With the High Holidays around the corner, I have noticed my usual light bout of pre-holiday anxiety. So much always seems to ride on this part of the Jewish calendar. For strong believers, there’s the spiritual reckoning. For the less religious who still care about affiliation, there’s the loaded nature of synagogue attendance, compounded by the challenge of pricey tickets. And for the simply social, there’s the pressure of ensuring some communal marking of the calendar.

Amidst all this, Reboot – an organization that says it “affirms the value of Jewish traditions and creates new ways for people to make them their own” – is taking a lighter touch: its annual 10 questions project. Starting on Sept. 13 and lasting 10 days, the website will email you one question per day encouraging participants to engage in the kind of personal reflection that is customary during the intervening days between Rosh Hashanah and Yom Kippur.

Once completed, the answers are sent to the Reboot “vault” for safekeeping, and users can decide whether to share them or not. Either way, one year later, Reboot will send the answers back to the participant. And the questions will be posed again, so that one can see what changes in life perspectives occur over time.

It’s a truism that Jewish life is fundamentally communal. A quorum of 10 is required for some prayer; weekly Shabbat dinners are often an extended family-and-friends affair; Jews are encouraged to educate their children Jewishly in a group setting; Jewish summer camp focuses on intense communal experiences; and bar and bat mitzvahs are marked by a public aliyah to the Torah.

So are individual, web-based initiatives like Reboot’s enough to scratch the itch of Jewish communal practice? Or are they – in their push-a-button sort of way – a frivolous addition to what should be undivided attention to the technicalities of Jewish literacy, and to the bricks and mortar of conventional Jewish life where Judaism is experienced publicly and communally?

This question isn’t a surprising one, but it may be misplaced.

In the age of “destination” bar and bat mitzvah ceremonies, where almost no one from one’s community may be in attendance; and in the age of concierge Judaism – a term the Jewish Outreach Institute now uses to suggest that Jews may be looking for an array of products and services tailored to their own individual needs; and in the generation of the millennial who seeks to refashion Judaism to suit her own sensibilities, Reboot knows that one has to reach Jews where they are.

But there’s more to it than simply realizing that initiatives like Reboot may be what’s needed to save do-it-yourself-style Jews from disconnection.

Despite the absence of Hebrew or Jewish texts or a group of Jews sitting in a study session with a rabbi, initiatives like the 10 questions project are not a challenge to Jewish literacy at all. In discussing the initiative with colleagues, I realized that without Reboot’s initiative, I might never have given those intervening days another thought.

In my typical hectic pace, I would likely be rearranging my work schedule, securing a break-fast invitation for my family or deciding whether to host one, and practising the Haftorah my shul has asked me to prepare for Yom Kippur morning.

No doubt the personal reflection bit would fall by the wayside, and even if I did try to engage in it, it likely would not be as fulsome as that encouraged by the kinds of daily questions Reboot sends. That kind of thinking and writing – including being faced with one’s past challenges – takes immersive effort, both intellectual and emotional.

So tailored and trendy versus tried-and-true may be a false dichotomy after all. We would be better placed to think of Jewish life as being enriched by as many touch points as our current crop of Jewish innovators can create.