So it’s official: I’ve been running Small Hat Studio for a whole year. That’s 12 months of designing, managing clients, overseeing printing, seeking out new business, invoicing, paying taxes and meeting with a lot of advisers along the way. At times it’s stressful, at other times it’s frustrating, but in the end it is always rewarding. This is because I’m following my dreams, pursuing my goals and ’doing it my way.

In this calendar year I’ve learned a lot, and I thought it would be fun to share some of that knowledge with anyone who aspires to run (or start) their own business.

1. True wisdom comes from knowing that you know nothing.

This paraphrased thought is attributed to Socrates—the father of modern philosophy. Was I a philosophy major in college? Sadly (or thankfully?), no. I remember this from the 1989 movie “Bill and Ted’s Excellent Adventure”. Now that is sad.

That's totally me, dude!

That's totally me, dude!

What I derive from the quote is this; while I may know graphic design inside and out, there are many subjects on which I’m not an expert. These include small business law, business practice in Texas, state and federal tax codes, and planning for my long-term financial success.

Before you go into business for yourself, make sure you’ve lined up a stable of knowledgeable advisers. These include a lawyer, an accountant, a financial planner and a mentor in your professional field. Ask these people a lot of questions—even if you think you know the answers. Listen to and heed their advice, because it might help you navigate business pitfalls that could potentially endanger your success.

2. Enlist the help of dependable vendors.

If you’re a baker, you’ll need to purchase ingredients. If you landscape yards, you’ll need tools, gas for your lawn mower and a ton of mulch. In my case, sometimes I need printing companies, web developers, writers, proofreaders, photographers and illustrators to do my job. 

The point is this—no matter what you choose to do to make money, you’re probably going to need help. Make sure you know your vendors can offer what you need, when you need it, and at a reasonable price. You can’t put a dollar figure on dependable vendors. Good ones will make you look great in your client’s eyes, and bad ones? When bad vendors stumble, it will be you taking the fall.

3. You’re going to piss some people off.

You know the saying “It’s just business”? Well, yes and no. Business can be a game of numbers, but make no mistake—business can get personal. It can get messy. Feelings can get hurt. It can divide friendships. With that said, always keep in mind you’re going into business to make your dreams a reality. Not someone else’s. And so long as what you’re doing isn’t illegal, other people can keep their opinions and hurt feelings to themselves.

If you do end up angering a client, co-worker, friend or former employer in a professional capacity, you have some options. Ideally, you should deal with the disagreement head-on. If this is not feasible, just know you have to deal with the consequences no matter whether they are good, bad or indifferent.


4. Stay positive.

In addition to the possibility of personal ups and downs, you may experience some professional ups and downs. Future projects may get awarded to another person or agency. A job you thought would be fun and easy turns into a death march. Maybe something you produced had a mistake and you have to redo it at your expense. Regardless of what happens, keep a positive attitude and remember... things could always be worse.

Just like most business owners, I have my fair share of frustrating moments. To get though them, I take a little time out of my day: I get up and move away from my desk. I take the dog for a walk and spend the time figuring out a solution to the dilemma presented to me. These crucial minutes away from my desk help me gain perspective and keep me from sending what might be an email I will later regret.

5. Establish the basics before you begin doing business.

A good first step on the road to business ownership is to figure out if you will incorporate your business (your lawyer and accountant can help you answer this question and determine what kind of legal entity is right for you).

As a next step, open a checking account for your business to keep personal and professional finances separate. This is crucial from a legal and a taxation standpoint (once again, ask your lawyer about the protection this affords).

Third, meet with your accountant and mentor and find out which governmental agencies (local, state and federal) your business will need to report to. Being in the bad graces of a governmental agency—say the IRS—is a nightmare. It will drain your time, your patience and probably your checking account.

Last—but not least—spend time figuring out how you will issue estimates and invoices, and track expenses. Personally, I use a subscription cloud-based accounting software called Freshbooks, but there are lots of other options including Quickbooks, XERO and Kashoo. Check them out and decide what works best for you.    

