I Wish I Knew Cover

3 Things I Wish I’d Known BEFORE Starting My Business

If you’re thinking about starting a creative business, I want to screeeeeeam a few things at you and make sure you hear them before you start. I genuinely wish someone did that for me!

I get asked for business advice allllll the time. And I totally get it – running my own business was totally unknown at first. I didn’t know what I was getting myself into (the good and the bad), and I thought a lot of the businessy things were complicated (and even a little scary) when I was first getting started. I definitely don’t consider myself a business expert, but I have three things to share with you from my own experiences. If nothing else, I hope I can save you some time as you get started on your own.

Rather watch than read? No problem! Feel free to watch and listen as I explain the 3 things I wish I’d known before starting a business. ??

I’ve been running this business, doing and teaching modern calligraphy and other fun art stuff, for about 5 years now. When I started it, I had a full time job and absolutely ZERO experience with what it meant to run your own business. I’m pretty scrappy and figured it out as I went… but looking back, there are a few things I REALLY wish I’d been prepared for. I’ve got three things I want to share with you. If you take away nothing else, just read point #3. Seriously. It would have saved me a LOT of time and stress.

#1 – Turning your hobby into a business means you no longer have a hobby. 

This one actually didn’t hit me until about 2ish years in when I hit a massive burnout. I know, I know – you’re probably like “yaaaaa, that won’t happen to me.” JUST TRUST ME, and take this in, okay? 

You probably started learning calligraphy (or whatever hobby if you somehow found me and AREN’T into calligraphy) as a fun pastime. You enjoyed making cards or crafts or picked up a brush pen for fun in your spare time. And theeeeeen, somewhere along the line, you got OBSESSED with it, practiced OBSESSIVELY, and got good enough that someone asked you if you could make them something. And it CLICKED… you could totally do this for money and make a business out of it.

Literally word for word that’s what happened to me. At first, when I started doing it for money, it was really exciting and fun. But over time, there’s this slow creep of resentment. No longer is it something you do because you WANT to – it’s something you do because you HAVE to. And the very nature of that changes the feeling of love you originally had.

Your hobby is no longer a hobby. It’s a job.

It wasn’t until a few years in, when someone asked me what I do in my spare time, that it really hit me. I used to say I did calligraphy or crafts or scrapbooking in my spare time! But now that it was my job? I realized I didn’t sit down to do calligraphy for enjoyment after hours anymore. I had lost having a hobby altogether, and I really missed it.

And listen, this is not to say that I do not LOVE what I do. Because I do. I am so so so so lucky to be able to do something I love as my job. It’s really incredible. But the moral of the story here is to really just have a think on whether or not you are OKAY with losing that hobby you love so much in favour of a business. Because truly, it isn’t for everyone. I had a conversation with a friend the other day who had the same realization as me, and she decided to quit making money from calligraphy jobs altogether. She wanted to just love it for herself again! And that’s TOTALLY okay.

#2 – Creative businesses aren’t that creative.

Running a “creative business” is only ACTUALLY creative about 1/4 of the time. And honestly, that’s being really generous. I remember having these visions of how wonderful it’d be to just wake up every day, roll into my studio, make stuff, hand it off to clients, make money, and call it a day. And it’s not like I’m completely oblivious… I knew there’d be more to it than that. But I’ll be honest, I did NOT expect that the actual creating would be so much less than I imagined. 

When you’re running your own business, the “business” parts are most of what you do. Answering emails, communicating with clients, managing your website (omg, websites), researching, bookkeeping, ordering inventory, networking, managing social media (omg, managing social media) and so so so so so much more. 

There is so much, especially in the first few years, that are BRAND NEW skills you have to learn that take you 10 times longer too. The thing to think about here is that this is even MORE true if you’re doing it as a side hustle. You may have a full-time job and come home ready to do your client work, but you need to remember that you still need just as much time to do alllllll the other things too. This gives you even LESS time creating. So it’s really important to realize, before you decide whether or not to jump into it, that it won’t be all fun art playtime! Though when it is, it’s the best!!

