The Good, The Bad, and The Best: Starting Your Own Business

Cofounders Char and Keith at their first shoot as Four Winds Creative.

Taking a risk can be, by definition, dangerous. Taking a huge risk, well, that’s where the real fun begins. I started a business almost three years ago with two wonderful partners, big ambitions, and bigger Moscow Mule mugs. Startups are increasingly popular, especially in the Bay Area. If you’re thinking about taking the leap into self-employment, here’s what I can tell you about my take on the Pros and Cons of owning your own business.


On my last day at a big corporation, feeling empowered.

Feeling in a rut at my job, I called my best friend, Emily, for advice. After some chit chat, I finally got the courage to ask her, “Em, should I stay at my job?” After a lengthy pause, which I later found out was due to a mouthful of food, she asked, “How long have you been there again?” I said “5 years and change.” It was her response that stuck with me for a long time. She said, “Are you going to call me 5 years from now and ask me the same question? Where will you be then? You’ll be almost 40 and still at the same company. Is that what you want?” That’s when it really hit me. No, that’s not what I wanted. After that call, it took me 3 more years to get the courage to leave a big brand corporation, to let go of the benefits, my work family, a generous salary, and bonus program to start my own company.

Cut to present day, and I’ve been a business owner for a whopping 2 years, 10 months, and 21 days . I might not be an expert on owning a business, but I’ve learned a lot of valuable lessons from taking the leap and becoming my own boss. I’m frequently asked about my experiences owning a business vs. working for one.

Here are my pros and cons:


  1. I define my own hours. Sometimes that can mean 16 hours days, but it can also mean 4 hours days or days off when I need to catch up on other things.
  2. What I say matters. My partners and I decided on the name, logo, brand, our mission statement, and our company values. I believe more in what we do because I had a large part in creating it for ourselves and our employees.
  3. Bye bye corporate BS. I don’t have to worry about performance reviews, how to ask for a raise, or status reports. We’ve created a culture that is transparent. We can talk to each other about anything, so if something isn’t working, we address it. It’s very refreshing after navigating processes and systems of communication for years.
  4. I get to choose who I want to work with. Ever get teamed up with THAT person who you know will drain the project of fun, positivity, and success? First off, do NOT become that person because that will happen if you lose all passion for your work. Second, if you work with that person, then it becomes a drain when you have to pick up where they slack off. Resentment builds and unhappiness ensues. Now, I get to work with people I want to see every day who I know can embody the company values of Fun, Freedom, Customer Service, and Quality. This goes for both crews and clients.
  5. I don’t have to do it all myself! I have two amazing business partners whose skills compliment mine and vice versa. I am very lucky to have found two very talented people who have similar goals, values, and complimentary skill sets. Starting a business can be very overwhelming, but having a team where someone’s strengths covers another’s weakness is an invaluable dynamic.
  6. I love what I do and where we do it. After the 3rd attempt, we found an office space with ample parking that doesn’t reek of downtown urine stained streets, and we have our own kitchen! Having a full-sized Air Hockey table doesn’t hurt too. Coming to work doesn’t feel like a job to me. And when I don’t want to come into the office, then I work from home. Flexible hours allow me to work when I want and where I want.


  1. I have access to less resources than working at a big company. I think we have one shared stapler in the office. Not because another stapler is out of budget, but because we don’t staple that often. When your company is small, you cut down on excess materials.
  2. Running a business keeps me busy. The feeling of needing to do it all doesn’t go away right away! In the beginning, it was a struggle feeling like the three of us had to juggle roles and wear so many hats. I felt like I had to be our office coordinator, admin, producer, social marketer, sales, and a business owner at the same time. What used to take me 1 day to manage a project, took me a couple of  REALLY long days plus more to accomplish what I could before.  What I found out was that yes, I could do it all myself, but to the detriment to my social life, health, and sleep. It took us about a year to identify where we were all struggling, define roles between the 3 of us, and eventually hire some badass employees to alleviate our work in the trenches so that we could focus on what matters the most: Owning and making our business work for ourselves and the clients we serve.PRO TIP: It’s okay to say no to clients, but offer an alternative solution or referral. Taking on any and all work is not only bad for you, but unfair to a client who is paying for a certain amount of quality and attention. I once took on a project I really didn’t have time to manage, and I wasn’t happy with the product we made, and it was painful for the client who thought I just wasn’t getting what they really wanted. Made us look bad and made me feel even worse.
  3. The decision on high volume vs high profit. While not necessarily a con, this is a recurring learning for my team. Right now, this seems like an “either/or” situation, but our Chief Strategy Officer, Todd Hallinan, has been working on the ability to have both. Is there a way to get high profit and high volume? It can be difficult as a small agency to strike a balance between internalizing work to increase profit and outsourcing work to give us more time to focus on growing the business. These are the quandaries you don’t have to worry about as an employee.
  4. More stress. I’m not going to lie. Owning a business can be stressful (if you let it). There have been times when I can’t sleep or I worry about the next big thing, but when we have a break in client work, that means more time I can spend on building our business, ourselves, and our employees.
  5. Networking. It can be scary putting yourself out there, and I’m an extrovert! To be candid, that constant fear of rejection and failure never really goes away. It’s a challenge to go up to strangers at networking events and talk about what we do and why we do it. You have to be okay with asking for work and practice your pitch every day. The more confident you come across, the more people will truly want to work with you.

Before I knew it, we even had our own mugs.

My biggest learning? Authenticity. I tell people all of  the time that we are the go-to video experts for tech  companies, but I don’t try to sell them on videos. Google “video production agencies” and you’ll find pages of vendors ready to take the gig. I  find that  what sets us apart from the crowd is when I talk about myself and why I do what  I do. Because I’m passionate about my business and what we create for people, it’s natural  for  them to want to work with us; that’s my favorite type of client, one who can see how much  we believe in our work. Once you start losing who you are in your business, then  step  back, reevaluate, and re-group. Find a business coach and learn from their mistakes.  You  don’t have to make all the mistakes when other people have done that for you and are willing to share how they overcame them. There is a HUGE network of entrepreneurs out there looking to share and learn. I count myself as one of them too, so if you want to connect, find me on LinkedIn and send me a note. I’d love to hear from you!

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