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It’s Okay If You’re Feeling Lost

Wandering Aimfully Through Confidence

It’s Okay If You’re Feeling Lost

How I've dealt with feeling lost over the years and how you can learn how to find yourself.
Jason ZookJason Zook Jason ZookJason Zook

Written by

Jason Zook

Over the years I’ve dealt with feeling lost on many occasions. Whether it was taking my first step into the world of entrepreneurship (working for myself) or leaving behind a “successful” business (IWearYourShirt).

Feeling lost seems to be part of the human equation. Something we all have to deal with at different times in our lives, whether we like it or not.

I felt the most lost after an amazing weekend in Fargo, North Dakota in 2013 at Misfit Conf.

In May 2013, I attended a small conference in Fargo, North Dakota. I’d never been to Fargo before and the only thing I knew about the conference was that I was a speaker, and it was going to be a small, hand-crafted event put on by my friends AJ and Melissa Leon (of Misfit Inc).

Feeling lost at Misfit Con, Jason Zook and Srinivas Rao

Backing up for a moment, at the time (May 2013) I was running my IWearYourShirt business and things were in a huge state of flux. Actually, let’s just call it like it is: My business was failing completely and I was 100% burnt out.

My IWearYourShirt business had been my life-blood for the previous five years. It changed me as a person. It brought me amazing opportunities in life. It taught me so many lessons about running my own business. It also helped me build my first (awesome) community of friends, followers, and customers. But IWearYourShirt also took over my life, robbed me of all my time, and left me $100,000 in debt and 50 pounds overweight.

When my wife and I boarded the flight from Jacksonville, Florida to Fargo, North Dakota, I knew I was at a breaking point. Something had to give, I just didn’t know it would happen in front of a room full of strangers.


Why Was I Feeling Lost And How Did I Overcome It?

Let’s back up even further for a moment. In 2007 I left the 9-5 corporate world to start my first entrepreneurial venture. I took a huge risk to leave a super comfortable career as a web designer, to start my own design company with a friend. I had my first inkling of feeling lost at my comfortable 9-5 job. I felt out of place sitting in a beige cubicle. I felt incredible resistance to mundane meetings. I certainly didn’t see my work as meaningful, nor was I ever proud to share it with anyone other than my boss (for his approval, so he’d keep paying me).

I felt the least lost when I was in control of my day and my decisions.

As it turned out, working for a corporation or in my own first design company I realized I wasn’t really passionate about web design, websites, finding great clients, or any of that. I found that I liked working for myself and calling all my own shots. I felt the least lost when I was in control of my day and my decisions.

During the year and a half that I ran my own design company with a friend, the idea for IWearYourShirt came to me. I remember that idea giving me an incredible feeling of purpose. It wasn’t even a business yet, heck there wasn’t even a logo for it, but the idea itself gave me hope. It gave me a direction to go in. It gave me something that felt bigger than myself and something truly unique.

The first time I ever got over the feeling of being lost was when I chased a big idea and allowed it to have space in my life.

An emotional meltdown actually helped me deal with feeling lost

Having a mini emotional-meltdown on stage in front of a room of strangers helped me realize I was lost and forced me to start dealing with feelings I’d been internalizing.

Getting back to the beginning of this story, being a speaker at Misfit Conf presented me with a weird opportunity. I wasn’t new to public speaking and sharing my IWearYourShirt story with a room full of strangers, but this was the first time when I felt like I would be a fraud if I pretended everything was okay. If I just stood on stage and spewed the same stories I’d done the previous few years at countless speaking events around the country.

Instead, as I took the stage in front of 100+ people I didn’t know, I decided to admit I was feeling lost.

I remember sitting on a chair and saying out loud, “Normally I’d tell you all the good things I have going on in my life, but I can lie to you or myself any longer. My IWearYourShirt business is failing and I have to be honest about it.”

I don’t remember the next 45 minutes of my talk. That’s the honest truth. All I remember is snapping back into focus, seeing a room full of people with tears in their eyes, standing and clapping, and me feeling an incredible weight lifted off my shoulders.

For the first time in five years, I’d told a group of people that things weren’t going well. Every day prior to that I’d put on a face and a show.

I’d pretended and forced myself to say that life was perfect. I thought if I didn’t do that my community would abandon me and no one would pay me money ever again.

I stepped off the stage to a group of 100+ strangers who welcomed me with open arms. Where I’d been thinking people would ridicule me for admitting things weren’t going well, I was instead met with love and encouragement (truthfully I think Misfit Conf was the best possible place I could have had this emotional meltdown – that group was/is something really special).

