The Ultimate Guide: How to Fund Travel with Remote Work and Benefits

How to leverage your remote work position to fund your travel dreams - based on more than four years of living as a digital nomad family with a remote work income

Executive Summary

Remote work isn’t just about working from home, it’s a financial opportunity that can fund your travel dreams and provide a pathway for financial security in your future. After 10 years in online business, with many failed attempts, with a good strategy, and a family, for the past 4.5 years, turned standard remote work benefits into my family’s travel funding machine.

This guide shows you exactly how to:

• Maximize your remote work savings (my strategy that works)
• Leverage company benefits for travel funding (shares, stock options, tools)
• Use Bitcoin DCA with your remote income (my actual strategy)
• Optimize AI productivity to increase earning potential (real results)
• Build a sustainable travel fund while maintaining job security

This is my documented journey from stay at home mum, to failed blogger, to remote working digital nomad family, to travel freedom. Nothing inside this post can be taken as financial advice. When considering investing, make sure to consult with a qualified investment advisor and do plenty of your own research to decide what is best for your and your family.

Why Remote Work Benefits Are Your Travel Funding Secret Weapon

Most people think remote work benefits are just about flexibility and work-life balance. But if you’re strategic, they’re actually a financial goldmine for travel funding.

The Hidden Financial Advantages of Remote Work

1. Geographic Arbitrage Opportunities

• Work from high-paying locations while living in low-cost areas
• My strategy: Remote salary from expensive country, living in affordable destinations
• Real example: $50-65K remote salary goes much further in Vietnam than Sydney, Australia

2. Reduced Living Costs

• You could save hundreds by removing the daily commute
• Lower food costs (cooking vs. eating out) - you could save a lot if you’re going out for coffees and taking out for lunch
• Reduced wardrobe expenses (no office dress code) - I work in my PJs often

3. Tax Optimization Opportunities

Tax opportunities vary significantly depending on citizenship and countries you’re working from. In my case (NZ Citizen), after being out of the country minimum days and having no ties - eg no home ownership, no rental property that I return to, no regular visits - I am a non-resident for tax purposes which means no tax on my worldwide income. However, I need to establish a tax residency.

• International tax benefits for digital nomads - potentially eventually creating a LLC for freelancing, consulting, online business, and there are plenty of options to reduce tax obligations
• Deductions for home office and travel-related expenses
• In some cases, perpetual tourist might suit you, however be prepared for a lifestyle with ever increasing challenges regarding your finances

Note: We will cover tax strategies in another blog post as this varies greatly depending on individual circumstances.

My 5-Point Remote Work Travel Funding Strategy

Strategy 1: Strategic Savings (18-Month Plan)

My Real Numbers:

• Starting point: $0 in travel fund - Mid 2019
• Monthly savings goal: $1,500
• Timeline: 8 months
• Result: < $16,000 travel fund (we also sold everything we owned)

How I Did It:

1. Automated savings - from every paycheck (thanks to my husband as I was at home with the kids)
2. Geographic arbitrage - moved to lower-cost area
3. Lifestyle optimization - cut unnecessary expenses
4. Leveraged spare room - rented our downstairs self-contained unit to a border
5. Side hustle income - attempted various online business setups (worldtravelambitions.com)

Your Action Plan:

• Calculate your current monthly expenses
• Identify 3 areas to reduce spending
• Identify areas you could increase income
• Set up automatic transfers to travel fund
• Track progress monthly

Strategy 2: Bitcoin Dollar-Cost Averaging

My Approach:

• Allocate minimum 10% of remote income to Bitcoin
• Use dollar-cost averaging (DCA) strategy
• Hold for long-term appreciation and lifetime financial security
• Future potential to leverage Bitcoin stack for investment property

Why This Works:

• Reduces volatility risk
• Takes advantage of market dips
• Builds wealth over time
• Provides inflation hedge

Wallet Recommendations:

• Exodus Wallet (easiest for beginners)
• Kraken (for transferring to your local bank account if you need to sell)

Risk Management:

• Never invest more than you can afford to lose
• Diversify beyond just Bitcoin
• Have emergency fund separate from Bitcoin

Important: Learn extensively about Bitcoin before investing. Make decisions from knowledge and understanding rather than gambling.

