‘œGoing Two Feet In’ is a euphemism among entrepreneurs for letting go of the day-job safety net. Going two feet in isn’t something every weekend entrepreneur will be able to do; it isn’t something all weekend entrepreneurs want to do. Also what it means to go two feet in varies from entrepreneur to entrepreneur. The process of successfully making the transition from having to rely on the day-job to not having to rely on the day-job also varies from entrepreneur to entrepreneur.

About every weekend-entrepreneur-turned-full-time-entrepreneur I know describes a transitional process that began with finding ways to cut back on auxiliary life-commitments in order to focus on building a weekend-enterprise. Ryan Healy, a successful entrepreneur recently featured on the news show 60 Minutes, wrote about cutting back at work in order to help manage the transition. Paul Wesselmann, about to wrap up his tenth year of being full-time as an entrepreneur, tells a story about how he found a four-day-a-week job which freed extra time for his business. I started mine almost a year ago when I was a year away from graduating law school — being a student provides the ultimate in flexibility. Maura Cullen, now over twenty years into being full-time as an entrepreneur, did the reverse of me by going full-time in business but then using that freedom to complete a Phd. Another strategy, utilized by a dentist friend of mine Dr. Tamim Sifri of Smart Dental, is to keep a one-day-a-week job even after opening a successful practice where the ‘˜side-job’ provides access to inexpensive health insurance.

Some weekend entrepreneurs rely on the support of spouses or family members before building a business sufficiently productive to support themselves and their family. Kate Liu, owner of a meeting planning and consulting firm, follows this model. Another outstanding entrepreneur Sam Davidson, founder of CoolPeopleCare.com, speaks about the freedom and flexibility that came with his wife keeping her full-time work as he was getting ready to go two feet in.

I recently spent some time listening to Sam speak and had a chance to chat with him when he visited Madison, WI. The title of Sam’s talk is Making Your Passion Your Profession and it gives specifics on a four-year process that worked for him in getting ready to go two feet in. Consistent with the experiences of others I’ve interviewed, the process is not a one-size-fits-all solution. Sam says processes ‘œrequire constant examination and frequent review and reflection.’ This means that nobody’s experience will be just like the next person’s. The following is an outline of Sam’s four-year process and my thoughts on each of the years. Sam’s thoughts are available here.

Year One: Dream while learning the ropes. Some, well many actually, have probably already completed year one. During this year the aspiring entrepreneur takes a position that will provide exposure to rudimentary business skills and concepts. In this year it is important to learn about everything from spreadsheets and balance sheets to sales and really good customer service. For most, this step would occur after college, or after dropping out of college — or maybe dropping out of grade school like Erin Davies recently did. Remember the process is different for everyone: I spent a total four years of my life on this step if you count my time in law school.

Year Two: Get the skills needed to live out your passion. In this year the aspiring entrepreneur learns some intangible elements associated with living out your passion. A typical scenario for this year is where the aspiring entrepreneur’s basic skills combine with the dream within the context of a larger organization that provides a day-job. On this part of the process Sam says ‘œthis is a key time for networking and meeting people that can help you once you get to the planning stage.’ Some folks might accomplish the objectives associated with this year during or before college. I spent about eighteen months on this portion of the process in three separate day-jobs including one at Mother’s Against Drunk Driving.

Year Three: Start to plan your passion and take risks. For me, I spent the summer of 2006 working on the bulk of this year’s objectives. I still remember the sit-downs with my mentors to go over the basic business model. The spreadsheets will make you dizzy. Sam says that during this year ‘œaccidents happen, and the unexpected occurs.’ Accidents are a good though. Staying focused but flexible will help in taking advantage of accidents when they do happen.

Year Four: Put the plan into action as you set out on your own. This year looks and sounds a lot like running a business. If your passion truly involves providing a product or service for which there is a market then this year is also the year to start collecting revenues; your passion is now your profession. This is the year that Sam keenly points out that you are ‘œaccountable only to yourself, which is a blessing that is bloated with responsibility.’