The Grandparent Gig

New roles, old tracks, and the lessons that still apply

Imagine the ideal grandparent. Good, kind people come to mind. Wise and ready to help out, even if they are still working and figuring things out themselves.

That's the grandparent I thought I would be. And then, I became one.

Becoming a new grandparent is a transition into a new role with as many requirements of flexibility and adaptability as any new job you've taken throughout your professional life.

Three "work things" echo from corporate life for this new grandparent.

The "continuous learning" mindset

Raising X children won't make you a credible source of wisdom for new parents. Expect to learn how everything is done now.

It's not that the way to raise a child has changed that much (the routine my mother taught me to impose is still king). What's changed is that the experts are no longer neighbors or grandparents; they are much younger influencers with more recent experience about what raising a child today entails. It's hard. It's joyful. You got this.

In this community-by-algorithm, new parents scroll through curated routines, product lists, and how-to videos, building empathy with creators who, unlike grandparents, offer no judgment or annoyingly strong opinions. I understand the appeal. It likely feels safer, and if they can do it, so can you.

Grandparents can adapt by letting go of all the expertise they thought they'd be dishing out. There are other ways to be relevant: cooking, cleaning, and keeping them company on the floor during tummy time.

I learned how to induce a burp without back tapping, how to play more quietly, and new food routines. I watch my grandson sleep on Nanit, which is as hard to disconnect from as your TikTok feed.

Instead of saying, "Let's do this like I know how to do it," we say, "I haven't done it this way before, but I'm open to learning."

Like everything else, grandparenting has changed

Grandparenting could be a new black hole of being on call 24/7 – and you can still claim to do it because "I love my job!" But it's complicated.

In a recent Atlantic article, Grandparents Are Reaching Their Limits, Faith Hill, a writer I follow who focuses on cultural and societal trends, describes the evolving role of grandparents in America and how grandparents, particularly grandmothers, have become co-parents due to economic, cultural, and workplace shifts that leave many new parents without other options.

It's complicated because while on the one hand, grandparents want the best for their kids and grandkids, on the other, there is a level of involvement that could well lead to exhaustion and financial strains.

I live on a different continent from my grandson, so there is a natural, firm boundary on my involvement in his life. But if we were close and support needs were different, would I be any better at establishing boundaries than I learned to do at work?

In her article, Hill touches on grandparents who "are trying desperately to set limits on that involvement." They do this by limiting help to specific days of the week, committing only to certain types of activities, and, as a measure of last resort, semi-regularly ignoring their adult children's calls.

In the end, the desire to help grandchildren often overrides the intended limits.

Your best work is what you most love doing.

There, right before you, is proof that you did good.

In my first ever (still pinned!) QC essay, I said there were three themes I would always return to. The first one was:

You'll do your best work when you engage in something you love. Sometimes, we are lucky enough to be assigned work that we love. More often, we have to grab it or create it.

This is true whether you're building a company, running a team, or raising a human. The work you love is the work you'll do best. It will outlast you.

I worked hard to become a parent, and once I did, I poured a lot of effort into raising my daughter and her two siblings. It stretched me and made me better.

Now I see her doing the same, differently, but with so many similarities, showing her whole heart, emotional labor, time management, logistics, and love all rolled into one.

[K]Now You: Repeatable Patterns

Notice how life's patterns repeat themselves, over and over again.

Parenting and grandparenting, work and purpose, learning and unlearning—it's never a one-off; it's an infinite number of loops, spirals, and echoes.

If we’re paying attention, we can see it, remember how it felt last time, and catch ourselves reaching for the familiar response. We can also choose to do something different.

We're like Formula-1 race drivers who get to know the track, improving performance with each loop. Once the race is done, they move on to another city for the next race and start again, bringing the skills they carry and learning anew.

Eventually, they'll stop racing high-octane machines. They may become grandparents, Substackers, or something else entirely different.

You'll see repeating patterns each time around, and you'll bring more awareness and grace. The curve of understanding—about ourselves—keeps moving up.

Growth happens not from mastering a pattern by rote but from doing it a little bit differently each time.