Level Up Your Life and Leadership Retreat

Update as of May 26: We have confirmed our dates and location for our September retreat and are excited to announce that we have rented a beautiful lodge in Bend, Oregon from September 10 - 15. Only 3 seats are remaining. Early registration ends Wednesday, May 31st. Deposits received by then will secure the lower rate.

Entrepreneurship 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 business since the lockdown. In the face of the massive uncertainty that COVID created, it was creators like you who held the vision, kept the business going, 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 entrepreneurs and founders are exhausted, burned out, demotivated, and just getting through the day-to-day.

You're meant for more than surviving the day.

Join us September 10 -15, 2023 in beautiful Bend, Oregon to

get clear on and align your priorities with your dreams, legacy, and best work
map a plan for your success pack to get behind and push these dreams forward, helping you make a greater impact
connect with, soundboard, strategize, and adventure with (up to) 7 other conscious founders, creators, and powerhouses who are likely friends you just haven’t met yet

The participants of our first retreat are still seeing transformations happen every week that are coming from their experience at the retreat. We're excited to see what will unfold for you, too.

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.

Yes, This is For Already Successful Founders

Here's the thing: when you're an entrepreneur or founder who's done pretty well – you have a successful business that keeps you well off but not super-rich, a brand/business that people know of but isn't the top 1-3 in your field, and you have a decade or more under your belt – it's really hard to find advisors, communities, and events to go to that are relevant to your acumen or level of success. The ones most know about get all into hustle bro, digital marketer, optimize-your-funnel syndicate stuff that's useful but annoying (at best) and extremely problematic (at worst).

Have you found yourself bumping up against an upper-limit mindset?

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. Okay, honestly, we're still there; guiding people through it is one of our superpowers. Getting through it ourselves is an emergent capability. Teach what you need, you know?

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.

I'm Ready to Join

You Won't be The Only

When we announced the first of these retreats earlier this year (which was a phenomenal success and experience for the attendees and us) we had a theory about who would be interested, but a theme that emerged is that really successful entrepreneurs who don't necessarily consider themselves leaders saw it and thought "that looks really cool, but I'm not really a leader." But in the back of their heads, they also wondered if they'd be the "only" best-selling author, well-known entrepreneur, or person who normally leads these kinds of things.

If you spot it, you got it. Let's work on it together.

If you are already familiar with us, you've probably experienced the diverse and high caliber set of leaders, change-makers, and entrepreneurs that run with us. You won't have to worry about being the smartest and most successful person in the room, and, even if you are, we have a knack for working with people used to that without going the problematic routes alluded to above. Crazy 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.

Andrea Zamora

Founder, Brite Side Consulting

I went to the Level Up Retreat thinking I was going to take back a plan to be a better leader and really what I've brought back is a different, better version of me. I came home with possibilities I didn't know I had; the possibilities of a magnificently delicious life. The beauty of that particular experience is that I have gone from a leader on paper with expectations and rules, following all of the books and podcasts over the last 10 years and scripting everything, to now leading from the heart.

The implementation of the retreat gifts have allowed me to finally give myself the grace to meet my true desires. My schedule is geared to put myself first and find joy in life's precious moments while tapping into new talents and adventures. I can't put a price tag on that. It's priceless.

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 can be challenging for founders and entrepreneurs to see what to do differently with already overfull schedules and responsibility overload. 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 founders 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

- more revenue, faster, as you are able to focus on your genius with confidence and clarity
- focus to extend your reach and impact beyond the success you've already achieved
- 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
- more quality time for the important things outside of business

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

I'd Love to Talk About Attending

Sarah C.B. Guthrie, MFA

Artist/Founder

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.

We'll Be Staying in Beautiful Central Oregon

We have rented a private, luxury lodge in Bend, Oregon.

All participants will have their own room and bathroom for privacy. We're going to take care of it all.

You won't have to go anywhere to be surrounded by beauty, as the lodge overlooks majestic Tumalo Lake in the Deschutes National Forest.
You won't have to think about cooking, cleaning, or ordering food to eat well. We have a private caterer taking care of all meals.
You won't have to think about driving or getting from one place to the other. All of your needs will be met at the lodge.
You won't have to be the vacation coordinator and manager. All you need to do is get yourself there and we take care of the rest.
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.

I'm Ready to Retreat

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.

