The Journey

Getting Health Insurance as a Freelancer

  • The Individual Mandate is no longer in effect as of 2019
  • Clicking the sponsored health care links on Google is bad
  • Individual health insurance that protects your wealth is inexpensive

Disclaimer: This author claims no special experience or knowledge of health insurance, other than the experience of losing corporate provided health insurance and having to buy new insurance (and screwing up a little along the way).

When you talk to someone who likes the idea of leaving their corporate job, two times out of three the person will use health insurance as the reason they can’t do it. When I did it this year, I’ll admit that I was worried about it myself, and back in 2015 when I took some time off, I paid around $300 a month for Affordable Care Act (ACA) qualifying health insurance that basically did nothing for me beyond wealth protection in the case of a really big bill. And it also let me avoid the individual mandate penalty on 2015 taxes.

Fast forward to June 1st, 2019, the first date I would lose corporate coverage, I was prepared to eat the $300 (or more) per month once again. Since I was losing coverage, I went on to try to apply during the enrollment off season. First, I wasted a lot of time by answering questions that could lead to discounts (they won’t for any remotely comfortable income, even if earned earlier in the year). Then, over a period of five days, the site was down and couldn’t even process my application. I thought I might have to eat one month of COBRA insurance for over $600 from my last job. Then I realized that the individual mandate is gone, at least at the federal level.

This is due to the Tax Cuts and Jobs act that was passed in December 2017 and eliminated the individual mandate penalty, effective January 1, 2019. It’d be a good idea to search for any law particular to your state, but nothing stood out as too powerful to me. It’s gone.

I have nothing to say about policy, or whether this is good or bad for the country, but I won’t buy expensive health insurance as a freelancer right after losing most of my income, especially when the site to do it isn’t even working.

After realizing I could just buy insurance from anyone, I got in a hurry and searched Google for “buying health insurance online.” Thinking that the top site was some kind of Kayak-like engine for comparison shopping health insurance, it clicked it. Do not do this. I will not write down the link out of fear that I will help these sites’ rankings, but I will show you a picture of what not to click:

The first website actually looked quite clean and professional, and made it easy for me to answer the few, very reasonable questions. I clicked submit.

Within, and I’m not kidding, 5 seconds, my phone started to ring. That’s when I knew I screwed up. Over the next three weeks, I got hundreds of phone calls and dozens of voicemails and emails. Telling them to stop doesn’t work:

It was pretty bad, but in the end it was only digital communications and not impossible to ignore (if you physically turned a few things off). Still, don’t do it.

In the end, I went to a website of a name I’ve seen before, United Health One, who’s offering non-ACA compliant “short-term” insurance. At first I didn’t understand what that meant, but when you’re buying the insurance you can specify different term lengths, and that seems to be about it. These policies are not ACA-compliant because they do almost nothing for you unless you’re out a lot of money (explaining the term “junk insurance”). But that’s okay for me.

What I really want is wealth protection in case something really bad happens and I owe a hospital $700,000, and thus I went for the highest maximum benefit of $2,000,000. The deductible situation is a little complicated because there are two of them. Under the first one the company will not pay anything, and in the sweet middle ground between the first deductible and second, they will pay some. I wasn’t that interested in that middle spot so I minimized the benefits there.

The UnitedHealthOne website ( almost felt like one of those old school restaurants that offered so many million menu items by sheer combinatorics of the options, which I didn’t like so much. And it annoyed me a little bit that the company name changed from UnitedHealthOne to “Golden Rule” when it was time to buy the policy. But it was relatively easy to make the final purchase, I felt I got what I needed, and it was under $100 a month.

I’ll repeat the disclaimer: I have no idea what I’m doing. Maybe I do rack up $700,000 of medical expenses and then $400,000 of those expenses are denied by “Golden Rule.” Who knows? But I do know one thing: if you don’t click on one of those links I showed you, you can buy health insurance at a very reasonable rate without getting attacked by vultures. Sometimes, that’s all you can ask for.

The Journey

Ogorek Data Sciences has an EIN

Most of the times, things are harder than they look, especially when those things involve the IRS. But I am pleasantly surprised and happy to say, getting an Employer Identification Number from was amazing easy. has a nice page linking you to the online form, and after filling out the questions, you get the EIN in an instant. You can use the number immediately for most purposes (e.g., opening a bank account). For certain tax purposes, you’ll have to wait about two weeks. But not bad.

