Is It Lonely Being The Boss? We Asked 12 Leaders For Their Take

Is It Lonely Being The Boss? We Asked 12 Leaders For Their Take

Many of us strive to be the top managers or the boss. Rising through the ranks often means better pay, autonomy, and making powerful decisions that will help lead your business or company. But what few people talk about is how lonely and isolating it can be.

As a boss, you often have to make decisions solo. Or you have to balance boundaries between being a manager and a friend. While it never hurts to be approachable, you might have access to certain information you’re not yet allowed to share with employees, or you might have to let someone you truly value go because of budgetary or other issues. All these factors can make you feel like you’re on your own island.

To shine a light on the topic, we asked 12 bosses what loneliness at the top looks like for them and their tips on how to deal, and how to lead.

Is leadership lonely?

“Many people don’t view you as their friend but as their boss”

“Being a new attorney and self-employed was crazy, scary, and lonely to begin with. Then when I started adding more people to my team, it became even more stressful and surreal. Having people look to me as a leader (and not only a leader, but the freaking CEO) was intimidating.

“At times it is definitely lonely, especially since many people don’t view you as their friend but as their boss. And at times, it’s awkward critiquing employees that you do have that closer relationship with. It’s also frustrating when I want to hide myself from the team and just grind out research or documents in preparation for a case … But everyone is knocking on your door to help put out fires, asking for advice, or can’t figure out how to work the new coffee machine. Being in a managing/leading role has its fun days and it definitely makes me feel like a badass. But it comes with equally stressful and challenging days.”

—Melissa McKinney Breyer, founder of The Hive Law

“It’s not my job to provide emotional support”

“I learned early on that I’m not my employee’s therapist and that it’s not my job to provide emotional support. To address the majority of concerns my employees have about juggling motherhood and their career working for me, I built a housing, meal, and childcare facility adjacent to my garment factory in Savannah, Georgia. I don’t like listening to problems, but I’m good at solving them.”

—Misha Kaura, CEO, Darlinghurst Enterprises, New York

“I have to be very stern and authoritative”

“As the owner of a wellness center and massage school, I have staff and independent contractors who work for me. My unique challenge is that most of my employees/contractors are older than me and feel superior to me in some way. I feel I am not taken seriously most times and I have to be very stern and authoritative to get people to do things.

“As successful as I am, it is interesting to note that my staff question, doubt or sometimes even deny my vision! I had to let a lot of people go but now have a team who believe in my vision and work hard alongside me. It took a while but I finally got it right!”

—Uma Alexandra Beepat, owner of Lotus Wellness Center in Manassas, VA.

“My biggest challenge … is bordering the friend/boss line”

“I own a small publishing company so I am the brains behind our project but also the supervisor of our team. I can say without a doubt my biggest challenge being in a supervisory role is bordering the friend/boss line and knowing where that line is. My company is pretty small. We’ve always hovered between four and eight employees in our 10 years of business, so a small team often feels like a second family.

“As an entrepreneur I often feel like I am living on a deserted island within my own company”

As an entrepreneur I often feel like I am living on a deserted island within my own company, because I have to internalize so many of my thoughts, fears, and dreams instead of sharing them with the team. It’s certainly not their job to be my counselor or coach and I don’t want to distract them from their work priorities I need them to focus on.”

—Heather Vreeland, publisher and editorial director at Occasions Media Group

“It’s very helpful to have outside advisors to give perspective”

“As the Glosslab CEO, it feels lonely a lot of the time because I’m alone in my day-to-day issues and questions. It’s very helpful to have outside advisors to give perspective, however I’m the only one truly in my shoes. Ultimately, I’m responsible for everything in our company from customer experience to employee management—so at times it can feel overwhelming!

“[And] it can be a difficult balance of being boss and being friend. It’s natural to want to be liked. I think everyone feels that! But, you also want to maintain authority, so there’s a lot of navigating interpersonal relationships involved as a female boss.”

—Rachel Glass, founder & CEO of Glosslab, New York

“Loneliness … can be a great teacher”

“Oh my goodness, yes, it gets very lonely. In prior years I mitigated that loneliness by taking a more active role in the campaigns and by allowing more time for socializing but as the company and I have matured, I’ve had to make some changes that are isolating.

