Not just your job performance.
Not just your investment portfolio.
Not just your business goals.
Your life.
Most people spend more time planning their next vacation, their holiday dinner menu, or their kid's birthday party than they spend planning their lives.
Which means they spend years living on autopilot.
And then they wonder why they feel stuck.
Which is why…
At The Obsessed Retreat, we'll evaluate the essential components of an obsessed life.
We'll uncover the habits, beliefs, behaviors, and decisions that are holding you back.
Everything that’s standing between you and the life you want to live.
And together, we'll identify what’s working, solve what isn’t, develop the skills you need to move forward, and leave with clear decisions, concrete goals, and a plan you'll actually implement to create a life so good you wouldn't dare trade places with anyone else.
→ An incredible career, but you struggle with boundaries.
→ Financial success, but no time for fun.
→ Total confidence at work, but chasing validation everywhere else.
→ A beautiful family, but a calendar too packed to enjoy them.
→ Knowing exactly what you want, but lacking the discipline to chase it.
→ Wildly productive, but miserable because your relationships are hurting.
Everything starts here. Your thoughts shape your emotions, your actions, and your results. If you can't manage your mind, you'll spend your life reacting instead of intentionally creating, all while experiencing unnecessary stress, suffering, and self-imposed obstacles. If you want different results, you have to learn how to think differently.
How you spend your time determines how you spend your life. You don't need more of it. You need to use the time you have more intentionally. If you don't, you'll constantly feel behind, create unnecessary overwhelm, accomplish less than you're capable of, and regret not making time for the people and priorities that matter most.
If you can't set boundaries, you'll spend your life people pleasing and abandoning yourself to keep everyone else happy. That eventually turns into resentment because you've built your life around everyone else's priorities instead of your own. You can't create the life you want while abandoning what's important to you. It's your job to protect yourself.
Perfectionism keeps you stuck. It causes you to overthink, procrastinate, and delay taking action. If you want to accomplish more, achieve bigger goals, and feel better about yourself, you have to overcome it.
The relationship you have with yourself affects every area of your life. Confidence changes the way you think, the decisions you make, and the opportunities you're willing to pursue—and ultimately, the life you create. If you want a better life, you have to believe you're capable of creating it.
The quality of your life is determined by the decisions you're willing to make. If you're constantly spinning, overthinking, worrying, and waiting until you're sure, you'll stay exactly where you are. If you can't make decisions, you can't make progress. It's that simple.
It's impossible to create the life you want if you're constantly worried about what everyone else will think. If you only feel good about yourself when other people approve of you, you'll let their opinions determine your decisions and, ultimately, your life. You have to be willing to disappoint other people to stop disappointing yourself.
Discipline is one of the most important skills you'll ever develop. It's the ability to do what you said you were going to do, even when you don't feel like it. The life you want will require uncomfortable action. Discipline is what allows you to take it. Everyone wants the results. Very few people are willing to consistently do what's required to create them. Discipline is what separates the two.
Every meaningful goal will require you to feel uncomfortable. There is no way around it. Whether it's having a difficult conversation, saying no, going to the gym, sticking to a budget, or putting yourself out there, discomfort is part of the process. Your willingness to feel uncomfortable will determine the quality of the life you create.
You spend too much of your life working to settle for "it's fine." Are you doing what you actually want to be doing? Are you proud of what you've built? Do you want more? Is there a problem we need to solve? Whether you're looking for more fulfillment, more success, or a completely different direction, we'll identify the obstacles standing in your way and the skills, support, and solutions required to move forward.
Money isn't everything, but it influences almost every aspect of your life. Many of the things people picture when they imagine their obsessed life—taking the trip, buying the house, retiring early, starting a business, or helping the people they love—cost money. If your financial house isn't in order, it becomes much harder to intentionally create the life you want.
You can't get through the human experience without dealing with people. The quality of your relationships determines the quality of your life. The more conflict you have with your family, romantic partner, friends, or colleagues, the more you suffer. Learning to communicate clearly, resolve conflict effectively, and navigate relationships well isn't optional. It's essential to creating your obsessed life.
The life you're creating is only as enjoyable as your ability to experience it. Your health influences how you feel today, how you'll feel tomorrow, and how long you'll get to enjoy the life you're working so hard to create. It affects your energy, your confidence, and your longevity. That's why it deserves your attention.
