There’s an old saying: you overestimate what you can do in a year, and underestimate what you can do in ten. At Robins Hollow, that truth has been our north star.

When we bought this nearly 200-year-old Queen Anne Victorian, we made a ten-year plan. Not a rigid roadmap, but a vision for how the property should feel: the porches alive with seasonal displays, the grounds cleared and breathing again, the rooms restored to their former warmth.

Almost five years in, I’ve learned two things: life rarely unfolds the way you think, and the house itself always gets a vote.

The Long View: Why Ten Years

We live busy lives. Sean and I juggle two demanding careers, school rhythms for an eleven-year-old, community events, family visits, and a steady stream of neighbors stopping by. Layer onto that the reality of an old house: water lines that break, porches that sag, lawns that swallow hours of mowing. If I only measured our progress in one-year increments, I’d probably cry into my favorite handmade coffee mug.

But when I zoom out, the picture changes. I see the shag carpeting we’ve peeled back to reveal wood floors, the barn and ice house that have reemerged from under decades of overgrowth, the kitchen woodwork lovingly (and painstakingly) restored with our own hands.

These weren’t all on the original “Year One” list, but they’re part of the layered progress that makes up a decade of stewardship.

That’s why we set a ten year plan. It’s enough time for life’s interruptions and surprises, enough space to hold both the big, transformative projects and the small, invisible acts of care.

The First Five Years: Seasons of Work and Life

Our first two years at Robins Hollow coincided with the pandemic. Like many, we found ourselves rooted in place — just us, the house, and endless hours to chip away at projects. It was a time of clearing, scrubbing, discovering what lay beneath.

By year three, guests began to return. We shifted from solitary caretaking to hosting, sharing meals at long tables and porch cocktails at sunset. The work didn’t stop, but it began to bend around relationships again.

These last two years have widened further. Travel has returned — trips to explore architecture and food elsewhere — and our days are more fragmented. Some weekends, projects give way to beach days or last-minute flights to see family. Other weeks, the house itself insists on rearranging our plans (like the spring when the well failed and we suddenly became intimately acquainted with the logistics of town water hookups).

The rhythm has ebbed and flowed, but the vision has remained steady: slow progress toward a house that feels both restored and alive.

Planning as a Ritual

We joke that Robins Hollow attends its own planning meetings. Each winter, we sit down with a notebook, a glass of wine, and our competing instincts — me with spreadsheets and timelines, Sean with sketches and ideas that start with “wouldn’t it be cool if” — and plot out the year.

We list the big projects, quarter by quarter. Then we add the medium ones, and finally scatter in the small ones that keep momentum going. Inevitably, it’s overambitious. And inevitably, the house edits our plan. A surprise leak, a fallen tree, or an irresistible opportunity (like the skip laurel hedge that arrived unannounced at a local nursery this spring) can rearrange priorities overnight.

But here’s what planning does: it creates a rhythm. Even if the list changes, we’ve already carved out the time and mindset to act. We don’t waste energy wondering “what next?” — we adjust and keep going.

The Messy Middle: Learning to Re-Plan

The truth about old house care is that it’s never done. Projects sprawl. Punch lists linger. Deer run through fences.

Instead of getting discouraged, we’ve learned to re-plan quarterly. At the end of each season, we ask: what got done, what didn’t, and what new things cropped up? Sometimes the patio redo gets pushed another year, but in its place, a hedge gets planted or a water system gets upgraded. It’s not failure — it’s the reality of balancing vision with care.

And honestly, sometimes it’s us who throw the plan off. A September fence day might get traded for one more beach afternoon. A weekend earmarked for trim painting might turn into a trip to visit cousins. These diversions aren’t failures either.

They’re part of the life we’re building within the house.

Practical Lessons We’ve Learned

If you’re trying to balance an old house (or even a new one) with a busy life, here are a few practices that keep us sane:

Make a long-term plan. Ten years gives you perspective. It frees you from the pressure of cramming everything into one year, while keeping you moving toward a vision. Get your sketches on paper when they strike, then you’ll have your ideas ready when it’s time to start.
Break it into quarters. Pick 1–2 big projects per year, plus a handful of small and medium ones per quarter. It’s manageable, and you’ll actually feel progress.
Expect the house to weigh in. Old houses surprise you. Don’t resent it; build slack into your plan so surprises don’t derail you.
Chip away. Break big tasks into smaller chunks. Momentum builds with every board repaired, wall painted, or weeded bed.
Re-plan often. Adjust quarterly. Celebrate what you did do, and shift the rest forward.
Get help where you can. Old houses once had staff for a reason. We’ve created our own “team” — a house cleaner, a gardener for heavy lifts, and a pond guy. Outsourcing doesn’t make you less of a steward; it makes you sustainable.
Automate the basics. Bill pay, subscriptions, deliveries — anything you can set on autopilot frees up time and brain space for the bigger things.

Sketches for the primary suite project , which will include a new bathroom in the current ‘bonus room’.

The Trap of “All at Once”

There are days I’ll admit that I wish we had the money to restore Robins Hollow in one grand sweep. Or that we’d chosen a cottage instead of a property with barns, outbuildings, a tennis court, pond, and two and a half acres of property.

But then I remind myself: the slow layering is what makes it ours. A decade isn’t a delay. It’s the timeframe in which legacy takes shape.

We’re not just living at Robins Hollow; we’re caring for it, shaping it, and letting it reveal itself — one project, one season, one act of attention at a time.

The Secret to Finding Time (When There’s Never Enough)

Grab your favorite mug and start the conversation this weekend!

So where do we find the time? By zooming out. By holding the tension between vision and daily care. By planning ambitiously, re-planning realistically, and giving ourselves grace for the surprises.

The progress that feels invisible in the moment becomes visible in hindsight — when you realize the shag carpet is gone, the barns are clear, the hedge is planted, and the house breathes easier because you kept at it, one season at a time.

That’s the secret: you don’t find the time, you make it — in small, consistent acts that add up over years.

Join the Conversation

What about you? Do you keep a ten-year plan for your house, or do you let the seasons guide you one project at a time?

Share your rhythms, struggles, and wins in the comments — we’d love to hear how you balance vision and care in your own home.

👉 Visiting the North Fork? Don’t miss our local favorites for seasonal plants, pumpkins and supplies: Krupski’s, Harbes Family Farm, Gabrielsen’s Country Farm.

Where Do You Find the Time?