Grief, Loss, & Making Painful Decisions


Grief is weird. One minute I’m out with pizza and wine, the next I’m bawling in the fetal position.

“Welcome to an exciting life. That’s what you chose, my dear.”

This is what my therapist said to me, with a knowing grin, as I sat cross-legged on the couch and sobbed uncontrollably in her office last week.

I hadn’t seen her in three weeks. (She was out of town, in a camper van, traveling up the coast on a vision quest. I love her.) The weeks we didn’t talk were PIVOTAL for me. I moved into my new apartment, my previously amicable breakup took a turn for the worse, and I survived the day I’d been dreading… August 3rd, the day of my would-have-been wedding.

Considering the circumstances, I was actually doing pretty well during those three weeks. I focused on my well-being, and in many ways, I was happier than ever before. I was SO excited to update my therapist on my progress… until a couple days before we met, when GRIEF hit me. HARD.

I’ve always attached emotional meaning to significant dates. Well, this summer has been FULL of them: the day of my would-be bridal shower (June 16th), the day I got engaged (July 2nd), my would-be bachelorette weekend in Charleston (July 14th), and last but not least… my wedding day (August 3rd). All summer I told myself, “I just gotta get through August 3rd. It’ll all be downhill from there.”

On August 2nd, thirty-eight of my best friends from business school flew down to LA for the weekend (I srsly have the best friends in the world). We stayed in WeHo at the Mondrian Hotel, we partied (a lot), and I was sufficiently distracted during what could have been an emotional trainwreck of a wknd. I made it!

On Sunday, August 5th, all my friends departed to LAX. I was exhausted and honestly ready to go back to my new place and just chill by myself. I threw myself onto my air mattress (OMG don’t worry, I have a fab Leesa mattress now), and to my surprise… I started BAWLING. I didn’t even realize I was SAD.

There was a lot I needed to process that weekend, and I didn’t do the emotional work. (NO REGRETS btw, I had an incredible time with my bffs.) But you can’t just skip over grief. It’ll rear its head eventually.

Grief has a life of its own

Grief has a life of its own. You can’t make it go any faster, but you CAN prolong it by avoiding it (or in my case, interrupting it for the weekend).

So, there I was, in my unfurnished apartment, living alone for the first time, and FEELING even more alone. I starfished on the air mattress and cried my eyes out. A. L. O. N. E. I went from the highest high of a weekend to the lowest low. I didn’t leave that air mattress for two days.

(Btw, I’m literally OBSESSED with my new apartment. The moment I saw it, I KNEW it was *the one* – the place where I’d become a stronger version of myself and build my EMPIRE. But as I looked around that Sunday through blurred teary vision, I didn’t even RECOGNIZE the place. Where was I? How did I get here? Wtf happened to my old life? What have I DONE?)

I haven’t wavered in my decision to call off my wedding. With time and space, I’ve only become more confident in my decision. But that doesn’t mean I’m not mourning my old life.

Grief validates the things we love(d)

Some days I wake up feeling stronger than ever. Like if I did this, I can do ANYTHING. But that Sunday, feelings of immense loss hit me, seemingly out of nowhere. There were LOTS of tears. Lots. I watched like 10 episodes of Southern Charm. I closed the shades. I ordered mac & cheese from Uber Eats (duh).

I was really hard on myself. I felt like a loser, wasting my life away instead of going out and living it. So when I saw my therapist that week, I broke down because I thought I’d “backtracked” on all the progress I’ve made.

Her response? “It’s APPROPRIATE to lay in bed for two days after the weekend of your would-have-been wedding.” Hm, I hadn’t thought of that.

I didn’t just cancel a wedding, I also canceled the entire life I mapped out for myself. I lost my best friend. I lost my home. I kinda lost my mind for a little bit there tbh. And, the kicker… I shared it all with the entire worldMaybe I should have stayed in bed for longer.

I wasn’t backtracking. Grief is unpredictable; it does whatever the hell it wants. It comes in waves. Just when you think you’re moving forward, it pulls you RIGHT back in. Grief is anything but linear.

This experience taught me that the only way to get through grief… is to grieve.

Grief validates the things we love. It validates our capacity for love. The deepest grief is felt from the loss of something (or someone) we love. Far too often we carry our losses as burdens because we never process them. Grieving forces us to do the emotional work that allows us to march forward into the world as a stronger human being.

People miss out in life because they’re afraid to make a painful decision

I believe people miss out in life because they’re too afraid to make a painful decision. It’s not because they’re scared to make the wrong choice, it’s because every choice involves LOSS. As humans we’re programmed to HATE loss. Assuming we can’t tolerate the loss, we avoid making a painful decision, and thereby stick with the status quo.