When you’re feeling lost, something has to change

I had been dealing with feeling lost for months (maybe even years) leading up to that talk in Fargo, North Dakota. But instead of trying to acknowledge being lost, I suppressed my feelings and didn’t change anything. I tried to strong-arm my way through my problems, not realizing that I was merely putting tiny band-aids on a gaping open wound. When I took the stage, poured my heart and soul out, and was accepted for my failings, it was as if a switch was flipped.

My wife and I boarded our flight back to Florida and we spent the next few hours talking about everything we’d change.

Let’s be honest with each other: Change is f*cking hard. It just is.

But without change, I realized I’d just keep digging myself further and further into a hole. I’d ignore problems and I’d hurt myself and the people around me that I cared about most.


How To Find Yourself Through Embracing Minimalism

At that same conference, another speaker took the stage and his name was Joshua Fields Millburn. With his beautifully coiffed hair, he spoke about his life and how lost he had been at certain times. His story really resonated with where I was in my life and I was eager to learn how he solved his own issues.

That’s when I learned about minimalism. Not about getting rid of everything you own and only having one chair in your entire home, but looking at everything you own (and choose to spend your time on) and deciding if those things are actually bringing you value.

Decluttering our home helped us combat feeling lost

It may sound silly to say that getting rid of a few household items made me feel empowered, but it’s absolutely true. The stuff we surround ourselves with takes more of a mental toll than we can see. When YOU are the one to remove something from your life that is no longer serving you, it feels great.

My wife and I started with our closet, getting rid of garbage bag after garbage of clothing we no longer wore. Clothing from our time in college. Clothing from when we were another size in our lives (damn you teenage slender years!). Clothing that we bought on a whim because we thought retail therapy would make us feel better about the things we had going wrong in our lives. It may be hard to believe, but my wife and I spent multiple hours in our closet laughing our way through getting rid of mountains of unused items.

Jason Zook and Caroline Zook embracing minimalism

From our closet, we moved on to other rooms in our home. It didn’t happen in one weekend. Our process of decluttering took weeks/months. But then I decided it was time to apply minimalism not only just to the stuff in our home, but also the business we ran out of our home: IWearYourShirt.

On May 6, 2013, I shut the doors to my IWearYourShirt business. As weird as it may sound, posting a status on Facebook about closing down my business felt better than most things had in my life at that time.

We re-painted our office, which was decorated for IWearYourShirt and all the videos I had been filming on a daily basis at that time.

IWearYourShirt Office, 2013

Rolling white paint over years of memories was equal parts sad and exciting. With each stroke, I felt like I moving toward a new life and new direction. Every brushstroke was one move closer to taking control back in my life.

From that day, we’ve continued to embrace minimalism in our lives. We sold everything in our home and kept only what we could fit in our small VW SUV and moved clear across the country to California. We’re proud to call ourselves minimalists, and we have way more than one chair!

Okay, truthfully, we only own three chairs and two stools, but that’s all we need.


Four Ways To Overcome Feeling Lost And How To Find Yourself

In 2014 my wife and I ventured back to Fargo, North Dakota for our second Misfit Conf. We spent the entire previous year rebuilding our lives and businesses. Getting rid of the things we no longer needed, and for me, sharing more of the thoughts and feelings I was keeping pent-up.

We hadn’t fixed everything in our lives, our businesses were still in flux, we learned three valuable lessons after our second weekend in Fargo:

Lesson #1 to avoid feeling lost: Give yourself permission to do the things you want to do

We all have ideas, goals, and dreams, but most often we are the ones limiting ourselves from making those things happen. It’s not money, timing, or any other factor, it’s giving ourselves the permission to just get started.

I wasn’t able to accomplish what I’d accomplished in the previous year because of luck or good timing. I intentionally changed things in my life and “sat in the chair” as Joshua Fields Millburn says. It wasn’t easy for me and it probably won’t be easy for you. The key is to make a commitment to yourself and to not do it alone. As proud of a person as I am, the best thing I did was give myself permission to start asking for help and being open to the change that comes with that help.

My wife Caroline deserves so much credit here. Not only because she was my biggest cheerleader in me giving myself permission to shut down my IWearYourShirt business and do other things, but also because she is so emotionally tuned-in and could help me navigate the thoughts and feelings I was having.

Lesson #2: Stop being so proud

I was too proud to ask for help. I was too proud to think I could figure everything out myself. I was too proud to ask people smarter than me for advice. I was just being too damn proud.

After the second year attending Misfit Conf, I decided to let my guard down a bit in hopes of figuring some things out about myself. I’ll be the first person to admit that I used to shudder at the idea of reading a self-help book or talking to a coach of any kind.

Acknowledging that I was being too proud made me feel like I was at least taking the first step toward working on these things.

