Don't Be Afraid to Ask for Money

I'm busy with a bunch of projects these days, and that's a really good thing. Looks like I'm going to skooch in under the wire again this month and make my bills. Next month might be even a bit better if it ever stops snowing. You gotta get out there. The snow can make that tough, though if I weren't busy and needed money, it would provide a ready opportunity to pick up some cash. I'd be trudging around with a shovel looking for un-shoveled walks, banging on doors. You can't afford to be shy or proud when the name of the game is survival.

On that note, let me just drop a little pearl of something resembling wisdom (I would never publicly impute wisdom to myself):

A big part of making it in this world without a job is having the guts to ask for money. I've never been comfortable asking for money. When you have a job, it just comes. When you don't have a job, you have to go out and get it, and that can be uncomfortable for someone who has always just assumed the money would show up in their account every two weeks.

The toughest part of trying to start your own business can be billing and collecting. In my case, all of my clients are companies with under 3,000 employees -- small to medium-sized companies. The smallest ones are restaurants and other local businesses that I know are struggling with cash flow these days. It's tough to ask another entrepreneur to pay you sometimes, even if you've done something amazing for them. I like everyone I work with, and I suppose they like me which is part of the reason we do business with each other.

Bottom line, though: It is business. I'm not doing work for my clients out of the goodness of my heart, and they're not expecting me to do that.

Don't be afraid to send that invoice. Don't be afraid to call for your money if it is not paid promptly. Whatever you do for your partners and customers -- whether it's cleaning their toilets or overhauling their marketing strategy -- adds value to their enterprises. You deserve your cut of that value.

Even if you're not in business, don't be afraid to ask for money. Get in touch with that long lost rich cousin. Write a letter to Bill Gates. Beg on the streets if you have to, but get that cheese.

Good luck!

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