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Jennifer Masse of Conshy Coaching: “You must know yourself, and be yourself”

In my opinion, successful coaches all have one thing in common. They are 100% unapologetically themselves. The best coaches are coaches who walk the talk and are there to strategically partner with their clients to help them creatively find their own solutions. So, to be a great coach, you must know yourself, and be yourself. […]

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In my opinion, successful coaches all have one thing in common. They are 100% unapologetically themselves. The best coaches are coaches who walk the talk and are there to strategically partner with their clients to help them creatively find their own solutions. So, to be a great coach, you must know yourself, and be yourself. That’s it!


The coaching industry is now tremendous. It is a 15 billion dollar industry. Many professionals have left their office jobs to become highly successful coaches. At the same time, not everyone who starts a coaching business sees success. What does someone starting a career as a life coach, wellness coach, or business coach need to know to turn it into a very successful and rewarding career?

In this interview series, called “Five Things You Need To Create a Highly Successful Career As a Life or Business Coach” we are interviewing experienced and successful life coaches, wellness coaches, fitness coaches, business and executive coaches and other forms of coaches who share the strategies you need to create a successful career as a life or business coach.

In this particular interview, we had the distinct pleasure of interviewing Jennifer Masse.

Jenn Masse, Owner of Conshy Coaching, is a Certified Mindset and Empowerment Coach who helps women and small business owners reframe their own stories to become more aware of the ways in which outdated patterns and belief systems are holding them back from unleashing their inner power and achieving greatness. Learn more at www.conshycoaching.com or email [email protected]


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and what brought you to this particular career path?

Sure! Prior becoming a Certified Coach, I worked in a corporate environment for over a decade. From accounting to project management, to sales, to marketing and business development — I was constantly chasing careers, promotions and this ‘preconceived notion of success’ that was promised to bring me happiness. I was incredibly good at what I did and excelled in all these positions, but constantly felt under-utilized, under-valued, and “empty.”

It wasn’t until I found myself crying ugly, snotty tears in my boss’s office did I realize that something needed to change. It was in that moment that I realized I would never truly be appreciated for the value I could bring, or in the position to truly empower and inspire other people, until I took control of my story, my future, and my career.

I enrolled in an ICF credentialed coaching program the next day.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

  • Authenticity — I am a firm believer that there is no “right” way to do anything, only your way. There are so many people out there trying to sell you these signature systems, programs and solutions that will help you scale your business in mere months, but the truth, is that you are the only one that knows what is best for you, and your business. There is value to working with professionals and coaches but find one that empowers you to find your own answers and your unique formula for success.
  • Resiliency — I have always been strong-willed, but I have learned that it’s not my strong-will, but rather my resiliency that has allowed me to bend, pivot and grow. No matter what challenge or hurdle I am faced with, I stand firm in my mission to empower and inspire people and make choices that deeply aligned with my values of freedom and connection. This is what helped me quickly pivot and thrive at the beginning of the pandemic and continues to help me grow and pivot as the needs of our society continue to change.
  • Curiosity — I used to think I knew all the answers, the right way to do things. I was incredibly judgmental of those did things differently or couldn’t get to the answer as quickly as I did. These behaviors stifled my professional growth, led to deeply rooted resentment, and extreme levels of burnout. It wasn’t until I let go of my need to be in control, my need to be right, and my obsession with being “the best” that I was able to tap into my full potential. I now approach every aspect of my life with curiosity. Curiosity has helped me be open to learning new information, bend and pivot my business model as new information arises, and — most importantly — it helps me be an amazing coach for my clients. Curiosity allows me to be fully present in the moment, and rather than trying to solve their problems, I can listen to what they are saying, or not saying, to help them connect the dots and find their own answers and solutions.

How have habits played a role in your success? Can you share some success habits that have helped you in your journey?

Oh, they have played a huge role. The first step of my signature success formula is awareness. Awareness of our strengths, saboteurs, limiting beliefs, aspirations and so-on. This formula is what helped me realize how I had been sabotaging my success for years. Now that I understand my thoughts, behaviors, and emotions a bit better, I have developed habits and strategies that allow me to operate from a place of authenticity and maintain a resilient mindset even when things don’t go as planned.

