Level Up Your Life and Leadership Retreat

February’s Retreat is full and closed for registration. Add yourself to the first-to-know list for our next retreat.

It’s time to create a new day-to-day.

Leadership can be challenging, lonely, and all-consuming during normal times. But, let’s face it, times haven’t been normal since at least early 2020.

You’ve probably been carrying your team since the lockdown. In the face of the massive uncertainty that COVID created, it was leaders like you who held the vision, kept the team together, and got us through the dark times.

And it’s not like we’re through it, either. It’s just a different wave.

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

You’re meant for more than surviving the day.

Join us at a private villa from February 19 – February 26, 2023 to

get clear on and align your priorities with your dreams, legacy, and best work
map a plan for your team to get behind and push these dreams forward
connect with, soundboard, strategize, and adventure with (up to) 15 other conscious leaders, creators, and powerhouses who are likely friends you just haven’t met yet

*Registration is now closed for our February retreat. If you want to join us at the next one, add yourself to the list.

What You’ll Get Out of 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’s challenging for leaders and founders to see what to do differently. As Charlie says often, “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, leadership, and life. You’ll be connected with other leaders 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 transcendent part of yourself that’s 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 home. Your retreat experience will help you lead and create

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
more meaning at work because you can guide based on purpose and values
more peace and presence at home because you are better able to leave work at work, building a life that nourishes you
better relationships because you are clear about what and who matters and how to prioritize that
better health and wellness as you center your needs as a human and leader

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

If you’re an entrepreneur, you’ll get the same things above along with

more revenue, faster, as you are able to focus on your genius with confidence and clarity
less time spent in comparisitis and overwhelm
increased confidence to sell and stand in your value
less burnout because you can separate your self-worth from how hard you work

I’m Ready to Join

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.

We’ll Be Staying at the Best Retreat Center in the Americas

We have rented the Coco B Wellness Villa on Isla Mujeres, named the “Best Island Retreat Center in the Americas by Luxe Life Magazine.”

While it’s easy to see what you’re getting in the pictures below, we also want to remind you of what you won’t have to do.

You won’t have to go anywhere to be at the beach.
You won’t have to think about cooking, cleaning, or ordering food to eat well.
You won’t have to think about driving or getting from one place to the other.
You won’t have to be the vacation coordinator and manager.
You won’t be crammed through a bunch of content and not have time to breathe and experience being with other humans.

In the midst of all things you don’t have to do, you’ll be able to sink into who you are and who you want to be.

Click the pictures below to get a better view.

Highlights include:

Private Suites
Caribbean front property
Gourmet chef service for all meals
Daily maid service
Private pool and cabanas
Roof-top yoga shalas with all yoga props
Kayaks and paddle boards
Optional on-site massage and spa services
Personal concierge who can book excursions if desired

Andrea Trenner

CEO, Waterfall Community Health Clinic

Charlie has been a game-changer for my leadership and organization. As an executive coach, he’s one of the few people who can really see what’s going on, clearly put it on the table, and anchor to the conversation until it’s resolved. I can’t hide anything from him and I don’t want to because I know, no matter what, I and my organization will be better off from our empowering conversation. I engaged Charlie to facilitate team and board meetings for the same reasons — he’s flexibly able to keep us focused on exactly what we need to without getting bogged down into details and distractions that aren’t important for the meeting at hand. It always amazes me how he is able to create space for the unexpected nuggets that arise and turn into innovative solutions to problems we didn’t know we had. I’ve done a lot of strategic planning sessions over my decades of leadership and his have been the best ones.

I’m Ready to Retreat

February is the Perfect Time to Reset

On the personal side of things, February is a time of the year for many of us when we have hit our “I just can’t anymore” with the winter weather (here in the Northern hemisphere). Whether it’s the cold, rain, snow, or being stuck inside and pining for some sun, we need a good change of scenery.

But February is also a challenging or strange time when we see that many leaders, businesses, and teams need to “reset” or “realign” their plans for the year. The great intentions of the year and reality on the ground aren’t lining up.

If you’ve felt either of the “something’s gotta change” vibes above, you’re not alone.

The “Where” and “When” of the retreat are intentionally designed to give you what you need on both fronts. But so does the content and flow of the retreat.

Retreat Flow and Schedule

We will be gathering for a week to center you, make a real plan to implement change in your business and life, and map what you can give to your success pack so that you have the support you need going forward. The first half of the retreat will focus on you and the second half will focus on your team. Both need to be in alignment and you already know it needs to start with you.

