When I was two years old, I snuck out of the house without telling anyone.

To my mother’s shock, this big-headed boy with an afro mustered the strength and dexterity to pry the front-door open. Then he walked onto the streets alone, as if that was a perfectly normal thing for a baby to do.

Soon after, my family detected that Toddler Tobias was not at home. A mild panic ensued and they started looking for me. I’m told they found me down the road, a couple hundred feet or so from our house. They gently followed me, careful not to startle me so I didn’t do anything even more dangerous. Luckily, I didn’t. They caught up and took me home.

Once safely retrieved, they asked where I was going. Apparently, I responded that I wanted to buy Polo mints from the gas station. I’m not so sure what was so special about those mints that warranted a sneaky escape from our lovely abode. I’m also 99% sure that I didn’t have any money on me, so it would’ve been tricky to complete my first transaction.

There’s another story about how I was once found sitting inside the fridge attacking a tub of yoghurt. Allegedly, I wandered around the house until I nestled myself in the refrigerator, my diapers plushly propped on top of the vegetable compartment — as if to physically proclaim my disdain for greens. Several aunts have ~~threatened~~ promised to recount this story at my wedding someday.

I’m not even embarrassed to confess that I have shamelessly fashioned — indeed weaponised — these stories in my favour. I have used versions of them in applications and interviews to illustrate my supposedly good traits: driven, ambitious, decisive, assertive. That sort of vain nonsense. Curiously, I never used the stories to illustrate my stubbornness or scepticism of authority. It’s always fascinating to consider the cherry-picking that happens when we tell stories and anecdotes about our lives… What do we emphasise and what do we omit?

The point today is not to tell you about all the ways I was naughty as a baby. It’s to remind you about wandering, a perfectly nourishing but often-overlooked activity in our adult lives. It’s what I think Toddler Tobias was trying to do. At least that’s what I tell myself.

What does it mean to wander?

There are words whose dictionary definitions fully encapsulate their meanings. You see an unfamiliar word, look it up online and you fully get it. You feel you can instantly use this new-found word in many different contexts. Then, there are other words that are more complex in dimension: the definition, the usage and the etymology do not fully describe the weight of the word. At face value, they might evoke an idea in your mind, but that idea is a rough skeleton of the word’s real interpretation.

“Wandering” is one of these words for me. The literal definition feels incomplete. Google tells me wandering is “casual movement” in an “aimless” or “directionless” way. This seems incredibly subjective. Who defines what seems aimless or directionless? Is it the wanderer or the person observing? What if the wanderer and observer have different perceptions on what these aims and directions ought to be? It feels like everyone has to define for themselves what wandering is and isn’t.

A buzzing bee swirling around a plant that has no nectar. A fickle feather slowly drizzling through the air. Wild goats roaming through Welsh streets during lockdown. All of these could be considered wandering. Or none of them at all.

Wandering can mean a lot of different things. It is the slowing down of pace, and roaming through space so you appreciate what’s around you. It’s the rejection of prescribed destinations and active acceptance of randomness. Becoming like a liquid and meandering around the cracks in the road. Swaying your steps to the beat of whatever note you fancy in the moment. It’s temporarily relinquishing central command of your life. Flowing with the moments so you can enjoy the serendipity of life. It’s eschewing Google Maps and your internal compass.

Goal culture vs wandering

Our culture is obsessed with setting goals and “moving forward” in every area of our lives. Rest is often seen as the necessary evil required so that we may go again. It’s the unfortunate design flaw that means we must pause. And goals are the things we wake up to pursue.

We have work goals, health goals, money goals, dating goals and spiritual goals. We make New Year’s resolutions that we forget by March (if we’re being charitable here). We buy books that promise to tell us how we can achieve more… but we never read them. We often set unrealistic goals and then feel guilty we never accomplished them. Here’s the thing: I’m not against goals. How could I be? You're reading this essay because I set a goal to publish it, otherwise it would've remained a draft. Goals can be incredibly motivating and provide structure for us to improve. But I think we overprescribe them.

We spend too much time goal-setting and goal-chasing and not enough time asking where our desires come from. And we never talk about the downsides or tradeoffs of setting goals. The things that we unintentionally forget and regress because we didn’t set goals for them. Our goals give us blind spots, things that are good for us that we fail to see because we have tunnel vision.

Wandering is a beautiful way for you to reflect on the origins of your desires.

