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

Clarify. Connect. Create.

Blend your vision with real action

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.

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

THE RETREAT

The Setting

Just thirty minutes from Lisbon, Cascais is a bright, walkable coastal town known for its relaxed atmosphere and beautiful shoreline. It’s the perfect setting with both easy access and the charm of a relaxed European seaside town.

This beautiful villa sits right by the water and is a short walk from the historic town center. Designed with open indoor and outdoor spaces that support ease and immersion, it offers everything you need close by. That freedom lets you step back, reset, have fun, and fully engage in the Inside Gig Summit.

A limited number of spots include overnight accommodations at the villa (double occupancy), offered on a first-come, first-served basis. At this time, one villa room remains — a king room, best suited for a solo guest or someone attending with a partner. Please reach out with any accommodation questions prior to registering.

Explore our luxury villa here.

The Setting

Just thirty minutes from Lisbon, Cascais is a bright, walkable coastal town known for its relaxed atmosphere and beautiful shoreline. It’s the perfect setting with both easy access and the charm of a relaxed European seaside town.

This beautiful villa sits right by the water and is a short walk from the historic town center. Designed with open indoor and outdoor spaces that support ease and immersion, it offers everything you need close by. That freedom lets you step back, reset, have fun, and fully engage in the Inside Gig Summit.

A limited number of spots include overnight accommodations at the villa. These rooms will be offered on a first-come, first-served basis. At this time, one villa room remains — a king room, best suited for a solo guest or someone attending with a partner. Please reach out with any accommodation questions prior to registering.

Explore our luxury villa here.

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

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.

Dr Laura Brenner

You don’t need to have everything figured out before you arrive. You just need to be open to listening to yourself.

THE ADVENTURE

THE ADVENTURE

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.

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.

Come for the connection and the fun.

Leave with the clarity and energy to design your life and career on your terms.

The DETAILS

Here’s what’s covered, and what’s intentionally left open, so you know exactly what to expect.

What’s Included

  • Five nights luxury villa accommodation (double occupancy) for the first 6 registrants. Only 1 King Room left.

  • Daily group coaching sessions

  • Breakfast, lunch, and select group dinners

  • Group Excursions including a full day trip to Sintra, a UNESCO World Heritage Site

  • All taxes and local fees

  • 10 CE Credit hours

What’s Not Included

  • Airfare to/from Portugal

  • Airport transfers (arrival/departure)

  • Select dinners, snacks outside of group events

  • Personal purchases or souvenirs

  • Travel insurance

  • Additional spa services or private treatments

  • Activities outside the listed program

Optional Add-Ons

  • Come early for a few extra travel days. Join us on August 30 for 2 nights in Lisbon. We'll have the opportunity to settle in and explore the city together before we head to the seaside town of Cascais on September 1. Includes 2 nights in a 4-star boutique downtown hotel + transportation from Lisbon to the Retreat Villa on September 1.

  • Want to bring a Plus One of your family? This retreat content is designed for all people aged 18 and up, so you can register additional guests. If you have family who would like to attend meals and excursions only, a reduced rate is available for them. We'll also offer hotel accommodations within a 2-minute walk, so you can bring your whole family. Have questions about bringing a guest or family? Book a quick call to talk it through.

Optional Add-Ons

  • Come early for a few extra travel days. Join us on August 30 for 2 nights in Lisbon. We'll have the opportunity to settle in and explore the city together before we head to the seaside town of Cascais on September 1. Includes 2 nights in a 4-star boutique downtown hotel + transportation from Lisbon to the Retreat Villa on September 1.

  • Want to bring a Plus One of your family? This retreat content is designed for all people aged 18 and up, so you can register additional guests. If you have family who would like to attend meals and excursions only, a reduced rate is available for them. We'll also offer hotel accommodations within a 2-minute walk, so you can bring your whole family. Have questions about bringing a guest or family? Book a quick call to talk it through.

Travel Support

Elevate Your Experience with Our Personal Concierge. Your journey shouldn’t feel like work. To ensure your trip is as seamless as it is indulgent, we’ve partnered with Dr. Karen Tindall of Globe & Co., an expert at curating luxury travel for dental professionals. Beyond handling your villa transfers and stay extensions, Karen uses her elite industry connections to secure VIP perks and exclusive amenities for your additional travel. As a former orthodontist and dental life coach who lives the Side Gig Way, she knows exactly how to add that extra layer of luxury to your time away.

How it works: Once you register, we'll connect you with Karen to support any additional travel needs beyond the retreat.

Dr. Karen Tindall

Dr. Karen Tindall

Travel Support

Elevate Your Experience with Our Personal Concierge. Your journey shouldn’t feel like work. To ensure your trip is as seamless as it is indulgent, we’ve partnered with Dr. Karen Tindall of Globe & Co., an expert at curating luxury travel for dental professionals. Beyond handling your villa transfers and stay extensions, Karen uses her elite industry connections to secure VIP perks and exclusive amenities for your additional travel. As a former orthodontist and dental life coach who lives the Side Gig Way, she knows exactly how to add that extra layer of luxury to your time away. Once you register, we'll connect you with Karen to to support any additional travel needs beyond the retreat.

