Conni Medina of Clarity Consulting: How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur

by Charles Purdom

Being a founder, entrepreneur, or a business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur  we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Conni Medina.

Conni Medina is President and CEO of Clarity Consulting (, a performance coaching company with a mission to instill hope and enable success for striving professionals. Conni’s signature strength is being a “devoted big sister” to clients, sharing meaningful insights, practical guidance, and a deep devotion to their success. As a 20-year veteran of education and learning and former top executive for an education corporation, Conni honed her vision to help professionals see and create a hopeful future.


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 how you got started?

Conni Medina: Thank you for inviting me to be a part of this platform and share my experiences.  I have always been driven by what’s possible.  Every step in my career–through communications, education, training, product development, strategy, and innovation–reflects possibilities and potential.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

Conni Medina: After 7 years as a senior executive, I had learned a lot about business leadership, everything from restructuring to P&Ls and from data management to sales and marketing alignment.  The growth and learning was rewarding.  At the same time, I felt further and further from what I loved to do: guiding others to realize their potential.

In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?

Conni Medina: I didn’t see myself as a natural-born entrepreneur.  I’m a bit of a caretaker, and I’ve always protected myself from the financial challenges I saw my mother endure during my childhood.  A career with a responsible company and a steady paycheck seemed like the solution.  I earned my first paycheck when I was 13 (delivering newspapers) and never looked back.  When I thought about starting my business in 2019, the idea at first seemed crazy.  Why would I choose to put myself in a position of uncertainty?  In the end, my desire to get back to what truly matters to me won out. And, I realized that my resiliency, problem-solving, and unshakeable drive would serve me well as an entrepreneur

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

Conni Medina: One of my friends had left corporate and started her marketing consultancy about a year before me.  It was fascinating to see her make the change and hear about the ups and downs of her journey.  When I began to consider the same move to entrepreneurship, she was the first person I called.  She gave me great, honest advice.  After my first year in business, I hired her to lead a branding project for my company, which helped propel business growth.

What do you think makes your company stand out? Can you share a story?

Conni Medina: There are a lot of coaching businesses.  Mine is a boutique coaching company for entrepreneurs and executives in smaller companies.  They want a sounding board, strategies that work, and a reliable partner to help them get the outcomes they seek.  I like to say that no one is more devoted to clients’ success.

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?

Conni Medina:

Commitment.  I like to say that achievement doesn’t happen by accident.  I’ve known many leaders who are full of ideas and lack the focus and commitment to execute on them.  As a leader or business owner, setting an example of commitment is key.  And as an entrepreneur, you don’t have a choice!  You have to keep yourself committed.  My success is based on years of (mostly consistent!) commitment to smaller habits and actions or breaking down big goals and ideas into smaller, actionable steps.

Empathy.  As a new leader, I had a lot to learn here.  My overachiever’s high expectations for myself and my team (and even distant co-workers) didn’t serve me or my team members well.  It was a few years before I understood how much distance I was putting between myself and others.  Over time, I saw the value of slowing down and getting to know my team members on a personal level.  Learning to lead with empathy when others felt overwhelmed, frustrated, or uncertain made a huge difference for me and my team.

Optimism.  To me, this is more than just looking at the glass half full.  It’s about seeing what’s possible and also believing you have a plan to get there and the agency to make it happen.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

Conni Medina: When I started out in my business, some people told me not to do any work for free, that it would only devalue my expertise.  I eventually chose to offer a few small pro bono projects, which were great ways to get testimonials, social proof, and a network of advocates.  These projects also helped me test a few services.  I wish I’d done these sooner!

Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?

Conni Medina: Most importantly, make it okay to talk about.  And, help the leaders model self-care.  When people see and hear how others (leaders especially) respond, it sets the pace.

What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?

