I think I can relate to his fear of sending out invoices. I had the same fear not with sending invoices but more precisely pricing proposal. I would fear that my prices would be too high, that perhaps I would lose the job because of that. That maybe (deep thoughts) that I wasn't worth the money I was asking for (Thankfully I'm not longer thinking this way).
And every time I would send that pricing proposal only after re-reading it 10 times to make sure I leave enough space so I can back down without looking like a total idiot, I would receive an email accepting the pricing proposal and thus re-enforcing that I wasn't charging too much and that everything was ok.
It's important to understand that through your pricing you are setting the perceived value of your services. If you price them too low, people won't bother taking you because their perception of your value will be low. If your price is too high you might be perceived as too greedy.
The last part of your blog post resonated really well with me as well, as an entrepreneur you need to build an entourage of good people who can support and help you overcome you inner fears but also challenge you when they think you're wrong. You need a winning team.
I'm shocked that in the last five minutes the two comments on this post so far are both from people, who, like myself, and the friend in the article, worry about sending invoices!
I thought it was just something I was struggling with. It's re-assuring (in a strange way), to know that these are fears that a lot of people have and not just myself. Fortunately my Mrs won't let me get away with not pressing that big nasty send button!
It's indeed re-assuring to find out that your fears are not unique and that many other people think the same way you do. I think basically that people fear anything that is related to money.
I found that the hardest part is not about sending invoice tho, but the hardest part is to actually collect the money. I once dealt with a company I needed to collect money from for a job I did, it took me 364 days (yes, almost a year!) to get the money wired. Thing is it could have been dealt faster (it was part my fault as well), but I kept delaying talking to the people in charge of accounting because I really didn't like the though of begging for my hard earned money.
Part of that fear by the way is derived from the fact that you still want to retain some kind of good relationship with the company/individual and you wouldn't want to harm any potential future jobs. However if you're not getting paid instantly, would you really keep working for the same guy?
I have a rule in my company, we pay immediately after the job is done. We don't wait 1 week, 2 weeks or 60 days like some other companies. We pay immediately and I think so far it paid off since freelancers like to work for us.
"but I kept delaying talking to the people in charge of accounting because I really didn't like the though of <b>begging for my hard earned money</b>."
I think this is exactly the problem the article is talking about. The idea that asking someone to pay for something they purchased equates to "begging".
I've never had this problem (I've sent out invoices for $5, and if you're a day late, expect to hear from me the next day.. it took 2 invoices to collect that $5, btw).
I think it's helpful to put yourself in their shoes. Could you imagine calling one of your freelancers, having them do work for you, and then not paying them? When they call, would you think they were begging for their money or being greedy?
Of course not. If there's no dispute about the work, then you know you owe them money. You know you never paid for the product you purchased.
I don't think of Safeway as greedy when they ask me to pay for a loaf of bread. And I wouldn't expect a customer to think I'm begging when I remind them they haven't paid their bills.
I think I can relate to his fear of sending out invoices. I had the same fear not with sending invoices but more precisely pricing proposal. I would fear that my prices would be too high, that perhaps I would lose the job because of that. That maybe (deep thoughts) that I wasn't worth the money I was asking for (Thankfully I'm not longer thinking this way).
And every time I would send that pricing proposal only after re-reading it 10 times to make sure I leave enough space so I can back down without looking like a total idiot, I would receive an email accepting the pricing proposal and thus re-enforcing that I wasn't charging too much and that everything was ok.
It's important to understand that through your pricing you are setting the perceived value of your services. If you price them too low, people won't bother taking you because their perception of your value will be low. If your price is too high you might be perceived as too greedy.
The last part of your blog post resonated really well with me as well, as an entrepreneur you need to build an entourage of good people who can support and help you overcome you inner fears but also challenge you when they think you're wrong. You need a winning team.