Are You Thinking of Quitting Your Job? – Part 4

By: Jonathan Kalan, Unsettled Co-founder

Well, congratulations. You finally admitted it to yourself. You actually decided that what you’re currently doing right now simply isn’t cutting it. You’ve gotten through that roughest part… the denial. The constant weighing back and forth between your vacation perks, great benefits package, and that tantalizing promotion you’re bound to get in the next year… and the freedom (and let’s face, fear) of actually doing something that matters to you at this point in your life. It ain’t easy, so do me a favor. Stop and acknowledge it for a moment. Sit with it. What does this now mean?

Over the past decade I’ve navigated my fair share of transitions in life. At 32 years old, while I’m hardly a third of the way through my working life, I have no reservations in saying it’s been one hell of a journey. I’ve switched careers, and often entire industries, every few years. I’ve worked as a foreign correspondent in conflict zones and an office manager cleaning toilets; an employee at multiple startups to eventually founding a few of my own. I’ve worked in media, tech, nonprofit, education, and travel. I’ve called at least four continents home for extended periods of time, and have sought a life rich in experiences; one driven by a broader pursuit of growth, meaning, and adventure, not necessarily a singular outcome. I never strove to be the best at anything. I simply wanted to do things differently, and keep learning along the way.

At each of those moments of transition, I’ve had to ask myself a series of profoundly challenging questions. Sometimes the answers came rather quickly. Other times, it took months, even years to arrive at the answers. Many of the questions I’m still searching for a resolution for (aren’t we all?), yet I continue to enjoy leaning into the process.

Reflecting on each of those experiences and moments of change, there are three things in retrospect I can point to that helped me navigate the uncertainty and pick a path forward each time. I’d like to share them here, for all those who are sitting in that “unsettling” space between potential and possibility, predictability and opportunity, the known and the unknown. They are key tools for navigating our lives, and a core part of Unsettled’s new Lifestyle Incubator program, which I’ll be co-facilitating this November and January.

1. I Had A Diverse Community

We all live in our own little bubbles. No matter how big, broad, diverse, international or cross-industry yours is, it’s still a bubble. Each time I’ve sought to challenge myself and think about my next steps, I’ve opened myself up to as wide a community as possible to understand the scope of where my journey could lead. I spoke openly to friends, friends of friends, and complete strangers about my experience, my big questions, and where I thought I wanted to be. I’d take any opportunity I could to discuss, broadly, “life” with strangers, and see where it led. And it most always did lead somewhere interesting, or offer some new insights. A diverse community of opinion and feedback helps burst the bubble, shift your perspective, and challenge you in ways that you – or even your closest friends – might not be able to.

2. I Sought To Understand My Processes, Not My “Work.”

It’s easy to fit yourself into what I call a “career box.” “I’m a writer.” “I’m a marketer.” “I work in the travel industry.” “I’m a good analyst.” And so on. Yet most of us hate boxes, and recognize that we are multidimensional beings with various interests, skills, and passions. Each time I reached a tipping point or crossroads, I had to step back and look at my journey to find the trends. Not the trends in the titles I had or the work that I did… but the trends in the process itself which I enjoyed. I’ll share one example.

During my early 20’s, I worked for many years as foreign correspondent and photographer based in Kenya. It was a dream job and dream lifestyle I was living. I loved what I did. I was contributing to some of the best publications in the world – The New York Times, BBC, Foreign Policy, The Atlantic.Yet, I never really felt fully satisfied with it. It felt my identity never really fit in the industry of journalism. It was pessimistic, the people around me were an exciting but also often a miserable (and single) lot.

After thinking through this for years, I came to realize that what I loved was not being a “journalist”. It was the process of being a journalist that inspired me. And that process was traveling to new places, meeting new people, discovering new things, and translating those experiences into words and images that could inspire or move others to action.

My natural process, what I love to do, in short, was being in motion, discovering, connecting the dots, and sharing.

That small but important paradigm shift, of examining the layers behind my work and understanding the process that fulfilled me, helped me think more laterally about my life and career choices. And guess what? That process still applies to what I do every day at Unsettled, even if our experiences at Unsettled seem to have little in common with journalism.

3. I Intentionally Gave Myself Time

You won’t get anywhere unless you commit to actually doing something. One of my favorite lessons I learned in life was from my college photojournalism professor. “An object in motion stays in motion. An object at rest stays at rest. Get your ass in motion and see what happens,” he said one day when we complained about an assignment. Of course, it’s Newton’s First Law of Motion, but it applies to our lives and how we look at change. If you don’t start moving, nothing will happen.

Giving yourself the intentional time and space to ask the bigger questions, explore new opportunities, and experiment with what’s possible, is the best way to actually start accelerating your next steps – even if you don’t know exactly what they are. Personally, I use a rule I call the “Three Month Rule of Transition”, which allows me a month to simply exist, play, and experiment, a month to start connecting the dots, and a month to start intentionally moving in a certain direction that comes about from the first two months. The amount of time is different for everyone, but the underlying theory stays the same, and I’ve undergone this process multiple times.

If you’re feeling at the edge of something new, and want to give yourself the time, space, structure, and community to actually invest in your next move, then I’d highly recommend joining our upcoming Lifestyle Incubator. Don’t worry… I don’t mind the shameless self promotion, because I truly believe in our process, and am excited to share the journey with you :). I’ve included more below. If this sounds like you, then jump on board. If it sounds like someone you know, share this!

Unsettled’s Lifestyle Incubator is the world’s first 30-day “virtual retreat” that gives mid-career professionals the time, space, tools, and community to navigate through your next transition with intention and clarity.

Through original content, live sessions, group coaching and daily inspiration, we will help you identify the core tensions between the lifestyle you want and the career trajectory that aligns your values, interests, and skills.

If you’re chugging along in your career, at a crossroads, and feel the need to hit pause, assess, and design your next step to maker sure it’s intentional, then Unsettled’s Lifestyle Incubator is for you.


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