We have very intentionally made this retreat an entire week so that we can go as deep as we need to go. We know how frustrating it is to invest time and money and energy into a retreat and not actually get what you needed and that’s not going to happen with us.

You’ll have time and space to:

focus on self-care
take this slowly
integrate at a human pace
roll up our sleeves together and co-create documents and assets together if that’s what you most want to do

How long have you been dreaming of just having a few focused days to get some of those best work projects done? And what could you do if you did that with fellow co-creators 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 going deep on the work, plenty of time with Angela to help center yourself and your needs and dreams, and enough time for everyone to get one on one time with both Charlie and Angela.

The bolded bullets below are the “content” part of the retreat, but, let’s face it, every part of the event is designed for transformation.

👇🏽👇🏽👇🏽(Click the ‘Schedule’ expander below to expand the schedule)👇🏽👇🏽👇🏽

Schedule

Sunday afternoon arrival

Settle into your private room and space
Get to know the other participants if you desire
We will have a welcome dinner and an intentional opening together as a group

Monday

We will use Monday as 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 Monday meets your needs. This could include:
- one on one time with Charlie or Angela
- a quiet space set aside just for you to do some initial pre-work, brainstorming, and sinking into what you need and want
- a chartered boat adventure
- a relaxing day by one of our private pools or on the beach with a great book
- so much more or nothing at all – again, this is all about centering you and your needs

Tuesday

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

Wednesday

Sessions with Charlie and Angela Focused on You
- Your 10 Dimensions – Now that you know about your different selves and energies, we can address the 10 Dimensions that make you the whole, amazing human you are and that leads to a flourishing, full life. We’ll help you identify where and how you can get the balance you need.
- When I’m Not My Best, I … Getting real with identifying how you handle times of stress, so that you have a clearer path forward and don’t go it alone.
- Prioritizing Joy, Fun, Adventure, Play, Pleasure, and the Giddies – ****You’ve identified your dreams, where you want to head, what selves need support, your 10 dimensions, and how you get in your own way – it’s time to optimize a better way to get you where you’re wanting to go.
- Environment Design – We’ll identify what in your environment is working well and helping you get where you want to go and what you may want to change to rock those dreams.

Thursday

On Tuesday and Wednesday, we centered you and made sure you are as clear as can be on where you are going and the personal decisions and moves you can make to help get you there. We’re going to use Thursday as an integration, recalibration, support, and/or open day. Again, this will be a day to choose what serves you best depending on where you are at on your journey.
- Options/possibilities include (but aren’t limited to):
  - One-on-ones with Charlie or Angela
  - Co-working or masterminding with other participants
  - A day of rest
  - A day of adventure

Friday

Sessions with Charlie and Angela Focused on Your Work with Your Team
- 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.
- Expectations Matrix – In this module, we’ll be guiding you to set clear role and responsibility expectations for the teammates you work most closely with. This could be your EA, your senior leaders, or your direct reports if you’re a team leader.
- Decision Map – Just like with having a guide to working with you and a clear expectations matrix, when your team has a decision map, the work they can do and the clarity of knowing ownership over what types of decisions, create amazing results on a team.

Saturday

Sessions with Charlie and Angela Focused on Your Work with Your Team
- Team Values and Core Habits – We all have values and we have ways of working with our team but are they clear to every person on the team? We will help you get clear on expressing your values and the core habits each teammate has to engrain to be successful.
- Annual Planning Wheel – Let’s get your annual plan captured and articulated in a way that your team can follow and action.
- 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. Trust us, you have not dropped everything you can.

Sunday Morning

Final Session with Charlie and Angela
- Putting This All Into Action – Your dreams have been shared and captured, you have identified how you can get there in a way that works better for you, and you’ve done the hard work of mapping how your team is going to help you get there. Let’s make sure you’re ready to take action when you get home.
Sunday late morning/early afternoon departure

I’m Excited to Join You

See What Our Clients Say About Working With Us

Cliff Worley

Senior Director of Portfolio Growth Marketing, Kapor Capital

When I started working with Charlie, I had a lot of opportunities ahead of me but wasn’t focusing on the best ones. Charlie’s strength is that he’s able to help you see your next best move and do the work it takes to make it happen. I’ve worked with him as an entrepreneur and an executive, and in both cases, he guided me to see and take my best shot. Our work together was a critical part to getting me to where I am today.

