Selling Insurance – An Ultimate Guide on Getting Started

How to Build a Profitable Side or Full-Time Hustle Selling Insurance.

Three years ago, I quit my well-paying job at a Berkshire Hathaway insurance company.

A few things led me to this event: first, the traditional corporation culture was killing me; second, I was thinking about a having a second kid and wanted to spend more time with family; and third, I was ready for my next entrepreneurial challenge.

After taking two years off to raise some tiny kidlets, it was time to get back in the game. 

What was I going to do? 

Most traditional jobs still look down on extended family leave (whether they admit it or not) and after making good money at my last gig, I didn’t feel like starting over again. On top of that, I was not ready to go back to traditional work hours – but I did want to work hard, make money and feel proud of what I was doing.

That’s when sales came to my attention – specifically for me, Medicare Insurance Sales. I had worked in finance and insurance before, so I was aware of the profession. However, I had not considered it for me, until I started talking with some friends that were in the industry. They mentioned it was something I could get into even part-time. After doing some research, I got excited about this finance niche as my next side hustle.

Why Sales?

Sometimes, true-blue sales positions get a bad wrap, and this especially goes for insurance sales. In fact, I think one of my first introductions to the profession was in Bill Murray’s Groundhog Day. Murray’s character encounters “Ned” the life insurance salesman whom he tries to avoid in all but one of the cycles of his ever repeating day.

While making fun of the life insurance salesperson did make for pretty good comedy in Groundhog Day, it certainly shows how society can negatively view sales.

I recently read about LinkedIn’s efforts to improve how salespeople are seen in their campaign “The Real Face of Sales.” LinkedIn says their campaign wants to debunk misconceptions about sales. They say,

“Real Sales is about generating personal bonds with clients, solving problems and providing personalized value.”

I couldn’t agree more. Sales is important, and insurance sales is even more important now than ever.

Why Sell Insurance?

Selling Insurance is lucrative, has a low start-up cost, provides entrepreneurial freedom, and produces passive income. However, it does take hustle! In addition, the industry needs younger agents to replace the retiring ones, and there big online marketing opportunity as client demographics change.

The Agent Demographic Problem (Alternative title, “Your Country Needs You!”)

If you are a Gen X’er, Millennial or even Generation Z, your country needs you. Insurance sales is an aging profession, and we are losing agents to retirement faster than we can replace them.

Aging Agents

The average age of an insurance agent is just shy of 60, and the need for agents is growing. According to ThinkAdvisor, at the rate agents are retiring, the industry will need 60,000 new agents every year for the next ten years to maintain numbers. 

Moreover, the profession needs growth, not just maintenance. The Bureau of Labor Statistics describes insurance sales as a faster than average (at +10%) growth profession that needs to add an additional 48,300 agents over the next ten years. 

Retiring Boomers

This need for insurance agents is especially dire in the health insurance industry. 

Just think about who is retiring now… the Baby Boomers. 

10,000 Baby Boomers hit Medicare age (65) each day. The first Boomers (born 1946-1964) started reaching retirement age in 2011 and will continue to retire in droves until 2030. 

Many media outlets have dubbed this the “Silver Tsunami,” which brings unique challenges to our society, but also exciting ways to make money.

Selling Insurance as a Side Hustle Opportunity

Moreover, more and more people need insurance agents, especially in life and health where insurance products have become more complex. They are now used for a variety of different solutions, and insurance agents are increasingly helpful for consumers in decoding insurance products.

As a result, there is opportunity to make money here, even as a side hustle. Even more, as the industry tries to catch up with advances in technology use, agents can begin to work smarter and reach more people in less time.

The younger Baby Boomer are pretty good with technology. They are finding more information for all types of insurance online and are even buying insurance online. Conversely, most insurance agents (especially in Medicare) sell in the old school ways and either don’t need to or want to change. 

The average 60-year-old agent has a good book of business and doesn’t need to rewrite their playbook. The result is more opportunity for younger agents to swoop in and meet the online needs of the changing demographics. 

How to Build an Insurance Business

How to Reach Your Sales Goals This Year

When starting an insurance sales side hustle, you must start by deciding why you want to pursue it and what kind of insurance you want to sell. Then, set your goals and plans to reach them. The next step is to get out there and start selling, so that eventually, you will start to produce passive income.

Step 1: Find Your “Why” and “What”

Selling insurance is a long-term commitment. It is not something that makes you rich overnight, so you need to like it. Moreover, you need to ask yourself why you want to do it. Your why will also help you decide what kind of insurance sales would be a good fit for you. 

To Whom Will You Be Selling Insurance?

Picking your customers is a huge part of selling insurance. Moreover, it is often the main reason why you will want to continue in your insurance business or quit before you even begin to see results.

