Successfully Self-Employed: How to Create a Lifestyle Rather Than Just a Living

In the past week or so, I've had three distinct occasions to speak with others about the joy of being self-employed and working from home. The first came about as a result of being interviewed by a newspaper reporter from Berkshire (MA) Eagle. One of the questions he asked was about the earning potential of people in the Virtual Assistant industry (the interview was about the side of my business where I'm an Internet Marketing Virtual Assistant). I gave him the upper tier of earning potential of the busiest VA, and when he asked if I earned that much, I told him, "No, I don't. That would require me to work way too hard." However, he seemed to be most impressed by my intangible benefits of self-employment, in which I said: "What's cool about my business is that I don't have to commute to work. I work the hours I want and with the clients I want. I save money and time on traveling and gas. And I can work in my bathrobe."

The "working in your bathrobe" theme appeared again in a conversation with a client this week, who was lamenting her early 6 AM departure to a business appointment. She said, "This (early hour) is tough, but I know people do this every day to get to work. I'm never up this early. I finally walk into my office at 9 AM in my bathrobe with a cup of coffee in hand and maybe take a shower around noon." This sounds suspiciously like my life on many days.

The third occasion was with my sweetie, who told me how jealous he was that I show up to work about 9 AM, knock off between 4-5, only work 4 days per week with clients, take breaks during the day as needed, work in my bathrobe (see the recurring theme here?) and yet still manage to make a decent amount of money. He, in contrast, works 4 12-hour days (or nights, actually, as he works many graveyard shifts), is off 3 days, is bored out of his mind at his job, and has to endure the bickering and fighting and backstabbing politics that make up the workplace. He constantly refers to himself as "being owned by the man". That seems like so much fun I can't stand it.

In the 7 years I've been in business (wow, it's hard to believe I've been self-employed for longer than I've ever had any job!), I have been approached by well-meaning friends, colleagues, and business associates who have cajoled, encouraged, and coached me to "grow" the business. By this they mean create an enterprise in which I go out and find clients and farm out the duties to a bevy of independent contractors. As someone who supervised both directly and indirectly 70 full-time, student, and part-time staff in my higher education career, I swore I would never be in a supervisory position again where I had to manage that many people. It just wasn't fun.

I'm a firm believer in the "small is beautiful" concept of running a business. Granted, what I've done in my business is to create a job, rather than a business, but that was done purposefully. Chellie Campbell expresses similar sentiments in her new book, "Zero to Zillionaire", "There are 17.

5 million of us solo-preneurs in the United States. The ads say, 'Go big or go home.' Bah. We already are home. With work we love, cash in our pockets, and family around us --happy, rich enough, and fulfilled.

"What's standing in your way of "going home"? Initially for me, it was fear. Fear of failing. Fear of losing my health insurance. Fear of being financially decrepit. Fear of losing respect of my former work colleagues. Fear of simply not being able to pull it off. What propelled me to follow this dream of being self-employed? Finally discovering an industry that would enable me to do what I loved to do, what I was good at, and used my natural skills and abilities. The discovery was a long time in the making, as I failed miserably in my first business venture when I followed the advice of many of the self-help business books to create a business from a hobby.

Guess what? Most of my fears have been realized. I have failed in starting a business. I have lost my health insurance. I have been financially decrepit. I have lost the respect of some former colleagues (though most are jealous of my new-found freedom ). I have failed at always being able to pull something off. But, nothing killed me -- I have survived. It's like learning to walk -- you pick yourself up and start again.

What I discovered in my journey was that I was creating a lifestyle rather than a living. I'll probably never get rich from what I'm doing, nor will there be any business assets to sell upon my death, as I am the business, but I'll die happy and fulfilled and doing what I love to do, and plan to do it (or some type of business) well into my 80's. Traditional retirement like my parents have had sounds terribly unappealing to me, and extraordinarily boring.

If you've been sitting on the fence, with those dreams of self-employment floating by just out of reach, here are 7 strategies to consider if you'd like to create a lifestyle, rather than a living, for your life:

1. Where are you living? Is it a large urban metropolis, small city, or rural town? Is it on the coast or in the mountains? What kind of home do you reside in? Is it a comfortable townhouse downtown, or a patio home in the suburbs?

2. What's your ideal neighborhood? Do you live in a bustling part of town where all the action is, or do you live in an area where everyone knows your name? Are you close to convenient shopping, or live isolated out in the country?

3. What does your community look like? Are you active in many civic organizations, or do you spend a great deal of time at your children's athletic events? Are country clubs and social groups a part of your network, or do you prefer to socialize at your church or temple? What do you do for fun?

4. How are you connected to the world? Do you travel extensively, or are local day-trips how you spend your time? Are you politically motivated? How do you show it? How do you participate in/impact what's happening in the world around you?

5. What do you love to do, and what are you good at? Are there activities in which time seems to mysteriously disappear when you're engaged in them? Are you doing it alone, or with others? Do you work from home or an office? Do you want to work for someone else, own your own business, work with a team, create a giant company, or work as a solo practitioner? Who needs the skills and activities that you're good at/love to do? How much will they pay for it?

6. What does your ideal day look like? Who surrounds you? What are you doing? With whom are you doing it? Where are you?

7. How much money do you want to make? What would make you comfortable? What kind of life would you really like to lead if money were no object?

I did an exercise very similar to this in 1998, after the failure of one business and just prior to starting my current business. I ran across the journal containing my answers in 2001 or so, and was amazed at how much my life now resembled what I had written down as my vision 3 years earlier.

If you're stuck and hate the direction your life is headed, take an afternoon to daydream and create your vision. I realize I'm now ready for my next chapter, so it's time to dig out that journal and get to daydreaming again.