Comfortably Uncertain

Tag: freedom

  • 20 Questions to Ask Yourself Before Moving Abroad

    20 Questions to Ask Yourself Before Moving Abroad

    Everyone romanticizes the idea of moving abroad.

    Cheaper rent. Slower mornings. Beautiful weather. A fresh start somewhere far away from the life you built before.

    But the truth is that moving abroad isn’t just a travel decision — it’s a life design decision.

    And the people who thrive after moving are usually the ones who ask themselves a few uncomfortable questions before they ever buy the plane ticket.

    If you’re seriously considering living abroad, here are twenty questions worth sitting with first.

    The 10 Questions

    1. Do I want to move, or do I just need a vacation?

    Sometimes the urge to leave everything behind is really just a sign that you’re burned out.

    A long break, a change of scenery, or a slower season of life can solve a lot of things that relocation won’t.

    2. Can I realistically be away from family and close friends for extended periods of time?

    Distance changes relationships.

    Even with video calls and messaging, living abroad often means missing birthdays, holidays, and everyday moments.

    Some people handle that easily. Others find it much harder than they expected.

    3. Can I legally and sustainably work in my new country?

    This is one of the most practical questions — and one of the most overlooked.

    Understand your visa options, remote work situation, and whether your income will realistically support the lifestyle you’re envisioning.

    4. Does my new country have the infrastructure I require?

    Things like internet reliability, healthcare quality, transportation systems, and access to everyday services can vary dramatically between places.

    What feels normal where you live now may look very different somewhere else.

    5. Am I ready to adapt to a new culture, customs, and traditions?

    Living somewhere is very different from visiting.

    Things will be done differently — and that’s part of the experience.

    The question is whether you’re excited to learn those differences or frustrated by them.

    6. What am I hoping this move will change about my life?

    People often move abroad hoping for a slower, more intentional life.

    That can absolutely happen — but it’s worth understanding what you expect to be different.

    7. What happens if those things don’t change right away — or at all?

    Sometimes life abroad looks surprisingly similar to life at home.

    You still work. You still have responsibilities. You still have ordinary days.

    Being realistic about that makes the transition much easier.

    8. How do I handle uncertainty, inconvenience, and things not going as planned?

    New countries mean new systems.

    Banking, paperwork, housing, and government processes can sometimes be slower or more confusing than you’re used to.

    Patience goes a long way.

    9. Am I comfortable feeling like an outsider for a while?

    Even in welcoming places, it takes time to feel like you belong.

    You might not understand every cultural reference, social norm, or conversation right away.

    That’s a normal part of the process.

    10. How important is convenience to me in my daily life?

    Some countries offer incredible quality of life but less convenience.

    Things may take longer. Systems may be less streamlined.

    For some people, that trade-off feels completely worth it.

    11. Can I slow down without feeling anxious, unproductive, or behind?

    A slower lifestyle can be wonderful — but it can also feel uncomfortable at first if you’re used to constant productivity.

    Learning how to enjoy a different pace takes time.

    12. What parts of my identity are tied to where I currently live?

    Where you live often shapes who you are.

    Your job, routines, friendships, and social environment all contribute to your sense of identity.

    Moving can shift that in ways you may not expect.

    13. How do I respond when familiar routines and structure disappear?

    One of the biggest adjustments abroad is rebuilding everyday structure.

    New grocery stores. New routes. New habits.

    Some people thrive in that process. Others struggle without familiar routines.

    14. What trade-offs am I willing to accept — and which ones would eventually feel like dealbreakers?

    Every lifestyle comes with trade-offs.

    Living abroad may mean giving up certain conveniences while gaining other things that matter more.

    Being honest about your limits helps prevent long-term frustration.

    15. How adaptable am I when systems are inefficient or unclear?

    Not every place runs as smoothly as the systems you might be used to.

    Sometimes things take longer. Sometimes instructions are unclear.

    Adaptability is one of the most valuable traits for people living abroad.

    16. How do I build community, and am I willing to start from scratch?

    Building meaningful relationships takes time anywhere.

    When you move abroad, you’re often starting that process all over again.

    Understanding how you build friendships can make the transition much easier.

