My tenth challenge was a complete and utter failure. I was supposed to talk to 3 cute girls each day for 5 days, but I only ended up talking to 3 because I fell violently ill. I spent the entire week in bed, watching TV and groaning. But I wasn’t going to let that defeat me.

Hell no!

My goal was to make up for my failure by completing two challenges the following week, but I quickly realized that it wouldn’t be possible. The sickness had sapped my strength, and it took me another full week before I was back to normal. Luckily, I was able to use this time to complete another challenge.

Figure out what the hell I should do with my life.

Confused? Don’t worry, I was too.

I’ve always been a dreamer. It’s my greatest asset and my biggest flaw. Why? Because I’ve become so obsessed with attaining my grandiose goals that I fail to enjoy the process. I also hold on to things for WAY too long.

Let me give you an example.

I always dreamed of being a successful author. I spent the past seven years honing my craft. I wrote millions of words, taken dozens of courses, read hundreds of books, and listened to countless podcasts. I learned how to edit, market, and network. Millions of people read my stories, yet I never made a profit. I invested my entire livelihood—and more money than I care to admit—into this passion, and I have nothing to show for it.

Most people would have given up long ago, but I refused to even consider such a possibility. I kept writing, even when the love of the craft was gone. I kept promoting my books, even when I failed to make a profit. I kept trying new strategies to grow my readership, even though the results were laughable, and the extra workload threatened to crush me. Even now, I continue trying to make it as an author.


Because I’m obsessed. I can’t imagine my life without writing. The prospect of giving up on the only thing I’ve ever truly loved terrifies me. Maybe all this hard work will one day pay off, and I’ll make it as an author, but the odds are high I’ll forever remain trapped in obscurity.

Are you starting to understand why I’ve felt so trapped? But my love of writing is only one of the many ways in which I imprison myself.

Personal development is another primary passion of mine. I’ve been obsessed with becoming the best version of myself ever since I had a near-death experience in my early twenties, but it wasn’t until a few years ago that I truly became obsessed.

This obsession, coupled with my desire to help others, culminated with my launching of The Journey of a Thousand Mistakes, a brand meant to show people that growth is a messy, lifelong venture that requires hard work and dedication. The plan was to challenge myself each week for an entire year and release a weekly YouTube video, a podcast episode, and a blog post detailing the lessons learned.

I thought pushing myself would transform me into the version of myself I’d always dreamed of becoming, but I quickly realized I’d taken on too much. The workload began to weigh heavily upon my shoulders, and I suspect this is why I fell ill. Not to mention the fact that all this hard work had gone nearly unnoticed.

How am I supposed to help people when no one is consuming my content?

I started feeling like a complete and utter failure. Why was it that everything I tried failed? I failed as an author. I failed as an influencer. I failed at so many things, and though I kept a positive attitude throughout, I couldn’t help feeling as though all that hard work had been for nothing.

To make things worse, my roommate—AKA my best friend—told me he was moving in with his girlfriend. I was thrilled for him, but it couldn’t have come at a worse time. I was regretful of my past, doubtful of my future, and now I had to find new living arrangements.

The way I saw it, I had four choices. Option 1: I could stay put and find a new roommate. Option 2: I could move out and hope to find a nice apartment with a cool roommate. Option 3: I could get my own apartment and live alone for the first time in my life. Option 4: I could sell most of my things, put the rest in storage, travel for a few months—or years—and figure out what to do with my life.

Sounds easy enough, right?


I considered going on a 10-day Vipassana Meditation retreat to figure out my next move, but the world was in a frenzy because of the coronavirus, and the meditation centre was shut down. My plan to travel and figure out my next move was also on hold because more and more countries were being quarantined, and air travel was growing increasingly restricted.


As you can see, things weren’t exactly going great. Not only were my options growing more and more limited, but I still had no clue what to do or how to go about figuring out my next move. Deep down, I knew everything would work itself out, but in the meantime, I felt trapped in a limbo of uncertainty. Hopefully, the answer would present itself soon.