Every day people ask me, stunned, how I had the courage to decide to call off my wedding. (I’ll get to that in a bit.) The flaw in the question is the assumption that making a painful decision (and facing loss and hence, grief) is harder than the alternative. In actuality, all this grief is worth it in the long run. It’s the alternative you should be worried about.

When it comes to decision-making, we have a bias toward the short-term

When it comes to decision-making, people over-weigh the short-term consequences of loss. Every decision involves some type of loss. Mine involved the loss of my love, my planned life, my best friend, my home, my sanity, and my pride (… just to name a few). But all of that’s temporary.

If I hadn’t made the painful decision, and moved forward with my wedding, what would I have lost in the long-term? Likely, the same list as above, except with a few kiddoes along for the ride. Or, maybe I’d dodge those losses and lose other things instead, like my lifelong well-being and happiness. When you think about it that way, doesn’t it seem like loss and grief in the short-term is better than the long-term?

(… and btw, all this emphasis we place on LOSS makes us forget about what I GAINED by making this decision.)

When you lose something, you make space for something else

Every time you lose something, it makes space for something else in your life.

This year, my life was at CAPACITY. If my life were a glass of rosé, it would have been filled 60% with building my business, 15% with T (my ex), 10% with friends and family, and 10% with self-care. Then I overflowed the glass with 5% for wedding planning and another 30% for massive anxiety and pre-marital doubts. (Clearly, my cup runneth over.)

Ok, so then I did it. I called off my wedding. That 5% of rosé that was wedding planning? It spilled all over the floor. The 30% that was massive anxiety? It evaporated! (YAY!) And the 15% for T? That was lost too.

Don’t worry, we still have more than 80% rosé in our glass (I mean, always.)… I had to dedicate 30% to grief and 20% to apartment hunting.

Obviously, I’m spilling rosé all OVER the place. But because I’m GOING THROUGH THE GRIEF, it’s now starting to take up less and less of my glass. It went down to 25%, then 20%, then 15%. Sometimes it goes down to 10%, and then back up to 20% (somebody keeps pouring me refills). I also found an apartment, but 10% of that rosé is dedicated to moving in, nesting, and making it home.

So let’s just say my glass is now perfectly filled to the brim (plus or minus a few sips, depending on the day). That’s a HUGE WIN, right? But it gets better. Someday soon, I’ll be done setting up my apartment. And eventually, the grief will subside as well. Humans are resilient creatures.

When that happens, my glass of rosé will only be 80% full. That means one day in the not-so-distant future, I can fill up my glass with NEW 2019 VINTAGE ROSÉ.

What kind of rosé should I get? 2019 Podcast Rosé? 2019 Yoga Certification Rosé? 2019 New Relationship Rosé? 2019 B/B Branding Course Rosé? 2019 Travel Around the World Rosé? IDK U GUYS! I need to do some taste testing! (What do U think? Lmk in the comments below!)

K sry, having too much fun w this rosé metaphor. Basically, when u lose something, u get space in your glass of rosé (a.k.a. life) for something else. You’re smart; you get it.

So, how did I get the strength to call off my wedding?

K, now back to the question you all keep asking me: HOW DID I GET THE STRENGTH TO CALL OFF MY WEDDING?

The answer is simple: I didn’t have a choice.

I can’t help but keep it real; it’s who I am (but u guys know this lolol). I’ve never been able to fake it (when I don’t like someone, it’s written ALL over my face). I won’t live in denial. I know myself well, and I can’t help but be true to who I am and what I feel. It’s hard sometimes, and it takes a lot of courage. But sticking with the status quo only APPEARS to be easier. To me, it comes at a great cost.

My entire brand is about “be a woman and to thine own self be true.” That means that sometimes you have to flex your female and GO AGAINST CONVENTION. We have a bias in our society that sticking with convention is easier, but that may or may not be true for you (it’s not for me, obviously).

When we don’t follow convention, we’re basically saying, “I know what OTHER people would do in this situation, but that’s not going to work for me, so I’m gonna do something different.” You have to know yourself DEEPLY in order to recognize this. I have the gift (and the burden) of knowing who I am, so I recognized that something wasn’t right and decided to go against convention (in this case, convention = going forward with my wedding as planned, not rocking the boat, not hurting the people I love, etc. etc.) I didn’t know what would happen next, bc CONVENTIONALLY, brides don’t call off their wedding with two months to go. But I had to follow my truth and trust that I’d figure the rest out later.

