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Be Your Own Cheerleader

Be Your Own Cheerleader


Published March 4, 2021

Author Heather Dugan.
One of the big challenges in addressing isolation and disconnection is the inherent shame in identifying as “lonely.” It feels like a personal failure. We’d much rather share our Instagram #perfect moments. But covering it up only exacerbates that feeling of separation and will entrench the isolated individual in the very space they wish to escape. So, my first goal has been simply to remove the stigma and create conversation. Readers of The Friendship Upgrade tell me that reading the shared experiences of other women and understanding the larger societal factors that leave us vulnerable is comforting and that the actionable steps inspire choices for change.

As part of my series about “authors who are making an important social impact”, I had the pleasure of interviewing Heather Dugan, an award-winning author and speaker and founder of Cabernet Coaches®, an “all ages, all stages” group for women that fosters self-betterment through face-to-face friendships and social connection. Her books include The Friendship Upgrade: Trade Clickable Connections for Friendships that Matter and Date Like a Grownup: Anecdotes, Admissions of Guilt & Advice Between Friends. A graduate of Indiana University, Heather has independently produced and appeared in hundreds of video and voiceover projects for a wide range of national and international clients. Her articles and advice columns on business and professional relationships, travel, and health eventually led her into book publication and speaking.

Heather’s spotlight on the disconnecting factors impacting personal and professional relationships creates larger conversations on creating space for connection and building stronger communities and organizations. Her focus on fostering more meaningful relationships, facilitating effective communication, and equipping men and women for life-changing transitions makes her a popular speaker and guest expert for companies, communities, and the national media. Heather resides in Columbus, Ohio, but is an avid traveler and outdoor enthusiast who keeps hiking poles and her passport within easy reach.

Arianna Huffington of Thrive Global.

Thank you so much for joining us in this interview series! Before we dive into the main focus of our interview, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

Sure! It was a very traditional Midwestern family. I was the oldest of four girls, with a stay-at-home mom and attorney dad. There was more music than TV and a lot of “make your own fun” time. I poured a lot of energy into writing music, stories, and scripts we would then perform; creating art objects to sell at the foot of the driveway; and playing the usual backyard games. My dad’s job allowed us to travel all over the US and Canada for weeks at a time in the summer, giving me a beginner’s sense of the size and diversity or our planet. His intellectual curiosity and love of exploring instilled the same in me.

My parents certainly did their best, but looking back, Mom felt overwhelmed most of the time, and home life grew increasingly difficult. The hardest part was the pressure to remain silent, to keep “family matters” private. Over time, this unfortunate indoctrination began to isolate me from peers and impacted my approach to relationships well into adulthood.

Learning and understanding what my mom’s experience might have felt like was really helpful. My parents’ early deaths twenty years ago, while terribly difficult, created the space for me to assess and correct many of the misperceptions and tools I’d relied on to that point. It’s crazy to realize how many of our relationship rules and social constructs are absorbed from peers who are just as immature as ourselves and from parents who will absolutely miss a few things as they struggle to balance their own lives. We forge on, building on an often-crooked foundation, and then get disappointed when things feel off balance and collapse.

Digging through what I’ve described (and plenty more that followed those early years) was difficult, but I wouldn’t trade a thing. Truly. It gave me invaluable perspective, a huge appreciation for where I have landed, and a very focused desire to help others avoid or climb out of the ruts I got stuck in.

This is a great question, btw. So much of who we grow to be is threaded back to the ideas and inspirations we carry out of childhood.

When you were younger, was there a book that you read that inspired you to take action or changed your life? Can you share a story about that?

This is a difficult question for a girl who read by the library bagful! The first one that comes to mind, though, is Harriet the Spy. I don’t remember a lot of the plot line at this point, but I loved that she was curious and a writer. I identified with her feelings of being an outsider, and I hoped that I, too, might find out I was secretly special.

