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How to Leave Your Job (and Follow Your Dream)


So you want to leave your job. And why not? What we crave is flexibility, freedom, feeling valued, creative self expression, connection, purpose and meaning. I believe that we all have unique creative gifts to contribute to the world that are desperately needed. And because the job you will hold in ten years likely does not exist today, there is no better time to get dreaming and start executing.


If only you could find a way to leave where you are now (the steady pay check, the health insurance) and fast forward to your dream career without fear and self-sacrifice... I'm here to tell you: it's possible. I left a secure job to strike out on my own - pursuing my purpose and creating a career path I never thought possible - and I have not looked back. Not once.

Below, I have summarize the best practices I learned through paving my own path (and now coaching dozens of others on this journey) that may help you forge your own future career:

1) It takes 18 months. I often field the question: How long does it take to start your own business and forge the new path? With determination and dedication, 18 months seems to be an accurate and realistic planning window. Start by drafting an ideal scene - a written vision of what you want the picture to look like 18 months from now. What do you imagine your day to day to be like? How will it feel? What does a thriving venture look like 18 months from now? What will change in your life today? Then begin to work backwards from this time frame.

2) Every day, take one small risk. Early entrepreneurs imagine that success along a new path will look like a flying, courageous, giant wins: Landing the major investor. Booking a $10,000 client. Putting in your notice in at your current job and sailing off into the sunset of your smooth new life. However, what most underestimate is the number of persistent, tiny, bite-sized steps on the path to success, which is the actual (and only) way to make change happen. When you set out, aim to complete a small task, one step or risk, on the path to your dream each day. Make one phone call. Google one new idea. Set up one meeting. Take a task and break it down until it feels doable; then track a risk you will commit to taking each day.

3) Get clear about money. Most of my clients have doubts and worries about money when it comes to striking out to pursue their dream. These doubts can quickly crush the most nascent plans and tender dreams before they even get off the ground. The first thing to do is take an objective (neutral) look at your financial situation - estimating your projected revenue in and minimum expenses out at based on your ideal scene. Map out a budget. Get a realistic picture of how many months of savings, for example, or how many revenue streams you will need to get the business off the ground and start to take steps to support it.

4) Build your emotional scaffolding. For me, emotional scaffolding is comprised of cheerleaders, supporters, mentors, coaches and friends - inspirational peers who will hold you up when the going gets rough. Start building these relationships and recruit them into regular conversations as a way of asking for help, keeping yourself inspired and accountable. My scaffolding is comprised of a coaching circle of peers, mentors, my own professional coach, and a leadership program to keep me on track and connected to my best self.

5) Take the leap of faith. No matter how well-planned, how intentional, how financially prudent we have been about our transition, the act of walking away from the known to the unknown will likely still make you break out in sweat. Our ancient, risk-adverse animal brain will still send all the same panicky signals of being chased by a saber-tooth tiger when you get close to giving notice. This is not a sign that you are on the wrong path, in fact, this kind of fear can be anticipated, welcomed and dealt with compassionately. Turn back to your leader self, to your larger purpose and the people/places/things that remind you that you are on the right track and stay the course.

The path is certainly not for the feint of heart, but nor does it have to be excruciating or desperate or painful. My experience has led me to believe that with the right mix of consistent, iterative action and inner tools for staying connected to your heart and confidence, you can forge a new path that represents your most fulfilling life.

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