Scaling Career and Family: Systems Thinking, Public School, Home Enrichment

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When asked on The Cheeky Pint podcast how we educate our children, my husband Casey Handmer replied “benign neglect.” It’s a cheeky answer that captures something real: we’re neither tiger nor helicopter parents. But after seven years and three kids (with a fourth on the way), we’ve developed a more deliberate approach. Here’s what we’ve learned.

The Family as a System

If I’ve taken anything away from seven years of parenting, it’s this: the family is a system. Treating it as such, rather than asking “is X better than Y?”, leads to more effective choices.

For working parents who want to scale both career and family, three system-level principles matter most:

  • Reliability is non-negotiable: Even in a flexible workplace, unexpected time off creates disadvantages and logistical hassles. Any out-of-home option needs backup childcare (nanny or easy-to-access service) for inconvenient hours, school breaks, and illnesses. The younger the child, the more frequently you’ll need backup.
  • Over-invest in childcare: Optimizing for convenience, reliability, and family-fit is worth spending more than you’d think, even more than one parent’s salary in extreme examples. This keeps both careers on growth trajectories, builds retirement savings, and makes having more children feel manageable rather than overwhelming. The cost of a nanny grows sublinearly with the number of children.
  • Scalability matters: Decisions that work for one child may not scale to two or three. Time spent driving to individual activities multiplies. Costs of private schooling multiply. We’ve consistently preferred options that work better as our family grows.

The Caveats

This blog details our family preferences alone, which also change over time as we grow in number and maturity. We’re two startup executives with three kids (7, 5, and 2) and a fourth on the way. Our children are somewhat precocious, but otherwise don’t have special needs thus far.

My intention is that this post may provide helpful inspiration to find or tune your own family preferences. If I’ve taken anything away from the past seven years of parenting, it is that it’s helpful to think in terms of global, rather than local, hill climbing towards a better situation. With that, let’s kick things off.

Infancy (Birth to Age 2): Swapping Daycare for Nanny

Emily Oster’s Cribsheet covers from birth through early preschool, and is an excellent data driven read. A key takeaway regarding these years is:

Relative to pregnancy, there are fewer things here where the data will tell you what to do or avoid. Your family preferences will be more central.

What this means is that very few specific interventions actually matter for outcomes on a statistical level. The items which do are the overall quality of parenting and family life.

As new parents in 2018, we had a lot to learn and had relatively simple criteria. Both of us wished to continue our careers with little interruption, so a parent staying at home was off the table. With that our initial considerations were:

  • Does it support both of us going back to work?
  • Is it convenient?
  • Is it sufficiently high quality and within our means?

One additional thing we tried to avoid was an abundance of electronic or “blinky” toys.

Childcare center

In the early days with our first child, we went with a child care center associated with JPL, the Children’s Educational Center, which fit the bill across the board. We both worked at JPL in person and it was just a minute away, on the way to work. I was able to visit at lunch to breastfeed. A fortunate accident of arriving on the CEC after our simple search was that as first time parents, we’ve since adopted much of their approach. They used a combination of RIE (Resources for Infant Educarers) and Montessori style methods as the children grew, as well as a focus on outdoor play even from the youngest age. Some key takeaways from their approach that we’ve consistently adopted:

  • Treating even the youngest infant as a unique human being, not as an object. This means talking to them, walking them through procedures, and sensitive observations of them to understand needs
  • Free movement vs seats, walkers swings or bouncers
  • Increasing independence through independent play and with meals (drinking early from cups, self feeding).
  • Open-ended, safe, passive toys.
  • Spending lots of time outside, with adequate sun protection.

We practice this at home too. Almost all of our house is freely accessible to all of our children, with adults only stuff kept either in a dedicated room or on higher shelves. Mattresses are initially on the floor and don’t have cot sides, only the stairs have gates for crawlers who haven’t yet learned how to safely descend. For infants, free movement means plenty of time on the floor where they can navigate independently. We also set things up generally such that the children can roam. There are no locks (outside of on unsafe areas like our office or garage). And after graduating from a bassinet, the children sleep on floor and later elevated beds they can get in and out of independently.

Although broader data doesn’t support this approach providing uniquely better outcomes than alternatives, thinking of the family as a system there are many key advantages for our family, that have shown up early but been enhanced as our family size grows.