Conni Medina: Listen more.  When you speak or write, help people see things in a new way.  Building authority isn’t about giving advice or telling all about your expertise.  Over the years, and especially in my coaching work, I’ve found great value in asking great questions.  First, it shows the other person, they are capable.  Second, it shows a desire to hear their ideas and perspectives.  When a colleague or client says, “That’s a great question.  I hadn’t thought about it that way before,” I know we’re stepping into a new level of trust.

Can you help articulate why doing that is essential today?

Conni Medina: People crave community and connection.  They don’t want to be receivers of expert information from a distant source.  They want to be understood and heard.  And, most importantly, they want to be valued.  Leaders who can achieve this have built trust, credibility, and an authentic authority.  They build loyal, innovative teams that make an impact in their industries.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

Conni Medina: I’ve seen three common mistakes.  First, they don’t have a business plan.  It’s easy to assume that a business plan has to be long and complicated.  But it doesn’t have to be.  And there’s more value in having a simple, high-level plan that keeps you and your team focused than having no plan at all.

Second, they miss out on key marketing guidance. They skip the branding and strategy and go for the tactical.  Defining your brand lays a
foundation for everything else you do in marketing.

Third, they try to do it alone.  As business owners, we may feel that we must have all the answers.  The truth is we don’t!  As our organizations grow, we will add skills, experience, and expertise that we lack.  Why not bring in fractional or project-based expertise that will add value and grow our business

Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?

Conni Medina: A “regular job” tends to have more predictability…in working hours, regular activities, team members or coworkers, and compensation.  As an entrepreneur, there is much less predictability–especially in the beginning.  One day you’re excited about big ideas and strategy, and the next you’re problem-solving a computer crash.  One day you land a major client project, and then the next five opportunities go nowhere.

Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.

Conni Medina: Yes!  There are some great highs to celebrate.  The most recent was a string of 5 business days when I discovered 8 new business opportunities, booked a client in a single call, confirmed a major speaking engagement, and secured a new referral partner.  Everything seemed to fall into place with ease.  My husband gently reminded me that none of these things happened out of nowhere: they came from weeks and months of small activities that happened to add up just right during those few days.

Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.

Conni Medina: There was a really tough month in 2020 when the pandemic had just hit.  Most of my new client opportunities had been postponed indefinitely or cancelled.  The pipeline I built had disappeared.  That same month my college student daughter received two COVID relief checks while she logged into virtual classes from our guest bedroom and enjoyed home-cooked meals.  That was demoralizing.

Based on your experience can you tell us what you did to bounce back?

Conni Medina: Well I wouldn’t call it bouncing back!  The pandemic amplified one of the biggest lessons of entrepreneurship: there are no guarantees, so you have to be willing to keep going.  When my pipeline disappeared, I simply chose to get up each day and keep working my marketing and sales activities.  I chose to believe in the impact I make for my clients.  And I was willing to respond to changes in my clients’ work and business to keep moving forward.  Within weeks, that tough time had passed and business starting picking up.

Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.

Conni Medina:

Get expert help.  You won’t (and can’t) have all the answers.  Don’t fall into the trap of believing you must know everything if you’re the business owner.  It’s a recipe for stress and self-doubt.  Know the expertise you lack and seek it out.  After almost 15 years of developing and launching new products, I thought I had what it takes to do the same for my business.  I was wrong.  After my first year, I knew I wasn’t 100% clear on my services, my ideal clients, and my “why.”  And this gap was affecting my confidence and business growth.  So I hired a marketing expert in making brands memorable to help define my brand identity.  This was a big turning point for me and my business.  Since then, I am more confident in business development, and my business has grown more steadily.

Get sleep.  Your brain will thank you.  When you’re tired, you are less able to respond to challenges, make tough decisions, and deal with disappointment.  So make sleep a priority.  As a busy executive, with an events and travel schedule, I rarely got enough sleep and often felt exhausted, overwhelmed, and unable to respond well to challenges.  Now as an entrepreneur I sleep more than I ever have in my career, and my concentration and decision making are much better.

