Taking photos of your large multi-generational family shouldn’t be so overwhelming that you never do it. Keep it casual, don’t over dress and keep it local. Have a great backyard? Shoot there instead of trekking to a chicago location that will create stress on everyone involved. Have a pool? Beautiful landscaping? A park nearby? The most important thing is keep it simple and loose and have the photographer travel to the most advantageous spot instead of the other way around. I love these family photos from our multi-generation shoot because they are casual, gorgeous, authentic, and not too posey.