The Level Up Retreat

Villa Coco Mar 1

Are you ready for the next level in your career, leadership, or business?

Want to make sure you get there in a way that is sustainable and in alignment for you and the life you want to live?

Yeah, we thought so. 😊

The Level Up Retreat is designed to accelerate your journey. Tailored for executives, entrepreneurs, and high-achievers, the experience guides you to articulate the game you're meant to play and assemble the pieces to shift into playing that game day-to-day.

What Does It Mean to Level Up?

So, what does “next level” and “level up” mean?

It might be a silly question, but we think it’s one we need to address upfront.

What we mean when we say next level or level up is the complete opposite of hustle culture and toxic work environments.

Here’s what leveling up has looked like for past participants (and it can look similar or completely different for you):

🗺️ Setting course on a brand new career path.

😎 Learning that with x & y in place, you can retire many years earlier than you had thought possible.

🙌🏼 Increasing your reach in your current market or a new one in fun and meaningful ways.

👪 Finding a better balance of work and health and family that still provides well for you.

🫱🏽‍🫲🏼 Setting up your business for succession.

💸 Finding better team alignment that leads to more profit with fewer work hours needed.

😊 Better utilizing the support team that you have so that you have more time to spend on your 10x work.

✅ And, the list goes on….

Think of yourself in a place where work and career, family, health, and other important areas of your life are balanced in a way that gives you a holistic, thriving life, all in a sustainable way. That’s what it means (to us) to Level Up.

You've Taken Care of Everyone Else. Now It's Your Turn.

As the world continues to evolve, so do the challenges and opportunities we face in work and as individuals.

Over the last 3+ years (with the pandemic and lockdowns and massive societal changes) you probably wore new hats and took on responsibilities that were not previously yours. Not to mention, the heavy emotional load to support loved ones, teammates, employees, friends, and others.

Maybe you had to school your kids? Perhaps you had to do the work that you would normally do with a team of 10 with a team of 3? Maybe you had to work 50 hours a week rather than 35? Perhaps your health routine took a backseat to survival? Perhaps you lost sight of what you want and need?

In short, you took care of your people (and company) and carried or supported them through the storm.

With making sure that your people and company were taken care of, though, have you had the opportunity to

⏸️   pause long enough to look up and get your bearings,

✅   re-center and get clear on your current priorities, and

🗺️   re-chart the path forward for you and your company

So many executives and professionals are exhausted, burned out, demotivated, and just getting through the day-to-day.

You're meant for more than surviving the day.

Join us for our next retreat to

☀️  get clear on and align your priorities with your dreams, legacy, and best work

📍  map an actionable plan for yourself to make your vision a reality, helping you make a greater impact

🫱🏽‍🫲🏼  connect with, soundboard, strategize, and adventure with (up to) 12 other conscious executives, leaders, founders, creators, and seasoned professionals who are likely friends you just haven't met yet

all while your well-being is centered and you don't have to make decisions about things like food, transportation, and such.

Get yourself to the venue and we handle everything else. 


Kendra Wright

Founder, Rebel Media

If you're looking to level up your business, life, and leadership - Charlie and Angela are a killer combo who can take you where you want to go. At the Level Up retreat I learned practical strategies to immediately leverage my team and empower them to move forward without constant communication from me. I now have the skill set to be a more thoughtful and intentional leader, which is life-changing for my team and clients, not just me.

The unique structure of the retreat also left me feeling restored, even after working on my business, which has never happened at an event like this. I now have new ways to grow my revenue and work with clients that I did not offer before. I've leaned into my strengths, became more aware of my blind spots, and learned how to ask for help more often instead of trying to be a hero.

What You'll Get From Your Stay With Us

You've probably found yourself saying some variant of "if you want different results, you have to do something different." While that's true, it can be challenging for professionals to see what to do differently with already overfull schedules and responsibility overload.

As Charlie says, "it's hard to read the label when you're stuck inside the jar."

The Level Up Retreat is your chance to get recharged, re-centered, and clear about your roadmap for work and life. You'll be connected with other professionals who get you and can support, challenge, and inspire you to stay on your path.

And by stepping away from the noise and whirlwind of the daily grind, you'll be able to tap into the parts of yourself that are too buried to be seen or heard sometimes.

