Side Hustle Shuffle: The Common Sense Guide to Your Own Side Hustle
May 2014

Side Hustle Shuffle: The Common Sense Guide to Your Own Side Hustle

Have you ever considered turning to working for yourself as a way to build your wealth, improve your career, and boost your personal happiness? If not, please allow me to encourage you to spend some time thinking about the possibilities that entrepreneurship offers.

No worries: you don’t have to jump off the deep in and launch a million-dollar start-up with an army of hip young employees by tomorrow. The common-sense way of handling big, exciting changes is to take it in pieces. Baby steps, people!

Start small, follow the way of the solopreneur, and consider doing the Side Hustle Shuffle.

Side Hustle Shuffle? Indeed! Allow me to introduce this new Common Sense Millennial series, in which we’re going to be looking at the benefits of side hustling, how to start your own hustle, what to do with that extra income, how to grow your side career, and a whole lot more.

Have a specific question about side hustling, solopreneurship, or running a digital business? Be sure to leave it in the comments here, and your question may be featured in a future Side Hustle Shuffle post!

In the meantime, we’re going to kick this series off by covering the basics for those who are brand-new to the idea of side hustles and developing a sustainable, profitable business that allows for an abundance of personal freedom and happiness.

What Is a Side Hustle, and How Do I Get One?

A side hustle is pretty much what it sounds like: part-time work that you do on the side of your full-time job. Your hustle can be anything – really! What you do for your extra income (as long as it’s legal, moral, and ethical) can be whatever you want it to be.

Of course, the countless options available to you can make it hard to narrow down your focus when you’re wanting to establish your own gig on the side. For the best chance of side hustle success, you need to come up with something to offer that hits these three crucial points:

  • You’re good at it
  • You enjoy doing it
  • You know people would be willing to pay you for it

The ideal side gig for you will be one that intersects all these aspects at once. Why does it matter if you’re good at it? Because it’s work you’re doing on the side – which means in addition to work you’re already doing for your full-time job. It’s unlikely that you’re working your dream job (and that’s okay), so to avoid burnout you’ll want to choose some sort of gig that feels more like play.

Equally important is that you’re pretty darn good at what you do. Whether you’re working with people face-to-face or putting out your digital shingle online, the world is a crowded place. It’s loud out there, which means it can be difficult to get your voice heard.

Simply being good at what you do is going to make you stand out. You don’t have to reinvent the wheel or come up with innovative ideas no one else has ever had (at least, not constantly). The key to being memorable and likable – and therefore, hire-able – is just being yourself.

It’s also the key to getting started with a side hustle. So many people stall out because they can’t get past the thinking and brainstorming part. They can never come up with an idea for their own side hustle because they don’t realize that they already have all they need to get started.

That’s your unique angle, your unique totally new idea. It’s you! No one can do something quite the way you can. No one thinks just the way you think.

You can’t please everyone, and you shouldn’t try to. Just like you can’t expect to like or be best buddies with everyone you meet, in the side hustlin’ world, you can’t expect to appeal to every single potential customer. It’s okay to be you, because there are people out there who you will please naturally, and people who will find your personality, communication style, and way of doing things really appealing to the way they work.

That’s why being yourself is truly what makes you stand out – and not having the next big idea (of course, if you do, run with it). There are a million writers in the world. I’m one of them. And I’m the only one who has my own voice, which is part of the reason people hire me to write for them, or to help with their marketing efforts, or to manage their content.

Your unique perspective, experience, and voice will be why someone who didn’t want to hire me wants to hire you.

Why Bother with a Side Hustle?

The best answer to this question is, why not? There aren’t too many downsides to side hustling. But for the sake of this informative post, let’s look at why you should start your own side hustle as soon as you finish reading.

Extra Income. The biggest, most obvious advantage of a side hustle is the fact that when you start earning, that income is a little something extra. What would you do with $100, $200, even $500 or more extra per month? You could pay off debt faster, take that big trip abroad you’ve been dreaming of, or boost your savings and retirement contributions.

Extra income from your side hustle is going to turbocharge your progress toward your financial goals, and there’s not much that feels better than that.

Improved Personal Brand and Career Prospects. In the modern – and increasingly digital – economy, you need to establish your own personal brand. That means having a strongly defined identity within your field or industry. You can accomplish this with a super awesome LinkedIn profile, your own website and online portfolio, or a blog that you write and manage.

You can also do this by starting your own side hustle. As long as it doesn’t present some sort of legal conflict of interest with your full-time job, consider taking your existing skills and knowledge to the freelancing or consulting world and operate on your own on the side. You’ll develop more connections, contacts, and yes, clients, all on your own. This will be incredibly valuable should you ever be laid off at your job – or if you ever want to leap into full-time self-employment.

Speaking of, turning your side gig into your full-time work is another great reason to start up your own hustle. Even if you’re not sure you want to transition from employee to entrepreneur right this minute, it’s always nice to have the option to do so. Alternatively, you could always start outsourcing your side work to other hustlers and freelancers if you develop it into a full-time business but aren’t ready to leave your full-time job.

