For some reason a great number of folks have recently posted pictures from 2016– a total ten year throwback. Which got me thinking… I’m sure you’ve heard of the exercise where you write a letter to your younger self? It’s supposed to be therapeutic and to remind you that it all works out, your fears weren’t warranted or whatever you were stressing about back then you’ve miraculously solved. Not that everything is always perfect, but there is a way forward. And I guess it shows you how far you’ve come. So I thought I’d write a letter to my 2016 self and reflect back on what I was feeling then and what I was working toward and hoping for in the future.
In 2016 I was still toiling away at my corporate job in banking. I had to commute on the NYC subway every single day. Work from home wasn’t a thing back then. The bank I was with was under tremendous scrutiny so the office was a pretty stressful place. I had a 16 year old son who was living with his dad so I was commuting to see him during the week and seeing him every other weekend. I was dating, but had nobody serious in my life. My biggest fears then were being able to pay for college, job security, and wondering if I’d ever meet a great guy or remain single for the remainder of eternity. Fast forward ten years and this is the letter I’d write to my younger self…
Hey, Jen. You made it. The road was not easy but you’re here. And life isn’t what you would have expected at all. Let’s start with some good news. Both of your parents are doing well and in excellent health. Dad is still enjoying his pool time and his busy social life. He moves again but this time from a high rise into a gated community. Mom is working part time and loving every minute of it. She starts running with a new group of women and they go out together often. She is walking and hitting the gym. No big hurricanes will strike the east coast of Florida and they will both be safe and content. You’ll visit each of them regularly, enjoy their company, and the relationships will continue to flourish.
Sadly a worldwide pandemic will hit. It’s unthinkable to imagine but New York City, along with many other big cities across the globe basically come to a standstill. Toilet paper is a hot commodity. But don’t worry, you’ll have enough with the reserves already in your apartment. You’ll lose your job during this time which will be shocking but it will be temporary and ultimately lead you in a better direction. And you will contract the virus very early which will be a giant health scare. You will recover after a few weeks and be glad that you had it with no lasting symptoms. You will have so much downtime that you write like crazy and your novel will take shape. You decide to expand your online radius for dating and meet someone amazing. You spend a good portion of the pandemic together. Sadly though several family members will pass away from Covid and other reasons. Your family will support each other in grief.
Politics will remain a hot issue. Whereas before you never really paid attention to what was happening, you tune in obsessively and begin to doomscroll. The news cycles get so intense that you cancel your cable subscription just to avoid the latest. Horrific things happen in Washington and the country devolves with a lunatic as the leader. I wish there was better news to report but this becomes a part of everyday shock culture– worrying about the survival of our country and our personal safety and liberties. Also worldwide events take a scary turn. Jews are again targeted in the most dramatic way and the results are heartbreaking.
Ten years is a long time and your body goes through a few changes, Jen. In the wildest news ever, your pin straight hair develops a little wave. I know you can’t believe it but I swear this happens. You gain a little too much around your middle and finally take action to shed those unwanted pounds. For a bit this goes well, until you rebel and gain a few back. You make peace with yourself and your body. People will tell you that you look younger than your age. You contemplate a lift, a tuck and some surgical assistance but instead opt for minimal aid for the fine lines around your eyes.
Some family relationships will tragically fracture. This is an agonizing development. I’m sure it’s unthinkable to read this news. You’ll surround yourself with friends that feel like family to help you cope. There is still some contact, but you will learn to live with a heavy heart. The pain of this will affect you every single day, but you will also find great joy.
The man you started dating during the pandemic turns out to be the love of your life! He’s everything you’ve ever wanted in a partner and you grow so close spending quality time together. You don’t move into the same home but instead keep both residences to have a City life and a country option and travel a lot in between. This works out famously. He is brilliant, funny and kind and he loves you for the exact person you are. You create a healthy interdependence and each retain some freedom to live as you both like. You get the bling, but opt out of marriage– a decision agreed mutually. Being with him adds a dimension of fulfillment you’ve never experienced before. You feel grateful, happy and lucky.
The novel you were working on during the pandemic becomes focused and you finally publish your first book– completing a lifelong goal. You’re so energized by writing that you finally adopt the persistent advice of a dear friend and take the plunge to start a blog. This becomes an incredible creative outlet for you and after a few years you surpass 500 posts. You plan to turn this into a second book but only print one copy for yourself.
The man you’re dating used to live in France and you decide to spend a month there together for a workcation. You do an eyewatering amount of prep for the trip. This works out so well that you your month long getaway becomes a yearly pilgrimage and you become better versed on navigating Paris than New York. On your fourth visit there you score a complete impossibility. I won’t ruin the surprise but wow, you’re gonna love it! You blog about so many landmarks, shops and restaurants that you create a Paris database to house all the detailed information you’ve collected. Finally deciding to monetize your exhaustive research, you create your first travel app. You launch Jen’s Little Black Book: Premier Paris Picks in 2026.
Other travel is in your future, too. You find incredible beauty in Western Canada during a dreaded fishing trip. Yes, you get sea sick but you catch your very first fish and then immediately return to dry land. You even survive the scary sea plane flight. You discover an amazing farm to table restaurant in Vermont and you visit again and again with dear friends making cherished memories. You relish a beachy vacation in Spain that is picture postcard perfection to celebrate a milestone birthday. A visit to Seattle is legendary and you love spending time in Arizona, Texas, Chicago and Washington, D.C. I won’t ruin all the thrills in store for you, but you have wonderful times ahead.
As you feared, your corporate life is unstable and you end up bouncing around a bit trying to find a forever home. Your career does not go as planned and many sleepless nights are spent worrying about the future. But guess what? You figure it out. You are able to pay for college so good for you! The planning, saving and discipline really worked despite the job upheaval.
And after much internal debate, you make the leap and cut the corporate cord permanently. You parole yourself to freedom by launching your own firm. You can’t see it now, but you develop a great idea to synthesize what you’ve learned from every position you’ve ever held and create an ideal job description that perfectly fits with your lifestyle. The new role allows you to travel personally and professionally and you’re able to continue saving for retirement. Clients become friends and friends become clients. The flex from owning your own company lets you determine your work/life balance and this is life changingly positive. You can focus on creative endeavors and really spread your wings.
In a final shocking development, you decide to move. Yep. You cash out of your gorgeous apartment you worked so hard to curate. The move is actually your idea. And you’re thrilled to purge and edit while you transition. You plan to stay local but decide to rent in order to maximize the investment opportunity of the apartment windfall. And this is a smart financial decision. I’m proud of you for being brave. I know this was extremely emotional and that you were equal to the task.
So that’s all the tea, Jen. I know many of these claims seem outrageous… some super positive and some extremely sad. And that is life, right? So keep maximizing the good. Remain focused and manifest all that you’ve ever wanted for yourself. So many of your dreams really do become your reality. And take your time. Relish the moments that matter with loved ones. Always stop and appreciate where you are and who you are with– I know you will. I am your biggest fan. Love always, Jen
jenslittleblackbook.com 