Build a Portfolio of Places

My wife and I recently returned to San Francisco, where we lived for roughly a dozen years. Those years spanned several chapters of our lives, from dating to early marriage to starting a family. Returning brought back memories of the neighborhoods we called home and the life we built there. We also reconnected with friends who helped make those years meaningful. San Francisco remains a beautiful place, but its pull on us goes well beyond the scenery. For various reasons, we probably wouldn’t move back. Yet the visit raised a question. Could we make San Francisco a more regular part of our lives? Returning intentionally might help us maintain friendships, deepen our connection, and feel more grounded in a place that helped shape us.

The Opportunity to Think Creatively

When we ask, “Where should I live?” we often assume the answer must be one place. We search for a home and community that can meet nearly all our needs, then imagine spending almost all our time there. During some life stages, that makes sense. Raising young children often anchors us to schools, work, and routines. Later, greater health needs may make proximity to care and a reliable support network especially important. But other chapters can offer more flexibility. Remote work, fewer family obligations, or retirement may allow us to establish a home base while spending meaningful time elsewhere. Snowbirds have long practiced a version of this approach. The broader opportunity is to think beyond weather and consider where we feel connected. Perhaps close friends live across the country, or a former hometown still feels like part of us. What if we thought about a portfolio of places rather than just one place?

One advantage is that it takes some pressure off our primary home. Few places offer everything we want. We might love our everyday community while missing the cultural life of a larger city, time near the water, or friends who live elsewhere. Regular visits can help us make room for those experiences. Returning to the same place also creates opportunities that occasional sightseeing may not. We can learn its rhythms, develop familiar routines, and make plans with people whose company we value. Over time, those visits can help us assess a possible future home. A place that initially serves as an occasional retreat may become somewhere we want to spend several months, and eventually most of the year. We get to learn through experience before making a larger commitment.

Being Away from Home Too Often Can Cause Strain

There are tradeoffs. Being away can interrupt the routines and relationships that make our primary community feel like home. Miss enough dinners, volunteer commitments, or neighborhood gatherings, and we may find ourselves less connected than we intended. Relationships in another place also require more than showing up when it suits our schedule. Friends have their own routines, and a meaningful connection depends on mutual effort. Travel brings costs, logistics, and fatigue. If we own another property, maintenance and management can consume time we hoped to enjoy and add costs. There is also a risk of confusing our affection for a past chapter with how a place fits our lives today. Returning can be rewarding, but we cannot expect a city, or its people, to preserve the life we remember.

This approach requires financial flexibility, though a portfolio of places does not require a portfolio of properties. Renting the same apartment for a few weeks each year, arranging a home exchange, or planning shorter visits during less expensive seasons may make it more attainable. The right arrangement depends on our resources and what we hope to gain. It also depends on our stage of life. A period with fewer work or caregiving obligations may create an opening that will not last forever. That is a reason to consider how we want to use the flexibility we have today, while keeping commitments manageable if our circumstances change.

Should You Consider a Portfolio of Places?

Successful Place Planning includes questioning assumptions about what home must look like. For some of us, choosing a primary home does not mean committing to one place 365 days a year. Recognizing that possibility may help us embrace a place that falls short in some respects but supports much of the life we want. We can meet other desires through intentional, recurring connections elsewhere.

Is there a place you miss, a friendship you want to nurture, or a community you would like to know more deeply? What might it look like to make that place a regular part of your life? If your circumstances allow, consider starting with one extended visit and exploring what a recurring rhythm could offer. The next step in your Place Plan may be giving another meaningful place more room in your life.