Skip to content

It's time to stop under-living and create a life you're OBSESSED with.

And that journey? It starts right here.

With The Obsessed Retreat.


You deserve more than a life you tolerate.

You deserve a life you LOVE.

A life where...

  • You don’t feel stuck. 
  • You know exactly what you want.
  • And you go after it and pursue it relentlessly.
  • You don’t self-sabotage.
  • You prioritize your own happiness.
  • You have fun. 
  • You live big. 
  • You love hard.
  • You adventure.
  • You have deep, meaningful relationships. 
  • You know exactly who you are.
  • And you let that version of you be known and seen in the world. 
  • You set wild, outlandish goals.
  • And you accomplish them. 
  • Because you’ve become someone who takes massive action no matter what.

If that's what you want for yourself, join me in Miami in March.

For The Obsessed Retreat.

A three and a half day immersive, in-person personal development retreat designed to teach you everything you need to know to create a life you're OBSESSED with.

Here's a SNEAK PEEK of the event.

(Psssst... Sound on.)

More specifically...

Here is what you can expect when you attend The Obsessed Retreat.

The Obsessed Retreat takes place over three and a half days.

The next retreat will be hosted in Miami Beach, Florida from March 20, 2024 to March 23, 2024.

Here is an overview of the event schedule.

3.20.24: The Welcome Reception

3.21.24: Workshop Day One (All Day Training)

3.22.24: Workshop Day Two (All Day Training)

3.23.24: Workshop Day Three (All Day Training) followed by The Farewell Dinner

You'll want to arrive no later than the afternoon of March 20th and depart no sooner than the morning of March 24th.

The Welcome Reception

On the evening of March 20th, The Obsessed Retreat kicks off with The Welcome Reception. The Welcome Reception is hosted at The Betsy Hotel, the venue for the retreat. You'll come meet me and your fellow retreaters. We'll spend the evening wining and dining over exquisite cocktails and hors d'oeuvres, getting to know one another, sharing stories, exchanging laughs, forming bonds and building relationships that will last a lifetime.

Workshop: Day One

The next morning, we get to work. The day starts with breakfast at 9:00 AM (you're on vacation, so you get to sleep in) followed by a full day of learning, coaching, growing, transforming.

Day One is all about solving problems.

We'll start by identifying the problems you're currently facing. We'll get clear on what's holding you back, keeping you stuck and causing you to indulge in inaction. Then we'll determine what you need to do to overcome the obstacles in your way.

Workshop: Day Two

Just like Day One, Day Two starts with breakfast at 9:00 AM.

Then we get down to business.

Workshop Day Two will focus on developing skills.

The essential skills you need to live a life on your own terms.

For the March 2024 retreat, we'll focus on developing the skills of decision making and practicing constraint. Both of these skills help you simplify your life so you can have the space you need to create a life you absolutely love.

Workshop: Day Three

Our third and final day together commences with breakfast at 9:00 AM.

After breakfast, we embark on Workshop Day Three, which is all about making plans for the future.

Together, we'll set goals and make plans to achieve them. I will help you iron out exactly what you want to accomplish for 2024 and we'll lay out the precise plan you'll follow to get there.

You'll leave Miami crystal clear on what you want for your life and what you need to do to create it.

The Farewell Dinner

Finally, our time together concludes with The Farewell Dinner, a decadent, gourmet, plated dinner in one of Miami Beach's most sophisticated restaurants. The food and drinks? They'll surpass anything you've experienced at any other retreat. Guaranteed.

I take event hosting seriously.

Yes, I want you to come change your life.

But I also want you to have THE TIME OF YOUR LIFE.

Which means everything--the location, the venue, the service, the food, the drinks, all of it, will exceed your wildest dreams.

For our last night together, you'll spend the evening celebrating.

The connections you've made.
The friendships you've formed.
The breakthroughs you've had.
The skills you've built.
The decisions you've finalized.
The goals you've set.
The plans you've made.
And the success you will inevitably achieve once you return home.

Monthly Group Calls

Speaking of returning home...

I want you to have ALL of the support you need to make your success inevitable.

So, on top of the incredible three and a half days we spend together, when you enroll in The Obsessed Retreat, you get LIFETIME ACCESS to monthly group coaching calls.

The Obsessed Retreat Member Portal

In addition to the monthly group coaching calls, you will also get LIFETIME ACCESS to The Obsessed Retreat Member Portal--an online platform where you can stay connected to the other folks you meet at the retreat, review event recordings and other trainings on demand, and get ongoing support from me, your coach, and the rest of The Obsessed Retreat community.

