The major difference between the two responses is explained very well by Adam Lieberman on Aish.com.

There is a world of difference between what Eisav meant when he said he has "plenty" and Ya'akov declaring that he has "everything." Eisav, a selfish person caring only about his materialistic possessions, proclaimed that "I have plenty" because "plenty" is quantitative. His material possessions are what he saw as his net worth. If he would ever lose a majority of his possessions, then he would be plenty no more.

Ya'akov, however, who had his entire family with him, proudly declared, "I have everything." Our most valuable and prized possessions will always be what money can never buy - our lives, our health, our families. For thousands of years, the wisest men have been preaching this truism. But why do we fail to embrace it?

In interviews with elderly people who look back on a life gone by, they dejectedly speak about how they should have spent more time with their families, taken better care of themselves, and certainly focused less on their careers. In fact, there isn't a headstone that could be found on a single grave site that states that the one buried achieved great success in business, real estate, athletics, or the arts. Rather, it proclaims the virtues that the deceased possessed as a grandparent, parent, sibling or spouse.

And this is the world's most ironic paradox. While society, the media, and the world-at-large shower accolades and praise on those who achieve business or personal success, when you pass away this isn't at all how your life is judged - by man or by Hashem.

Monetary and career success are wonderful things. We're all designed for greatness and should strive to succeed and grow in many aspects of our lives. But it's the priceless things in our lives that we tend to take so much for granted and never fully appreciate until we, G-d forbid, no longer have them or are faced with a fear of losing them.

This is why Ya'akov knew he had everything. Is there not a dying wealthy person who would without hesitation give his entire fortune to live another year? How about for just another week? Would you ever want to switch places with him? Of course not. Yet, billions of people who still have so much physical life in them choose to walk the earth being unhappy, discontented, and miserable.

The reason for this is that they're usually focused on only the same things that Eisav was. Their idea of wealth is exactly what the zombies of society and the media have said that it should be. So instead of appreciating and loving their tremendous and endless amount of true wealth that constantly surrounds them, they instead choose to dwell on missed and lost opportunities, the things they don't have, and all of the possessions they long for.

If you think about "what you have" in the same terms as Eisav, then you are certain to have a life filled with frustration, disappointment, and unhappiness. But if you understand the life-changing statement of what Ya'akov said and you think about all of the irreplaceable and priceless things you have in your life right now, then you now will wake up each and every morning confidently knowing that you really do have everything.

Shema Yisrael Torah Network
info@shemayisrael.com
http://www.shemayisrael.com
Jerusalem, Israel
732-370-3344