Disappointment: the ugly truth

Lately I’ve been thinking a lot about the trajectory of my life – the line or all over the place path it seems to be following. Actually, that’s only half true. More often it’s the trajectory of other people’s lives I’m thinking about these days. We all know comparison is a danger zone. Most of us have learned to embrace our own uniqueness for the simple reason that we’re stuck with ourselves. If we can’t be anyone else, why bother dreaming about becoming someone else? Sure, I had my angst-filled teen and college years, during which I deliberately fought this truth by altering whatever made sense at the time – makeup, hair, wardrobe, lifestyle, diet. You name it, I tried it. But I’m a little past dying my hair pink (no, you can’t see pictures), pretending to actually enjoy staying up until 4am, and opting out of meals to shed some pounds, thankfully.

For the most part, I’ve made peace with this idea. I am me, and you are you. I’ll never be you, and you’ll never be me. My hair is curly, unless I put a lot of time and energy into fixing it. My skin is pale – it requires extra care and precaution this time of year. You’ll often see me wearing stripes, because I’m obsessed, but hardly ever strutting heels, I’m already tall enough, thank you very much. The older I get, the more comfort I find in my own skin. I’m incredibly grateful for this. It’s a sweet gift time has unfolded for me, one little layer at a time.

Sure, I have moments where I fret bikini season or envy your perfectly golden summer skin, but the reality is I love food more than I care about how my thighs look in a swimsuit, and I’d rather my freckles come out and frolic in the sun than become a boiling red lobster. I have my moments, as we all do, but for the most part, I’ve come to love this Jessie girl, curls, height, sunscreen covered thighs and all. I love her depth, her courage, her vulnerability. I love her hunger – for food, adventure, community, and for life. I love her heart and all of her emotions. Whether it’s wild laughter or ugly tears, she shows up and she feels. I love that. I love who she is, and usually, I accept who she’s not. Again, I have my moments, but I’m galaxies beyond where I used to be. Except in one area…

It seems that 25 year-old Jessie is far less concerned with who she is than where she is. I’m not so threatened by who you are and how good you look but rather, by where you are and how good your life looks.

You can look like a freaking goddess in your string bikini that highlights your teeny tiny, utterly incapable of jiggling thighs as they glisten and glimmer from tanning oils that would turn me into a blistering tomato all day long, but talk to me about your 401ks, recent signing bonus of more than I make in a year, dreamy boyfriend, unlimited vacation, wedding plans, or the house you just bought, and we are no longer friends. Okay, we can still be friends, obviously. But you better believe the minute our conversation is over, I’m going home to pour myself a very large glass of wine and contemplate my life’s utter lack of direction and promise. That’s the only ever so slightly overdramatized ugly truth.

I’m assuming this is another layer of that sweet gift of self-acceptance and self-love that time has yet to unfold for me. If the first half of my twenties was about coming to love myself, quirks, curves, and all, perhaps the second half is about coming to love my life, accepting it’s unique trajectory, and finding joy in the process, the becoming, the mysterious unfolding of it all.

But whatever this thing is that brings instant bitterness to the taste of your life actually happening while mine stands still (and can we all please just go ahead and acknowledge that as the silliest lie ever? If we are breathing, our lives are happening, duh) I want to hunt it down and kill it. I want it dead, buried, and never to be thought of again, because I want to celebrate your growth. I want to applaud your success. I want to smile at all of the happenings in your life, whether it’s scoring your dream job or falling in love.

I want to be with you and for you—wholeheartedly. Not sometimes, all the time.

I want to cheer you on with my whole heart in every area of your life, regardless of what that area of my life looks like, or if it even exists at this point. I want my celebration and excitement and support of you to be unconditional, entirely unswayed to my location, income, or relationship status. I’m not there yet, clearly, but I want to be. That’s what’s got me thinking about trajectories. Not the shitty state of my own life. I actually love my life. It’s pretty freaking fantastic! I love my job, my ridiculously amazing friends, my adorable house, this gorgeous city I get to call home, and the wonder of this whole season I’m living. The reality is that I love my life, but I somehow find myself incapable of believing that truth when I hear about yours.

The funny thing about all this is that it’s as real as it is fake. My negative response to your success, happiness, or progress is an indication of something very real going on in my heart. But the proceeding assumption that my life is stagnant? That’s ludicrous.

My inability to celebrate your newest adventure, whether that be an upgrade in your job, relationships, or finances, is an enormous red flag signaling deep discontent, dissatisfaction, or worst and most likely of all, disappointment, in that area of my life.