  1. Letting go of control. My top self-sabotaging behavior is trying to control every situation. But, I realized that this was due to a lack in trust in others, and was ultimately stifling my personal and professional growth. I’ve since created the habit of stepping back to take a holistic view of a situation, there are definitely still times that I need to jump in and take control — especially in my business — however, most times, I can take a breath, and realize that the outcome likely won’t change whether I spend my energy on it or not. This has helped me show up as a better employer, a better spouse, and most importantly, a better coach because I am not trying to “force” my clients to see things my way — I am able to provide them with a safe space to explore doing things in a way that is most authentic to them.
  2. Making lists and setting deadlines. As a small business owner, you can very easily lose your day to social media, running errands or spending too much time on irrelevant tasks. Personally, to combat this, I use lists and deadlines to help me spend my time effectively and in a way that will help me grow my coaching practice, while also giving me the freedom to get outside for walks and to connect with friends over coffee.
  3. Tracking my time. When I first started my business, I was anti-tracking my time. As a former accountant who had to bill by the quarter-hour, I had a visceral reaction to the thought of it. However, within the past year, I’ve started using a tracking tool which makes the practice pretty easy, and I was shocked to learn how much time I spent doing back-office stuff like sending emails, engaging on social media and creating new content. And — I had no idea that I spent nearly five hours reviewing new client assessment results and prepping for their initial debrief. Five hours! I had only factored two into my advertised rate. Time tracking has helped me set boundaries around my work, free up more time in my day, and own my worth by unapologetically adjusting my rates to better reflect the actual time I dedicate to my client’s growth.

This will be intuitive to you but it will be helpful to spell this out directly. Can you help explain a few reasons why it is so important to create good habits? Can you share a story or give some examples?

Sure. When it comes to habits, I typically default to explaining what I learned from Sandro Formica, PhD, in a Resiliency Workshop. In this workshop, Formica explained that we only live 5% of our lives in a state of consciousness, which means 95% of our day, including our thoughts, emotions, and behaviors, is operated from the subconscious, or auto pilot. From my understanding, this is a survival function, because once upon a time, humans were hunters and gatherers, and needed that 5% to be aware of danger. The brain had to differentiate between tasks that could be operated without thought, like walking, and tasks that needed their full attention like running away from saber tooth tigers.

And, while saber tooth tigers are no longer a threat, think of everything in your life that is on autopilot right now, including brushing your teeth, checking your phone before getting out of bed, mindlessly scrolling through your social media, your commute to work, making coffee, responding with “I’m fine,” when asked how you are, and so much more. Most days are a direct repeat of the day before, with small nuances to separate the differences, but typically nothing extravagant enough to help you truly mark the passage of time. Autopilot, or mindless habits, often cause us to disconnect from the task at hand, lose track of time, delay taking positive action towards a goal, and wake up one day and ask ourselves “where has my life gone?”

Because we live on auto pilot, it is crucial to take the time and effort to start making conscious choices about our behaviors, thoughts, and emotions, and create habits that support the life we wish to live.

Speaking in general, what is the best way to develop good habits? Conversely, how can one stop bad habits?

It is all about baby steps. Just try to be a little bit better every day and have a system that helps hold you accountable to, and rewards you for, the new behaviors you wish to create. Don’t overcomplicate it and incorporate your new behaviors into a routine that already works for you.

Success can be broken down into three parts:

  1. Awareness: What are the thoughts, behaviors, or emotions that you wish to change or create? Why is it important to you to create this new habit? How will the new habit help you align to your core values or leverage your strengths? If you are changing a habit, what additional awareness do you need about the old habit, including what triggers it?
  2. Strategy: Once you have the awareness, you can create your strategy. I always recommend working new behaviors into systems and routines that you already have in place. This model helps you slowly adapt and build, leading to sustainable results and behaviors.
  3. Mindset: Change isn’t easy. You have years and years of practice doing things your “old” way. Reframe negative thoughts and develop a resilient “I got this!” mindset when things get tough. Give yourself space and grace and keep practicing. In time, the new habits, the new thoughts, behaviors, and emotions will become easier, and before you know it — they will become your new autopilot… an autopilot that allows you to live the life you wish to create.

Recently, one of my clients wanted to stop bringing work home with her, it was draining her energy and preventing her from accepting new clients and growing her business. As a physical therapist, she was using all 60 minutes with her patients for hands-on exercises, skipping the heat and the ice at the beginning and end of sessions. She keeps all her patient notes in a notebook and transfers them to the computer at home. During our session, she decided that she wanted to start ‘winding’ her clients down around the 50-minute mark so that she had time to transfer session notes into the computer and email them any take-home exercise notes before they left. To start building this new habit, she decided to put a smiley face sticker in her patient note book every time she succeeded! Some days are better than others, but when she starts to get frustrated, she can now look at her notebook, see the smiley face stickers and remember the positive emotions she felt when she succeeded.

Can you share your favorite “Life Lesson Quote”? Why does that resonate with you so much?

