• Hilary Young

Lady Bosses I Love: Jenn Masse

Jenn and I became internet friends long before we met IRL. We connected in the early days of the pandemic when we were both participating in the same (virtual) conference and started following each other on Instagram. I was instantly drawn to Jenn's honesty, her authenticity, and how unapologetically herself she is. It didn't take long for Jenn and I to become each other's biggest cheerleaders. But that's really at the heart of what she does for a living (and who she is as a human): Jenn cheers you on, lifts you up, and consistently shows up for you.


Through her business, Conshy Coaching, Jenn helps women get more clarity about their purpose in life, feel more confident in their careers or businesses, and become more motivated and empowered along the way. Jenn truly practices what she preaches (or maybe she preaches what she practices? Either way, it works.) and recently made a huge move across the country to chase her dreams. While I miss having her in my time zone, it's been such a treat to watch her tackle something new and scary with ease and grace.


Jenn Masse: Conshy Coaching


What is the name of your company and what do you do?


I run Conshy Coaching and I empower women, small business owners and executives to break free from the limitations holding them back so they can unleash their full potential.


How long have you been in business?


Depends on when you start counting! I’ve been coaching since November of 2018 but Conshy Coaching officially launched when I became certified and quit my corporate job in July of 2019.


How did you decide to launch your own business?


I’ve always known that I’ve wanted to own a business one day. Throughout the years I’ve had different ideas and concepts for brick-and-mortar-type businesses, but due to timing, fears, and a lack of clarity of how they aligned to my purpose, none of them made it off the drawing board. I have always believed that I was put on this earth to empower and inspire people, so once I discovered the power of coaching, a fire was lit within me. I enrolled in a coaching program, got certified, quit my 9-5, and the rest is history.


What challenges did you face in the process of launching your business?


Two things that I distinctly remember: First, tuning out the noise and focusing on what I wanted my business to look like and how I personally wanted to grow it. I felt a lot of pressure to “prove” that my decision to walk away from a six-digit corporate salary without a single client, was the right decision. This pressure was a huge distraction and pulled me away from my deeper purpose. It wasn’t until I truly believed in myself and my vision of success… one that prioritized my core values of freedom and connection and my desire to help other women redefine success for themselves, that things started to fall into place.


Second, realizing that my friends and family didn’t support me in the way I thought they would. Rather than support and questions about how they could help me grow my business, I received a lot of passive aggressive comments and blatant judgmental statements about my decision, ability and privilege to walk away from corporate without a single client. It was incredibly hard to stomach and my inner critic was having a BLAST with their comments, but ultimately, I knew that I could not stay in the toxic environment any longer, and empowering others through coaching truly was my life purpose, so I reconciled with my emotions, created boundaries to protect my energy and built a new supportive community from the ground up.


Did you feel as though there were resources available to you, specifically as a woman business owner?


I actually think there are too many resources! There is so much noise out there with free master classes, lead generators, youtube videos and people trying to tell you what to do based on what worked for them. It can lead you to spending time and energy on things that aren’t necessary or don’t lead to forward momentum. Ultimately, what works for you is going to be a unique combination of everything your research reveals. Working with someone to help you sort through all the information and help you determine what aligns with your vision of success is critical to beat the burnout and reduce overwhelm.


Do you have a mentor?


Mindset and Empowerment Coaching is still relatively new, so while I don’t have a specific mentor, I do have a few coaches in my network that I bounce ideas off of, celebrate wins and ask questions about what they see for the future of coaching.


Books you recommend?

[Note: the below links are Amazon affiliate links]


Brene Brown - Rising Strong

Brene Brown - Daring Greatly

Michael Bungay Stanier - The Coaching Habit

Marc Brackett - Permission to Feel

Sally Helgesen - How Women Rise


What do you love most about running your own business?


The freedom and flexibility I have over my schedule! Freedom is my number one core value, so this is critical for me. If I’m not feeling well I can take a nap, if I want to connect with someone I can go grab coffee or schedule an impromptu walk & talk call, I can go to the gym and not worry about rushing back to have my computer on by a certain time, the list goes on!


What is your least favorite aspect of running your own business?


The freedom and flexibility I have over my schedule. 🤣 I’m deadline driven procrastinator, and since much of my work is not deadline specific I procrastinate endlessly. I combat this with a number of creative accountability practices, but ultimately, being on an island without anyone to help me brainstorm ideas or hold me accountable can make it difficult to stay motivated. It’s these times that I reach out to my coach and support network for support and encouragement.


What is your best piece of advice for other women who are thinking about launching a business?


Get really clear in what you want and why you want it. This vision and your passion will be what pushes you through during the lulls and difficult moments. One of the first things I introduce to clients is my success formula: Awareness + Strategy + Mindset = Success. This formula only works if you’re incredibly clear in your vision of success because if you’re vision is vague, then you run the risk raising awareness about things that don’t matter, set strategies that don’t get you closer to your end goal, and spending time second guessing yourself rather than having a strong, resilient mindset that will help you trust the process and keep growing forward.


Know your core values and guiding principles. These will help you stand in your authenticity and make confident decisions about how you run your business.


Awareness is everything. In addition to your values, be aware of your strengths, your saboteurs, limiting beliefs and external barriers to success. Once you are aware of what these are, stay mindful of how they are showing up when you are working with your clients, marketing your business, or evaluating external coaching opportunities.


Authenticity is best. Your clients and customers will want to work with you for a reason. When you show up as your whole, authentic self, you give them permission to do the same. Personally, I wear baseball hats and comfortable clothes to my client meetings, and my clients who are mainly women love it. They have thanked me time and time again for making it a comfortable environment where they do not feel the need to shower or do their makeup before our sessions.


Build a strong support network! Partner with an ICF Certified Coach who can help you dig a bit deeper and who gives you a safe space to discover what your vision/brand/purpose is, and then helps you stay accountable to making choices and business decisions that align with that vision. Also consider working with other professionals like branding specialists, professional photographers, web designers, copy writers, social media experts, and anyone else who can take care of areas of your business that need additional support but aren’t your primary focus.



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