Strategy 3: Company Benefits Optimization

Stock Options & Shares:

• The company I work for offers RSUs (Restricted Stock Units)
• Used vesting schedule to plan for future wealth acquisition
• Company now publicly listed on NYSE American
• Strategic liquidation opportunities during limited trading windows

Company-Sponsored Tools:

• Leveraged company budget and training for productivity tools - this made me more valuable as an employee and also gave me skills to advance my own projects
• Used Cursor AI to increase efficiency both at work and on side hustles (I purchased my own Cursor and Claude accounts when I realized what I could achieve)
• Saved 30-100 hours per week through AI optimization
• Converting time savings into additional income opportunities

Health & Wellness Benefits:

• Utilize company health insurance for international coverage (or consider SafetyWing Nomad Insurance for comprehensive travel coverage)
• Leverage wellness stipends for travel-related health expenses
• Use mental health benefits to support digital nomad lifestyle

Strategy 4: AI Productivity Optimization

My Cursor AI Experience:

• Increased marketing research and website building efficiency by 40% - I think it’s realistically more than this, but I don’t know how to measure it
• Using these tools could reduce your debugging time by up to 60%
• Enabled faster project research, implementation, completion
• Result: Achieving more than 30-100 hours of work in limited time windows, generally, less than 16 hours a week

ROI Calculation:

• Tool cost: $20/month
• Time saved: >30 hours/week
• Hourly rate: $50
• Monthly value: $6,000
• ROI: >29,000%

Check out this post I wrote: How I Compressed 35 Hours of Work Into 3 Hours - The AI Productivity Breakthrough That Changed Everything

Converting Time Savings to Income:

• Use saved time for freelance work
• Start side hustles with newfound capacity
• Invest in skill development
• Pursue passion projects that could become income streams

Strategy 5: Remote Work Income Optimization

Salary Negotiation Strategies:

• Leveraged remote work flexibility with good pay and great flexibility for hours
• Negotiated cost-of-living adjustments
• Secured performance bonuses tied to remote work productivity
• Result: Consistent salary increases over time

Side Hustle Integration:

• Used flexible schedule for freelance work and family travel
• Leveraging remote work skills for consulting
• Created digital products during downtime
• Potential for $3,000/month additional income

Real Timeline: From Stay at Home Mum, to Remote Worker to Travel Freedom

Foundation Building: 8 months

Months 1-8: Mid 2019 until February 2020

• Started automated savings ($1,500/month)
• Heavily reduced any unnecessary spending
• Leveraged a border in our downstairs apartment ($200 AUD a week)
• Dabbled in some crypto ICO - but felt like riding a rollercoaster so bailed out
• Worked on side hustle projects - worldtravelambitions.com (my first attempt at travel blogging)
• Sold everything we owned for additional savings
• Bought tickets before we actually achieved travel goal
• Reached $12,000 USD travel fund

Travel Family Digital Nomad Life: 16 months

Months 9-25: February 2020 to June 2021

Original Goal:

• One month in New Zealand
• One month in Vietnam
• One month fast travel in SEA
• One month Turkey
• Walk the Camino in Spain
• Monetize worldtravelambitions

Reality:

• One month in New Zealand
• Arrived in Vietnam 6 March 2020
• The world shut down
• Travel blog dream decimated as no one was traveling
• We travelled Vietnam
• We started running low on funds
• Made a poor decision to invest in a crypto investment forex trading thing (total scam)
• Made enough to cover a couple of months living costs, but quickly realized it wasn’t safe
• Saw funds get to critically low
• Applied for an online remote job as a Social Media Support person
• Became a full-time remote worker

Digital Nomad Remote Working Slow Family Travel Around the World: 18 months

Months 26-44: July 2021 to December 2022

• Started saving again - account was at close to $0
• Started DCAing in Bitcoin
• Began to acquire RSUs from the company I work for
• Discovered pregnancy with fourth child
• Vietnam started to change with Covid impacts
• We worried about our visa status going forward
• New Zealand was still closed (even for Citizens due to isolation hotel lottery)
• