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Jessica Dennehy of Pivot & Slay: “Leave Your Comfort Zone in the Rearview Mirror”

Leave Your Comfort Zone in the Rearview Mirror. Don’t be shy to breach the boundaries you’ve become comfortable with. Extending outside of your sweet spot will propel you forward and let you inch past others in your lane. Staying where your comfortable will only ensure mediocrity and being average doesn’t help you ride out the […]

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Leave Your Comfort Zone in the Rearview Mirror. Don’t be shy to breach the boundaries you’ve become comfortable with. Extending outside of your sweet spot will propel you forward and let you inch past others in your lane. Staying where your comfortable will only ensure mediocrity and being average doesn’t help you ride out the highs and lows of business.


Being a founder, entrepreneur, or 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 Jessica Dennehy, a business coach and legal strategist on a mission to help other entrepreneurs fulfill their dreams. Through her company Pivot & Slay, she coaches entrepreneurs to be adaptive and evolve their mindsets so their companies can withstand the test of time. She helps structure companies, create more efficient business processes and helps protect brands using Trademarks and other legal strategies that most small business owners overlook.


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?

As a little girl, I dreamed of becoming a lawyer. For almost a decade, I worked as a regulatory attorney on Wall Street and I loved every second of it. In 2012, a need in the marketplace sparked an idea for a business in a totally unrelated field — luxury barbershops. I started my entrepreneurial journey by opening a brick and mortar side-business near my home in Long Island. Within three years, that business took off and I left corporate life behind to pivot into entrepreneurship full time. So far we’ve opened three locations and we are still continuing to grow, but my journey did not end there. During the pandemic, I started helping local small business owners navigate the shutdown and found that my true passion was helping other entrepreneurs emerge and succeed. I opened a consulting company where I can cultivate that passion and help other entrepreneurs emerge and succeed.

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

During the global Covid pandemic, my barbershops were shuttered. As I tried to navigate the shutdown for my own businesses, I realized how difficult it was to understand the landscape, especially under the stress of unemployment. I decided to offer free coaching advice to other small business owners through my social media accounts so that they can have a source of support through these trying times, apply for government loans and then eventually be able to reopen and thrive.

By providing these services, I realized that I had cultivated years of knowledge that could be helpful to other business owners and the idea for Pivot & Slay was born. Now I have several coaching clients, I am writing a book about how to continuously pivot in business and in life, and I am creating course content to help new entrepreneurs get started. I am also co-authoring a book about what to expect in the first 12 months of business.

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

Ambition and leadership skills come very naturally to me. However, being a successful entrepreneur takes a level of self-awareness that you have to constantly nurture in order to keep evolving. In order to be successful in business, you have to take risks. And you cannot do that unless you know yourself well enough to trust your instincts. This is something I had to work to develop within myself. I became more aware of my instinct-driven decisions and began to track when my gut was right and when it led me astray.

People who are not confident are not going to trust the feeling that they get in their gut when they’re presented with a problem. Instead, they will question themselves. For a long time, I was that under-confident person constantly ignoring my instincts and overthinking every single decision. What a waste of time!!!! The gut instinct is the first, initial feeling you get before your fear kicks in. Take note of it and then promptly tell that fear factor to go away!

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?

My dad was definitely my first inspiration to become an independent thinker and one day work for myself. He always seemed happiest when he was opening and running his own businesses. But because he had me so young (21), he felt the pressures of financially support our family and wasn’t able to take the risks he needed to get to the next level. Justifiably so, he couldn’t let go of the safety net that was his corporate job. Years later, I would understand that exact feeling as I supported my own family. I took a big risk in opening my first business, but by then I had trusted my gut enough to take the leap. And when it paid off, I never looked back.

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

The brand I built reflects my genuine values and that authenticity shines through in all of my content and coaching. My consulting style intermingles life coaching with business strategies, which is a unique approach. I strongly believe that awareness and mindset are cornerstones for success. You cannot improve your mindset if you aren’t willing to confront the things that drag you down. To get rid of this dead weight, we have to become aware of what our hurdles are so that we move past them and become a stronger version of ourselves. By implementing these techniques myself, I was able to transform my own life at a time when I could have crumbled. I didn’t just survive, I thrived. And I wanted to help other people do the same.

Most of us do not realize that tapping into our physical selves can allow us to achieve a more potent connection with our emotionally intellectual selves. This is a lesson I learned through the practice of yoga in 2016 during the breakup of my marriage. Through fitness, I become more comfortable with taking risks and confronting the mind chatter that held me back from focusing. This directly translated into a strength in business. As I became more comfortable with who I was and more confident in what I could achieve on the mat, I began to take risks in my business life that forever changed the course of my career.

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?