If you like your target customer group, identify with their needs and desires, and feel satisfied by helping them, then you will want to stick with it. It is so important then that you set-up your business to work with people you like. People that keep you energized instead of bringing you down. People that make you smile or laugh and that you are genuinely interested in.

What Insurance to Sell

niche down to bring sales up

There are many kinds of insurance to sell. What type you choose really depends what group of customers you like to work with. 

  • Do you like working with older folks? Try Final Expense or Medicare
  • Or would you rather work with younger people? Try Life Insurance (there are lots of different was to niche down here too)
  • Everyone needs P&C insurance (home, auto) if you like working with people across the board.
  • If you like working with businesses and entrepreneurs, Commercial Insurance might be your happy place. 

Previously, I sold life insurance to young couples, and then for 2 years I sold workers comp to small businesses.  However, when I started to investigate my “why,” I discovered Medicare Sales happens to be the best fit for me.  

Finding My “Why”?

When I took some time to decide what would work best for my own work habits and life goals, here are the needs I came up with:

  1. Project Focused: I work best with projects and having a time where I work very hard with an end date in mind.
  2. Flexible: I need a job that is flexible with my full-time “being a parent” job.
  3. People Oriented: I enjoy working with people and helping people.
  4. Entrepreneurial: I must be able to flex my entrepreneurship skills. (Before finance, I owned 2 yoga studios and an international wellness licensing company). 
  5. Passive Income Generating: I also need a job that aligns with my early retirement, heavy savings goals.

Put all of that together and I got – Medicare Insurance Sales.

Here is how Medicare insurance sales as a side hustle meets each of these needs for me:

  1. Project Focused: I sell both Medicare Supplements and Medicare Advantage Plans. However, I only work “full-time” for 8 weeks a year during Medicare Advantage’s Annual Enrollment Period each fall. 
  2. Flexible: Outside of my 8-week busy time, I can do scattered appointments or phone calls when I want to work. 
  3. People Oriented: I have a mentor that I work with. He is not my boss but is considered my “upline.” As a seasoned agent, he helps me out and gives me the connections I need with insurance companies in exchange for an override on what I sell. The carriers pay him, and it does not affect my commissions, so it is a great deal for both of us. In addition, the clients are great too!
  4. Entrepreneurial: Insurance sales scratches the entrepreneurial itch that us side hustlers tend to have. It’s a dynamic industry that keeps you on your toes and rewards innovation as much as it rewards persistence. 
  5. Passive Income Generating: Here is where Insurance Sales, and especially Medicare Sales, seals the deal. Initial sales are great, and you get fairly compensated for your efforts, but residuals are the key to income generation. As an example, in Medicare, after the initial sale year, insurance companies will pay you monthly residuals. They often pay these on each active policy for 7 years or even for life (of the policy). Good agents keep their clients on the books easily and can quickly generate 6 figure passive income.

A Sales Job That doesn’t feel so “Salesy” 

sales tips for insurance agents

Out of the various forms of insurance I have sold, Medicare sales most appeals to me because it feels more like an educational process than a sales job. The people you talk to need Medicare, and the insurance plans that supplement the government’s program add necessary value to their lives.

I’m more of an educator than a seller, so this works great for me. However, agents are needed in every market, and the other insurance products can also feel not “salesy” to a good agent with their clients’ best in mind.

Independent vs. Captive Agent

There are two kinds of insurance agents, captive agents and independent agents. Captive agents work for one insurance carrier and are sometimes even employees of this company. They must sell their company first.

Independent agents are more entrepreneurial types that pick which carriers they want to sell for and can represent many companies at one time.

Being an independent agent can take the pressure off of having to push just one plan or one product. For example, in the Medicare insurance industry, the U.S. is seeing a rise in popularity of Medicare Advantage (MA) programs. These are good plans for many people, but having more plan options can make the decision process more confusing for seniors.

Independent agents that represent both Medicare Advantage Plans as well as Medicare Supplement (Medigap) Plans can show seniors the benefits and drawbacks of both ways to set-up Medicare without pushing a particular plan or carrier. Which again leads to more educating and less selling.  (If you are unfamiliar with the Medicare health care program and how it works, you can read more about it here.)

Don’t get me wrong, captive agents can be great agents too. There is a need for both, and you need to discover what is best for your situation. I am only saying, there is an important distinction between selling and educating, and being independent helps you to do both, easier.

Being independent is just another way to not make insurance feel less like a high-pressure sales job.

Room for Growth

Finally, if you desire, insurance sales gives you a great platform for expanding your business into other forms of financial products later. Just like insurance, financial products also require you to be a good listener with a passion for matching the right clients to the right products.