But you might be curious about how all of that will translate into real change once you're back at work and home. Your retreat experience will help you lead and create

💰  more revenue, faster, as you are able to focus on your genius with confidence and clarity

💪🏽  better team alignment, leading to more of the right work happening with less effort and less cost

🏅  better talent cultivation and retention of high performers

🔎  focus to extend your reach and impact beyond the success you've already achieved

😌  less burnout and more peace and presence at home as you are better able to leave work at work

What would a 10% shift in any of the above mean for you and your organization? Likely many multiples of the cost of the retreat.

You Won't Be The Only

Here's the thing: when you're already a successful professional, executive, or founder it can be really hard to find advisors, communities, and events to go to that are relevant to your acumen or level of success.

So often we get stuck, figuring it out on our own or bumping up against plateaus and upper limits for years.

We're well off enough that it's okay in the grand scheme of things, but, let's be honest, grinding while watching others take off gets old. Especially when they take off on the very thing you've been doing.

I get it because so many of our clients start there with us and we've been there.

If you are already familiar with us, you've probably experienced the diverse and high-caliber set of leaders, change-makers, and founders that run with us. You won't have to worry about being the smartest or most successful person in the room, and, even if you are, we have a knack for working with people who are.

Incredibly smart, principled, caring, and successful people are our jam and, at this point, a given for us.

What's different about our folks is the paths they've chosen in their lives. Some run large organizations. Some run intentionally small teams. Some write great books; others build large platforms. All excel at what they do.

Like you do. 

Jacquette Timmons

Jacquette M. Timmons

Founder, Business & Financial Coach and Speaker

I knew I was going to get a lot from this experience but it was more than I could have expected. Angela and Charlie do deep work with their community; I knew that going in to this retreat, but I had no idea how deep we would go and how transformative it would be.

The experiential design of this retreat was phenomenal. It's amazing how much good work you can get done when you're also given the space to process it and not feel rushed. I have more clarity on the value I bring to the table and how to communicate that value to potential clients. This is the business retreat that I didn't know I needed. The impact this will have on my business and personal life is immeasurable.

justine clay

Justine Clay

Business Coach

The moment a friend shared the Level Up retreat with me, I knew I had to make it happen.  It was a full mind, body, and soul 'yes.' I expected high-level business support and I definitely got all that and a lot more. What I hadn’t anticipated was how deep the work would go on a full-human level. Charlie and Angela are master facilitators and space holders for ALL the things that come up in the life and business of an entrepreneur.

I left with the business insights and strategies I expected, but also a whole lot of clarity about and compassion for myself that I hadn’t bargained for, but absolutely needed. If you’re a purpose-driven entrepreneur who is looking to make huge changes in your business and life, this retreat will blow your mind. Trust the process and let the insights and a-ha’s flow in.

Retreat Flow and Schedule

We will be gathering for a week (Saturday arrival - Friday departure) to center you, make a real plan to implement change in your organization and life, and roadmap a doable plan to get you there. And, if you work in a team, you will have the opportunity to focus on how they will be part of this plan.

The first half of the retreat will focus on you and the second half will focus on your world. Both need to be in alignment and you already know it needs to start with you.

We have very intentionally made this retreat longer than many retreats you may have seen before, so that we can go as deep as we need to go.

As well, we have intentionally chosen to keep attendance to a maximum of 13, so if you join us you know you will have focused time for you and the support you need.

We know how frustrating it is to invest time, money, and energy into a retreat and not actually get what you needed - that's not going to happen with us.

You'll have time and space to:

😌  take this slowly

🚶🏾  integrate at a human pace

💆🏽‍♀️  actually have your own self care and needs centered

📄  roll up your sleeves with us and co-create documents and assets to take the great work you have done and make sure it is actioned when you return home and to work

How long have you been dreaming of having a chance to step away and reset? How about a few focused days to get some of those high value projects done? And what could you do if you did that with fellow professionals and leaders in a container designed precisely for it?

You will see that we have designed the flow of the week in a way that gives you plenty of free time and space (if you want it), lots of time with Charlie and Angela to go deep on the work, and space to collaborate and work outside of scheduled sessions, also.

