Thanksgiving has changed my life many times over. Here, I wanted to share two different “the difference a year can make” stories, both that were sparked by a Thanksgiving and changed the course of my life, just a year later. Thank you for being here!
Thanksgiving 2017
My then-boyfriend and I spent Thanksgiving in Spain. The trip planned around my dad’s bucket-list experience of sailing from the Canary Islands to St. Lucia- the same route Christopher Columbus sailed.
Keep in mind, my dad was a Colorado man through and through. So while he was adventurous, he wasn’t exactly a professional sailer. But that didn’t sway him. That’s his personality in a nut shell! 🙂
Growing up, I studied abroad twice. A year in France while in high school, and a semester in Costa Rica. Both times, my dad took time off work to come visit me. So when he announced he’d be sailing this worldwide race, I knew I wanted to be there for him in Spain to see him off. He was always there for me and I wanted to be there for him.
Waving goodbye to him as he sailed away was one of the last times I’d ever see him, as he passed away a few months later. I’ll always cherish this.
After seeing him off in the Canary Islands, Adam and I went to Barcelona to celebrate Thanksgiving together.
We rented an Airbnb in the Gothic Quarter. In the mornings, before leaving to explore, I’d work on my small business. Even though I didn’t have much to show for it, I was still determined.
On that trip, I ran my first Black Friday sale to my small email list. The city had breathed a new fire in me and I was determined to start making this actually work.
I was constantly listening to audios on positive thinking and abundance. I remember even walking into the YSL in Barcelona promising myself that one day I’d afford a bag for myself (that would’ve bankrupt me at the time).
Instead, I splurged on blush from Chanel. To this day, whenever I smell that blush, I’m brought back to that place in Barcelona. Determined, scared, fired up and deeply knowing I was about to change my life.
Adam and I went to a cozy, delicious paella Thanksgiving.
The food was great, but our conversation was sobering. What had I done that year? What was I proud of? What had I changed since Thanksgiving the year before?
Honestly, nothing.
I wasn’t NOT grateful for my life, my family, my health and my relationship. But… is this really what life is supposed to be like? It felt like I was just watching it pass me by instead of LIVING it.
That Black Friday sale? It made me ONE sale. One $97 sale. While I was disappointed I had spent so much of our vacation working on a sale that only made me $97, that one sale woke me up to something.
It showed me that it was possible to have a life where freedom + income came in tandem, instead of working for your freedom via PTO.
I felt in my bones I was meant for more.
Between watching my dad pursue his own passions so fearlessly, my Thanksgiving revelation about how idle my life felt, and my mighty $97 Black Friday sale, I left Barcelona with a promise to myself.
I would give 2018 a whole new level of effort, output, and trust that I could do this. I would double down on trying things, say no to weekends out with friends, and do whatever it took to make this work.
If, a year later, I was again at Thanksgiving with this little business that had nothing to show for… I would close it up.
Flying home, I listened to “Me and the Sky” from the then-new musical, Come From Away, hundreds of times. (It’s a great female power anthem if you need a boost!) I was so ready for the Universe to come through for me.
But, the come down from my high hit me when I got home. Ever been to a conference where you feel like anything is possible just to get thrust back into real life and feel like it was all a mirage?
I prayed for a sign that I was on the right track and assumed it would come in the form of me making another Black Friday sale.
Instead, Cyber Monday rolled around with no additional sales. I was on my yoga mat, lost, about to go back to my non profit job. I looked at my email and saw a coaching program for emerging entrepreneurs by Emily Williams on sale for Black Friday. It was $5,000.
I thought about it all day at work. It’s not a figure of speech to say I didn’t have that money. I didn’t have it in savings, retirement, a trust fund, the stock market… nowhere.
All I had was a credit card. In what was one of the scariest things I had ever done, I ended the day paying for it in full. I was terrified, but more terrified of not keeping that promise to myself.
Thanksgiving 2018
2018 was NOT the year I had envisioned in Barcelona.
In a sense, it was the worst year of my life with the sudden and shocking passing of my beloved dad.
But even with his death, and perhaps even more so considering it, I spent the year absolutely determined to change my life. To live with intention and create a life I loved. Its delicacy was just throw in my face.
It was a year of the highest highs and lowest lows.
The lows: I spent much of the year crying myself to sleep, and sometimes actually unable to move from grief paralysis. I had to plan my own father’s funeral and somehow still function in society.
I was also in credit card debt for the first time in my life. My credit scored dropped. In my darkest moments, I feared I would end up on CNN as the poster child for an entitled millennial who ruined her financial future all because she didn’t want a 9-5 job.
