A Life of Honest Connection

I hope this Wise Up! series has been a meaningful journey for you.

Week after week, we’ve sat with James — the brother of Jesus — as he’s challenged us not just to know more, but to live differently.

And maybe you’ve felt what I’ve felt: that James doesn’t pull any punches. He keeps calling us to maturity.

He keeps pressing us to wise up — not with worldly wisdom, but with wisdom from above — Godly wisdom.

I hope, throughout this series, you’ve found yourself living with a little more of that wisdom —

You’re listening quicker
You’re speaking slower
You’re treating people with dignity
resisting the tug of greed or comparison
using your words to bless instead of curse
owning your faults
humbling yourself before God
and submitting to his leadership

Well today, as we wrap up this series, James ends with one last area where wisdom is essential — prayer.

So let me ask you as we get started today:

Why pray?
What’s the point of it?
If God already knows everything, what’s the point?
Can we change God’s mind?
Does he even care?

In our day we’re more connected than ever.

Email, texting, Slack, WhatsApp, AirDrop, Google Drive, shared calendars, live location sharing…

You can send someone a photo, a document, your exact location, and a GIF of a dancing banana — all in under six seconds.

And when it works, it’s awesome.

But sometimes it doesn’t…

This week I shared a document with someone through Dropbox — and they never got it.

No bounce-back message. No alert. Just… gone. Like it disappeared into some mysterious black hole in cyberspace… where all our missing socks and unread group texts go to die.

It’s frustrating. I did my part. I sent it. I followed the protocol. But I got no confirmation it landed, no idea if they saw it, no clue whether anything is going to happen next.

Sometimes prayer feels like that, doesn’t it?

Like you send something out into the universe and… nothing.

Like George Buttrick once said, “Prayer seems like a spasm of words lost in a cosmic indifference.”

He said that in 1942 — long before iPhones and Instagram and group chats and disappearing messages.

And here we are, decades later, in a world more connected than ever… and yet real connection — with each other and with God — often feels just out of reach.

We’re moving so fast.
We’re busy.
We’re tired.
We’re jumpy, anxious, overbooked, overcommitted, overstimulated… and somehow still behind.

And into a life that already feels maxed out — where exactly are we supposed to fit in time with God?

And even if we do find the time, the question remains:

Is anyone listening?
Is this anything more than talking to the ceiling?
Can we really get through?

So… why pray? Why bring our thoughts, our feelings, fears, or questions to God?

Let’s start here: Because we can’t help it.

Gallup reports that more Americans will pray this week than will go to work, work out, or even scroll social media — and that’s saying something.

9 out of 10 people say they pray regularly.
3 out of 4 say they pray every day.

And it’s not just Christians. Every faith tradition has some form of prayer.

Tribes throughout history have sung, danced, pleaded, and sacrificed before their gods for rain, or protection, or healing, or crops.

The Aztecs even offered human sacrifices just to get their god’s attention.

Muslims pause five times a day to face Mecca in prayer.

People in recovery pray to a higher power to regain sanity and peace.

Even atheists — when turbulence hits at 35,000 feet — tend to whisper something into the universe.

We pray in the hospital.
We pray at gravesides.
We pray for a test result.
For a job interview.
For a second chance.
For a way through.
We pray in joy.
We pray in panic.
We pray when we don’t know what else to do.
We pray because we’re empty.
Because we’re grateful.
Because we’re scared.
Because we’re desperate.

We pray because it’s instinct.

We pray when control slips through our fingers.
We pray because deep down, we all know — we’re not God.

This Wise Up! journey has been about developing God’s kind of wisdom…

And do you know where wisdom starts?

with humility
with a deep awareness of our need
with a willingness to say, “God, I don’t have it all together. I need help. I need you.”

That’s not weakness. That’s wisdom.

That’s the starting line of a wise life.

Search the pages of Scripture, you’ll find this deep instinct to pray everywhere.