    17. What role does work play in my sense of purpose and stability?

    For many people, work provides structure, identity, and stability.

    If your move changes your relationship with work, it’s worth thinking about how that might affect your sense of purpose.

    18. How does my nervous system respond to new environments and stimulation?

    New languages, sounds, cultural norms, and routines can feel exciting — but also overwhelming.

    Some people thrive in new environments. Others need more time to adjust.

    19. Am I moving toward something meaningful — or away from something uncomfortable?

    Moving abroad works best when it’s part of a larger vision for your life.

    Escaping discomfort rarely solves the deeper issue.

    Building toward something meaningful usually does.

    20. If this move ends up being temporary, would it still feel worthwhile?

    Not every move abroad lasts forever.

    But even a few years in another country can reshape how you see the world.

    If the experience itself feels meaningful, the timeline matters less.

  • Why I’ll Never “Return to Office”

    Why I’ll Never “Return to Office”

    In October 2017 I was back in the office having a very important meeting with my manager. My four-month-old daughter was in the care of a co-worker. That lasted about twenty minutes before she realized I was nowhere to be found and started screaming so loudly I could hear her from ten doors down.

    That moment was clarifying.

    Earlier that year, in June, I had given birth to my daughter, Emilia. I had what most Americans would call a generous maternity leave. I fully intended to return to work, find a nearby daycare, and settle into the rhythm so many families follow.

    It took one daycare tour for me to realize I couldn’t do it.

    At the same time, my mom had just retired and was planning her move to Arizona. She was the only person I felt completely comfortable leaving Emilia with. We are close — the kind of close where a move across the country feels like an amputation. The thought of her leaving, and me staying behind, felt impossible.

    So there I was. Sitting in a private office with my manager, an HR team member, and my infant daughter.

    Earlier that month I had taken a risk and submitted a request to work remotely. Our plan was simple in theory and terrifying in practice: follow my mom to Arizona. My husband would quit his job to care for Emilia full-time. I would work from home.

    This was 2017.

    Remote work wasn’t mainstream yet. I would be the first person on my U.S. team to go fully remote. But our company had global offices. We were already dialing into international meetings at odd hours. The infrastructure existed — it just wasn’t common.

    My request was approved.

    On January 27, 2018, Emilia and I boarded a flight from SeaTac to Phoenix. Jorge drove a moving truck packed with everything we owned. We didn’t know exactly what we were building — we just knew we were choosing our family first.

    I haven’t worked in an office since.

    Over the years I’ve had roles that required occasional travel. I’ve worked with teammates I’ve never met in person. Entire projects have been built through Slack threads and video calls. This is the era we live in.

    And remote work is the reason for everything that followed.

    It allowed us to move from state to state while we figured out where we wanted to plant roots. It gave us the flexibility to experiment with lifestyle instead of defaulting to geography. It eventually made our move to Mexico possible.

    Remote work is not just a location change. It’s leverage.

    When I think back to my early career, I remember the commute. The rigid schedule. The unspoken rule that productivity equaled physical presence. Eight hours in a chair whether the work took four or twelve. Time measured by badge swipes and fluorescent lighting.

    I gained those hours back.

    I gained mornings at home. Midday walks. Doctor’s appointments that didn’t require half a vacation day. I gained the ability to design my day around output instead of optics.

    I also stopped getting sick every other month. Offices are a breeding ground for shared germs, recycled air, and exhaustion cycles. Removing myself from that environment changed my health in ways I didn’t expect.

    And financially? The impact was significant.

    No daily commuting costs. No professional wardrobe churn. No convenience spending because I was too tired to cook. Fewer impulse purchases tied to corporate life. Remote work quietly increased our margins.

    Over time, those margins compounded.

    The most important shift, though, wasn’t logistical or financial.

    It was psychological.

    I stopped tying my value to a building. I stopped believing I needed to be seen to be effective. I started evaluating work based on results, not residency.

    That one request in 2017 reshaped the trajectory of my life.

    If you are sitting in an office right now feeling the tension between the life you want and the structure you’re operating inside, I understand it deeply. I was there. I made the ask before it was popular. I built the case. I took the risk.

    Remote work gave me the freedom to design our life intentionally.

    It can do the same for you — if you’re willing to ask differently.