Leslie Griffin Robertson

Vice President, User Experience, Oracle Health and AI

“Charlie is a phenomenal facilitator, advisor, and thought partner. He asks great questions, and he listens carefully. He has a knack for seeing what’s really going on, naming and calling it out in a way that’s firm but non-divisive, and then guiding groups and individuals to actually engage with the challenges or opportunities. Because of his facilitation, we were actually able to get valuable insights into our org patterns, and figure out ways to optimize them. I’m looking forward to the next opportunity for Charlie to work with my leadership team, as well as with my broader organization.”

Eric Zimmer

Founder, The One You Feed

Working with Charlie has positively changed our business and life in ways that I couldn’t have imagined before working with him. Our revenue has grown substantially, and for the first time in our business we had a highly profitable year.Even more than that, though, is that happened during a year where we took 2 months off for travel and vacations and started working less in the business.Equally important is that working with Charlie has helped me to feel more relaxed about where we are and more optimistic about the future. The peace of mind we have gotten from working with him is truly invaluable.We are also a couple in life and business and Charlie has helped us navigate that more effectively. He helps us to have hard conversations and grow together.Each time it comes time to renew with him, I’m surprised that it’s obvious that we should – our business and life is better with Charlie helping us navigate it.

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.

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, 14 years consulting leaders in various industries in for-profit and nonprofit industries, writing award-winning books, and serving on various boards. My forthcoming book, Team Habits, is a guide to creating practices in teams that create great results and belonging.

Angela Wheeler. 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.

I’m Interested and Would Like to Learn More

Dates, Location, and Payment Details

Dates: Sunday, February 19 – Sunday, February 26, 2023

Location: Coco B Wellness Villa on Isla Mujeres, Mexico

Cost: $12,000 through January 27th, 2023 (closing date). Includes a private suite, all meals while at the villa, coordinated shared transportation to and from Cancun airport to the villa, and all retreat sessions and content.

Our current pricing for a one-day in-person retreat for new clients starts at $10k (for small companies) and new clients pay $1,000 or more per session with Charlie. Between the open time we’ll have, the time you’ll get with Angela, the conversations you’ll have with other attendees, and the once-in-a-lifetime vacation, you’re getting a lot of bang for your buck.

Ready to Join Us?

If you are ready to grab one of the limited seats we have available, you can do so by filling out this super short form. Angela will reach out to discuss payment and retreat personalization with you so we can co-create the retreat that best serves you.

I’m Ready to Join You in Mexico

Frequently Asked Questions

This looks amazing, but I’m still not sure if it’s a fit. How can I get a better idea if it’s for me?

If you are a leader, manager, or entrepreneur 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 sun-cation, being pampered 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 professionally….you’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 and help co-create the retreat that is a best fit for you.

I’m newer to Charlie and Angela and Productive Flourishing. How can I get a better feel for them?

Welcome! We are honored you are here. We are big-hearted entrepreneurs, 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.

What kind of people will be attending with me?

You will be warmly welcomed into a group of no more than 15 others looking to level up their life and leadership and led by Charlie, Angela, and Productive Flourishing teammates. 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.

Can I bring my partner?

We’re so glad you asked. Due to several attendees asking, we have set things up with the venue such that you can bring a non-participating partner, spouse, or adult family member at cost, to enjoy this experience with you. By non-participating, we mean that their at cost payment would cover their lodging and food at the villa. They would not be participating in the retreat events and content, but would be able to use this as a vacation and time with you when you’re not in sessions.

How do I get to the villa since it’s on an island?

You will fly in to Cancun airport and from there we will help you with getting to the villa on Isla Mujeres. We will be coordinating shared travel to and from the airport to the villa. If you prefer not to wait to share a van and boat with other attendees we will share information for you to arrange your own travel from the airport to the villa and back. We will coordinate this in January, after registration is complete and most people have booked their flights.

What flight times should I be looking for?

Once you register, Angela will be reaching out to coordinate your experience for you, which will include a lot of the details. If you want to get started on booking a flight right away you can plan to be at the villa after 4pm on the 19th, but in time for a shared dinner. If you were to get into Cancun by mid-afternoon that would likely work really well for shared transportation to the villa. We will plan to close the retreat by noon on the 26th. A late afternoon flight out of Cancun would be a good fit for this.