👇🏽👇🏽👇🏽(Click the 'Tentative Schedule' expander below to see our schedule)👇🏽👇🏽👇🏽

Saturday afternoon/evening arrival - Day 1

  • Settle into your private room and space
  • Get to know the other participants if you desire
  • Welcome Dinner
  • Opening, Roadmapping, and Intention Setting

Sunday - Day 2

  • This is a day of rest, rejuvenation, connection, solo time, or adventure (choose your own adventure)
  • Today we are specifically focused on ensuring each participant is fully settled in and getting all of their needs met to fuel and prepare for a life-changing week ahead
  • After you register, Angela and our personal concierge will make sure that Sunday meets your needs. This could include:
    • a massage from our in-house masseuse
    • a quiet space set aside just for you to do some initial pre-work, brainstorming, and sinking into what you need and want
    • visit Cabarete, just a few short miles from the villa for kite surfing in one of the world's most popular beaches for this activity
    • a relaxing day by our private pool or sunny or shaded areas by the beach
    • so much more or nothing at all – again, this is all about centering you and your needs

Monday - Day 3

  • Sessions with Charlie and Angela Focused on You
    • Three Dreams - What you dream for your life, biz, and/or career in the next three years.
    • Your Personal Nav Bar - We work backward to fill in the gaps of where you want to be in the next decade.
    • Balancing the Different Selves and Energies - Understanding the different aspects of yourself and how they show up in your life and work.

Tuesday - Day 4

  • Sessions with Charlie and Angela Focused on You
    • Deeper Self Knowing - Understanding the different aspects of yourself and how they show up in your life and work.
    • Your 10 Dimensions - Now that you know about your different selves and energies, we can address the 10 Dimensions that lead to a flourishing, full life. We’ll help you identify where and how you can get the balance you need.

Wednesday - Day 5 

  • Sessions with Charlie and Angela Focused on Your World
    • Prioritizing Joy and Environment Design- You’ve identified your dreams, where you want to head, what selves need support, and your 10 dimensions - it’s time to optimize a better way to get you where you’re wanting to go. This is much more than your typical environment design exercise.
    • Your 10X Work - We will be focusing on what makes you uniquely you and the most high value work you can be doing in your company or business. What is that 10x work that only you can do?
    • Dropping 10 Hours/Week – Of all the challenging things we will do this week, this could be the most challenging for some. We are going to help you identify work that needs to be taken off your plate for any number of reasons.
    • A Guide to Working With You – It’s time to give your team the cheat code/handbook to working with you. We will help you create your very own Guide. Trust us, this exercise will make your life and your team’s life and output so much better. There's a version of this that works well for those who generally work solo, as well.

Thursday - Day 6

  • Sessions with Charlie and Angela Focused on Your World
    • Planning and Roadmapping - Let’s get your plan captured and articulated in a way that you (and your team if you have one) can follow and action as soon as you are back to work. We'll make sure you have a doable plan. 

Friday - Day 7

  • Final Session with Charlie and Angela
    • Tying It All Together and Intentional Closing
  • Friday early afternoon departure

Meet Charlie & Angela, your hosts and founders of Productive Flourishing

Charlie Gilkey. I am the lead consultant, coach, and strategist at Productive Flourishing. I have nearly 20 years of fieldwork that incorporates systems thinking, strategy execution, leadership and organizational development, practical innovation, and communication.

Besides the technical expertise, I possess a passionate drive to help leaders and owners achieve more than they could have ever imagined. My experience includes leading 200+ soldiers in the U.S. Army, 15 years consulting leaders in various industries in for-profit and nonprofit industries, from Fortune 100 companies to tiny nonprofits, writing award-winning books, and serving on various boards. My most recent book, Team Habits, is a guide to creating practices in teams that create great results and belonging.

Angela Wheeler, PhD. I am the co-founder and chief community builder at Productive Flourishing. With a passion for facilitation and an unparalleled ability to get to the heart of what drives leaders and change makers, I consider it an honor to hold space for and be a mirror for others to do their best work.

I have more than 20 years of experience teaching, coaching, facilitating, and leading in different sectors, including in academia, for-profit and non-profit industries, and spiritual communities. With my broad knowledge and experience, and a unique lens of rooted leadership that focuses on strengths and development, not deficiencies, I help leaders create dynamic, authentic, trustworthy, and high-growth environments.

Frequently Asked Questions

If you are a founder, leader, or executive and know deep down that you need space to breathe, dream, take care of yourself, and be with people who "get you," and the idea of a retreat in the sunny, warm Dominican Republic, being taken care of for a week, and centering your needs and desires is resonant, all while ensuring the next chapter is fulfilling you and leveling up how you show up personally and're a fit. 