#3 – The scary stuff isn’t that scary. 

This is super important. I finally learned that scary stuff was not actually that scary! And that I should have done it waaaaaay sooner. I’m specifically referring to two important things here:

1. Registering my business
2. Understanding personal/business finances and taxes

When I say “scary”, I mean… I hadn’t set anything up yet. I had barely even decided to start doing this as a business when someone asked me to make them invitations. I was TERRIFIED that the second I did anything “legitimate” for my business, like accept money from this client, I was somehow breaking the law and the tax man would come after me and take my house or something because I’d broken some “running-a-business” rules I hadn’t known about. And then that feeling like I’d do something wrong held me back from actually figuring out what I needed to do for a long time. 

Finally, after about a year of just accepting money and not actually being a “legitimate business,” I found a bookkeeper who was super nice and not judgmental. I told her all of my fears and asked her to help me figure out what I needed to do. 

When it came to registering my business, it literally just meant filling out a single form online and paying $30 to my province. (Note that this will be different everywhere, depending where you live, but everyone I know agrees that this is always very simple.)

When it came to accepting money and paying taxes, turns out this is pretty simple, too. I had the notion in my head that this was really complicated, when it turns out that it’s basically just a couple tax forms to make sure you claim the income properly at the end of the year.

What I did learn about accounting, though, is that I reeeeeally should have separated my business and my personal finances RIGHT OFF THE BAT. It was a real, real nightmare to go through a year or so of transactions in all my accounts and credit cards and figure out what was a client payment, what was a purchase of supplies, and all that jazz.

So my super duper practical advice to you is two-fold…

1. Look up “business registration (insert province or state here),” and DO IT.
2. Separate your accounts.

This can be as simple as making a second checking account in your current one, and signing up for a second credit card in your own name. Or you can open a business account. Once you have a separate account and card, make all your purchases for the business through there, and have all the payments you receive go into there.

THIS. WILL. SAVE. YOU. SO. MUCH. TIME. LATER. I. PROMISE! And it doesn’t need to be scary.

*Side note: If what I just said overwhelms the crap out of you, find a bookkeeper or accountant and pay them their hourly rate to sit down with you and help you make a plan. It was definitely worth it and definitely helped me with my peace of mind!

Okay, so there you have it – my 3 (well, sorta 4) things I wish I had known before starting my business:

  1. Make sure you’re ok with losing your “hobby”
  2. Understand that you won’t be doing all creative work
  3. Register your business AND separate your bank accounts!

I hope this was helpful – whether you’re just getting started or have been doing this for a while, hopefully I can save you some time or make you feel a little less alone. 

And that’s a wrap!

If you’re looking for some more business-y topics, check these out!

Some small-business dad joke humor for you:

Why did the doughnut maker retire?
He was fed up with the hole business.


  1. YES!!!!!
    Hobby to a job. Every single time . Even as a side hustle, you expect something else from it more than a hobby. It has to be more SERIOUS! I learned this when I turned making silver jewellery into a side hustle and then glass fusing – every design had to be commercially viable and it saps the joy of designing! I’ve made myself stop saying to people “that’s amazing – you should sell those!” Because that’s not always the best thing.
    Separating out the business accounts : Yes!! I only did that this year. Didn’t realise you could get FREE business accounts. Now linked to my PayPal and Amazon accounts. Game changing!
    This is a wonderful post!! Wish I’d read it three years ago. Thank you!

  2. I learned to fly in High School (working two jobs to pay for it). One job was at the Airport, the owner of the business at the airport told me when I said I wanted to fly for a career, “don’t make your hobby your business, you won’t have a hobby.” I’d also read a novel that described being a pilot, in many jobs, was like being a glorified bus driver. So, I never pursued flying as a career. I wish you’d had a mentor guide your way with a statement about ‘finding a new hobby.’ Not that you have time as a small business owner for a hobby. Thanks for mentoring people!!

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