Photo: Joshua Earle (via Unspash)

There are 100 days left in 2014.
What will you do with them?

To make a long story short — a long story that involves Chris Guillebeau’s new book The Happiness of Pursuit: Finding the Quest That Will Bring Purpose to Your Life, an unconvincing tarot card reading at a yoga & surf retreat in southwestern Portugal, and experiencing the sensation of my heart being slowly broken apart over the past 9 months — I’m going to embark on a 100 day quest.

Everyday for the next 100 days, I am going to ask for something I want.

I’m not talking about layup shots. I’m talking about asking for something I seriously really want. Asking for something this is generally deemed unreasonable. Asking for something that is scary for me to ask for. Asking for something from someone who intimidates me. Asking for something that standard wisdom says I shouldn’t get. Asking for something knowing that what I’ll probably get instead is rejection.

And I’ll do this everyday, for the next 100 days.

Why I’m Doing This: The Short and Logical Story

Over the past few months at The Escape School in London, we’ve run two campaigns involving 100 day journeys. They’ve inspired me to rethink what one can accomplish in a short time period when we do a little something each day and hold ourselves accountable with a likeminded community.

In the first campaign, Founding Membership, we looked for 100 people who were interested in making a big life/career change over 100 days.

In the second campaign, called The Startup Tribe and which launched in the final days before I left for Portugal, we looked for 100 people who were tired about talking about their business ideas and were serious about acting upon them. On day 100, they are expected to launch, pitch or put something out into the world.

It’s about action. It’s about learning. It’s about personal growth. It’s about realizing that your own bullshit is what’s in between you and what you want to accomplish, and getting sick of your own bullshit is often the first step in actually doing something about it.

Via Skeletor is Love.

Why I’m Doing This: The Long and Illogical Story

As I wandered around the Port of Lisbon yesterday, I found myself contemplating my own bullshit a bit. I noticed at the forefront were thoughts about the rough and recent falling out I had with a girl I fell for in Serbia two years ago. (If you’re a long-standing reader of my blog, you might remember her — I uncharacteristically wrote a whole post dedicated to our first night out in Belgrade.) Without getting too deep into the weeds, involving several trips back to Serbia — let’s just say things didn’t really work out.

As I walked alone, I thought about what I might have done wrong, what I could have done better. The ways in which I wasn’t good enough. Thoughts about whether I’d ever feel the way about someone else as I felt about her. And if so, thoughts about whether I’d even be able to stay in one place long enough to enjoy a real relationship with that someone.

This, of course, is what I’m talking about when I speak of my own bullshit.

At this point, I had been sitting idle for ten minutes at the outdoor seating area of a touristy restaurant in Belém, an area in west Lisbon, waiting for a waiter to acknowledge me.

Occasionally, if we’re lucky, we’re able to catch ourselves wallowing in our own destructive thoughts, as if we’ve become an impartial observer of our own life and situation. Like being the sole witness to a drowning man, you know you have to do something. So you toss him a line or a lifesaver, or you jump in and try to save the guy.

Eventually your Great Discontent bubbles up and erupts. Imagining the stench of these thoughts emitting from the dockyards of lower Lisbon, I jumped up, pushed back my chair, left the table and started walking down the street again.

I didn’t even want your shitty food anyway!

To be fair, I did kind of want some bacalhau. But not from that place I didn’t. I was hungry and stopped there because the restaurant happened to be right in front of me. It was there and it looked good enough.

It wasn’t the restaurant’s fault. It wasn’t her fault. I felt like I had let myself get lost, that I had let myself down. I was driven less by the little stirrings inside me — the stirrings that led me to say “yes” to my adventures. I felt more driven by the foolish desire to ensure a fairytale-like happy ending to a romance that had a fairytale-like beginning. In attempting to rearrange my life for someone who clearly wasn’t ready or able to do the same, I had let myself get lost. I forgot which port I was gunning for. Like the risk Odysseus faces in Homer’s Odyssey, I felt caught up a Siren’s Song, a song that when heeded took me far off course and inevitably toward a slow and painful death.

This was a situation where following my heart failed me, or at least at the present moment it appeared that way. I had placed myself inside a tiny cage. It felt a little like drowning.

My big goals and dreams and proceeding confidently in the direction of those dreams had taken the backseat for a bit. This frustrated me. Was I was losing my edge? I thought I might be. And I desperately needed to do something about it.

I found an artisan burger joint down the street — a burger being something I was craving ever since having a detox week of no meat, no wheat, no refined sugar. I walked into the joint very seriously, and with conviction ordered exactly what I wanted to eat from someone who wanted nothing more than to serve me a tasty burger. It was a perfect example of desire and expression of desire. It was a healthy interaction of giving and receiving. And it felt good to be back in control of my gastronomic destiny.

I need to get clearer about the things I want and not be afraid to confidently ask for them, I thought.

Then I thought about quests and Chris Guillebeau’s new book, The Happiness of Pursuit.