6. Work every day, but if you have nothing to do, enjoy it.

A big part of being self-employed is having good time management skills. (Note: I didn’t mention “multi-tasking”. I’ll explore why that term is a lie in a future blog post.) Make sure you’re going to put in the necessary amount of work hours to be successful. Work on various things each day, including projects that make money, invoicing, and responding to client emails. Try to squeeze some of this stuff in whenever you can so it doesn’t become overwhelming later. You can respond to emails while watching TV. You can invoice while your dog goes outside. You can work when your kids are sleeping.

Here’s the trade-off! If you’ve finished everything on your list of professional to-dos, enjoy your day. One of the best pieces of advice I received from my friend Laura McFerrin-Hogan was this (I’m paraphrasing again):

“For the first 10 years I was in business, I used to freak out if I had nothing to do or no projects to work on. How would I make money? How would I pay my bills, vendors or employees? It drove me crazy. Then I figured out things were going to be all right. Business would make its’ way to me. So now when I have nothing to do, I play with my sons or go see a movie. I’ve learned to enjoy my time off.”

7. Stay flexible.

Business can get personal. It can get messy. Feelings can get hurt.

Business can get personal. It can get messy. Feelings can get hurt.

One key reason I wanted to be my own boss? Three little words: flexible work hours. I have the ability to work as much or as little as I want. As long as the work gets done, it doesn’t matter if I work during the day or late into the wee hours of the night. 

But keep in mind that a flexible work schedule is a double-edged sword. While I can attend a two-hour lunch with a client, there may be times I have to give up hours of my day to work on a last-minute project, or I have to show up late for a social engagement because of a client’s immediate need. These are the demands of my job, and these are the trade-offs you’ll have to make to make a living. 

8. Don’t be all about the Benjamins.

There are a lot of motivations behind starting a business. These can include the need for a creative outlet, a sense of altruism, or even introducing a new product into the world the likes of which no one has ever seen. But one of the largest motivators is money. You’re in business to make money. If you don’t, then what you’re doing with your time is just a hobby.  

We all need money. We all like money. We all know it can make our lives easier. However, if you’re only motivated by money you might be miserable when it comes to business. Let me explain that last statement in a little more detail.

When I think about accepting a new project, I use a really simple litmus test. It goes like this. The ideal, pie-in-the-sky project should have three elements: I get to work with people I like, I get paid well, and I get a great piece at the end of the day. Projects like these don’t come around very often, but it is CRITICAL that every project I work on fulfill two of the three criteria. For example, if I’m not getting paid well, the project should be for someone I really like and I should be able to look back and say, “that’s a possible portfolio piece!”.

Now let’s take this one step further. What if I get paid really well, but the client is ungrateful and angers me every time we talk, and the work is both boring and monotonous and won’t be something I can proudly display in my portfolio? If this is the situation, the money just isn’t worth it, in my opinion. Keep your money; I’ll keep my sanity, thank you.  

9. Be yourself. Be genuine.

Your business should be a reflection of your values and your goals. If you’re more comfortable in a pressed suit, button-down shirt, and wingtips—awesome. If your personal style demands blazers in fun colors, designer jeans and sneakers—let your freak flag fly. Want to start your days at 5am or 10am? You get to choose, because at the end of the day, you can run your business however you see fit.

10. Never stop learning.

One of the first blog posts I ever published was a warning against complacency. You can read about it here. I’ll reiterate that warning here. 

Are you a great designer who struggles with content? Learn how to become a better writer so you can craft headlines and body copy. Do you specialize in web design, but your print skills are sorely lacking? Take on small print jobs and work with a reputable printer to learn the ins and outs of print production. When it comes to creating logos, do you struggle with execution? Take a continuing education class and gain insight into the do’s and don’ts of good logo design. 

No matter what your chosen profession is, make sure you’re always striving to become better, because it’s only by learning new skills that we stay relevant and marketable.

In reality, I’ve learned so much more than this in the first year—both about business and myself. But the real truth is, I hope I can take my own advice. I want to keep learning more, because I never want to stop this journey.