From the beginning of the story, people cry out to God.

Abraham prayed.
Moses prayed — and even negotiated with God and changed his mind.
David prayed.
Nehemiah prayed.
Ruth prayed.
Daniel prayed.
Ezekiel prayed.
Elijah prayed.

And James, who we’ve been learning from these last few months, brings up Elijah in his final words. He says in James 5:17–18:

Elijah was a human being, even as we are. He prayed earnestly that it would not rain, and it did not rain on the land for three and a half years. Again he prayed, and the heavens gave rain, and the earth produced its crops. (James 5:17–18)

Elijah wasn’t superhuman. He was just like us — full of doubts, and fears, and flaws. But he prayed… and God listened.

Mary prayed.
Peter prayed.
Paul prayed.
And of course, Jesus prayed.

Over and over in the Gospels, we see Jesus sneak away to quiet places to pray.

He would get up before dawn.
He would slip away from the crowds.
He would retreat from the noise.

And there’s this moment in Mark’s Gospel when Peter finally finds him — probably out of breath and a little frustrated — and says, “Jesus! Everyone’s looking for you!”

And I imagine Jesus saying, “Yeah, I know. That’s why I came out here.” (And maybe — maybe — he also silenced his notifications for a few hours.)

But what’s striking is that Jesus — the Son of God, the One who spoke the universe into being — felt a deep, daily need to pray.

He had this rhythm of returning to the Father — of drawing strength, and clarity, and perspective, and peace from the Father.

It was in those times of prayer that:

He gained courage to face the cross.
He found wisdom to teach with authority.
He drew energy to keep loving people with radical compassion.
He stayed rooted in who he was.

Prayer wasn’t a religious box to check — it was a lifeline.

And if he needed prayer… how much more do we?

Do you know what’s fascinating?

Out of all of the miracles, all of the teachings, all of the jaw-dropping moments the disciples witnessed Jesus perform, do you know what they actually asked him to teach them?

Not:

“Teach us how to multiply bread and fish.”
“Teach us how to turn water into wine. That could really save us some money at weddings.”
“Teach us the walking-on-water thing. That was impressive.”

No, the one thing they asked was:

Lord, teach us to pray. (Luke 11:1)

And it makes sense.

Because these guys had grown up watching professional religious people pray.

They had seen the polished, public, theatrical prayers of the Pharisees — long, loud, dramatic monologues meant to impress others more than connect with God.

But when they watched Jesus pray… it was different.

It wasn’t a performance. It was a relationship.
It wasn’t a speech. It was a lifeline.
It wasn’t about status. It was about connection.

And they wanted that kind of prayer. They wanted what Jesus had.

And maybe that’s part of wisdom too — knowing the difference between prayer as performance and prayer as connection.

Because here’s the truth: real wisdom never tries to impress God.
Real wisdom just comes to God — honest, and humble, and unfiltered.

That’s what the disciples saw in Jesus.

And that’s what James saw too.

Which is why he could write in verse 16:

The prayer of a righteous person is powerful and effective. (James 5:16)

Why pray?

Because — according to James — prayer is powerful and effective.

Not because we are powerful.
Not because we use the right words or formulas.

But because the One we pray to is powerful.
And because prayer connects us to him.

Now, some of us hear this verse and immediately disqualify ourselves.

“Well, I’m not righteous. I’ve made too many mistakes. I’ve been inconsistent in my faith. I haven’t exactly been the picture of holiness lately.”

I feel that.

But here’s the thing:

James isn’t talking about perfection. He’s not talking about people who never mess up.

The Greek word here refers to someone who is right with God — and the only way we’re made right with God is through Jesus.

The righteous person is the one who comes humbly, not the one who comes flawlessly.

And that’s part of wisdom too, right?

To know we can’t stand on our own merit — so we come boldly, but humbly, through Jesus.

That’s what makes our prayers powerful — not our words, not our track record, but the grace of God.