From birth to the grave, there’s so much we’re told that we must do, must have and must achieve in order to feel whole, loved and desired. On your wander, your body floats, roams and strolls through the streets in some direction, and your mind begins a marathon of questions: Why do I want that job? Why do I aspire to be a founder or CEO? What do I think these titles will give me? What does it mean to be ambitious? Who do I envy and why? What kinds of cultural or family traditions do I want to keep in my future, and which do I want to stop? What fears do I have about commitment? Why did I ever want to be on Forbes30 under 30?

Can I tell the difference between my internal voice and the muffled voice that society implanted in me? Is there even such a thing as a true, authentic internal voice, isn’t every internal voice itself a partial reflection of the desires of society? Aren’t we all infected with the same virus to different degrees? Have we romanticised the truth?

Aside from powerful introspection, wandering gives you perspective. You see the tiny distance between life and death as you witness a driver blindly turn right on red, nearly knocking over a couple too busy gazing into each other’s eyes. You notice that everyone is trying their damn best: from the tiny ant searching for food for its colony, to that person you never give the benefit of doubt to. You realise that apples and oranges are in fact, quite similar and we should find a much better metaphor to describe two things that are dissimilar. You see how tethered we are to our damn phones…our umbilical cords that we depend on for dear life.

When you wander through an ancient city like Athens or Rome, you feel both connected and unimportant. You’re standing on ground that people have lived on for two thousand years. For a while, it feels like a special moment you share with her former inhabitants. But you also feel a little insignificant. You’re one of several millions doing a thing that people have done for millennia and will do far long after your departure. It humbles you.

Wander walks can create epiphany moments that you can hardly find elsewhere. On your walks, you will see old things in a new light: the plant shop you always passed but never thought to stroll though. That cafe with the bearded barista that plays music a little too loud. The co-working space that’s a tad too cute and too inviting for anyone to do any serious work in.

See, I got the idea for this essay while on a walk. I noticed all these physical places I had overlooked for a while. And it caused me to ask the following: what else am I overlooking in my life? Where else have I under-invested? What’s on my bucket list? Where else do I need to wander?

How can one wander?

It would be silly for me to prescribe a work sabbatical for everyone. It made sense in my personal situation but would not suffice for others. It’s the nuclear, extreme version of something that can be done effectively on several scales.

For you, wandering might simply mean going on more walks through your city. If you’re a seasoned city-walker, then perhaps challenge yourself to go on tech-less walks: no phone, no podcast, no music, no headphones. Pick a general direction of travel and let your body flow. Walk the first block. At the stop sign, do what feels natural. That could mean staying on course or turning in either direction. Don’t feel like you need to justify your decisions. Turn left for the profound reason that you saw a cute dog on that street. Or don’t. Stay on course for no reason whatsoever. Repeat until you’re hungry.

If you’re unfortunate to live in Houston (or another city that incentivises trucks over pedestrians), then you should move. Ha, I’m joking (or, am I?). It might mean finding an activity that requires you to move, yet one you don’t feel the need to be competitive at. It could be whimsically roaming through a bookstore (no - not Kindle or an electronic one). Some are able to wander while they flow through yoga, jogging, journalling and guided meditations. Some maniacs (that I’m envious of) wander while they clean.

Travelling is a natural dimension of wandering. For the adventurous amongst you, it could be a solo trip to a country you’ve never been to before. Since I was a teenager, I always dreamed of showing up at an airport with a somewhat-packed hand luggage, taking a look at the upcoming destinations, spontaneously choosing one, buying a ticket on the spot and flying away. I can hear the stomachs of any planners in the audience churning with rage. What if it’s cold and I didn’t pack a jacket? What if it’s beach weather and I didn’t pack shorts? Why would I buy an inflated ticket at the kiosk? Because it’s the beginning of an incredible adventure. I would figure it out.

Regardless of which avenue you choose, the most important thing is to give yourself permission to wander. Reject the idea that everything you do must have an explicit direction. That your life is the pursuit of goals and optimisations that yield predetermined outcomes. Temporarily relinquish control and let your mind, body and soul roam and wander. Even if you return with the same goals and ambitions as before, you will have a newer perspective, renewed spirit and an energised body. You would have opened up new spaces inside you, ones of new possibility created through chance encounters.

So release the tight grip on your life and give yourself a little room to wander.

Wandering the grey

✌🏽🚶🏽‍♂️permission to wander