Why get an EIN as a sole proprietor?

Let’s be honest, I use the name “Ogorek Data Sciences” in blog post titles mostly in tongue-in-cheek fashion. This EIN is, for the foreseeable future, the Employer Identification Number of Ben Ogorek, the employer of himself. Furthermore, this sole proprietor has a Social Security Number that would work just fine for tax purposes. So why bother with it?

On the other hand, if I’m getting the boat-loads of 1099-MISC forms that I’m expecting in the near future, that’s a lot of Ben Ogorek-SSNs floating around on paper documents in the world. I’d rather replace those with the EIN. And, although I’m not in need of the “corporate veil” necessary for an LLC, it’s nice to practice treating the business as a separate entity with its own tax Id.

Cross it off the list!

The Journey

WordPress theme changed to Enigma

I’ll never forget the response to the first “business website” I made. It was around 2009 and, fresh off an inspiration high from the 4-Hour Workweek, I cobbled together a comical-looking effort to siphon money out of the global economy. Despite not knowing anything about web technologies, I decided to build the website with and the free Microsoft development tools. In retrospect, I’m surprised I even got the site to work.

While WordPress surely existed back then, I didn’t know about it. Now, during my second at attempt at my own business, not only is the plan to actually create value, but to buy into trusted framework. I’ve been really impressed with how easy it is to get WordPress up and running, how cheaply it is to host, and how much it can look like a modern professionally-designed custom Website.

This morning, looked like this:

After switching to the Enigma theme and doing just a bit of customization, the site looks like this:

I’m no marketer; some of the one-liners are a little goofy. But it’s a step in the right direction!

The Journey

Applying for a DBA in Wisconsin

One of the choices I had to make as a data science freelancer was whether or not to register as a single-member LLC or proceed as a sole proprietor. A lot of people told me I should get the LLC for tax reasons, for example, to pay yourself a smaller income and take the remainder of the profits as a corporate distribution with a lower tax rates. However, all my research brought me to the conclusion that the type of LLC I’d be applying for, the single-member LLC, is a “pass-though entity,” and all of the income would pass through to my own personal income anyway.

Now the limited liability feature of the LLC is real, provided I’d be able to maintain a “corporate veil,” which I wasn’t sure I was ready to do at this early stage. In July, I’m thinking about forwarding my personal mail to my business address, for instance. So much for separation.

Since I still wanted the experience of creating a business that was not just my given name, I decided to go the DBA route. The DBA acronym stands for “Doing Business As” and allows a sole proprietor like me to create a legal business sounding name without the fees and hassle of an LLC. The DBA is necessary for opening bank accounts in that name as well (apparently you could get in trouble for using a business name that was not registered).

Applying for the DBA wasn’t hard, but like most things government related, you just have to know what to do. LegalZoom will charge you one hundred and change to take the guess work out of it, but if you just go to your state’s process, the instructions are usually pretty simple. In Wisconsin, you file a “Registration of Firm Name” with the county’s Register of Deeds. The instructions are pretty simple.

A week and a half ago, I sent in my notarized application requesting “Ogorek Data Sciences” as my sole proprietorship’s official along with the $30 dollar fee. The name’s not Don Draper grade, but I struggle with names and I asked myself, “do you want to waste time thinking of an awesome name, or do you want to get started?” And while I’ve always thought my last name came across as weird to people, a friend who makes fun of everything didn’t really laugh at the name, and another one commented that it’s pretty easy to say once you know how to say it. It’s pretty close to the sound of the name of the Oreck XL vacuum cleaner. Done.

About five days later, I got my same application back from the Register of Deeds but with the recording area stamped, showing that my payment was accepted. At first I asked, “is this it?” After some reading I found it can take a little longer than a couple days, and I take the returned application as a confirmation that my money is good at the Register of Deeds and my application has been sent to the next level. Godspeed.

Update: There was no “next level.” That was it. The Register of Deeds just recorded the firm name (I believe without any searching or anything.) This caused me some confusion when trying to use the form to get a business bank account with a DBA.