Why "Someday" is the Most Dangerous Word in Your Vocabulary
- Jennifer Sontag
- 1 hour ago
- 3 min read
We all have a "Someday."

For you, maybe it looks like a stone farmhouse in Tuscany with a view of the vineyards. Maybe it’s a modern apartment in Valencia, steps from the sea. It’s a beautiful place to visit in your mind when your current reality feels gray, stressful, or stagnant.
"Someday," you tell yourself, "I will move there. Someday, when the timing is perfect. Someday, when I’ve done enough research."
But here is the hard truth we see every day at ViaMonde: "Someday" is a trap. It feels safe, but it is actually the biggest risk you can take.
While you are waiting for the stars to align, the world is moving. Laws change. Income requirements shift. Borders tighten. The "perfect time" doesn't exist—but the right time is usually right now.
Here is why waiting is costing you more than you think, and how real people are bypassing the "perfect" plan to get to their dream life today.
The Myth of the Straight Line
Many clients come to us with a rigid plan. They have researched one specific visa, for one specific town, based on a blog post they read three years ago. But immigration is a living, breathing thing. It changes.
Just today, I am heading to the airport to pick up a couple moving to Terrasini to join our growing expat community. Their journey is the perfect example of why you need a strategist, not just a checklist.
They were on the brink of resigning from their jobs and boarding a plane, banking on Citizenship by Descent, when the laws suddenly changed and blocked their path. They were stuck. Because they hadn't left their jobs yet, they couldn't show the months of "passive income history" that the Italian Elective Residence Visa (ERV) usually demands.
We looked at Spain—where the Non-Lucrative Visa is often more straightforward. But after looking at homes and communities there, they kept coming back to their original dream: Italy.
So, we didn't settle for the easier option. We went to work on the harder one.
We prepared an ERV application that went far above and beyond the standard requirements. We used current approval data to build a flawless financial package and conducted rigorous interview prep. The result? They were granted their visas in weeks, despite not having those standard income disbursements yet.
Today, instead of being stuck in their old office, they are moving into a beautiful apartment with rooftop views over the sea—and yes, their dogs are coming too.
The Power of "The Narrative"
Another trap people fall into is letting social media fear-mongering paralyze them.
I am also welcoming a self-employed client to Palermo today. She was terrified by the stories of rejection for the Digital Nomad Visa she saw online. She has a complex life and a pending 1948 Citizenship case, and she didn't know if she could make the move now.
We worked together daily to silence the noise. We didn't just submit "proof of income." We built a case.
We included contracts showing continued income, a history of professional success, and a detailed budget for her new life in Palermo. Crucially, we wrote a strong Cover Letter articulating her connections to Sicily, her goals, and her clear intentions for living here.
It is these extra steps—the narrative, the context, the human element—that ensure our clients are approved when others are rejected. She isn’t pausing her life for bureaucracy; she made the bureaucracy work for her life.
The Hidden Cost of Waiting: Real Estate
Sometimes, "Someday" happens because you feel stuck on where to go. But while you wait, the market is moving.
Maybe the wait isn't to move physically yet, but to move forward with the investment or vacation home. Prices continue to go up because the markets are strong in Italy and in Spain (which also boasts a growing economy).
"Someday" doesn't just cost you time; it costs you equity. Whether you are looking for a primary residence or a vacation investment, the best time to enter these strong markets is before the secret gets further out.
The Decision
If you look back at yourself one year ago, did you want to move then? Are you any closer today?
"Someday" protects you from the fear of rejection, but it guarantees the pain of regret. The clients landing at the airport today aren't fearless. They were nervous about the paperwork. They were worried about leaving friends. They had doubts.
But they decided that their new life was worth more than their old comfort.
Don't let another year dissolve into "research." You don't need to know all the answers. You just need a team that does.
Let's turn your "Someday" into a date on the calendar.
Let’s review your options for Italy and Spain.
