Becoming an Optimistic Teenage Company at our 2025 Retreat

Retreat is always one of my favorite times of the year. As a hybrid company with about half our team based in New Orleans—who get the perks of hanging out together year-round and enjoying summer Fridays—retreat is the one time we get pretty much everyone in town.

It’s our best opportunity to live up to our values, especially when it comes to supporting our communities, and it’s prime time for content creation since we’re all actually in the same place. Even if Retreats weren’t the most fun our company has, I’ve found they’re really crucial for setting a tone for the rest of the year. They’re one of the few chances to set aside the daily needs and burden of the immediacy, and focus on how we want our agency to grow and live up to your company vision.

This year was special for another reason: we hit 13 years. Thirteen years ago, on the exact day of our retreat, I sat down at my kitchen table after one of my three roommates had left the house and registered Online Optimism with the Louisiana Secretary of State. Pretty wild to see where it’s all grown. We’re officially teenagers.

So what did we get up to for our thirteenth year?

Supporting Our Communities

One of our core values is to support our communities, and retreat gives us the best chance to do that as a full team. This year, we focused on a couple of key initiatives.

Harm Reduction with Trystereo

We partnered with Trystereo to put together around 500 harm reduction bags. During the session, we learned about how effective harm reduction, and the challenges of focusing on this in Louisiana. But there are bright spots, particularly in Orleans Parish. For example, in 2018, Orleans Parish authorized Syringe Service Programs (which is why I get to publicly post about this.) It was a meaningful way to give back during what’s been a pretty challenging year for public health.

Optimists Learning ASL at the Online Optimism 2025 Retreat

ASL Training

We try to do some sort of educational experience to help our Optimists become better advocates and supporters of important causes. Since we do CPR training every other year (the certification lasts for two years), we use the alternate years for other training. Two years ago, we did a harm reduction course. This year, we brought in ASL training from New Orleans Sign Language Services.

It was a really valuable experience. We learned about the challenges that the Deaf community faces and why ASL is so important. A few of our Optimists even went above and beyond to learn the ASL alphabet.

Supporting Local Businesses

Supporting our community also means supporting local businesses. Yes, that includes restaurants and bars for some of our more fun events, but it also means working with small businesses and organizations that cater to groups.

One of our bonding experiences this year was at C’mere NOLA, a local spot where we made adorable little clay pizzas before heading out for actual pizza. We were apparently the largest group they’ve ever hosted—and I’d like to think we were just as fun as the bachelorette parties they typically deal with. As someone living in New York City, I don’t know if I can say it was the best pizza I’ve ever had, but the clay versions we made? Pretty darn cute.

We also kicked off our mornings with yoga sessions led by Nola Vibe Yoga, keeping things local and keeping our team energized. (Mercifully, our team didn’t take any pictures of me doing yoga this time.)

Operations Director Sara with her C'Mere NOLA Pizza

Setting Goals and Planning for Growth

Retreat isn’t just about fun and volunteering—we also dedicate serious time to planning for Online Optimism’s future.

This year, we broke up into departments to talk about what we’ve learned over the past year and brainstorm goals for the year ahead. During retreat, we keep things open and creative, really drawing out ideas and having honest conversations. In the upcoming weeks, we’ll solidify these into SMART goals so we can measure our success and work toward them for the next 11 months.

We also split up into smaller, randomized teams this year. We considered trying to create evenly split groups, but when you have so many people working in so many different areas, that’s tough to pull off. So our organizers decided to lean into a New Orleans tradition and use a cake pull to randomly assign teams. It was a fun way to mix things up and get people collaborating with team members they might not work with day-to-day.

Celebrating Often

We wouldn’t be Online Optimism if we didn’t live up to our value of celebrating often. That means it’s time for the annual OOies—yes, they’re based on the Dundies from The Office, because we very much are a millennial-core company.

We hosted the OOies at Copper Vine, and it was, as always, a blast. I was honored with the “It Was Never a Phase” award, celebrating both my existence as an Optimist and the fact that my Spotify is still mostly Blink-182 and NOFX. Bands that had their heyday back when we were still downloading songs off Limewire. It’s been a couple years since punk’s heyday, and while some people might have outgrown their old music tastes, I clearly have not. And neither has Online Optimism, apparently.

Looking Ahead

This retreat also marked a transition for us. We got one last all-team photo at our Soraparu office before we move (you’ll hear more about that later) and gave away as much swag as we could from our old brand. After 13 years with the same branding, it was a nice goodbye. Now we’re excited to use all the new merch that matches our 2025 rebrand.

As we wrapped up retreat, we took time to reflect on how far we’ve come and where we’re headed. With goals in progress, new skills learned, and our community stronger than ever, we’re Optimistic about what’s coming up in the year ahead.

Here’s to year 13—and to many more retreats filled with growth, giving back, and celebrating the Optimists who make this agency what it is.

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