But it did have the highs.
The only way I could cope with my grief was to work. To give myself hope that I’d somehow still have a good life.
By May, I was making more from my business, the one that barely made a dime for 2 years, than I was from my 9-5 job.
At about $3k/month at my nonprofit, it wasn’t a huge amount of money. But I had come so far.
That July, Adam proposed in Paris, which gave me hopefulness for our future. For the first time since my dad had passed, I felt optimism.
That September, I got up the courage to resign
It was imperfect; I didn’t have the savings I wanted. My credit card debt wasn’t paid off. I still had loads of student loan debt.
But I knew I was in momentum and felt like I had to trust myself to make it work. It was one of the best decisions I ever made.
My final day, ever, in the 9-5 world, was on November 9, 2018. (Pictured!)
A week before, celebrating 15 years on Broadway, Wicked hosted a Very Wicked Halloween party. Ariana Grande sang The Wizard and I, my favorite song in the show.
(This didn’t age too well now that she’s Glinda!) I listened to that female power anthem over and over in those final days of my job, reminding myself that I COULD do this. That anything was possible.
Thanksgiving itself that year was bittersweet.
As the first Thanksgiving without my dad, it was heavy. My sister Abby and I spent it together in NYC, watching the balloons blow up before the parade and watching Christmas movies.
But through the sadness, I couldn’t shake the sparkle in my eyes at what was around me.
I was newly self employed and the freedom was indescribable. Adam and I were planning our dream wedding. I had kept that promise to myself in Barcelona one year ago. And to top it off, Thanksgiving weekend ended with my first ever five-figure cash month.
I hope my story helps you see that no matter where you are now, you have the power to change your life. You are always one decision away from a whole different reality. No matter how impossible things feel, or how scary that path looks to chart toward what you really want… it is there for you.
Part 2
Thanksgiving 2021
It was the Monday before Thanksgiving. I hobbled across town to the chiropractor for my weekly prenatal visit. I was 38 weeks pregnant and still deep in work mode.
“If I can just make it until Thanksgiving,” I promised myself, “then I can go on maternity leave a week before my due date.” That’s what got me through.
I planned to stop working from Thanksgiving on, but wasn’t due for another week and was looking forward to finally decompressing and transitioning my business into mat leave mode.
Just two months before, my business had its first official seven-figure sales year. While I was pregnant. I worked my butt off to reach that point, and didn’t stop working to prepare for time off. My body was screaming at me to take a break.
As I got to the chiropractors, I checked my email on my phone. My heart sank as one of my Mastermind clients emailed, “change of plans.”
Her email tone was gentle and loving, as she explained that though she loved my Mastermind, she had realized she needed mentorship more directly in her industry (weddings).
My first instinct was that I completely understood where she was coming from, and I was willing to work with her to find a fair way to exit.
But then… I felt my baby kick and let out a sigh of exhaustion. Though I knew her decision wasn’t personal, I couldn’t help but feel a bit sorry for myself. I didn’t have the energy to find a replacement at this point in my pregnancy. This client had enrolled in the Mastermind months ago and just now was changing her mind.
The next day, Tuesday of Thanksgiving week, we had our final Mastermind call for that year’s cohort, before my maternity leave.
One of the members was going through it on the call. A completely normal part of entrepreneurship. I held space and supported her as she processed her fears, her frustrations with conversions not being higher, and her confusion about which decisions to make next.
Right after the call she sent me a voice note, “Leah, I love you but I’m scared about my business and am not sure if I want to continue on with the Mastermind after all.” My heart broke for her. I hated seeing her trip of her own momentum because of fear so we scheduled a call for the following evening.
Wednesday rolled around. Before my call with my wobbly client, a THIRD email rolled in from a Mastermind member changing her mind about the following year. That was the third member who had put a deposit + contract down for the following year months before, change their mind in a matter of days while I was 38 weeks pregnant.
While none of the conversations were hostile, I was extremely shaken up by all this if I’m being honest. It felt like my entrepreneurial nightmare was coming true. Clients changing their minds for reasons out of my control. Contracts being broken. And all of it happening during the most vulnerable time of my life.
(Looking back, this experience helped me find clarity about who is right for my Mastermind and who is not, and it’s actually why my Mastermind is entering its 10th successful round next year!)
That Wednesday night, after my call with my client, I told myself to step away from this just for Thanksgiving. Give myself some time to relieve stress and relax. Then, starting Black Friday, at 39 weeks pregnant, I could start fixing the situation.
