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Esther Dormer: “You will fail, and it will help you reach for success”

You will fail, and it will help you reach for success. You need to know what does not work for you, and then you can find what does work. 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 […]

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You will fail, and it will help you reach for success. You need to know what does not work for you, and then you can find what does work.


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 Esther Dormer.

Esther Dormer has designed and built diverse projects, from huge country compounds to apartments and houses in the city to vacation homes. She has worked on both interiors and exteriors, including landscaping and outdoor entertainment spaces. She is known for her romantic yet modern take on style, and has created luxe living in small spaces as well.

Pittsburgh is Esther Dormer’s base, but she sources design elements from around the globe. You can follow her on Instagram @dormerdedign.


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?

I was born and grew up in the thriving city of Pittsburgh. I still live there now. I have four sisters, a mother who taught piano and a father who had a computer business. It was a very happy and idyllic childhood, but even as a young girl, I wanted to accomplish things. My sisters and I started babysitting at the age of 12, so we could earn money for clothes! We rode bikes, went to the mall, talked on the telephone! My childhood was very much the middle class, suburban lifestyle.

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

Whenever you push the envelope in anything, you will sometimes fail. Failure and success are good friends and travel together”. You need to fail in order to see how to succeed. It is a difficult process, and sometimes discouraging, but I look for inspiration in failure.”

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.

I have a strong work ethic. My very first real job was working at the local TGI Fridays. Because I was such a hard worker and was constantly finding ways to improve how the restaurant functioned, I was the youngest manager there at 26 months.

I love to learn new things. When I purchased a farm to grow food for the local food bank, I couldn’t keep a house plant alive. I learned about soil, permaculture, nature, plant health, farming equipment, etc. Through books, conferences, networks, etc. you can learn a lot about anything. Mastery comes from doing it.

I am not afraid of doing whatever it takes. One summer when I wanted to work at a very hip bar, they told me that they already had enough bartenders. I went in every day for two weeks and they kept telling me the same story. One day I went in again and said not only would I be their best employee, but I would clean anything, including bathrooms. They hired me on the spot. Learning to offer added value was a very strong lesson for me to learn.

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?

I graduated with a marketing degree from Penn State University and started my career selling ads for a real estate publication. It was a small operation, and I did every task from getting the ads, taking the photos, arranging for copy and assisting the production and distribution of the magazine. I moved back to my hometown after a few years and opened a boutique selling high-end costume jewelry including art to wear by Robert Lee Morris, Erickson Beamon and other prominent jewelry artists.

When my father passed away suddenly, I worked with his associates in their computer business. I was involved in every aspect of the business and learned an entirely new field.

Over time, that business was sold and I purchased a farm outside of the city and started growing fresh, organic produce for the local food bank.

The farm is probably where I learned the most life lessons. Since we were organic, we had to battle the elements using permaculture techniques and ingenuity. We built beautiful ponds to hold water for when we needed it and created hillsides with terraces to trap water. We used biodiversity and allowed nature to take care of the rest. I learned about the plant growing process, how you cannot rush plants, that they operate on their own timetable, and if the soil is not healthy the plant will not be healthy.

It struck me how that reflects our own lives. If you are not healthy mentally and physically, it is hard for anything to go your way over time. I learned about how trees spread their roots deep and wide, similar to friendships and support. You also realize, that sometimes, no matter what you do, there are certain spots for unknown reasons, where a plant won’t thrive. That’s when you know you have to move on and set your sights on another place.

After donating over 100,000 pounds of food grown on this 150-acre piece of land, I had the plan to create a neighborhood based on the concepts of healthy food, healthy homes and a very connected community with beautiful houses. Instead of a cooperative or commune, it was a high-end neighborhood offering the best in natural living.

But then, the housing crisis struck and the interest I had in these projects completely dried up. I had to switch gears and turn the place into a retreat that someone might purchase. And that would be the beginning of my second chapter.

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

I assembled a wonderful, skilled and knowledgeable team. The people that I worked with helped create a gorgeous farm full of ponds, fish, trails, pastures, barns and glass greenhouses. We built everything with local help but bought pieces from all over the country and Paris to give it both a rustic and glamourous vibe.

It was there I realized my love of design and beauty. Nothing is more beautiful than nature and I learned an appreciation for color and hue, lighting, natural materials, shapes, form and the intricate and complex beauty of plants.

