Earlier this month, 688er and brand strategist, Caitlin Horton traveled to New Orleans for a weekend of networking, camaraderie, learning, and merry-making with a group of like-minded female entrepreneurs.

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Caitlin posing on a very artistic couch with content strategist Erica Midkiff and Sophie Davies of Prim’d Marketing

Caitlin’s Instagram pics from her trip piqued our interest, so we sat down with her to learn about her experience at Being Boss NOLA. Read on for feedback from Caitlin and to see her photographic tour of the weekend.

About Being Boss

Being Boss is a podcast that two creative entrepreneurs launched earlier this year, and somehow I found it right in the early days. The two hosts, graphic designer Kathleen Shannon (Braid Creative) and web designer Emily Thompson (Indieshopography), riff on their own businesses together or interview other folks to learn from them. It’s a bit like eavesdropping in on their conversations, which I really like.

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A group of Bosses took the ferry one afternoon to explore Algiers Point, the oldest part of New Orleans.

At some point they opened up a Facebook group for listeners, and it’s really one of my favorite online communities. It’s full of creative entrepreneurs running all different types of companies at all different stages of business. It’s very friendly and supportive, and I always know that I can get great advice in there. I even found a fantastic assistant for my brand strategy business through the group. The community is a huge resource.

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You can find dozens of houses just like this while wandering around the French Quarter. Major color palette inspiration!

Being Boss in NOLA

All of a sudden, there was a chatter in the Facebook community about wanting to do a group vacation. When Kathleen and Emily officially announced the city would be New Orleans I knew I had to go. Not only did I want to meet people from this community in real life, but NOLA is also my happy place. So I bought a ticket right away.

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Erica Midkiff snaps a photo of Sophie Davies and Jenni Brown, business partners at Prim’d Marketing in San Francisco.

Who’s Who¬†

The group skews female for sure, although there are several dudes in the community who are great. About 75 of us ladies showed up in NOLA though, ranging from brick-and-mortar shop owners to designers, marketers, photographers and other typical “creative” entrepreneurs. Our little community’s attorney, she focuses on creative businesses, came to meet us in person! So there was a really wide range which is something that added to the experience because you get out of your own bubble so much that way.

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First day meet-and-greet by the pool at Le Meridien in downtown New Orleans.

The Goings On

The first thing we all did was hang out by the pool at Le Meridien in Downtown New Orleans. That meet-and-greet carried over to a cocktail party sponsored by Freshbooks and Acuity Scheduling at a really cool tiki bar in the French Quarter. The next day we met up in the morning for a masterclass, and then we just hung out together. A group of us took the ferry to Algiers Point to wander a bit that day. Then we all met up at a few restaurants for community dinners. Saturday morning was a live podcast recording, which I can’t wait to hear! [You can now listen in to the live podcast right here.] I went to lunch at St. Roch Market in the Bywater with a few other ladies and really enjoyed hanging out with them that afternoon. That night we all met up for a ghost tour, which was cool.

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Details at Tiki Tolteca

The Takeaways

There’s not one big thing I can say that I learned. I think It wasn’t really structured to give you a few big takeaways like a conference with several big speakers or something like that would. Instead, it was more about the conversations that happened “unofficially,” so to speak. I got to spend time with business owners who have different parts of their business a bit more worked out than mine is, for example, and got some really great tips from them. Someone shared with me how they avoid overbooking themselves, and it was soooo simple but really eye-opening. Just stuff like that really.

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Sarah Ball of Mango Sticky exploring the architecture of Algiers Point.

I plant to stay in touch with the people I made strong connections with… I can’t wait to see what they get up to this year. I’m looking forward to seeing their businesses grow!

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Up Next…

I’ve been planning a business retreat for a couple of months now where I’ll be taking a long weekend and holing up in a cabin to do some serious planning and rebooting a few of my services. Over the last year I’ve been taking a lot of notes on how to better serve clients and I’m very excited to unplug and take the time to plan those things out. Several of the tips and strategies I learned about during Being Boss NOLA will be integrated into the work I do on my retreat.

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As for Being Boss I can’t really speak to what Kathleen and Emily have planned, however it does sound as if future trips are already in the works, so anyone who missed out this time can join in the fun. I imagine several of us will sign up for a second go-round too!

Being Boss_Group Pic 1If you want to see more pictures from Caitlin, check out her Instagram feed @dizzycaitlin. Find lots of images from everyone on the trip at #BeingBossNOLA.


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I'm a native Memphian, a University of Memphis alum, and a writer. I enjoy taking in the sights, sounds, and tastes our wonderful city has to offer. Pros: I'm bookish and fancy myself a good conversationalist. Con: I talk about cats and Crossfit more than most might appreciate.

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