It’s especially hard for women to go against convention bc we’re bred to “be nice” from the moment we pop out of the WOMB (it’s rly amazing that female bodies give birth to human life btw, we’re fucking awesome, sry for the tangent my b). “Nice” women prob would have gone with convention and gotten married. They might need that first marriage to get to know themselves and realize something wasn’t working (nothing wrong with this path btw, it’s just diff than my own). Whatever your path is to getting there, I believe that once you sincerely know yourself… that’s when you really start LIVING. Being true to who you are makes life infinitely richer. Even if it means you have to go against convention, face loss, and grieve. That’s how you GROW.

My therapist asked, “What’s the difference between denial and serenity?” Nothing, I suppose. But once you know yourself fully, denial isn’t possible. The only way to get your serenity back is to face your truth. So ya, I had the audacity to not be “nice,” bc I refused to be in denial. It pissed some people off, because that’s what happens when you go against convention.

When you trust yourself, things start to fall into place

I don’t know what’s going to happen next and I’m not going to get ahead of myself. This isn’t what I wanted, it wasn’t in my plans, but sometimes in life, that works out (and it often does).

What I DO know is that once I started trusting myself and listening to that little voice inside (that we all have), the universe has rewarded me. Things just seem to be… falling into place. I’ve realized that’s what happens when you follow your gut. The best part is, I’ve never felt so in TOUCH WITH MYSELF AND THE UNIVERSE (I realize I sound like a massive LA hippie rn, & that’s bc I am). To some of you, it may sound like I’m losing it with this universe shit. Do u want me to do a post on spirituality? Lmk in the comments!

Anyway, I’m going to leave you with this:

It’s crazy how easy it is to switch up your whole life.

It’s crazy how easy it is to switch up your whole life. All you have to do is decide to.

Making the decision to call of my wedding was the hardest and most painful thing I’ve ever done. But all I had to do was DECIDE. Since then, my entire WORLD has opened up with new possibilities. I thought my life would be one thing, and now, it can be ANYTHING. I’m freer and more empowered than ever before. Yes, I’m still grieving. But as B/B reader Chastity told me, “the strong woman to emerge from this will be UNSTOPPABLE.” And that’s worth the grief and loss.

What decision are you avoiding in order to spare yourself short-term grief and loss? If you make a painful decision, it will be hard, and it’ll get worse before it gets better. But eventually, the loss will open up space in your life for the beginning of something new. I’m confident that whatever it is will be bigger and better than you ever thought POSSIBLE. It’s going to be an exciting life, if you choose it.

decision making brains over blonde

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  • cassandraAugust 15, 2018 - 2:11 pm

    annaaaaa!!!!!!! this post is amazing as always. thanks for putting it all out there for us. it helps more than you will ever knowReplyCancel

  • CailinAugust 15, 2018 - 4:13 pm

    This made me cry and laugh at the exact same time. Your Rose metaphor is spot on (“someone keeps pouring me refills”…dead…)I’m in the same place as you right now, grieving for my best friend and fiance and the life we had planned together but knowing that we could not move forward anymore pretending that everything was okay or going to be okay. I’m facing the same “wow, I’m so okay, this isn’t as hard as I thought it would be” and then then next hour I’m crying so hard in the bathroom at work that I feel like I can’t breathe. I want to fast forward through the pain and get to my glass having room for my new 2019 Vintage Rose…
    Love and light to you, always. ReplyCancel

  • KayliAugust 15, 2018 - 4:23 pm

    You’re a badass and this unbelievably hard decision you made will open up opportunities and chances you’d never have experienced. 
    Btw I think 2019 should be travel the world only condition is that I get to go ha!ReplyCancel

  • EllaAugust 16, 2018 - 3:27 pm

    Oh, lady, thank you so much for writing and sharing your truth. I am currently in the process of separating from my partner. We will have been together 9 years and I will be entering my 30s as a single woman. This sentence has scared the hell out of me for the past few months of navigating this difficult situation. 30 and single. 30 and alone? While everyone else within my circle is starting to get married, buy a house, and have kids; here I am, leaving mine. Your blog and Instagram are instrumental sources in my life right now. I felt so alone in the decision I made for myself because to others, it seems absolutely insane. And you know what? I am perfectly okay with that because after the decision was made, I felt lighter. If I have learned anything from this experience, it is to trust my intuition. I made a painful decision that will take time to process but I feel reinvigorated about life. I feel freer and I am so thrilled about whatever happens next.

