Why I Have Mixed Feelings About Getting Life Insurance


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  • When my father died and I received his life insurance, it took me a long time to accept that the money was mine.
  • I finally used it to buy myself an apartment in NYC, which I later sold at a profit.
  • I’ve since built wealth through real estate, but can’t bring myself to buy life insurance of my own just yet.

When my father died about 30 years ago, my sister and I received a major life insurance payout. My sister was still a minor, so my mother oversaw her investing the money with a financial advisor, but I was 19 when he died, which meant I was legally an adult. I was on my own with how to manage it.

It was so overwhelming, and I kept it in cash for several years, along with money I had inherited outright. This was unfortunate, and it took me ages to find a financial advisor.

I used the money to buy real estate all over the US

The first real thing I did with the money was buy an apartment in New York after I graduated from college. This made sense to me: I needed somewhere to live, and the funds were just sitting there. For $500,000 (which felt really expensive at the time) I got a cute two-bedroom in the West Village, with a view of the Empire State Building. 

The moment I signed the papers to buy it, my next call was to 1-800-Mattres (“Leave the last S off for savings!”) and had a bed delivered to the apartment so I could sleep there that night. I was a 23-year-old with an apartment in New York and I appreciated my dad and the money he left me to make that happen.

Four years later, I moved to California and sold the NYC apartment for almost double what I had paid for it. That was very satisfying, of course. I went on to buy and sell residential properties in Los Angeles; Vancouver, Canada; and Naples, Florida, before coming back to New York and settling here. 

My record with real estate hasn’t been perfect: I got caught in the 2008 housing bubble in Florida and I saw my property value go down dramatically on my primary residence. Ouch!  But on the whole, real estate has been a great way to have invested the proceeds from my father’s life insurance policy and inheritance. Property was an investment I understood, and even when the property value went down, I still had somewhere to live, so it didn’t really feel like it mattered. 

I haven’t been able to bring myself to buy my own life insurance

Today, I am a parent myself. I have two great kids who surprise and delight me with their brilliance on the daily. Now that I am a mom, I know that I should probably get a life insurance policy of my own. 

I have a friend whose mother was very thoughtful about the purchase of life insurance, getting a large enough policy so that if, God forbid, something happened to her while my friend was still in school, college would still be paid for. My friend remembers her mother gratefully lowering the policy (and the premium costs that came with it) once my friend had successfully finished her schooling. This just makes so much sense.

And yet, I haven’t brought myself to do it quite yet. Even though I see the benefits of that policy in my life, the experience is still wrapped up in the pain of my father’s death. I got a big whack of money because someone I love died. It just feels … off. It took a lot of emotional work and therapy (which I certainly paid for using some of the proceeds) to help me to accept that the money was mine, to do with as I saw fit.

I guess I could use more therapy to help me do the right thing for my children …

I’m likely afraid that planning for my early death could bring it on. My family has recently been through a tragedy and I just don’t want to think about the possibility of more trauma.

Sometimes people put off writing their will because it means confronting their own mortality. I know that I resisted it until recently. But I learned something interesting from a trusts and estates attorney: Some cultures believe that when you write your will, it’s an omen for long life. I know that I felt a rush of relief when I finally completed a new will in 2020 after putting it off for several years. 

So perhaps life insurance will be the same. For now, my “insurance policy” is aiming to take excellent care of my body, mind, and finances. I have structured things so that if something did happen to me, my children’s education and lifestyle would be OK. But perhaps, just the act of writing this will help me shift my hesitancy around adding a policy to the mix. 

Life insurance was a moving gift from my dad. I think I put it to good use. I am not yet ready to make that kind of gift a possibility for my own children, but I’m open for that to change.

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