Trisha Pérez Kennealy of Inn at Hastings Park: “Family first”

Family first: When the kids call, they always get put through. When I was little, I loved calling my dad at work. Whenever I called, I was put through. He worked all the time when we were little, but being able to speak with him whenever I wanted mitigated the fact that he often came […]

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Family first: When the kids call, they always get put through. When I was little, I loved calling my dad at work. Whenever I called, I was put through. He worked all the time when we were little, but being able to speak with him whenever I wanted mitigated the fact that he often came home after I was asleep.

Many successful people reinvented themselves in a later period in their life. Jeff Bezos worked in Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Croc was a milkshake-device salesman before starting the McDonalds franchise in his 50’s.

How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?

In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.

As a part of this interview series, I had the pleasure of interviewing Trisha Pérez Kennealy.

Trisha Pérez Kennealy is a mom, chef and owner of Inn at Hastings Park, the only Relais & Châteaux hotel in Boston. Her life has always been centered around food, cooking and entertaining. She is passionate about bringing friends, family and colleagues together over a great meal.

Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

Born in New Jersey, I grew up in Puerto Rico and spent my childhood surrounded by friends and family sitting around the table sharing food and stories. When I was in middle school, my family moved back to the United States, to Massachusetts; my parents picked Lexington — the birthplace of American liberty and where the Revolutionary War started. Cooking and eating with my family were an incredible source of comfort to me while I got used to living in a new place.

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

I love the saying “Friends are the family we choose for ourselves.” When I was a child, my family lived in Puerto Rico where my father is from. We lived in the metropolitan area outside of San Juan and most of our relatives were on the southern side of the island. As a result, we became very close with our neighbors as well as some of the families we attended school with. That was in the 70s and we are still friends with many of those families.

I have always treasured my friendships and love spending time entertaining our friends at our home in Lexington or our home in Maine. I love having big groups of people for dinner and introducing people from different facets of my life to one another. This mantra has also carried into my professional life as I encourage the staff at the Inn at Hastings Park to treat our guests as if they were guests in our home.

You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much? If you can, please share a story or example for each.

Compassion: At the core, I am a people person who thrives on human interaction — important attributes for a hotel and restaurant owner. I love meeting people and getting to know their stories. People often come to me when they have a challenge or a problem they are addressing, and I pride myself in being able to help them find sustainable solutions. A dear friend from college, who was a few years ahead of me, taught me to always make time for the people in your life as the work will always be there. That sage advice has proven to be true time and time again.

Perseverance: Opening a 22-room hotel and restaurant in the historic district of a small New England town is not a task for the faint of heart. The process from seeing the property the first time to opening the doors to welcoming guests took three years! Large multinational corporations with offices in our town signed leases, renovated and moved into their new locations quicker than that! When I want to get something done, I will keep at it, changing tactics and trying different things until I make my goal a reality. We lifted two buildings off of their foundations and moved one 18 feet to satisfy requirements needed to build the Inn. Move a building — check — no problem!

Humor: Laughter is the best medicine and stress reliever on the market. I am a glass half-full type of person, so I tend to look for the positive sides of situations even in the darkest moments. That does not mean that my life is always joyful and happy — it just means I try to keep it all in perspective and recognize that life is full of sad and challenging moments, but where we find our strength is in how we deal with and overcome those challenges.

Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?

The summer before I graduated from college I worked as an intern at Citibank and returned for my senior year with a job offer in hand. In one of life’s funnier moments, my management training job was eliminated during the second semester of my senior year — I was fired before I even started my job. Then I was lucky enough to land a job at Liz Claiborne, the woman’s apparel company, which became the first company founded by a woman to make the Fortune 500 list. At the time, the company was a shining star known for its dynamic founder. I was hired by one of the senior executives who recruited students out of top colleges and exposed them to different aspects of operations. I learned a lot about customer service and logistics, but ultimately left to join another commercial banking management training program.

After business school, I made the switch to investment banking, working first for Bear Stearns and then for Robertson Stephens. My husband and I were both transferred to London with our respective companies during the summer of 2000. I continued to work at Robertson Stephens through 2001.

And how did you “reinvent yourself” in your Second Chapter?

I followed my heart and decided to pursue my love for food and hospitality. I attended Le Cordon Bleu in London and earned both my Diplôme de Cuisine and Diplôme de Pâtisserie in August of 2003. Then I opened a 22-room hotel with a restaurant in Lexington, MA. I first saw the property that became the Inn in December of 2010 and opened the doors in January 2014.

Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?