And when we pray like that — honestly, humbly — it does something to us.

It resets us.

Let me explain it this way:

I’ve worn contact lenses since the sixth grade.

Every morning I wake up and I can’t see a thing. Everything is blurry. My world is fuzzy.

But then I put my contacts in — and suddenly there’s clarity.

That’s what prayer does for me.

Whenever I pray — really pray — it’s like putting in spiritual lenses. I start to see more clearly.

Prayer reminds me of who God is… and who I’m not.

It gives me proper focus. It sharpens my perspective. It helps me zoom out of my little world and remember that God sees the full picture.

And in a world that constantly blurs the lines — between truth and lies, good and evil, pride and wisdom — prayer is what helps me see clearly.

Last week James brought up Job from the Old Testament. If you know his story, you know how much he went through.

He lost his wealth.
He lost his children.
His body was covered in sores.
His friends weren’t helpful.

And for a while, Job holds it together. But then he just loses it.

He starts praying — not politely, not poetically, but honestly — “God, where are you? What are you doing? Can you even see what’s happening to me?”

It was raw. It was unfiltered. And it was unedited.

And guess what?

God shows up.

But not with explanations. Not with comforting clichés.

God shows up with questions:

“Where were you when I laid the foundations of the earth?”
“Do you know where I store the snow?”
“Have you ever given orders to the morning?”
“Can you loosen Orion’s belt?”
“Do you send the lightning bolts on their way?”

He goes on like this for four chapters straight — question after question. And eventually, Job just says:

“Okay… okay. I spoke of things I didn’t understand. I’ll stop.”

And what’s amazing is — God never scolds him for asking. He doesn’t shame Job for being honest.

God welcomes the honesty… but he also reminds Job who’s God.

And here’s the truth that hit me when I read that story: Prayer helps me reverse roles.

So often I come to God thinking he needs a performance review — that I have the plan and he should follow it.

But when I pray long enough… honestly enough… eventually I remember:

He’s God. I’m not.
He sees what I don’t.
He holds what I can’t.
He knows what I never will.

That’s the kind of wisdom James has been pointing us toward all along:

The kind that humbles us.
The kind that reminds us of our smallness… and God’s greatness.

Prayer is how I remember who’s really in charge.

And strangely enough, that doesn’t make me feel powerless — it brings peace.

Because I’m not alone in this life.
I don’t have to have it all figured out.
I don’t have to carry the weight of the world on my shoulders.
I have a God who can handle it.

We live in a culture that constantly distorts our vision — a culture that bombards us with noise, and hurry, and opinion, and spin, and distraction.

We’re told what to value.
What success looks like.
What beauty looks like.
What a meaningful life should be.

And the result is… it’s hard to know what’s real anymore.

But when I pray — really pray — it clears the fog. Prayer restores my spiritual vision.

There’s so much wisdom in the little phrase we’ve heard so many times from Psalm 46:10 where God just says,

Be still, and know that I am God. (Psalm 46:10)

That phrase “Be still” actually means to vacate. We get our English word ‘vacation’ from that word.

God is inviting us to take a break.

He’s inviting us to step away from the busyness for a while and let him be in charge.

He says, “You know what, I’ve got a great idea; why don’t I be God today? Why don’t you just go ahead and take the day off?”

And that might be the wisest thing we could ever do.

Because prayer isn’t just where we speak — it’s where we learn to be still.

And in the stillness, we remember:

We’re not in control.
We’re not the center of the story.
We’re not the main character.

But we are deeply loved.
We are invited into something bigger.
And we don’t have to carry life on our own.

Prayer has become so much more for me than a spiritual shopping list. More than “Here’s what I need, God” or “Please fix this” or “Make it better.”

For me — prayer is like putting in my contact lenses.

It sharpens my vision.
It helps me see clearly again.
It reminds me that I’m not the director, or producer, or scriptwriter.