If you're still not sure, no worries. Just fill out this short form and Angela will be in touch to answer any questions you still have. 

Welcome! We are honored you are here. We are big-hearted founders and leaders who believe that we can make a positive impact in this world by helping others get their best work out in the world and we've had the privilege of doing this kind of work for more than 20 years. You can learn more about us here.

You will be warmly welcomed into a group of no more than 12 others looking to level up their life and leadership and led by Charlie and Angela. If you enjoy people who want to live full, holistic lives both personally and professionally, are looking to make a positive impact in the world, are wanting to grow and learn and show up as their best selves in their organizations, families, communities, and all places they touch, you'll be in good company. 

We're so glad you asked. If your partner wants to attend as a fully participating attendee, then, yes, absolutely! We would love to welcome them. We know that there are partners who are in business together and we would love to host you both. If not, then not this time around. Our prior retreats have shown us that our participants are able to fully center themselves and what they need by being on their own for this deep work. Your fellow attendees are wonderful company, we promise. 

You can fly into Gregorio Luperon International Airport in Puerto Plata (POP), which is the closest airport and 20 - 30 minutes from the villa. A larger airport that is about an hour and a half to two hours from the villa is El Cibao International Airport in Santiago (STI). We will help you arrange for your transportation to and from the airport and will work to find shared shuttle options. Please note that you are responsible for the cost of your transportation. 


Once you register, Angela will be reaching out to coordinate details with you. Please plan to arrive at the villa before dinner time (around 6pm local time) but no earlier than 3pm. Please plan to leave the villa late morning on our final day. 

More Client Testimonials

Sarah C.B. Guthrie, MFA


I knew I needed to be at this retreat as soon as I saw it was happening. I am a professional artist and do much of my work alone, but there are things I want to create and share on a larger scale, including collaborating with other artists. As an entrepreneur, it can be easy to get lost in the day-to-day tasks and miss the big picture. The retreat gave me that deep reflective time I needed to create a vision and then map out the near- and long-term steps I am taking to bring that vision to life. 

In the time since I have returned from the retreat, I continue to implement practices and ideas that stemmed from our reflections and conversations that week. What's fascinating is that I am at ease as I make these changes--from upgrading space and buying better equipment, to having difficult conversations with more ease, to taking better care of myself, and removing obstacles to getting things done well. This retreat exceeded my expectations in so many ways, from the accommodations, service, and food, to the caliber of colleagues attending and what I learned from them, to the spaciousness and time to do deep work in an extended format with Angela and Charlie. The whole experience was very special.

Joanna Denton

Executive and Public Speaking Coach

The timing of this retreat was just right for me, having been on sabbatical and now looking for clarity on my next steps in my career. I came expecting to get help with the next steps in my business, but received much more than that. I feel like I am leaving with a sense of peace having tapped back in to what I want and knowing that I am heading in the right direction. And, I am leaving behind the fear. It's not going back with me.

Asia Orangio

CEO/Founder of DemandMaven

There's "pre-Charlie" and "intra-Charlie" when I think about the phases of my business. When we were pre-Charlie, I was completely overwhelmed and terrified by the journey that lay ahead of me. I had no clue what was up or down, what to do or avoid, what was normal or abnormal. I couldn't "see" my options in terms of building the business. I also felt so isolated as a founder and didn't know many others who had been there/done that who could show me how to build a business that would align with me and my goals. It was also hard to see my strengths as a CEO and where I naturally shined.


Enter Charlie - working with him has helped me see how much more possibility there is and he's coached me to grow into the best of what's ahead of me while staying in integrity with who I am and growing into my best life outside of the business. Since working with him, my team's headcount has doubled while still being profitable, we 5x'd in revenue, we're able to serve our clients better and more comprehensively, and we're able to scale in ways I didn't see when we started.

Alexis Grant

Founder, They Got Acquired

When I went looking for a business coach, I was overworked and stressed. I'd managed to bring in a lot of clients, but I didn't have the systems or people in place to service them all without losing sleep. Charlie helped me create a framework to do great work by hiring a project manager, setting expectations for my team, and developing systems so much of the company can run without me. After completing his six-month intensive, I'm now far less stressed, able to spend time on projects I enjoy, and have a clear plan for the upcoming year that includes more revenue and profit than ever before. I'd highly recommend Charlie for any small business owner, no matter where you're looking to take your company.