These digital tools can take the tedium out of your to-do list

Tax season may be over, but adulting never ends. Some Canadian online platforms are making it easier, cheaper and less painful.

The other day I got my first ever invite to an Admin Night. For those of you high-functioning enough to have avoided this trend, Admin Nights are social gatherings, where instead of discussing a book or sharing a bottle of pinot, the goal is to spend time with friends addressing those tedious tasks now collectively known as life admin: paying bills, doing taxes, etc. If, like me, your to-do list has a tail stretching back to the Obama administration, these events can be a godsend, allowing you to finally get a handle on the bureaucracy of everyday existence.

But Admin Nights are more of a symptom than a solution. Not-so-fun fact: Canadians are spending more time than ever on the unpaid labour of adulting, nearly four hours a day for women and 2.4 for men. We all basically have an additional part-time job. To really reduce this time, we need tools that make these tasks easier, cheaper and less painful. Thankfully, a few Canadian companies are doing just that, trying to turn adulting into — dare we say it? — child’s play.

Ending the procrastination cycle

Kevin Oulds and Erin Bury faced a new set of adult responsibilities in 2016. That year, Oulds’ uncle passed away unexpectedly. The death was a shock, but when it came time to make funeral arrangements, sorrowful surprise gave way to unpleasant confusion. The 67-year-old Ontarian had a will, but had provided no further instructions nor discussed final wishes with his wife of 40 years. It was an oversight that led to arguments between loved ones who had different ideas about arrangements and how to deal with his estate.

After witnessing all the postmortem tension, the Toronto couple went to get their own wills done. Their lives were pretty straightforward (no kids, regular jobs — he worked at a cement plant, she in tech marketing), but they were nonetheless quoted a thousand dollars and would have to take time off work to meet with a lawyer. “It felt very intimidating and, frankly, unnecessary,” Bury tells me. Inspired by Wealthsimple, the investment and financial advice platform, they set out to build something similarly accessible and useful for end-of-life plans.

In 2018, they launched Willful, a one-stop shop for will preparation, power-of-attorney and funeral planning. Three years later, Bury and Oulds appeared on Dragon’s Den, securing $750,000 from angel investor Michele Romanow, which funded the company’s cross-Canada growth. Today, Willful has more than half-a-million subscribers.

When I first spoke to Bury, I was not one of them. As I confessed to her, I’m a 47-year-old parent without a final testament. “It’s been on my to-do list for ages,” I tell her with audible guilt. I’m not alone in my negligence, however. More than 50 percent of Canadians don’t have a will, and Canadians with children are doing only slightly better. When it comes to adulting, the tasks most likely to get our attention are the ones that feel fun (booking vacation!) or time sensitive (camp sign-up!), while others pile up like so much unfinished laundry. And then you leave your house one day and get hit by a bus and whoops — about that will…

“The road to end-of-life planning is paved with good intentions,” says Bury. “I think part of the block is emotional — who wants to sit down and think about death?” Bury says. “What parent wants to imagine not seeing their kids grow up?” And so, preparing for your ultimate but unpredictable demise lands somewhere between booking a doctor’s appointment and Goodwill donation drop-off.

Crossing life insurance off your list

Andrew Ostro is a licensed actuary who spent years offering insurance advice to distressed friends and family. It was helpful, but not exactly a scalable model. So in 2018, he co-founded PolicyMe, a digital-first life insurance platform he envisioned as a way to make a dreaded duty more doable.

“When we think of our customer, it’s the person who is already planning to get life insurance,” Ostro says. “So it’s less, how can we convince you, and more, how can we help you cross it off your to-do list?” The company recently published a Life Insurance Gap Report showing that 42 percent of Canadian adults don’t have life insurance. Nearly half of that group cite cost as an obstacle while a quarter are put off by the possibility of medical tests.

Using AI-powered data and predictive models, PolicyMe removes both these friction points: medical checks are made unnecessary and by removing that particular middleman, the company can lower costs by 25 percent. It also, Ostro argues, relieves some of the tedium of the process. Like getting a will, people avoid life insurance simply because it’s a chore they don’t want to think about.

Putting his promise to the test, I put on a pot of coffee before I sat down to fill out an application. I got a quote for monthly coverage before I could fill my cup.

Dealing with debt

It isn’t just the big sleep that inspires counterproductive levels of dread. In fact, a survey by Credit Karma showed that Canadians fear debt almost as much as we fear death. Which explains why so many of us are reluctant to check our credit scores, report cards on a lifetime of poor impulse control.

Eva Wong is the co-founder and chief operating officer of the Toronto-based personal finance platform Borrowell, the first Canadian company to offer free credit checks (among other financial product recommendations). Wong describes the service as equivalent to ripping off a Band-Aid. With one relieving wrinkle — the festering wound you feared may never have been there in the first place.

“If you look at how many Canadians believe they have a poor credit rating, the facts just don’t back that up,” Wong says. Indeed, the average Canadian has a “good” credit score, and even those who fall into the debtor minority may be harbouring self-destructive misconceptions. “People believe that once you have bad credit, there’s little to do to change that,” she adds. “When, in fact, something fairly basic like paying bills on time can make a huge difference.” Rather than reinforce the shame cycle, Borrowell is part cheerleader, part personal trainer: “We’re trying to encourage people by emphasizing the positives. Our messages include a lot of praise emojis.”

Wong believes that credit score apprehension is rooted in the realities of previous generations — getting a score used to take weeks and cost a few hundred dollars. But while technology has made things easier and cheaper, it’s also, as is almost always the case with tech, a double-edged sword. Wong recently had dinner with a friend’s family, where the “kids” were in their late teens and early twenties and already talking about passive income and penny stocks. “They had so many questions for me about credit and savings and the best ways to build wealth,” Wong recalls.

That’s an understandable mindset in a world where a stable, predictable career path is about as likely as a Loch Ness Monster sighting. At the same time, there are currently tools and tactics available that would have been unthinkable 20 years ago. Perhaps the next gen will be better equipped to manage the melee? On the other end of the spectrum, Wong recalls Borrowell’s first week of business where one of the people who signed up for a free credit check was 100 years old.

Adulting is a journey, not a destination.

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Photo illustration: Stephen Gregory; photos: Unsplash