Over the past eight months I have been on an “Edventure” – an attempt at jumpstarting my dream career into reality by self-designing a life-changing learning experience. This entailed:

  1. Bartering my skills to do projects for social entrepreneurs and educators in exchange for accommodation, food, and/or living stipends
  2. Living in different cultural environments
  3. Self-directing my learning by creating a curriculum and doing personal projects

When I started, I thought of the Edventure as a cheaper more adventurous alternative to a masters program. It was so much more. I have worked in eight countries (Italy, Germany, Holland, USA, Mexico, Colombia, Panama, Brazil), completed projects that tie directly to my interests in education and social impact, and along the way learned more than in any other period in my life.

I had the idea of going on an Edventure to jumpstart my dream career for years, but waited and waited to act on it. There is a large possibility that I could have never taken the leap of faith. Now, reflecting on the experience behind me, I’ve identified the three keys that enabled me to turn my dream career into reality.

1) Start: With a community

You will never know what you are capable of until you fully commit to pursuing your dream career. Committing begins with one simple but difficult step – starting.

Starting is hard. As a student I became an expert procrastinator, working only the day before an exam or due date. Grades were the incentive to start. When I graduated from college, reality set in – there are no grades in life, there is only infinite possibility. To explore these possibilities I had to unlearn the habits I developed in school.

Suddenly I had to start things not because they were due, but because I actually cared about them.

My ultimate dream career, which I realized after graduating from university, was to empower people through transformational learning experiences. Learning experiences that shattered conventional though of “education” and “school” by incorporating learning-by-doing, cultural immersion, and self-directed learning. This dream laid dormant in my mind for four years when I entered the workforce on a more traditional path.

What finally pushed me to start? There are many factors: spending time alone to formulate a vision, setting a timeline, researching inspirational people who have gone on similar journeys.

All that said, the most important factor by far was community: a huge motivational kick from close friends to push me over the edge and actually start.

Three months before the personal deadline I had set to quit my job and start, I was on a week-long vacation in Italy. Unexpectedly, I received a call from my manager: my company was going through a round of layoffs. I was not affected, but when I found out, there was something inside me that wished I was. Deep down I knew that I could not be productive for the company, nor develop myself, if I continued to put off my dream. I thought to myself: “Just three more months, stick it out.”

I reflected on this notion in a conversation with the two close friends with whom I was traveling. They made three points that pushed me to start, right then and there:

  1. If I didn’t start immediately, I would find some excuse (e.g. a promotion, a great project for a new client, winter vacation) to continue to put off quitting my job.
  2. If I did start immediately, I would be able to do my first Edventure project right away: developing an e-commerce strategy for the organic vineyard we were staying at in Italy (Side note: If you go on a vacation with an open mind, you may come home with a career opportunity)
  3. What did I have to lose? On one side, I’d be leaving a great job and moving off a clear, stable path to leadership. On the other side, by not going, I would be postponing my dream indefinitely – something that I may regret for a lifetime.

In one moment during the conversation, something shifted.

"I will start someday" became "I will start now!"

With this realization, a weight lifted off my chest and I felt an astounding sense of freedom unlike any that I had experienced before in my life. A week later, I returned home, left my job, and packed my bags to return to Italy.

Making the decision to leave a stable career path and take a leap of faith is scary.

It often feels like you will burn the bridges to your old life once you cross to the other side of the river. This couldn’t be farther from the truth. Anyone worth working for, whether in a multinational corporation or in a small non-profit, will applaud the passion and courage it takes to pursue your dream career. Even more importantly, by not pursuing your dream, you do yourself the greatest injustice of all. You don’t live your own life, you live a life that is dictated by those around you.

If I had never started, I would still be living in NYC with a great job, an amazing community, and a dying dream. Since starting, I’ve woken up every morning with a zest for life that I had never previously experience. I am now working on projects that I can put my heart and mind behind, and I haven’t looked back.

2) Self-discipline: The engine that propels your dream career into reality

Starting is one thing, following through is another story. Any successful entrepreneur will reiterate this: ideas are nothing without execution.Ideas are nothing without execution.

When you try to turn your dream into a reality, obstacles fly at you left and right – ultimately it is up to you to overcome them, learn from them, and resiliently march forward.

Sounds beautiful. Not easy.

As students in the traditional school system, we are trained to follow directions to achieve results: do your homework, come to class, and score well on tests to move to the next level. We have schedules. We have a clear-cut ladder to climb to achieve what society tells us is “success.” We are disciplined by the system.

When we pursue our own path, there is no ladder built for us. We must build every subsequent step ourselves before we climb upward in a self-proclaimed direction.