Step 2: Set Your Goals & Plan

This business has a start-up year where you might not make that much money initially, but then it picks up with residual commissions after year one. That is one reason why it sometimes needs to start out as a side hustle. After year one, you can set your sights on full-time selling or keep it part-time. 

I’ll get to the revenue details in a minute, but first let’s look at the costs to get started.

Start-Up Costs

As I mentioned, insurance sales has a pretty low start-up cost. You don’t need expensive equipment or even an office (as you can meet with clients in their homes or even over the phone).

What you do need are a state licenses where you want to sell, Errors and Omissions (E&O) Insurance, business cards, a website, and training/licensing materials and tests for the products you want to sell. I spend well under a thousand dollars on all this each year.

Finding Your Support System

Yes, you can go at this all alone, but it is much easier with a support system. It will help you get off the ground faster, and it will keep you going when you want to quit.

When I first started selling insurance, I went with a very formal support structure and joined a large Insurance Group. I was “independent” but was trained and supported on one particular insurance brand that I lead with. This can be great if you meld quickly with the culture of the local office, but I didn’t really find my groove here. So, after a test run, I quit working with this group.

It wasn’t until 2 kids and a stint with a corporate job later, that I figured out where I suppose to be. Moreover, discovering what kind of support I needed.

Now, I work as an independent agent, with a small insurance agency that specializes in Medicare as my support system. I have an “upline” mentor that helps me sell and even helps me set appointments, all for an override on my business. This works out great for me because I am still completely independent, but I have someone to call when I need help or need encouragement.

You need to find out how much support and flexibility you need. From corporate to “mom-and-pop” there is a support system for everyone.

Contracts and IMO’s

As an independent insurance agent you will need to decide what carriers you want to represent and then get contracted and trained with them. This is tricky to do all on your own. So you will need to find an “Insurance Marketing Organization” (IMO) to help you get contracted and hold your contracts for you.

I found an IMO that happened to be headquartered right here in my hometown of Omaha – Senior Market Sales. They were very helpful in directing me to what carriers were appropriate for my location and market. They also were the ones that introduced me to my upline and mentor.


Once you are contracted with a carrier, you will need to be trained on their products. This is especially true for Medicare Advantage sales where you need to take a Federal training and pass a test each year to be able to sell this line. On top of that, Medicare Advantage and Part D drug plan sales require you to test on individual products with each carrier before you can sell them.

Training is huge for all types of insurance, and it goes beyond just initial product training. In order to be good at selling insurance, you need to fully understand the various products and how they can all be used to add value to your customers lives. Therefore, you must be the kind of person that doesn’t hate training and learning. It doesn’t have to be your favorite thing, but if it is, then you will have a leg up on every other agent.

Writing my blog has been one of the best things I could have done to fully understand the products I sell. Moreover, it has helped me in getting more sales! I can’t tell you how many times people ask for my cards to give to all their friends at the end of an appointment. When they do this they tell me that was the best explanation of Medicare and Medicare Advantage they have ever heard and all their friends and family need to hear it too.

Fully training on and understanding the products will help you to be more helpful to your clients and more creative with your solutions for them.

Related Reading: Read this article to learn all the details on how to get licensed, trained and started in insurance sales.

Step 3: Getting Out There

Marketing & Leads

After you are contracted, trained, networked and ready to go, it is time to get out there!

Another cost associated with insurance is sales leads and marketing. This is a place where it is very smart to have help. When I first started out, I did not have any help besides a few people at my insurance marketing organization (IMO) that I could call sporadically with questions. It was difficult to navigate the industry, especially industry marketing, by myself. I didn’t get very far until I connected with an experienced agent as an “upline” and mentor.  

There are many organizations that will help you (or charge you) for leads, and some of them are very good. In addition, the insurance carriers will also throw in some money and leads depending on what kinds of insurance you are selling. These opportunities are also much easier to secure when you work with someone experienced. 

Of course, the hard work/low-cost avenues available to all sales professionals (networking, speaking, canvasing) are always there too. Referrals are the best form of marketing you will have, but those take time to build-up. Many agents use lead sources while they are in building mode. I have too. Market to market, results with these are very different, and it makes sense to research your area of the country first before sinking a lot of money into leads. 

Agent Marketing Newsletter

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New Marketing Avenues

Insurance buying habits are changing as all generations become more tech savvy. As an example, in the past, Medicare beneficiaries have been the pen and paper type. However, the Baby Boomers are changing that. Online Medicare sales and information is taking off. Insurance companies are not known for being on the cutting edge of technology, but every year they roll out new ways to market and new ways to enroll customers online. 

