Will I Be Happier Along the Road Less Travelled?

As a species, we seem to be obsessed with happiness.

A friend texted me over the weekend:

“How are you feeling right now, on the scale from 1 to 10?
10 being extremely happy and satisfied, 9 = very happy, 8 = happy, 7 = content, etc.”

After a long pause, I responded.

“Right now, I’m wrestling with this piece and trying to make it great — it’s fulfilling…but I wouldn’t necessarily say I’m “happy”… But in general, with life, I’d say pretty damn happy. Probably an 8 or 9.”

What if I was asked the day prior? I might have been a 4.

Tomorrow? Maybe a 7.

This morning? I felt like a 10.

In this very moment? I feel more like a 6.

Because in this moment, I feel a great discontent.

My discontent is in the things I have not yet achieved and the person I have yet to become.

I hold books, and I’m envious that I haven’t written one yet. I see friends giving talks to auditoriums full of people, and wonder why I’m not constantly doing the same. I listen to podcasts that feature entrepreneurs who have made millions, and I’m still trying to figure out how to generate more income than I was making in my previous corporate job.

But this discontent surprises me. Because several years ago, if I had looked at myself now, I would have seriously envied me.

Back then, I felt stuck. I was doing work that I couldn’t seem to connect back to my own purpose, my own mission. In fact, I knew little about my purpose and my missions. I knew little about myself. About my gifts. About what made me tick. Who I was.

Contrast that to the present day. I can’t say I’m a perfect picture of purpose, but damnit, I’m a lot closer.

The majority of my time is spent working with a company where purpose and mission are at the core of its existence. I have a much clearer picture on my gifts and what I have to give to the world. I’ve dived deeper into myself than I ever knew was possible.

Years ago, I felt a desire to create something—anything—but didn’t know what. I didn’t know if I had the chops to be a creator, in whatever medium I chose. I chose writing and wondered if I’d be any good at it. If I’d be able to articulate my journey to live a more deliberate life into words useful to anyone other than myself. Since then, my writing has been consumed and shared by the writers, entrepreneurs, creators I most look up to.

I used to dream of living a location independent lifestyle. And here I am, living wherever I wish and traveling essentially whenever I wish.

So why the unreasonable, the silly, the disgusting discontent? I jumped off the well-worn path to bushwhack a new path for myself. Shouldn’t I be perpetually happier? And what’s with this elusive little rascal called happiness? Why do we keep trying to grasp at it?

What is Happiness?

In a recent interview on Tim Ferriss’s podcast, James Altucher was talking about a friend of a friend who was worth $2 billion. Apparently, during lunch with another mutual friend, Altucher’s friend kept moping about how Google’s Larry Page was worth $18 billion: “Why aren’t I worth that much?” the billionaire complained over lunch.

The discussion was on why more money (or more of anything) doesn’t necessarily make you happier. It just makes you want more than you have now.

When asked about money and happiness Altucher said something profound on the subject of being happy:

“Happy is bad word. Because happy is related to the word happenstance, which is an outcome outside of yourself. So I prefer to be calm and peaceful rather than happy.”

This blew my mind. Technically, it makes sense that happy would be related to happenstance, but while I do write, I’m not much of a wordsmith. So I looked up the origin of the word “happy.”

“lucky, favored by fortune, prosperous;” of events, “turning out well,” from hap (n.) “chance, fortune”

Huh. So happiness originally meant something that graces us. Something we have little control over.

The odd origins of the word Happy reminded me of its buddy, Passion.

The Fallacy of Finding Your Passion.

In our Do Work You Love Workshop, we come out the gate guns blazing, instantly debunking the idea of finding passion by saying:

“Passion isn’t something to be found. It’s something to be cultivated, grown, fostered. You grow your passions, you don’t find them.”

One of the ways we support this is by showing what happens when you do a quick Google Book search on the phrase “Find Your Passion.”:

Find my Passion

When did we start getting so obsessed about finding our passion? Looks like around 1982.

We want to believe that passion comes upon us like a lightning bolt. That we discover our passion some afternoon as we’re cleaning out our closet. We want to believe it happens like this:

“Hey, Lucy, guess what! I found it! I found my passion! So strange, never would have guessed my passion would be this. Tiny, blue, origami frogs. Yep, my passion is for tiny, blue, origami frogs, and it was sitting under this chair, collecting dust, this whole time. Yuck. It’s kinda gross. But hey, it’s my passion!”

Yet if we look at the Google Books graph, this is a fairly new belief.

