5 Things I've Done Wrong: A How Not To Guide to Your Small Business

Let's just say that this took quite a bit of narrowing down because while I have only been doing this a bit over a year, it sure seems like I've made more than a year's worth of mistakes. Let's hope that you can learn from my example and not have to set a bad example of your own.


Whether it is running your own small business or trying to help others with theirs, this is a valuable lesson that I learned the hard way. Everyone wants to have input on how things are done, but rather than people feeling like they contributed, they often get their feelings hurt. Imagine a situation in which Person A believes that they need to say something about how Person B's area of expertise is run. Person A is probably going to be told by Person B to butt out, Person B is going to feel hurt that Person A felt the need to insert their opinion in the situation, etc. There are a million ways for it to go wrong. I've learned that over communication can be just as bad as under communication.

Whenever I begin a project with a client, I ask them to name the scope of communication for each portion: people involved in logo creation, people involved in website creation, people involved in feedback. By limiting it from the outset to those only essential for each portion, I've found that people are much more likely to understand and agree with their role in the process and ultimately, less likely to get their feelings hurt.


Pricing can be difficult, especially if you are just starting or you sell a dynamic, creative product/service. So I started on double hard-mode and I'll be honest; I still don't have it down to a fine science. Here are some general guidelines:

If you sell a service by the hour, price competitively with your competition. (Obviously.)

If you sell a product, here's a great formula that you can tweak.

It sounds great in theory, but putting it into practice can be difficult. When I was starting, I was terrified that people would think I was overcharging, so I priced very, very, veeeeery low. What did it do to my business? Here's a fun list:

1. I felt devalued even though I was the only one devaluing myself - preemptively I might add.

2. I wasn't making enough money to invest back into my business with software and training.

3. I was setting a precedent that I worked cheaply and was in danger of becoming a bargain, not an expert.

I can't tell you that there is a perfect solution. But I can tell you that pricing wasn't my worst enemy; I was.

3. NOT 1099-ing

If this sounds like an exotic new sex move, get your mind out of the gutter. That couldn't be further from the truth. We're talking tax forms for freelancers. If you make $400 or more a year from your business (let's hope so!) and you won't be filing taxes under your business, you need to report income on your taxes in a special way. That's where a 1099 -MISC Form comes in. Do yourself a favor and require it on completion of every project that pays over $600. Come tax time, the IRS is going to want one for every income payment that you report and getting them throughout the year while it's still on your client's mind is far preferable compared to calling everyone at an already busy time of the year.

Also, if your income is entirely from freelance work, you need to look into the 1040-ES Form for estimated tax payments during the year. Isn't that fun? Ugh.


When you are starting out, a lot of your work will probably be for family, friends, or on a volunteer basis. You may think that situations like this are ones in which you don't really need to have a paper trail. I hate to be the bearer of bad news...but this is exactly where you need a paper trail.

First of all, this is a great way to practice and practice makes perfect. Do you want to make your own and file them by a system that makes sense to you? Do you want to use a software suite to do it for you? How do you want to itemize products and services? This is when you get to explore and mistakes probably won't cost you too much. I say that, but I have to add this...

Secondly, family and friends probably won't stiff you, but making contracts and invoices a habit is good going forward. I did say "probably" because hopefully you aren't like me, but I made the mistake of not writing down an exact amount and lost over $1,000 on one of my first projects...for a family friend. Please, please, pleeeeease let my experience be your lesson so you don't make the same mistake.


Oh boy, see what I did there? You will have family, friends, and grocery store checkers who have advice for you. They will tell you what worked for their grand-daddy's shoe store during the Depression. They will wax poetic about the merits of a company credit card. They will whisper conspiratorily at you about their neighbor who made nefarious millions. There will even be people who blog and mean well, but don't know the in's and out's of our specific industry. (Ha.) The truth is, a lot of it is trial and error. The people who tell you they have it figured all out usually don't. And the people who will tell you they don't have it all figured out...they're usually closer in reality.

Take business advice like you take a margarita - with a big heaping helping of salt. I would advise you that listening is not only a best practice because it makes people happy to impart advice, but you'll learn a lot of things too: the good, the bad, and definitely the ugly. Let's focus on the good. There's lot of good advice out there. Take what works for you and leave the rest behind.

Pretty soon, you'll have lots of good advice for people starting out. You might even have a list of the top 5 things you did wrong that you hope other people can learn from and avoid.


You can always follow Pickles & Oliver on Pinterest for up-to-date tips for social media, blogging, design, branding, and small business success. I hunt down all the best advice from the pros and curate it for you in one place.

#smallbusiness #howto

  I'm Sydney: a branding enthusiast, web design maven, and social media mad scientist. This blog is a design and marketing resource for creative entrepreneurs as well as a space for exploring the "behind the scenes" of my own design process and portfolio. Read more...

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