Why We Got Annual Disney Passes Before Leaving Orlando

Today is our 26th anniversary. Sarah and I got annual Disney passes — just the two of us.

Not as a flex. Not as a random splurge. As an intentional decision for our last year with a permanent Orlando home — a way to soak up the backyard we have lived next to for more than a decade, build memories together, gather content, practice travel-ready living, and actually use a membership instead of collecting another one we ignore.

We are aiming for no permanent home starting around April 1. I have written about that redesign in What We're Changing So We Can Work From Anywhere. This post is the other side of the coin: before we leave Orlando, we are going to live Orlando — and this season of park days is for us as a couple.

Why annual passes made sense now

Twenty-six years with Sarah is worth celebrating with something we will share, not something that sits in a drawer. Annual passes turn “we should go more” into a calendar habit.

Our kids are in different seasons now — one out of college, one in college, and a senior in high school. Over our 10+ years in Orlando we have done Disney as a family a couple of times. Those trips mattered. This pass run is not that. This time is dates, evenings, and us time before the home base changes.

They also pass the life-audit test. In Do a Life Audit Before You Go Location Independent, I argued that memberships only count if you use them. A gym you never visit is a donation. A Disney pass we actually use is a season of dates, creative fuel, and showing up for the marriage on purpose.

Timing matters. Leaving a home base makes local magic feel urgent. We did not want our last Orlando chapter to be only decluttering, paperwork, and logistics. We wanted fireworks, rope drop, afternoon snacks, and nights that remind us why we stayed here so long.

Our last year in Orlando is a season, not a countdown

It is easy to treat the exit date like a threat. Pack. Sell. Cancel. Rush.

We are trying a different posture: soak it up. Walk the parks. Take each other. Notice the weather, the crowds, the little rituals. Practice being present while the businesses still have to run.

Location independence is not a rejection of Central Florida. It is a redesign of how home works. Relationships here still matter. The zip code is what changes. That same relationship-first mindset shows up in how we build companies, and I wrote about it in Why Relationship-First Businesses Beat Transactional Ones. Marriage gets the same rule: the relationship is the backbone. The calendar should prove it.

What using the passes actually looks like

Dates and vibes

Some visits will be anniversary energy: slower, less optimized, more “us.” Some will be short evenings after work. Some will be full park days. The point is access without forcing every trip to be a vacation production.

Living near Disney means we can leave when the vibe dies. That is a local luxury tourists do not get. We plan to use it.

We have done the family parks — this is different

Over a decade-plus in Orlando, we have already gotten the family park days. Those memories are real. This season is not a redo of that chapter. The kids are not on these passes. Sarah and I are.

That clarity matters. It keeps the gift from turning into logistics for five people and lets us protect slower, couple-first days. Live first. Capture second. No algorithm required.

Working from Disney’s gravity

I am not pretending I will close deals on Space Mountain. I am saying Orlando’s tourist gravity is a useful rehearsal for portable work.

• Early park time, then calls from a quieter spot
• Laptop blocks near the area without needing a full office
• Practicing focus when the environment is loud and changing
• Proving the business can move even when the day is not a normal desk day

That is the same muscle we need when wifi is weak in another city. Practice while the house still exists as a backup.

Content without killing the gift

We will capture some of it. Photos. Short clips. Notes. Real moments. Content for Knup storytelling, for Ideal Homeschool, and for the real estate lifestyle side.

We will also protect no-content days. If every ride becomes a shoot, the anniversary gift turns into a job. The rule is simple: live first, capture second, publish only what still feels honest.

Ideal Homeschool: content from a different season

This lane is Sarah’s world — and a big part of how she builds for parents.

Ideal Homeschool is not theoretical for us. We have lived flexible learning, family rhythms, and the reality that education is not only a desk. Past family park trips already taught us that Disney can be science, history, storytelling, patience, maps, cultures, and food if you show up curious.

This pass season is not about bringing the kids for field-trip days. It is adult time — and still useful for Sarah’s working plan. Observing how families move through a loud public “classroom,” noting what parents actually struggle with, and turning years of experience into parent-friendly content without turning our dates into a worksheet marathon.

Practical ways that shows up:

• Capture notes and stories she can use for Ideal Homeschool content
• Draw on past family Disney trips without forcing a new kid-centered pass plan
• Pay attention to pacing, energy, and flexible learning themes parents care about
• Practice portable work and creative rhythms before we are fully on the road
• Protect couple time so “content for the brand” never outruns the gift

When we leave a permanent home, learning and content creation on the move get more real. Using Orlando’s biggest stage now still helps — even when the passes are for us two. You can explore the venture side of that work at Ideal Homeschool on Knup.

Travel learning with a house still behind us

Annual passes are travel practice with training wheels.

• Planning without over-planning
• Budgets for food, parking, and extras
• Weather and crowd pivots
• Energy management across a long day
• Saying no when we are done

Those skills transfer. Airports, new cities, long travel days, and couple logistics all reward the same calm. If we cannot pace a park day well, we will not magically pace location independence well.

The realtor lens: living Orlando while we still can

I got my Florida real estate license because people kept asking for help and I kept sending them somewhere else. That story is in How to Get Your Florida Real Estate License. Living here — really living here — makes that work better.

Buyers and relocators do not only ask about bedrooms. They ask what weekends feel like. How close the parks feel in real life. What traffic does to a Tuesday. Whether “near Disney” is a dream or a daily reality. You answer those questions differently when you have annual passes and a local calendar, not only a map.

That local texture is hard to fake from a brochure. It shows up in small details: how early you leave for a park day, which corridors feel convenient versus crowded, what “living near the tourism core” means for groceries, schools, and quiet nights. Those details make better client conversations and better content for people considering Central Florida.

So yes, some of this season will feed the real estate side:

• Lifestyle content about living in and around Orlando
• Honest notes for people relocating to Orlando
• Better conversations with families who want Central Florida for jobs, weather, parks, and schools
• Proof that local knowledge is earned by presence, not just listings

Boundary: not every park day is a client appointment. Presence builds trust. Pressure kills it. If you are buying, selling, or moving to Central Florida, start at the real estate hub or real estate discovery.

How this fits the businesses we are building

Knup stays systems and growth. Ideal Homeschool stays family education and parent-friendly guidance. Real estate stays Central Florida moves and homes. The passes sit underneath as life infrastructure for Sarah and me:

• Calendar blocks that protect marriage and us time
• A content library of real Florida living
• Creative fuel without inventing a fake “Disney brand”
• A reminder that portable businesses still need human seasons

The CRM and follow-up still have to work when we are in the parks. Tools do not replace presence. They protect the work so presence is possible — the same idea behind helpful follow-up in How to Follow Up With Leads Without Being Annoying.

Rules so the passes do not become clutter

• Use them on purpose, not only on perfect Saturdays
• Protect some no-phone, no-content days
• Budget the hidden costs so the passes do not feel stressful
• Keep Ideal Homeschool content honest without turning dates into shoots
• Do a quarterly check: are we using them, or paying for a story we tell ourselves?

If we stop using them, we will say so. That honesty is part of the life audit mindset.

Final thoughts

We got annual Disney passes for our 26th anniversary because we are still here, still together, and still choosing to live the city before we redesign home. Just us two this time — after years of family park memories already banked.

Last year in Orlando should not only be logistics. It should be dates, work practice, content that tells the truth, Ideal Homeschool fuel for Sarah’s lane, and a realtor’s feet on local ground.

Soak it up. Then go.