    You are a badass babe, cultivating a community for other badass babes, and I raise my glass of Rosé to you and everyone else out their relentlessly discovering and pursuing their truest selves. xx,Ella ReplyCancel

  • AlexaAugust 17, 2018 - 10:40 pm

    Anna, thanks for this. This was one of the first days on which I  clicked a hyperlink to one of your articles and actually got to that tab with the article within a day! 
    It just so happens to be my dad’s birthday. He’s been gone for 12 years now – the 12 years in which I entered high school, went to college, graduated, started my first job, etc. I understand what you mean about difficulty during transition periods, and I think a lot of what you’ve written can be extrapolated to make sense in dealing with loss of many kinds. 
    I don’t have anything profound to say right now, as it’s getting late in CST and I have an early morning! I do want to say thank you though – many of us who read your blog and follow your other social media probably think it way more than we express it. 
    Also, I don’t think you can necessarily go wrong with your decision about how to fill up the cup (podcasts, yoga, travel, etc). I will say I took my yoga training with about 50 other women and a few men. It was the best money I’ve ever spent and one of the greatest experiences. I noticed trainees who had recently (2 years prior or less) undergone major losses were extremely vulnerable while studying. Yoga certainly opens then body and mind to realize deep seated emotions. Some of these yogis became very ‘emotional’ for lack of a better word. I imagine this process during a yoga training might help someone and hurt someone else, depending on each person’s healing process. To summarize, my recommendation about the yoga training is to hold off for at least a few months before potentially being put in a very vulnerable space. (Unless your comfortable with that!) In addition, try to spend some time with the teachers in the program before signing up, if possible. You’ll be with them for a while! ReplyCancel

    • Eve IravaniAugust 18, 2018 - 2:17 am

      Dear Anna I am sorry you have been through the wars and thank you for sharing you woes in such an honest and endearing way.  You have probably helped more people than you know.  After what you’ve been through (loved the Rose analogy BTW) and the resolute manner you made your decision this might be hard to hear but you are resilient and from what I see you know your own mind so far be it from someone unknown to you to interfere .. all this is is a perspective from an older member of your band of girls.  I have been married for 32 years – it’s one of those long haul deals and I don’t want to come across as smug because it’s not all been plain sailing.  I am incredibly thankful though to have weathered our storms together and we’ve had multiple challenges of being biz partners and then me getting sick so the poor guy has fulfilled his part of those wedding vows believe me! What I wanted to say was that 2 nights before the wedding I was about to call it all off.  There was all kinds of family shit happening with my newly married dad wanting to ring my stepmother (who I had not yet met) and my mom being in pieces and then the pressures of pandering to inlaws etc… and that’s BEFORE factoring in the terror of the actual wedding day.  I hated my dress and was only wearing it because it was a gift from my mom and all she could afford at the time.  My dad was supposed to contribute to the wedding but that was looking increasingly doubtful so I was entering my new family in hock to them which actually felt.. well, humiliating.  Remember, this was back in 1986 when female empowerment was not what we know today!  I had just completed my Economics degree, had dreams of becoming an investment banker and what was I doing at the tender age of 23?  Getting hitched that’s what.  Nailing my colours to someone else’s mast before I even knew what it was all about.  Why did I go through with not one but 2 ceremonies in the end? (We are both mixed race)   Because through all the tears and doubts I knew one thing for sure.  I absolutely loved this guy.  He was the one who encouraged me to go back to university and although it meant a 3 year separation, he bloody well waited!  He planned the whole wedding and I would do my part in the holidays when I flew back to England from Colorado. Forget all that though… it was when I told him I was bottling out and he gave me the tightest hug.  That’s when I knew I wanted to always have those arms around me and I didn’t walk away.  All I am saying is that you have had so much crammed into your rose glass including building up a business that it’s no wonder you needed to retreat.  Ask yourself an honest question: was it the pressure of the wedding itself weighing on you or did you call it off because you found you were actually not in love with T? Just saying.  In the pictures you posted of the two of you you seemed so happy.  I hope after the dust has settled at least you can salvage the friendship – but only you know if that’s possible and then time does its whole thing as well I know you can fill your time with work, friends, fam, yoga, going out etc. There are lots of people you can do something with but as they say there are not many you can do nothing with”.  In this day an age a relationship can be anything.  You don’t HAVE to be married for F’s sake! Maybe the whole wedding thing just came to soon at the wrong time.  Only fools give advice and this is NOT that.  It’s just another perspective.  Keep doing what you’re doing and making us boss ladies happy with your exhuberant and fun posts which also have so many practical tips too.  I enjoy your newsletter every Saturday (I live in England). Have a good weekend! Eve xReplyCancel

      • AnnaAugust 29, 2018 - 8:35 am

        Hi Eve, thank you so much for bringing your experience and perspective to this conversation!! What a wonderful note. It’s amazing how resilient we really are, isn’t it?