  • Treating infants as humans makes caring for them more enjoyable, and makes it easier to spot their human needs and communication methods earlier
  • Talking to infants helps their language development and even before you could imagine they might understand, and seems to sooth them
  • Getting rid of dedicated entertainment and rather emphasizing observing (and intervening for safety) as the core parenting responsibility, makes parenting at this age more enjoyable. The infant will ask for attention when they need it, vs it being foisted upon them.
  • Self feeding and drinking from cups means mealtimes are more scalable.
  • Being able to get out of bed by themselves is easier for potty training and sibling interaction, and entertaining themselves on the rare occasion they wake before us.
  • The focus on simple toys means a house with aesthetic, useful, playthings that stand the test of time and span ages, appealing to our kids as they grow and even us as adults. Our favorites that begin at this age are magnetiles, blocks, a railway set, and duplo.
A scene from daycare – our eldest, then a baby, plays happily on the floor. Children sit on tables having meals (with light assistance) behind.

Why we switched to a nanny

With our subsequent children, we both had moved on from JPL; I worked remote and Casey quickly transitioned into an in person role leading his startup. Meanwhile, our income had grown along with the size of the family, so the costs and conveniences of a nanny came much closer to childcare, which ran us about $4000/month. We were able to hire a full time 1:1 caregiver, focused on ages 0-2, but available to assist with the other ages when out of school. With two (and soon to be more) children this more effectively supported us going back to work, was of the utmost convenience, was extremely high quality, and while expensive was within our means. The more children we had, the more this method made sense financially, logistically and emotionally, so we’ve “signed” our caregiver for the next 5 years or more.

Advantages of 1:1 care for our family system:

  • Attention sustainability: Neither Casey nor I can focus joyfully on an infant for their full waking hours. A professional who has chosen this calling can supplement our active attention.
  • Sibling time: When our nanny’s hours overlap with other children’s schedules, we can spend 1:1 time with the older kids.
  • Breastfeeding without pumping: Working from home with the infant at home made this seamless.
  • Zero transition friction: Dropoffs and pickups take seconds, no packing, no drama with a steady caregiver.
  • Household support: During nap times, our nanny helps with laundry, dishes, light cleaning, and inventory management. When we’re off work, we focus on children instead of chores.
  • Built-in backup care: As older children attend school, the nanny handles dropoffs, pickups, and care during scheduled or unscheduled days off.
  • 99%+ work reliability: With kids in mixed settings, the chance someone is ill or off school is high. The nanny provides backup, so we consistently meet work commitments.
  • Upside for larger families: Without the short term difficulty of sole caregiving, we revel in family life, rejoice in our children, and want to have more! As we have more children, our childcare cost does not grow significantly. This means that once we’ve built this into our budget, having additional kids doesn’t substantially impact it further.

Infant Care Conclusion

Even considering the educational benefits of our childcare center, having experienced both, I’d choose a nanny for infants given the option. The emotional benefits for infant and parent, plus the system-level advantages, outweigh the learning benefits for first-time parents.

Recommended reading: Janet Lansbury’s Elevating Childcare (use it as a menu of options, not a rigid philosophy) and Loose Parts.

Preschool

While the data is mixed whether communal care before preschool has positive, neutral, or negative impacts on outcome, some preschool starting around age two or three will improve the ease of transitioning to school (Cribsheet). Preschool could have a positive or negative impact on the family system depending on the setup. We again were influenced by our early childcare setting near work, which focused on outdoor play and child-led exploration. Some of the ways in which it aligned with our family’s focus were:

  • Social focus over academics: No drilling on letters, reading, or math. Our kids absorb academic content at home: we’re doing math, sounding out letters, and reading together. What they needed was learning to interact appropriately with peers and adults. Casey and I are unusual adults who didn’t have great social skills at that age, so this was the value-add. Plus, once academic focus starts for bright kids who are already “ahead,” it can be difficult to study alongside peers months or years behind. This has to start sometime, but there’s no reason it needs to before kindergarten.
  • Child-led exploration: with familiar routines and lots of self-directed play
  • Supervised risk-taking: cooking, climbing trees, jumping from heights
  • High quality staff with low turnover
  • No screens or “blinky” toys
  • Authoritative style:  Authoritative parenting combines high expectations with high responsiveness: setting clear boundaries and rules while being warm, supportive, and responsive to the child’s needs and emotions. In contrast, other common styles include authoritarian which is high expectations/low responsiveness, and permissive is low expectations/high responsiveness.
  • Close proximity: 5-10 minutes drive or walking distance, so we don’t spend our lives in the car


How we found it: The NAEYC filter

When we needed something more local, we initially struck out. LA has social pressure for “feeder preschools” among our peer group, plus options with very different focuses, rigid schedules or heavy academic drilling.