This is God’s story.

And I’ve been invited — graciously, undeservedly — to play a small but significant role.

And I’ll tell you: That truth doesn’t shrink me. It frees me.

Because when I forget that, that’s when I start to get anxious.

I start trying to control everything.
I get wrapped up in how I’m perceived.
I try to carry more than I was ever meant to carry.

But when I pray — when I get still and remember who God is and who I am not — I find peace.

And that’s the perspective James has been leading us to all along.

A wise life isn’t about becoming more impressive. It’s about becoming more humble…more surrendered.

Prayer is what helps me remember that.

It’s interesting that James wraps up his letter the same way he started it — with prayer.

At the very beginning, in James 1, he said:

If any of you lacks wisdom, you should ask God, who gives generously to all without finding fault… (James 1:5)

And now, here at the end, he brings it home again:

Is anyone among you in trouble? Let them pray. Is anyone happy? Let them sing songs of praise.

Is anyone among you sick? Let them call the elders of the church to pray over them and anoint them with oil in the name of the Lord.

And the prayer offered in faith will make the sick person well; the Lord will raise them up. If they have sinned, they will be forgiven. (James 5:13–15)

What’s he saying?

Whatever’s going on — pray.

Trouble? Pray.
Joy? Pray.
Sickness? Pray.
Sin? Pray.
Whatever the condition of your life, the wise thing to do is… pray.

James talks about anointing with oil.

Some believe James is referring to the medicinal value of oil in that day; like — “pray and get medical attention.”

And I think that’s good advice.

But most scholars agree that this phrase ‘anoint with oil’ is probably more symbolic of the presence of God.

Definitely the oil is not some kind of magic potion you can buy at at CVS for $19.95.

This is not special prayer oil.

It’s not like you can’t pray if you’re out of prayer oil.

You can still pray.

He’s just saying — get some godly people around you. Get the presence of God there. And pray.

I could easily spend the rest of this message talking just about healing.

In fact, if that’s something you’ve wrestled with — or longed for — I want to recommend the book Prayer by Philip Yancey.

There’s a chapter on physical healing and prayer that’s thoughtful, biblically grounded, and incredibly compassionate.

But let me just say this clearly: I have seen God heal people.

I’ve prayed for people and witnessed healing that surprised doctors.

I’ve seen God lift someone emotionally or spiritually even when their physical healing didn’t come.

Sometimes, there’s peace. There’s strength. There’s a calm that you can literally see in their eyes.

I’ve also seen that some physical pain is tied to deeper spiritual realities.

Sometimes what needs healing isn’t the body — it’s the heart.

Maybe it’s unresolved guilt.
Maybe it’s bitterness that’s been buried for years.
Maybe it’s shame, or fear, or regret, or addiction.

And I’ve watched people begin to heal physically after they got honest spiritually — after they confessed something or released something they had been holding onto.

Prayer brings light into dark places.

And light always starts the healing process.

But let me also say this as clearly as I can:

There’s a distorted theology out there that says “If you have enough faith, you’ll always be healed immediately.”

And if you’re not healed? Well, clearly, your faith wasn’t strong enough.

I don’t believe that’s biblical. I don’t believe that reflects the heart of Jesus.

Even the apostle Paul wrote in 2 Corinthians that he had a “thorn in his flesh,” something he asked God three times to take away… and God didn’t.

Instead, God said:

My grace is sufficient for you, for my power is made perfect in weakness. (2 Corinthians 12:9)

Sometimes God brings healing.
Sometimes he brings sustaining grace.
Sometimes he brings both.

But he always brings presence.

And in that presence, there is peace.
And in that peace, we find wisdom.

Alright, so why do we pray?

Because Jesus told us to.

And because he told us who we’re praying to.

In Matthew 7 Jesus says:

Ask, and it will be given to you; seek, and you will find; knock, and the door will be opened to you. For everyone who asks receives; the one who seeks finds; and to the one who knocks, the door will be opened.

