A comfy chair. Your workaholic friend no doubt spends a lot of time crouched in front a computer. Why not make this an easier, more relaxing experience for him or her? Try the delightful kitsch of a super-comfortable La-Z-Boy for some office furniture that doesn’t take itself too seriously. Put a pin in the seat so they don’t spend too much time staring at screens.
A new calendar. It’s a gift that says “I know you’re busy and acknowledge that you only know how to manage time by scheduling it out in one-hour blocks.” For an added bonus, fill out every date with mandatory time that the recipient has to spend with you — it’s giving yourself a gift at the same time.
Some nice pens. A fine writing instrument can make those back-of-napkin concept sketches pop. And the signatures on all that legal paperwork will absolutely shine as your friend makes the move to sell his or her company!
Sales and client leads. It’s a way of saying “I love you” in a language that they understand.
A cat. This is a bad idea. Do not get your workaholic friend a living thing that depends on his or her having some semblance of spare time to keep another thing alive. Cats are easy to care for, but they’re terrible employees.
An all-expenses-paid vacation. Not only are these expensive as hell, but your friend likely has no idea how to handle unstructured time (hence the calendar suggestion above).
An iTunes App Store gift card. You will never see your friend’s face again, as it will be buried in an iPhone screen, playing with all the cool new apps he or she just downloaded.
A Tempurpedic pillow. Your friend doesn’t sleep enough to get any mileage out of these delightful pillows that form to the shape of your head. It’s like laying on a glove full of lotion, and it will be totally wasted on someone who’s busy agonizing over sales or clients or share prices as they drift off to a mostly restless sleep.
Action items. As if your friend needs more things to do.