Hey readers, I thought it'd be fun and insightful to share some of the biggest mistakes I've made over my four years of self-employment. If you enjoy this content, I'd love to hear it. Feel free to message me on Instagram or at hello@annlettering.com. 

I once naively agreed to a five-figure project with payment due 45 days after invoice submission (Net-45) without a deposit, per the client's terms. I require at least a 50% deposit upfront for most commissions, especially murals. But, having heard that several respected artists I admire joined this project, I felt good about being offered this opportunity. So, what could go wrong? 

I got paid THREE months after I completed the gig. Ouch! Once I realized the client couldn't deliver on their promises, I was tormented by the idea of never getting paid and possibly hiring a lawyer. 

As I mentioned, I got compensated eventually, including a late fee I added to the contract, but this was a hard lesson to swallow. A 50% deposit would've helped me establish better trust with the client and made the payment delay feel less overwhelming and risky. I spent countless hours pursuing the client on the status of my invoice and losing sleep and precious peace of mind over this ordeal. I'm thankful I had a signed contract to defend me if I had to lawyer up. When a client refuses to sign a contract, that's a more significant red flag than payment terms without a deposit. However, having experienced the emotional turmoil I've gone through, I recommend never working on a flat-fee project without a 30%~50% deposit with clients. 

Since society has ingrained in women that we must always be pleasant and patient, there were moments when I even felt bad about asking for MY money, which is downright absurd! If you ever face a situation where client payment is long overdue, please don't feel guilty about chasing the client relentlessly for what they owe you. 

I designed an exterior mural and hired a sign company to install the design as printed vinyl. I recommend vinyl when clients have limited budgets because vinyl is affordable and faster to install than hand-painted murals. Unfortunately, everything did not go as planned for this mural. But first, let's cover why I went down the rabbit hole of subcontracting.  

My first experience with vinyl was wrapping utility boxes for a public art project. The contract required the artist to hire a sign vendor to install the vinyl on utility boxes. It's common for public art projects to involve subcontractors, such as outsourcing a professional to power wash or prime a wall. Since the utility box project was successful, I was confident about subcontracting a sign company for this exterior mural. As someone who prefers to be in control at all times, I foolishly believed this project's success depended on me to manage the installation. How can I trust the client to handle this? Yep, ego much?  

From my research on vinyl, I understood it's an excellent option for murals, especially indoors and away from direct sunlight. It can last 5-10 years outdoors, with specific colors fading first. My vendor informed me the material we used is exceptionally durable. But vinyl is fickle and requires multiple factors to align perfectly. Unfortunately, the universe was not on our side for this one. We encountered numerous problems due to weather, location, and inadequate wall prep.

With the vendor as my subcontractor, I'm liable for fixing everything for my client. It was a massive nightmare! This awful experience made me realize the risks of being responsible for subcontractors and their work quality. Also, sometimes things can still go wrong no matter how prepared or experienced people are. 

Since this incident, I now inform clients that they are responsible for hiring a vinyl vendor separately from me. My proposals and contracts clearly state that I only deliver a digital design file for print. At most, I offer some coordination about color proofing and print file production with the vendor for an added fee. Still, the sign company is contracted directly with the client. If anything goes wrong, the client will contact the vendor, and I can move on from the project without worrying about the vinyl.   

As someone who has purchased and benefited from several online courses by other creatives, I quickly shaped a misconception that there was only ONE proper format to teach online and have a successful educational product, and that is video content. Cue the footage of me introducing the course, cheerful music playing in the background, and audio clips of me expanding on bullet points of tips and wisdom. 

And so, I plunged into numerous holes of starting a course and giving up months later after being crushed by the weight of filming and editing. I'd confidently finish writing my course summary and outlines, then abandon ship because I dread being on camera and recording audio. Once I got hung up on the filming aspect, it was easy to surrender to other doubts too. Would anyone want to buy this? Will this be helpful to creatives?  

It was only a matter of time before I deserted my teaching aspirations. What finally changed my mindset was encountering other resource products like digital guides and printed booklets. I then realized that conventional ways of consuming knowledge through reading are still relevant and engaging. Even though video content is ubiquitous online, some of us still read articles and buy books! After I reached that conclusion, I finally rolled up my sleeves to produce my first educational product in written presentation pdf format. 