There is an opportunity for people that are comfortable with online marketing to build a solid Medicare online brand. That is what I am doing on my website I am currently working on both local and national SEO, so that as more Boomers (and eventually Gen-Xers) turn to the internet for Medicare answers I am right there for them.

Medicare’s Unique Annual Enrollment Period

As I write this article, I am just starting the beginning of my busy season. The Medicare Advantage plans I sell have a limited enrollment period of just 8 weeks a year. During this period, I will be leading seminars, sitting at drug stores answering questions, and going to individual appointments with potential clients. I work full-time during this season alone and make most of my sales for the year.

Even just working full-time for 8 weeks a year, you can make 30-50k. If you did this each year, by year three you would be over $100,000 including your residuals. Not bad for a side hustle. Which brings me to step four. 

Step 4: Produce Passive Income

This article is about selling insurance as an independent agent – not a captive agent or an employee of an insurance company. There are insurance agent jobs where you get a salary and maybe a commission or bonus on top of that, but I am talking about a pure commission position. The entrepreneurial side of insurance and sales. 

In this role, I am my own boss, but I only get paid when I sell. The upside to this is my commissions are significantly higher than if I were to be an employee. 

You get paid a little differently with each insurance product. However, commissions in my niche of Medicare are regulated by the government, so there is not a lot of difference between insurance companies. After the first year’s commission, with most products, you will get a monthly residual commission for every policy you have active on the books. In my Medicare niche, even with a $20 a month residual (just as an average example), these numbers add up quickly, as year to year you add more people on.

Selling Insurance as a F.I.R.E. Strategy

Are you on FIRE (Financial Independence Retire Early)? Are you trying to retire early? It sounds like a great idea.

People who are on the “FIRE” path decide to save a very large part of their earnings so that they can retire early. As a result, they live off of much less than most people might be comfortable with. They see it as an adventure. You could practice a less extreme savings plan and adjust your goals to your needs, but FIRE is a captivating idea.

As an exercise, let’s look at how you could use Insurance Sales as a F.I.R.E. strategy to retire early. Meaning, how could you reach financial independence using this profession. 

Here are our assumptions:

  • Let’s assume, you want to do Medicare Insurance Sales as a side-hustle in year one and then full-time Medicare sales after that as your sole way to generate money.
  • You have a goal of actively working until you save about $1 million dollars.
  • We will also assume that not everyone you sell to is renewing each year, and just to make it easy, we will say we lose 20% of our clients from renewals yearly. 
  • Next, let’s assume you can live off 40,000 a year (before taxes) and are saving the rest. (You will have to get a second job in year one to account for the first year often being the hardest to get started). 
  • We have you working until year 8 actively selling, and then switching to only maintaining current clients after that, but still getting your residuals. People will continue to fall off the books after about 7 years being with you, so we have the commissions coming in until the last people leave in about year 16.
  • 50,000 a year is a conservative sales goal for an agent that knows what they are doing, so you could make a lot more each year and cut your saving time significantly.
  • Finally, our numbers leave out initial MAPD plan sales having a high commission in year one for the sake of simplicity, so you could pull in more year one cash if that type of plan is your focus.  
  • And a Disclaimer – this is only a general, roughed out example of how some agents make their money and should not be considered a guarantee for any reason.

Selling Insurance Agent Earnings, Commissions, and F.I.R.E. Savings Goals (Extreme Saving Plan for Early Retirement)

YearInitial SalesRenewalsYear Total$ to put in Savings
In year 8 –  live off 4%, 40k+, In year 16 – live off of 4% of total saved, 93k

For the sake of simplicity, we just assumed you were sticking your money is a savings account and not investing it (but we know you would not do that…) until year 8, where you can stop selling and just live off of the 40K+ in interest you were generating off your million dollar savings.  In year 16, 4% of your savings is at 93k (but again it would be much higher if you were investing in the stock market). 

This is all of course, just a fun exercise for most people, but it gives you an idea of how commissions and renewals can propel an insurance sales career.

Is Selling Insurance for You?

There is money to be made in the non-glamorous niches like insurance and Medicare. Apparently, Millennials are not flocking to insurance sales, but there is big opportunity in this industry, even as a side hustle.

If you are an entrepreneur with more of an educational bend than a sales bend, and think you could like working with what is probably your parents generation, then give selling insurance a shot!

I would love it if you would reach out to me directly with any questions or thoughts. Please join our newsletter and leave a comment below!

Related Reading

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About the Author

Carly Cummings. Carly is a an “Elder Millennial” on the path to early retirement with the help of two strategic passive incomes. She is a licensed insurance agent and former FINRA licensed financial advisor. Carly is the Creator of where she helps her readers (of all ages) find the best health care and create the best cash flow in retirement. 

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