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6. I’VE LONG INVESTED AGGRESSIVELY, KEEPING 80 PERCENT OR MORE OF MY PORTFOLIO IN STOCK-INDEX FUNDS. Now that I know it’s likely I won’t live more than another year or two, I’m even more
aggressive. Why? I’m no longer investing for my retirement. Instead, I’m investing for my heirs, and their time horizon is far longer than mine. 7. BECAUSE OLD AGE IS NO LONGER IN THE CARDS,
ALL KINDS OF ISSUES ARE OFF THE TABLE. I don’t have to fret over future long-term care costs, or whether to choose original Medicare or Medicare Advantage, or how to minimize my retirement
tax bill. Instead, my top priority is making sure everything is in good shape for my heirs. 8. AS OF MY 62ND BIRTHDAY IN JANUARY OF THIS YEAR, I COULD HAVE APPLIED FOR SOCIAL SECURITY. But I
won’t. My goal is to get Elaine a healthy stream of Social Security benefits. After much research — including a consultation with the developer of opensocialsecurity.com, a free Social
Security strategy calculator — I figured out that in our situation, I should skip claiming. Instead, Elaine will claim survivor benefits based on my earnings record when I die. Once she
turns 70, she’ll swap to a benefit based on her own record. 9. I THOUGHT MY FINANCIAL AFFAIRS WERE WELL ORGANIZED. I WAS KIDDING MYSELF. I’ve spent months shredding old tax returns, ripping
up investment statements and organizing what remains. I fear that if I don’t throw out unneeded paperwork, my family will think it’s important — and I will have bequeathed them unnecessary
confusion. 10. THERE’S ALWAYS MORE TO THROW AWAY. I’ve moved four times since 2011, shedding possessions on each occasion. Yet I keep finding more things to toss or give away. My 13 years of
downsizing have taught me to be ruthless. The fact is, there’s nothing that I’ve unloaded over the past 13 years that I wish I could have back. 11. FOR YEARS, I’VE BEEN CARTING AROUND A BOX
OF OLD MAIL: NOTES FROM OLD GIRLFRIENDS, CHRISTMAS CARDS FROM 1986, LETTERS I GOT WHILE AT COLLEGE. Mixed in there was some really bad poetry I wrote. Did I carefully review everything in
the box? Hardly. I tore up most items after a quick glance and added them to the recycling bin. Am I glad my kids will never see all this stuff? You bet. 12. MY FINANCES WERE PRETTY SIMPLE,
BUT I’VE BEEN SIMPLIFYING THEM EVEN MORE. I’ve closed two of my four credit cards, liquidated a small IRA I inherited from my father, and folded a solo Roth 401(k) into my Roth IRA. All this
is a whole lot easier for me to do now than it will be after my death, when family members will have to produce death certificates and prove they have the authority to act. 13. I’VE ADDED
ELAINE TO MY VARIOUS INSURANCE POLICIES AND MADE HER THE JOINT ACCOUNT HOLDER ON MY TWO CHECKING ACCOUNTS. One of those checking accounts is debited for all utilities — gas, water,
electricity, internet, cellphones — so it’ll be easy for her to take over the household finances. 14. TWO DAYS AFTER I WAS DIAGNOSED WITH CANCER, I SAT DOWN WITH ELAINE AND MY CHILDREN TO
WALK THEM THROUGH MY ESTATE PLAN. I quickly realized one conversation wouldn’t be enough. Stuff that was second nature to a financial nerd like me was baffling to them — things like the
difference between traditional and Roth IRAs and what a “step-up in cost basis” means. Since then, I’ve fielded countless questions from Elaine and my kids.