[swa14]

Not silly. It's supposed to be this way. And don't skip out on the angst.

A starting businessman should be apprehensive of sending out invoices and questioning himself. Yes, it does feel like "begging", but it makes sure you don't lose out because of hubris. Over time (if you're doing everything well) you will have more money and business acumen, and it will become easier, since you won't be needing the money on the short term. It will also allow you to better negotiate higher prices.

And when you've mastered it, you can hire a (part-time) secretary, who sends out the invoices. That's your reward. You faced your fear, learned how to handle it, and now you can let it go, because with someone else doing the billing, you can always fall back to it being a secretarial error.

There are whole industries based on making it seem you have enough cash and confidence so you feel you have a stronger position to negotiate, skipping out on what I feel is a basic business skill.

Or you can do it the hard way, without leased luxury and practicing the voodoo feelgood technique of the day. Building a business on hard work and gathering confidence in your own skills through your customers, without blaming your parents or the world or your mirror.

Dont' be an actor playing an entrepeneur; be an entrepeneur.

[wpietri]

It is not supposed to be so hard that you have to get drunk before doing it.

I agree that you should face your fears. But if you have fear to the point of paralysis, I think telling people just to man up is bad advice. It's like the dieting advice one gets from people who have never been fat: plausible on the surface, but ultimately it comes out of ignorance.

I also agree that one shouldn't blame one's parents or the world. But that's different than understanding how one's relationship with one's parents has shaped you.

[zcvosdfdgj]

A starting businessman should NOT be apprehensive about sending out invoices. There is no shame in asking for someone to pay for what they have purchased.

REMEMBER: you're doing them a favor by not forcing them to pay up front. A 30-day same as cash policy is worth {cost of capital}/12

If you think reminding the customer about their bill is "begging", "only a business necessity", or whatever, you are wrong.

Ask yourself: when was the last time you bought something and thought the store was begging by asking for payment. Safeway is not greedy, begging or anything of the sort when they ask me to pay for a loaf of bread. And you are not being greedy by asking for payment for your work.

[swa14]

>>There is no shame in asking for someone to pay for what they have purchased.

True, but what have they purchased ?

>>Safeway is not greedy, begging or anything of the sort when they ask me to pay for a loaf of bread.

No, but that's a loaf of bread, a physical thing with uniform properties and an established price. When you send out an invoice for your freelance work, there is the amount of hours and there's significant markup for it being freelance hours. It adds up, and before you know it you're sending out a bill for what is, at that moment in time, for you a huge amount of money.

It's not a bad thing to reflect on that. "Am I really worth this ?", "Did I actually earn this?", "Am I offending my customer by being out of the ballpark ?", and most importantly, "Can I justify this, not just to the customer, but to myself ?"

Over time you will appreciate how you fretted over that "huge bill", and maybe even adjusted it a little to feel comfortable about the value you feel you have provided.

It's not comparable to retail, where everything more or less has an agreed upfront price.

[alpine]

Your argument is completely rational. Isn't the point, though, that these feelings are irrational? I don't think telling yourself to stop being irrational is the best way to address the problem. Once you have debugged the cause of the irrational belief/behaviour then it might be easy to tell yourself you can now take the desired, rational step, no?