“The best way to predict your future is to create it.” — Attributed to Abraham Lincoln

This quote has been visibly on display by my desk since college. It is what kept me going those late nights studying in college as an accounting major, the days I spent in corporate staring out the window calculating what my next move would be, and finally when I decided to take the leap to start my own business.

This quote, at its essence, reminds us that we have the choice to create our future. So even if the present moment isn’t “great” it doesn’t mean that we can’t live greatly tomorrow. Our past and our present are only pieces of the puzzle, and if they do not fit into the life we want to create, then it’s up to us — and only us — to do something about it.

What are some of the most interesting or exciting projects you are working on now? How do you think that might help people?

As an avid hiker and outdoor enthusiast, I was fortunate enough to spend a few months on the west coast last year. During that time, I spent a lot of time hidden in the woods and writing and reflecting on all the lessons that nature has taught me — and how realizing how seamlessly they transition into the lessons I’ve had to learn throughout life and a business owner. Over the next year or so I plan to immerse myself further into nature and this experience, with the goal of writing a book in the end that inspires people to look at their life through a different lens, embrace their strength and resiliency, and of course, spend more time in nature to learn some of these lessons themselves.

I am also in the early stages of creating self-paced courses that will empower people and small business owners to implement my success formula and break free from whatever is holding them back from reaching their full potential. This space is new to me, but I am excited to see how the final product manifests itself! I’m assuming it will be multi-faceted to accommodate the needs of my three main types of clients: women small business owners and soloprenuers, women who are considering a career transition, and women who feel like they aren’t living up to their potential and are ready to unleash their inner power.

Ok super. Here is the main question of our interview. Many coaches are successful, but some are not very successful. From your experience or perspective, what are the main factors that distinguish successful coaches from unsuccessful ones? What are your “Five Things You Need To Create a Highly Successful Career As a Life or Business Coach”? If you can, please share a story or an example for each.

In my opinion, successful coaches all have one thing in common. They are 100% unapologetically themselves. The best coaches are coaches who walk the talk and are there to strategically partner with their clients to help them creatively find their own solutions. So, to be a great coach, you must know yourself, and be yourself. That’s it!

But, what does that actually mean, and how do you do that? Here is how:

  1. Get really clear in your definition of success. Similar to the work we do with our clients, we need to be incredibly clear in what we want out of our business. Once you have that, it becomes a lot easier to make decisions and taking actionable steps forward.
  2. Know your core values and guiding principles. These will help you stand in your authenticity and make confident decisions about how you run your coaching practice.
  3. Awareness is everything. In addition to your values, be aware of your strengths, your saboteurs, limiting beliefs and external barriers to success. Once you’ ae aware of what these are, stay mindful to how they are showing up when you are working with your clients, marketing your business, or evaluating external coaching opportunities.
  4. Authenticity is best. Your clients 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 session.
  5. Work with a certified coach. Chances are, you are a coach because you believe in the power of coaching. Why not let that same power help you? Work with an ICF Accredited Coach that can partner with you to help you find your own answers, stay accountable to your goals, and trust the process.

What are the most common mistakes you have seen coaches make when they start their business? What can be done to avoid those errors?

  1. Trying to do build a business someone else’s way. This comes back to my tips above. There is no one way to grow a business, and no one else knows your unique strengths or gifts, so get really clear in your definition of success and work with a coach who will empower you to grow your business in a way that is authentic to you!
  2. Not owning their worth. This manifests in many ways, but most commonly: undercharging, undervaluing how they have helped their clients, not asking for referrals, not marketing themselves, downplaying success, and so much more. Coming back to the success formula that I use personally and with my clients — raise awareness to where you are undervaluing yourself and how it’s impacting your business, create a strategy that will help you change these behaviors or mindsets, and adopt the resilient mindset to stand confidently in your authentic power.
  3. Trying to do it all alone. Yes, being a small business owner requires you to wear multiple hats, and often money is thin in the beginning, but — that doesn’t mean you have to do it alone. There are multiple free tools that can help take some of the administrative work off your plate, and you also have a community of people behind you rooting for your success. Ask for help if you need it. From your loved ones, friends, families, other coaches, your community on social media. If you don’t feel like you have anyone in your corner? Reach out to me. Whether or not you ever choose to hire me, if you are in my network, I promise to have your back, help you celebrate your wins, and build you up when you need it most.
  4. Not getting certified. Coaching is an unregulated industry, so technically you don’t need a certification, but if you truly believe in yourself and the power of coaching, and you want to step into a role that will help you empower others, with confidence, make the investment and enroll in an ICF accredited coaching program. This will open so many doors for you in the end.

