One of the reasons I knew many years ago that I had to become an entrepreneur, was that I wanted the ability to dictate the terms of my life.

I hated HAVING to be at work at 9am, and feeling guilty and stressed if I was running late. I hated having people silently judge me if I was writing a personal email or reading a blog during work hours, and the challenge of having to always book things like dentists and home deliveries in my pre- or post- work hours. Its not that I have an aversion to work, far from it, but I hated that the times I was not performing in a ‘normal’ business way would be judged negatively. And perhaps this is more an indication of my inherent guilt, as possibly I was imagining these silent frowns of disapproval, but nevertheless, I hated feeling that way, and knew that being my own boss would be the only solution.

And I feel very lucky to have achieved my goal: I am my own boss, and I am more or less master of my own destiny.

Of course the irony is that far from working less, I am now working MORE than I ever did, when I was a normal employee. The beauty of my arrangement though, is its on my terms, and every day that passes I savour that feeling. I love that because I work best in the evenings, if I choose to start work at 10:30am, and work til 9pm, that is fine. If I need to go to the doctors, I can book at whatever time I like, and work from home til that time comes. What freedom! And if the way I work best is to stop every hour for a game of Spider Solitaire, no one is going to ever judge me. Brilliant!

The one big challenge though, is that this freedom requires a great deal of self-discipline. I love working and I am inspired by my work, but sometimes, my inherent laziness gets the better of me. Never is this more apparent than when I ‘work from home’. Now, don’t get me wrong, my working from home is vastly productive, and I enjoy the solitude to focus on something complicated. But… the lure of tempting procrastination is strong, and I find it hard to resist even though I really really want to, without the power of the guilt I feel when I am working in an office.

So, although I work for myself, being in an office with lots of other super dynamic people not only motivates me, but dispels my desire to procrastinate. I actually find the rigours of my training as a 9-5 employee actually helps and gives me discipline to go to work early, work hard, etc. I know some people are brilliant at working hard at home, and are great with self-discipline, but I have come to terms with the fact that for me, I need to almost trick myself that I am going to a normal job, in order to get the most out of my time. Of course, I do give myself some of the flexibility I have aspired to, and in all, this proves a healthy workable balance.

How do you know who to trust?

Being a naturally trusting person (some may say naive), I tend to trust everyone. “Surely they just want to help? Surely they have my best interests at heart?” And I guess I’ve been lucky in that, for the most part, I haven’t been completely screwed in the past as a result of this naivety.

However, now that I have a business that is potentially lucrative, I cannot help but be suspicious of people’s motives. “Are they helping because they want something out of it? Am I meant to be rewarding them for their advice? Is their advice tainted because they want something out of it?”

I couldn’t help it. I had been in places like Egypt, where the ‘baksheesh’ is part of the culture… where you are meant to line the palms of people who give you unrequested help. Its such a foreign concept to us westerners – we pay for things we request, or for things we choose to give to (charity, buskers, etc). But to pay someone because they approached you and gave you unasked for advice on the streets of Cairo, was always something I hated, especially because it made me suspicious of every person that was nice to me… are they only nice because they expect a baksheesh?

So here in the business world, it sometimes feels like I am on the streets of Cairo. I naturally assume if someone introduces me to someone who turns into a customer, that they were doing it to help me out, but then I discover I am expected to pay a significant commission. I find people so willing to help, and then I find myself wondering what the expectation is to reward that assistance, or whether its genuinely altruistic.

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The challenge with starting a business using your own savings, is you have to try to achieve elegance while being stingy.

A few of my challenges at the moment:

I need a legal opinion on my site so I can get public indemnity insurance. Just to get the Terms of Use document written is $4000. I do not have this money. I also need further advice to avoid being sued for copyright infringement, which with my type of site, is a risk. I cannot afford to do this – perhaps later when/if I have secured venture capital funding or when the site is making money, but right now, this money does not exist. So I have been asking my lawyer friends to help, which has meant I have my Terms of Use document written, but they don’t feel very sure about the copyright protection side of things. I am taking a gamble that I will be safe for now.

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I’ve been working on my little business for the past 8 months or so now, and most of that time was spent developing the idea and getting it ready for development. So here are my top 5 learnings that I have gleaned in that time: (more…)