Dr. Karen Tindall

Join Us

A small, intentionally designed experience in Cascais, Portugal.

Villa accommodations (double occupancy) are included for the first six registrants. Only two spots remain in the final shared king room.

I'm Ready!

Program fee: $5000

A $1,000 deposit reserves your spot.

I'm Ready!

Program fee: $5000

A $1,000 deposit reserves your spot.

Curious to learn more?

Let's chat.

Questions about fit or logistics? Happy to talk it through.

Curious to learn more?

Let's chat.

Questions about fit or logistics? Happy to talk it through.

What Past Participants are Saying

Dr Vera Marques - Dentist

Dr laura collatz - dentist

Tim McNeely - Wealth Advisor

Dr Kiri-Gabriella Anderson - dentist

FAQs

How do I save my spot at the Summit?

A $1,000 deposit reserves your spot. Because this event is intentionally small and villa space is limited, deposits are non-refundable.

Your remaining balance is due by June 1, 2026.

Registrations made after June 1, 2026 require payment in full at the time of registration.

If you’re unable to attend, you may request to transfer your registration to another attendee you invite to take your place, pending approval. While I’m happy to help where possible, finding a replacement is ultimately the responsibility of the original registrant. Refunds are not guaranteed.

What is the cancellation policy?

Because this is a small, limited-capacity experience, all deposits are non-refundable.

If you’re unable to attend, you may request to transfer your registration to another attendee you invite to take your place, pending approval. While I’m happy to help where possible, finding a replacement is ultimately the responsibility of the original registrant. Refunds are not guaranteed.

What will our days look like?

Subject to change:

Most mornings will consist of 3-4 hours of intentional activities and discussion to help you clarify your vision for your life and career. Through guided exercises and conversation, we’ll help you identify and move through barriers, fears, and assumptions that may be keeping you stuck or second-guessing your next move. This work is often deeply clarifying and helps people get more honest about what they want, along with clearer next steps for moving forward.

Breakfast and lunch are typically provided at the villa so you can focus on the experience and ease into the day. Afternoons and some evenings are intentionally open, giving you time to rest, enjoy the area, explore town, or simply take space for yourself. That space is an important part of the retreat, giving you room to integrate what’s coming up.

Mid-week, we’ll take a full-day group trip to the UNESCO World Heritage town of Sintra. Sintra has long been known as a place people retreat to for perspective and reflection. These shared experiences and unstructured moments often create the space where the most meaningful insights and conversations emerge.

Can I bring a plus-one or family ?

Absolutely. You’re welcome to turn this into a bigger trip if you’d like. Many participants bring a spouse, partner, or family to enjoy Cascais while they’re in retreat sessions.

Here’s how it works:


(1) Spouses or partners staying at the retreat villa are booked at the standard program rate of $5,000 USD per person, whether or not they are participating in the retreat programming. This rate applies to anyone staying at the villa.

(2) Families and children are welcome to travel with you and stay nearby in a hotel or rental. The retreat programming itself is designed for adults, but you’re welcome to vacation as a family around the retreat schedule.

(3) Non-participating guests who are not staying at the villa may join group meals and excursions at a reduced guest rate of $2,000 USD. Availability is limited, and we’re happy to talk it through.
(4) For guests attending on their own and requesting single occupancy at the villa, availability is limited. At this time, the only remaining villa accommodation is a shared king room (two spots). Solo occupancy of the king room, if available, is offered at a program fee of $8,000 USD and is confirmed via a brief conversation prior to registering.

Rooming: Villa rooms are double occupancy. Single room requests are limited and subject to availability. At this time, the only remaining villa accommodation is a shared king room (two spots).

Will I receive a CE certificate?

Yes. You’ll receive 10 Dental CE/CPD credits for participating in the retreat.

As a professional development experience, the program fee may be eligible for continuing education funding or potential tax deductions. Acceptance of CE/CPD credits is subject to local jurisdiction requirements, so please check with your licensing board, accountant, or advisor for guidance specific to your situation.

How will I know what to plan for?

Once you’re registered, we’ll be in touch with everything you need to know before you arrive.

We’ll walk you through what to expect, help you think through travel and arrival, and share practical details well in advance so you can focus on the experience itself, not the logistics. You won’t be left figuring things out on your own.

Can I plan to attend solo?

Many participants attend on their own, and you won’t feel alone here unless you want to be.

While there’s plenty of free time built into the experience, this is a small, welcoming group, and community naturally forms throughout the week. Whether you’re sharing meals, joining excursions, or simply sitting by the pool, you’ll have easy opportunities to connect without pressure.

Please note that villa rooms are double occupancy, and single-room availability is limited. If you’re attending solo and have questions about rooming options, please schedule a quick call so we can talk through availability and details prior to registration.

Do I have to be a dentist to attend or to get value from this event?

No. While the Summit is rooted in dental career conversations, the experience itself is about people, not job titles. Dentists, hygienists, dental professionals, and professionals from other backgrounds are all welcome. If you’re navigating questions around identity, direction, fulfillment, or what you want next in your work and life, this experience is designed to meet you there.

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