Yes, sturdy boots / shoes do make it much easier. Flip flops hurt. Here's what works for me. Your results may vary (for those who think these ideas suck). Since the bike will move back a bit during this process, the front wheel should be straight. At first the idea of pushing down on the stand made the process really hard. Much easier for me is to hold the left grip in my left hand, push the stand down and insure that both feet of the stand are on the ground. Grip the passenger grip with my right hand. Then, I do DO NOT simply push the stand down, I stand on it with my right foot putting all my weight on it by taking my left foot off the ground. At the same time, I pull smoothly and hard on the passenger grip with my right hand. Note that when both feet of the stand are firmly on the ground, there is no tendency for the bike to tip over. Keeping the body close to the bike is important. From the bikes centerline, I face about the 2 o'clock position which puts my right shoulder almost above the passenger grip and allows me a direct upward pull with my right hand and arm. My foot on the stand is facing about 2-3:00, just a bit forward. Others probably like the foot facing more to the rear. My leg is actually providing most of the lifting power, not arm muscle. Standing a bit to the side and trying to push down on the stand is not going to work well. At the age of 71, I'm no muscle man but find that this technique works very well with no real strain. Pretty much the same technique as all the others but with some personal variations.