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Jayne Portnoy of Pen2Paper: “Lead with love, compassion and honesty; None of those qualities will ever produce a poor outcome”

Lead with love, compassion and honesty. None of those qualities will ever produce a poor outcome. As a leader I believe your primary objective should be to grow your people and in doing so, you will achieve your business goals successfully. As a part of my series about strong female leaders, I had the pleasure […]

Lead with love, compassion and honesty. None of those qualities will ever produce a poor outcome. As a leader I believe your primary objective should be to grow your people and in doing so, you will achieve your business goals successfully.


As a part of my series about strong female leaders, I had the pleasure of interviewing Jayne Portnoy.

Jayne Portnoy, Founder of the Pen2Paper Project can be easily described as a brand coach, marketing strategist, speaker, yoga instructor and committed humanitarian. The Pen2Paper Project became her physical and analog reaction to a career in hospitality and wellness. Encouraging people to connect with each other and themselves through the art of letter and journal writing wasn’t just a passion project for her and the thousands of men and women that have attended her workshops — it was a necessity.


Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

I have had a career fueled in equal parts kismet and hustle, ranging from the National Football League to Fortune 500 hospitality and entertainment concepts. I have always had a passion to create memorable experiences and connections. Whether a sporting event, product launch, or Michelin starred meal, the driving purpose is all the same; to have genuine, passionate, creative conversations that lead to deeper relationships with ourselves and others. My love affair for being a pencil pusher began when it did for most angst-ridden teenage girls with a sparkly little journal. I mostly completed those pages with drama filled mood swings and to eventually abandon the practice when life, travel and the career got too big. Eventually social media became the place you shared your soul. We posted our workouts, check-ins, photos of food and ultimately our emotions gave way to emojis. It was when puppies turned to politics that I had to bid it all adieu. I returned the simplicity of letter writing and telling those that I missed — that I really missed them with long rambling sentences, doodles and consideration for each letter that hit the page. And so the Pen2Paper Project was born out of a desire to reconnect with people organically through analog tools, daily prompts and workshops.

Can you share the most interesting story that happened to you since you began leading your company?

Like nearly every business worldwide, the Covid19 pandemic has turned a program designed to gather people in groups and reduce digital diets on its head. Uncertain if Pen2Paper would still connect during these uncertain times, I have been invigorated by just how much people crave connection — even if there is a screen in between for now. Science has long proven the numerous benefits of writing, but to be able to moderate wellness, expression and comfort in real time is deeply rewarding.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

The mistake wasn’t entirely mine, but I was doing a television interview and the station misspelled my name to Porntoy (versus Portnoy). An honest mistake, but my parents were mortified and in the end everyone had a great laugh. It is also a great lesson in how powerful the written word is, and so easily manipulated into alternate messages. The honest mistake has inspired me to be a far more diligent observer and seeker of the printed word.

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

While shelves are lined with endless journals and many famed authors and self-help practitioners supporting the benefits of writing, there are few facilitators that support community and corporations in accessing easy and enlightening formats to get pen to paper. Each Pen2Paper workshop has its own unique theme designed to create an analog community, spark creativity and encourage ‘writing it forward’ as each workshop concludes with a letter. While I am a huge proponent of journaling, simply arriving at a blank page to perform the duty of gratitude or to data dump is an under utilization of the craft. The Pen2Paper Project invites you to the page to explore your lost memories, intensify the senses, rekindle your relationship with nature, and ignite the left brain to unleash itself into purposeful explorations of how our emotions can deliver on to a page when guided with compassion for the art form.

Are you working on any exciting new projects now? How do you think that will help people?

Yes. We’ve just announced a series of new workshops for June, in addition We’re excited to announce a summer series, A Nourished Spirit, paying homage to the cities, flavors, wines and spirits that enrich our lives and stoke our creativity. These mini workshops will feature some of our favorite shakers, makers, writers and creators and hosted on Instagram Live. The Pen2Paper Project has also launched the Pen2Paper PALS Project, connecting the Meals on Wheels community to avid letter writers. This program reaches those most isolated in Los Angeles and delivers companionship through the written word.

What advice would you give to other female leaders to help their team to thrive?

