Embracing Vulnerability & Connection


If I’m being completely honest, a lot of owning a business feels like grueling push-past-your-fears kind of work. The raw, rewarding emotional journey of learning how not to be in our head about one insecurity or another. The fears I feel and hear from clients most often: Questioning what will happen if “it” does or doesn’t work out, feeling pressure to follow a certain version of success, worrying if work will ever pick up again after it has slowed, and sometimes—even when things are going great—finding ourselves anxiously anticipating the next shoe to drop.

There’s a lot of responsibility we take on as small business owners, the list of to-dos can be overwhelming even without these external pressures.

Prime example: Part of any successful marketing strategy is knowing what your competition is doing so you can establish a better hold in the marketplace. Typically this results in more time scrolling Instagram, staying current on your favorite industry blogs… and soon what started out as a little objective research quickly devolves into comparing yourself to others and ultimately, leaving you feeling depleted.

With every small business there’s a lot to think about, process, and execute in any given day. But what I’ve seen (and experienced!) in my own business is that when I let my own thoughts run rampant without adequate time to re-evaluate, I get myself into trouble.

This has translated into me saying yes to every opportunity, hopeful it might lead to something, but instead leading me to burn out and starting to feel untethered. Operating my business from a place of fear has led me to doing things a certain way because I feel that’s how I should be doing it.

So, how can we help prevent ourselves from falling into this trap of self doubt and better arm ourselves to move past the fears we sometimes don’t even know we have?

The most effective answer I’ve found to this question is: Embrace vulnerability & connection!

It’s hard for me to even think about where I would be in my life or business without the immense support of some truly incredible women. I was chatting with a dear friend, and fellow business owner, the other day, and we got to chatting about this strange interconnectedness we both feel between being a business owner and doing deep soul work.

Owning a business requires you to tap into your intuition to make decisions from a place of visceral knowing. It’s a deeply personal journey to create a product or offering and begin to put it out into the world. You have to remind yourself that the success of the offering does not personally reflect your worth as a human. All of these lessons about trusting your intuition, leaning into the fear and doing it anyway, not allowing what or how much you produce be a sign of your own worthiness. It’s all a very vulnerable and autonomous practice.

Something magical happens when you’re finally able to silence your ego enough to share these intimate details of your mind and soul with others.

Because, trust me, there are other beautiful, worthy people out there going through similar, if not exactly the same, fears just waiting to connect with you! I’ve experienced and dissected this narrative with clients and fellow small biz friends from around the world since I started my business in 2016. And it’s these conversations—connections—that have kept me aligned with my truth.

Please don’t misunderstand this as me claiming to have never lost my path. This has happened several times, and, as is life, I am bound to run into blocks down the road—much like the struggles I’ve shared with you these past few months. However, I can unequivocally say that even with all the fear I feel in regards to the uncertainty of what comes next, I’m able to hold onto hope because I have developed friendships with people who remind me of what’s important on a daily basis.


There is an undeniable bond that is formed when women can gather together, strip away the normal stressors of everyday life, and simply be.

Nothing is more inspiring than being in a safe space where you are lovingly challenged to push your ideas and dreams farther than you ever could on your own.

When I was in Joshua Tree this past spring, I was having a conversation with a few of the women, and one asked the group, “What is your big, wild and crazy, epic business dream?” We then went around the circle sharing our wildest dreams. I think about that moment often because whenever things feel impossible, I remember that there are women who support me unconditionally to follow that dream. I haven’t found anything more powerful than voicing that into the world and truly being seen as I do. It’s purely transformative to uncover your deepest desire, and then be in a safe space to share it with others.

I don’t think you ever overcome the fear of running your own business. Once you master one thing, another challenge will present itself, so I think it’s a matter of staying nimble and being willing to adapt.

This is why I feel so strongly that taking time away from the normal daily grind is so important to reconnect with your purpose and your power so that your business stays inspired.