The book led me to immediately phone Dad after spotting a recruitment ad (FBI?), begging permission to call the number I’d jotted down. My assurance that no one would suspect an eight-year-old spy didn’t fly. It was a solid “no.” While the spy thing didn’t work out, the book encouraged me to continue observing and writing about the world around me and made me hope for bigger things within myself. Many thanks to the late Louise Fitzhugh!

Can you share the funniest or most interesting mistake that occurred to you in the course of your career? What lesson or take away did you learn from that?

File this under “interesting.” Unlike The Friendship Upgrade, my previous title, Date Like a Grownup: Anecdotes, Admissions of Guilt & Advice Between Friends, was self-published. I’d spent a couple of years on interviews and research, writing and editing, and developing the cover. Ensuring compliance with all the details necessary for it to be available in bookstores and in all the eBook formats was an exhaustive process. And then just before my first radio interview, I received a cease-and-desist letter. Unbeknownst to me, the first four words in my title had been trademarked, and the California business owner was demanding a title change and that I take down the website — not quite the launch I’d anticipated!

I tried reaching out to the owner directly and received yet another attorney letter (and another after that). There was a deadline. My choices appeared to be an expensive legal battle via the World Intellectual Property Association (WIPA) or a shutdown on my publishing project. A friend kindly pointed out a third option: to fight it myself.

I contacted a local intellectual property attorney who agreed to look over the fourteen-page legal brief I would eventually submit, and I got to work. Surprisingly, the process of researching case law and legal arguments and crafting the language was an enjoyable challenge. It was definitely better than giving up. I built a strong case that it wasn’t a distinctive phrase and gained the support of another author who had tangled with the business owner previously. There were some anxious weeks waiting on adjudication, but I won!

While writing a legal brief to defend my property was not a bucket list item, it was an important landmark. The process of pulling apart the tangled mess and assembling a plan of action was empowering. I walked away with a strong sense that, while I might not immediately have answers, I have or can access the tools and resources to solve just about anything.

I also learned the importance of protecting myself against future issues and trademarked the women’s social group I founded, Cabernet Coaches, with the help of The University of Akron Trademark Clinic!

Can you describe how you aim to make a significant social impact with your book?

An ever-growing number of us is doing life alone, and unchosen isolation — loneliness — is a key factor in many of our biggest social issues. That sense of disconnection is at the core of problems like addiction, depression, violence, and polarization, to name just a few.

Loneliness is often self-perpetuating; a temporary situation can quickly spiral into a chronic condition due to the cognitive changes that occur. This creates a trap, impacting both the individual and their larger community. Our social infrastructure has significant cracks, and we must mend them to function as a healthy society.

One of the big challenges in addressing isolation and disconnection is the inherent shame in identifying as “lonely.” It feels like a personal failure. We’d much rather share our Instagram #perfect! moments. But covering it up only exacerbates that feeling of separation and will entrench the isolated individual in the very space they wish to escape. So, my first goal has been simply to remove the stigma and create conversation. Readers of The Friendship Upgrade tell me that reading the shared experiences of other women and understanding the larger societal factors that leave us vulnerable is comforting and that the actionable steps inspire choices for change.

I’m also encouraging larger dialogue on how we got here and what we can do to weave connection back into our lives. In many cases we’ve embraced efficiency past the point of efficacy: prioritizing speed and quantity over the harder work of developing our important relationships. Easy access to data on demand has created an opportunity clutter in our brains. We have more options than we can possibly sort through, but because so many are potentially useful, we hesitate to release them, further restricting our ability to engage in the moment. Further, the increase of digital communication has stripped away the powerful social cues we used to rely on for filling information gaps. With texting, emails, and social media, we lose the context provided by facial expressions, vocal tones, and body language. We spend more time communicating but less time engaging in real conversation, and when we lack empathy, disagreements quickly grow into polarizing divisions.

Loneliness is actually a very predictable outcome after life transitions of any size given our pace of life, weakened community ties, and digital reliance. A job change, a new baby, a divorce… it doesn’t take much to land on an island, and with rusty social skills, increased stress, and a lessening of confidence over time, it’s far too easy to stay there. COVID couldn’t have come at a worse time. It’s the squeeze we didn’t need, emotionally speaking. Many will lack the wherewithal to come back out of hibernation. Communities need to prepare for this.

