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9 Questions to Ask When You Feel Lost

Can I let you in on a secret?

Never in my life have I felt more lost. Never have I been this unsure about what is next. Never have I felt this empty and burned out.

This isn’t what I ever imagined my life looking like at 30…

and despite many blessings I often feel like I am stuck in the same repeating story-line, like a beloved sitcom six seasons past its prime. Have you been in this place?

Have you ever had to sit in an empty living room and ask yourself some really hard questions about where you’ve been, where you are and where you want to be?

I think one of the most courageous things you can ever do is admit you’re unhappy, that you wish your life was different in some way shape or form.

I mean, what the heck God? I thought we had a deal. I don’t commit any egregious crimes against humanity and you give me everything I ever wanted.


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I keep hearing this story again and again from so many people in my atmosphere – this isn’t where they thought they’d be.

We set out on the great voyage of our lives, sailing fearlessly towards India only to end up a corn field celebrating Thanksgiving with seventeen pipe-smoking strangers and two cases of Natty Ice.

How did I get here?

The truth is, this is part of everyone’s story. We all hit bumps in the road—a diagnosis we didn’t see coming, the marriage that is holding on by a thread, the blindsided layoff of our dream job.

One of the most important characteristics of people who are recklessly alive is not that they never fall, but when life knocks them down they fight like hell to get back up.

When you end up in a at a place you never intended to be, you have two options: sit around and numb the pain and wasting your life on mindless distraction OR take a long sobering look into the possibilities ahead of you and—against all odds—move forward.

If you’re feeling stuck, lost and alone like I am, instead of feeling sorry for yourself, spend time getting real about what you want your life to look like and how you’re going to get there.

Don’t dream big dreams alone, invite God to reveal His dreams for the days ahead.

One way I’ve worked on this is by creating space to breathe in the silence and sit with some really tough questions.

If you want to get woo-woo spiritual, consider using these questions as a prayer or journal prompt, take one of these questions on a long run or bike ride or pack one in your backpack for your commute tomorrow and see what wonders are waiting inside of you.


1. What would you do if you knew you couldn’t fail?

I don’t have all (or half) the answers about this recklessly alive thing but I do know those who are fully alive dream God-sized dreams and pursue them relentlessly.

They know deep in their bones they are made on purpose for a purpose and they freaking go for it. They look inside their heart and at the world around them and make a decision to do something crazy awesome. They open their Bible and learn about the kinds of dreams God believes in and wants for everyone’s life and put them into action.

What hope is tucked beneath your mattress? What on your bucket list remains dusty and neglected? Who does your heart break for?

Take fear, self-doubt, time, and money out of the question… what would you do?

When we feel lost, it’s often a sign we’re not chasing the things we want the most. So… start doing… that. Good talk.

2. What relationships are missing from your life?

This question makes me squirm more than any other. It makes me want to put my headphones on and lose myself in a daydream of sadness for a few hours.

It’s easy for me to talk about tangible goals—I’m a constantly recovering accomplishmentaholic. But to admit out loud that there are gaps in the community I dream of having…. ughllllll… That’s dangerous.

I’ve spent a lot of time fighting the fact that:

  1. I need people (gross) and

  2. I need to go find them, invest in them, and allow them to see and love me.

If you’re feeling all alone in this world, I’ll let you in on a secret: sometimes hitting rock bottom is the greatest blessing of all because you get to remake the life you want from scratch.

Your past relationships do not determine your future. You do. Take time to identity what relationships you think you need, then stop hiding behind the curtains and go meet some new people.

When we feel lost, it’s often because we’re not grounded in a kind, encouraging community. Don’t ever give up on finding your people and allowing them to love you for who you are.

3. Am I willing to risk failure and embarrassment?

Chasing the fully alive isn’t possible if you never put all your chips on the table sometimes. If you never go all-in on your own life, who will?

I tend to be overly cautious and calculated. I tend to get lost in indecision. I tend to hyper obsess about every possible outcome before even lacing up my shoes.

I have to CONSTANTLY remind myself most of the happiest moments all started with an enormous risk.

A risk to ask someone on a date. A risk to apply for a trip. A risk to apply for a job I never thought I’d get. A risk to start sharing the hardest parts of my story.

I know God calls us to take big risks with our lives where there are no guarantees he will come through. And yet, how will you how incredible God is if you never take a chance and fully rely on him?

When we’re feeling lost, a lot of times we’ve stopped chances. The more risks you take the more alive you will feel, it’s that simple.


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A post shared by Sam Eaton (@recklessly_alive) on Apr 23, 2019 at 6:48am PDT

4. What is the story am I telling myself?

This is a phrase I picked up from queen of vulnerability and shame herself, Brené Brown.

She found this powerful question, “What is the story I am telling myself?”

Example: Alvin stopped showing up in my life. The story I am telling myself is that I was too much, that when I was open and honest he decided I wasn’t worth the trouble. Allllllllvviiiiiiiiiiiiin!

Sometimes we don’t get the answer to what really happened, but so often we distort reality without any of the real facts. This question tends to ground me and allow myself to wonder instead of draw condemning and often self-destructive conclusions.

“I don’t have a job. The story I’m telling myself is I am a lazy loser. But is this true? I have filled out 27 applications – that’s actually a lot. Maybe I am not lazy. I wonder if there is someone who can help polish my resume and cover letter?”

When we feel lost, we’re believing the lies the enemy feeds that we are worthless and disposable. But his accusing words are bullshit, my friends. Hearing who God said I was started with listening to sermons, reading my Bible and being in community with uplifting people. It also has involved counseling.

5. What in my life feels stuck and lifeless?

My depression only wins when I give in to the passive, hopeless voice instead of clinging to the voice of truth and hope.