Questing for a Quest

In it, Guillebeau showcases a bunch of quests and journeys — physical, mental, and otherwise. The Big Idea in the book is that in pursuing these self-directed and self-determined quests, our lives become more purposeful.

What makes a quest? At the basic level, it’s a clearly defined destination with a clearly defined deadline. Throughout, Guillebeau pulls material and wisdom from his own quest to visit all 193 countries in the world before his 35th birthday.

In the quest examples, sometimes the deadline was by a specific milestone date (e.g. “by my 35th birthday”) and sometimes it’s more of a steady countdown or count-up (e.g. “for 100 days”). Most of the time, people embarked on a quest to address some nagging desire that wouldn’t leave them (e.g. “I want to walk across Turkey!”). Or to marry a checklist to a passion (e.g. “I want to set the record for the most sighted birds!”). Or to promote a cause (“I’m going to protest illegal logging by climbing a tree in Tasmania and live there for one year!”). But often, the underlying current was mostly about self-discovery and self-improvement.

I got to thinking: If I were to embark on some sort of self-improvement quest, maybe something around clearly articulating desires and asking for things that I wanted, wouldn’t it be cool if it was during the final days of 2014?

I wondered how many days were left in 2014. I pulled up the calendar on my phone and counted the days: 101.

Shit! That means I have to start a quest tomorrow! I panicked.

Act now. Think later.

I felt butterflies in making my decision to do it. Although it could have just been the the influx of meat, grease, bad carbs and gluten rushing through my recently purified body.

Nevermind. This seemingly half-baked thing is proceeding, full go, starting today.

That Ain’t New, Baby

To be clear, what I’m doing isn’t new. I didn’t invent the 100 day challenge. You’ve probably have seen someone on Facebook or Instagram documenting some sort of 100 day challenge (or other timeframe) over the past few years. This year, I followed Amber Rae as she did her 100 Day Book Project. Which was inspired by Elle Luna’s 100 Day Project. Which was inspired by a class Michael Beirut teaches at Yale. Ain’t no shame in a bunch of artists stealing as artists love to do.

Even the details of this particular challenge isn’t new. I’m stealing this directly from Jia Jiang’s 100 Days of Rejection Therapy, which I read about in The Happiness of Pursuit.

But it’s still scary and it probably won’t be easy. Even on Day 97 of his journey, Jiang revealed how facing rejection wasn’t any easier than it was on Day 1 (that day’s task was to stand on the streets of Austin asking people to listen to him monologue his story).

It’s scary because I’m committing to this publicly. But I’m committing to it publicly because it’s something I deep down want to address in myself.

Why This Particular “Ask For Something You Want But Probably Get Rejected Instead” Challenge?

I’m doing this particular challenge because the fear of rejection is something I continue to struggle with. I have trouble asking for help — my default mode is to keep chugging along with my head down and not ask for it. And while I do have a history of setting big goals and going for them — I could stand to do better and set my sights higher. I can improve on clearly articulating things that I want in life and confidently going after them, early and often.

This particular quest into the land of rejection is of a similar flavor to something I did almost two years ago under a warm October sun in Zadar, Croatia when I asked strangers on the street if I could film them.

As I’m learning, we never really “get over” our fears or conquer our vices. The best we can do, I believe, is learn to dance with them. We can learn to live with them, grin at them, and proceed confidently knowing that they’re still hooked onto our hip. This takes deliberate practice and dedication.

Who Wants To Join Me?

Another thing I’ve learned in building The Escape School is that the secret sauce to everything we do isn’t the content of the courses or the profile of our speakers. It’s in the community. When you bring together a group of likeminded souls on a similar journey, it increases the swagger in everyone’s step. Everyone’s more likely to follow through on their self-imposed goals and commitments. For this reason, I’d like to invite you to join me over these 100 days.

  • If you could change anything about yourself, what would it be?
  • If you could make good on something you’ve neglected over the past year, what would you do?
  • If you could dramatically increase the progress of a project, why not do it now?

If you’re interested in doing your own 100 day challenge alongside me, I hope you’ll join me.

This is your chance to make good on the five-star procrastination you’ve been absolutely nailing over the past 265 days.

This is your chance to take these 100 days and do something with them.

Day 1 is today, September 23, 2014.
Day 100 is December 31, 2014.

No more excuses. No more waiting. We start today.

To join me in your own special and unique 100 day challenge,
let me know here.

(If you’re reading this after Day 1 and think this could be a good experience for you, please don’t let that be an excuse. Doing something different for 97 days or 82 days is better than doing it for 0 days.)

For more information on my challenge, please join me here >>>
The GiveLiveExplore 100 Day Challenge.

Oh! I almost forgot. About that tarot card reading. It was mostly hogwash. But one thing the woman said stuck with me.

“Your power is found in your loneliness.”

Indeed, it is. I learned this in my wandering months, but had forgotten it. Thanks for sending me on the solitary walk in Lisbon, tarot card woman.