LL - A Career Journey
You want to know more about how I got here? Wow thanks, I’m flattered.
It’s actually been a crazy journey that’s extremely difficult to summarize. I’m sure someone blessed with the power of brevity could do it. I’m certainly not that person. So to ensure that I don’t get swept away with the details, I decided to stick to my tried and true “Takeaways” format. I will briefly give some context, list my key lessons in a succinct bulleted list and then brilliantly tie it all together.
My first job, I was 14 years old, and a party hostess at Chuck E. Cheese in Edison, NJ. And yes, I did have to don the rat costume from time to time. Not my proudest moments.
Takeaways:
Be nice to your mascots and costumed characters. Many people are not.
Most parents are in survival mode, be kind and helpful.
Children are animals. Most of them anyway.
I loved to plan and run parties, even at that young age.
The next 10 years were spent bartending and serving in quite a few restaurants. Outback Steakhouse, Bennigans, (Which if you’ve ever seen the movie “Waiting” (gif below) is based off THAT restaurant.) I finally landed at The Cheesecake Factory, where I would spend the next 6 years. Also where I would meet some of my best friends to this day. (Shout-out to Eric Ganz, Dennis Rebick and Scott Roffman.)
Takeaways:
I learned more being a server/bartender than in any of my future jobs.
It made me street smart, intuitive, humble, confident, and able to talk to anyone about anything.
I have a unique ability to forge intimate connections in a short amount of time.
Authenticity, humor and kindness are key tools to defuse difficult people.
If your kids, family, or friends ever come to a crossroads about what they want to do next, no matter what age they are, tell them to wait tables. Trust me.
I bartended and served my way through college, but when graduation came, I thought what most people did then…time to get a “real” job. My first real job was an executive assistant in a rinky-dink healthcare recruitment agency in New Brunswick, NJ. They were NOT a reputable establishment, and some years later went down for employee fraud. I was not a part of that.
Takeaways:
There are dead-end jobs. Learn to recognize them quickly and get out.
Sometimes the grass IS greener somewhere else.
Yet another lesson in how to connect with challenging personalities - Sales Edition.
I wanted out! It had been a forever dream to live in NYC. But it was just as expensive then as it is now, so I knew I had to land something big. I thought: “Some of the wealthiest people in the world live in NYC. Surely I can land a PA, EA, or house manager position.” You could say that Idid that pretty successfully.
For the next 3 years I was the right hand woman to Michael Douglas, Catherine Zeta-Jones and their two kids, Carys and Dylan. It was a defining chapter in my life. I was living my best life in NYC on someone else’s dime. Sometimes it didn’t even feel real; Summers in Spain, yacht trips to Greece, dinners full of celebrity faces on the most beautiful beaches in the world. It was truly surreal. Surreal and surprisingly exhausting. After a 3 year contract I was craving stability, work/life balance and an HR department! So with a happy heart and satisfied soul, I decided to move on.
When it comes to my personal growth, there was nothing more eye-opening than this adventure.
(Thank you for all of it, Michael & Catherine.)
Takeaways:
Most celebrities are flawed and somewhat removed from reality. They are also just regular humans looking for love and validation like the rest of us.
Biggie was right - Mo’ Money, Mo’ Problems.
What you read in the tabloids is almost always false. Be smart about who & what you choose to believe.
I leveled up my small talk game. Once you’ve held your
own at a table with Gordon Gecko, you can talk to anyone.
More invaluable lessons about dealing with difficult personalities.
Never again will I judge a book by its cover.
I have a tough, nearly impenetrable skin.
Most of all it confirmed what I needed to do with my life...I was a planner.
I left the Douglas job craving structure, so I quickly landed a job as the executive assistant to the COO of Hadassah. HWZOA, as it’s also known, is a Jewish non-profit that raised money for hospitals and medical care in Israel. It was a great job, but I wasn’t excited about it. I had just had the most incredible 3 years, and working in a cubicle for 8hrs a day, doing a 3hr daily commute, wasn’t really ringing any bells for me. I decided to start interviewing for celebrity assistant jobs again. I landed an amazing one, but two weeks after accepting I learned I had stage 2 ovarian cancer. 🤯Yup, a whole new job was in front of me, and I wasn’t too amped for this one. I won’t bring down the mood with the details, just know that I’m writing this today in remission for over 10 years, AND I have two beautiful boys that I conceived and carried to term with ZERO medical assistance. Life is good. ♥️
Takeaways:
Your body is a marvel! The most important tool you will ever
own. Take care of it!
