Gelf-Care 30-Day Challenge Day 30: Where Are Blaire, Tootie, Natalie & Jo When I Need Them?

“L’chayim!” is what my people (the Jewish side) say when we toast. It translates to “to your health,” which is essentially what this month was all about.

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One of the biggest things on my Gelf-care list (even though I didn’t make an official list) for the month was to get new health insurance. It’s one of the things about adulting that I really hate.

Since I have freelanced for so long, I have to pay for my own insurance and believe me, the options for an individual are not great, so that leaves me with many feelings.

I’m overwhelmed with choices. I think about “what ifs.” I try to find the perfect option for me.

What does that mean?

I spend (read: waste) a lot of time overthinking this decision.

I don’t even want to begin to calculate how much time I spent on this this month. Believe me, it was not decided in a day, but it’s also something you can’t take likely and the systems in place are not exactly easy to navigate.

To be fair, it’s not an easy decision to make. There are lots of factors to consider and yet, I still made myself nuts trying to pick one.

Here are just a few of the steps I took en route to my perfect (nice try, Gelf) health insurance plan.

  • I spoke to someone at the Actor’s Fund and got his rundown (after trading voicemails and emails).

  • I spoke to friends who freelance to see which plans they’re using and researched those.

  • I spoke to a healthcare advisor at the Freelancers Union.

  • I bothered my friend Judith several times with my indecision to get her thoughts (after all, she’s my own personal Buddha.)

  • I called my friend Michael who has a small business to see if I could be put on his plan in exchange for me being doing some work for him.

  • I asked my friend Tammy who runs a non-profit to see if I could barter my services to be put on their plan.

  • I posted a request for doctors, OB-Gyns and dermatologists on Facebook. Then, researched them to see if they took the plans I was considering.

  • Someone brought up One Medical and since I’ve heard good things about them, I called to see which insurance they take.

(I deliberately did a bulleted list instead of a numbered list because I didn’t want to see what sadly is the fraction of steps I took on my quest.)

Unfortunately, a lot of doctors’ websites have outdated insurance information, so you have to call them. When do they close? 5:00 p.m. Not always the most convenient time. I don’t want to even tell you how many doctors’ offices I called because I lost count.

As a Capricorn, I have a lot of patience. I also like to do research, which is helpful in most situations, but not in this one. I surrounded the problem.

I’m not proud to say this, but I was crippled with indecision. That’s why nothing motivates me like a deadline (thank you, New York state for extending it to January 31.)

Finally, I called Emblem Health upon the Freelancers Union’s suggestion. The service rep, Ramon, assured me 100% that my doctor was in the plan. I didn’t believe him. I had looked at her site and called recently, but I wanted to make extra sure before I pulled the trigger. He told me to put him on hold and call my doctor’s office. As I waited for them to pick up, I prayed that I’d get good news. Maybe Ramon was right. Maybe I needed to trust him and people in general more.

The person picked up the phone and told me that they, in fact, did not take that type of insurance, but other Emblem Health types. I hung up, went back to Ramon, in so many words, telling him he was wrong.

So now I was not only distrustful of the sites, but of the plans and the customer service people, too. Oy.

Ramon told me that I needed to talk to a rep in a different division. I told him he needed to suck it (okay, I didn’t, but I was tempted to.) He put me through to the other division and within seconds, I got disconnected.


I had to run to a meeting, so I called back en route and spoke to a much better-informed rep, John. I won’t get into any more details, but needless to say, I wound up making more phone calls the next day, worried myself needlessly and finally pulled the trigger. I didn’t even feel relief. Just frustration that I wasted so much time.

So much for ending Gelf-care month on a high note. :)

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At least I learned something that I knew all along. Something I learned as a kid. You take the good, you take the bad. You take em both and there you have… the facts of life. And nowhere is that more apparent than with health insurance.

The good news is that I’m covered now, I’m grateful I can afford it and there’s no use in saying anything else. After all, I’ve certainly “covered” enough ground on this topic. :)

Are you a decisive person? Do you overthink things? Do you work yourself into a tizzy over the littlest things sometimes? Tell me below and know that you’re not alone.