BY: Cherry Maggorie – “The Freak of Nurture”


Chapter 14: Being a Boss at the Border of Crazy

During the summer of 2009, I found myself sitting in the lobby of one of the most famous buildings in NYC, possibly the world.   I look up and see decades of famous faces staring back at me. It is truly humbling to even walk into this building as a tourist, let alone a potential future employee.

On top of that, I’m almost seven months pregnant and utterly exhausted.  On my way here, I walked through the city in the pouring rain, and my dress, shoes, and legs were soaked.  My hair was a frizzy mess, and my belly was aching. Adding insult to injury, I nearly slipped on the marble floor of the lobby.   What the fuck? Can it get any worse?

After making my way through security, I headed up to the office of the President of one of the company’s Television networks.   This is my final interview for a VP of Marketing position. It was an opportunity I always dreamed of but never, ever thought I’d get the chance to fulfill.

It felt like everything was working against me, starting with the fact that I didn’t have TV experience.  What was working for me, was that the executive that recommended me for the job was bullish on my hire. Conversely, the President I was meeting with, was NOT.  Not to mention, they would have to hire me seven months pregnant and then I’d be going on maternity leave shortly after I started the job. Remember, it’s 2009 and about 10 years before the #metoo movement, and I’m thinking that hiring a pregnant woman was not the top of anyone’s list.

Thankfully, I had a solid history of performance with the leader who recommended me for this position from our work together at Time Inc.  She was now the COO of the network, leading the marketing and sales division. She was a legend in the business and successfully made the transition from publishing to TV.   She wants me to partner with her to elevate the marketing capabilities of the network to become a revenue-driving division. She, like me, believes that ideas and creativity, when executed well, lead to increased investment by marketing partners.  

But here I stand, all 5’3” of me with my pregnant body as wide as I am tall, looking up at photo after photo of entertainment and cultural legends.  My inner self-saboteur starts to invade my mind with so many questions…What right do I have to be here? Do I really belong? Am I good enough?

After about 10 minutes (I was early, he was precisely on time), the President calls me in.  My heart jumps into my throat, and I suddenly lost my breath.  I struggle to stand and have to scoot to the end of the couch to pull myself into a standing position.  His assistant offers me water, and I follow slowly behind her, waddling into his office. As he stands up to greet me, I am just completely overwhelmed.

His long legs push his chair back from his desk, and he slowly climbs to his full height.  He is 6’5” with a full head of silver hair and piercing turquoise blue eyes. He is striking in every single way.  His energy is kingly; a super-alpha, with a gentle intelligence that is utterly disarming and counterintuitive to his stature.  I am mesmerized.

I reach out to shake his hand with the firmest, strongest handshake I could muster, as I introduce myself.  He makes eye contact and holds onto my hand as his eyes penetrate my soul. I felt like he was scanning me to figure out my intentions and if I was an honest person.

Before being named President of this network, he was a journalist for many years.  His credentials were incredible. I had done my research, and I was already intimidated walking into the meeting.  Now with his immense energy filling the room, I know I am in for one of the toughest interviews of my life.

The interview started off with the usual pleasantries.  He was warm and welcoming; a pleasant surprise considering my first impression.  He begins the style of questioning that undoubtedly led to his success as a journalist; starting off gently as he builds toward the tougher questions.  

Throughout the interview, we talked about my strengths and vision for the role and where my challenges would lie.  I asked him a ton of questions about his expectations, hopes for the team and the kind of leader he wanted.

After about an hour of deep philosophical conversation, and some good belly laughs, we get to his final question.  He looks very seriously at me and says, “This is the question I always leave until the end, but it is the most important.  This is the question that will tell me the most about who you are. Are you ready?” I gulp and respond, “Yes, of course!” And then he pops the question, “What is the one thing in your life that is both your biggest regret and your greatest success?”

Well, of course, I am in sheer panic as my armpits begin to sweat profusely and my face turns red! This is a trap question!  No matter what I tell him, it has to be the truth because this man could see through the bullshit in an instant. This is a question that will reveal the worst of me which was the catalyst to the best of me.  I feel like I’m sitting there naked. Completely exposed.

The first thing that pops into my head is my most embarrassing, my most shameful truth…but I know this is my biggest regret that propelled my career.  It is the truth that I never openly shared. It’s the truth that drove me to work harder, smarter and effort more than anyone else; it’s what prompted me to become a workaholic.

