Dear Diary

Where There’s a Will (and Life Insurance), There’s a Way

Let’s get the obvious out of the way – planning for your own untimely demise is not a fun, easy, or approachable task. When you’re young and healthy (/healthyish), it’s easy to push writing a will and investing in life insurance to the bottom of your to-do list, or even out of mind entirely. I know I never gave it a second thought. 

It wasn’t until I had Summer early last year that I realized I hadn’t put any thought into where she, my pets, and my belongings would end up if something happened to me. How would my assets be divided? How could I ensure Summer would be well taken care of well into adulthood. It’s a heartbreaking thought process to have to walk yourself though, but I’ve witnessed firsthand friends and family fighting over the estate’s of loved ones when they are no longer living, and I wouldn’t wish that pain and drama on my worst enemy, never mind my child.

Initially I asked my parents about how to make a will, but they immediately lost me between lawyers, executors, and fireproof file storage. The whole process seemed daunting and outdated, so I figured I’d just write a note with my wishes, sign it, and stash it somewhere safe, just in case. 

Life insurance was just as complex, and looked very expensive at a glance. For someone with a young child and no second parent in the picture, like me, the amount of money I’d need from a life insurance policy to keep Summer comfortable for the next 20 years was formidable. Was it really worth it to add yet another expense to my monthly bill total? 

And then COVID-19 happened.

The current pandemic has put so much into perspective for me, including how unprepared I am if something unexpected were to happen to me. It’s so crucial to have a plan in place, especially as a parent, if only for peace of mind, but when it finally sunk in that I needed to take action, I had no idea where to start! 

That’s where Willful and PolicyAdvisor come in. Both of these platforms are geared specifically toward making afterlife planning as quick, affordable, and painless as possible. If you like doing internet quizzes to pass the time, it’s almost as easy as that. Both operate online, and both are social-distancing compliant – Willful requires two witness signatures on all printed documents, which can be difficult if you’re in self isolation. Fortunately, Willful put together a list of helpful tips here to navigate how to make your new will official. PolicyAdvisor offers digital signatures and several life insurance options that can be arranged entirely over the phone, with the policy delivered by email to you.

I had some concerns I hadn’t acted quickly enough with life insurance, and that a death related to COVID-19 may not be covered, but Policy Advisor had already addressed all of my questions in a handy post here. Basically unless you’ve already been diagnosed with COVID-19, you’re totally covered by life insurance, even a new policy, in the event you do become fatally ill. 

I know this is a departure from my typical optimistic content, but it was such a massive weight off of my shoulders to get my estate in order for the future, so I could get back to appreciating the now. Even if you don’t have kids, it’s important to have something in place to help your loved ones navigate life without you, from your wishes about a funeral and remains, to leaving money to take care of your pets. It’s a weird process, but both Willful and Policy Advisor make it as simple as possible, and when all of the documents are signed, I promise you’ll feel a lot better, pandemic or no pandemic. 

Here’s a snapshot of what happens when you login to Willful:

One of my favourite things about this platform is how easy it is to make edits to your will as things change in your life (for example, the founder joked about how important it is to edit after a divorce or breakup, otherwise your ex could end up with everything!) Just remember – only a printed and signed will is valid, so make sure any new versions are printed, signed, and stored in a safe place as soon as possible!

Fun Fact: They also made a handy little card game (available here) to help you discuss your wishes and ask those tough questions with friends and family. I highly suggest playing a round over a glass of wine next time you’re all together (or via Facetime right now!)

And the same for PolicyAdvisor:


Any kind of insurance can be intimidating to set up (and set up properly), but PolicyAdvisor.com uses an online quote calculator system that couldn’t be simpler! I was surprised how little information was needed to get an initial quote, and how easy it was to setup a call with an actual person to make sure the plan I chose was right for me. The option to sign digitally was also a huge perk (how many of us have in-home printers there days?!)

In the end I went with higher coverage because Summer is so young, but chose a 10 year term to save money now, and allow me to make changes as she grows and my needs shift.

Ready to get your estate in order? Use code “PASTEL15” for $15 off any Willful plan (no expiry!), and then visit PolicyAdvisor.com to try out their hassle-free insurance calculator.

This post was a paid partnership with Willful and Policy Advisor, but all opinions are my own, based on personal experience with each platform. 

One comment

  • Hi Alyssa,
    First of all , your design and brand is really beautiful ! Without going into detail , I actually read your exit out of the C3Church , not intentionally … I thought your story was very well written and I felt sorry that you had been misled . I am a Roman Catholic and a married mother of 6 ( some your age . ) Just to give you a reference that while in principal and in conscience , I believe in traditional Christian Marriage , I respect anyone God created no matter what their lifestyle and beliefs . I applaud you for choosing life and bringing a child into the world as any child is a sign of hope for humanity .. Your work reminded me of an e magazine , not as successful as yours I’m sure but wanted to share it with you . It’s called Verily Magazine . I think you would make a great addition to some of their content ? If you are interested in finding out more about it or even want to talk to an experienced mom please feel free to reach out . No proselytizing here , I just always like to connect with strong positive women ( mothers for that matter) I just watched Michelle Obama’s doc. , it was excellent . In any event . I hope you don’t mind me reaching out to you here . Happy Mother’s Day ! I am on Facebook ( on and off ) you will see I’m no t a weirdo !!! Promise .
    Hope this comment gets to you 🙂 Thanks !

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