Can you share with us the most interesting story that you shared in your book?

While the book includes some of my own pivotal moments, the stories shared in the interviews were simply riveting. I just wish I could have included more of them (my editor was wonderful but brutal)! Most of the sessions took place in my home — very relaxed, conversational, and vulnerable. I pulled out a tissue box many times, for both painful memories and happy tears. One woman recounted family life with an undercover cop and how all that secrecy and turmoil impacted her ability to connect as an adult. Others shared deeply imbedded memories of how friends had saved and failed them.

The dramatic story of a woman suddenly transplanted from rural Ohio into downtown LA as a teen is maybe the most inspiring because of the exceptional “before and after” contrast. After many challenging and often miserable years that included abandonment, teen pregnancy, betrayals, abuse, failed marriages, poverty, and sheer and utter loneliness, she finally landed in a truly happy life. I won’t divulge the whole journey, but her joy today is infectious and infused with gratitude.

Her pivotal change came with dialing down her hunt for a life partner in favor of investing time and energy into building friendships. This wasn’t an abandonment of romantic hopes but a priority flip that expanded her appreciation for who she could be as a single woman first. She realized she needed “relationship” more than she needed “a relationship,” and it changed her life.

What was the “aha moment” or series of events that made you decide to bring your message to the greater world? Can you share a story about that?

I had a front row seat to sooo many personal transformations within the Cabernet Coaches group. Quick note: the name was an alliterative choice based on our (pre-COVID) weekly meetings at budget-friendly happy hours. Our activities are wide-ranging, and several members prefer plain tea or water. With lemon, please.

The group expanded quickly as women brought acquaintances, men referred female friends, and community awareness grew. It was thrilling to witness so many women thriving and growing in new directions — starting businesses and going for promotions, breaking bad patterns and releasing toxic relationships, trying new activities and making better personal decisions — simply because they had a foundation of friends to encourage and back them up! It seemed such a simply fix: creating a community access point for friendship discovery and development. And being me, I wanted to understand what was working and why. I already had hopes it might be replicated in other communities.

In late 2014, the man I was dating told me this should be my next book. I couldn’t grasp what he meant at first but let it roll around in my brain while continuing to look at the early research on isolation and loneliness (the cognitive effects and its impact on emotional and physical health).

In my years as a writer, I’ve covered business, health, travel, and written a couple of advice columns. His comment reminded me of how often readers and video viewers shared or alluded to an underlying loneliness in their messages: surgical patients dreading a long recovery, single men and women stuck in a pattern of failed romance, even office workers seeking a better team connection with co-workers. Loneliness was clearly a diminishing force in too many lives. Developing what I was learning and observing into a book soon seemed imperative.

With all the societal forces at play, most of us are but a transition or two away from disconnection. It happens to perfectly wonderful people all the time. It’s a waste of valuable lives and just a terrible way to live.

Without sharing specific names, can you tell us a story about a particular individual who was impacted or helped by your cause?

I once received a message from the son of a Cabernet Coaches group member. He’d worried over her growing depression after a family need necessitated a move to our area, completely uprooting her from a life and friend network she’d built over decades.

“This group made all the difference. It got her back into life again, rebuilt her confidence, and helped her find a new direction. Thank you.” His heartfelt words underscore that, while we may struggle alone, the negative impact of disconnection stretches into families, the workplace, and the larger community. The individual loses the capacity to enjoy a productive and fulfilling life, and the social circles around them lose that person’s best contributions, possibly contending with the proven negative health effects as well.

Are there three things the community/society/politicians can do to help you address the root of the problem you are trying to solve?

1) Collaborate. Disconnection is at the root of so many of our headline issues. This is one place where working together could yield exponential results in multiple directions. While homelessness, suicide, addiction, and domestic violence (for instance) require timely and direct action, if organizations, politicians, and community leaders could also pool talent and resources to address isolation in their community, they could collectively narrow the channels through which individuals land in these crises.