What does that mean exactly?

Have a question or need coaching on an issue in between the monthly calls? Bring it to the Member Portal and I'll respond to you in writing.

Have an accomplishment you want to celebrate? Bring it to the Member Portal.

There will be no shortage of support in The Obsessed Retreat community.

The connection you've been craving? You'll find it here.

What's it like to work with me?

Now listen...

I know you've tried some things on your own already.

With varying degrees of success.

Maybe you're discouraged. Or confused. Or just plain stuck.

I get it.

I see you.

I've been you.

Which means I know exactly how to help you get where you want to go.

Here's what you need to know...

Doing what you've always done won't work.

If you knew what you needed to do to create the life you want to be living, you would have done it already.

That's where coaching comes in.

When you work with a coach, you learn what no one has ever taught you.

You learn the root cause of what's keeping you stuck.

You learn how to stop indulging in inaction and move forward.

You learn how to design your future intentionally.

And you learn how to reverse engineer that vision.

To create a roadmap you can follow to create the results you want.

That's exactly what you'll learn to do at The Obsessed Retreat.

You'll master living an intentional life.

A life you're truly OBSESSED with.

Where will the The Obsessed Retreat take place?

At The Betsy Hotel.

Welcome to Miami.

Will I see you in South Beach?

How do you know if The Obsessed Retreat is right for you?

The Obsessed Retreat is a perfect fit for you if...

  • You are paralyzed by stress and overwhelm and are struggling to get through what life throws at you day to day. You suffer from perfectionism, have a habit of procrastinating and can’t seem to stop people-pleasing others. These traits? They’re the perfect storm for staying stuck, which is exactly where you find yourself. And you’re confused about what you want, how to move forward and where to go from here. 

It's also for you if...

  • You are running around like a chicken with your head cut off, mostly keeping up appearances and making everything look good on the outside, despite desperately wanting to have more work-life balance. You get things done, but you want to be less reactionary and more intentional in every area of your life. Yet, there’s a part of you that’s worried if you take your eye off the ball even for a second, everything will fall apart. 

It's even for you if...

  • You are thriving, but want to continue to up-level, because you are truly committed to creating a life you are obsessed with. And you know, despite having already accomplished a great deal, this is just the beginning.

Other FAQs about the Retreat...

How much does it cost to attend The Obsessed Retreat?

The cost to attend The Obsessed Retreat is $4,000.

Are payment plans available?

Yes. You have the choice to pay in full or make two payments of $2,000. Your first payment will be due within 48 hours of submitting your registration form. Your second payment will be due by March 11, 2024.

What does that include?

Your admission to The Obsessed Retreat, including The Welcome Reception, three full days of workshops (with breakfast included), and The Farewell Dinner. It also includes LIFETIME ACCESS to monthly group coaching calls and the Member Portal, which will contain event recordings, call recordings, additional course content, written coaching support, and a community platform that you can use to stay connected with your peers.

The cost does not include travel expenses to Miami Beach, your lodging accommodations, or other incidentals during your stay.

Do I have to stay at The Betsy Hotel?

No. You are not required to stay at The Betsy Hotel.

However, if you are like me and you LOVE stunning hotels, like the convenience of staying at the retreat venue, and enjoy being able to spend quality time with the other retreat attendees who will also be staying on site, you'll want to stay there.

There is a VERY limited room block for retreat attendees.

The discounted group room rate is $515 per night.

When I say limited, I mean it.

Available rooms will run out.

Which means you want to register to attend The Obsessed Retreat as soon as possible.

Booking information for your lodging accommodations will be provided to you after you're registration for the event is complete and your first payment has been submitted. Do not complete your reservation separately.

How long do I have to register?

Enrollment for The Obsessed Retreat will close on February 23, 2024 at 11:59 PM.

Who can attend?

Anyone and everyone. Unlike some of my past events, this event is not limited to lawyers. If you aren't an attorney and you have been waiting to work with me, this is your chance.

Can you give more insight into the types of topics we'll cover when we workshop?

Yes, absolutely. There is no topic that's off limits. A signature part of my coaching style is that I cover all things personal and professional. I believe you can't separate one from the other. Your professional life impacts your personal life and vice versa. You can work through any problem you're facing during The Obsessed Retreat. But to give you a more specific idea of what that entails, we'll cover how to...

