Holiday Shopping for an Entrepreneur? Follow These Do's and Don'ts Don't waste your money or effort on gifts that will only frustrate your entrepreneur.

Living with an entrepreneur isn't easy. We work nights and weekends, don't have much time for hobbies and have probably already bought the newest gadget ("I needed it for work!"). During the holiday season, these quirks become particularly challenging.

Here are five do's and don'ts to keep in mind when you're planning holiday gifts for the entrepreneur in your life.

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Do give your entrepreneur:

Gifts that respect his or her time. If your entrepreneur is a voracious reader, buying him books or magazine subscriptions is a great idea. But if he hasn't cracked a volume in months, it's unlikely to happen now. Don't waste your money with wishful thinking. Instead, adapt to his circumstances and buy him a gift certificate for audiobooks, so he can listen on his drive to work or while he's working out.

Gifts that show you're paying attention. There are some gifts that everyone likes -- no one is going to turn down an iTunes gift card. But it's also unlikely that receiving it will make her feel incredibly special and understood. If you want to give a meaningful present, listen hard to what she's been telling you over the past year. What topics is she passionate about? Who does she admire? What issues is she struggling with? What are her greatest hopes? Give personal gifts that show you've been paying attention. That's a winning formula for anyone, but it especially matters to entrepreneurs, who often face skeptics in their professional lives and need to know the people closest to them believe in them.

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Don't give your entrepreneur:

Anything that requires assembly. Disregard this if the entrepreneur in your life is an engineer who loves tinkering. But for the rest of us, assembling anything – whether it's IKEA furniture or a new bike – just isn't worth the opportunity cost. You don't want them gritting their teeth as they "thank you" for a gift that wastes hours of their time. If it requires assembly, skip it -- or hire a TaskRabbit to put it together for you.

Anything that involves technology. Unless your entrepreneur has asked for it, giving tech-related gifts is often a bad idea. First, they can usually write off any tech tool they want by buying it through their business, so it's far more economically efficient for you to give them other kinds of gifts. But unless you have specialized knowledge, it's easy to pick the wrong model or foist something they don't want onto them. In the past, I've received lovely, expensive, and unwanted gifts, including a portable DVD player (which I eventually insisted my mother return, because I literally was never going to use it), and a laptop that forced me to switch platforms and cost me hundreds of dollars for new software and several days' lost productivity.

Gifts for the person you wish they'd become. Maybe you'd like your entrepreneur to spend more time at home cooking with you. If she's expressed interest in the idea, fantastic: a cooking class, cookbook, or collection of high-end kitchen supplies might be just the ticket. But if that's your wish, not hers, your gift is likely to come across as passive aggressive and hurtful. Think about things they're interested in and have spoken to you about. Ask yourself: Is this gift likely to make them feel guilty? Anything related to exercise and weight loss, unless they've requested it, is especially risky.

Holidays and the gifts that accompany them, can be incredibly meaningful -- or incredibly disappointing. Don't waste your money or effort on gifts that will only frustrate your entrepreneur. Following these do's and don'ts will help make sure your holiday is more special for all involved.

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