My Biggest Regret As a Small Business Owner

"I wish I had started sooner. — That's it. That's the whole regret."

People ask me all the time what I would do differently if I could go back and start Canvas Monsters over. I don’t know what they expect me to say, but my honest answer is pretty damn simple.

My biggest regret is that I didn't start sooner.

The Overthinking Trap

Before Canvas Monsters was a functional business, it lived in my head for a long time. I started the idea in 2017 simply by drawing daily art prompts and posting them on Instagram. But I knew I wanted to do more. I sketched out tons of ideas, made all kinds of lists, researched platforms, pricing strategies, branding, packaging, etc. I was convinced I needed to have everything figured out before I could take a single real step.

But the truth is no amount of planning fully prepares you for actually doing it. Running a business is a completely different experience than thinking about running one. And the longer you sit in the planning phase, the longer you delay the real education that only comes from being in it.

The planning phase feels productive and sure there are some things you should have figured out, like your business name, getting a business license, and opening a business banking account. But there's a point where it becomes a comfortable excuse to not begin. If you're reading this and you've been "almost ready" for a while, quit waiting and just do it!

It's a Marathon, Not a Sprint

Building something of my own is one of the most rewarding things I have ever done, but it’s also one of the most demanding. I quit a 9 to 5 salaried job to dive into this business full time and it turns out I now work more than I ever did. But I love it and it’s my own. Running a business takes patience, persistence, and a whole lot of learning as you go.

Every month you wait is a month of experience you're not gaining. Every order you don't fulfill is a lesson you don't learn. Every customer you don't interact with is feedback you're missing. Time is irreplaceable, and you simply can't shortcut it.

Also, you can plan all you want but things will go sideways anyway. Get started and adjust as you go. That's the whole game. You have to be willing to adjust as needed. For example, in my first year I thought it would be fun to have a rotation of stickers and change them out every month. Well, that got overwhelming very quickly. Too many designs to keep up with! Then I decided to change them out seasonally, so only 4 times a year. That was more manageable, but even so I adjusted again. Currently, I have a core set of characters that are popular with everyone and I make different variations of them during different times of the year. I do have some designs that are exclusive to a season or a holiday, but I’m not swapping out everything like I did at first.

Start Now, Even Small

You don't need to quit your job tomorrow. You don't even need a business license on day one. You don't need a perfect logo or a full product line or a polished website before you sell your first piece. All those things can be adjusted along the way.

Start as a side hustle. Sell three things and see what happens. The exhilaration I felt from my first real sale was worth more than six more months of brainstorming. First of all, I was genuinely shocked that anyone would want to buy my art. But I was equally elated – maybe this business thing is going to work out after all!

Based on my experience so far, here’s what I recommend:

1. Pick one product or idea to focus on. Don't build an empire on day one. Pick the one thing you're most excited about and start there.

2. Put it in front of potential customers by posting it, sharing it with friends, and telling people about it. You need real feedback from people who aren’t you.

3. Sell it. Actually exchanging money for your thing will change how you see yourself and your business.

4. Adjust and keep going. Something will inevitably go wrong. Try not to see it as a failure, but as a learning opportunity. Learn it and move forward.

You Don't Have to Figure It All Out

You are not going to know how to do everything. That is definitely the challenge with running your own business. As a small business owner, you have to do everything from making the thing to filing taxes. But no one knows how to do everything; and if they say they do, they’re lying.

But here’s the thing: you will figure it out, hire help, or find someone willing to help. Someone said something once that has always stuck with me: “Do what you do best, and hire out the rest.” I still have a hard time following that rule myself, but it is helpful.

The internet is a wild resource. YouTube tutorials, forums, communities of makers and artists and small business owners… help is out there. If the problem is big enough, you'll find someone who can help. I highly recommend hiring an accountant to handle your taxes. If you need to build a website but have no idea how to do it, it’s likely that you have a friend who took those MySpace years seriously and knows web design. If you ask, they might just be willing to help. Finally, join a community (online, local, or even both!) of other makers who've been exactly where you are and they will be filled with resources.

Follow Your Passion

Canvas Monsters exists because I eventually stopped waiting. Not because I felt completely ready, or had everything perfectly planned, because I definitely didn't. It exists because I finally decided that the cost of not trying was higher than the cost of waiting to feel ready.

If you're an artist or a crafter who wants to sell your work — start! If you've got a business idea that won't leave you alone, listen to it. Start right now.

And then come back and tell me about it. I love learning about what you guys do!