Set and achieve goals, stop procrastinating, master time management, stop people-pleasing, set and honor boundaries, dial down your perfectionism, improve your self-talk, increase your confidence, care less about other peoples' opinions, master the art of saying no, let go of the past, dismantle limiting beliefs, make empowered decisions, get organized, simplify your life, plan for your future, develop business, change jobs, reduce your guilt, worry, frustration and overwhelm, create more balance, be more present, and, ultimately, feel better.

What do I need to do to register for the event?

Click on any of the buttons that say "REGISTER HERE" and complete the form and press submit. Then keep an eye on your email. I'll send you an email welcoming you to The Obsessed Retreat community.

That email will include details about the retreat along with a link that will allow you to submit your first payment. Should you choose the two installment payment option, your second payment will be due March 1, 2024.

Once you submit your payment, you will receive the information to book your room at The Betsy Hotel should you choose to stay onsite.

Now, there's just one more thing you need to know about The Obsessed Retreat...

You want to be in this room.

This is the room where it happens.

Where transformation happens.

Where breakthrough happens.

Where inspiration happens.

Where community happens.

Where support happens.

Where bonding happens.

Where trust happens.

Where belonging happens.

Where thriving happens.

Where accomplishing the seemingly impossible HAPPENS.

You want to be in this room.

More importantly though...

You BELONG in this room.

The room where...

The growth will be unparalleled.
The support will be unparalleled.
The community will be unparalleled.

The room where...

Your RESULTS will be unparalleled.

The life you've been wanting to live is waiting for you.

Now, all you have to do is claim it.

Will you?

The Obsessed Retreat is an immersive coaching experience.

Three FULL days (18 hours total) of learning, growing and transforming.

No distractions.
No interruptions.
Just time to focus.

On solving problems.

On developing skills.

On making plans for your future.

On creating a life you're OBSESSED with.

If you've been under-living, it stops here.

As soon as you sign up to join me in Miami in March.

Will coaching help you get the results you want to achieve?


But don't take it from me.

Here's what my clients have to say about their experience.

“I became interested in coaching with Olivia for a couple reasons. I had concluded therapy a year prior and felt that I was ready to move from “surviving” to “thriving.” I wanted to take my life from feeling as though I was just getting by, to a life I was obsessed with. I was drawn to Olivia because her content was continuously helpful, energetic, and direct. I could feel her energy through the computer screen. I listened to and read her free content for a while and was able to apply it to my life in ways that helped. This is how I knew she was the real deal.”

My only hesitation was that I wasn’t sure how much something like this was supposed to cost. I now know that the price was a total steal. But at the time, I wasn’t sure. It helped to see other people commenting on the LinkedIn posts that the price point was very good, because I just didn’t have any experience with it. So it helped to see other people validating that the price was a great value.”

“I have had a great time in the Mastermind! The one thing I love most about working with Olivia is that she is completely non-judgmental. She accepts every client as they are, listens mindfully and asks purposeful questions, and then provides meaningful feedback that has no judgments attached. (Also, her advice is just stellar! It’s calm and kind and understanding that her clients are human.)”

“The skills you’re taught in the Mastermind will change how you see the world, how you approach and solve problems, and how you interact with others. It will help you take control of your emotions, your life, and your career. Six months is going to pass either way, you might as well learn new skills, feel better, and meet some great friends by the end of it.”

- Fatima -

“My downfalls were procrastination and self-doubt and [I] shame-spiraled when something went wrong on a case or at work. I was more dependent on superiors’ approval than I wanted to be. I was constantly concerned about my reputation and never felt like I was “good enough[.]”

“I wanted to shift my perspective, get better at managing my thoughts and time, and feel more confident. I was able to achieve all of these things through working with Olivia.”

“Olivia can coach the uncoachable. I came to her insecure, stressed out, and extremely skeptical of the coaching process[.]”

“The version of me who signed up with her would not have believed this, but she changed my life. If you are skeptical, if you doubt the process–that’s fine, but if you want real change in the way you think about yourself and manage your career, you need her. Full stop.”

“[Olivia is] the best at what [she does] and anyone who wants change in their lives should work with [her].”

- Marissa Cocchiolone -

“I was interested in working with Olivia because I was stuck. I was at a loss as to how to move forward in my career. I came to the realization that I had nothing to lose and everything to gain.”

Though coaching with Olivia, “I gained a greater understanding of myself. I learned the importance of mindset and I discovered that if I wanted to move forward professionally I needed to address some things personally.”

If you are considering working with Olivia, “Don’t hold back.”

- Lisa -

“Working with Olivia in my business taught me tools which helped me immeasurably in my life (marriage, relationships, parenting, business). This was a gift and one that I will always be grateful for.”