EVERYTHING, even the shittiest stuff, happens for a reason.
When in doubt, check it out!
Everyday, I get to witness living, breathing proof that miracles are real.
Positivity is your strongest tool for getting through hardship.
There's ALWAYS a silver lining, sometimes you just have to squint to see it.
After thoroughly kicking cancer’s ass I returned to my job at Hadassah. They were absolutely incredible through all my cancer treatments, and I even came back to a promotion. For the next 4 years I was the EA and office manager to the CEO and President of Hadassah. She was a woman who can only be described as rivaling the likes of Miranda Priestley. She was brilliant, talented, beautiful and really freaking mean a lot of the time. Despite the backwards compliments and occasional HR violations, we made it work. We recognized each other's passions and motivations and were able to connect there.
Takeaways:
Keep trying. You can connect with anyone, just some people are harder to crack than others.
More lessons in dealing with fun personalities.
The only opinion that matters about you, is yours!
Women can be terrible to other women. Stop hating and hold open the damn door!
Speak up, you’ll never regret it.
I’m f&$*#!g smart, and I need to own it more.
I wanted to move on from Hadassah, and my chance came when a former Hadassah co-worker referred me to the lead recruiter for a little start-up called Trello. (Shout-outs to JillianLeitao-Hoffman and Carrie Marvin.)
Trello was a remote-first start-up (before it was cool) with a small “homebase” on Wall Street in NYC. At the time they were a little over 60 people, globally distributed and scaling fast. The founders were all young, brilliant, heart-forward people. Not only had they built a beloved product from scratch, they had cultivated an unrivaled team culture.
I was hooked after the 1st day!
I was with Trello for 6.5 years. I started as the Executive Assistant to the leadership team, but if you know anything about start-up environments, you’re never just one thing. Over the years I wore many hats - EA, onboarding coordinator, workplace exp. manager, offsite planner, swag wrangler, project manager. The real feather in my cap though... I was the glue that connected the team to each other.
Trello had brought me full circle.
Takeaways:
Cliche, but true...Choose a job you love, and you’ll never work a day in your life.
Always assume positive intent. You had a shitty convo with someone? Assume you got
them on an off day.
Be an active listener. It takes a lot more practice than you think. (Especially for us
‘energetic’ folks.)
Remote work life is the ONLY work life I want to live.
“Fix it twice.” Fix the problem in the moment, then find out why it happened, and fix it so it won’t happen again.
You’ll never regret going the extra mile for someone.
The biggest ROI comes from investing in your people.
In 2017 Trello was acquired by Atlassian. Now acquisitions can be unsettling and disruptive to both sides. Two totally different cultures and teams merging their practices can get dicey. It’s a prime example of “hoping for the best, but preparing for the worst.”
We got really lucky with Atlassian. They allowed us to remain Trellists first. Understood that our culture and our bond was just as important to our product as our kick-ass engineering. Most importantly, they knew that in order to be successful together we needed to be open to learning from each other. That’s what we did for 6 wonderful years.
In June of 2023, I decided I had achieved all that I could with this amazing team. It was time to apply all of these takeaways, life lessons and experiences. Which is exactly what I’m trying to accomplish with this blog. Gather with LL is my way of paying it forward. Honoring all the people who influenced, inspired, guided, supported and yes, even challenged me. Actually, especially those who challenged me.
I leave you with this…
Reading this back I have definitely smoothed over those messy parts. The moments where I doubted myself or let people’s opinion deter me from my goals. And I will show you that part of me too. The screw-ups are just as important as the successes.
So my final takeaway, as I enter this next chapter of my career - “Finding what lights you up is difficult, but worth every bead of sweat.”
Like Tom Hanks said in one of my favorite movies of all time -
“It’s supposed to be hard. If it wasn’t hard, everyone would do it. The hard is what makes it great!