September is the Perfect Time to Reset

On the personal side of things, September is a wonderful time, full of renewed time, attention, and focus after the often surprisingly busy summer months that can pull us in many different directions. It's a time many of us can get back into our own personal groove.

On the professional side, we founders also need to realign our priorities, projects, and team or success pack to end the year strong. The Level Up Retreat is intentionally designed to give you the space and support you need to reset and recalibrate.

Not only are the timing and location of the retreat carefully chosen to facilitate personal/professional recalibrations, but the content and flow of the retreat are also designed to help you achieve your goals. With workshops, coaching sessions, and engaging discussions, you'll learn from expert facilitators and connect with like-minded peers, all while developing the skills and mindset necessary to take your personal and professional growth to the next level.

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.

Retreat Flow and Schedule

We will be gathering for five days 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 and others you work with in your business. 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 host 6 - 8 participants maximum, so if you join us you know you will have a lot of focused time for you and the support you need. 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:

take this slowly
integrate at a human pace
actually have your own self care and needs centered
roll up our sleeves together and co-create documents and assets to take the great work you have done and make sure it is actioned when you return to work

How long have you been dreaming of having a few focused days to get some of those high value projects done? And what could you do if you did that with fellow 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 and Angela to go deep on the work, and space to collaborate and work outside of scheduled sessions, also.

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)👇🏽👇🏽👇🏽

Tentative Schedule

Sunday afternoon/evening arrival - Day 0

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 - Day 1

Sessions with Charlie and Angela Focused on You
- Opening, Roadmapping, and Intention Setting
- 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.

Tuesday - Day 2

Sessions with Charlie and Angela Focused on You
- Balancing the Different Selves and Energies - Understanding the different aspects of yourself and how they show up in your life and work.
- 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.
- Tuesday evening will be open time to prepare for taking the Work That Was Centered On You into How You Work With Your Team. Intentional space is given to integrate and recalibrate for the remaining deep work and a group activity will guide you at this mid point.

Wednesday - Day 3

Wednesday morning will be open time to prepare for taking the Work That Was Centered On You into How You Work With Your Team. Intentional space is given to integrate and recalibrate for the remaining deep work.
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 and Decision Mapping - In this module, we’ll be guiding you to set clear role and responsibility expectations for the teammates you work most closely with and a decision map, which shows the work they can do and gives clarity of knowing ownership over what types of decisions, create amazing results on a team.

Thursday - Day 4

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 as soon as you are back to work.

Friday - Day 5

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.
Friday early afternoon departure

I'm Excited to Join You

See More From Our Clients About Working With Us

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.

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.

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.

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.”

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, 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.

I'm Interested and Would Like to Learn More

Dates, Location, and Payment Details

Dates: September 10 - 15, 2023

Location: Tumalo Lake Lodge just outside of Bend, Oregon

Cost: $8,000 if paying in full prior to May 31st, 2023. $9,000 if paying in full after May 31st or if a payment plan is needed. Includes a private suite, all meals during the retreat, and all retreat sessions and content. Transportation is separate.

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 Charlie and 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.

We require a $1,000 deposit (that goes towards the total cost) to reserve your spot. The deposit is fully refundable only if we are unable to reserve our retreat location due to attendance. When we have five reservations we will reserve the location; at that time full payment is due or your first payment on the payment plan we have agreed to.

Ready to Join Us?

If you are ready to grab one of the limited seats (maximum of 8 participants) 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 Beautiful Oregon

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 founder, entrepreneur, or leader 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 vacation in sunny Central Oregon, being taken care of for five days, 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.

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 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 7 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.

Can I bring my partner?

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. We realized at our prior retreat that our participants were able to fully center themselves and what they needed by being on their own for this deep work. Your fellow attendees are wonderful company, we promise.

How do I get to where we are staying?

There are several ways to get to the retreat. If you are flying into Portland, you can rent a car or take the bus that goes from Union Station in Portland to Bend. There is also a smaller municipal airport that flies in to Bend. Should you want to carpool with other attendees we will get that information from you and make introductions so that you can arrange for plans together.

What flight times should I be looking for?

Once you register, Angela will be reaching out to coordinate details with you. If you are ready NOW to get things scheduled and purchased, please plan to arrive in Bend late afternoon on September 10th and plan to leave Bend late morning on September 15th.