Side Hustle Part 1 Photo

Starting a Side Hustle Part 1: Setting Yourself Up for Success

This is part 1 of a 3-part series all about starting a side-hustle.

I’ve been running this business for over 5 years at the time of this post, and I’ll just be completely candid with you… I make WAY more money as an artist, doing this, than I ever did when I had a full-time “professional” career. I’m also way happier and have a much more flexible life than I ever did before.

Which is the dream, right?

HOWEVER… I think it’s really, really, really important to note that when you hear people talk about that kind of thing like I just did, you need to know…

It did not happen overnight.

I ran this business as a “side-hustle” on top of my full-time job for over a year and a half before ever taking it full time. And that’s not something to take lightly. Running a successful “side-hustle” was the hardest thing I ever did in my business… and maybe even in my entire life. It is HARD, and you gotta be ready to put in some serious commitment if you wanna make it work. But if you’re reading this, I’m assuming you’re a person who IS ready for that, and that’s what this series is about.

In this first post right now, I’m gonna walk you through step #1 in starting your side hustle… setting yourself up for success.

Rather watch than read? No problem! You can watch and listen in real-time by clicking the video below!

Let’s Get Started!

Alright. First let me tell you right away that this is the step I think a lot of people skip, because it’s not shiny and exciting. But this step is SO IMPORTANT if you want to, again, set yourself up for success.

And that is the actual brainstorming and planning step.

You need to know the answers to these questions before you can actually start taking action (which is what the second post in this series will be about, don’t worry). So I recommend grabbing a piece of paper and writing down these questions I’m going to walk you through, and then when the post ends, answer them for yourself.

But for now, let’s overview them all.


This will feel silly, but truly… make a list of things you’re good at. Now obviously this post is aimed at artists like me… so start with a list of things you’re good at art-wise.

Are you good at calligraphy? Are you good at drawing? Lettering? Doodling? Watercolour? Portraits? Renderings?

Make a list of all the things you’re good at… NOT things that you *think* would make a good business model or that social media is trending on.

Once you’ve done that list of art-related things, continue with things that aren’t just art -elated. What else are YOU specifically good at? You can get as obscure here as you want. Could be hobbies like makeup? Cooking? Playing the piano? Gardening? Pottery? Could also be skills like public speaking, writing, motivational speaking, poetry, and things like that.

Literally list out EVERYTHING in life that you’re good at.


So you probably already have an idea of what you want your side hustle to be, if you’re reading this post. But now I want you to GENUINELY think about it, without the rose-coloured glasses of starting a fun project.

Is there ACTUALLY a market for it? So many people skip this step. 

Let’s say you’re really good at lettering, and you thought to yourself… I could put my lettering on mugs! That’d be an awesome side hustle… people love pretty words on mugs. So you decide, ok… I’m gonna letter some words like “live”, “laugh”, “love”, and put them on mugs. Boom. Obviously those will sell like hot cakes.

But will they? Is there REALLY a market for more generic mugs that say live laugh love? Or is that just something you’ve seen on Etsy and thought was cute so figured you could do it too?

How about instead, you think about how you could do more than just generic mugs by actually pairing more than one of the things you’re good at together?

Maybe in Question #1, you listed that you’re good at lettering, and you’re also good at poetry. What if you paired those together, and lettered some of your own custom poetry onto mugs instead? What if they were one of a kind instead of generic? What if you wrote custom poems for people, and put them onto mugs for them to read every day? Wouldn’t that strike a customer as more meaningful than a live laugh love mug? Wouldn’t it make you stand out as THE go-to source for that item instead of one in a million on Etsy?

Or what if you went even one step further, and added in a third thing you were good at… pottery. What if you did custom poems, hand lettered on a handmade pottery mug?! (Side note here, that’d have to be a veeeeeery expensive item… but we’ll get into pricing in the third post of this series!)

Anyway– I think you see my point. Just have a real think about what the market is for your idea, and think deeper than just “well I’ve seen it done before, so I could do it too”. That doesn’t necessarily mean anything… it could be that that other person is making negative money on it!

Which brings me to question #3…


Now… this point could get pretty technical in terms of crunching numbers and knowing your expenses and all that jazz. And we’ll talk about pricing in the third post of this series so stay tuned for that.

But for now, in a general sense… you need to actually take a quick look at what you’re thinking, and determine if it can actually be profitable. Too many people get caught up in the fun project idea and don’t actually consider if it would be profitable or not. So run some basic numbers on what you think the expenses will be for creating what you want to create, and what you might want to sell it for.

