The InSide Gig Summit
September 1-6, 2026
Cascais, Portugal
Most people search outside themselves for the answers.
The secret to a great side gig? It isn’t the gig. It’s you.
Clarify. Connect. Create.
Blend your vision with real action
Walk in with a vision for change. Walk out with a plan.
You feel stuck in your dental career. You’re not having fun anymore, and you’re tired of carrying the pressure to please everyone around you. Some days you want a completely new career. Other days you don't know what you want. The mix of internal chatter and external noise has you feeling confused and even paralyzed.
Because you’ve invested so much into dentistry and the identity that comes with it, you can’t imagine life any other way. You’ve followed the practical, safe plan for so long that you’ve lost touch with who you are outside of it.
This is where you realize the side gig isn’t the gig. You are.
It’s not about looking outside for something to rescue you, but looking inside and becoming your own hero.
That’s your InSide Gig.
Join us in Portugal. When you step out of your normal environment, you can finally hear yourself again. You’ll be surrounded by dentists who are creating their own versions of a meaningful life. You can design your career to fit your life instead of forcing your life into your career. Having the right community by your side makes it possible.
THE RETREAT
Meet Your Host
Dentistry was supposed to be my dream career and provide a stable, impactful, comfortable, and successful life.
From the outside, it looked great. But on the inside, I was far from happy and fulfilled. Buried deep inside of me was someone who longed for creativity, spontaneity, and adventure in a way that clinical dentistry couldn’t provide. I just didn’t think I was allowed to choose differently.
After ten years of practice, I finally gave myself permission to explore a life and career on my terms.
Getting real about my career gave me the freedom and confidence to change. This unique path wasn’t modeled in dentistry at the time, so I had to figure it out on my own. Once I did, I knew I had to help others do the same. In 2018, I officially launched Lolabees Career Coaching to help dentists take back control of their lives and careers.
There is no one-size-fits-all definition of success in dentistry.
Whether you want to decrease your clinical hours and build a side gig, shift into a nonclinical career, or leave dentistry altogether, you get to choose. You define your success and how you want your life to look.
The InSide Gig Summit reflects that philosophy. It brings together meaningful work, deep conversation, play, travel, and space to think differently. My role is to guide the process and help you connect the dots between who you are and the vision you have for your life.
You don’t need to have everything figured out before you arrive. You just need to be open to listening to yourself.
Dr Laura Brenner
THE ADVENTURE
A Look at the Week
Arrival | Settle In
You’ll arrive at the villa in the afternoon, with time to settle in and land after travel. We’ll come together that evening for a welcome dinner on site to connect, unwind, and set the tone for the week ahead.
Focused Mornings | Spacious Afternoons
Most days begin with breakfast followed by structured morning sessions focused on learning, reflection, and meaningful conversation. Afternoons and some evenings are intentionally open, balancing on-site lunches, rest, pool time, and the flexibility to explore on your terms. Unstructured time often becomes the backdrop for the most meaningful conversations and insights.
Play | Travel
Mid-week we'll step away for a full-day group excursion to Sintra. Nestled in the hills near Cascais, Sintra is a UNESCO World Heritage site known for its historic palaces, dramatic landscapes, and forested paths that offer a refreshing shift in pace and perspective. It’s widely considered one of Portugal’s most iconic destinations.
Closing | Completion
We’ll gather the final evening to reflect, connect, and close the experience together. We’ll also come together one last time over breakfast the following morning for final integration before continuing on your journey.
Come for the connection and the fun.
Leave with the clarity and energy to design your life and career on your terms.
What Past Participants are Saying
Dr Vera Marques - Dentist
Dr laura collatz - dentist
Tim McNeely - Wealth Advisor
Dr Kiri-Gabriella Anderson - dentist