You spend too much of your life in your home and office to settle for environments you don't enjoy. Whether your space is cluttered, disorganized, outdated, or simply no longer feels like you, your physical environment should be in alignment with the life you're creating. If it isn't, it's worth asking what needs to change. Whether that means decluttering, renovating, moving, or making a bigger change altogether, your surroundings deserve your attention.
Organization isn't about perfection. It's about creating systems that reduce unnecessary friction and help your life run more smoothly. Whether it's your calendar, your paperwork, your travel, your routines, or your home, getting organized gives you more time and energy for what matters most.
Life isn't meant to be endured. It's meant to be enjoyed. Too many people postpone fun until they have more time, more money, or fewer responsibilities. If you're constantly waiting for "someday" to take the trip, try the hobby, or make time for the things you love, it's time to figure out why. Maybe you need to give yourself permission. Maybe you need to carve out the time. Or maybe you've forgotten what actually brings you joy. Whatever the reason, we'll address it. Because fun deserves to be part of your life, not something you keep putting off.
For years, the retreat ran in three separate parts:
—one day to solve the problems keeping you stuck,
—one day to develop the skills you needed to move forward, and
—one day to set goals and make plans to achieve them.
When it came to solving problems, we focused on the major areas of your life—career, finances, health, relationships, and a few more.
That approach worked. But after coaching hundreds of people through it, I saw how it could work better.
Those categories were broad. We'd pinpoint the general area where you felt stuck, but not the specific issue keeping you there—and when the assessment is that broad, the more precise problems slip through.
Because the biggest obstacles standing between people and the lives they wanted were rarely broad. They were specific: perfectionism, poor boundaries, indecision, people-pleasing, weak discipline, discomfort avoidance. Nameable skills and patterns—and because we weren't assessing them directly, they went unaddressed. So they persisted.
Two other things became clear. One day was never enough to work through your problems. And keeping skill-building on its own day meant you learned the skills over here and tried to apply them over there.
For each one, you're either satisfied with where it stands or you need to make changes to close the gap. Nothing gets lumped together. Nothing slips through.
We give problem-solving the time it deserves.
And instead of teaching the skills separately, we build them in right where you need them, while we work through your real challenges.
We're still solving problems.
We're still developing skills.
We're still setting goals and making concrete plans.
We're just doing it with far more precision—because the more specifically we identify what's getting in your way, the faster and more effectively we can solve it.
instead of several broad categories, we assess the Essential Components of an Obsessed Life—a scorecard for every area and skill that determines whether you can create the life you want.
Whatever your answers are... That's what we'll work on in Savannah.
We'll identify exactly what's getting in your way.
We'll solve the problems keeping you stuck.
We'll develop the skills you're missing.
We'll make the decisions you've been avoiding.
We'll create a plan you'll actually implement when you get home.
Which ones need your attention?
By the end of the retreat, you won't just leave with pages of notes you'll never look at again.
You'll leave with:
Whether it's your career, your relationships, your finances, your confidence, or something else, the problems that brought you to Savannah won’t be coming home with you.
Absolute clarity about what success looks like for you over the next year.
A personalized 12-month implementation strategy that bridges the gap between knowing what you want and actually creating it.
The retreat lasts four days.
The relationships last for years.
A comprehensive evaluation of every essential component of your life, showing you exactly what deserves your time, energy, and attention.
These aren't hypotheticals.
They're receipts.
Everything below is something a real retreater actually created after doing this work—wins they've celebrated in our community, and results I've watched unfold firsthand.
Open any component and see what's possible for you.
WHAT THEY'RE SAYING
WHAT THEY'RE SAYING
Southern charm meets modern luxury in the heart of Savannah's Historic District.
As a retreat attendee, you'll receive access to a special group rate at The Perry Lane Hotel—just $359 per night—making it easy to stay with the group and fully immerse yourself in the retreat experience.
IN SAVANNAH, GEORGIA. THE PERRY LANE HOTEL TO BE EXACT.
For four days, you'll trade your overflowing inbox, endless responsibilities, and constant distractions for meaningful connection, practical coaching, unforgettable experiences, and the unmistakable charm of a city that invites you to slow down long enough to finally hear yourself think.
You'll have the time to reflect.
The clarity to make decisions.
