Uncomfortable Prayers

Why Playing It Safe With God Slowly Undermines Faith

It’s the day before Thanksgiving. We are in a season of severe disruption. A moment of transition marked by uncertainty and waiting. And not out of piety but mere desperation I have set aside a few days to try and quiet my heart through time of intentional contemplative prayer and fasting.

There is a little park near my in law’s home in Connecticut that I have found myself several times over the years. For whatever reason this little park with a trail (pictured below) through the forest and around the lake seems to be an annual meeting place with God. And while it is quiet, serene, and still all around me, it is chaotic, loud, and tumultuous within me. Thankfully in His presence there is no need for performance, but there is a need for honesty.

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And because my inward world is as “quiet” as Time Square I just begin to blurt out everything that my fragile heart is carrying. It’s a mix of “what is going on, why did this happen, what you are You doing, this doesn’t make sense,” and tears. Not the good old fashion Pentecostal intercessory tears on behalf of someone else, but the tears of grief, lament, exhaustion, and quite honestly fear. Afraid of what might happen next. Afraid that I can’t make it through. Afraid that I don’t have what it takes. And afraid that it will be like this forever.

As I searched for language, I fell back on the ancient practice of praying the Psalms. I began praying through Psalm 13, the psalm that asks the haunting question:

“How long, O Lord?”

That question feels like the truest language for this moment. It holds the ache, the waiting, and the unresolved tension of a long obedience. Years of saying yes. Years of living in the space between promise and fulfillment.

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As I prayed through the psalm, something unexpected surfaced. I became increasingly furious. A holy anger rose up in me, as if to say, “Wait a minute, God. You are able to show up now. So why haven’t You?”

I began to call on Him to show up now and not next week, or next month or even next year. As I am quite literally yelling in this quiet forest, I was realizing the propensity I have to just lean in to waiting, surrendering, and submitting. None of these are wrong but it was almost as if the Spirit was challenging me to stop playing it safe. Yet, this moment didn’t seem to be about a lack of surrender, but the emergence and presence of trust through audacity and boldness. The boldness to say I know who You are and what you can do. Do it! And please do it now!

As I prayed, it struck me that I couldn’t remember the last time I had prayed like this for my own needs. I have spent much of my life believing courageously for others, standing boldly in the gap for their prayers, while rarely allowing myself that same audacity. Through my tears internally, I asked why. Why am I just now, in my thirties, beginning to place raw demand for supernatural intervention on my own behalf?

The answer that surfaced surprised me. It seemed tied to childhood. In a way my childhood trained me to assess probability before I asked. How likely am I to receive a yes? That question quietly governed when and how I made requests. I learned to pick my spots, to ask at the “right” time, to minimize disappointment. Hearing no felt too risky. So I developed mental strategies that made asking feel safer.

And here I am now, doing the same thing with my Heavenly Father, who loves me intimately.

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I’ve realized that many of my prayers have been shaped more by probability than possibility. I ask for what feels reasonable, what feels safe, what feels survivable if it doesn’t come through. I pray in ways that allow me to remain emotionally guarded. These prayers sound faithful, but they quietly keep my heart protected. I will stand in “faith” and ask for what feels reasonably achievable, rather than audaciously asking for what is ridiculous and miraculous. It’s subtle, but it’s control. It allows me to say, “I believe God” and “I’ve prayed,” while never fully offering Him trust. These are prayers that sound spiritual, but are quietly masked in unbelief and fear of disappointment. Praying past probability means risking disappointment. It means trusting God not just with the outcome, but with my heart if the answer is no.

Today, I choose something different. I choose audacious faith. I choose to believe God not for what is probable, but for what is possible. I choose to ask without calculation and without reservation.

I choose to grab the hem of His garment without permission. (Mark 5:27-34)

To interrupt His teaching like the four friends lowering a man through a roof. (Mark 2:3-12)

To relentlessly pursue Him like the Syrophoenician woman who refused to go away. (Mark 7:24-30)

In all of these scenarios these individuals accessed the heart and power of Jesus in moments that seemed at best ill timed and at worst inappropriate. Yet in each moment they are not met with hostility or a spiritual etiquette class by Jesus. Rather they are met with conversation, compassion, presence, and supernatural power.

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The type of prayer that disrupts reveals a heart that says, You’re my only answer. This is evidence of true trust. This is evidence of great faith.I have often viewed disruption as inconvenience, as annoyance, as interruption. Jesus sees it as beautiful faith.

I pray this posture reshapes my parenting. My sons ask me constantly for whatever comes to their mind (a dinosaur, a world cup trophy, a Ferrari), not because they want to bother me, but because they trust me, and see no limit to my capacity. Help me to see every ask, not as an interruption, but as evidence of trust.

Lord Jesus heal the areas of my heart and past that have suffered disappointment. Give me the courage to ask again, seek again, knock again. May my faith rise to the level of your ability. May I return to the place of fervent, bold, and audacious prayer that is not worried about hearing no or not yet, but is delighted to bring every petition and request to my Father who loves it when His children ask.