In researching, I discovered our original preschool was NAEYC accredited. NAEYC accreditation is essentially a “gold standard” certification that preschools earn by meeting rigorous quality benchmarks focused on developmentally appropriate practices. Using this as a filter led us to a fantastic local option that happened to be a co-op.

The co-op advantage

In a co-op, parents volunteer in the classroom roughly three hours per week to supplement two lead teachers. There are day-consistent volunteers (I always took Wednesdays) with more responsibilities, and floaters who keep a general eye on things and escalate to permanent staff for anything major.

Compared to our previous preschool, the overall staff quality was higher especially post COVID. Parental volunteers were highly educated, empathetic parents who shared our philosophy (hence ending up at the same place), rather than entry-level staff. The permanent teachers had generally been there 10+ years. The atmosphere was more DIY, but they were excellent stewards of parent money, focusing on what matters for development over Instagram aesthetics.

Working from home with teams across the US, I shifted my schedule to start on East Coast hours a few days a week, stopping at close of business Pacific to accommodate Wednesday volunteering. Casey, lacking this flexibility, fulfilled his volunteer hours doing construction projects for the school.

Volunteering was sometimes tough work, but I got to see my kid and benefited from informal education in early childhood development watching the pros navigate the classroom. I’ve worked as a consistent volunteer in the 4-5 age classroom, the 3-4 age classroom, and soon the 2-3 age classroom. I’ll have learned all preschool ages firsthand.

Preschool Care Conclusion

Attending some preschool before formal schooling is probably good, but the data isn’t strong enough to stress if waiting makes more sense for your family. If you want a feeder school for private education or don’t have niche requirements, any school with good staff is probably fine.

If you have similar priorities to ours: play-focused, developmentally appropriate, searching for NAEYC accredited schools is an excellent starting point. Picking a school within 5-10 minutes of home has significant family-system advantages. If you can volunteer or participate in a co-op, the education in your own parenting development is valuable, and I believe investing time to volunteer at this stage benefits both parent and child more than volunteering at later stages.

Recommended reading: Cribsheet by Emily Oster

Kindergarten and Elementary: Maximizing the “Typical School Experience”

Our kids track 1-4+ grades above in reading, math, and other core academics, with the gap seeming to accelerate over time. They remain grade-level in handwriting, social skills, executive functioning (homework and test-taking diligence), and rule-following.

Why we chose public school while we still can

We want to take advantage of the time when this gap is manageable to focus on grade-level skills and give them a “typical school experience” as long as possible. We expect their schooling will need to deviate from typical more in the future.

There’s a perception that parents drive the acceleration of kids tracking above grade level. My experience is the opposite: kids like this thirst and hunger for knowledge, so acceleration is kid-driven. You’d no more deny it to a child thirsting for it than you would a glass of water.

Our values driving our elementary school choice have been

  • Convenience: Close to home with minimal driving.
  • Typical experience: Age-similar peers, similar routines, focus on basics over bells and whistles.
  • Flexibility: Amenable to various options for academic acceleration so we can keep this mode of education as long as it makes sense.
  • Quality: Basic quality of educators and system, with good odds of matching with teachers who work well with our kids.
  • Cost: This is where our systems thinking diverged from preschool/infant care. Investing heavily in a nanny or preschool makes life easier on the whole family: worth every dollar. Private elementary school wouldn’t increase reliability or convenience for us while offering marginal educational benefit and decreased normalcy. A nanny benefits multiple children for approximately the same cost; private schooling scales up with each child. When private school offers significant educational benefit and normalcy is no longer possible anywhere, we might reconsider (stay tuned!).