My oldest child, my daughter Gabriella, was born a few weeks before 9/11. In the aftermath of that tragedy, there was a huge impact on the finance sector. The job that I was slated to return to after maternity leave was no longer viable. I accepted an offer to leave and used my severance to pay for my culinary degree at Le Cordon Bleu London.

Many people, including myself, realigned their priorities after 9/11. I had long dreamed of having my own business and had an instinct that I wanted the business to be food related. The initial idea was to have cooking schools that were focused on children. I realized in the fall of 2001 that there was no need to wait any longer to begin my next chapter. If I was going to take the plunge, it was as good a time as ever.

When done full time, the Grande Diplôme program lasts 9 months; I took 18 months to complete my pastry and cuisine degrees as I was also busy with my daughter. When I returned to the United States in September 2003, I jumped into full-time motherhood and professional volunteerism. I ran for Town Meeting — which is the equivalent of the town’s legislature — when my second child, my son Conor, was only two weeks old, and became very involved in the children’s schools and advocating for public education over the course of the next seven years. At the same time, I was cooking all the time and donating my services to charity auctions — gourmet dinners for groups of people but always looking for the right location to offer cooking lessons and promote my very personalized style of hospitality.

What did you do to discover that you had a new skillset inside of you that you haven’t been maximizing? How did you find that and how did you ultimately overcome the barriers to help manifest those powers?

Earning Le Grand Diplôme was an affirmation that I could cook well and that I also felt very comfortable teaching others to cook. It also affirmed my capacity to multitask, as I had a baby, was going to school and, by the time I was nearing the completion of this degree, I was pregnant with my second child. The harder part after earning the degree was figuring out the best way to put it to good use. I graduated from Le Cordon Bleu in August of 2003 and did not find the property that would become The Inn at Hastings Park until 2010.

The irony is that you start a business to focus on particular skills and do not always get to use those skills as often as you might like. Between 2010 and 2011 all of my energy was devoted to the rezoning of the property. There was a small but vocal group of neighbors that were opposed to the project. It was a full-time job in itself preparing and presenting at all of the different meetings and garnering the requisite support from the community for the rezoning to pass through Town Meeting with the required 2/3 votes. Once that process was completed it took an additional 18 months to renovate the three buildings that comprise the property. They were built in the late 1800s and needed significant upgrades to make them suitable for operating a luxury hotel.

How are things going with this new initiative? We would love to hear some specific examples or stories.

I love my job, but it is hard work. I had never worked in the hotel industry so I have had to learn as I go. I have been very lucky to have extremely capable managers and employees who are as passionate about hospitality as I am. I love the days when I get to work in all of the departments at the hotel: front desk, housekeeping, culinary — that is a great day!

Getting through the pandemic has tested all of my skills. The silver lining is that I am focusing on my true love — teaching people to cook together. I have recommitted to teaching and have been teaching amazing classes at the Inn, including immersive culinary weekends that have been a big hit. I spend over 20 hours with our guests during these weekends teaching, cooking and eating a lot together.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I am incredibly grateful to my parents, husband and children for being so supportive on this journey.

My father and mother taught me how to blend being an entrepreneur while still being dedicated to your family. My dad also dedicated three years of his life to making my dream of opening an Inn a reality as he was the project manager for the renovation.

My husband, who was my classmate at Harvard Business School, is my financial partner. He is supportive but also holds me to the highest standards in terms of pushing me to always be thinking of how to make the business better and stronger. It has been a significant financial and emotional investment for both of us.

My children have always been kind and understanding when the Inn has taken time and attention away from them. They were also my inspiration for not giving up on my dream when those opposed to the project were trying to stop the project with unreasonable demands. My son Conor, who was only seven at the time, reminded me of the importance of having fun with the process; I needed to recommit to my passion for the project to get us through the rezoning and the renovation.

Can you share the most interesting story that happened to you since you started in this new direction?

My favorite stories involve guests who have become like family.

I had one guest who started visiting when her daughter and son-in-law moved to town. She would come more frequently once her first grandchild was born. She had a recurrence of breast cancer when her grandson was young and stayed with us while undergoing treatment. Sadly, she did not survive but her family still comes often and it has been a gift to watch that grandson get older.

Another favorite story involves a family I encountered one afternoon in the Living Room. I love talking to our guests and kept saying hello as I was walking through the Living Room. When I finally had a chance to spend more time with them, I was teasing about why they had come to visit. They all laughed nervously. I asked “do we need a bottle of wine?” — to which they all wholeheartedly agreed. It turns out that this was a very special reunion. The oldest daughter had been put up for adoption because her parents were not married at the time of her birth. The couple did end up getting married afterwards, and had two more daughters. The mother sadly had passed years before, but the older daughter found the father. This meeting marked the family’s reunion. The youngest of the sisters had chosen the Inn because it reminded her of her mother. I ended up sitting with them for over two hours and am so touched that they trusted me to be the first person with whom they shared this moving story. I sat with them again the next day when they invited a photojournalist to sit with them and document the story for their family.

