The 3 Hardest Lessons I've Learned as a Business Owner

jenna rainey

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I’m an artist, self-taught designer, and multi-faceted creative entrepreneur who is hell-bent on teaching everyone how to find their inner creative voice.

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The 3 Hardest Lessons I’ve Learned as a Business Owner



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The 3 hardest lessons I’ve learned as business owner aren’t easy to talk about.

After years of being a creative entrepreneur, I would say that I’ve learned many client and customer lessons the hard and painful way.

If you want to have success with your clients, whether you’re creating illustrations for someone’s home, or designing logos, etc., you will need to learn these lessons at some point in your journey, so let me save you some time, heartache, and money!

Here are the 3 hardest lessons I had to learn:

#1: Always get the client’s approval

This first hard lesson I learned happened early on in my career as a creative entrepreneur when I was a custom wedding stationery designer. 

For my VERY FIRST stationery design job, I was hired by a couple to design their save the dates and address their envelopes. The bride asked for a gold ink on a sage green envelope for the addresses, and without thinking about it, I addressed them all without sending a photo proof! At the time it didn’t seem like a big deal, but after sending out all of her save the dates to the guests, they were all returned to her from the post office. The ink color was too light and hard to read! They ended up firing me after that and that was my very first job.

Related: 3 Tips for Growing a Stationery Business


#2: Trust your gut

About two years into my creative career, I said yes to a job that I just knew from the beginning was going to be a nightmare. She was asking for things that I didn’t have experience with yet. We ended up getting into a disagreement over paper colors and I decided to end our contract together. It was mainly over a small miscommunication, but the stress it was causing and the time this relationship ended up taking was something I could no longer afford. I had other clients to tend to, and nothing I could do would please this particular client. You can’t please everyone. Ending this contract resulted in me having to eat some of the cost (a couple thousand dollars)! I was early on in my business, so I couldn’t really afford to lose a job, let alone lose money from a job, so that lesson REALLY stung!


#3: Pay attention to income and expenses

This last mistake (I’ve made countless more than just these 3), is super common among creatives. For a few years, I avoided looking at my profit and loss report sheets and my books, because I was too afraid of what I might find out. Your profit and loss reports help you measure how your business is doing! What’s working, what isn’t…what expenses you can cut out, etc. This will help you keep a pulse on if your business is growing each quarter, and where to focus your time and attention!

Related: The Worst Piece of Advice I’ve Ever Received


Just like anything hard, having setbacks and hiccups in business can be gut wrenching. I’ve spent so many sleepless nights worrying about mistakes I’ve made, or how can I make it up to this or that client, but here’s the thing:

We all make mistakes! And I love this quote from the great Miles Davis:

“It’s not the note you play that’s the wrong note – it’s the note you play afterwards that makes it right or wrong.”

How you respond after making the mistakes, whether you rebound and learn or not, is the determining factor of whether you grow. Embrace the mistakes and always be sure to extract the lesson from them! They hurt and can be embarrassing or overwhelming, but there’s always something there that will make you better!

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