Stay active.  Your body needs movement and time away from your laptop. You don’t need to be up at 5am doing an hour-long Olympic-level workout.  Find the activities and timing that work for you.  I work out most days, preferably in the morning because I feel more productive the rest of the day.  When my concentration starts to fade in the afternoon, I know it’s time for a walk outside.  And when I’m evaluating a big decision or in need of a creative solution, I always find my best mental clarity on a run.

Manage your decision making.  As an entrepreneur, you face tough decisions.  And you may feel exhausted by the volume of decisions.  With the pressures of entrepreneurship, emotions can cloud your judgment.  So, take the pressure off and put some structure into your business.  Manage your decision-making with a tool that works for you.  Early in my business, every decision seemed to be a unique thought process, making the time to solve longer.  To complicate things, on days when I felt down or tired, I wasn’t in the best frame of mind to evaluate.  So I defined my decision-making process, which relies on my vision, mission, and values.  Now I make decisions more easily, more quickly, and with greater confidence.

Find your support team. You can’t do it alone. And, as your business goes through incredible highs and really tough lows, it is helpful to have people around you who provide steady support.  For me, my support team includes my husband and kids and a handful of friends who are rooting for me no matter what.  On days when I’m celebrating wins (even the smallest ones) their joy and pride is an extra boost.  And on days when nothing seems to be coming together, their steady belief and encouragement of “You’re doing great.  Keep going.” mean the world to me.

We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

Conni Medina: Resilience is about bouncing back from challenges.  People who face challenges frequently (such as entrepreneurs) must be resilient over and over again.  To me, the key characteristic is being hopeful.  Hope is about seeing what’s possible and knowing how to (and believing you can) make it happen.

Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?

Conni Medina: Growing up as the older of two girls with a single mom taught me a lot about resiliency!  When I was young, we didn’t have a lot of furniture, and we wore hand-me-down clothes.  I missed out on some school activities because we couldn’t afford them.  And, I watched as my mom endured bankruptcy.  She doesn’t know that I used to sneak money from my small allowance into her manila cash folder to try to help pay the bills.  Despite all this, I never remember feeling hopeless.  We grew up building resiliency every week, always finding a way forward.  And I share this with great appreciation for the value it has brought me.

In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?

Conni Medina: As an entrepreneur, I’ve had times of intense frustration or disappointment–even hopelessness.  A walk or run and definitely a good night’s sleep help me to think more productively.  When times are tough, I think about the best advice my mom ever gave me: There’s nowhere to go but through.  Her experience as a single mother taught her that tough times never last, and when we turn our attention to what’s possible, we’re more likely to move forward.

Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.

Conni Medina: I believe where a leader goes the team (and clients) tend to follow.  And I think there’s more to it than just being positive.  It’s also about being productive when faced with challenges.  So, a leader with a positive and productive attitude is more likely to develop a team that can respond well to challenges and opportunities.  The same goes for client relationships.  When clients are upset or frustrated, a positive and productive response (instead of dismissive or blaming) is key.  Together, these can solve problems and, more importantly, deepen the relationships.

Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?

Conni Medina: Eleanor Roosevelt had a simple, straightforward message that means a lot to me: “You must do the thing you think you cannot do.”  I thought about this quote often as I thought about launching my business.  Was I afraid?  Yes.  Did I have doubts?  Yes.  After two decades in education and learning, I knew that growth comes through new and challenging experiences, not repeating what’s familiar.  And I knew from mentoring others that confidence was built on accomplishing something difficult, not living in your comfort zone.  So, I faced those fears and made the leap to entrepreneurship.

How can our readers further follow you online?

Conni Medina:

Connect with me on LinkedIn (Conni Medina), 

Instagram @claritycoach_conni, or Facebook (Clarity Consulting).  

Or visit our website

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

Conni Medina:Thank you!

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