I am honored when the Inn provides a special place or sanctuary for people to share life’s important moments.

Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?

There is some point in every day that I question myself. If you never struggle with believing in yourself, you are being risk averse. You have to take risks to make progress in your life.

When I am struggling, I try to visualize myself where I want to be. At times the rezoning seemed insurmountable, but I used to stand in the hallway that would become the entrance of the Inn and imagine standing there with guests. You cannot be afraid to fall but you have to get back up as quickly as you can. Learn from your mistakes and forge ahead forcefully.

In my own work I usually encourage my clients to ask for support before they embark on something new. How did you create your support system before you moved to your new chapter?

I created a support system by asking questions of anyone I thought I could learn from: servers, housekeepers, cooks, chefs, general managers, even the president of one of Boston’s leading hotel companies. I am still creating that support system as being an entrepreneur can be a lonely existence. You have to be overly optimistic by nature but also have to be able to accept honest and sometimes harsh criticism.

I am grateful to fellow entrepreneurs who are willing to share their experiences and offer insight. I value their candor and appreciate them holding me accountable.

Starting a new chapter usually means getting out of your comfort zone, how did you do that? Can you share a story or example of that?

I get out of my comfort zone on a daily basis depending on which department I am working in. I think this has been an invaluable lesson for my team to see me push myself to learn as much as I can about what they do. When I am challenging them to try new things they respond as I try to do the same thing on a daily basis.

Fantastic. Here is the main question of our interview. What are your “5 things I wish someone told me before I started leading my organization” and why? Please share a story or example for each.

I learned a lot from watching my father run his own businesses.

1. Family first: When the kids call, they always get put through. When I was little, I loved calling my dad at work. Whenever I called, I was put through. He worked all the time when we were little, but being able to speak with him whenever I wanted mitigated the fact that he often came home after I was asleep.

2. Work is a marathon not a sprint. The to-do list will never be done so you have to set parameters. When my children were younger, I would try to cram a whole day’s worth of work into the hours when they were asleep. All it meant was that I was sleep deprived. Pick a pace and schedule and try to stick to it. This is a skill I work on daily.

3. Always have something in your schedule that is fun and that you do just for you. I started ballroom dancing over five years ago. It has really helped me be happy and focused in all aspects of my life. It is a gift to be able to have something fun that challenges me both physically and mentally.

4. Don’t be afraid to ask for help or coaching. I started working with an executive function coach last summer. There are always too many things going on in my life and I was not feeling satisfied with how I was managing. I have learned that my expectations of myself are sometimes unreasonable, so having someone to strategize with about how I am approaching things has helped me refocus and become more productive. I think coaching is an invaluable tool for people in leadership positions.

5. Have fun! If this year has taught us anything it is that life is precious; it is meant to be enjoyed. I am so lucky to have a job that I love and I want to create an environment that enables my team to enjoy themselves while they grow professionally and personally. As a business leader, it is important for me to model behavior for my employees. If I want my employees to practice work life balance, I need to model that behavior.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

I am starting a movement to encourage people to cook and together with family, friends and colleagues! During the pandemic, I have been hosting virtual cooking classes for my employees, patrons of our local library, as well as Inn guests.

Food is meant to bring people together. It is also the best form of medicine we have available. As a society, we have an obligation to make healthy food readily available for all. Dean Dary Mozzafarian of the Friedman School of Nutrition (full disclosure: I am the Chair of the Board of Advisors) believes that many of the COVID deaths could have been prevented if patients had better metabolic health. The United States has the resources to make healthy food accessible to all. The investment we need to make this happen would have incredible returns. So let’s cook together!

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them. 🙂

This is one of my favorite questions. Given my ambition to encourage people to cook and eat together, I would love to spend an afternoon walking around Paris, visiting multiple markets to buy the ingredients to make a spectacular meal with Julia Child. I would love to hear about her job as the predecessor to the CIA, her experiences at Le Cordon Bleu in Paris, the challenges of writing her incredible cookbook and what she liked most about hosting her TV show.

How can our readers further follow your work online?

Follow me on Instagram at @trishaperezkennealy to see what’s going on at the Inn! To book a stay at the Inn, please visit

Thank you so much for sharing these important insights. We wish you continued success and good health!

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