My Experience Buying Dental & Health Insurance For A Self Employed Professional

by JS 

self-employed insuranceWe all know that there are many benefits to becoming a self-employed professional. At the same time, though, there are some added complexities that come along with the territory. One of the most time-consuming and perplexing ones is the process for buying health and dental insurance. Most of you have probably always relied on your employer to provide you with coverage. If you were asked, do you know the first thing about buying an individual insurance policy?

For the first few years of my “self-employed life,” I purchased individual health and dental insurance through Aetna. Early this year, though, I was finally fed up with their premium increases and decided it was time to do some research.

During my time shopping for and buying insurance, I learned quite a bit about the process. Even though it sounds complicated and intimidating, there are several steps you can take to ease the pain and lower your overall level of stress:

1. Use the Internet, but don’t rely on it. Much like the majority of consumers, I started my search for health and dental insurance online. Soon enough, I was inundated with quotes and related information. While I was off to a great start in terms of the information I was collecting, there was a big problem: I did not fully understand what I was looking at.

I realized that while the Internet was a good place to gather basic information, I need to get some personalized attention before making a purchasing decision. This led me to call three companies and speak one-on-one with qualified representatives. They were able to explain what plans worked for my personal situation and needs. After these conversation, it was much easier for me to compare options and make an informed decision.

2. Do you have “health insurance stores” close to home? A few years ago nobody would have ever believed that you could walk into a store and purchase health insurance. Fortunately, this has become a reality. In Pennsylvania, for example, there are Highmark Direct stores in many of the largest cities and towns. As you can imagine, I took full advantage of this opportunity.

Tthere are many benefits of buying in person at a store including the ability to communicate face to face with a qualified agent, being able to chat with a live person who can help with the application process, and the chance to ask questions about each and every policy.

At my meeting, the representative explained which policies were best for self-employed professionals, as well as how they differed from one another. Soon enough, it was clear that buying from Highmark was the way to go for me. It wasn’t just the store that swayed me (this did help, though); it was the personal service, variety of policies, and reasonable pricing structure.

3. Consider buying from a company that offers both health and dental insurance. With Aetna, I was able to do this for approximately three years. It was nice being able to pay one premium for both types of coverage. Not only did this make things simple for me, but buying both policies also led to a discount. Unfortunately, my new provider does not offer dental coverage. For this reason, I have to deal with two payments every month. After examining the costs, I found that I was still better off financially in the long run.

Final Thoughts
On the surface, it can be difficult to make the leap to self-employment as you worry about how you are going to get the proper level of insurance without spending too much. While you will have to pay for your own policy, which may have been virtually free before, there are some hidden benefits; in addition to having more choices and greater freedom in what you buy, health and dental insurance premiums are also tax deductible.

If you are self-employed or thinking about going this route,the tips above should help you when it comes time to purchase health and dental insurance. Have you had to deal with buying individual health or dental insurance? I would love to hear about your experience and any tips you might have!

(photo credit: cote)

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4 Responses to “My Experience Buying Dental & Health Insurance For A Self Employed Professional”

  1. Sam P on April 12th, 2011 12:50 pm

    This is a great post JS. One thing to consider is that if you look for quotes online and fill out a form, a lot of times representatives will call you directly and you will not have to reach out to them.

  2. Ann@DentalImplants on July 28th, 2011 6:02 pm

    I always doubted getting dental health insurance as someone who is self-employed. I don’t know if I could find a good deal considering that I may be charged for something bigger. Also, I’m afraid I might not afford it. I know it’s valuable and would be of good use.

  3. Daniel Singer on October 25th, 2012 6:14 am


    As a genuinely honest and caring insurance agent, while your points to not exclusively depend on the Internet and service are very much implemented in my own insurance practice, I have concerns about the “Health Insurance Stores” you bring up. Are these insurance companies? Are they part of a drug store? Are there licensed insurance agents servicing you, or are the representatives licensed to sell insurance?

    Judging from the date of this article, this looks to be over a year ago. Do you still have the plan? Did the folks from the “highmark” store tell you that on the Aetna dental plan, that it only covers cleanings and checkups? Anything more extensive is out of pocket? Based on your article you seem to have the right benefits for your needs.

    I would further add, as an honest agent who will more often than not make sure that his clients are OK LONG after the sale, that you have assurances from this “highmark” store that you will get the support you need if you have billing issues. I am also assuming these guys were up front with you in terms of determining whether or not you had any conditions to be concerned about.

    While I appreciate you sharing experiences with others, I would caution you that not everyone may have “highmark” or any type of health insurance store closest to them: they may need to go through agents. I am well aware of the less than savory reputation of some of my colleagues. But I would add that if you can find an honest agent that will, much as the Highmark people did, listen to you and work with you to propose plans that meet your needs and budget, that self employed individuals and others take the opportunity to meet with a licensed insurance agent.

    I appreciate you sharing your info: especially with all the talk regarding health care reform, people are more confused than before.


  4. Tyson on October 19th, 2017 3:41 pm

    Thanks, JS!

    One thing to think about is that when looking for quotes and filling forms online, a lot of times representatives will call you directly and you don’t have to reach out to them.

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