Your career prospects are also likely to benefit as you further develop your knowledge and skillset. Even if you start with a side hustle you think you know everything about, running what essentially amounts to your own mini-business is going to provide you with a whole new experience and perspective. You’re very likely to pick up some new abilities along the way, too.

More Personal Happiness. If you’re already working full-time, it can sound a little counter-intuitive to say that adding on more tasks and responsibilities could actually make you happier. But it’s true!

When you willingly tackle your own work, your own projects, and  your own passions, even the hardest of that hustle is infinitely more rewarding and satisfying that working to make someone else rich. When you side hustle, the harder you work, the more you’ll (usually) be compensated.

You get to see an immediate return on your investment of time and energy – whereas when you’re an employee, you can bust your tail for months and the numbers on your paycheck will never change.

Plus, the freedom to make your own way, even if it’s just on the side or part-time, is fantastic. You’re the boss. You make the decisions. What you say goes, you have no one to answer to, and you can do things the way you believe they should be done.

Taking the Very First Steps

Convinced you need a side hustle? Here are some quick tips for making your first serious baby step of progress, and choosing what you’ll do on the side:

  1. Brainstorm a list of things you enjoy doing and things you’re good at. Doesn’t matter what it is – just write everything you can think of down on your list. If you can’t come up with anything you feel you’re good at, remember: you don’t have to be the world’s leading expert. You just need to know a little bit more than someone else in order to offer a service or product someone will pay for. Still having trouble? Start by thinking of what people have told you you’re good at!
  2. Narrow your list down to a handful of things people would be willing to exchange money for (whether it be a product or a service that you provide). Down to two or three things and can’t decide? This is your side hustle, so I advise choosing what you are most passionate about. Then run with it.
  3. If you have lots of things left, be honest with yourself. What are you best at? What do you do better than anyone else you know? That’s probably the side hustle you need to try first.
  4. Once you have your idea, the hardest work is done (it’s true!). Now it’s time to make a plan, spread the word, and prepare for business. Which we’ll save for…

…next time, when we’ll get more in-depth on what to do when you’re brand-new to side hustling in order to get the ball rolling – and how to keep the momentum going once you’ve got your first paying customer or client.

Have questions about starting your own side hustle, or how to turn a gig into a full-time business? Ask away in the comments!

See other posts in this series:

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DC @ Young Adult Money

Great post Kali! I definitely think that it makes sense to do something you enjoy. Side hustles can cause burnout relatively easy, so doing something you enjoy should be the first priority. Of course the second thing you mention – do something people will pay you to do – is obviously important as well. If you’re willing to work hard and sacrifice a side hustle is a realistic way to boost your income.

    Kali Hawlk

    Thanks, DC! You pretty much hit on exactly what determines side hustle success – and therefore the ability to earn more: a willingness to work hard! It does take time and effort, but the rewards are so worth your while.

Connie @ Savvy With Saving

Love this! Looking forward to this series! I started freelance writing as a side hustle last year and really enjoy doing it. My biggest challenge is finding new clients. Some months are so great I think about doing it full time and other months are so slow that I question whether or not I should side hustle at all. How do you get your name out there?

    Kali Hawlk

    Thanks Connie! Having that variable amount of work and the up-and-down income is definitely a challenge with side hustling – and it can be really frustrating on those months where your earnings take a dive. This is definitely something I want to address in a future post, and if you don’t mind, I’d love to feature your comment/question! It was a great one that I think deserves attention in its own post because it’s something that everyone struggles with.

      Connie @ Savvy With Saving

      Don’t mind at all! Looking forward to the post! :)


I’m so excited you started this series! I can’t wait for more =). This was a great introductory post to side hustling. My questions would be – how do you gain experience when you’re just starting out? Should you offer services for free to build up your resume? What’s the most effective way to network with others? Love the cat picture as usual! So cute.

    Kali Hawlk

    Thanks girl! Ooh, that’s a great question and I’d love to discuss more on this topic and have it featured in a future post. It’s tough getting started so I’d be thrilled to share some insights and hopefully help folks figure out the “how” of that part of the process!


Once again, you’ve managed to rally my motivation at just the right time. Such an awesome, comprehensive post – can’t wait to read more! You go girl.

In the meantime, you’ve also inspired me to get some hustle on:

    Kali Hawlk

    Aw, thanks Claire! 😀 ..and I’ll totally be humming that the rest of the day, too..


Would something like flipping stuff on ebay be considered a ‘side hustle’?

Ive started to dabble in that business, and I’ve learned that I suck quite badly at it.

Hoping you can shed some light on that topic for me!

Long Term Brian

    Kali Hawlk

    Definitely! Check out Budgets Are Sexy – J Money often has features where he profiles how different folks are side hustling, and he just had one about a guy who flips stuff on eBay. This is a great point that I’d love to tackle and talk about in the future, too!

