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Are you ready to live a life with less stress and FAR MORE fulfillment?

If you are, it starts here.

With The Less Stressed Lawyer Mastermind.

The six-month group coaching program that will teach you the fundamentals to managing your mind so you can manage your life.

Without all of the stress, guilt, overwhelm and hustle.

Specifically, in the Mastermind, you'll learn 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

These are the essential skills you need to develop to thrive personally and professionally.

And, let's be honest...

You didn't learn them in law school or in any of the jobs you've had since.

So it makes sense that you're struggling.

It's hard to be good at something you've never been taught.

But that's what the Mastermind is for.

It's your one-stop shop for learning everything you need to know to go from living a life you merely tolerate to a life you truly love.

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...

You don't need a new planner.

You need a new plan.

One where you make yourself and your wellbeing your top priority.

Because, you can't hustle your way to happiness.

(Believe me, I tried.)

You have to cultivate it.

By designing your life intentionally.

And then reverse engineering that design.

To create a roadmap you can follow to achieve your desired results.

That's exactly what you'll learn to do in The Less Stressed Lawyer Mastermind.

You'll master living an intentional life.

A life you're truly obsessed with.

How do you know if the Mastermind is right for you?

The Mastermind is a perfect fit for you if...

  • You are paralyzed by the stress you experience and are struggling to wade through your workload while you navigate your perfectionism, your habit of procrastinating and your people-pleasing tendencies. 

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 and be less reactionary and much more intentional in every area of your life. But you’re worried that 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.

Here is what you get when you join the Mastermind.

A 3.5-Day In-Person LIVE Event

The Mastermind will commence with TLSL Mastermind LIVE Event, a 3.5-day, in-person immersive retreat designed to accelerate your personal development and foster your growth.

The August 2023 LIVE Event will be held in Big Sky, Montana at Montage Big Sky, a luxury, five-star resort in one of the most beautiful cities the United States has to offer.

The LIVE Event festivities will commence on the evening of August 23, 2023 with TLSL Mastermind Welcome Reception, followed by three full days of training, live coaching, workshopping, and masterminding, and will conclude on August 26, 2023 with TLSL Mastermind Farewell Dinner.

The dates for TLSL Mastermind LIVE Event are:

8.23.23: TLSL Mastermind Welcome Reception

8.24.23: TLSL Mastermind LIVE Event Day One (All Day Training)

8.25.23: TLSL Mastermind LIVE Event Day Two (All Day Training)

8.26.23: TLSL Mastermind LIVE Event Day Three (All Day Training) followed by TLSL Mastermind Farewell Dinner

Six months of weekly group coaching calls

Following the Mastermind LIVE Event, each week we will mastermind together for one hour with structured calls that mix core teachings to support your growth and coaching that will help you gain the requisite awareness you need to make the changes you want to make and move you towards your goals.

Group coaching calls will be on Tuesdays at 2 PM ET following the Mastermind LIVE Event. Attendance to the group coaching calls is expected, but Mastermind members will have access to all call recordings to reference at later times.

The Less Stressed Lawyer Mastermind Facebook Group

You will also have access to The Less Stressed Lawyer Mastermind Facebook Group where you can get coaching from me in between our weekly calls as well as support from your peers in the Mastermind.

Have a question? Bring it to the group.

Have an issue you need coaching on? Bring it to the group.

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

There will be no shortage of the community you've been craving once you join the Mastermind.

The Less Stressed Lawyer Mastermind Member Portal

Mastermind members will get access to the Member Portal, which will contain group coaching call recordings, Mastermind workbooks, and a vault of dozens of hours of additional video training resources that will allow Mastermind members to accelerate their growth at their own pace should they wish to dive deeper into the concepts taught in the Mastermind between the weekly calls.

Here's a SNEAK PEEK of the LIVE Event.

Play Video

Other FAQs about the Mastermind...

How much does it cost to join The Less Stressed Lawyer Mastermind?

The cost to join the Mastermind is $5,000.

You have the choice to pay in full or make two payments of $2,500. If you are accepted into the Mastermind, your first payment will be due within 48 hours of your acceptance.

NOTE: The cost to enroll in the Mastermind does not include travel expenses to and from the LIVE Event or lodging accommodations and other incidentals during your stay. If you are attending the LIVE Event in person, it is required that you stay at Montage Big Sky where the LIVE Event is being held.

Booking information for your lodging accommodations, including the link you will use to reserve your room at the discounted group rate, will be provided to you after you are accepted into the Mastermind. Make sure you utilize that link when it is made available to you. Do not complete your reservation separately.

Our discounted group rate is $599 per night (originally $1,500 per night). By joining the August 2023 cohort of The Less Stressed Lawyer Mastermind, you get the opportunity to experience five-star luxury at one of the country's most beautiful hotels at a once-in-a-lifetime price point.

What day and time are the weekly calls?

The weekly group coaching calls are held via Zoom and take place on Tuesdays at 2 PM ET.

How long do I have to apply?

Enrollment for the August 2023 class will close on July 21, 2023 at 11:59 PM or when the limited spots are filled, whichever occurs first.

Now, there's just one more thing you need to know about the Mastermind...

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?

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 -

Litigation Partner

“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 -

Federal Government Attorney

“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 -

Vice President & General Counsel

“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 -

Attorney | Law Firm Owner | Coach

“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 -

Law Firm Partner

“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 -

Attorney & Director of

Professional Development

“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 -

BigLaw Partner

“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 -

Counsel, Private Practice

“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 -

Immigration Attorney &

Solo Practitioner