This is what inspired me to partner with Robin Vega of Brand + Bash to create The River Gathering this fall (Sept. 23-26 in Buena Vista, CO). We're calling it a "working vacation" of sorts because we can both relate to the guilt of taking a vacation when you run a small business, and the stress of running a small business without vacation. It's important to take time—for both you and your business. Almost as a preventative measure, keeping you centered and focused on your truth. 

Even though I know the importance of pausing and reflecting, I can take a look back now, and see how I definitely wasn’t giving myself the time I needed. If I saw a blank space in my calendar, I would fill it. But as an internal processor, I integrate information best by writing it down afterward. So I started feeling rushed and disconnected during my meetings because I wasn’t giving myself enough time to reflect on one action and completely transition from one client to the next.

Things have slowed down in my business, so I’m able to look back with hindsight to see how I was doing myself a disservice. And now that I’ve recognized that, I’m able to add in additional buffer time before/after each client.

However, everyone is different, so I think it’s vitally important to understand what works for you. Maybe you need to give yourself a walk around the block before you make a decision. Maybe you need to ensure you don’t see any clients before 11am. Maybe you need to start your day with a creative pursuit before diving straight into work. Whatever it is for you, make sure you’re finding space to simply be, and make it a part of your daily habit. It’s in that quiet space when we allow our mind to settle that we can finally synthesize everything that’s been happening and make clearer decisions.

While I know the fear will continue to arise, I’m working to strengthen my resiliency so that I am not as viscerally impacted and thrown off course each time something happens. Obstacles will continue to be placed on my path, and instead of expending energy being frustrated by them, or running through a list of why this isn’t fair, or engaging in other self-sabotaging behaviors, I’m curious about exploring how I can find a deeper connection to myself.

I see it like this: If we are all trees in this forest of life, my soul mission is to not worry about how tall the other trees around me are growing. I can witness their growth and quietly observe, but I want to focus more on how deeply I can grow my roots. Because I know, in time, the winds will rage, and as I’m swaying in the storm, I can rely on my root system to keep me grounded and safe from these external forces.

If you’d like to work on getting into a vulnerable, truth-seeking headspace for your business, I’ve prepared a few journal prompts to help you dig deep and discover what it is YOU need from your business right now:

  1. What do I long for?

  2. If I were to focus more on the joy, and less on the details, what would my business look like?

  3. What’s the right next step?

  4. What am I willing to tolerate in my work life? What am I NOT willing to tolerate in my work life?

  5. When was the last time you felt like an opportunity was an immediate, “Hell YES!”? Reflect on that experience, and what about it made it the perfect opportunity? How can you bring more of that into your business?

We all spend so much time working in the daily activities of our business that we rarely give ourselves the time to zoom out and work on the larger picture. To ensure our daily tasks are in line with our ultimate vision, we do have to dedicate time to look at our business as a whole, and there is no better place to do that than in the company of others who truly understand what you’re going through. It’s also a great opportunity to get out of your head and share some of these ideas with others.

As you do, pay attention to how you feel as you share these ideas with others. Don’t worry so much about their reactions, but what are you feeling in your body as you share? Can you feel yourself smiling? Did you hunch your shoulders a little? Was there a slight flutter in your heart? Observe these signs to help point you in the right direction.

We often have the answers we need right in front of us, it just takes a little focus and giving yourself the grace to be. If you'd like to share your observations from this exercise, or your discuss any struggles you may be having with embracing vulnerability and connection in your business, I'd love to hear from you. You can send me a DM on Instagram, or email me directly at hello@maggiegentry.com. 


Photo credit: Creating Light Studio


Are you interested in connecting with other like-minded female entrepreneurs during a 4-day retreat in Buena Vista, Colorado this September? Join me for The River Gathering! Consider it a working vacation—where we'll use daily yoga + meditation, plenty of free time to explore, and gorgeous mountainside accommodations to help inspire you to dig deep and create solid marketing strategies that propel you forward. The agenda is full of exciting activities and workshops, we promise you'll leave feeling refreshed and re-inspired! Sign up by June 30th for Early Bird pricing.

And if you aren't yet at the stage where you can make this investment, don't forget about my Virtual Office Hours.
30-minute, 1-on-1 chats—honest, heartfelt conversation—always free.