Michelle @fitisthenewpoor

LOVE this comprehensive post! I am passing it on to my sister who is looking to start side hustling this month.

I’ve learned that you have to know your worth and talents. Never take a job that is way above your skill sets. Take what you can do and build your skills on the side.

    Kali Hawlk

    Thanks, Michelle! I hope it offers a bit of inspiration and motivation to your sister as she gets started :)

Broke Millennial

I agree that the side hustle helps develop some happiness. It’s often such a different creative outlet from a day job! I’ve started to weed out some side gigs as I start a new job, but it’s a great position to be in.

Looking forward to this series.

    Kali Hawlk

    Thanks Erin! I totally agree, if you’re at the point where you have to start pruning your gigs, you’re in a great spot. Congratulations for working your way into that position!

KK @ Student Debt Survivor

Great tips here. Sometimes the things you’re best at are not always the things you enjoy (I know this all too well 😉 ) Lately I’ve been thinking more about finding my passions and doing more things (side hustle, hobbies, full-time work) that I enjoy.

    Kali Hawlk

    That’s awesome, KK! Finding your passion isn’t always easy. I know I feel like I’m “passionate” about only a handful of things, are most of them aren’t going to make me money no matter how much I wish they would. Like hanging out with my cats, playing along with Jeopardy, drinking on a beach somewhere, reading all day long, etc, etc, 😉

Stefanie @ The Broke and Beautiful Life

Good point about just diving in. Since I started blogging and freelance writing SO many people come up to me with their ideas for their own side hustles and every time I see them it’s the same story- they have an idea but they haven’t done anything about it.

    Kali Hawlk

    Taking action is definitely REALLY hard. Once you get moving, it seems like things become exponentially easier!


Side hustling (though I really hate the term, it sounds sleezy haha) has changed my life more than anything else you’ve listed already it gives me a huge sense of pride and accomplishment. On my own I’ve been able to make huge strides in my debt repayment and help offset some of our family expenses, for this I’m proud and I genuinely enjoy it :)

    Kali Hawlk

    That’s wonderful that you’ve had such a great experience with working some side gigs, Catherine! Your comment made me laugh – my husband just said the other day how weird of a term he thought “side hustle” was!

Lisa E. @ Lisa vs. the Loans

Great guide! I think everyone, even if they feel safe at their full time job, should have a side hustle. Mainly so they can work on things they enjoy!


I’m absolutely loving not only your website, but your insights! I, too, am a freelance writer working toward making the side hustle the full-time gig, all while balancing a desk job. (So it’s nice to know I’m not the only one!) I mentioned your site in my most recent blog post here about cultivating different spending habits. I hope that’s okay with you. Thanks for the excellent posts and I look forward to reading more! :-)

    Kali Hawlk

    Thank you for the wonderful and kind words, Meghan! You’re DEFINITELY not the only one on this journey. Thanks for linking to the post — I’m headed that way now to check it out!


I recently got my first (and second!) side hustle jobs and I am SO CONFUSED about how to manage and track this new income stream, and I can’t seem to find any information about it. I’m having an extra hard time because I was laid off and I’m also collecting EI at the moment.

What documentation do I need for my income taxes? Do I even have to claim this income because there’s no official contract (both gigs are with other bloggers, not companies)? Should I be tracking my hours as well as income? What is considered a business expense? How do I cut down on paying PayPal fees? I could go on and on!

I find it very weird that I’m having such a hard time finding a “guide to setting up your side hustle” from the administrative/paperwork side of things. Or maybe I’m just over-thinking it?

    Kali Hawlk

    Amanda, these are AWESOME questions. I would love to address these issues in a future blog post — I think this could be an entire standalone post on its own, if that would be okay with you!


I’d like to suggest considering side-hustling in the non-profit world, as well as the for-profit world. I’m really interested in starting up a side-hustle that involves programs that directly benefit, along with products whose proceeds go to, women in developing countries. I know of successful models of nonprofits who have done this, but a lot of your side hustling advice is directed to people looking to make money off of clients and a market. I’d like to be able to pay myself a salary for my advocacy efforts at some point but understand that that isn’t going to happen any time even remotely near the beginnings of the project, and that’s why it has to be a side hustle (need to continue paying my bills with my 9 to 5 job). If you could keep us nonprofit side hustlers in mind in future posts, I’d very much appreciate it!

    Kali Hawlk

    Thanks for your comment, Kimberly. I’d love to learn more about side hustles in the non-profit world. That’s not my focus simply because it’s not my expertise — and I don’t like to provide tips, advice, and information on areas that I completely lack personal experience in. (Not because they don’t deserve coverage, but because I feel it would be insincere and disrespectful to my readers to act as an authority when I’m not.)

    That being said, I think much of my advice in this side hustle series can be translated over to a side hustle that is more of a passion project rather than a venture aimed to help you earn more money. Again, I’d love to learn more so don’t hesitate to email me to chat in further depth on this!

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