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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.


via GIPHY

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.

All too often, I don’t even realize when this resignation has set in until a passive suicidal thought comes flying my way—a sign from my emotional side that some area of my life is in crisis and needs addressing.

Where have you given up? What have you deemed hopeless and impossible? And what steps do you need to take to get help in those areas?

When we feel lost, it’s often because we’ve given ourselves a false choice. We feel trapped in the “there’s no way out” and we need someone to remind us we do have a choice.

Everyday is filled with choices to stay stuck or move forward. To explore new possibilities or hibernate. Identify what areas feel stuck and brainstorm some ways to get out of that funk.

6. What support do I need to be a better version of myself?

Who’s going to support you in your transformation?

When I made the terrifying decision to join Crossfit, I had never consistently lifted weights in my entire life. I weighed 162lbs and everyone had called me scrawny my entire adult life.

It was a huge risk, but what I missed in the gym I attended before was people to help me learn a better way and to cheer me on at my best and worst. Now I’ve put on 15lbs and am stronger and faster than ever before and I never would have done that without the support of kind, caring people.

When we feel lost, we often need someone to show us the way forward. Someone who’s been through some stuff, someone who can help us guide the way.

Joining a new community can be terrifying, it is a huge risk. But you’ll never have those people if you never try.

7. Where has my voice gone silent?

I used to be fearless in the face of opposition. I used to see brick walls and explode through them like a skinny, extremely Caucasian Kool-Aid man. Over the past few years, I’ve seen resignation make its home in areas I used to fight ferociously.

My default mode of operation for so long was to disappear, to let others choose and tell me who they wanted me to be. I rarely spoke my needs and hurts. Somewhere along the path of struggle and disappointment, I went completely passive and silent.

I’ve spent this past year fighting to reclaim that in so many areas of my life. Where have you stopped sharing your true self with the world? Where do you hide and quiet the person you were created to be?

When we’re feeling lost, often times we’ve actually lost ourselves in a world that could care less. Sometimes we have to step outside and remind ourselves who we are and who God created us to be. Speak up, my friend. Your voice deserves to be heard.

8. What do I need to quit or walk away from?

What bad habits have you given up trying to change? What activities do you do out of obligation instead of passion? Where are you over-worked and over-stressed?

Extreme busyness—constantly trying to succeed at things that don’t matter—is the fastest way to lose yourself.

Quit something, clear space in your schedule, turn down some should’s and pursue more of what makes you come alive.

When we’re feeling lost, often we need to create space for God to do new things in our life. We need to stop clinging to the past and sit in the discomfort of not knowing what is next.

9. Who am I?

Until you decide this, no question really matters.

I start each day by saying, “I am powerful force for good in this world.”

Okay, so its a little cheesey but it reminds me at my core this is what I’m bringing into the world today. Love me or abandon me, I won’t stop serving others and I won’t stop trying to make the world a better place. I won’t stop trying to tell people about how great a life lived with Jesus can be.

When we’re feeling lost, it’s often because we don’t know who do you want to be. We roam and cling to identities that ultimately leave us feeling unfilled and empty instead of deciding once and for all, to be who we want to be.

Most people aren’t brave enough to sit with these questions and for a long time, I was one of them.

But today is different.

Today, I am smiling through the wilderness knowing that all of this is part of the journey. Today I am not obsessing about what could or has gone wrong, and instead focusing on what could go right.

I’m going my own 30-day challenge and intentionally moving towards the one who ultimately knows what is next and will never stop helping me find a life that is fully and recklessly alive.

If you’re feeling lost like me, I have a Minnesotan bear hug with your name all over it.

You’ll find your way my friend, life won’t always feel like this. Good days are coming. Good people are coming. You’ve got this.

In this together,





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