I muster all my courage and bravely, for the first time in my career, share my secret…

I respond, “Well, that is a really tough question because answering honestly might be the reason I lose this job.  However, I have to take the chance because this is my truth. My biggest regret is that I didn’t graduate from college.  I went for two and a half years, but never got a degree. Due to personal difficulties, I quit school and decided to go to work full time.  I’ve always been a hard worker, I started working when I was 13 while I attended school. While I was a smart student, I didn’t thrive in the lecture style of college, and I was a terrible test taker.  I realize now that I learned differently than other people. When I entered the workforce without a degree, I decided to work hard, work smart, to be the best at anything I put my mind to and to be an open-minded and intuitive leader. To look at someone’s capabilities and attitude versus their college credentials.   It is my one regret that has been the biggest catalyst for my success. It is the reason I am here with you today.”

He watched me intently and showed literally no outward emotion or response to what I was saying.  After a long pause, he said “Thank you for being honest with me. You did take a great risk sharing that with me.  But your risk will pay off…because I didn’t graduate college either. I, like you, have always worked hard, grew up on the wrong side of the tracks, a complete rebel and tough guy until I found what I loved to do.  No one worked harder than me. I had street smarts with strong emotional intelligence. I had a unique ability to connect with people, and that is why I am sitting in front of YOU today.”

Well, needless to say, I was stunned.  My anxiety turned to joy, and I knew at this moment we connected on an entirely different level.  We found a kindred spirit who thrived through life’s many trials and tribulations. We both succeeded despite the odds against us.  It was the thing that ultimately landed me the job. While he is not, I am still at the company for over nine years.

How ironic…with all the odds against me, the tipping point was my honest answer to his toughest question.  This was the moment that taught me the most significant lesson about leadership and humanity.

This moment is branded in my mind, as it is the one time in my life that my greatest weakness became my strength.  I met a leader with the guts and wherewithal to see my true self, and my character shine through and that inspired him to give me a shot.  It proved that more than any college degree, authenticity, hard work, emotional intelligence, and just sheer honesty pays off. I was lucky.  Very, very lucky to have encountered such a leader.

After 22 years in this industry, I have met all types of leaders.  Leaders that frightened me, that challenged me, that inspired me, that taught me, that abused my work ethic, that gave me a chance, that believed in me even when I didn’t.   

Today is National Bosses Day.  So I decided to share this story with you all in hopes that you realize the immense responsibility a leader takes on.  They are a teacher, a parent at times, accountable to the business, sometimes even to the stock market. Their duties, decision-making, and exposure can be an incredible pressure cooker.  People and companies are relying upon them.

I’ve also learned that not everyone gets into business to lead.  People fall in love with a job or a career and eventually grow into leadership positions.  Leading is an entirely separate job; a distinct responsibility. Leading has the most significant impact on the bottom-line of any company and on the lives of employees.  Like children depend on their parents, people depend on leaders to successfully manage their businesses so they have jobs when they wake each day.

I have had the privilege to be in the position of “leader” from my second year in this industry.  And for a long time, I was not great at it. My “workaholism” and drive to grow was a pain in the ass to my direct reports and to my managers. Luckily, I’ve had many leaders who helped me find my way.  I’ve experienced training that gave me tools to thrive as an individual and as a manager.

And I’ve encountered wonderful, brave people who were willing to take a chance and tell me what they honestly thought about me as a leader and manager.  And I listened and learned…and now I see the fruits of my labor. There is a long roster of former direct reports which are CEO’s, Executive or Senior Vice President of major corporations, entrepreneurs, and artists, who now lead their own teams bravely, with heart and humanity.  

I was told once by a very talented employee, that there was a rumor about me she wanted to share, that I had a reputation.  My immediate thought was OH SHIT…this can’t be good (could I be more of a fatalist?).  I braced myself.  She said, “Word on the street is that you breed leaders.”  (Insert sigh of relief followed by shock and awe).

What better pay-off than to be partially credited for someone’s success. To be told that through your leadership, you’ve moved others to lead.  That you are an influential part of the story of someone’s life. What a gift. What an honor.

To pay it forward, I am making it my business to thank every leader I had the privilege to work for and alongside…to dedicate this blog to be my public THANK YOU note on National Bosses Day.  To share my heartfelt thanks to the managers, leaders and my direct reports that have made an enormous impact on my life, who left an indelible mark on my career. I am humbly and eternally grateful for your investment in me.  You know who you are!!!

I also wanted to take this opportunity to share a few leadership lessons that my current and former leaders imparted on me throughout my 22-year career, in hopes of inspiring all of you!