So if happiness is nothing but luck, why are we so consumed with trying to grasp and contain it? And if passion is something that is grown by taking action and making little bets on the things that excite us, why do we keep trying to find it under crevices?

I’m not so sure. But it’s easy to view both happiness and passion as a destination. As some place we get to some day. And it’s easy to imagine that people who have taken the risks, leaped off the well-trodden path, and “doing what they love” are swimming in happy every hour of the day.

Ways to Increase Your Chance of Happiness.

We meet many people at The Escape School in London, and every once in a while, I can see it in someone’s eye: they think I have it. They think Rob has it. They think we all have it. They think the entrepreneurs and the adventurers and the authors who speak at our events have it. They think we’ve captured this so-called thing, happiness.

I wouldn’t say any of us are more happy than those who are still trying to find their footing and decide which path(s) to take. However, I will say that some of us have grown to understand that there are a certain practices that can help increase happiness. None of them are easy and all of them take practice. Here are four:

1. Practice Gratitude.

Actively practicing gratitude can give you an instant shot of happiness.

“When you are grateful, fear disappears and abundance appears.” –Tony Robbins

Take a moment, look around and take stock in all that you have to be grateful for. Be proud of how far you’ve come. Be happy for the people who have helped you get here. Appreciate simple things like your health, the loving people around you, the things you enjoy doing, and the life experiences you’ve had so far.

2. Celebrate the Discontent.

Celebrate your discontent, because this is the good stuff. This is the stuff that led to most of the great creations in the world.

Discontent led to the creation of Escape the City. It’s what led me to saying “Yes” to my adventure. Discontent can be your catalyst, your inflection point, your calling.

Take it, harness it, and use it as fuel to propel you to where you want (and need) to go.

3. Pursue a Mission.

Similarly, if something ruins you so much that you reach a breaking point — you may have just found a mission worth purusing. Again, Escape the City is a classic example of discontent-turned-mission.

Missions can be big, but they can also be small. Embark on mini-missions to feel what being on a mission is like. It could just be a mission to figure out how to create a blog. Or publish a book. Or run a half-marathon. Happiness may be stumbled upon while in hot pursuit of something meaningful to you.

4. Find a Tribe.

A tribe of likeminded people can create a sense of belonging. A tribe can carry on the mission with you, alongside you. A tribe can make you feel a bit less crazy in your pursuits.

Escape the City is a Tribe. In fact, tribes are what the future of The Escape School is being built upon.

In 2015, we’re launching two new tribes: The Escape Tribe (for those who want to make a big life and career change) and The Startup Tribe (for those who are ready to start testing out their business ideas). Find our more details on both our Tribes here.

A group of likeminded people going on a similar journey can increase the swagger in everyone’s step.

“I’ve been contemplating what I need to be at a 10.”

The problem with happiness is that it’s elusive. The moment we think we’re at 10, for some reason, it feels like we’re back at 7 again. As we grow and expand, our universe seems to grow in parallel.

So maybe, if we’re doing it right, 10 is always elusive. It’s within sight, but never quite within our grasp. And maybe the point of that, is to always be growing. To always be stretching.

Not for the fame and not for the fortune. Not for anyone else. We stretch for the joy of stretching. We stretch to remind ourselves that we’re alive.

Which reminds me of a Joseph Campbell quote:

“People say that what we’re all seeking is a meaning for life. I don’t think that’s what we’re really seeking. I think that what we’re seeking is an experience of being alive, so that our life experiences on the purely physical plane will have resonances within our own innermost being and reality, so that we actually feel the rapture of being alive.”

If we wait for fortune to grant us happiness, we may be waiting a long, long time. But if we decide to try and be happy now, wherever we are, in this moment — then perhaps we can craft our own fortune.

I cannot promise that you’ll be happier along the road less travelled by. In fact, I can assure you that there will probably be moments when you can’t remember being more miserable. But what I can promise is that you’ll feel more alive — with the joys and the pains that being fully alive invites.

Don’t go along the road less travelled for happiness. But if your aim is to touch life, to grapple with it, to invite it to conquer you or be conquered by you. Then by all means, go for it.

Taking the road less travelled by may not make you happier. But it may make all the difference.


Doing something different with your life and career is hard… but you don’t have to do it alone. If you need help with your Escape and if you are ready to re-take control over your life, join our Tribe.

“No one can tell you what to do with your life and there is no “one-size-fits-all” escape that will lead you to happiness. What does work, however, is exposure to new ideas, likeminded people and a safe environment for you to figure out what it is you really want.”

– Rob Symington, Escape the City co-founder.

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