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The 5 Biggest Mistakes I Made In My First Year Of Business

Entrepreneurship is a roller coaster ride, no many how big or small your business. There will be good days and there will be bad ones. While I've done a lot of things right in my first year of business, I've also made my fair share of mistakes.

Today, I'm sharing some of them with you in the hopes that you could learn from them.

Mistake #1: I was too afraid to raise my prices

When I had just started Tiny Dog Paintings in early 2020, I charged a very low rate for every dog I illustrated but it was intentional. At that point, all I wanted to do was to get my work out there in front of the right people (dog parents) while giving myself the opportunity to practice and get better at my craft. And my strategy worked. I was getting enquiries daily and kickstarted my business.

However, soon I realised that I wouldn't be able to keep up at this pace. I knew that I needed to charge more but at the same time I was so afraid that if I did, I would somehow alienate all my customers. So you know what I did? I "compromised" with myself and raised my price... by $5. Yup, $5. Which obviously didn't make a huge difference and I found myself back in the same situation soon after. So I raised my price again... by another $5.

"This was no longer a strategy, this was my fear manifesting."

I am not kidding when I tell you that I made these $5 increments a total of 4 times over a few months and even then, my rates were still below what other pet illustrators were charging for their work. This was no longer a strategy, this was my fear manifesting. I knew that people loved my work yet I still struggled to bring myself to believe that I could demand a higher price. I had to get my mindset away from that limiting belief because if I couldn't see the value of my art, how could I expect my customers to?

It took some inner work and some "oh heck let's just try it" attitude but the next time I increased my prices, I raised it by 50% and I'm happy to report that my customers stuck by me.

Mistake #2: No cohesive branding

Looking at my content across my website, Instagram and emails for Tiny Dog Paintings right now and you will see a pretty solid branding. I have a fixed colour palette, standard fonts and photography style for my work. It's recognisable which is what good branding is meant to do. However, my branding was all over the place in my first year of business.

Aside from my dog illustrations, there wasn't anything that made my business memorable or recognisable. It wasn't until I sat myself down to create a simple brand guideline for my business that my brand began to look more cohesive. If you're looking to do the same, this is what you need:

  • Colour palette: 2-3 primary colours and another 2-3 secondary colours

  • Fonts: 2 fonts in differing styles (test them together and make sure they pair well)

  • Logo: In your chosen colour scheme and font

Of course, branding can go much deeper but these 3 elements are a great starting point and are enough to make a huge difference to your aesthetics.

If you need a little help, head to Pinterest and search "Branding Templates" and you'll find a ton of inspiration. Possibly even some free downloadable templates!

pinterest branding template screenshot
Search 'Branding Templates' on Pinterest for inspiration

Mistake #3: No clear boundaries

For the first year in my business, I made most of my sales through Instagram DMs. It was definitely convenient being able to speak directly to my customers on the platform. However, because I had set no boundaries for myself, I felt the need and pressure to respond to every DM the moment I received it.

Similar to my issue with raising my prices, I was acting from a place of fear, thinking that I would lose that potential customer if I didn't respond to them immediately. To make matters worse, my target customers are based in the West and in the complete opposite time zone that I am in here in Malaysia. That meant that I was often answering DMs late at night because that is when they would be awake and active. Before going to bed, I worried about the DMs that would come through during the night that I wouldn't be able to respond to until hours later when I woke up.

A big reason for this fear and the consequent lack of boundaries on my part was due to #4.

Mistake #4: No systems

I didn't have a clear system surrounding my communication with customers and because of that, I felt like I always had to show up on the spot. Not only that, I was constantly getting the same questions and typing out the same answer again and again. Not the most efficient use of my time, that's for sure.

Now, I have a few systems in place that have helped me tremendously when it comes to setting boundaries and improving my productivity overall.

  • Shifted from accepting commissions from 'all day, every day' to 'one week per month'. At the start of every month, I open up commission slots and that is when my customers make their orders. After that week is up, I can focus entirely on fulfilling them. Just having the space to be in that state of focus is amazing. I make sure to communicate this well and in advance via my website, Instagram and emails so these days, I receive far less commissions-related DMs because my customers know the drill. If you don't work on a commission basis but instead sell non-custom work, then your system could look like timed collection launches. So rather than creating and launching a new product every few days or weeks, you focus on creating larger collections at one go that you then release in batches. This gives you breathing space so you don't feel like you're constantly playing catch up with your launches.

  • I started an email list! This has made communicating with my customers so much more seamless. I update them about commission opening dates, send them reminders and all I have to do is write 1 email that can be sent to everyone on my list. No more having to repeat myself over and over.

  • I created template responses for the occasional DMs that I do receive. It's a fixed message where I inform them of the upcoming commission slot opening and invite them to join my mailing list so they don't miss out when I reopen. And again, this works too even if you're not in the business of commission work like me. Make a list of your customers' FAQs and create template responses for it. Whenever you receive a DM or email with one of those questions, you can simply copy and paste from your template. Better yet, create a page on your website or a Highlight Reel on your Instagram Stories so they easily get the answers to their questions on their own.

Mistake #5: I didn't start my email list sooner

I'm a little ashamed to say this but I only started making efforts to build an email list after more than a year of running my business. I'm not even sure why I waited that long!

"Think of your email list as a direct hotline to your potential customers."

An email is so important so if you're reading this and are yet to build one for your business, I urge you to make that your top priority! Why is it so important, you ask? Think of your email list as a direct hotline to your potential customers. Your content has a way better chance of being seen if it's in their inbox versus on their Instagram feed. You can market to them over and over as long as you treat that relationship and trust as sacred.

Not only that, it's a great way to get repeat purchases from your existing customers. Repeat customers don't just spend more than new ones, they're also much easier to sell to because they already know, like and trust you!

Today, I pay close attention to growing my gang (that's what I call my email list members) and serving them by offering exclusive bonuses or freebies that they cannot find anywhere else.


Well, I hope you found this helpful! There are 5 mistakes in this list but trust me these were not the only ones I made.

If I were to write them all down you would be reading a book, not a blog post. I hope that this serves as an encouragement to you that everyone starts somewhere and makes mistakes along the way. I make new mistakes all the time and guess what, I'm okay with that. Every mistake is an opportunity to learn something and that's always a good thing, right?


Hi Ming, these tips are gold! Glad to stumble across your lovely website and thank you for your candid sharing.

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