And then he gives this analogy that’s so simple, but so powerful.

He says:

Which of you, if your child asks for bread, would give them a stone?

No loving parent responds to a hungry child by saying, “Here — chew on this rock.”

And then Jesus says:

If you, though you are flawed, know how to give good gifts to your children, how much more will your Father in heaven give good gifts to those who ask him? (Matthew 7:7–11)

That’s who we’re praying to.

Not a distant force. Not a cold bureaucrat. Not an unblinking, inflexible deity.

But a Father who sees. Who knows. Who loves.

And like any good parent, sometimes he gives us what we ask for. And sometimes, because he loves us — he doesn’t.

As a dad, I want to say yes to my kids as much as I can.

But I also want what’s best for them — even when they don’t see it in the moment.

And when they’re hurting, or confused, or anxious — I want them to come to me.

I don’t want them to pretend. I don’t want them to perform. I just want them to be honest.

And if that’s how I feel as a flawed, limited human parent — how much more does God feel that way toward us?

Prayer is not about impressing God. It’s not about using the right words or crafting the perfect formula.

It’s just showing up. Humbly. Honestly. Continually.

That’s what Jesus invites us into.
That’s what James echoes.
That’s what wisdom looks like — trusting that God is both good and near.

Aright, let’s look at James 5:16 again:

Therefore confess your sins to each other and pray for each other so that you may be healed. (James 5:16)

You know what strikes me about this verse?

James doesn’t just say, “Confess to God.”

He says, “Confess to each other.”

Why?

Because healing doesn’t happen in hiding.

God’s design for healing almost always involves other people.

Now — this doesn’t mean we air our deepest struggles to everyone we meet in the lobby.

That’s not confession. That’s oversharing.

But every one of us needs one or two people in our lives who know the whole story.

People who’ve seen the backstage.
People who’ve been handed the keys to the vault.
People you trust enough to say, “Here’s the truth about me.”

Because in our culture — especially here in the Bay Area — we’re experts in image projection.

We curate our lives.
We manage perceptions.
We lead with strength.
We post the wins, filter the flaws, and keep the mess tucked away where no one can see it.

But wisdom says: Don’t live in the shadows. Come into the light.

And I’ll just say this personally — this has been a humbling season in my own life.

I’ve had to be more honest about weakness.
More transparent about failure.
More open about pain than I ever expected to be.

And here’s what I’ve learned — when I stop hiding, I actually start healing.

And when I confess — first to God, then to trusted friends and mentors — I’m no longer carrying it alone.

There’s a paradox here:

We hide because we fear rejection.

But hiding keeps us from experiencing love.

Because as long as I’m hiding, I’ll never believe you truly love me — not the real me. Just the image I’ve let you see.

But when I’m known — and still loved? That’s when I begin to heal. That’s when I start to walk in freedom.

So James is asking:

Are you willing to stop pretending?
Are you willing to get honest?

…with one another. And with God.

David did in Psalm 139:

Search me, O God, and know my heart; test me and know my anxious thoughts. (Psalm 139:23)

That’s a wise prayer. Not a polished one, but a wise one.

He’s saying:

“God, I don’t even know what’s wrong right now, but I know something is off.

“I’m not doing great, and I don’t want to fake it. Will you help me understand what’s really going on in me?”

And I’ve prayed that kind of prayer more in the last year than I ever have before.

I’ve had moments where I’ve sat in silence and said, “God, I don’t even know what to say right now. But I’m here. I’m listening. I’m open.”

And somehow, even in that silence — God meets me.

He doesn’t require eloquence.
He doesn’t need explanations.
He just wants the real me.

And friends — that’s a wise way to live.

Because God is the only One who can handle the whole truth about us — and still love us completely.

A number of years ago, we had this old car we finally had to take to the junkyard.