“I was interested in coaching with Olivia because I was looking for a resource during COVID to help me in my business and in consideration of a possible pivot. As a result of coaching, I got greater awareness in all areas of my life. I enjoyed having a judgment-free space in which to share & work through things. And I liked the continued, regular interaction and accountability.”

“I have zero regrets working with Olivia and my life has been transformed as a result of it.”

- Catherine Brukalo -

“I was interested in working with Olivia because I was in a cycle of procrastination and not getting things done. I also had high anxiety.”

“Though coaching with Olivia, I have learned what really drives behavior or inaction. I have someone to be my sounding board and mirror who is more interested in my improvement than making me feel better, and I have done a lot of growing while creating a framework to keep improving. Olivia is truly judgment-free. Working with her is worth every penny and moment of discomfort. As Olivia says, choose your discomfort. You can stay uncomfortable in your habits or you can manage the discomfort of change and improvement.”

- Kristin -

“I was interested in joining the Mastermind because I had never been in a coaching program with other lawyers which was refreshing. I had also attended one of Olivia’s webinars and loved how she integrated the self coaching model with typical problems that lawyers face.”

“The top three benefits about working with Olivia inside the Mastermind have been having a coach who understands a lawyer’s brain and how to reframe obstacles. Her willingness to be real and honest with us by sharing her own experiences. And having a dedicated time to work on managing my mind with a caring coach. Olivia holds space for whatever issue you are going through.”

“I didn’t have any hesitations about joining. I loved the Kick Off Event which helped me really explore my goals by taking a holistic view of my life and what I wanted to create in the next 6 months. The weekly coaching calls have also been great to course correct and make progress towards my goals. The Facebook Group has also been a great resource to get coached in between the weekly coaching sessions.”

“I’m looking forward to the next round of the Mastermind.”

- Estelle Winsett -

“Working with Olivia was one of the best decisions I ever made for myself. It has not only helped me change my life and the way I experience the world, but I have so much more to give and contribute to the world around me.”

“[I decided to invest in coaching because] I really just wanted to feel better. Less anxious, less overwhelmed and more confident. All of those things happened and more.”

“I started to figure out what I actually wanted in my career (something I’d never done before – I’d always just done what I thought I was supposed to do).”

“And from that place of understanding, I learned how to make decisions that moved me toward that career and how to allow the discomfort of implementing both big and small changes to create a practice that aligned with what I wanted. That required me to address my people pleasing and my perfectionism and to really understand how those were showing up in my life and to learn how not to let them guide my decision-making.”

- Jenn Deal -

“I was interested in coaching with Olivia because I was very much struggling with mental health; therapy did not work. I needed to find someone who could help me realize how to manage lawyer life and personal life.”

“Working with Olivia changed my life and the way I think about my job and my feelings. It made me a better coworker and attorney by teaching me that there are certain things I cannot control and to let those things go. It taught me how to push through the stagnant points in my life and career and how to get through (and get started on) the things I REALLY hate doing.”

“Price was a huge hesitation.” But that didn’t hold Michelle back. She moved forward and made this commitment to herself. And she is so glad she did. “Olivia changed my life. You can’t put a price on an impact like that!”

If you are considering working with Olivia, “IT IS WORTH IT! You are worth it. Your life will change for the better!”

- Michelle -

“I was interested in coaching with Olivia because I was tired of feeling overwhelmed; I felt guilty about a lot of things related to my work/life. And I wanted to change that.  And believe it or not, I lacked confidence. I also needed direction in ALL aspects for my solo practice.”

“I don’t think I had any hesitations when it came to working with her. I am a professional researcher and I researched the sh*t out of her before consulting with her. After consulting with Olivia, the only question I had was ‘where do I sign?'”

“As a result of working with Olivia, my thoughts when approaching all situations (whether career or personal life) have changed, and therefore the outcomes have changed. I am doing more of the things I want to do in all aspects of my life (enough with the people pleasing), and I feel less guilty and have stopped punishing myself for it. I am learning to love my life/career in a different way because I see things differently now. And I have much less anxiety.”
If you are thinking about making this investment, “Don’t nickel and dime your mental health. Olivia provides life-changing lessons for your mind. You will never go back to thinking/being the same individual (in a good way). Pay the money and get to working on yourself because you deserve it.”
“If people are open-minded, willing to change, and really consider (put into work) the questions and lessons Olivia provides, then their lives will change immediately.”

- Gerri Marshall -