Do your best to dial down the negative talk you tell yourself. As women, we are more prone to imply our own hurdles and allow the voices in our heads to derail your ability to achieve your dreams. While this ‘trash talk’ is normal, I suggest surrounding yourself with honest, supportive and successful mentors that will assist you in navigating your path forward.

What advice would you give to other female leaders about the best way to manage a large team?

Lead with love, compassion and honesty. None of those qualities will ever produce a poor outcome. As a leader I believe your primary objective should be to grow your people and in doing so, you will achieve your business goals successfully.

None of us are able to achieve success without some help along the way. 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?

Annually, I do not set resolutions but instead establish ‘peopleloutions.’ I make two lists of people that I admire for their work ethic, success and impact on our world. The second list is of people that I believe will help raise my personal vibration, diversify my perspective and open my eyes to new ways to process the world. I work throughout the year to form mentorships, partnerships and true friendships with these men and women. I find it a far more rewarding way to kick off the year, as this deliberate practice has lead to significant friendships, support and personal and professional growth.

How have you used your success to bring goodness to the world?

I sit on the Boards of the Trotter Project and Careers Through Culinary Arts Project, both dedicated to providing education and culinary scholarships to underserved high school students both in Los Angeles and Nationwide. In addition to being a therapeutic wellness practice, the Pen2Paper Project also works with two Los Angeles chapters of Meals on Wheels to both raise awareness, funds and provide a personal connection with members of their community though the Pen2Paper PALS Project. This program is designed to reach the most isolated members of their community and connect them to friendship by putting pen to paper.

What are your “5 Leadership Lessons I Learned From My Experience” and why. (Please share a story or example for each.)

  1. Girl, Stop Apologizing. For years I found myself at the head of a boardroom table, making statements such as “this may seem like a bad idea or I hope you like this concept…” prior to presenting a solid, thoughtful, well articulated idea. I was so very interested in assuring the men and other women in the room were not put off by my ideas, that I would dumb them down in advance. It was a mentor that pulled me aside one day to point it out, and once I took notice, I realized that this is a constant for many women, even at the highest level. In a self-defense mechanism, we eliminate our good ideas before others can decide that for us. I started tape recording all of my meetings (thank you cell phone technology) so that I could actively listen to the way I spoke to others, spoke over or was spoken over. It’s a wonderful exercise and a great way to learn how to purposefully get you well constructed point across.
  2. Leap and the net will come. This is really not sound advice from a practical stand point, but quite possibly some of the best I’ve given myself. You will be the ONE person that will believe in you the most consistently in your journey. You will also be a steady oar in the waters of doubt. But the minute you start worrying about how you’ll pay for it, who will come, is the dream/business plan worthwhile, you begin to sabotage your dreams. Roughly twice a year, I sit with myself and a blank page and ask myself if I am still happy. Does the work I am doing seven days a week (because who really works just five?!) still fill me with joy? If not, that’s when you make change or bounce out. It’s a very honest time to sit with myself and navigate how to continue to move forward and still be in love with my dreams.
  3. Hire people that you want to leave you — I believe that the role as a leader is to constantly be moving people forward. I was fortunate to get an early hand up in my career and have always gravitated to leadership that was more interested in pushing me up the corporate ladder than stepping on me along the way. I go out of my way to hire, select and seek out partners and employees that have the opportunity to go further faster because I’ve had the opportunity to help them not only move up, but on.
  4. Don’t sweat the small stuff — Certainly not a new concept, but you will never regret letting go of the small moments that trip you up. The longer you hang on to them, the longer you give them weight and importance. The faster you can move on and past the hiccups, the quicker you will arrive at the successes that remain ahead for you to experience.
  5. Laugh at yourself more than others — I find the greatest leaders and thinkers also share the ability to laugh at themselves. Showing that you are human, flawed and honest doesn’t make you weaker or less than, but more so approachable, confident and tethered to humanity.

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

We write to taste life twice, in the moment and in retrospect.” Anais Nin. We spend such an extraordinary amount of our lives living outside the moment, that using my own craft to recall, savor and explore moments of the past and present so that they can be savored.

Some of the biggest 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?

Barack and Michelle Obama, so that I could deeply thank them for the courage, fortitude, grace and kindness in which they lead this country and how tremendously grateful I am that nurture the next generation in hopes we can be a better country.

How can our readers follow you on social media? @Pen2Paper_Project

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