  1. Grit. Do the work. In business, you must be able to put the work in to see the results. At first, that means late nights doing the things you aren’t good at, don’t enjoy and aren’t passionate about. But that’s what it takes to push forward. You cannot afford to immediately delegate something just because it isn’t your strong suit. You have to learn to grow in each aspect of the business before you can effectively entrust it to the right person. This takes humility that many people do not have. But remember, humble beginnings lead to successful endings. When my barbershops opened, you bet we were there sweeping the floors, cleaning the toilets and running the register.
  2. Take Decisive Action. Trust your Gut and always choose bad decisions over indecision. As a business owner, you’ll make a ton of decisions each day and to stay efficient, you have to be decisive. Stop overthinking each choice you make. Failure to act is a by-product of fear. We are scared to make the wrong choice and fail. But failures are a necessary evil and give us an opportunity to evolve. Otherwise, we will play it safe and not take the risks necessary to achieve true success. The outcome is not guaranteed. You may stumble a few times before you find the right path for your company or brand. Don’t let that deter you from pushing forward. Learn the lesson, pivot and slay. In 2020, while the barbershops were shut down and I was unemployed, I used my savings to kick start my coaching company. This could have gone horribly wrong, but I took a risk and went all in.
  3. Get organized. As an entrepreneur, you’ll have a lot on your plate and the only way to stay productive and efficient is to get organized. Get a calendar, make a schedule and stick to it. The more you respect your own time, the more others will do the same.

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?

I was taught to be risk adverse and think of every possible outcome before I made a decision. I spent most of my life living cautiously, rather than taking chances that could have catapulted me forward faster. The first time I threw caution to the wind was when I got into my dream law school the night before classes began. I was surrounded by boxes, ready to move with my family to Florida when I got the call from a school where I was waitlisted. I had no financial aid, no books, and was 200 miles away. I had to make a live-altering decision on the fly and I went with my gut. Everyone thought I was crazy, and maybe I was. But that decision positively impacted the rest of my life and since then I’ve been choosing imperfect action over inaction. It’s a win-win because even if I fail, I learn a lesson that makes me into a stronger person.

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?

Appreciate your staff. When you’ve finally achieved the status of CEO, this means you are working on your business rather than inside your business. Having the right staff in place gives you the luxury of monitoring the vision of the company, rather than the daily operations. Appreciation comes in many forms and different staff will value different opportunities. It is your job as CEO to determine what is valuable to whom and use it to show your gratitude. For some staff, extra time off or different days off each week will make a significant impact in their life. Other staff may want more responsibility so that they can generate more income. Some staff simply want you to take the time to ask about their family and personal life. These small changes will impact the company culture and maintain a positive working environment for everyone.

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

Be Generous with the Knowledge. Use your social media pages to give away small pieces of information that are helpful and add value to other people. Be generous with it. Often times we are timid in sharing our knowledge because we think competitors will be able to replicate our brand. What we don’t realize is that people mostly consume information without being able to implement any of it. And, although someone can try to copy your idea, it’s your vision and leadership that will make or break a company and THAT cannot be replicated.

So share your knowledge and dare other people to level up. You’ll establish yourself as a force in the industry and gain credibility in the marketplace, which will only drive you to keep doing amazing things!

Can you help articulate why doing that is essential today?

With virtual life on the rise, the markets are saturated now more than ever. Consumers have access to a ton of people who do what you do. The only way to set yourself apart is to establish yourself as the premier expert in your field. Be unique in the way you present your information and be generous with the knowledge. Let consumers hear your message so frequently that your brand is the first connection they have when they think about your industry.

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?

They come up with a million great ideas and never follow through with any of them. They are so busy visualizing and perfecting, that they miss an opportunity to get into the marketplace and sell. Do not spend hours on the perfect sales pitch or perfect website. Throw something up that is good enough and get moving. As your business develops, you’ll be able to fine-tune all of those little things, but for now, start starting!

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”?

Entrepreneurship is a constant evolution and that is why things will never be completely leveled out, like in a “regular job.” If you have a standard career, someone else is worrying about the ups and downs of business while you plug away at your small role in the overall company structure. As the leader of the company, it is your job to balance the delicate ecosystem of the company. You act as a visionary, taking decisive action to keep the brand fresh and uniquely positioned against your competitors. But you also are the integrator that must understand how these decisions will shape and affect each smaller facet of the company.

You cannot take your foot off the gas because there is always a hurdle ahead. That can be something simple such as a competitive business opening close by or a more complicated hurdle such as an economic crisis. As an owner, you are always in the driver’s seat looking ahead so you can swerve and pivot without crashing the car.

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.

One of my highest highs came recently when I was interviewed about my upcoming book launch. For the past several months I have been journeying through the writing process, which is lengthy and emotional. You are in the trenches so-to-speak digging up anecdotes and stories from your life that can help inspire other people. This was the first time I would be speaking about the book to someone other than my editor and I was elated. As a little girl, I dreamed about being a published author one day and this dream was about to come true. The interview went well, and I was excited to showcase something that made me so proud. Surprisingly, that was not the highlight of the moment. My 8-year old daughter overheard the interview and when I walked away from the computer she looked up at me and said — “Mommy, I know I can do anything I dream about because I see you doing everything you dreamed about.” That moment was priceless.

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.