  • Leaders Don’t Need Titles.  Leading is not about the job or title you have but how you interact with people, take accountability, support others and drive business results.  Be the shepherd.
  • Insecurity is the bane of leadership. Yet it is pervasive in most companies, because humans lead companies.  People have years of experiences that cause their insecurity to surface at work.  For instance, while not graduating college fuelled my success, it also caused me to tax my team often pushing their limits, along with my own.  My insecurity drove me to be envious of other people’s successes. It was my weakness and my poison. Extract that poison from your life. Kill your inner saboteur and change your internal narrative. It will free you!
  • Lead Humanly.  Regardless of experience or credentials, what matters most in leadership is honesty, integrity, kindness, passion for what you do, support of others, empathy, guiding, caring and humility.
  • Bring YOU to work.  You are not one person at work and one person in the office.  Certainly, there are attributes you dial up or down based on your work environment, but when you bring the attributes that make you a good person in life to work, you will win people’s trust.  Be authentically and uniquely YOU!
  • Friendships are born at work. Let’s face it, we spend more time with our colleagues than our family and friends.  We share marriages, divorces, children, loss, health issues and so much more. Most of my best friendships were formed during the course of my career, and for that, I am very grateful.  My friends and colleagues are my witnesses, confidants, leaders, and co-conspirators. But be careful how and when you cross the line from friendly to friends. Not every person you work with wants to know about your life or party with you like its 1999.
  • Be kind to EVERYONE.  From the security guard, you pass every day, to the people who clean your office to the executive assistant of the President to your peers.  Build the tribe of people who challenge you, those you admire and those that make you laugh. They are the people who make offices run and companies succeed.  And you never know when they might be your boss or help you in a time of need.
  • Leading can be EXHAUSTING.  It is not for the weary.  You have to worry about your work, AND your teams work and their career path.  Know when to take a break and remember, no one is too powerful or important to ask for help.  Leaning on your team and sharing your vulnerability can be the difference between being seen as a leader or a boss.
  • Trust your team. Empower them. Your main job is to ask questions NOT to have the answers all the time.
  • Encourage failure.  Give them the rope to take chances but be the net to catch them and lift them up.  Support risk taking and teach them how to fail forward.
  • Never stop being a student. Approach your career with the same open mind and curiosity as you did school. Know that your team will teach YOU as much as you teach them.
  • Observe Leaders. You can learn what TO DO and what NOT TO DO from other styles of leadership. See their impact. Read their body language.  Learn how they impact the vector of a meeting and the energy of their employees. Listen to what is being said about them from peers and their team.
  • Assume Best Intentions.  Don’t take things so personally.  Never, ever forget you are dealing with human beings with complex emotions that face personal challenges that could impact their performance.
  • Use your Influence.  You can make a difference.  Sponsor young people. Mentor them.  The return on your investment will be tenfold.
  • Challenge the Status Quo.  You have the chance to impact culture, foster creativity and incite change.  Know your power and use it for good.
  • Invest in Training. For your team and yourself.  Never stop learning how to be better. One of the best examples was two years ago, I got an executive coach which included a 360 feedback survey. I learned more in six months than in the past six years.
  • Be Curious.  A Harvard study found that CQ (Curiosity Quotient) matched with EQ (Emotional Quotient) was more important in business and leadership than IQ.  
  • Bravely Ask Questions.  Don’t be afraid to admit that you don’t know the answer. Showing your vulnerability will give your team permission to do the same.  I can’t tell you how many meetings I walked out of and someone asked me to explain what the presenter was talking about. And I’m thinking to myself, why didn’t you ask in the meeting????  People fear looking silly or uninformed, and that goes back to insecurity.
  • You are Being WATCHED!  I mean it! But not in some stalker way…what I mean is that everything you do or say, and what you DON’T say is being observed.  Know that body language and tone matter to people, it actually matters more than what you say!
  • Invite Feedback.  Often! Ask people what they think of your leadership style.  Ask them to share their thoughts on your strengths and areas for improvement.  Ask your team what they need from you to succeed. Take constructive criticism and let it make you better.  If someone dares to share what they think, they intend to help you, not hurt you.
  • Know and Own Your Legacy.  And it has nothing to do with the sale you made or the business you won or the promotion you got.  All that will be forgotten a year from now. Your legacy lies with the people you affected, the lives you changed, the people you helped, the professionals you inspired to achieve their best self.  They are your legacy.
  • Say THANK YOU…to your team for their efforts, to the leaders who have inspired you or taught you something. To your parents, aunts, uncles, cousins, friends, children, colleagues, even the guy you buy coffee from every morning…to anyone who has ever spent the time listening to you or offering sage advice or taking care of something you needed.  Leaders are all around us, and they should know how much they mean to you!

And DON’T be like me and wait for National Bosses Day to do it!




Cherry Maggiore is the proud single mom of her 9-year-old super-sassy daughter (aka Miss Sassy Pants or MSP) and 15-year-old pug baby (Tiki Barber); in addition to being an award-winning senior marketing executive at NBCUniversal.

Beside her side hustle as the Freak of Nurture, she also started a home design company after being inspired by renovating and designing her 1880’s home in NJ.

This insanely curious and passionate “multi-potentialite” can be found dancing the Argentinan tango, swing and Hustle every Saturday, cooking her family an Italian Sunday dinner, singing and air drumming at concerts or searching for her next adventure.

Leave A Comment!
Share This