Each step that we build will almost certainly break. To build, climb, and reach the point where our dream has become a reality, we must discipline ourselves.

The first time I walked off the well-beaten path towards societal “success” was when I moved to Buenos Aires for six months to teach English after graduating from university. I had big ambitions for what I could accomplish there, and drafted up some goals and a daily schedule to follow to stay on track:

I drafted up my goals and schedule in a notebook.

During those six months, I failed to turn my dream – to become a Spanish speaking, virtuoso guitar playing, rapping entrepreneur – into a reality. I failed because I lacked the self-discipline and organizational skills to stay on the track that I had carved out for myself. University had not prepared me for this. That said, setting these goals helped me make progress in these areas by reminding me of my intentions. More importantly, the experience of living independently while outside of my comfort zone culminated as the most transformational period of my life up to that point.

Fast forward four years. I’m embarking on the Edventure that I had been dreaming of since my experience in Buenos Aires. Now I have the self-confidence to live independently abroad and more ambitious personal goals to reach. In my first Edventurist blog post I wrote out my goals and summarized my outcomes here:

I came much closer to achieving my goals the second time around.

As you can see, I didn’t achieve all of these goals either. But I did get much closer than my first go around, and the reward (once again) was the most transformational learning experience in my life.

The reason for my partial success?  Self-discipline.

With my first self-designed learning experience in Buenos Aires behind me, I was ready to hold myself accountable and execute on the things that were most important to my development.

The takeaway here is simple: When we commit to pursuing our dream, self-discipline is the engine that will propel us forward. It is the make-or-break element that will dictate success or failure. The beautiful thing about this is that every failure is an opportunity to learn, and if we are resilient and focused, we can reach a level of self-discipline that enables us to habitually turn our dreams into reality.

3) Balance: Realizing your dream career is a marathon

Quit your job. Pursue your dream. Discipline yourself. What comes next?  

An unhealthy obsession.

Almost every entrepreneur I’ve ever spoken to about starting their company has referred to the crazy work-dominated lifestyle they needed to assume to make it happen. They speak of this with massive bags under their eyes, their minds moving at a speed approaching that of light.

When building a billion dollar business is the motive, it’s easy to fall into this way of being. You are so excited to make something big that you work non-stop. Eventually, you burn out.

When pursuing a dream career that is not money-focused, you can take a different approach: balance.

Balancing each day of my Edventure was the center on which my happiness and ability to do meaningful work depended on. This entailed: 

  • Finding a healthy routine for the mind and body to sustain positive energy throughout the day. Adequate sleep, yoga/meditation in the morning, a plant-based diet, and some form of movement in the evening (e.g. dancing, running, soccer). This routine was the glue that held the rest of my days together. It was striking how much my productivity and creativity suffered when I missed just one piece of the routine.
  • Setting aside a time each day for creative inspiration and expression. Some days, this entailed playing guitar and journaling alone on a beach. Other days, it was reading a novel that was completely unrelated to anything I was working on for my Edventure. Regardless of what it was, flexing the creative side of my brain unleashed ideas that were invaluable to my productivity and overall sense of fulfillment.
  • Dedicating sections of the day to two types of productive work:
    • Mornings and nights for making: doing work that required deep thinking, significant levels of focus, and big blocks of time (e.g. designing curriculum, writing blog posts, doing research, etc.). What Paul Graham calls the Maker’s Schedule.
    • Afternoons for managing: doing work that required quick thinking and multitasking (e.g. responding to emails, having meetings, booking flights, etc.). What Paul Graham calls the Manager’s Schedule.

Maintaining my balance was difficult to manage while on the road – from Couchsurfing in Berlin to sleeping in a tent in the Panamanian jungle. That said, consciously incorporating these elements into my day-to-day routine made the long journey more fruitful than I ever could have imagined. I never once tired out and considered going back home, because I felt mentally and physically nourished.

Ultimately, turning our dreams into reality is a marathon, not a sprint. If we dream to make the world a better place, we will endure long, difficult journeys. To push forward to the finish line, we must be our best selves along the way. We must first find balance in ourselves before we start to balance the world.  

There is no secret recipe for turning your dream career into reality.

As individuals who aspire to change the world for the better, the only way for us to begin is to experiment. We must try different types of work to understand what fulfills us and actually benefits the environments around us. Self-experimentation has lead me to three key elements for realizing my dream career: starting with a community, self-discipline, and balance.

Ultimately you will have to discover the keys that you will need to turn your dream career into reality. I hope that the three keys that I came across will give you a solid foundation to open new doors.

All that’s left for you to do is start.


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