2023 Reflections
- Jill Matlow
- Jan 27
- 6 min read
Updated: 5 days ago
“There is a road, no simple highway...”

I think we can all jump for joy and breathe a sigh of relief that 2023 is almost over. I wanted to end this year on
a high note, especially as we begin setting our goals for 2024.
Speaking of goals, ironically I never set them. What I do try to accomplish instead is becoming a better version of myself either personally, professionally or both. One area of my life that I had identified that “needed work” was setting better boundaries, something I think most of us have struggled with from time to time.
As a reformed people pleaser, I’ve had difficulty most of my life saying no and then immediately regretting my decision afterwards. This really came to light this past year.
With the ongoing chaos in 2023, I came to the realization that due to my lack of setting appropriate boundaries, when it came time to finding the energy I needed for self-care, my “emotional love tank” was on zero. I had hit rock bottom.
Can you relate?
We over-commit, over-promise, say yes to projects, social engagements and commitments and before we know it, when we finally have time to exhale, it’s already too late.
We think we learn our lessons, but seem to repeat these behaviors over and over again, with the same results. And we all know what the definition of insanity is.
So how do we remedy this?
A very good friend of mine had offered me this sage advice which is so simple. “Sleep on it,” she once told me.
Sounds easy enough in theory, but for some of us, the impulse to reply “yes, that sounds great” automatically slips out before we know it and we’re filled with instantaneous regret and dread as a result. As people pleasers, we don’t like to disappoint others.
I decided to take to heart what my friend said and slowly but surely, it’s working its magic. Another great response is “Let me think about it and get back to you”. Works like a dream! Sometimes we have to get out of our own way to see the light. I’m happy to report that my “emotional love tank” is registering close to 100% these days.
“Daring to set boundaries is about having the courage to love ourselves even when we risk disappointing others” - Brene Brown
As you reflect back on 2023, what personal or professional achievement are you most proud of? As always, it was time for me to reach out to my fellow WSDaH Family members. I was curious to find out what they’ve been up to this past year and how taking a different path has led them to great success. I’m always so inspired by their personal and professional stories and I think you will be too.
“In the vast tapestry of life, moments of profound transformation often serve as the threads that weave our personal narratives. For me, 2023 stands out as a defining chapter, marked by a decision that would reshape the fabric of my existence. After 35 years in the bustling embrace of the New York City area, I took a leap of faith and relocated to Georgia, embarking on a journey that would reconnect me with family, redefine my understanding of authentic love, and open my mind to new ways of living and making a living.
A lingering desire for change, coupled with the need to rediscover the authenticity of family bonds, became the catalyst for a decision that would prove to be both daunting and liberating. The decision to be closer to family wasn't just about physical proximity; it was a conscious choice to weave the frayed threads of connection that time and distance had worn thin. As I settled into my new life, I found myself immersed in the comforting embrace of family dinners, shared stories, and the subtle nuances of familial love that are often overlooked in the whirlwind of life.
One unexpected source of support and camaraderie came in the form of the Wall Street Dead aHead Networking Family. Far from the concrete canyons of Wall Street, this eclectic community provided a bridge between my past life and the possibilities of my future. The group's commitment to fostering meaningful relationships transcended the boundaries of professional networking, evolving into a tapestry of friendships that added color to the canvas of my new life.
The year 2023 unfolded as a profound lesson in renewal and the creation of meaningful connections. It became a chapter of my story marked by the courage to embrace change, the wisdom to appreciate the authenticity of familial love, and the humility to open my mind to new ways of living and making a living.
As I reflect on this transformative year, I am filled with a sense of pride and gratitude for the personal growth and the rich tapestry of relationships that have unfolded. The decision to trade New York for Georgia was not just a geographical shift but a symbolic journey towards a life rich in authenticity, love, and the vibrant hues of meaningful connections.”
"Walk out of any doorway, feel your way, feel your way like the day before, maybe you'll find direction, around some corner where it's been waiting to meet you…
When life happens, outside of our control, some conversations can change where it's been waiting to meet you. In 2023, I had a conversation that changed the course of my career (and life) and set me on a different path. I was challenged to start my own company that would solve a problem that I alone could solve with my experience and do so using a large language model.
With that challenge presented to me, I did what I always do and creatively solved for that problem. I realized that my unique perspective and life experiences had brought me to this journey, becoming CEO and founder of my company Elain. I took my unique experiences and perspective and created a legal AI startup that will speed up the drafting and negotiation processes for complex transactional agreements. I had spent years in a biotech VC and then had exposure to large law firms and created Elain.
I have never been more motivated or excited to get started on this amazing adventure. I, and Elain, can't wait for what 2024 brings.”
Tami Erdfarb, CEO and Founder, Elain, Inc.
“When prompted with the question: ‘What am I most proud of this year?’ I sat quietly for a few moments and scanned in my mind for ‘big events’ over the past year that had occurred in my business, in my relationships, and in my band.
With over 5% of rate increases, the real estate business has been very challenging for some projects on the one hand, and producing some exceptional opportunities on the other.
And musically, my Grateful Dead tribute band Midnight Sun had some awesome gigs, but sadly our keyboardist moved to Ireland—we’re looking!
And in relationship land, my marriage feels like it has never been better as my wife Jen and I continue to work really hard with our Couples Coach on our communication skills, what Jen and I call our “super power!” This work has naturally helped me individually too, as I’ve fully embraced that while we can’t choose what happens to us, we can choose our attitude—so choose a good one.
So I suppose what I am most proud of this past year is the very positive and open-minded attitude I’ve chosen in response to learning recently that my Father is not my biological father! Turns out that my Mom and Dad were early in vitro fertility patients.
I ultimately signed up at 23&Me and sent in my sample. Three weeks later I got a message from 23&Me that Brian, who was “very” related to me, wanted to communicate with me. Wow. I accepted and proceeded later that day to have an amazing conversation where I learned: Brian and I share the same sperm-daddy, that he and four other half siblings—all quite musically inclined (including a graduate and professor at Berklee College of Music) had already connected over the last several years, and that apparently I completed the band!
I now have five new siblings! I’ve spoken with each of them individually, held a zoom call with all of them, and the other weekend enjoyed a wonderful brunch with two brothers, their wives and mine, my kids (26 & 29), and two twenty-something daughters of one of my brothers! So amazing!
I am proud of my response to this. Particularly as I watched how this news about my Father landed quite differently for my lifelong older brother with whom I share a Mom and grew up with, and with whom I’m very close! He and I will have to unfortunately ‘agree to disagree’ about this outcome, as he feels as though his origin story was erased and as a result became unanchored.
As my wife Jen likes to say, ‘we are the choices we make, and that’s the life we live.’”
Andrew Akers, Senior Advisor, Urban Investment Partners
What a year it’s been. Wishing everyone a happy, healthy, peaceful 2024. May we all walk along the road to success. “And if you go, no one can follow, that path is for your steps alone…”




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