When to Bail Out or Stay the Course

This time last year, I was in the process of creating a huge and seemingly crazy dream. I decided in August of 2012 that I wanted to leave my job and my life in San Francisco and sail in South America. I had no idea how to sail.

Very long story short, I found myself living the dream 3 months later, crewing with a friend for a fantastic skipper in Mexico. It was one of the most glorious experiences of my life!

What’s more, this exact time last year, I had a choice: bail out on my dream or stay the course. On the surface, things did not appear to be lining up. I had taken sailing lessons in San Francisco and had hoped to crew for a race called the Baja HaHa (one that goes from San Diego to Cabo, Mexico). That didn’t materialize, so I found myself in a similarly depressing state to the one that ultimately sparked starting this “6 Month” experiment in the first place—on my mom’s couch in Atlanta.

I had a choice. I could bail out on my dream or I could stay the course. I really wanted to sail! When moving to San Francisco 3 years before, I was reading The Alchemist. In the beginning, Coelho talks about the universe coming to your aid to help you achieve your dream or personal legend as he describes it. In the end, the universe tests your dedication, and that’s where most people give up.

Boat Sunset

What most people don’t know about me getting my dream job 5 weeks after moving to San Francisco on New Year’s Eve with a little over a $1,000 and a place to live for a month, is that in order to continue the interview process I was undergoing, I signed on to take care of a black lab-chow mix named Sparky while her owner went on a yoga retreat in Thailand. It was the only way I could afford to stay. What almost no one knows, is that I was also down to eating two meals a day and the day I started my job, I had $200 left in my bank account.

Back to sailing! I wasn’t giving up. I was willing to fly to Cabo, show up at a crew party, and wear a sign that said “Will Crew.” That’s how much I wanted this! A week later, I remember doing a meditation asking the universe for clear next steps. The next morning, I received an email from a good friend saying a girl had dropped out. I was in! I bought the ticket that day and flew down a few days later.

How Can You Tell When to Keep Going or When It’s Time to Do Something Else?

Every dream has a trajectory. It’s important to be clear on your vision and destination but be open to how it manifests. In other words, adjusting course. You can fight the wind and waves or you can make them work for you.

Ask yourself: 

1. How much do I want this dream to come true?
2. Why do I want this dream?
3. What am I willing to do? And where do I stop?

When crossing the Sea of Cortez, there was a point where there was only ocean in all directions. We trusted our compass and GPS to know that Mazatlan was ahead, but there was no visual confirmation around us. If we had doubted our navigation system, perhaps we would have tampered with the direction or freaked out and turned around. Your ultimate guide is your heart. It is your soul’s compass, and it knows the way.

We trusted. And hours later, we saw land.

What are some your experiences in creating your dreams?