In Death of a Salesman, how is Willy's killing himself for the insurance money symptomatic of the way he has lived?

Good question, but I'm don't think that his suicide is
symptomatic of the way he has lived.  But it does represent his continuing belief in the
American dream.

Willy and his brother Ben represent two
ways of being successful.  Willy chose to work hard in one organization.  He puts in
thirty-five years, expecting to be rewardid with a good salary and the respect of his
colleagues.  Ben is the opportunist.  He makes quick money.  He comes out of the jungle
a rich man.  In many ways, Willy wants Biff to follow Ben's example.  All Biff needs is
a stake, and he can make it big.  This is why he presses Biff to go to his former boss
to help set him up in the Loman brothers sporting goods
enterprise.

Willy himself always regretted not going with
Ben to Alaska when he had the opportunity.  In his final scene, Willy imagines that he
is talking with Ben.  He sees his suicide as a business deal, a proposition, that will
have an excellent return: "twenty thousand dollars on the barrelhead." With this
insurance money, Biff, Willy believes, will make it
big.

Willy's suicide is a gamble, a proposition, an
enterprise, much like Ben's venture in the diamond mines. And the venture he did not
take to Alaska.   It does not represent the way he had lived, but the way he wished he
had lived.