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In 1981, I set out to create what is often referred to today as a ‘lifestyle business’. back then, I just knew that I hated the corporate world, and that it was not where I wanted to spend my days, much less my life.

Why? That’s a long and complicated tale, but suffice it to say that it was not because I was not good at playing the corporate game. On the contrary – I was too good at it, and rose to top positions in every job I held. The problem was that a) being good often meant salaried jobs that fell outside of the 40 hr work week/overtime laws and b) I did not like playing the political games that accompanied being successful in that world.

My goal was to create a portable income – one that I could run/manage/build from anywhere. Since this was before the internet, I started out with mail order businesses, which I was very successful with.

Fast forward a few years and I discovered the web – by 1992, I was selling websites to real estate agents in Silicon Valley, and by 1998, I launched a very successful networking website for women entrepreneurs, which I sold a few years later for a very nice 5 figures.

I have always enjoyed working from home and have never missed the office environment. But that is NOT typical as I have come to learn over the years. I have seen many very promising start-ups shelved when the home-based business owner realized that working from home was simply not working for them.

1) Do I really want this bad enough to overcome the challenges?
This is so critical! Is having your own business important enough to you that you are willing to put in the long hours, endure the solitude, take ‘multi-tasking’ to new levels of ridiculousness because you are your whole support team/editor/copywriter/webdesigner/etc?

2) Am I willing to live outside of my comfort zone on a continuing basis?
Successful entrepreneurs take risks like others take coffee breaks, with regularity and without giving it a second thought. Can you do this?

3) Can you survive without the ‘Water Cooler Crew”?
This is probably the number 1 complaint that I hear: people miss the constant interaction with other people. I never did, but in large part it was because I am comfortable making decisions without needing the constant feedback of others. If that is not you – look into local breakfast networking groups, Meet-Up etc to build a support group of others in similar situations.

4) Do I have enough confidence in myself/my idea to weather the comments and opinions of friends and family?
Having the support of your spouse/partner/signifcant other is important – but do not underestimate the impact of comments (usually disbelief or sarcastic) of friends, family and coworkers when you announce your plans. Here’s something that you need to truly understand at your core: You are taking action on something that 99% of them wish they could do, but never will. Your action will make them uncomfortable because it will point out to them what they have NOT done….in other words, you are bringing their own personal failures out of the shadows to be examined in the bright light of your actions. Making fun of you will make many of them feel better, even though they may not consciously be aware of what they are doing. So just smile and go along with them – as long as you believe you can do it, that’s the only thing that matters.

5) Am I ready to direct my own life?
This is sooooo important! Can you handle setting your own goals and work schedule? Do you need others to pump you up when you hit a hurdle or the fear of getting fired to get you on point for the day? Here’s my shocking truth: I am the most demanding boss I have ever worked for!! LOL – that is seriously the truth, and why I have been able to do what I do for so many years. I expect more from myself than anyone else would, and that’s ok. I love what I do, and have built a business that produces revenue for me no matter where I am or what I am doing.
For me, the rewards continue to outweigh the challenges. When my parents have had health issues, I have been there for them, including spending 3 months staying with my mother 1500 miles away from my home office, while she was recovering from a broken ankle and knee replacement. I spent the summer running my business from my ipad! I can leave early to see a grandson’s baseball game, and still catch up with any urgent issues from my phone.

All in all – this is a great way to live – but it does take determination and dedication to make it your lifestyle!