒆 𝒆𝒏𝒕𝒓𝒆𝒑𝒓𝒆𝒏𝒆𝒖𝒓𝒔𝒉𝒊𝒑, meaning I launched my first wave of side hustles.

Fast-forward into my thirties, and that approach allowed me to walk out of my career four decades sooner than had I taken the conventional path, being able to travel the world, experiencing life as an adventure, and creating a home life with our children that I wouldn’t trade for anything. And most important, it’s given me the opportunity to invest in others in a way I had always hoped for, as my goal was never just to make a bunch of money, but to create significance.

It’s one thing to start a business, but the biggest rewards and benefits of building a side hustle come from actually building it. For many, it’s not the initial honeymoon excitement that presents the challenge; it’s the follow-through. It’s the lack of conviction and true commitment that it takes to build something substantial. The reason most people fail in building a side hustle is that they treat it like one.

The following list gives reasons why we encourage you to dig your heels in and fully embrace the side hustle movement for the long haul.

1. Diversifying in the Twenty-First Century Should Be Non-Optional

People say starting a business is risky. Have you ever met a financial planner who advised you to put all your money into just one stock? The answer is hell no, so why put all your eggs into one basket when it comes to your income? Also, asking for your full-time job to fulfill all your financial needs and career development is like expecting your life partner to complete all your emotional needs. You have relationships in your life outside your spouse for a reason. Remember: one of the only guarantees with a job is that someday you will not have it!

We believe going through life with only one way to make money is risky, and having only one way to make money in the twenty-first century is arguably irresponsible.

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2. Building a Side Hustle Can Create More Time for Your Future Self

Once we learned about the concept of building assets that can create passive or ongoing revenue, our mindset completely shifted. What are you doing or building today to create more time, security, and peace of mind for yourself in the future? Building our side hustles large enough to replace our 9-to-5 jobs required additional time investment upfront for several years, but it has been infinitely worth the rewards. We didn’t want time to be our excuse for not building our side hustles, so time became the reason we built them.

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3. Developing New Skills Is Critical for Your Financial Security

Acquiring new skills is one of the most paramount things you can do for your financial future and can play a major role in your happiness. For most people, the first few years in their new careers can provide a big learning curve. However, even with a promotion or two, the learning curve tends to dissipate. It’s not that you aren’t learning; it’s that you typically aren’t learning as much, and oftentimes the subject matter or expertise narrows. The drawback with most jobs is they can’t challenge you in all the ways you want to be challenged. Building a side hustle pushes you out of your comfort zone and has you developing new skills that you wouldn’t otherwise.

For instance, when my husband Craig (the stud in the photo above who uncannily looks an awful lot like the photo of Neil Patrick Harris below) was working as a risk analyst for a Fortune 50 company, there was not exactly an abundance of public-speaking opportunities, and he always labeled himself as more of an analytic than a sales guy or public speaker. However, building a side hustle forced him to start developing these skills, which in turn transferred into his career, allowing him to move into business development, doubling his job income. These skills boosted his public-speaking career, a passion, and ability he would have never developed if he had just been crunching numbers in corporate America. I can also attest to boosting my skills above and beyond what my teaching and athletic coaching background could provide as a function of entrepreneurship. This mindset and momentum around skill development still continue to this day, and so have the benefits for both of us.

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4. You Enhance Your Financial Education and Your Understanding of How Taxes Work

Most people are taught language, academic, or job literacy, but they are not required to attend classes on financial literacy. [Insert joke about the long-term value of my Women & the European Fairytale and Physics for Poets collegiate courses]. Financial literacy hones a deeper understanding and application of budgeting, investing, and overall personal financial management.

Learning how the tax code works and how you can leverage it in your favor is a game-changer for most side hustlers. Even if you don’t make a dime from your side hustle and run at a small loss for a few years with a home-based business, the amount of education and deductions you can capture is of value and can offset any manageable losses. Use a side hustle to break free of being intimidated by the tax code and learn how to use it to your advantage.

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5. A Side Hustle Forces You to Grow Your Entrepreneurial Network, Enhancing Your Leverage

We can attest to your network equating to your net worth. It’s not exactly a 1-to-1 ratio, but there is a huge correlation. Think about it, how did you find your first job? If you are going to find another one, how would you start? Imagine the value of building out your network into new industries, arenas, or spheres of influence. A side hustle challenges you to put yourself in front of people you wouldn’t otherwise. If you do quality work and develop authentic relationships, it amplifies your network and influence. Developing your networking ability is a cornerstone skill, and many job roles never provide an opportunity to do this, or if so, only in a limited industry-specific capacity.

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6. A Side Hustle Can Be a Lifeboat During Economic Changes and Disruptions

The need to navigate the exponential growth of technology, artificial intelligence, and other economic uncertainties, is more certain than ever. It’s paramount that you challenge the way you think and be realistic about the impact technology has already had on the way we work—eliminating positions as well as creating entirely new industries. Because of things like tech and AI, you cannot count on the continued existence of your domain or industry, or your function within them. Planning now for what might be inevitable will help you avoid getting stuck as a “specialist,” clinging to a skill or industry that might soon be obsolete, or one that already is. Building your side hustle will help you become more dynamic when it comes to finding work in the future.

Check out our Tandem Talks Podcast with guest, Frank Mengert, as he shares his inspiring story of converting a job layoff into going all-in on his side hustle!

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7. Building a Side Hustle Develops Your Personal Brand

Your personal brand now carries more magnitude than ever before. Back in the dark ages (the 1980s), there were only a handful of major television channels, radio stations, and so on. Now we have thousands of different ways to market not only a company but you. You, as a already exists. The only question is what does that brand sound, feel, and look like? So how does having a side hustle help? We believe entrepreneurship is one of THE best forms of self-development. When people begin to think of you as someone who is growth-oriented and willing to improve themselves, they have a harder time putting you in a box! If you do this through honesty and good, quality work, your branding improves. In addition, you can always take your brand with you, even when you leave a job, company, or industry. It’s an asset, and we recommend taking it seriously. 

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8. For the Adventure and Bloody Love of the Game (My Personal Fav)

If you are reading this article, you may be craving some additional adventure in your life. There is likely a desire for another challenge or a new experience, or at least to have a chance at a financial home run (also giving you the thrill of possible failure). Everyone craves these things; it’s just in the intensity, frequency, and duration of the adventure that people might differ. Starting your side hustle definitely gives you a renewed sense of excitement in your life. We highly recommend doing things that help you grow and make you feel alive.

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So What on Earth Does This Have to Do with You?

Potentially nothing, but if you have read this far, potentially a lot. We believe entrepreneurial desire, interest, and talent lie on a spectrum. The vast majority of people are floating in the middle; the ambiverts of entrepreneurship. They are not die-hard, risk-taking business owners, nor are they 100 percent fulfilled or secure in their full-time careers. And they know more is out there.

People are waking up to the fact that there is less job security than ever, but there is also more opportunity than ever. The pandemic has played a huge role and people are shifting their priorities, especially as it relates to their careers; a shift the NYTimes has called the YOLO economy. Can you relate?

Everything we have built started out as a side hustle or still is. What we share in this article and our book is relevant because we have lived it. It is not theoretical, statistical, or academic, but an authentic testament of how powerful progressive, incremental growth can be and how deeply rewarding a side hustle approach can be when you activate. We hope you are empowered to think bigger and bolder about what is possible for you!

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