Oh, how I love a team retreat – I get both excited and nervous and afterwards feel both so full and exhausted (in a good way!). Like all aspects of our lives, Zoom is never a substitute for in-person (IRL) connection. I have found that, like a long-distance romance, the more time we go without seeing each other, the harder it is to stay healthy and connected. We have multiple big shoots a year that most of us need to be on, but this year, someone was missing from all of them – in fact, this was the first time that Caitlin (LA) met Marlee (Portland) outside of Zoom. The LA team flew up and we went out to Oregon Wine country for three wonderful nights and today I’ll tell you all about it if you want :)

How I Plan Retreats…

Being a Virgo/Enneagram 7 is a real dangerous combination – I’m REALLY into having fun, but I fear that I’m also a bit controlling and rigid about how, when, and where we have said fun (and plan it down to the hour to ensure it’s ample, but not overwhelming). I always ask their input, but once they agree, they are mostly held hostage by my planning, which I personally think is a strength of mine (but, of course, I would think that). I really try to pack it in with unique, memorable experiences you can only get at the location we are in, and I splurge a lot to make sure we do it right. …And yet I had some real bossing to do this time. I needed to present my new employee handbook, with new PTO policies, updated bonus and commission structures, reworking a lot of workflow for efficiency, setting big and small goals, and lots of macro and micro brainstorming. Leading a team, running a company is so much like parenting for me – extremely fulfilling and gratifying, but not all parts of it come naturally to me. I can see my bad personality and management tendencies so clearly on a daily basis, and I actively have to fight against them. And yet other parts of the business I can sink so easily into and flow so well. At times I wish there was someone in operations, or HR, or finance (my “integrator” if you have read Rocket Fuel, a great business book for creatives) and yet, I want to stay a very lean company so I’ve made the choice to mostly take on those roles – for better or worse. Which brings me to this…

The A Team!

I am seriously so lucky to have ladies who have dedicated their work life to this company (to me and to YOU) for so long. As a reminder, I have 3 employees in LA still and 2 in Portland, with Kaitlin (our freelance photographer) being an honorary Portland team member. Jess, my editorial and creative director, is celebrating 9 years soon, Caitlin (queen of partnerships and revenue) and Mal (social media + marketing) celebrate 6 years in a few weeks. Gretch (my right-hand producer/creative ride or die) just celebrated her 2nd workaversary, and adding our newest social media manager, Marlee, is 4 months in and a much-needed final puzzle piece (Like finding a GD needle in a haystack!!! We found her!!! ). They are all so talented and creative and care, bringing different strengths to the team, and I consider being their boss/leader one of the greatest responsibilities and privileges of my life. Being so small means that we can all have deeper relationships with each other, which takes more work to remain connected and healthy, but so much more rewarding than typical coworkers. I know I can absolutely drive them nuts, frustrate them constantly… I mean, I act like a boomer with IT and violate my own HR “policies” LOL way too often.

Where We Stayed…The Carly FTW

The reason we even came to wine country is to stay here, after years of remodeling, The Carly was ready. My best friends are about to open this boutique estate hotel in Carlton, OR, called The Carly, designed in collaboration with my friend Max Humphrey, and we got to be the first guests to test it out. It’s a highly luxurious mini Soho House that has 5 suites in the main lodge (where we stayed) and was PERFECT for a warm, cozy, luxurious retreat. But then on top of all that, it’s filled with incredible design details and not an inch of drywall (so much tile, marble, paneling, awesome lighting, and art). They did such an incredible job, and every single thing was thought about. Here are some sneak peeks:

What We Did On Our Retreat

We attempted 4-5 hours of work both days, around the dining table, balanced with fun the rest of the day. On day one, we went to Red Hills Market for lunch (delicious) and then had a car service pick us up at The Carly to go wine tasting at two different vineyards – Soter and Radio Hills, both beautiful with exceptional wine. We ordered pickup from Wooden Heart for dinner (awesome pizza and cocktails), then with enough wine in our bloodstream some of us plunged in the pond before hours of talking about the pros and woahs of social media (and we may have gotten in a heated debate about the state of men in America right now) :) Team bonding!

The second day, some of us did a workout on the deck (mostly for brain endorphins) and after a few more hours of work, headed to McMinnville (adorable) for lunch at Cypress (delicious) and to pop into a bunch of shops.

Downtown McMinnville is pretty dang cute, and we also went to the Lafayette Antique Mall in an old school. I’m not pregnant, despite that photo hoping to cause a rumor! Then we headed back to The Carly (because we mostly wanted to hang out there by the cozy fire in the rain), and while we worked for a bit, a private chef, Brittany Baldwin, prepared our four-course customized spring meal. Like we sat and worked/talked, and had a happy hour while someone else cooked for us.

I’ve only had a private chef in a group once before, and it wasn’t the best experience, so I was nervous, but we literally couldn’t have been more delighted by her vibe and her food. Extremely delicious, with so many veggies coming from her own garden, the most scrumptious chicken and dessert (that we still talk about), and she even set the table and did all the dishes. Such a splurgy treat that we all agreed was 15/10.

The next day we woke up, had coffee and then I had to drive back to be with Elliot who had stayed home for the third day sick and was begging for her mama while my team got breakfast on their own (which I think is fun to have some time without me) before flying out.

I think the highlights for all of us were staying at The Carly (so beautiful and well done) and the private chef (we could get used to that) but we all also felt that the teamwork we did together was super productive and left feeling inspired and with a lot of clarity on how to approach this next year (rare for me). I don’t know what I would do without Brené Brown, y’all. Her leadership books are so clear, instructive, and inspiring. Running a thriving creative small business has been almost impossibly challenging for me at times. I’ve learned so much, grown so much, failed so much, and am really, really appreciating however much wisdom I feel like I have 15 years in (which is about 1 million times more than I had when I started, but still could use more).

So grateful for these beautiful ladies in my life (Kaitlin, you too!), for giving of their talents, brains, creativity, intelligence, expertise, and extreme thoughtfulness to me, you, and this company for days, months, and so many many many years. It was such a reminder of the importance of in-person connection and how much it really feeds our inner lives. And honestly just makes all the challenging work/digital/social media BS tolerable and worth it :)

Where should we go in September, ladies???? It’s our birthday month (we are almost all Virgos), so I figured it’s a good time to get together and gear up for Q4 (aka “finals week” for creators – work gets NUTS for a bit). If you want to rent out The Carly for a group/corporate/family retreat in Oregon’s stunning wine country, head here (you won’t regret it).

*Photos by Kaitlin Green