It had 180,000 miles on it, it made weird noises, and every dashboard light you can imagine was glowing — like a Christmas tree of mechanical doom.

So we took it to a mechanic, and they hooked it up to a diagnostic machine.

And for $1,100 — because it’s always $1,100 — we found out exactly what was wrong.

And I’ve come to realize: That’s what prayer is like for me.

Prayer is saying to God: “I need you to hook me up to your diagnostic machine.”

“Search me, O God… know my heart… test me… show me what’s off.”

Because sometimes I don’t know.

I know I’m tired.
I know I’m irritable.
I know I’m stuck.

But I don’t always know why.

And so I pray things like:

God, why are my RPMs red-lining all the time?
Why do I feel so anxious for no reason?
Why am I snapping at people I love?
Why do I keep reaching for things I know won’t satisfy?
Why am I addicted to productivity or approval or control?
Why can’t I sleep?
Why does my soul feel so restless?

Wisdom is learning to ask those questions.

Not just powering through.
Not just ignoring the warning lights.

And the amazing thing is — God doesn’t respond with guilt or shame.

He doesn’t say, “Wow. You again?”

No — he welcomes us in.

And when we ask, he responds.

Sometimes he brings clarity.
Sometimes he gently redirects us.
Sometimes he just gives peace we didn’t even know we needed.

But he always meets us.

So prayer isn’t about informing God — he already knows. It’s about inviting God.

It’s about saying: “Here’s access to the system. Run the scan. Do what you need to do in me.”

And that’s one of the wisest prayers you could ever pray.

C.S. Lewis wrote:

We must lay before Him what is in us, not what ought to be in us.

That’s what prayer allows.

Not the edited version of ourselves. Not the cleaned-up version we wish we were.

But the real version.

The one with doubts.
The one with baggage.
The one with anger, or shame, or loneliness.
The one who feels lost sometimes — even while leading others.

That’s who God wants to meet.

And sometimes, prayer for me looks like just opening the lockboxes:

The lockbox of regret
The sealed-away failures
The wounds I thought I was over
The shame I thought I had buried

I open them… and invite God to look with me.

Not to condemn.
Not to accuse.

But to heal. To cleanse. To set free.

That’s why wise people pray.

Not because we’ve got it all together. But because we know we don’t.

We don’t come with image management. We come with open hands and hearts.

And when we do — when we really do — something happens in us:

We stop hiding.
We start healing.
And we begin to experience the kind of relationship God has always wanted with us.

Not distant.
Not religious.
Not performative.

But honest. Intimate. Personal.

There’s this old hymn I used to sing growing up:

What a friend we have in Jesus,
All our sins and griefs to bear;
What a privilege to carry
Everything to God in prayer.

And that’s really it.

I can bring everything to God in prayer.

My worries. My wounds. My gratitude. My questions.
My hopes. My frustration. My desires. My doubts.

I can bring me.

Richard Foster calls this “simple prayer.”

It’s just talking to God about whatever is on your heart.

And here’s what that looks like for me: “God, I’ve got a meeting coming up. Help me stay calm, and focused, and kind, and present. Give me wisdom.”

In the middle of that meeting: “Okay, God… help me not get defensive right now.”

After the meeting: “Thanks, God, for whatever you were doing in that room.”

Driving home: “God, I’m about to walk into the house and I’m exhausted. But I want to love my family well. Give me what I don’t have in this moment.”

On a walk: “God, here’s what’s on my heart right now. I don’t even know what I’m asking… but I just need to talk to you.”

Before teaching: “God, I’ve got nothing without you. Flow through me. Let these be your words, not mine.”

That’s what it means to pray continually.

It’s not fancy.
It’s not loud.

But it’s powerful.

And James wants you to know — it’s wise.

Because the wise life is not not built on self-sufficiency. It’s built on staying connected to the source of wisdom, and grace, and power.

Alright, let me pray for you as the worship team comes to lead us in a closing song.