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Why Being Aimless Is a Good Thing

Thailand Sunset

It’s been one year since my decision to “take a year off.”

It was one of the best decisions I ever made. In the past year, I’ve eaten tacos al pastor in Mexico City, hiked up and down the streets of San Francisco, wrestled with existence and danced on art cars at Burning Man in Nevada’s desert, popped by Vegas for a weekend, reconnected with friends, and did a monster backpacking trip through Shanghai, Thailand, Malaysia, Cambodia, and Myanmar.

I’ve learned how to ride a motorbike, scuba dive, navigate the streets of a foreign country, take total responsibility for my own safety, speak a little Thai and Burmese, and the fine art of haggling. I’ve gotten sick, lost, scared, and dejected, but when you’re on the road for over 4 months, every moment passes, only to reveal a more beautiful one.

I started off with no guidebook or plan. I knew I wanted to start in Bangkok and end up in Shanghai for my return flight home. Everything in between – those 4 months – happened by magic, wish, circumstance. It was the best trip I could have asked for, even if I had no idea what was in store.


In Kampot, Cambodia, I took a small boat out to Rabbit island, where I swam in warm, waist deep cerulean water and picked at fresh crabs. I met a movie cast of characters there: a chatty New Zealand pork importer with his friendly Thai girlfriend; an American and recovering drug addict named David who’d spent the last four years in Kuwait, building boxes for the military; a spritely 70-something British woman, still backpacking solo around the world and flaunting a bikini. I swung in a hammock and drank juice out of a coconut. The Cambodian coastline and mountains were delicate watercolors in the distance; the palm fronds arched over the island lip and into the merged blue of sky and water.

Is this what I had feared? Is this where aimlessness takes me? A bright, intense happiness filled me, as it had and would throughout my trip.

That thought was coupled with a kind of quiet pride: I am here, because I decided to be here. And how lucky I am to be here.


Why do so many grads take jobs they don’t care for?

I don’t think the answer necessarily lies in social pressures.

Rather, we feel like we have to have a plan. A goal. And if you don’t have a plan or goal of your own, someone else’s will do. Aimlessness is something to be feared, pitied, ridiculed. It is anathema to a culture that values career accomplishment. But even more important, students don’t believe they can – or are too afraid – to come up with their own goals. What if those goals are “wrong”? What if they lead to failure?

I realized that my underlying fear was not unemployment. (That’s why I applied to jobs before making the leap to self-employment. I wanted to make sure I was actually employable.) It was not social pressure, although I felt that too. The true fear, buried below all my rationalizing, was much more insidious.

Without a structure – without somebody to tell me what to work towards – would accomplish anything at all? Did I even have goals of my own? Would I just procrastinate all day long and achieve nothing? Without a system to prod and reward me, would I collapse into a goo of TV-watching underachievement?

That is… a failure?

This is what I truly feared.

I’ve heard people deride self-help books and gurus as full of too much fluffy positive thinking advice. I get annoyed about that too. But truthfully, the deeper I get into following an unconventional path, the more I realize that our biggest obstacles are mental. Most things in life are not particularly difficult – they merely take time and persistence.

And that’s where most of us break down. Do I really want this? Is this really worth it? The decisions become overwhelming; the logistics convoluted; our bodies fatigued. And so we do something else that doesn’t awaken that doubt, at least for awhile.

It’s easy to get afraid of the questions, and the (very real) pain they cause. We’d like to assign some stability to the world as we understand it. To change the underpinnings of our beliefs is like someone snatching a security blanket from a child. You worry that doubting one thing will lead to another, and soon you’ll be so lost you can’t climb your way out anymore.

But it takes a different mind, and a stronger and wiser mind, to hold concurrent realities as all equally valid.

I found a funny thing though. It was only when I got lost – really, really lost – that I found I had a sense of internal direction after all. Sometimes, that lostness was so profound that I’d literally lost all trappings of identity. Sometimes, that lostness was the chaotic overwhelm that led to homesickness, fatigue, and a trip to the doctor for antibacterial meds.

Somehow, if you push up against lostness enough, it quiets down the other voices and points you towards what’s actually important. I learned to listen to what I wanted, and realize that I called the shots.

I love Steve Jobs’ Stanford commencement address. I listen to it whenever I need a reminder to keep going forward, even when I’m lost and don’t have a plan:

Again, you can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.

So don’t be afraid of questioning, of being aimless. You are strong enough to handle it. You’ll be ok.


11 Responses to “Why Being Aimless Is a Good Thing”

  1. Fantastic, Lingbo. I loved reading this.

    Posted by JC | April 10, 2012, 12:52 pm
  2. go Lingbo! :) This is exactly what you should be doing right now, but don’t let me or anyone else tell you what you should be doing right now. :)

    Posted by Joanne | April 23, 2012, 4:55 am
  3. wow, uhh…hmm…great article !! seriously insightful and full of life!
    Like serious good insight ….

    Posted by chepito | April 23, 2012, 8:19 am
  4. I just retired, and your philosophy is an inspiration for the rest of my life.

    Posted by Stan Rarick | May 7, 2012, 6:34 pm
  5. Love this! Randomly followed some bread crumbs from pinterest and found ur awesome blog. I can so relate (at least in part) to so much of this article. I was super frustrated with life after graduation. So I recently made the decision to move to Singapore, just me, for a nonprofit job for 3years. And I cant wait, am leaving in 2 months:) There is without doubt a sense of fear, mostly of the unknown. But knowing that others, like yourself have taken this unconventional leap and lived to tell about it gives me so much comfort. Excited to read more of your articles.

    Posted by Cecilia | May 23, 2013, 11:49 pm
  6. I’ve just come across your blog- researching for an upcoming trip to SE Asia and to go where ever else the wind takes me for an indefinite amount of time. I’ve gone through the stages of excitement, fear, panic, and I’ve only sat in front of my laptop.
    This post has truly touched me, and reinvigorated me into taking this time off to be aimless.
    Thank you!

    Posted by janina | March 17, 2015, 8:42 pm


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Lana Lingbo Li

I'm a world traveler / enthusiastic eater who's now blogging and producing videos over at HelloLana.com. Visit me there!

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