Chapter One: The Fool's Journey

Cruel Summer Book Club creator Jillian Anthony has survived heartbreak and loss, but after a year of documenting her grief, she sees that the possibilities are endless.

I met Jillian Anthony in 2014 in New York City. Over the years, Jillian has been my colleague, boss, mentor and friend. She’s someone I deeply admire for her talent, courage, mystical-feminist energy and inhibition to let her freak flag fly. But her compassion is what makes her light shine so inherently bright. 

I witnessed her kindness and empathy when we were working together in the spring of 2017. I was recently dumped and devastated after losing my first real love. Jillian noticed I was crying — OK, bawling — at my desk and she comforted me. The next day, she gifted me a tincture of perfume oil that reads “Love Me” on the label. She said the oil wasn’t necessarily meant to attract anyone but to help me learn how to love myself, which is something I’m constantly working on to this day. 

It was a wonderful ritual to dab the potent, sensual oil on my skin and smell how the scent blended with my own natural musk. Wearing the perfume made me feel pretty and empowered. Yet, I was still overwhelmed with grief and all the complex feelings associated with loss. To process them, I turned to tarot — hard — and began pulling cards for myself every day to navigate these intense emotions. The cards and their teachings helped immensely and led me to create this newsletter. (More on that later.)

In June 2019, Jillian lost one of the most meaningful relationships she’s ever had. She’s survived several breakups before, but this one hit differently. She knew her grieving process would be long and hard, but instead of minimizing her pain she maximized it by creating Cruel Summer Book Club, a weekly newsletter that documents her healing journey and shares stories of other individuals who have loved and lost and have come out on the other side. 

After a year and some change (plus a whole lot of healing), Jillian has left New York and is driving around the country in search of her next adventure. When we spoke in July, I realized Jillian is the true embodiment of the Fool tarot card. She was feeling joyful and optimistic for her leap into the great unknown. But let me be clear, she’s no fool. After all the loss she’s endured, Jillian has grasped that life is filled with highs and lows. “The next time I grieve — and I will — I hope I can look back and see how I’ve grown and healed, and know that no matter how long it takes, I’ll be able to do it again,” she says. Grief is meant to be shared and Jillian is inviting everyone to her table. Read more about her journey — and her tarot reading — below.


It’s almost the one-year anniversary of Cruel Summer Book Club — a newsletter you’ve published every week. That’s a huge accomplishment, how does it feel?
Thank you! I’m very happy and proud of myself for sticking with a project. When I started, I was so sad and scared. I was really worried about being judged. But as time went on, I quickly understood that people care about and find comfort in Cruel Summer Book Club. I have loyal readers, and I especially love getting notes and emails from people saying things like, “This really helped me.” Those messages mean a lot. It’s what I set out to do — to create something that would make people feel at home and not alone in what they’re experiencing. 

Was your intent to use this project as a way to navigate your heartbreak? 
Breakups have always absolutely wrecked me. I’ve had six relationships that have mattered and I’ve never recovered from a single one in less than a year. I had and perhaps I still have a lot of shame around that. But I wanted to track my healing process and write about it because that was something I was looking for. I also wanted to normalize that this deep, emotional pain is something we all go through, if not at one point but many times in our lives. In some ways heartbreak is the most normal feeling in the world. It doesn’t feel that way when you’re in it — it feels like your life is over. It’s the same with death or any kind of loss, but people just don’t respond in the way I wish they would. You’re expected to behave the same at work; your friends check in on you, but then they drop off quickly. People forget the process is long. I felt like such a freak for having so much grief. I just wanted to bring attention to that feeling.

I’ve watched you dedicate your time, heart and soul to writing this newsletter and I feel like you’ve managed to find a semblance of joy in your grief.
The really healing part of this project has been speaking to other people who are experiencing so many types of grief. Every single person I talked to survived it. Most of them were able to tell me, “Here’s how this was actually really good for me and how it brought me to my next really happy stage.” Making these real connections, plus the fact that people trust me with their stories, has been the most joyful part.  

I wasn’t grieving when I first began reading your newsletter, although I’m very afraid of loss. I know heartbreak is always lurking around the corner, but by sharing your healing process you’ve made me realize that when it comes I can overcome it. 
That’s so nice. Something I’m trying to accept is that grief is coming for each and every one of us. It already has in a lot of ways and it is still to come. That’s not a negative life outlook; that’s just life. To love is to lose. I just wanted to learn how to forgive myself and not be ashamed to let myself grieve. What you’ve said is exactly what I hope people see. No matter what your situation is, it will change. It might take longer than you hope, but here I am a year later and I feel great! 

Since 2019, you’ve done so much personal work on yourself. Now, in 2020, you’re experiencing a different type of loss. You got laid off as a result of the pandemic. Has all the healing work you’ve done prepared you for this tumultuous year?
What’s interesting is with the pandemic, losing my job and all the devastation happening in the world right now, I would rather be where I am today than where I was ten months ago. I suppose anyone who’s had a truly awful year before 2020 would understand what I mean. That’s not to lessen the pain and grief so many are currently going through. But my friend and I — she’s also had a really hard year before this — we’ve both been like, “Bring it on! Let’s fuck up our whole lives!” When I lost my job that was a blow. It was my last bit of stability. I was very sad and mourned for a couple of weeks but I bounced the hell back! All the self work I had done definitely helped. And when it happened I was with my mother in Las Vegas. We were staying in a beautiful home with a pool. Talk about gratitude! I’ve actually been working a lot on thought control. My improvement from ten months ago is shocking to me.