Based on your experience and success, what are a few of the most important things a coach should know in order to create a Wow! Customer Experience? Please share a story or an example for each.

  1. BE YOURSELF! Period end of story. You want to provide an amazing experience? Just be yourself. Own your worth and show up — with confidence — knowing that they have chosen you to help them on their journey.
  2. Provide value — always. There may be other business owners or coaches out there that cringe when I say this, but my number one goal is NOT to make the sale or convert clients. My number one goal, and the driving force behind my business is empowering and inspiring people to unleash their power and live greatly. Do I want people to hire me as their coach? Absolutely. But that is not my number one goal. I might not be the best fit for them, and if I’m so focused on the sale, then I’ll miss the opportunity to provide value or empower them in another way. There have been plenty of people in my community who have told me that my free content has changed their life, and they have never enrolled in one of my programs. It lights my soul on fire to know that I have had a profound impact on people I’ve never even met, it’s what encourages me to keep going, and often — it is individuals like these that support me the most when I need to reach out to my community and ask for feedback, help or referrals.

Lead generation is one of the most important aspects of any business, and particularly in coaching. What are the best ways for a coach to find customers? Can you share some of the strategies you use to generate good, qualified leads?

I am going to fall back on the authenticity thing I mentioned earlier. Personally, so my best leads come from speaking engagements and the relationships I have built through social media. But I have clients that would run for the hills if I told them they had to get up on stage, and others who don’t want to leverage social media — and that’s okay!

So, my advice here is to:

  1. Understand how you authentically connect with people.
  2. Learn where your ideal client congregates in both person and online.
  3. Start attending or joining those groups or events and just be you. Rather than selling, come from a place of curiosity. How can you support them? What value can you provide? What are their challenges, and how can you connect them to a solution, even if that solution isn’t hiring you?

Coaches are similar to startup founders who often work extremely long hours and it’s easy to end up burning the candle at both ends. What would you recommend to your fellow coaches about how to best take care of their physical and mental wellness when starting their business?

Track your time, set boundaries, and protect your energy. I work with a lot of small business owners and soloprenuers and these three things surface time and time again.

Tracking your time is crucial to helping you understand where and how you are spending your time. It is amazing how a quick email can take you 45 minutes, or an Instagram reel can take over an hour. Additionally, if you are not aware of how much time you’re spending on client-facing things, like reviewing assessment results, prepping for meetings, follow up emails, etc., you’re likely not charging appropriately for your time.

Boundaries are also crucial. Around your time, values, energy, and worth. It is easy to get caught up going out to lunch or running errands and not spending time working on your business. It is also easy to get caught up in the grind and forget to do things like go out to lunch with your friends or take time to play with your kids. And don’t get me started about scope creep! If your sessions are advertised for 60 minutes, cap them at 60 minutes. People won’t value your worth or your time if you don’t set the boundary and do the same.

Personally, my calendar is only “bookable” on select days. There are times that I will coach outside of those designated windows, but that is on my terms. I also put everything on my calendar, work meetings, work tasks, personal appointments, personal responsibilities, appointments for my dog, and down time. My calendar holds me accountable to getting stuff done, but it also keeps me from overbooking or extending myself.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I am so incredibly tired of societal norms and expectations. As a coach for mainly women, I see how many hurdles they must overcome — most in the name of societal norms. Whether it is perfectly timing a career transition around family planning, being sidelined for promotions because they are of childbearing age, unable to leave their corporate career and start a business because they need health insurance, feeling the need to ask permission before doing something because it is ‘polite,’ constantly at wars with their bodies, comparing themselves to others, and overthinking everything…. it is exhausting!

I would love to start a movement where people are empowered to make their own decisions. To create a world where people are not questioned, judged, or criticized for their decisions, life choices, faith, sexuality, race, careers, or anything else, but rather encouraged to explore what is best for them, supported with love and kindness, and given a safe space to be themselves.

We are blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

Brene Brown. Her work has been pivotal in my journey. Her documentary on Netflix is what gave me the courage to take the leap, trust myself and my vision, and quit my corporate career. Her books and podcasts continue to blow my mind and her work has been fully incorporated into my coaching practice and the work I do with my clients. That said, I know she’s a huge introvert, and I’d be star struck, so if I could just have the opportunity to say “Thank You” and shake her hand, that would be enough.

How can our readers further follow your work online?

I’m most active on Instagram @conshycoaching, but you can also follow me on LinkedIn, or visit my website at www.conshycoaching.com for access to my blog, podcast, and other free resources.

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!

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