I had a low at the end of 2020 when we had to downsize one of my barbershops due to the pandemic. I had an emotional attachment to this particular shop because it was the one we opened right after I left my career on Wall Street. I spent countless hours putting my heart and soul into the buildout of that shop and around that time, my marriage started to crumble as well. Building that shop made me feel like a phoenix rising from the ashes and contributed greatly to the growth and evolution of my positive mindset.

As second locations often are, that shop was double the square footage of our first shop and that was probably our first expansion misstep. Although that shop performed well, it had never quite scaled the way we hoped. During the pandemic, it took a big hit and by the end of 2020, downsizing quickly became our only viable option. From a business standpoint, I knew this was the right decision. It would help us pivot the business so it could shine. But on a personal level, this decision was emotional. As we tore down the décor and removed the furniture, space slowly became an empty box and my heart hurt.

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

To bounce back from any troubling situation, I always focus on changing my mindset. The way we frame things can either be a tremendous asset or hinderance. Downsizing the shop was no different. I had to detach my emotions from this business decision and push ahead with the choice we knew was right. When I felt myself getting emotional about it, I would talk myself through the fallout. If we plugged away and kept it business as usual, the shop would eventually have to shut down entirely, which would be a far greater loss. Once I flipped the script on myself and changed my perspective, I was able to come to terms with the decision and push forward.

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.

Maintain your Mindset — this will be key in all you do. If you can stay positive during the lows and stay grounded during the highs, you’ll be able to ride out any rollercoaster.

Don’t Take Your Foot Off the Gas. Keep going. Even when things are going really well keep pushing forward with the same hunger. If you let up on the gas, you won’t have the momentum you need to ride out the lows.

Be Innovated. The businesses that survive are the ones that evolve. Stay fresh in the mind of the consumer and keep making tweaks that improve your business mode, company values, and branding.

Leave Your Comfort Zone in the Rearview Mirror. Don’t be shy to breach the boundaries you’ve become comfortable with. Extending outside of your sweet spot will propel you forward and let you inch past others in your lane. Staying where your comfortable will only ensure mediocrity and being average doesn’t help you ride out the highs and lows of business.

When business is low, spend money. You heard me right. My business partner in MadMen taught me this one. At first, I was skeptical too, but I trusted him and he was right on this every time. Each time we had a low, we spent money on advertising, on updating, on renovations, on tweaking. And guess what? Each time, it worked.

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?

Resilience is not allowing our worst moments to define us, but instead, sculpt us a more indestructible version of ourselves. You must be ready to bounce back, pivot, and slay the day. Resilience is critical at all times, not just in a post-pandemic world. Each year will bring unique hardships in life and in business that you must be prepared to overcome. Resilient people are those that are emotionally aware, consistently work on controlling and improving their mindset, and are dedicated to becoming a better version of themselves one step at a time.

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

I was a straight-A student my whole life, working hard towards my goal of going to law school. Unfortunately, standardized tests were not my strong suit and so my LSAT scores were not as high as I had hoped. For that reason, I was rejected from all but one of my dream law schools and waitlisted by the one that didn’t reject me. I was completely devastated but eventually gathered my mental strength to make a plan. Instead of feeling settling for a safe school, I focused my mindset on taking the year off, getting a job as a paralegal in a corporate law firm and learning as much as I could while I waited to reapply to my dream schools.

Two weeks before my job began, I received a call saying I’d been removed from the waitlist. My dream school offered me a slot, but the catch was that I had to start the following morning at 9 am. I was 200 miles away and didn’t have any financial aid or books, but I said yes. I had proven to myself that I was resilient and could make any scenario work in my favor. This determination landed me a spot at one of my dream schools from which I eventually graduated and launched a prestigious legal career.

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

Now I can, yes. This took a year of self-development through fitness and meditation. In trying times, nothing good can come from panic. A racing mind is chaotic and creates anxiety. Wrangling your racing thoughts gives you clarity. A great way to keep your mind focused is to try something that is physically challenging. While your body is concentrating on this physical task, it has one focal point. The mind chatter cannot exist when the mind is so intently focused. This creates a type of moving meditation. When a random thought floats into your mind, you’ll be able to consciously register it and deal with the anxiety it causes, rather than being dragged into an auto-pilot frenzy of random thoughts. My outlet is yoga. I practice daily postures and flows that challenge my mind to stay focused so it cannot multi-task. This has been a pivotal part of my health mindset and is a staple in my daily routine.

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.

Your attitude is your energy. As a leader, you will set the tone of the company and the company culture. Whatever energy you bring to the room will be emulated by your staff and be woven into your brand. That’s the impact you have as a visionary entrepreneur. Your behavior is setting the standard for the rest of the company to follow.

Similarly, your clients will be feeding off your energy and want to see that you are a good collaborator. In order to maintain a positive connection with your customers, you will need an open mind and a positive outlook. This will get your clients the best results, no matter what industry you’re in.

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?

Wrong Decision > Indecision. Taking imperfect action still gets you further than waiting around for the perfect time, perfect moment, perfect website, etc. Push forward with your ideas and perfect them along the way.

How can our readers further follow you online?

PivotandSlay.com

JessicaDennehy.com

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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