Upgrade Your Disappointing Season from an Obstacle to an Opportunity

Have you ever been so sure about a plan? So expectant, hopeful and full of faith about something or someone only to be thoroughly disappointed?

Whilst reading Own Your Everyday by Jordan Lee Dooley, I was reminded me of how God kept me and the lessons we can garner through those times.

A Season of Epic Disappointment

After my uni graduation and smashing my degree with a first class honours in Business Entrepreneurship, I was buzzing, and ready take over the corporate world with my intrapreneurship skills. At said time, in addition to planning our wedding with my new fiancé, I had amazing plans for not just my career, but also bible college and ministry.

My plans however, were quickly replaced with disappointment after disappointment. Due to a change in circumstances, I wasn’t going to be able to go away and do my masters in Theology which I had already been accepted for and paid the fees. I didn’t get a refund. A job I accepted with the world’s largest building society was not at all I was promised it would be. I crashed my car and wrote it off.  One weekend whilst watching TV and delighting in a plate of homemade duck in plum sauce with mash, I randomly fainted multiple times and ended up in hospital. That day I was home alone, scared and thinking I was going to die because I didn’t know what was happening to me (dramatic I know). Between faints I tried to get out of the house to find help. I’m not sure how much time went by but I woke up sprawled out lying on the pavement in front of my home, light-headed but alert enough to notice that I was covered in my own pee and it was trickling down the street (yuck, I know. Sorry or the details but I need you to know how much this seasoned sucked).  This led to all sorts of hospital examinations plus being banned from driving for one year in case the episodes re-occurred. After my fainting episode, I was physically drained, felt weighed down and burdened for months. In my mind, I was myself but my body wasn’t functioning as it should. I had burnt out. Serious burn out. And that was just half of it! I don’t tell you all of this for pity, I just really want you to get that in a nutshell, this was not what I had planned or hoped for and it continued to be a season of epic disappointment.

Disappointment & All Her Cousins That Come With Her

I checked for the definition of the word disappointment and I got this:



  1. sadness or displeasure caused by the non-fulfilment of one’s hopes or expectations.
  2. a person or thing that causes disappointment.

plural noun: disappointments
Synonyms for the word disappointment are (a.k.a her cousins): sadness, regret, dismay, sorrow; dispiritedness, despondency, heavy heartedness, depression; distress, mortification, chagrin; disenchantment, disillusionment; displeasure, discontent, dissatisfaction, disgruntlement, failure, let-down, non-event, anticlimax; misfortune, setback, blow, reversal, body blow, one in the eye; fiasco, disaster, catastrophe, washout, non-starter, lead balloon

Whoa! That is a lot of negative feelings we can encounter when we are disappointed. But can I just say this, if you’re feeling disappointment today, hope is not lost. With Christ in your life it never will be.

Blog for Christian Women about overcoming disappointment


When You Have No Plan B, God Dares You

In Jordan Lee Dooley’s book Own Your Every Day, in chapter 5, called ‘Over Coming Disappointment with A Different Perspective’, Jordan  shares about a time when her man was expecting to be drafted for the NFL. She explained how undeniably talented he was at the sport and that Matts agent and trainers had told him that within seconds of him being available for drafting, the calls would come rolling in offering him deals & contracts.

Friends and family had gathered at their home. They waited outside the room as Jordan and Matt sat with the phone, a notepad and pen to write down all the deals and offers.

The time came and 5 seconds went by. 5 minutes, 10, 15, 45 minutes passed and nothing. Online they watched as Matt’s peers announced their new teams and contracts.

To cut to it, Matt’s call never came and now his NFL dream was suddenly out of reach. NFL was plan A and they’d put all their eggs in one basket with no plan B. Matt tried his best to hold it together through the disappointment and Jordan tried too, but admits she cried a lot that night as she watched her loves dream evaporate.

Own Your Everyday by Jordan Lee Dooley

And I‘m getting to the bit I love, and really want to share with you and the whole point for this article.