How it’s working

We chose the local public school. It’s walking distance or a short drive, has good ratings (matched by our kids being paired with great teachers), and is approximately free. All teachers are trained in gifted education, and while we don’t expect their clustered grouping approach (as opposed to academic streaming) to be especially useful, teachers have been flexible and creative about differentiated options. Our eldest does math warmups two grades ahead and accesses curriculum three grades ahead during math study time. Our younger gets books tailored to her reading level, alongside kids in her classroom receiving more or less advanced material during reading time.

They’ve made friends, including some similarly curious kids. Much of their school time involves moving between activities, recess, and enrichment classes: art, gardening, PE, music, classroom runs, alongside handwriting, spelling, and socialization with age peers. That is to say, the majority of their day doesn’t require differentiated curriculum, and the portion which does they blend in well with others receiving the same (at higher or lower levels).

The homework approach

There have been hiccups. We weren’t paying attention to kindergarten homework with our eldest until he complained math was boring. When I looked, I realized we needed to give him challenges (see Enrichment section below). After providing after-school opportunities to learn math in a structured way, he hasn’t complained since. In later grades we paired with his teacher to provide some of these opportunities at school as well.

Homework continues to be straightforward for both children. We debated requesting or inventing more challenging homework but decided against it. Instead, we go deep on the homework they do have, focusing on executive functioning, diligence, and improving at-grade-level skills. The math may be straightforward, but writing answers clearly, checking work carefully, paying attention to details, and completing and turning it in on time may not be. Since it is straightforward, this typically doesn’t take much time for anyone involved, and the time invested seems worth it for the returns.

Why this works for our family system

Public school requires no driving logistics that multiply with family size, and costs nothing while our children can still thrive there. The kids are picking up key social skills in additional to their educational advances and have the opportunity to experience a rite of passage shared by most Americans.

Recommended reading: The Family Firm by Emily Oster

Enrichment and Extracurriculars: Prioritizing Family Time

What we skip and why

We prioritize family time together, keeping weekends largely free. This means we can spend time as a family, taking advantage of the big family we’ve built, while keeping logistics manageable. Carting one child around from activity to activity can be overwhelming; carting a large family to individual activities can be prohibitive.

As simple as it sounds, this choice seems fairly unique among our friend group. As trivial an objection to scaling a family as it might seem (“Johnny never had a sister because we wanted him to play t-ball”), I get the sense it plays a huge factor when people with one or two heavily-scheduled kids say they could never imagine having a bigger family.

We opt out of group sports at elementary age. Families with sports as a core value would make different decisions. We do physical activities together: climbing, biking, hiking, walking, and physical play. We’ve had the fortune to move to a walkable community with sports options, so as the children grow older they can walk themselves to practices in areas of their interest.

What we offer at home

We focus enrichment activities on what’s available at home.

  • Piano A teacher comes once a week to our house and teaches our kids. We are a musical family and value the kids having piano as a foundation to electively build upon.
  • Math enrichment. While I prepare dinner, the older kids have the opportunity to self-study from books and online curricula. I’m available to mentor. It’s gotten to the point where my eldest enjoys mentoring my younger, which also cements concepts for him: win-win-win. We use a combination of:
  1. Beast Academy: a math curriculum with comic books and online/offline options. It’s rigorous, creative, allows self-study, and is fun for our kids.
  2. Adventures with Mr. Math: Zoom classes focusing on using analytical reasoning skills to solve difficult math problems and puzzles. This doesn’t teach math but rather teaches problem solving. The homework and coursework provide an awesome challenge.
  3. Custom problems: We dive deep on exciting problems together some of which are hard for us to solve as mathematically advanced adults. The kids don’t always have the tools in their toolbox, but we approach them together.
  • Chess: Our eldest takes group chess classes at any level through International Chess Academy via Zoom. This wasn’t in the plan, but he participated in a chess activity at his homework club and when it was discontinued requested to find another option. We were delighted to stumble upon one online that has worked well
  • Strewing. We participate heavily in “strewing” both accidentally and on purpose:

Strewing is the intentional, casual placement of interesting materials (books, puzzles, art supplies, science kits, etc.) around the home environment where children will naturally encounter them. The key is that it’s done subtly—you’re creating an enriched environment without directing or requiring the child to engage with the materials.

We have a great variety of material on diverse topics at home and regularly visit the library to check out and strew more. As a result, we regularly hear “I’m sorry I got stuck in a book!” when following up on why a key activity (getting dressed, taking a shower, putting on shoes) wasn’t completed in a timely manner. There are worse problems to have.

