How to Escape the Office: Convince Your Boss to Let You Work & Travel

How to Convince Your Employer to Let You Work Remotely (And Travel)

You've been dreaming about it for months, maybe years. Working from a café in Barcelona, taking client calls from a beachside coworking space in Bali, finishing projects while watching the sunset over Prague Castle. The digital nomad lifestyle isn't just for freelancers and entrepreneurs anymore. Thousands of employees are successfully working remotely while traveling, and you can too.

I've seen this conversation go both brilliantly and disastrously. The difference usually comes down to preparation, timing, and how you frame the proposition. Your employer isn't thinking about your wanderlust, they're thinking about productivity, reliability, and whether this arrangement will create more problems than it solves. Your job is to make saying "yes" the obvious choice.

Let me walk you through exactly how to secure remote work approval from your employer.

Phase 1: Laying the Groundwork for Remote Work Approval

The worst time to ask about working remotely and traveling internationally is during your first week or right after missing a deadline. Timing and track record matter enormously.

Build Your Track Record and Trust

Credibility First: You need to be the employee your manager trusts implicitly, the person who delivers quality work on time, communicates proactively, and doesn't require constant oversight.

Establish Tenure: Ideally, you've been with the company at least six months to a year. You need clear examples of successfully completed projects and positive feedback.

Test the Waters with Trial Remote Work: Before proposing full-time international remote work, try working from home one or two days per week. This proves you can stay productive outside the office. Document your productivity during these trial periods, you'll need this data later.

Know Your Company: Research if your organization has existing remote worker policies or if others have successfully negotiated flexible arrangements. Pioneering new territory requires a more robust proposal.

Phase 2: Crafting the Remote Work Business Proposal

Here's where most people fail: they lead with their own desires. Your manager doesn't care that you want to travel; they care about business outcomes.

Frame Your Request as a Company Benefit

Your proposal must answer one central question: "How does this arrangement benefit the company?"

Increased Productivity: Cite studies that show remote employees are often more productive. Without commute time or office distractions, you can focus more deeply on tasks.

Extended Work Coverage: If you travel across time zones (e.g., working from Europe while the team is in the US), you can provide coverage during previously non-staffed hours, benefiting international clients.

Cost Savings & Retention: Remind them it’s cheaper to accommodate a strong performer's request than to lose you and pay for recruitment and training. This is a critical employee retention strategy.

Talent Competitiveness: By proving flexible work succeeds, you help your company attract and retain top talent who prioritize flexibility.

Proactively Address Manager Concerns

Don't wait for your employer to object, anticipate problems and provide solutions in your initial document.

If the concern is Communication and Responsiveness, your proactive solution will be to inform your boss in detail about specific tools (Slack, Zoom) and your core availability hours. Commit to overcommunication during a trial period.

If he/she is more concern about Collaboration and Meetings, you can propose regular video check-ins and detail how you’ll participate in team meetings using virtual tools.

If you are considering to go to a different Time Zone and this is the main issue, specify how much overlap you will maintain with the home office (e.g., "I will shift my schedule to overlap 4 hours with EST").

If the main concern is Security & Compliance, you can address data security, mandatory VPN usage, and commitment to researching local visa and tax implications before arrival.

If the main issue is more about Performance Measurement, propose clear, measurable metrics (KPIs) to evaluate your success objectively, removing any ambiguity.

Phase 3: The Conversation and Negotiation

You've built credibility and crafted a proposal. Now, focus on professionalism and flexibility.

1. Request a Formal Meeting: Schedule dedicated time (30–45 minutes). Do not ambush your manager. Give them a heads-up about the topic.

2. Bring a Written Proposal: A two-to-three-page professional document shows you are serious and gives your manager something to present to HR. Include an executive summary, benefits, and proposed success metrics.

3. Lead with Gratitude: Acknowledge your commitment to the company and frame the request as a win-win for long-term contribution, not a personal favor.

4. Propose a Trial Period: If there is hesitation, suggest a defined trial (3 or 6 months) with clear weekly check-in points. This significantly reduces your employer's perceived risk and provides objective criteria for success.

What If They Say No? Finding a Remote-First Job

If your employer won't agree to let you work remotely while traveling, don't burn bridges. Your goal now shifts to finding a flexible employer or switching your career path.

The Internal Strategy

Understand why and ask for specific reasons: if it's policy, ask what would need to change for them to feel comfortable in the future, establishing a roadmap for the next review. Be flexible and always consider a compromise, ask about middle-ground options such as extended unpaid leave, a short-term contractor relationship, or a limited one-month remote trial.

The External Strategy (Switching Jobs)

If remote work is non-negotiable for your digital nomad lifestyle, it's time to target organizations that are built for it. I would start by target remote-first employers: look for companies that hire remote workers by default. These organizations already have the necessary systems, culture, and communication practices in place. I would recommend to use specialized job boards to focus your search on platforms like FlexJobs, filtering specifically for fully location-independent positions. You can also contact me directly to book a strategy call, I’ll provide expert guidance to help you make it happen (Work & Thrive Remotely Plan)

Phase 4: Success & Sustainability as a Remote Employee

You convinced them! Now, you must prove this arrangement is better than the alternative.

Get It in Writing: Formalize the arrangement with HR. Document start date, duration (if trial), expected work hours, communication protocols, and performance criteria.

Overdeliver: Be hyper-responsive and exceed deadlines, especially in the first three months. You are setting the precedent for all future digital nomad employees.

Maintain Routines: Set clear work hours and create a dedicated workspace (even in Airbnbs). Avoid burnout by separating work from travel time.

Address International Complexities: Research digital nomad visas (e.g., Portugal, Croatia) before you travel. Consult an international tax professional to understand implications for your pay and residency. Secure international health insurance, as your employer’s plan may not cover you abroad.

You're not asking for special treatment. You're proposing a modern work arrangement that benefits everyone involved. The conversation might feel daunting, but with preparation, professionalism, and a clear value proposition, you can successfully become a remote employee traveling the world.