From that experience, I learned how to do everything from designing outdoor spaces with the elements of fire, wind, sun, and earth, concepts that I use today. I designed, built and decorated the main house, the guest house and the greenhouses. I created outdoor meditation and entertainment spaces, including a Gulfstream guest space. I observed and was inspired to take the lessons I learned from building barns, greenhouses, tree houses, and a farmhouse into building and designing homes, which is what my company does now.

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?

I had this huge plot of land and my original idea was clearly not going to work. I had the space, I had already done quite a lot to upgrade it in many ways, and since it was an investment, I had to make it work for me. There was never a big decision, I just realized this was the path that had opened to me, and I was going to make the best use of the opportunity possible.

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?

I used what I learned about sustainability and tried to take existing structures and making them more beautiful. I love the concept of wabi sabi which loosely interpreted talks about the beauty of imperfection. That’s why I use old wood, old metal and old anything and try to repurpose it. I recently went dumpster-diving for old walnut wood that was headed for the landfill.

I have worked on houses from the ground up, to redoing townhomes. I just kept going, creating beautiful, functional, well-designed and fun projects, and as long as there was an audience for this, I continue to create new projects all the time. I also learned a LOT about being flexible! Recently I ordered a spiral staircase for a project and it came in the wrong direction. They said it would take three months to make me a new one, so on the fly I had to redesign two rooms to accommodate the error all in one day. That is just a small thing, but it carries an enormous lesson. It’s just another way to say take the problems and turn them into assets.

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

I have just finished five projects. All in Pittsburgh, except for the Lake House I designed and created for my own family. I have two grown up children, and a husband who is a pilot, and we like to go there to decompress, and have enough room to invite our extended family and friends.

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?

My husband and kids are an enormous source of inspiration and support, but my main support system has always been my closest friend. Having one person you trust more than anyone, always seeing the best in you and always believing in you when you don’t, that is what feeds the soul. If I fail, and I do, she never thinks less of me. A very deep and philosophical old soul who alone gives me the confidence I lack sometimes. She has been there for my first chapter and my second chapter, and has helped push me to make the difficult decisions time after time. She was very into my turning The Farm into a luxury property, even though I had no clue at the beginning. She knew how I loved to master new things, and she kept assuring me it was all going to be a success, even in my darkest moments when I kept thinking I had made a terrible mistake.

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

I think the interesting stories all come from the people I surrounded myself with during the creation of the Farm, and my work after I had finally sold it and realized I wanted to take all that I had learned, and apply it to many different applications and projects. I think my Lake House was the most interesting experience in my evolution. It is a compact space and I wanted find ways to make the most of small living. Take a limited space and turn it into a place that could serve a large number of people without compromising their comfort, the beauty of the project and the setting, making it a place for relaxation and camaraderie.

The wildest thing that happened to me on that project involved a freelance painter at the Lake House who robbed me and stole all of my equipment. I did not know that building a vacation home could be so dangerous!

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?

I still struggle with believing in myself, it is an ongoing process. I think you can be confident in one area of your life and insecure in other areas. Sometimes my insecurities switch from year to year but I always have some.

I guess the most recent example of overcoming a limiting belief would be talking about myself in this article. I am not comfortable talking about myself so much, but at the same time, it is good to get out of your comfort zone and put yourself out there.

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.

The five things I wish I knew when I started my design career:

  • Don’t sweat the problems, they sometimes turn out to be the best part of the design.
  • Anticipate that delays will occur, things will be out of stock and you have to be flexible at all times. You are not in control of a lot of what happens
  • After a long project, take time to refresh. You have to hit the reset button. When I am done with a project, I almost always think, this is too damn much work, why do I do it? And then 3 days later, I am ready to start a new one.
  • You will fail, and it will help you reach for success. You need to know what does not work for you, and then you can find what does work.
  • “What you do does not define you. It is what you do, not who you are.” Loving what you do does not mean loving every aspect of it. There are days that you will just hate it and weeks when you will hate it. That’s life.

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?

If I could inspire a moment now it would be for people to stop trying to prove that others are wrong and really really really listen. I think people are angry because they feel that they are not heard nor validated. In life, in business, in relationships we all need to talk less, listen more. It is true with clients, friends, families and everyone. People need to know that you hear them. I think our country is in the position it is because no one wants to truly listen to the other point of view.

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. 🙂

If I could meet anyone in the US right now, it would be Mike Bloomberg. I believe that he represents both sides of the aisle and at his core, I think he is a very good decent person. He has accomplished so much and seems to really care about people. I find him to be kind, respectful and incredible.

How can our readers further follow your work online?

Follow me on Instagram @dormerdesign

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

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