Social Security: An Essential Read

Posted by David Chester on 3 July 2018

Hello all. It's been a while since I've blogged here. Like most of you, I am freelancing and doing my best to survive. It's not always been easy. 

I've wanted to post this for a long time, and I have a moment now to share this with you, so, here goes: If you are an American citizen working in Japan and you are not contributing to your Social Security, you are making a big mistake. This is what happened to me: 

I came to Tokyo in 1993 and was granted a working visa in 1994. Well, here we are and now it's 2018. In my salad days in the late '90s, I contacted my American tax accountant and asked her if I could contribute to my Social Security even though I was earning Japanese yen. She repeatedly (and incorrectly) told me I could not. Because I had worked with her for years, I believed her. I did ask again several times through the years, and to make a long story short, she finally called the IRS (anonymously) and asked them the same question I had been badgering her with. The answer was: "Yes, he can contribute." 

Because of my naïveté and my faith in my accountant, I lost 20 years of paying into my SS funds. Needless to say that does not make me happy at this point in my life, as I'm not really anticipating working round the clock for the next 20 years to make up for it. Although my accountant apologized, it cannot change the fact of what has happened. What I can do, from this point forward, is pay into my fund. Now that I'm older and not earning that much, I don't know that it will really matter. 

I'm writing this because I have sensed an incredible laissez-faire attitude among many fellow (American) freelancers in Tokyo in regards to contributing to their own Social Security fund. Here are the things I've heard/encountered: They're young or youngish; they won't be here that long; why should they? Who cares? I'll deal with it later. I don't want to think about it now. 


No one likes to think about the fact that we won't live forever. I suppose in the future those that have money will be able to extend their lifespans by decades perhaps, but for working stiffs and the Regular Joe/Jane, that won't be the case. Your "shelf life" as a freelancer will one day come to a screeching halt. Do you have savings you can rely on? Will you have paid into your Social Security funds? 

We can get on an endless argument loop about "The funds won't even be there, so what is the point?" 

You go ahead and have that argument with someone else. What I learned in the most painful way possible is that I should have trusted my gut and gone a step further and questioned more and found out for myself that I could have contributed to my future. I will now be paying for this mistake until my dying day unless my fortunes change. (One must live in hope.)

So, I really don't like others to tell me what to do any more than anyone else does, but it is my fervent hope that the next time you pay your American taxes (and of course, you ARE paying them, aren't you?), you will also make sure you pay into your Social Security. 

This has been a public service announcement from your friendly fellow freelancer.