And the chance to step away from your life long enough to intentionally decide how you want to live it.
detailed event schedule
SUNDAY | OCTOBER 11TH
6 PM - 9 PM | THE WELCOME RECEPTION
MONDAY | OCTOBER 12TH
9 AM - 10 AM | BREAKFAST
10 AM - 1 PM | WORKSHOP DAY ONE - MORNING SESSION
1 PM - 3 PM | LUNCH BREAK
3 PM - 6 PM | WORKSHOP DAY ONE - AFTERNOON SESSION
TUESDAY | OCTOBER 13TH
9 AM - 10 AM | BREAKFAST
10 AM - 1 PM | WORKSHOP DAY TWO - MORNING SESSION
1 PM - 3 PM | LUNCH BREAK
3 PM - 6 PM | WORKSHOP DAY TWO - AFTERNOON SESSION
WEDNESDAY | OCTOBER 14TH
9 AM - 10 AM | BREAKFAST
10 AM - 1 PM | WORKSHOP DAY THREE - MORNING SESSION
1 PM - 3 PM | LUNCH BREAK
3 PM - 6 PM | WORKSHOP DAY THREE - AFTERNOON SESSION
7 PM - 10 PM | THE FAREWELL DINNER
YOU’LL WANT TO ARRIVE NO LATER THAN THE AFTERNOON OF OCTOBER 11TH AND DEPART NO SOONER THAN THE MORNING OF OCTOBER 15TH.
Most people already know they want more.
More fulfillment.
More confidence.
More freedom.
The hard part isn't wanting more.
It's figuring out why you don't already have it.
That’s where I come in.
My job isn't to motivate you.
I’m not here to hand you another inspirational quote or tell you to "believe in yourself."
I'm here to help you identify what's standing in your way, determine what needs to change, and teach you exactly how to change it.
It's about making the right changes, in the right order, over time.
That requires two things.
You have to think differently.
But you have to operate differently too.
That's why every aspect of my coaching is designed to help you do both.
No fluff. No theory.
Just brass-tacks coaching that creates real results.
I've spent years doing this work in my own life and helping hundreds of ambitious professionals do the same.
→ Three immersive workshop days with more than 18 hours of coaching, strategy, and problem solving.
→ Coaching 101, my self-paced mindset course that equips you with the fundamental coaching concepts and tools we'll build on throughout the retreat, so you arrive prepared to get the most out of the experience.
→ An intentionally small group to maximize personalized coaching and individual feedback.
→ Welcome reception, daily breakfasts, and a farewell dinner designed to deepen connection throughout the retreat.
→ Private community access before and after the retreat to build relationships, maintain momentum, and support your continued growth.
→ Retreat recordings so you can revisit the lessons, strategies, and breakthroughs long after you return home.
WHAT THEY'RE SAYING
WHAT THEY'RE SAYING
The cost to attend The Obsessed Retreat is $5,000.
Yes. Payments will be made in two installments. You can complete your first payment by clicking on any of the “Register Here” buttons on this page. Once you submit your first payment, you will receive a confirmation email with information about the upcoming event. Your second payment will be due by September 15, 2026. Once you submit your first payment, you will also receive limited access to The Obsessed Membership Member Portal. Inside the Member Portal you’ll be able to meet and engage with the other Retreaters, watch on-demand foundational videos to prepare you for the live workshop sessions and access the retreat recordings once our time in Savannah concludes.
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 limited access to The Obsessed Membership Portal, which allows you to connect with your peers, watch pre-retreat module videos that will teach you the foundational concepts we’ll be using at the Retreat, and access the retreat recordings once our time in Savannah concludes.
The cost does not include travel expenses to Savannah, your lodging accommodations, or other incidentals during your stay.
You can have it. To unlock full access to The Obsessed Membership Portal all you need to do is enroll in The Obsessed Membership here. When you enroll, you will get complete access to the monthly group coaching calls, unlimited written coaching and feedback, all of the Obsessed Membership course content including Time Management Mastery and The Business Development Blueprint, the Masterclass Vault with over 50+ on-demand trainings, and the ability to purchase 1:1 coaching sessions for extra support.
No. You are not required to stay at The Perry Lane 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 $359 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 your registration for the event is complete and your first payment has been submitted. Do not complete your reservation separately.
Enrollment for The Obsessed Retreat will close on August 12th, 2026 at 11:59 PM.
Anyone and everyone interested in creating a life they’re obsessed with. Unlike some of my past events, this event is not limited to lawyers.
Yes. One of the biggest changes I made this year was redesigning the curriculum around the problems people struggle with most.