Disappointment is a hazardous emotion. It lurks undiscovered in the depths of our hearts. It sneaks in when we get passed up for a promotion, stood up on a date, or during some other crappy experience that we quickly convince ourselves isn’t that big of a deal. The minute we assure ourselves, or even worse, others, that we’re unaffected by something we were expectant for either not happening or being less than we’d hoped it to be, we hand disappointment the key to the innermost parts of our heart. Without wasting a second, she moves in, sets up camp, and camouflages herself so well that we remain oblivious to her residence. She’s not an in-your-face emotion, like anger. Anger is hotheaded and impatient. Hiding isn’t her style. She’s explosive in nature and far more concerned with release than her length of stay. While disappointment is hungry for home, anger aches for freedom. Refusing to be ignored, anger floats on the surface. It takes fairly little to set her off, but her appearance is anything but discreet. Meanwhile, disappointment hangs out like a parasite, feeding on your dreams and sucking your well of hope bone-dry.

We can say we need to get over ourselves, quit being jealous of everyone else’s life, and learn how to celebrate others, but I think denial is about as effective at changing one’s attitude as it is at killing a real, live parasite. Ask anyone who has come back from traveling with a parasite. It’s not a joke, and it doesn’t go away on it’s own. Are you kidding? Your stomach is the all-expense-paid-vacation-on-a-tropical-island-resort it’s been dreaming of. You don’t ignore the organism living inside of you feeding off your insides and pretend the fact that you’ve lost twenty pounds and can’t eat or poop like a normal human is fine – you go to the freaking doctor. Denial doesn’t work. Whether it’s our bodies or our hearts that need healing, they aren’t going to find it without us first acknowledging their experience of pain.

If I’m going to be wholeheartedly for you, I need to have a whole heart with which to be for you.

That requires digging deep to uproot the source of the disappointment that’s keeping my heart segmented. Something happened. It wasn’t what I’d hoped, expected, or dreamed. That caused pain. That pain opened the door to disappointment. And that disappointment has been warranting simultaneous, halfhearted celebration and lament ever since. The first step is acknowledging disappointment, but it doesn’t end there. To kill the nasty parasite, we must identify the event that handed disappointment the keys and validate our heart’s very real experience of pain.

Perhaps that thing that rises up in me when I see yet another friend of mine pursued by the man of her dreams is not jealousy, but rather disappointment rearing its ugly head in the absence of something my heart has been longing for – love. And if we dig a little deeper, maybe it’s disappointment from the specific experience of coming to find out that the one I thought I’d spend forever with would prefer to spend forever with another, not another in particular, just not me.

And maybe that sinking feeling I get when I hear you talk about your new, custom-made, dream job isn’t bitterness or resentment, but rather disappointment from the number of times I’ve thought I found the thing I was made to do, only to realize I was wrong. Or more specifically, from rearranging my entire life and pouring my heart and soul into a job I felt so confidently passionate about, only to realize I hated it.

These are two completely different experiences of being expectant for something that ended horribly different and far more abruptly than I’d hoped. One may appear a brutal heartbreak while the other simply seems like the ordinary unfolding of life out here in the real world. The first scenario might lead you to compassion, while the second might have you thinking, get over it, kid – that’s called trial and error, and it’s how we all find our way out here. Or maybe both seem sadly unworthy of mentioning to you. But I’d challenge you to rethink that.

There’s an important and powerful saying pain is pain. We can’t compare our experiences of pain, just like we can’t compare our experiences of trauma. A minor car accident can be just as terrifying and traumatic as a head-on collision, a natural disaster, or even a bombing. If it hurts, it hurts. Our experience of pain is always valid for this simple reason: we lived it. Pain is pain. Disappointment hurts, too - regardless of how mundane the scenario or ordinary the appearance.

Disappointment feels like being robbed of your most precious possession: your future – or at least the one you’ve dared to dream.

Dreaming is risky business. It’s territory wandered only by the brave. We were all created for it, and walking in our destiny certainly requires it, but dreaming produces casualties, one of which is disappointment. I think those who dare to dream experience infinitely more beauty, life, hope, and abundance than those who don’t, but I also know they encounter more disappointment and loss along the way. A true dreamer will tell you it’s worth it, but they will also have to validate their pain in order to continue dreaming with a whole heart.

I want to be one of the brave ones who dares to dream with my whole heart just as much as I want to celebrate the unfolding of your wildest dreams with my whole heart.

Right now, I’m not doing either, at least not wholeheartedly.

I want to go after the things that are keeping me there, rather than believing the ever-appealing lie that I’m “over it.” Being over a painful experience is a socially acceptable way of saying we’ve just barely scratched the surface of the healing that needs to take place. It usually looks like having only sort of acknowledged that something negative happened to us, while we blatantly ignore the very real consequences of that pain and unlovingly pressure ourselves to move ahead, deeply broken, hugely disappointed, and extremely weary from pretending we aren’t.