If you run those numbers and realize that your expenses are actually higher than what you’d make from it, then what you have is an expensive hobby. You may really enjoy doing it, and people buy from you, but it’s not a business if you’re not making any money from it. Even less so if you’re SPENDING money to run it!

If you run those numbers and see that you can make a profit, even if it’s a small one, then that’s a good sign. Remember: as a side hustle, you don’t need it to be making a TON from it. It doesn’t have to be a full-time income from it… right away anyway. Just make sure it’s in the positive, and then you’ll be able to scale and change to make that profit higher over time.


Okay some real-talk. If you want to turn this thing of yours into a side-hustle, you are going to LIVE and BREATHE this thing. Of course boundaries are good and great and you should have boundaries around your energy and taking care of yourself and all that jazz (that’s a topic for another day). But realistically, you are going to be thinking and dreaming and wondering and writing and talking about this thing con-stant-ly.

Do you love it enough to do that? Or is there a part of you that thinks… ‘hmmmmm… I may get genuinely sick of this pretty fast’ – try and determine that before you spend a bunch of time and money and effort getting yourself set up logistically. It’s totally OK to fall out of love with something. Your side hustle doesn’t have to be FOREVER (it’s not a commitment forever!), but you want to make sure it’s at least worth the time to get it STARTED! It’s not going to be free, and it’s not going to be easy.

And if you look at it and think, ‘ohmygosh ya I love this so much! I could do this and only this forever and ever, all day every day…” then move on to the final question…. Question #5.


Honestly, this is just a bit of real-talk for you. This is something I did not realize before I started my business, and I wish someone had said to me. I’ve since discussed and agreed on with soooo many other artist business-owners.

And that is… you need to understand that when you take something you’re passionate about, especially if it’s something you started as a hobby for yourself (like calligraphy & lettering was absolutely a huge hobby of mine that I completely fell in love with) and turn it into a business… it will steal that hobby from you.

Maybe not right away, but over time, you will stop wanting to do that thing for yourself. At the start that wasn’t true for me– I would do it as a side hustle and still loved it as a hobby. I would do lettering for client jobs and then still unwind at the end of the day by doing some calligraphy  in my notebooks just for fun. 

But I can say with certainty that now, calligraphy and lettering are no longer a fun hobby for me. I do not do them to unwind. 

I live and breathe calligraphy and lettering for my business, and it no longer brings me that personal joy and relaxation that it did when it wasn’t monetized or a business. Now if I ever get a little spark to sit down and do it for fun (which is suuuuuuuper super rare– like once every 6 months kind of rare), I INSTANTLY think about how I can make it productive. Can I make this thing into a print I can sell? Can I make this a viral social media post? Can I digitize this and use it for client work? That kind of thought just taaaakes over every time I do art now. No matter how hard I try. And maybe this isn’t the case for every artist out there, but I know I have other artist friends who feel the same way. 

Which means in the end, I’ve lost that hobby. And now I’m on the hunt for something unrelated to calligraphy or lettering to fill that “just for me” hoppy void.

And don’t get me wrong, I still absolutely LOVE doing calligraphy and lettering, and I’m so grateful that it’s my job. But it’s different. It’s not a relaxing, me-time kind of love anymore. 

So really ask yourself… are you prepared to lose that hobby? Are you ok with knowing that your relationship with that thing you once absolutely LOOOOOVED for yourself will change? It’s not that you won’t love it anymore – it’s just a different kind of love. Just think on it for a bit. I genuinely wish someone had asked me that from the start. Not that I wouldn’t have done it… I just wish I could have spent some time thinking about it and been able to expect it. 

And That’s A Wrap!

If you’re sitting there now having heard all of that and thinking “K I got it, I don’t need to actually think through these things. I think my idea passes all the tests…”, then I still stronggggly encourage you to ignore that thought and not skip all of this. Take these questions with you and write your answers down. It’ll make you really think about these things and think of things you hadn’t considered before. 

As a recap:


And once you go through and refine all of that, know that you are seriously ready to start putting your thoughts into actual actionable steps!

Stay tuned for the next post in the series where I’ll be talking all about the actual, action-taking logistics to start with. The part that is overwhelming and exciting all at the same time.

For now, before you leave, tell me in the comments: what is the idea you have? What do you want to do as a side hustle? I’m sooo curious! Tell me below!

And finally, your dad joke…

I’ve been building playsets for kids in my spare time…
It’s my slide hustle.


Tell me what you thought!