My husband took me out for pizza that night to try and cheer me up. We went to bed early and looked forward to a cozy Thanksgiving at home with my sister.
And then, at midnight, I woke up to my water breaking…
I didn’t have much time to process what was happening. I was in full-on, intense and painful labor just about 90 minute after my water broke. The peaceful Thanksgiving I had envisioned and been planning on as I worked around the clock up until that point was obviously no longer an option.
But of course, that didn’t matter, because I was going to meet my baby.
I labored at home as long as I could, per my plan. My doula was over by 6 AM and I was in the fetal position in the bath tub with the shower running on me. For hours.
By the time I was ready to go to the hospital, it was around 11 AM on Thanksgiving. In NYC, where we lived in Columbus Circle. Along the parade route…
And just like that, there I was in full, active labor, 6 cm dilated, trying to get a cab to the take me the hospital, and trying not to give birth under Snoopy. 🤣
It was the best and hardest day of my life. But it all disappeared the moment I held my son in my arms. It felt like I had waited my whole life to meet him. I honestly still feel that way when I’m with him today! Four years later. Like everything led me to him.
Of course, I wasn’t giving a second thought to the client situations that had consumed my week up until that point. I barely remembered we even lived on planet earth, let alone felt bothered by small business snafus. It was just my baby, husband and me in our bubble.
Still, I wanted to share that part of the story today to give an honest look at how hard business can be. It can catch you during times when you truly feel like you can’t take it. But you CAN, you’re so much stronger than you realize.
And you can also turn things around quicker than you’d believe…
Thanksgiving 2022
It took me longer than I wanted to get back into my entrepreneurial groove post baby.
I took just 9 weeks totally off before I started partially working again, at around 10 hours/ week. Because I was able to work from home and on my own schedule, this felt okay to me.
And while it actually felt good to work in that sense that I felt confident at my job, I wasn’t quite IN IT like I had been before I became a mom.
I struggled with direction.
I started two new Instagram accounts (lol).
I wanted to burn down the coaching piece and create passive income only (though it would take me until my son was 18 months old to finally give passive a go, my only regret is not starting it while pregnant with him)!
I hated posting on social media because I never felt confident.
I felt like my sparkle had faded.
At around 6 or 7 months postpartum, things started to shift.
My baby started sleeping through the night. I hated sleep training but it did wonders for my mental health.
I started reconnecting with my husband after feeling lonely during the newborn stage.
We had a part-time nanny we adored (who now works in my business) and our son loved too.
Things started to fall into place.
During Thanksgiving week of 2022, I signed a lease on a private office space.
This was in a skyscraper across from our apartment. It had a view of the Hudson Yards skyline.
It was like my Pinterest board from college had come to life. But the only thing better than having a private office with a view in NYC, was having one that was for and funded by a company I started.
I started dreaming again. Of all the things I had when I started my business; travel, life in NYC, entrepreneurial success…
With that in mind, I put together a fun, original Black Friday sale. I put my client-loved VIP Days on sale and chose destinations around the world in which to host them.
Paris, NYC, Miami, Chicago… I made sample agendas for each locations and beautiful videos to accompany them.
This felt so profoundly me. Making these videos in my new beautiful office, with my baby at home with a nanny we really liked, was a delicious, needed season of early motherhood for me.
My baby’s first birthday was on Black Friday that year (after having been on Thanksgiving the year before).
Both my in-laws and my own family came to NYC to celebrate. We spent Thanksgiving watching the parade from our terrace, and then Black Friday celebrating my son’s first birthday.
And all the while? My Black Friday sale generated $86,000 in sales that weekend.
As painful as it was to go through all of that while I was days away from giving birth, I can look back and see that it was the right thing for all involved.
For me, it also taught me that hiccups in business are only as big of a problem as you make them.
At first, I was embarrassed that this happened to me. I felt like it was a reflection on me and that it wouldn’t have happened if I was a better coach/ entrepreneur/ whatever.
Instead, it actually is the reason my Mastermind is so strong.
This helped me realize who are and aren’t the right fit for this container. It also helped me step into more of a leader that can hold spaces for the right entrepreneur in it.
My Mastermind is about to go into its 10th round, with our retention rate still above industry standard, and wild success stories from it.
It’s in its best position yet, with curated members that I personally interview or invite and retreats that have been fine-tuned after 10 rounds of doing them.
I honestly have that experience to thank for why my Mastermind breeds such results for the right person.