“What I’ve learned is that the loneliness, while it’s certainly a bummer, can also be a great teacher. I’ve learned not only to trust my gut but to effectively question myself in a way that doesn’t undermine my confidence but rather ensures I make better choices. That ying yang dynamic is essential.”

—Andrea Samacicia Mullan, owner, Victory Public Relations, New York

“It’s important to hire people that can manage your manager”

“As a one-woman-show there are so many days where I no longer want to make decisions but rather be told what to do. I think when hiring, it’s important to hire people that can manage your manager. They make decision-making easy since they come to you with multiple solutions and reasons why the decision should be one way or another … [Establishing boundaries is] a slippery slope for sure, but I try to adhere to the work/boss mode in office hours and friendship can happen after these hours.”

—Emily Merrell, founder and CEO of Six Degrees Society, San Francisco

“I have to take responsibility…and that means sometimes being the bad guy”

“We’re a small team of just about 20, and that means everyone wears a lot of hats. Part of the fun of working—for me at least—is being friendly with the people that I see every day. As we have grown over the last few years, I’ve been fortunate to build a team. Part of that has been forcing myself to be the adult in the room. That means something as simple as leaving the company party early, to something as complex as quarterly performance reviews.

“It can be lonely, because leading by example means you are, truly, a leader out ahead of everyone else. For someone that is naturally extroverted and social, it has been incredibly difficult to find the right ways to show that I genuinely care about my team, but without sending the wrong message. At the end of the day, I have to take responsibility for their actions, and that means sometimes being the bad guy.”

—Emily Espinosa, co-founder, head of community, PodSquad, New York

“You feel like you are on an island”

“I have surrounded myself with people who are better and smarter than me. I have a CFO who I spend a great deal of time with making financial decisions. I have an HR consultant who, because of her background and expertise, confirms or negates and generally advises me on all employee-related matters. Even the significant investment of an executive coach has saved me on so many levels. She’s my counselor, my challenger, my cheerleader, my voice of reason.

While all of these are not full-time employees for Choice, they are people with whom I have surrounded myself because I value their expertise and opinions. I consult with them often so that it doesn’t feel like I’m operating all alone.”

—Heather Dixon Adams, founder/CEO, Choice Media & Communications, Franklin

“No one is checking in to manage your workload”

“One of the trickiest parts of being a CEO of a small company is realizing that while your team cares and supports you, no one is checking in to manage your workload. So, I’m just at this stage where I work constantly. Work-life balance doesn’t yet exist. I try to create it for my team but I feel like I can’t create it for myself just yet.

Building a young entrepreneurial team is my favorite part of my job but it doesn’t mean that it isn’t lonely. I fail and make mistakes so they don’t have to.”

—Amy Shackelford, founder/CEO of Modern Rebel & Co., Brooklyn

“It’s not work-life separation; it’s work-life integration”

“I’ve found—no matter what the size of the company—you really have to focus on your mindset and understand that maintaining both your home and work life is not work-life separation; it’s work-life integration.

“I focus on making sure to prioritize correctly so that my energy and quality time always goes in the right direction in work and life … Focus on the quality of your personal and professional relationships, get a mentor, reach out to someone in a similar position you admire for coffee, or join a boss meet-up or executive forum. Many of the challenges you have as a boss at a small company, others have too–continue to learn and get inspired and learn new skills to bring to your job and your team.”

—Kim Perell, entrepreneur, angel investor and CEO of Amobee

“I’m the same person but show different sides”

“Being close friends with an employee is fun … until it isn’t. I joined [Entrepreneur’s Organization]to be able to talk to other people that are bosses/entrepreneurs because I can’t share certain information with my employees. It’s challenging to be a hard-hitting CEO then put on my mother/daughter/sister hat. I’m the same person but show different sides  to each element of my life. Hiring employees is the single most difficult element of being a CEO. It’s an art and a science, and I’d love to master it sooner rather than later!”

—Natasha Miller, CEO/founder of Entire Productions

Whether you’ve made it to the C-suite or are about to step into your fist management role, leadership skills are something we can always brush up on and improve upon. Join us in Leadership Hall at the Girlboss Rally for actionable workshops and IRL advice that will help you step into your next leadership role. Register now at