I’m not sure where my too proudness stemmed from. I can’t remember a specific story from my childhood, but I’m sure there’s something there. Nevertheless, I remember being stubborn from a young age and I needed to change that. I needed to let go of trying to be in control of everything, especially my emotions.

While I do see pride as a useful tool in certain situations, it can also be a detriment if you have too much of it.

Maybe you’ve been too proud in certain circumstances that led to a fight with a loved one or a bad business decision?

It might be time to admit this to yourself and attempt to make a change.

Lesson #3 in how to find yourself: Stop trying to answer “what do you do”

This may sound dumb, but maybe you can relate. The question “what do you do?” had thrown me for quite a loop since 2009. Explaining IWearYourShirt to a random stranger in an airport who wanted to make idle chit-chat? That was always a hot mess.

I started to really resent the question especially after I shut down my IWearYourShirt business. I didn’t have an easy answer that quickly explained my weird entrepreneurial endeavors and each time I was asked thoughts of doubt and criticism swirled around in my head. I started to wonder why this question was bothering me so much and if there was a way I could fix it?

After multiple conversations with my wife, we both decided I should just accept that I was in a time of flux and experimentation. Sure, I didn’t have an easy answer at a cocktail party that could quickly define who I was and what type of work I was doing, but that started to not matter once I allowed myself to be doing a “floaty dance through life” (as my buddy Ben Rabicoff put it).

Once I came to terms with the fact that I didn’t need a clear definition of what I did for work to give me self-worth, I started to be more accepting of myself.

Lesson #4: Writing is cathartic

I never thought I’d be a writer. Heck, even as I type these words to you, it feels incongruent to the person I pictured I’d be in life. But alas, here I am. A writer. Someone who has typed millions of words, thrown the majority of them away, self-published a book, and written for many major publications. But it didn’t start that way.

Writing became my form of personal therapy.

My journey with writing consistently started with writing little blog posts about life and things that weren’t going so well.

I was incredibly nervous to hit publish and to share the first blog post I ever wrote that was the least bit vulnerable. But guess what happened? People celebrated my honesty. They didn’t critique all the bad grammar and poor sentence structure. They simply appreciated that I was willing to go out on a limb and to share something many people might not.

My writing went from a random blog post here or there from 2012-2013 to a consistent weekly post and email in 2014 to a small group of subscribers (just 400 people). Also in 2014, I self-published my first book, Creativity For Sale.

Writing a book was one of the most cathartic things I’d ever done in my life because I got to finally share so many stories of failure and mistakes that I’d kept bottled up inside.

In 2015 I started writing for Inc Magazine and a few other notable media outlets while continuing to write for my own audience (a group that became known as the Action Army). In 2016 and 2017 I stopped writing for anyone else and only wrote for my own audience on

In just a few short years I went from writing random updates on a Tumblr blog to having over 500,000 people read my writing in 2017. Can you believe that? It’s hard for me to believe!

Maybe writing could be an outlet for you? You don’t have to start by publishing your writing. Maybe it’s just a journal you keep? Or a daily writing practice you do for one hour per day that lives in a Google Doc that only you know about? Give writing a shot, it was instrumental in helping me overcome feeling lost.


Feeling Lost Is Something We All Deal With, Don’t Try To Get Through It Alone

While I do believe some solitary activities can help, like writing, if you’re currently feeling lost you should absolutely reach out to someone. Is there a peer in whatever industry you’re in that has been down a similar path to you? Or maybe finding a therapist in your local area that is highly well reviewed? Therapy has such a negative connotation, but people like my wife swear by it (and we celebrate its effectiveness in our house!).

We all deal with feeling lost at certain points in our life. And I hate to be the bearer of bad news, but even if you overcome a big milestone of feeling lost like I did in 2013, you’ll be met with more bumps along the road.

If you want some book recommendations, I’d highly recommend The Obstacle is the Way and Body of Work. Both of those books were really helpful for me and continue to provide lessons for my life.

I’d also highly recommend giving minimalism (your own flavor of it!) a try. Decluttering your life can lift more weight off your shoulders than you’d ever imagine.

You aren’t on this journey called life alone. There are people around you who want to support and help you. Be willing to open up to them and be willing to ask for help. It was difficult for me, but it was also the best thing I’ve ever done.

It’s Okay If You’re Feeling Lost

(Big Fat Takeaway)

Feeling lost seems to be part of the human equation. Something we all have to deal with at different times in our lives, whether we like it or not.


This article written by

Jason Zook

I'm all about that Cinnamon Roll life (that just seemed like a "cool" way to say I love baking and eating cinnamon rolls). Also, I co-run this WAIM thing as well as Teachery. Currently, 75ish% completion of Tears of the Kingdom 🧝‍♀️⚔️.

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