I’m on a Career Break. Apparently, My Brain Didn’t Get the Memo.

Nov 7

A sunlit close-up of a young child resting an arm around their mother’s shoulder.

A small arm around my shoulder. One of the very good reasons I’m here.

I’m taking a break from paid work to be home with my two young children, who are three and one. They are wonderful company, although neither has shown much interest in my background in digital optimization. Their priorities are more immediate. Often, those priorities are pretzels.

For nearly thirteen years, I worked at Ulta Beauty, where I built and led a digital optimization practice. I spent a lot of time thinking about how people experience things: where they get stuck, what they need, what we’ve assumed incorrectly, and how we might make something work better.

I loved that work. I still find myself asking those questions, usually while doing something considerably less glamorous than presenting an experimentation strategy.

Recently, I’ve been using ChatGPT to build a collection of personal systems: a daily briefing, shopping and household inventories, meal planning, project tracking, and a place to capture ideas for writing.

This began innocently enough. Help me organize a list. Help me remember a thing. Help me figure out dinner.

Then I started noticing connections.

If you know what’s on my calendar, and you know the weather, and you know I’ll have two small children with me, perhaps you could put that information together before suggesting an outing that requires a stroller, three transfers, and the emotional resilience of an Antarctic explorer.

Apparently, I have left the workforce and become the product manager of my own household.

The stakeholders are demanding. One still eats paper.

The daily briefing: please tell me what this day requires of me

A calendar tells me I have an appointment. It does not necessarily remind me that the appointment requires paperwork, a particular outfit, or a bag of things I promised to bring someone.

Those details live elsewhere: in an email, a text, a list, or the increasingly crowded waiting room of my mind.

I’ve been shaping a daily briefing that brings them together. The aim is to give me a useful view of the day: where we need to be, what needs preparation, what can wait, and what deserves my attention first.

I’ve also asked it to consider the weather and our activities when suggesting what the children and I should wear. This may sound excessive until you have dressed three people, discovered that one is wildly overdressed, and realized that the other has removed a sock and placed it somewhere unknowable.

On lighter days, I want suggestions for outings that account for the children’s ages, the weather, and the fact that I am one adult with two children. “Family-friendly” is a broad category. I would like the more specific category of “pleasant for this particular family to actually attempt.”

To try it yourself, start here:

Help me create a concise daily briefing. Using the information I provide, identify today’s commitments, preparation needed, and three priorities at most. Look ahead for anything that needs action before its due date. Distinguish fixed commitments from optional suggestions. Ask about missing details rather than inventing them.

If you choose to connect a calendar or email account, you can ask it to use those sources. You can also begin by pasting in tomorrow’s schedule. A small experiment is an excellent place to start.

Shopping: a sale is not a household need

I enjoy beautiful things. I also enjoy a discount on beautiful things, which creates certain opportunities for motivated reasoning.

So I’m working on a shopping system that starts with what we already own.

The plan is to build inventories of skincare, cosmetics, body care, and clothing, then use them to inform future purchases. Do I need this? Do I own something that serves the same purpose? Am I replacing a favorite or acquiring a fourth interpretation of it?

Purchase history can help build the initial inventory, but it requires a reality check. A receipt proves that I bought something. It does not prove that I still own it, liked it, kept it, or have any left.

I’ve asked for occasional check-ins to close those gaps: Do you still use this? Are you running low? Did that jacket ever make it out of the return pile?

I also want to track promotions over time. “Ends tonight” becomes less persuasive when we have established that it also ended last Thursday.

A useful starting prompt:

Help me build a practical inventory for one category of things I buy regularly. Track what I own, what I use, and what may need replenishing. Treat purchase records as clues, and ask me to confirm uncertain items. Before suggesting a purchase, check for duplicates and suitable things I already have. Keep the system simple enough that I’ll maintain it.

Choose one category first. There is no need to begin by documenting every possession you have ever welcomed into your home. We all have other things to do.

Meal planning: please remember that I have to cook it

An aspirational meal plan can be a lovely document.

By Wednesday, it can also become evidence.

What I want is a plan that reflects the week we are actually having: a few manageable dinners, useful leftovers, food the children might eat, and enough variety to keep me interested in my own kitchen.

I’m especially interested in the connections here. What needs using up? Which ingredients can serve more than one meal? Is this a week for cooking, or a week for assembling things and calling it dinner with confidence?

Try this:

Plan four realistic dinners for this week using the ingredients and schedule I provide. Reuse ingredients thoughtfully, include one very easy meal, and plan for leftovers. Account for my household’s preferences and available cooking time. Create one consolidated grocery list, separating what I need to buy from what I should check for at home.

Tell it what a difficult evening looks like in your house. That information is probably more useful than your ideal cuisine.

A writing journal: somewhere for the thought to go

Somewhere among the appointments and groceries, I would also like to write.

Ideas rarely arrive when I am seated at a desk, rested, and prepared to receive them. They arrive while I’m driving, cleaning something, or trying to persuade a child that we do, in fact, need to leave.

I’m creating a writing journal where I can deposit fragments without having to turn them into finished work immediately. An observation. A memory. A sentence I want to come back to.

For this system, I want a light editorial hand. Preserve what I actually said. Help me find it later. Please resist the temptation to turn every passing thought into a five-paragraph essay with a stirring conclusion.

Try this:

Act as a writing notebook. When I share a fragment, preserve my original words and date it. Suggest a short title and a few themes so I can find it later. Keep your commentary separate from my writing. Don’t expand or polish it unless I ask.

Sometimes capturing the thought is the entire accomplishment for the day. I would like a system that respects that.

From automations to something more interesting

More recently, I’ve begun experimenting with something beyond the automations themselves: giving ChatGPT a better memory for the practical details of my life, through records we can keep, check, and update.

Take meal planning. With two small children who are picky eaters, the challenge isn’t finding recipes. The internet has a few of those. It’s remembering which foods each child will actually eat, what’s already in my refrigerator, what needs using before it spoils, and what I bought last week.

We’ve started building a little family kitchen database in Airtable, drawing on our ongoing conversations. Recipes, food preferences, pantry inventory, grocery replenishments—all the unglamorous information that makes a recommendation genuinely useful.

The interesting thing isn’t the database. It’s what becomes possible when information accumulates instead of having to be reconstructed in every conversation.

I’ve started applying the same idea to Christmas shopping, my wardrobe, and the household projects that otherwise occupy an unreasonable amount of space in my head. Different tools serve different purposes: Google Calendar knows where I’m supposed to be, Shipt manages my grocery cart, Google Docs holds my writing, and Airtable organizes information that changes over time.

Not everything works seamlessly. Connecting applications doesn’t mean they automatically share information, and a system is only as reliable as the data going into it. I still have to exercise judgment, correct mistakes, and decide what gets done.

But increasingly, I’m spending less time reconstructing context and more time making decisions.

I spent years working in digital experience optimization, thinking about personalization, reducing friction, and making systems more useful through continuous improvement. Apparently, I’ve found a way to apply the same principles to getting two small children to eat dinner.

And perhaps that’s the real appeal of all this. I’m not trying to optimize every minute of my life. I’m trying to spend fewer of those minutes on administration, so I can give more of my attention to the things—and people—that actually deserve it.

Now, if we could establish where the sock went.

Try a small version

I made a two-page worksheet to help you choose one recurring friction, sketch a useful routine, and decide whether it actually lightens the load. There’s a meal-planning example and a prompt to borrow, too.

Download A Little Less to Carry (PDF)