5 Signs You’re Ready for a Side-Hustle

Jenna Kutcher 

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February 1, 2024


The buzz word ‘side-hustle’ has become a hot topic in today’s world. It’s inspired many anti-hustle activists and woven its way into countless books, courses, movements, and key note speeches. And while we’re all dreaming of leaving that exhausting hustle culture behind, one thing is clear: people crave ways to have work they love doing. Why waste your life doing anything else if the option is possible?

So, if you’ve been feeling that itch to explore what a ‘side hustle’ could look like for you, how an extra income could change your life, or how to monetize your skills and turn your hobbies into income, you’re in the right place. Are you ready to start a side hustle? How do you know when you’re actually ready to launch a side gig rather than just dream about it or keep it on that “someday” list? There are a million ways to start piecing this puzzle together, and I even created a free quiz to help you find your Side Hustle Personality to get you started!

Let’s get you on the right track by exploring 5 signs that help you know when you’re truly ready to start moving away from giving your all to the 9-5 work grind and creating your own side hustle! And if you already KNOW you’re ready to start a side hustle, check out this post that guides you through how to start!

01) You Dream about Turning Your Hobbies Into Your Full-Time Job

Would you describe yourself as a multi-passionate person? You might find that you’re always up for learning something new, taking a class, picking up a new skillset, and getting the itch to ‘make something’. Does it give you a spark of inspiration when you imagine being your own boss? When you think about getting to explore those avenues and skillsets however you want to because you’re the CEO, does your heart skip a beat?

If you can’t stop thinking about doing what you love (whether that’s one thing or a handful) as a full-time job, you’re very likely ready for a side hustle.

02) You Want to Have Multiple Streams of Income

A successful side gig does more than scratch your itch to be your own boss. It also allows you to monetize your skills in a variety of avenues which means limitless streams of income… which means your financial goals are in your hands. You can step away from that cycle of waiting for a raise and enter into being in control of your own revenue flow. Even one side job can mean a massive shift in how you contribute to your income and being able to live the life you want.

Are you excited about potential extra income strategies and feeling hungry to see how they could impact your life? If being able to control your own earning potential excites you, a side hustle is a great move for you!

03) You Want Your Creativity to Fuel Your Work

Picture this: You’re a creative visionary, clawing at the seams to find more fulfilling ways to use your creative energy and ideas in this world. You dream about a job that gives you FULL creative license and unleashes you, unbound, to make whatever you’re inspired to make. You dream about creative workflows and a job without rigid work hours that stifle you. You want to share your passion with the world in authentic ways, your own ways, rather than someone else’s.

Does that sound like you? If the idea of being creatively set free and generating an income from that sounds like a dream come true, start a side gig could help you turn this dream into a reality!

04) You’re Tired of Trading Time for Money

This was the overwhelming desire that I had when I walked away from my own 9-5 corporate job in a windowless office after way too many years of burnout. I wanted to start a profitable side gig to prove to myself that I could bring in an income without having to give so many of my hours away. Are you desperate for more energy, time, freedom, and flexibility? Are you tired of the same ol’ cycles of burnout, living for your time off, and dreaming about retirement?

If you’re wanting to take back control of your time and actually create a business that makes money for you while you rest, create, and LIVE, a side hustle can be the perfect starting point.

05) You Want to Control Your Growth and Life Path

You’re feeling uninspired about the life path set before you. At the very least, you know it could be… better. You know it should excite you and feel more like you. You have those big goals for the future, and you’re ready to start doing the work to get to them, because the steps you’re taking now might never get you there. In fact, you’re realizing that you’re going to hit someone else’s glass ceiling or have your life planned out for you if you don’t matters into your own hands.

Are you craving control of your life story? Do you want to know without a doubt that the pen is in your hands as you take back ownership of your journey? If you’re ready to start charting a more authentic course, you can start making a shift in small, meaningful ways with a side hustle.

Knowing If You’re Ready to Start a Side Hustle

As we look at these signs to see if you’re more ready than you thought to launch a side gig, I know that big resounding ‘YES!’ also has you hoping for an even clearer next step. Where do you really begin with a side hustle? Because the way forward can seem confusing. Juggling the work you’re doing now with the business you’re building can be tough. It can feel so risky. It can be exhausting, especially in the transition, and make you wonder if you’re actually cut out for it. How can you know if you’re able to turn your side hustle into success?

The secret is that you can’t know. But in all of my years of entrepreneurship and helping people take those dusty dreams off the shelf and actually LIVE them, I’ve learned this: starting is 90% of it. So many people will have this itch, know they want to start building their own dream… but they won’t do it.

Fear of failure, of shame, of looking cringey, of simply not knowing the outcome could be what holds you back from everything you want. Your first step is to trust that you know it’s what you want. To see these signs, whether you can tick off just one of them or all five, and believe that they’re reflecting the truth that you’re ready to try at this whole side hustle thing, even if you can’t predict the outcome. In my experience? The outcome has been 1000% times better than I could’ve imagined it the day I walked out of my corporate job for the last time.

What’s Your Side Hustle Personality?

Take my Free Quiz to Find Out!

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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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