2) Foster community dialogue and education. People don’t typically raise their hand and say, “Hey, I’m lonely. I don’t feel understood or connected to the people around me.” It feels shameful. They hide the hurt, but it reemerges in increasingly negative ways. When given opportunity, people are so relieved to talk about this, to know they aren’t the only one experiencing these feelings! Group discussion can be powerful, because once the issue is out in the open, we can take first steps toward reconnecting or begin identifying the people in our lives who might need a helping hand.

Educating people on why disconnection happens (that it isn’t a personal failing) and how widespread the problem is (more than half of us lack meaningful conversations) lifts shame and raises hope. Communities and companies need to reassure residents and employees with this kind of information.

3) Establish better channels for connection. We form most relationships through proximity. Our paths cross, and we discover a common interest or that “click” of compatibility. Over the past thirty years or so, however, we’re been less available to these serendipitous moments as we’re texting, checking a news feed, and multi-tasking our way through life. Digital distractions, busier lifestyles, and less connected communities have all contributed, but we also experience a narrowing of opportunity as we settle into adulthood. For many, the pandemic simply spotlighted an existing social gap they hadn’t the time or energy to notice previously.

As we emerge from COVID, some will race back into all things social, but others will be reluctant or immobile due to the long-term consequences of disconnection. People will also struggle against the habits built with pandemic life, averting their eyes and avoiding social contact, and opting for digital connections or Netflix over real-life opportunities. Our social skills are weaker.

It will be important to create easy proximity opportunities, to even incentivize community gatherings in some cases. Some will need assurance that it’s fine to attend an event solo. Communities and businesses in work from home mode need to recognize our inherent need for connection and give people excuses to gather and rediscover what it even feels like.

How do you define “Leadership”? Can you explain what you mean or give an example?

Leaders are focused gap-fillers, identifying problems and possibilities and then formulating effective solutions and innovations to meet the need or opportunity. The best leaders channel a bigger sense of purpose that allows them to shoulder responsibility while retaining an essential openness to ideas potentially better than their own. They encourage creative thought, see failure as a source of information, and understand that, with few exceptions, strategic collaboration facilitates superior results. Great leaders are more concerned about liking themselves than the opinions of others.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or example for each.

1) Absorb Life. I spent a lot of early years tiptoeing around pain and potential failure. Avoiding tough feelings and situations can be more about fearing our capacity to handle something than the thing itself. Once you face down that underlying component, the whole world opens up in wonderful ways. Instead of having to be brave, you can just be curious. Life should be a “no waste” experience. Goals are important but not at the expense of all we can learn from the people, conversations, and random moments along the way. Untying value from outcome removes pressure, elevates appreciation, and facilitates the repurposing of negative events.

2) Be your own cheerleader. It’s disturbing how much easier our hearts grab onto a negative comment over a positive one, and our own voices can be the worst of all! After several years of battling my own heckling, I vowed to never say anything to myself that I wouldn’t speak to one of my kids. That’ll change your language! I also realized that, if I needed encouragement, I’d better be prepared to supply it to myself. That voice in your head had better be your ally, otherwise you’re essentially trash-talking the home team.

3) Embrace Plan B. Be flexible, or you might miss something better. Original plans are inherently limited by our own imaginations. A roadblock is often the vantage point to a broader viewpoint and more accurate perspective. My whole career has been a rolling Plan B. I actually about halfway through the alphabet. It’s been a very active steering process as I’ve gained skills, confidence, and experience. Plan Bs can take us to better places than we are capable of dreaming for ourselves.

Most of my travel experiences have also required many Plan Bs. My kids and I were once stranded on a Caribbean island after the ferry broke down. The experiences of connecting with some terrific similarly stranded people, finding and securing passage on a teensy little plane, and then flying as co-pilot — all of this was far more interesting, fun, and memorable than my boring little idea of returning the same way we’d arrived.

