I was on the beautiful island of Isla Mujeres attending a weeklong leadership retreat. It was a Wednesday morning, the first session of our third day. Soon into it, on the couch with the beautiful Caribbean Ocean as my backdrop, I am crying. 

Y’all, I don’t cry easily. So when I do, it’s because something deep inside me has been touched.

And I cannot stop the steady stream of tears running down my cheeks.

I also can’t stop thinking: You are not supposed to cry at a leadership retreat!  

My tears were the cathartic release I didn’t know I needed. 

Turns out, the entire retreat was an experience I didn’t know I needed but desperately did. 

The timing of the retreat was perfect. For the last 18-months, I’ve been on a very intentional and strategic journey to level-up the operations and speaking arm of my business. At the beginning of this year, I decided it was now time to turn my focus to the coaching arm. So, my purpose for attending the retreat was to get ideas on how to level-up this critical pillar.

And given how much I’ve been describing my recent choices as me taking things to the next level, the retreat’s title was kinda perfect, too. Admittedly though, I didn’t tune into that alignment until I was on the plane headed home.

Back to Wednesday…

First, Go Inward

Later that evening, in the quiet confines of my room looking out to this gorgeous pool, I was reminded of how everything is an inside-out job

Regardless of the topic (work, life, money) or the industry (leadership, law, finance, marketing, medicine, beauty, sports, the arts), if you want to improve your performance in it, you must first go inward. 

Despite what some might have you think, there simply is no way to escape the personal development aspect of what it means to get better at something. 

For the most part, our culture “rewards” doing over being and compartmentalizing over taking an integrated, holistic approach to almost everything.  

So, in a culture where taking an inside-out approach is underrated, it was a pretty radical move, by Charlie Gilkey and Angela Wheeler, Ph.D., to design an experience that centered and encouraged you to bring your whole self to the table. That encouraged you to lead with BEING.

I often say owning a business will take you on quite the personal growth and development journey. Because whatever you’re looking to make better in your business typically requires that you, personally, uplevel in some way. It might be in the realm of self-awareness, self-esteem, or skills. Or, your leadership. 

The same is true when it comes to improving your financial situation and navigating complex financial decisions. 

The things you wrestle with in terms of self-worth* and your place in the world…whew, chile!  (*I mean this in terms of asking for what you want, not in the price you charge for your work. In case you don’t know, I hate the phrase, “charge what you are worth”!)

As I posted on social media, I unpacked my bags the night I got home (remember, I’m Type-A and an Enneagram 3!), but I’ll be unpacking all that was unlocked for me for days, weeks, and months to come.

Create Your Own Retreat?

In order to integrate my takeaways from the retreat, there are a few habits I’m going to need to change about how I approach my work and the management of my business. 

I’m also going to need to create my own mini-retreats to sustain me throughout the year.

In case you want to do the same, here are five (5) things to keep in mind regarding the purpose of a retreat as you design your experience. 


Taking a deeper look at your actions, attitude, and environment so you can better understand how you think, feel, and behave is paramount. But before you examine what has happened, why, and what you are going to do about it moving forward, first give yourself the permission and the space to DREAM. Sit for as long as you can with the question: What do you WANT?  

For me, the sequence matters because being an action taker is my default mode of operating. I’m a striver; I get sh*t done. I’m also a problem-solver and frequently identify the unexpected solution. I’ve been described as contrarian, and I’m okay with that label. 😀

Meaningful relationships

I had the pleasure of retreating with others. However, going into the experience I only knew the co-facilitators, Charlie and Angela. I met the others as strangers, but we certainly left with a deep and tremendous bond. 

You may end up having a solo retreat experience. If so, I hope you’ll be able to debrief with others. Because, while there are aspects of a retreat that are meant to be a solo endeavor, one of the many benefits of my time in Isla Mujeres was having my blindspots revealed…by and through others. We are often too close to see what is glaringly obvious to others. And, the “seeing” by others can sometimes give us the clarity we didn’t know we were missing.

Time to do nothing

Build in time to literally do n.o.t.h.i.n.g. If your retreat is a few hours, then set a timer for 15-20 minutes to simply be – staring out a window counts. In the stillness of the quiet, you may have a creative spark that leads to new ideas or unblocks answers you’ve been seeking.

Higher EQ

A deeper sense of self-awareness and self-appreciation doesn’t mean being perfect. But man, being comfortable in your skin, knowing deeply what you uniquely bring to the table, being as honest about the skills and habits you need to cultivate and deepen as you are about the ones you do with ease, having a teachable spirit, having and honoring your boundaries, and remembering that you get to want what you want….that is sexy as hell! 

Layer onto this a heightened awareness of the emotions of others around you…you are on fire! 

Retreats can help you increase your emotional intelligence.

What game are you playing?

If you approach your work, life, and money choices as if you are playing the long game, you do so very differently then if you’re in it for the quick win. 

You have a growth mindset in terms of the projects, priorities, and goals you set, and the team you assemble to help you along the way.

You make sure to take time to celebrate the successes along the way. And when setbacks inevitably occur, you view them as opportunities to move forward better and, perhaps, more resourced. 

Taking an inside-out approach to work, life, and money, may be underrated by our culture at large. But, you don’t have to adopt that perspective. I’m here to suggest you don’t!

And if I haven’t made enough of a case for why it matters, consider this: Whether the retreat you design for yourself is for a few hours, a full-day, a long-weekend, or maybe you get away for a full week like I did, it is a form of self-care.  

p.s. The Level Up Your Leadership Retreat was hosted by Productivity Flourishing co-founders, Charlie Gilkey and Angela Wheeler, Ph.D. If they host it again, I’d highly recommend it. 

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