Beast Academy – a math curriculum with comic books and online/offline options. It’s rigorous, it’s creative, it allows self study and it’s fun for our kids.

A Brief Note On Screen time

We take a selective approach to screen time, emphasizing tools over passive consumption, and focusing on moderation. The thinking: learning to use these powerful tools is a modern skill, and in the right contexts, they can function as an Illustrated Primer in service of personal growth and education. The kids use screens while in view.

  • Outside the home: No screens. Including none on roadtrips.
  • Passive media at home: We watch together occasionally: rocket launches, documentaries, Veritasium, chess videos, Mark Rober (limited: more edutainment than education), and other media of broad interest that is education adjacent. The kids don’t watch media alone.
  • Active learning with screens: Starting around age two, we introduced limited computer or iPad time.

Useful apps and sites we’ve found:

  • Ages 2-4: Khan Academy Kids on iPad. Free, ad-free content mixing fun with education. Extensive library of books with read-aloud option available offline.
  • Ages 4+: Beast Academy online options. The online version is particularly engaging and offers read-aloud mode for pre-fluent readers. The kids use the books as well, but when given the choice gravitate toward the computer version.
  • Post-fluency readers: Scratch.mit.edu for coding concepts, Replit for AI guided programming (limited, more edutainment than education), Google Colab for advanced coding concepts, Onshape for 3D printing, ChessKid for chess, Google Docs for typing and notes, Gmail for communicating with grandparents.

Finding resources: the Davidson community

I have a friend whose children seemed so similar to ours, we swapped educational tips frequently, and I have her to thank for stumbling upon many. On top of that, she introduced us to the Davidson Young Scholars community which offers a variety of free resources to families with gifted children as well as a community forum. Since her kids were eligible and seemed so similar to ours it was no surprise when we qualified as well. This has been helpful in seeing that there is no perfect educational fit for similar kids, as well as discovering new potential enrichment areas.

Bottom line on enrichment

Our approach maximizes convenience (everything at home or via Zoom except one piano teacher visit), keeps weekends free, and scales well with family size. Kids pursue what interests them without the pressure or logistics of scheduled activities all over town.

Recommended resources: Beast Academy, Adventures With Mr. Math, International Chess Academy, Davidson Young Scholars Program and Forums

Beyond Elementary: Our Evolving Plan

We haven’t crossed this bridge yet as our children are solidly thriving in infant care, preschool, and elementary school. But based on the Davidson Forums and our research, beyond elementary is where things get complex, requiring a tapestry of approaches with none of the off-the-shelf options (whether private or public, gifted or not) being a perfect fit.

Our current thinking

We’re inspired by research including Bloom’s two sigma problem, the finding that students taught one-on-one with mastery learning perform two standard deviations better than students in traditional classrooms. We’re also drawn to the observation that high-quality 1:1 tutoring alongside self-directed learning can be significantly less expensive than private schooling.

We’re not setting aside money for private school at the middle school, high school, or college level. In our experience, this can be a family size limiter (“Jane never had a younger brother because we wanted her and siblings to signal high status by attending $40k/year schooling for a decade”). We expect to prefer investing that capital differently and forego status signaling, focusing on educational outcomes instead.

That said, for the right educational outcomes, we’d consider investing. Our priorities will likely be:

  • Actual learning over credentialing: Brian Caplan’s The Case Against Education argues that the majority of education’s value at upper levels comes from signaling versus actual learning. We’re inclined to focus on the learning.
  • Kid -driven and kid-led: We expect our children’s education to be driven by our children’s needs, not our own desires for status or projections of our desires onto theirs.
  • Mix and match approaches: We expect to weave together coursework at various levels, 1:1 tutoring, self-directed study, and possibly dual enrollment or online options.
  • Maintaining social connection: Whatever we do, we want our kids to have peers and community, not just academic advancement in isolation.
  • Flexibility as needs evolve: What works at 12 may not work at 15. We’re prepared to adjust.

We don’t have it all figured out

We’re learning from families a few years ahead of us and staying open to creative solutions. I’ll write an update to this blog when we have more life experience to back up our initial thoughts.

Recommended reading: The Case Against Education by Bryan Caplan

Executive Summary

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