        The reason it took me so long to recognize that getting married to T wasn’t the right fit for me was actually because I had so many other things going on at once. I blamed my anxiety on everything else (graduating from business school, moving to LA, launching a company, planning a wedding etc.) instead of facing the truth that maybe this relationship/marriage wasn’t the right one for me. It was such a hard truth to face and I hoped it would be ANYTHING but that. The anxiety didn’t come two nights before (as is common with “wedding jitters), it was nearly a year of mental turmoil. Once I acknowledged my truth, I’ve been much happier (even if I’ve also been devastated at the same time). Yes, we were in love, we could “do nothing” together, he was my best friend, and we were happy. But that doesn’t mean it was the relationship that would make me happy forever.

        We do look happy in our pictures though, don’t we? We were. But I also had deep-seated doubts that I didn’t want to face. If anything, that demonstrates how much can really be going on behind the scenes when we look at pictures on social media.

        I’m so happy you found such an amazing man to share your life with. I can’t wait to find mine! xx Anna

  • Anna KateOctober 10, 2018 - 9:16 am

    Anna, this morning while cramming for an assignment in grad school, I took a distraction break and Googled “what calling off my wedding was like.” Because that is what I did a little over two months ago now. And I found you. I was looking for someone who had experienced the same gut-wrenching guilt and shame and sadness as me. I expected I’d probably find other people who had called off weddings, but what I didn’t expect to find was someone who’s story of calling off their wedding was so exactly like mine. Our reasons (a deep sense that we weren’t as compatible as I had thought), how many months until the date (2!), the post-decision conversations (“Did he cheat on you?” “But you looked so happy together!” “Remember no matter who you marry he won’t be perfect!” NO SHIT Rhonda (made up name, I find inventing fake names in fake arguments satisfies my internal turmoil sometimes hahah), wondering if your stress/anxiety was due to school/work stress and not major doubts about the relationship, and even your trait of being totally transparent and unable to fake it (like, I literally don’t get how some people lie? Sometimes I’m jealous of people who can temporarily divorce themselves from their true feelings; it would come in handy sometimes). I mean all of it. I have been living your life, just delayed by 2 months. (My wedding date was September 29.) My biggest struggle was not having a “good enough” reason. After traveling around the world A MILLION FREAKING TIMES in my head trying to solve it for myself and also satisfy everyone’s need to understand, I’ve come to the conclusion that you don’t owe freaking ANYBODY an explanation when you end a relationship. Mostly because it’s hard enough to explain it to yourself. If that’s the case, good luck getting anyone else to understand. It will only exhaust you and confuse you further. All I know was that I did NOT feel the way that I needed to feel to marry him. Period. I loved him, like crazy. He had invested so much in me. He had encouraged me, made me laugh, showed me love and grace, been my friend and confidante, so many good things. And yet, I couldn’t ignore this deep-seated feeling that I didn’t want to be with him forever. I also had the complication that our entire relationship was long-distance, so it was doubly difficult to see for myself that I really didn’t want to marry him. So very, very much shame wrapped up in that. It’s been brutal working through that. I have never struggled with anxiety or thoughts of self-harm but they hit me like a freight train through this. Thankfully I have a ridiculous support system and close friends, so I’ve coped well, but it’s been messy. My ex-fiance did not respond extremely well and hurting him was by far the worst part. There is something about hurting someone you love that just mutilates your soul. I don’t know how long it will take to heal from the pain of causing him pain. But I do have those moments like you said when you realize, “Holy shit, I went against convention, told hundreds of people who might judge me that I had changed my mind about arguably the most important decision of my life, caused temporary pain for myself, my fiance, and many others because I knew deep down that despite the pain it was the best decision for literally every person involved.” DAMN. Can we get a standing ovation? That is ridiculous. I’ve never been so grieved and distraught and hurt and lonely and scared, but I did the hard, right thing, for everyone. Thank you for bravely launching your story out there so that people like me could find it and feel a little more normal, a little more brave, a little more okay. We’ve planted seeds of sorrow, and soon we will reap joy.ReplyCancel

  • ElleFebruary 22, 2019 - 3:24 pm

    I NEEDED THIS, THANK YOU ❤️ReplyCancel

  • TaraJune 10, 2019 - 1:06 pm

    Thank you for this…. I called off my engagement in December and have felt the grief like no other. 100% know it was the right choice (for both of us) but processing that the babies, and settling in to family life are not right around the corner has been hard. Some days totally fine, other days it hits me like a brick wall. So thank you for acknowledging it and being so open, as its not something many of my friends understand. ReplyCancel


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