This is true in any area of our lives, but this seems to be an easy example. That breakup may have happened a decade ago, I may have completely forgiven that person for unintentionally hurting me, and the whole thing may be something I literally never think about. But if I never dealt with the disappointment of that experience, the unexpected ending, the death of a dream, then I didn’t address a very real pain it caused me, and a piece of my heart never fully healed. I certainly don’t feel like I’m walking around with a broken heart. I’ve forgiven, forgotten, and moved on, like we all do. For the most part, that’s true. But when I find myself, a natural celebrator, cheerleader, and encourager, struggling to rejoice with you in this area, I know my heart is not yet whole.

This summer I’ve found myself faking smiles left and right. I have judged you for your happiness. I have resented you for your success. I’ve hidden behind snarky comments and used sarcasm to numb my pain. Cynicism is a safe place for the bitter. Pessimism is a comfy landing pad for the brokenhearted. But only if we want to remain broken, and only if we want to stay bitter. We can lament without landing there. We can grieve without getting stuck. Denying our disappointment, however, will keep us there indefinitely.

Unaddressed disappointment will always manifest itself in emotions like bitterness, resentment, or cynicism. They are ugly sentiments, but I’m grateful they emerge. They point me toward my unfinished healing. They invite me to become whole.

I want to dig as deep as authentic celebration and big dreaming require of me. I’m starting by acknowledging my heart, thanking her for being so strong, and apologizing to her for my lack of compassion, courage, and consideration. I’m inviting her to be real and giving her permission to feel whatever she’s feeling, because when I don’t, I stunt her healing, and even worse, I train her to bury her pain and to hide from the world.

I’m asking my heart to come out of hiding. I’m challenging myself to be unashamed of her mess. I’m choosing to journey with the brave into wholeheartedness. I know it will require terrifying amounts of vulnerability and patience and will likely get way uglier than I’m comfortable with, but I also know this:

My heart is worthy of wholeness.

As is yours.

Holy Wanderings

I recently heard a man named Jamie Gallaway say: "Sometimes in faith you don't know where you should be, but you know where you shouldn't be."

I was stunned. He practically summed up my seven years of following God in a single sentence. In my experience, I know when it's time to leave a place long before I know where it is I'm going. I also know I need to say no to something before I know what I'll be saying yes to instead. This has made for a dynamic journey. A path full of offshoots and mini adventures this way and that. Always moving and changing directions. Lots of transition and lots of time in-between. I recently found myself there again. I left my job because the Holy Spirit told me to. I haven't gotten a new one yet, even though I probably could and according to many definitely should, because God is offering me an alternative invitation - a sabbatical of sorts. But we'll talk more about that later.

The thing is, faith often looks foolish on the outside.

Like when you refuse to overstay when you hear God whisper, "leave." Or when you choose to stay, because you know the invitations coming you're way aren't from Him. It may look unwise or irresponsible. You may come across stagnant or inconsistent. But remember this:

Whether you leave in obedience without knowing where you're going, or you stay in obedience without knowing what you're waiting for, that is a radical choice. The kind only made by the wildly brave. The kind only made by the faithful.

So if they say you're a wanderer, because you never stay long - let them. And if they call you flighty, because you always change your mind - let them.

Wandering is movement away from the proper, normal, or usual course or place. Wandering is not keeping a rational or sensible course.


Wandering is radical obedience. Wandering is what the faithful do. Wandering is a natural response to something completely supernatural: following the Holy Spirit.

It doesn’t always make sense, it isn’t always easy, and it may not be popular or well received - but here, I hope to offer you permission to be in process, uncertain, and in between. Faith to believe that God is who He says He is: a good Father, a faithful lover, the kindest King. Confidence to believe that you are everything Jesus says you are: perfectly loved, passionately desired, always enough. Encouragement to hear His voice. Boldness to say yes to His every invitation. Courage to follow the Holy Spirit, whatever it looks like, wherever it leads. Hope to dream wildly with God and inspiration to co-create with Him.

But mostly, I hope to offer you permission, permission to be here - wherever you are in this season, this very moment.

Because if your journey looks anything like mine, you are in process, uncertain, and in-between. In fact, I think it's safe to say if you're human, you are in process, uncertain, and in-between. I want to crush the lie that says you're the only one living there. I want you to know you're in good company, that this place is full of fellow Wanderers. I want to talk about this place - the confusion and the fear, the questions and hope-deferred, the beauty and the majesty.

I want to cultivate a community of people who give each other permission to be in process by being public about it.

A community of people who are unafraid of being authentically human - imperfect and unfinished. A community that declares boldly to the rest of the world who our God is by living a life of radical obedience. A community that embraces uncertainty, trusts in God's goodness and faithfulness, and follows the Holy Spirit wherever He leads - whether that's to far away places or the deepest parts of our hearts.

I want to talk about Holy Wanderings.

So if you think you might be a fellow Wanderer, would you join the conversation? Chime in. Share your experience with us. I'd love for you to invite us into your story as I invite you into mine.

Here's to Holy Wanderings - whatever they look like, wherever they lead us. And to never having to journey alone.

Thanks for wandering with me,