How have you been combating negative thoughts and staying grounded? 
A big part of thought control is taking yourself away from the past and bringing yourself back to the present. In the now, there’s almost never any type of emergency. If I’m lying awake in bed at night thinking negative things, I have to remind myself that there’s not actually a problem. I’m fine. The reality is that I’m about to go to sleep in my safe bed! That sort of work has changed my life. 

This year is also major because you’re about to leave New York City, your home of eight years, and travel around the country from September to December. How do you feel about this ending and the beginning of a new chapter? 
I’m really excited! I love New York, but I’ve always known it’s not my forever home. A conversation with my cousin Adam changed my whole trajectory. He asked, “What are your greatest dreams for this year?” I told him I wanted to travel in Europe for six months. That’s what I was planning to do pre-pandemic, but instead I listed a bunch of reasons why I can’t. Obviously those reasons are very true but he pointed out, “You just told me your dream and then you shit on it for double the time you talked to me about it!” That was a real wake-up call. There’s nothing tying me down anymore. I’m going to interview some cities that might be my next home and hopefully meet some amazing people along the way to incorporate into Cruel Summer.

Cruel Summer On the Road! 
Exactly! This is also my first, big solo trip. I feel extremely called to be in solitude this year.  I’ll see friends and family along the way, but being alone and learning how to hike and camp by myself is a big reason why I’m going. 

I’m interested to see what you write after days and weeks of solitude. So many people are afraid to do things by themselves, but I think we need to start glamorizing the benefits of spending more time alone.
Yes! It’s also important to follow your inner most desires and mine could not point more clearly to leaving New York and having adventures alone. Also, taking risks and putting yourself outside of this “box” everyone says you belong in is also a huge form of self-care. Our lives can be anything we want them to be. I’ve lost so much, but now I’m free! 

To overcome loss takes a lot of patience and personal growth. I know tarot has been a helpful and comforting tool for you during the process. 
Wait, we need to talk about your gift to me! It was three months after my breakup in 2019, and we met for breakfast before work. I basically sobbed the whole time, which was very embarrassing, but you were extremely kind. You surprised me by gifting me with the Mystic Mondays tarot deck. It’s gorgeous, super feminist and has this incredible holographic side. It’s one of the better gifts I’ve gotten in my life because it introduced me to this new way of connecting to myself and working through grief. Tarot has taught me to talk to myself. When I’ve had questions or problems, I’ve often gone to other people. But it doesn’t matter what anyone else says — you need to tap into what you think. I love the deck so much and I use it all the time. 

That makes me so happy! Tarot is such a great practice for helping us tap into our personal power. Is there a particular card you pull the most? 
I’ve definitely seen the Tower card a lot. [Editor’s note: Based on the Rider Waite tarot deck the Tower represents sudden change, chaos, destruction and awakening.] I don’t fear any of the cards because I didn’t come into tarot with that prior knowledge or prejudice, but the Tower makes so much sense. I think it’s my year card. 

I think it’s everyone’s year card! 
I don’t fear it at all, I’m very friendly toward it. Especially because I’m completely embracing the change happening in my life right now. What about you? 

For me, it’s the Eight of Cups. It represents turning away from what no longer serves you, which I view as my ways of thinking, toxic habits and actions. With the Black Lives Matter movement, the election and climate change, this card really resonates for me in 2020. I view it as a chance to move forward and to create a better future. 
It’s a huge year of reckoning with ourselves and how we live — how we blindly live. I’ve definitely made mistakes and I am ashamed of the ways I have not acted. That goes for so many parts of our lives pre-pandemic, including the Black Lives Matter movement. They’re all connected and it’s all connected to racism, actually. This is a time for each of us, especially people with white privilege, to ask “How have I been living in a way that does not align with my values and does not represent who I say I am?” And the same goes for our work lives and our relationships with people of color. It’s definitely going to be a marathon, not a sprint. 

Exactly, it’s a slow process just like healing, and it begins with us asking ourselves those hard questions. Speaking of, are you ready to ask what’s in the cards? 
Yes, let’s do it! 


With the Knight of Rods in your past, it shows you’ve been spending more time doing the things that really light your fire. You’ve been focused on following your dreams and taking charge to make them a reality. I think this card represents you and how you’ve been thriving.

For the present, you’re getting the Eight of Cups, just like me! This is an emotional card and it’s fitting because you’re being called to leave New York and start fresh somewhere else. You’ve invested so much of yourself in this city, from your relationships to your career. To leave this life behind is bittersweet, but regardless of how difficult it may be, you know it’s a necessary step for your spiritual growth.

The Eight of Swords, a card for hesitation or feeling stuck, in your future tells me there may be some fear of the unknown or insecurities that are keeping you from truly seeing your potential. 

Yeah, although I know it’s the right thing, I am sad to leave the city. It’s such a crazy time in the world right now, so that’s also scary. The thing I’m most interested to know is if I’m putting my professional energy in the right project for the next six months. I have several different options for where I take Cruel Summer Book Club and how much I focus on it. That may be where the hesitation is coming from. 

What would need to happen for you to dedicate more time to your newsletter? 
The clear hesitation for me is that I’m waiting for the right moment to turn on my paid subscriptions. My newsletter has always been free, but it’s been a year and I’ve worked really hard on it. I do need to make it a source of income in order to continue. It’s all very confusing. I feel unsure how to do that. But once I do turn on paid subscriptions then that’s a commitment, you know? I’ve already been committed to it, so I don’t know what’s holding me back. It’s just an extra layer. 

But then you can turn your newsletter into a book! 
That’s my hope! All of these options are ahead of me and they’re all possible. I just have to buckle down and pick one. I would love to write a book based on Cruel Summer

I can see that in your future.
It’s in the cards!