4) Make original mistakes. Our future depends on continually developing new ideas. Having been failure-avoidant myself, I encouraged my kids to run full tilt at their dreams, and to (respectfully) push against arbitrary limits imposed by myself and other adults. I reminded my oldest son that he was the first kid of a mom who grew up with girls. “You are going to be capable of different things than I was at your age. Tell me when you think you’re ready to try something new.” My youngest son heard the following: “You’ve seen the mistakes your brother made. You saw where your sister messed up. All I ask is that you make original mistakes.” And I meant it. Push, try, innovate.

5) Go first. We overthink so many things. Sometimes it’s an aversion to risk, other times we question our capability. The half-hearted attempt at a big goal or dream is basically an early concession. Although I’m pleasantly surprised at where my life has landed, I would have encouraged myself to push harder for what I wanted as a young woman. Someone will do the things we aspire to. Achievements are built around so many variables and factors we can’t see. If not you, then who?

Starting the Cabernet Coaches group in 2013 felt exceptionally bold. Deciding that simply reaching out to others was good, regardless of the results was freeing.

Going first applies to personal goals, but it’s also a personal responsibility: If you see something needs to be done, step forward or find the person who can.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Is it worth the wrinkle?” This makes me smile, and when I actually ask myself this question, I probably need one!

My grandmas outlived my parents by ten years, and their assisted living facilities were daily visits for me. You don’t just visit your “person” when you’re in a facility that frequently. Over the years, I got to know many of the residents and staff, and one day I was struck by conversations with two women in particular.

The basics of their lives were similar. Both were widows with adult children and grandchildren in the area, but they talked about them so differently. The first complained how her children didn’t visit enough and critiqued the time they did share. The second shared how proud she was of her kids’ and their families; she was grateful when they squeezed visits in between busy sports schedules. I knew before each woman opened her mouth what kind of conversation was ahead. It was already on their faces.

Wrinkles are where our inner thought lives and attitudes land for permanent display. The contrast between these two women’s enjoyment of life was clear as was the reason. I listened to the second woman, thinking, “I want smile lines!” Those don’t even seem like wrinkles; they’re more like joy that spilled out! So, whenever I feel the nudge of stress or resentment creeping in, that question is my perspective-finder. Is it worth the wrinkle? The answer, almost always is “No.”

Is there a person in the world, or in the US with whom you would like to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them.

I’m a huge fan of Vivek Murthy’s vision and work. His focus on healthy lifestyles and creating a culture of prevention as the United States surgeon general was forward-thinking and impactful. And he was the first American that I’m aware of to publicly address the loneliness epidemic and tie it to the larger social issues it feeds. I remember reading his words and thinking, “Yes!”

His empathy shines through, and I’d love a conversation with him. Although, if he prefers a long healthy walk over breakfast or lunch, I’m up for that, too!

How can our readers further follow your work online?

I’m easy to find! My main website, HeatherDuganAuthor.com, has links to books, videos, articles and information on how to book me for presentations and workshops. Look for me on Facebook, LinkedIn,YouTube, and Instagram too. I love connecting with readers and viewers.

This was very meaningful, thank you so much. We wish you only continued success on your great work!

Edward Sylvan, CEO and Founder of Sycamore Entertainment Group.

Interviewer: Edward Sylvan, CEO and Founder of Sycamore Entertainment Group

Testimonials & Reviews

She hit it out of the park! Heather was engaging, funny and shared many great stories from her life experience that resonated with our group. I highly recommend Heather for her speaking expertise, knowledge and ability to engage with the audience.

Theresa Byers IOM President & CEO Pickerington Area Chamber

As an Executive in Human Resources, I find most of my professional energy spent on educating others about the nuances of meaningful relationship building. Most often, the primary impediment is a lack of self-awareness, but Heather Dugan has boiled that conundrum down in a way that anyone can understand and immediately begin to act upon. Plain and simple, this is a good read on both a personal and professional level for men and women alike.

Jim McGannon Vice President, Human Resources & Organizational Development, Sarnova

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