To: All the Jobs I've Loved Before

The fifteenth one

Before we dive in, I want to give a BIG & special shoutout to my three most engaged subscribers—@Sukanyaneslo0, @lauraluuu24, and @desireelynno—who have opened and read every one of my columns since we started this journey in February. Thank you so much for not only subscribing to my corner of the internet but also for taking the time to read my posts. Your support truly means the world to me! 💜

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Hi, hey, hello–I’m getting some much needed closure.

So I've been doing some emotional housekeeping lately, and I figured writing a few letters to my exes—well, ex-employers—might help me clear out some of the clutter. Think of it as my way of tidying up the mess left behind after my time there. And yes, Ariana Grande might’ve inspired this! 😏

One taught me love

One taught me patience

And one taught me pain

Now, I'm so amazing

Say I've loved and I've lost

But that's not what I see

So, look what I got

Look at what you taught me

And for that, I say

Thank you, next.

My dearest WeWork,

¹You were my first BIG girl relationship, the one that made me feel alive in ways I hadn’t known before. I still remember the day you asked me out; I felt butterflies in my stomach. You seemed to offer everything I was searching for at that moment in my life—a boost of confidence, a vibrant and thrilling world to step into, and the chance to explore new adventures I’d never imagined.

Our first days together were a whirlwind. You moved so quickly, always with a new project to dive into, a new challenge to conquer, a new journey to embark upon. Every day was an adventure, and I was swept up in the excitement. In those first few months, I accomplished more than I ever thought possible. It was exhilarating, like nothing I’d experienced before.

You introduced me to some incredible people who inspired me and pushed me to be my best. With you by my side, I felt unstoppable. By the time our first anniversary rolled around, I was confident in us. I had grown so much in that year, and I was ready to keep growing, to keep pushing forward with you.

But then, something changed. It felt like you pulled away, like you no longer saw me the same way. The projects we had brought to life together started to feel different, as if they no longer mattered. The wonderful people you’d brought into my life slowly faded away, and the vibrant world we shared lost its color.

And then, without warning, you ended it—through a text message, just like that. I was heartbroken, lost, unsure of how to move on or even if I could. I never had the chance to say goodbye, and maybe this letter is my way of doing that now.

I’ll always treasure the time we shared and the memories will stay with me forever.

With love,
Dre

WeWork was really a fun time for me! Great people to work with, great office space to take selfies in, & great opportunities to share my story 💙

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Rakuten,

²What a strange time it was for us to start something new, wasn’t it? I was still healing from my breakup with WeWork and adjusting to the new dynamics of starting a family. And then you came along when I least expected it.

To be honest, most of our time together feels like a blur now. Looking back, I realize I wasn’t truly ready for a new relationship, even though it was something I needed to keep going. I don’t think we ever really found our rhythm, never quite on the same page.

I know I was the one who ultimately called it off, but a part of me wishes you had fought harder to keep us together, to not let me slip away so easily. But maybe that’s the thing—we were both distant. Neither of us really put in the effort to make it work. And at that time in my life, I just didn’t have the energy or motivation to give it the chance it deserved.

Want to hear something funny? I was looking through my photos and I couldn’t find a single picture of us together. I guess that says a lot about how we were never really right for each other, or maybe that we were never fully committed. We just couldn’t see each other for who we truly were.

Sometimes I wonder if we had tried a little harder, given it a bit more time, maybe we could have created something beautiful. But I suppose we’ll never know.

When I walked away, I wished you the best, and I still do. I see you here and there, popping up on TV, and it’s a nice little reminder of the short time we shared. I’ll always remember that.

Take care,
Dre

Dear WeWork,

We crossed paths again a few months ago, and it was great—you were great! I had forgotten how amazing it felt to be around your energy. It was almost like we never parted, and I have to admit, I kind of liked it. It's nice that we can be cordial and friendly, without any ill will or animosity between us. I still cherish the times we shared and the experiences we had together. Whether we see each other again or not, it’s comforting to know that we’re in a good place.

Of course, WeWork had a reunion—called WeWorked—and of course, I went! It was fantastic to reconnect with these amazing people and reminisce about the wild times we had together 💙

#Commercial Break: This fall, Tiny Talks 2.0 is back with a twist! I’m reviving Tiny Talks from 2020, but this time with a fresh writing flair. Every week, I’ll be looking to YOU for creative writing prompts and interview suggestions. Whether it’s writing a Dr. Seuss-inspired poem at a café in my wedding dress or interviewing the first person I see walking their dog, I’m game! Just reply to this email (or leave a comment if you’re reading this on the Substack app) with your ideas, and I’ll bring them to life.