Writing has always been my best communication style; it's how I relay information to clients and why I have a newsletter instead of a Youtube channel. I like being able to refine my sentences and word choices. In retrospect, it made sense why my soul disintegrated whenever I attempted to make videos. It was like squeezing my feet into shoes that didn't fit me. Conforming to other people's course formats made my course-creation journey hard and miserable. 

So if you want to create educational products, tune into your strengths and communication styles. If writing is your forte, Digital guides could be the most efficient way to deliver your lessons. If you want videos but lack the time or technical skills, you can always outsource for help. There are many ways to teach; I recommend choosing what's comfortable for you rather than following what's trending or what works for other creatives. Just remember that people who want to learn from you will gladly ingest your knowledge in whatever form you wish to share. 

The following two mistakes are related to finance. I'm not a financial expert, and everything I share is my opinion based on my experience. This post does not contain any financial advice. Please consult a professional or research independently before making any financial decisions.  

In 2019, I left my 9 to 5 design job to start my mural business. To kick off my grand adventure into self-employment, I purchased an expensive freelance starter pack: a MacBook, a refurbished iPad, and Apple Pencil. I furnished my home office with a standing desk and IKEA shelves. I bought paintbrushes, liability insurance, a projector, supplies, and equipment for murals. By the end of the year, I racked up $30k in business expenses, all foolishly paid with a debit card for my business bank account. Facepalm! 

If I had spent that $30k with a business credit card, I could've built my business's credit score, earned purchase points, and qualified for bonus cashback offers. With that $30k, I missed out on $1,200 cashback. That's FREE money I left on the table! Even though $1,200 is not life-changing, it could've gone toward expenses like cell phone bills, software subscriptions, or a nice projector. 

Aside from the cashback perks, owning a business credit card helps keep my business expenses separate from personal spending. It's easier to track, especially during tax season when I have to categorize my business expenses. 

There's a misconception that you must be a formally registered business, such as an LLC, to qualify for a business credit card. In fact, anyone doing business for profit can open a business credit card, even if they only work on that business part-time or seasonal. Be sure only to spend what you have in the bank, and always pay your card off each month to avoid having interest fees sneak up on you. If you know you can't be trusted with a credit card, it's best to avoid them. 

I only have one business credit card, Chase Ink Business Unlimited, with zero annual fees and 1.5% cash back on all purchases. They offer a $750 bonus cash back for new cardholders if you spend $6k within the first three months. Here's my referral link to learn more! 

For the longest time, I wrongfully thought that only big corporate companies had access to 401ks. But actually, a one-person art biz like mine with any business structure type and zero employees other than yourself and a spouse can have a 401k known as solo-401k. 

Solo-401ks have a higher maximum contribution limit than other retirement accounts, with the option of reducing your taxable income. I only started mine two years ago and wished I had started investing earlier rather than having my money sitting idly in a bank, losing its purchasing power over time due to inflation.

With a solo-401k, I can contribute as an employee and an employer, allowing a combined contribution of $66k (2023 max limit) toward retirement. As an S-corp tax entity where I pay myself a salary, I can defer up to $22,500 of my salary as an "employee" contribution. On top of that, I can contribute 25% of my W2 salary as an "employer" as long as it doesn't surpass the combined limit of $66k. The "employer" contribution is also a business expense write-off. This is a big deal for those who want to reduce taxable income and save for their future selves! 

If you are earning money and new to retirement savings, start small with a goal of $500~$6,000 yearly in an Individual Retirement Account known as an IRA. If your biz income allows you to save more than $6k, consider a solo-401k in addition to the IRA. With both accounts, you must decide between Roth and Traditional contributions. Go here to learn about Roth vs. Traditional from this NerdWallet article.  

Aside from just opening retirement accounts, you'll need to know where to invest your money. Most of mine are invested in a Vanguard's target date retirement mutual funds based on my closest retirement year. I also contribute some to Vanguard Total Stock Market Index Fund (VTSAX).