Instead of evaluating broad areas of your life, we'll work through the specific topics that tend to keep people stuck, including time management, boundary setting, perfectionism, confidence, people-pleasing, external validation, discipline, decision-making, organization, relationships, career and business growth, finances, health, mindset, and more.
There isn't a personal or professional problem that's off limits. Whether you're trying to navigate a difficult relationship, prepare for a promotion, grow your business, stop procrastinating, set better boundaries, become more organized, make a major life decision, or simply figure out what's next, we'll use the coaching and problem-solving process to create a plan that fits your specific situation.
Click on any of the buttons that say “REGISTER HERE” and complete the payment form. Then keep an eye on your email. I’ll send you an email welcoming you to The Obsessed Retreat community.
Once you submit your payment, you will receive the information to book your room at The Perry Lane Hotel should you choose to stay onsite.
Most entrepreneurs don't have a business problem. They have a dozen interconnected problems that are affecting their business.
They're procrastinating on marketing because they're afraid of rejection. They're overthinking every decision because they want to get it "right." They're saying yes to the wrong clients because they need the money. They're working nights and weekends but still feel behind because they don't have a system for managing their time. They're comparing themselves to everyone else online and wondering if they should just give up.
At The Obsessed Retreat, we'll address all of it.
Throughout the retreat, we'll workshop the challenges you're facing while developing the skills that will help you solve them—not just this month, but for years to come.
We'll cover topics like mindset, confidence, perfectionism, discipline, decision-making, boundary setting, time management, organization, career and business growth, finances, and more. Then we'll apply those concepts directly to your business and your life.
Whether you're struggling to sign clients, create consistent revenue, market your business, manage your time, build confidence, navigate difficult decisions, or figure out your next move, you'll leave with practical solutions and a clear plan for moving forward.
The goal isn't to give you another notebook full of ideas. It's to help you remove the obstacles keeping your business stuck so you can get back to building the business—and the life—you set out to create.
If you're constantly overwhelmed, behind, and wondering why everyone else seems to have it together, this retreat was designed for you.
Maybe your inbox is out of control. You procrastinate until deadlines become emergencies. You overcommit, underestimate how long everything will take, and constantly feel like you're disappointing people. You leave work exhausted, only to spend the evening mindlessly scrolling your phone because you're too drained to do anything else.
You keep telling yourself you'll get caught up next week. But next week never comes.
At The Obsessed Retreat, we'll identify exactly what's keeping you stuck and help you build the skills to finally break the cycle.
Throughout the retreat, we'll cover topics like mindset, time management, perfectionism, confidence, discipline, decision-making, organization, boundary setting, relationships, finances, health, and more. Then we'll apply those concepts directly to the challenges you're facing.
Maybe your biggest obstacle is procrastination. Maybe it's people-pleasing. Maybe you're saying yes to everything, struggling to prioritize, or constantly looking for reassurance before making decisions. Whatever the problem is, we'll work through it together and create a practical plan you can implement when you get home.
The goal isn't simply to help you become more productive. It's to help you become someone who consistently follows through, manages their time intentionally, makes decisions with confidence, sets healthier boundaries, and finally feels in control of their life again.
If you're tired of feeling overwhelmed, exhausted, and like you're always one step behind, this retreat will give you the tools, coaching, and plan to change that.
Maybe you're successful.
You have the career you worked hard for. You're financially stable. You've built a good life. From the outside, everything looks exactly the way you hoped it would.
So why does something still feel...off?
You're checking the boxes but not feeling excited anymore. You're busy, but not fulfilled. You keep telling yourself you should be happier than you are.
Maybe you've spent so many years chasing the next promotion, raising kids, building your business, or taking care of everyone else that you've stopped asking yourself what you actually want.
Or maybe you know exactly what you want—you just haven't made it a priority.
The truth is, success and fulfillment aren't the same thing.
The Obsessed Retreat isn't just for people whose lives are falling apart. It's for people who know they're capable of more and don't want to wake up five years from now wondering where the time went.
Throughout the retreat, we'll evaluate the essential components of an obsessed life and identify what's preventing you from enjoying the one you've already built. We'll workshop your biggest challenges, strengthen the skills that matter most—from confidence and boundary setting to decision-making, discipline, relationships, finances, health, and more—and create a clear plan for what's next.
Sometimes the biggest breakthroughs don't come from fixing what's broken.
They come from intentionally improving what's already good.
If you've ever caught yourself thinking, "There has to be more than this," this retreat is your opportunity to figure out what that "more" looks like—and start creating it.