Real Jane at Work: Interview with Caitlin McCabe, Social Media Entrepreneur

I’m so excited about a new series here called “Real Jane at Work,” interviews with young career women who are getting. sh!t. done. The plan is to pick interesting, inspiring gals who will give us glimpses into their lives and share their wisdom.

And who better to kick things off with than Caitlin McCabe?

At 29, she’s the founder of a boutique social media company and a fantastic blogger on all things social media, marketing, and her life as an entrepreneur — a lifestyle she calls “location independent.” I’m a big fan of Caitlin’s blog, Smile Like You Mean It, where she talks about her career and company. I was so excited to ask her some questions, and she’s provided some great insight into what it’s like to be your own boss. Read the interview below!

You own your own boutique social media company. What did you do before you decided to fly solo?

Caitlin: I have a degree in Journalism from the University of Iowa and worked for a newspaper for about a minute before they told me that I was too opinionated for article writing. I remember being devastated and thinking my career was over. I ended up getting a job several years later at a radio station helping gather news stories for the news department and one day when a copywriter was sick I had to write some commercials. By the end of the year I was writing ALL of the commercials for the station and also had a morning talk show. That’s how I started in the advertising world. I also opened a business in Milwaukee that was PR and events which taught me a lot but I wasn’t ready at that time. I needed to learn more and went back to the corporate world.

How did you become interested in online marketing? Did you look for a career that afforded a lot of independence and flexibility or are those just happy job perks?

Caitlin: Believe it or not I got into social media through fashion. I was planning and producing fashion shows in Milwaukee (I know, I know Milwaukee isn’t a fashion mecca but we did some cool shows there) and I was promoting the shows using Myspace. I realized that my online efforts were working much better than fliers and ads so I started to learn more about how to use the internet for marketing. I got into social media because I thought it was a really interesting industry but eventually I did go off on my own for the freedom. I just don’t believe that you have to be in an office everyday to get work done.

When did you decide to start your own company? How did you prepare yourself for the risks involved?

Caitlin: I was really nervous about starting my own company and for a long time I viewed it as a stint in freelancing. Once the projects got bigger, I got more comfortable and was able to say “ok, this is a real company now”. Before I went off on my own I did everything I could to boost my network. I went to every networking event and conference that I could and spent a lot of my free time building my blog traffic. The more you can build your network the more likely you will be able to start your business with work coming in right away. I think another way to prepare yourself for the risks is to figure out how much you spend in a month and save until you can pay yourself for three months without taking in a single dime from the company. No one can be a creative business owner while they are past due on every bill and to expect that you will bring in tons of money in the first few months is unrealistic.

What were some of the practical hurdles you had to jump over when you formed your company? What resources did you look to for help?

Caitlin: One of the biggest hurdles that you have to deal with when you start your solo venture is how to meet people. Having worked in an office for a long time there are lots of ways that clients come in and you have a built in social setting. Going to local entrepreneur and networking events has been a lifesaver.

As for resources, I am an online dork so I look everything up online. :) How to write an invoice, how to file papers, everything! The best tool I have found so far is teuxdeux.com which is an online to do list – it’s amazing! I also think it’s really important to have heroes as a business owner. There are no real road maps for you so it’s really helpful to be able to have a someone whose business style you like to guide you a bit. One of my first, and remaining, guides has been Jason Baer.

You’ve written posts about your “office”—a coffee shop with a particular chair you like. What’s a typical day like?

My typical day:
6:30 – wake up and have coffee while I check emails and open up my teuxdeux.com list. This is my most productive time of the day so I’ll dig into research or writing projects that require a lot of thinking time during the morning.
9:30 – short break where I either go to the gym or think about going to the gym but read magazines instead.
10:30 – back to work projects, usually at a coffee shop. I choose my coffee shop based on the atmosphere. It’s weird but some shops are so much better for blogging and strategy and others are better for paperwork.
1:30 – By afternoon I usually start getting into meetings and calls since I am much more social in the afternoon. I also catch up on industry news or browsing through gadgets and other interesting things I think my readers will like.
6:00 – by 6 I’m pretty burned out and want to cook dinner or have some wine with friends.
11:00 – this is about as late as I go on a weeknight – being a business owner definitely puts a damper on Tuesday nights out.

What about your work wardrobe?

Caitlin: I just love clothes and my other dream job would have been in fashion events so I spend way too much time / energy / money on clothes. I think the business suit look can be way too stiff for a lot of women and there are so many ways to look nice without it. My go to outfit for a meeting is a black pencil skirt with a nice shirt or a dress (I love Brooklyn Industries, BCBG, and Anthropologie for dresses and Uniqlo has really amazing basics). If you don’t live in a shopping mecca there are some great sites out there like Polyvore.com where you can see a lot of stores on one site.

As a business owner, blogger, speaker, media strategist, and otherwise creative thinker, you wear a lot of hats. The organization and logistical details required must be challenging. How do you stay organized? How do you determine what’s the best use of your time?

Caitlin: Staying organized is really one of the hardest parts about having a business because no one really teaches that (or else I skipped those days in class). I tried a million different ways until I found what works for me. I paid hundreds of dollars a month for online organizers and sites to send reminders. What really works the best for me is a simple to-do list and some organized files on my desktop. The reason it works so well is that it can’t be 100 items long — it can only have 10 or so things on it so I think before adding it. This also helps weed out things that aren’t the best use of your time. For me, I’ve found a combination of work projects, marketing, and network upkeep has to happen every day. If I miss one of those things, my business suffers and if something isn’t in one of those categories I think twice about how much time I have before I add it to my schedule.

What do you love about your job? What do you hate?

Caitlin: One thing that I really love is being able to have a vision for my career and company. I am really motivated by thinking ahead and if I didn’t own the company it would be hard to say “in 5 years, I’d like this company to have 5 more employees” because it wouldn’t be up to me. My job allows me to have bigger goals…. and have a 3 hour lunch if I want.

The thing that I dislike the most is having to deal with really scary moments on my own. I might have people working on projects with me but at the end of the day, I alone have to deal with every consequence of the company decisions.

What do you know now that you wish you knew then?

Caitlin: I think I gave up too early on my first business and I wish I would have known that persistence is absolutely essential to survive. I always tell people that most people stop blogging after 2 months because they don’t have any readers. Readers come after time and if you give yourself 2 months to build a blog you’ll be disappointed. I think having your own business is very similar – it might take a year at least to feel like you’re even remotely successful.

Thanks Caitlin!

you might also like:

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2. Conversation: Good idea to connect with colleagues or bosses on social media?
3. Entrepreneur Tools: Design*Sponge Biz Ladies
4. How to Write a Thank You Letter after an Interview
5. Guest Advice: How to Stay Calm in Your Job Interview

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