Photo: Geoff Wong http://www.flickr.com/photos/keepwaddling1

Like many of you, I used to report to an office five days a week, clocking in from 9 to 5 and often commuting long distances to get to work. I did that for more than 20 years. For a while, I was lucky enough to have a stint as an executive director that afforded me a lot more freedom and creativity, but for most of those years I worked for someone else and operated in the confines of job descriptions that I hadn’t created and usually didn’t resonate with.

Then, in the last few months of 2007, the nonprofit I worked with went through financial and staffing turmoil. The end result: I lost my job. I was stunned. I had worked with this organization for more than six years and given my heart and soul to their cause. Sure, other people lose their jobs, but I never expected that would happen to me. It took a long while to get through that shock.

Even before I could fully process the loss on an emotional level, the very practical challenge in front of me was: What will I do now? I felt like I had been pushed off a very big cliff with a very small parachute.

I had some savings but not enough to get through more than a few months before I needed to bring in some income. And I didn’t have anyone else’s salary to fall back on. I scoured job listings and sent out a batch of resumes, but heard nothing back. This was in early 2008 when the economy was beginning its nose dive.

Rather than continuing to look for other jobs, I decided to take a leap of faith and create my own business — Five Directions.

In the three years since then, I’ve successfully made the transition to running my own business and being self-employed. It hasn’t always been easy, but it has been one of the most rewarding experiences of my life. I love being able to decide what I want to create and focus on each day, as well as following my natural rhythms about when and where I work.

Many people don’t get how I’ve been able to make this happen or even how I can survive. I completely understand their bewilderment and remember it well myself. When I was in the role of an employee for all those years, the world of people who worked for themselves seemed like another universe. For the life of me, I couldn’t fathom how to get from “here” to “there.” I wondered –

• How do these people make enough money to live on?
• How do they find work?
• How do they take care of things like health insurance?

There is a certain amount of safety (or at least perceived safety) in working for someone else, but it comes with a big cost. Now, in retrospect, I consider the loss of my job one of the biggest blessings of my life. Having been pushed off that cliff, I was given the opportunity to fall or to fly. In the process I learned that I had wings and I learned how to use them.

If you’re thinking about making the leap to self-employment, or if like me you find that the job security you thought you had has disappeared, here are five things I’ve learned to make the transition easier:

1) Find Mentors and Role Models

Before we can bring something into being, we need to have a vision that it’s possible. One of the best ways that of doing this is to get to know people who have transformed their lives by building their own businesses. You can probably find these folks in your own community, and you can certainly find them in the vast Internet community. Here’s one good example: Pam Slim, author of the book Escape from Cubicle Nation: From Corporate Prisoner to Thriving Entrepreneur and the blog of the same name. Another great place to start is the Unconventional Guide to Working for Yourself, created by Chris Guillebeau, and if you’re really ready to dive in, check out Chris’ Empire Building Kit.

I’ll be introducing you to more successful entrepreneurs in the Liberated Life Project and mining their stories for lessons we can learn from them. The main point here is to start surrounding yourself with people who have made the leap rather than with people who are still stuck in “working for someone else” frame of mind.

2) Create a “Freedom Fund”

A “Freedom Fund” is a savings account that will give you the cushion you need to make a choice about your next professional move from positivity rather than fear.  I was grateful that I had started saving for just this purpose the year before I lost my job; it made it more possible for me to make that leap of faith and start my own business. If you already have such a fund, good for you. If you don’t, start now. Rather than treating yourself to a not-very-healthy latte several times a week, how about putting that money in your Freedom Fund? How about your cable TV bill…do you really need all those channels? So often, we are lulled into complacency by things that give us short-lived immediate gratification. Ironically, paying for these things keeps us in work situations that deaden our spirit. It’s a vicious cycle, but one that you can make the choice to break.

3) Develop an Entrepreneurial Spirit

More than anything else, this is the key ingredient to succeeding at working for yourself. Your attitude in all things needs to be: “I can do this!” During the past three years, I’ve found my inner entrepreneur and learned what a wonderful thing that is. For me, this means:

• Making things happen rather than waiting for them to happen to me
• Being more comfortable with uncertainty
• Being willing to learn from my mistakes rather than be overwhelmed by them

4) Get Clear on the Kind of Work You Want to Create

The classic equation is:

Something that you are passionate about and good at doing +

A problem that you can solve for people =

Successful self-employed livelihood

There’s a reason why it’s classic – it really works. Spend a good deal of time thinking about that first part of the equation – what is it that you’re good at and feel passionate about? You may want to ask people who know you well how they might answer that question for you. The second part is equally important – how have you actually helped people in ways that they have needed and appreciated? Finding the intersection of these two will give you some ideas for your new business.

5) Use Your Past to Create Your Future

Make a list of everyone who has ever appreciated the work that you do. This might include former bosses, co-workers, and customers. Then start contacting these folks to let them know about your new venture. Ask them if they can help spread the word about your business – and at the same time find out if there is anything you can do to support them. Make it a practice to never ask for more than you are giving. This will pay off in the long run.

In future posts, I’ll go into more depth on each of these steps but here I want to give you a map of what’s possible.

If you are someone who has successfully made this shift to working for yourself, how did you make the leap? What has worked for you that you’d like to share with others?

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