I Dare You To Quit

This post was last updated on 2020 October 26

I’ve just moved into a share house in Camberwell, an eastern suburb of Melbourne, where I’ll be living for 4 weeks. Tonight, I’ll be sleeping in my 35th bed this year. It looks to be one of the better ones I’ve had, kitted out with colorful floral sheets and an absurdly comfy comforter that the girl who’s subletting to me left behind. My room is equipped with a flat screen TV and speaker system that I’m sure I won’t know what to do with. There are 6 rows of shelves all along one wall and a wardrobe opposite them, which means I might actually have the space (and time!) to unpack my meticulously-arranged clothes from my suitcase. For AU$150/week (a smidge over US$100/week), this room is objectively a steal – especially for Melbourne.

Less than 24 hours ago, I didn’t even know where I’d be living today. I was on the last day of a 10 day house sit up in Reservoir and had been somewhat passively plotting my next move. “Wait, so you still don’t know where you’re moving to tomorrow?”, a friend asked me, incredulously.

See, that’s where I’m at right now. I’ve become so go-with-the-flow that not knowing where I’m going to be living the next day, or how I’m going to transport my 70kg of luggage there, doesn’t even faze me.

Sydney Opera House

I woke up yesterday morning and thought: ok, it’s time to find my next home. I reached out to a couple of people who I’d been in contact with over the past month about possibly renting a room. I combed the posts on a few housemate finder Facebook groups and the sublet ads on Gumtree and carpet bombed every post that advertised an affordable room in a desirable location available ASAP. I scoured Airbnb for some last-ditch options in case I needed to book a room for a couple of nights in a pinch.

By mid-afternoon, I’d secured the room in Camberwell without having visited the house or met the housemates. I wasn’t too worried about it, much like I wasn’t too worried about finding a new home with such short notice.

Because whatever happens, I know I can handle it.

Working out at the beach in Perth

Quit Everything

Having this level of confidence in yourself is completely liberating.

You want in on this magic? Try stripping your life of everything that makes you feel secure: your home, your relationship, your steady paycheck with benefits. Then, start living as a free bird, slowly and deliberately piecing together your new life. It’s going to be scary as hell at first, and you’ll probably contemplate settling for the nearest soul-sucking corporate job or eligible bachelor(ette) just to feel like you have something in your life figured out.

But here’s the thing: you don’t have to have your life figured out. I’d even argue that it’s better not to.

If you always have things planned, secured, and sorted, you’ll never know how strong you are when you have to face life without a crutch or safety net. Think of all the missed opportunities for growth when you play it safe and mindlessly stick to the path you’re on.

Iceland Laugavegur Trek
Hiking the Laugavegur Trail in Iceland.

By contrast, when you leave your life as open as possible, you’re making yourself available for more/better opportunities and trusting in the flow to guide you to where you need to be. Your life will unfold organically as you call the shots in real time. Congratulations, you’re now an active participant in your own life!

It certainly won’t be easy, though. You’ll quit things and start new ones. You’ll make mistakes and learn from them. You’ll lose some and you’ll win some. It can be terrifying at times, but the more you practice living life in this way, the stronger you’ll get. Soon you’ll reflect on the hundreds of obstacles you’ve had to face and realize you’ve handled them all – every single one of them. Life’s a lot less scary when you’re confident enough to think: I got this, no matter what it throws at you.

Suddenly it’s pointless to plan or worry. You know how the story’s gonna end every time: with you handling it. Free of stress, fear, and obligation, you can finally be more present and enjoy the moment.

All because you dared to become a fully confident person.

Mornington Peninsula bathing boxes
Jumping on the Mornington Peninsula near Melbourne, Australia

My Story

Before my year in Australia, I was extremely self-conscious about my lack of a career path. I would look at everyone around me climbing the corporate ladder, celebrating promotions and settling into their careers wondering: am I ever going to have that? But I know what goes on behind the scenes of those #humblebrag social media updates: a whole lot of complaining, stress, and tears. I’ve actually had friendships based on mutual bitching and moaning about work.

I could totally have that career success if I were willing to choose one of my many interests, commit to a job, and stick it out even when it dead-ends or becomes unfulfilling. But as a rule, I’m not in the business of settling. When something doesn’t feel right to me, I quit it.

About 6.5 years ago, I mustered up the balls to quit my first job after months of misery. I was TERRIFIED. Beyond that, I felt really guilty about quitting: who was I to throw away a perfectly good job, one that most any college graduate would kill for? Moreover, what would I do next?

I handled it. I used this period of funemployment to dive into my passion for photography and started a wedding photography business that I would run part-time for 5 years. Would I have tapped into my entrepreneurial prowess or become a professional photographer had I remained trapped in a miserable job I knew wasn’t right for me? Possibly not.

Waterfall in Oregon
Oregon, circa 2009

I quit my second job nearly 3 years ago with a little more conviction. This time I had a plan: I was going to travel in Asia for 5 months. Giving my boss notice was a little less scary, but jumping into long-term travel in a completely foreign part of the world added a different sort of fear to the mix.

I handled it. I trekked to Everest Base Camp, survived the metaphorical (and arguably literal) sh-tstorm that devoured me in India, and solo traveled around Southeast Asia where I immersed myself in travel blogging. When I returned to NYC I got more serious about blogging: I enrolled in the MatadorU travel writing program and attended BlogHouse to further my writing skills and business acumen. Would I have gotten into travel writing and the business of blogging had I not dared to quit my job again and travel for so long? Possibly not.

Everest Base Camp

I quit my third and final corporate job about a year ago and it was almost easy. This time, I hit the reset button on my entire life, not just certain aspects of it, as I left my job, moved out of my Brooklyn apartment, and relocated to Australia indefinitely. You’d think I’d have been scared shitless, but mostly I felt an undercurrent of calm because I’d been unintentionally preparing myself for this with all my past quitting and leaping. Above all, it felt so right to me that NOT quitting my old life would have been more difficult than quitting it.

And I handled it, just like I handled every other challenge presented to me in the past 30 years. I’ve managed to travel to every state and territory in Australia this year while spending an average of just US$35/day AND keeping up with my monthly student loan payments. When I desperately needed to make money, I found a casual job in the Outback. When I was damn near homeless on more than one occasion, I found a couch to crash on, a work exchange to earn my keep, or a last minute apartment to move into. When no one would sponsor me to stay in Australia and work for their company, I started freelancing and landing enough gigs to financially support myself.

Now I get to work on a variety of projects of my own choosing, on my own time and terms, from anywhere in the world. Would I have achieved this level of freedom had I not quit my whole life and dared to start over, living 100% on my own terms? Definitely not.

It’s absolutely amazing what you can do or become when you take that leap – but you’ll never know until you face that fear and go for it. Remember: you can handle it!

El Questro Gorge
El Questro Gorge in The Kimberley

Why Quit?

Quitting everything and stripping your life down to a blank slate has other benefits, too:

You have the freedom to create a life you want, not a life that you just sort of ended up in.

You can make decisions as they come based on what feels right to you at that moment, instead of staying on a particular path that leads to a predetermined destination.

Best of all, you give yourself the gift of being able to live in the present and enjoy the journey of life, rather than constantly planning for, worrying about, and working towards the future.

You know you’re right where you’re supposed to be – because how could you possibly be anywhere else in your entirely self-designed life?