How I Manage Insurance Payments As a Freelancer

Written by Elizabeth Wellington on October 25, 2017

Insurance payments are challenging to manage even when you work for a traditional employer. But if you’re a freelancer, they’re even more of a hassle. Every independent contractor needs to manage both their personal insurance — health, life, disability, car, house and pet insurance — and business insurance. How do you even begin to keep track of all those bills?

After a couple years of struggling to track payments and responsibilities, I worked out a system that helps me manage my financial obligations. If you’re an indy, consider applying this approach to all your personal finances. Trust me: Investing in a clear process for insurance payments will make your life a lot easier in the long run.

Organize All Your Documents

I recommend keeping all the information about your insurance policies in one place. In the case of an emergency, it’s important that you can pull a policy up in a few minutes, from anywhere. I store all my information on the cloud rather than my laptop.

Evernote is my go-to storage and organizational tool for everything, including insurance. I have two digital notebooks dedicated to my policies: one for my personal insurance and one for professional insurance. Within these two Evernote notebooks, I give each insurance policy its own dedicated page. Here’s what I include about each policy:

  1. The title of the insurance policy and the accompanying policy number.
  2. The agent and company I purchased each policy from, as well as their contact information.
  3. The start and end date of the policy.
  4. The monthly payment.
  5. The date I need to renew the policy.
  6. A PDF of the policy itself.

If you take an hour to organize all this information, you’ll breathe a little easier. Because insurance often covers “worst-case scenarios,” this kind of planning ensures you can make the most of tough situations. Plus, the best part of Evernote is how easy it is access your notebooks. If you download their app on your phone, you can have everything you need right at your fingertips, which makes it easy to organize your finances.

Add Payment Dates to Your Calendar

I keep track of payment dates for bills the same way I keep track of deadlines: in my calendar. Do you have a tool you love to use? I swear by Asana because it enables me to juggle multiple projects while keeping one cohesive schedule for my professional life.

To manage my payments, I created a project for “insurance” in Asana’s platform and pre-loaded each payment date into the calendar with reoccurring monthly deadlines. This step automates notifications about monthly payments, so I don’t have to use valuable brainpower remembering. I also added in renewal dates to the calendar, which ensures I don’t forget to update my policies on annual basis. Now, my process is set for a year: Insurance payments pop up as daily tasks on my calendar. And because they’re already incorporated into my workflow, it’s easy to stay on top of these responsibilities.

Consider Implementing Auto-Drafts

If you take these two steps and still feel like you want to do more to organize your insurance, consider implementing auto-drafts for your payments. Most insurance companies offer this capability, so you’ll never miss a payment. Make sure to stay diligent about tracking your expenses. Use Evernote to note each monthly withdrawal, and regularly check on your bank account to avoid overdrafts. Sometimes, people forget that they still have to keep track of finances even when they’re automated.

Insurance is a complicated, messy topic — especially for freelancers. The more ownership you can can take over managing your financial life, the easier these monthly processes become. Instead of getting bogged down with dread, organize and automate your payments in advance so you never miss an important bill. It may even inspire you to take the same approach with other aspects of your financial life.

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