Months later, still questioning the season of insecurity and uncertainty they were in – the season that was trigged by disappointment – Jordan writes this:

“I began to wonder if maybe God doesn’t give us answers because He dares us to spend less time trying to figure out what we’re doing and more time having faith in what He’s doing. Perhaps the broken pieces that come with disappointment, frustration, and failure prepare us for a purpose we couldn’t have dreamed up on our own. Maybe they’re the things we need.”

Yes! THIS! ??

That quote is like a whole sermon to a disappointed soul. “God dares us to spend less time trying to figure out what we’re doing and more time having faith in what he’s doing”

Jordan figured out that His ways are not our ways and if she only learned to have faith in Him, if she had that right mindset, she could look for the lessons and the blessings in the change and challenges she faced.

Jordan now hosts, SHE Podcast, and her mission is to equip women with the tools they need to live purposefully and reach their greatest potential. Jordan and her husband Matt are now business partners who work side by side from their farmhouse in the Indiana countryside — Together they impact the lives of thousands through faith and entrepreneurship. Had Matt got that NFL back then, maybe we wouldn’t see Jordan and Matt influencing the world as they are now. But I bet that at the time of the disappointment, they couldn’t have seen that God was going to do all of this through them. Exceedingly, abundantly, above all they could have dream or hoped for.

Maybe you’re facing a disappointment right now and you’re questioning why things haven’t worked out as you expected or hoped for. Or maybe you’ve experienced disappointment in the past. – Maybe you feel one or many of those other words related to the word disappointment.

You can’t avoid disappointment. None of us can. But we can choose how we respond to it. You can hold onto the feeling of disappointment or you can hold onto the hand of the saviour and let Him lead you with His love and into His promises for you.

For I know the plans I have for you plans to prosper you and not to harm you, plans to give you a hope and a future. – Jeremiah 29:11

Let Me Upgrade You

When I look back over my season of disappointment, it led to what I can only describe as a time of ‘resting’. Not just physical rest, but a time where I stopped and just reflected. A time where what ‘I’ thought mattered, was removed in order for me to see clearly, ‘what’ and ‘who’ really matters. Maybe sometimes when we feel something is key to our purpose, titles, academic achievement,  jobs, relationship statuses, business goals, platforms, cars, finances, approval of people, it takes the removal of those very things, to wake us up and remind us of where our purpose really comes from.

I don’t believe God wants bad things to happen to us, but we live in a fallen world so these things occur. But when I look back, I see how God used what seemed like an obstacle, as an opportunity to redirect and to propel me, not only to the next level in my life, but more importantly to a point where I took the opportunity to seek his face for peace, restoration, direction, grace and hopefulness.

The car eventually got upgraded, our wedding went off without a hitch & Yes, I’ve had a perfect bill of health since. Ministry is wonderful and I got a job I love, but God didn’t just allow me to go through those disappointments, just so those fleeting ‘things’ could be upgraded. He wanted to use that time to upgrade me. My heart and my mind and my faith in Him.

As Lysa TerKerust wrote: The tweaking of us by God in the quiet place is the saving of us in public” God is good. In all things. In all seasons. The easy and the trying. When we are sure of what’s next and when we are not. God is good.

Change Your Mindset And Upgrade Your Disappoint From An Obstacle Into An Opportunity

Next time you experience disappointment, when you can’t see things going the way you’d hoped, trust God because His vision expands all of eternity. When you’re unsure of what’s next, know that your Lord guides your steps. When you feel set aside, no that you are set apart. And when your options seem limited, remember that God can do exceedingly, abundantly above all you can ever ask or think.

When disappointment strikes and throws obstacles in your way, let God use it as an opportunity to mould and cultivate in you a heart that simply says, Lord, I know that your plans for me will surpass, excel and outweigh even the grandest of my disappointments.

Upgrade your disappointment from obstacle to opportunity

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