Dear Peloton,

I have to admit, you didn’t catch my interest at first. While you were pursuing me, my attention was actually on someone else—someone I’d been drawn to for years. But when that connection took longer to materialize than I anticipated, I decided to give you a chance, and I’m so glad I did. You turned out to be exactly what I needed to regain my confidence.

You gave me the space to grow in my craft, to take risks, and to truly take ownership of everything I did. With you, I felt the freedom to explore things I never imagined I’d be able to do. You also encouraged me to prioritize my physical health, something I’d never really focused on before. For that, I’ll always be grateful.

There was always that little uncertainty between us, wouldn’t you say? We’d have great, open conversations where you promised the world, and I vowed to meet you wherever you wanted to go. But when I wasn’t in the room with you, it felt like you forgot all about me. No matter how much effort I put in, it never seemed like enough.

And when I’d see you in person, it just didn’t feel the same. I never quite fit in with your friends, and to be honest, it was hard being the only one who looked like me in the room. I don’t think you ever really considered how isolating that was for me. I tried so hard to be like you, to talk like you, to act like you, to watch your favorite tv shows—it was exhausting. And with all those feelings, I still saw you as a significant part of my life—I even introduced you to my daughter.

³You made it clear you didn’t feel the same way. Just after we hit our one-year mark, you ended things, and I was devastated. I cried—something I’ve never done before.

Through every joy and disappointment, success and failure, moments of acceptance and moments of feeling completely unseen, I’ll always cherish the time we spent together and how you helped become the person I am today.

Yours truly,
Dre

Peloton was the first time I truly saw myself as a working mom! I'm so grateful I got to include my daughter in bring-your-kid-to-work days, and I'll always be thankful for the habits I developed there—in both physical fitness and professional growth 💙

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Dear Rakuten,

I saw you the other day but made sure to stay out of sight. It was surprising to see you so close, as I always thought of you as being far away. I didn’t stop to say hello because I wasn’t sure if you’d remember or even recognize me.

Dear Smile On Me,

⁴Actually no, I’m not ready yet.

Dear Peloton,

I still keep tabs on you, is that weird? I thought it would be tough to watch all the amazing things you’re doing without me, but I’m genuinely happy for you. I even log in almost daily to take your classes and maintain the habits I developed while we were together. You’d be proud. It's funny, even after all this time, I still catch myself trying to impress you. Anyway, I have a big milestone coming up soon, and I was wondering if maybe we could celebrate in person?

I'm close to hitting my 300th ride, y'all! It still amazes me that I'm this girl now. I used to go to the gym and watch my friends work out while I ate cookies! You can find me on the Leaderboard @HotMessDre 💙

1. Before WeWork I was a nonprofit girl. Working at incredible organizations back in California and in New York. In fact, it was through a nonprofit opportunity that I ended up moving to New York. WeWork was my for corporate job and I was over the moon when I got the offer letter. And that salary increase, man! For those of you who work in the nonprofit sector, you know what I’m talking about. The benefits alone, whew!

2. I got hired at Rakuten just a few weeks after discovering I was pregnant! It was a whirlwind period, compounded by the pandemic, and I felt lost and uncertain about the future. Starting a new job while working 100% remotely and navigating my first pregnancy was incredibly challenging. After my daughter was born, I tried to manage for a month but ultimately decided to leave. Balancing work and motherhood was so overwhelming, and the work environment wasn’t a good fit for me, so I made the tough decision to part ways after 10 months.

3. I’ve never cried over losing a job before, even when I was laid off from WeWork during the pandemic. But this layoff hit me harder than any other, likely because I’m a mom now, and it affects not just me but my daughter and my family. I also felt a deep sadness because my insecurities about not being accepted seemed to be confirmed (even though that might not have been the case). When I found out about the layoff, it felt like a personal rejection, making me think, "Wow, they really don’t like me." (Yes, I’m a sensitive person, if you haven’t noticed. And yes, I want my employers and coworkers to actually like me!).

4. I don’t think I’ll ever be in the right space to write a goodbye letter to Smile On Me. For those who don’t know, I ran my own nonprofit organization for seven years before closing its doors in January 2024.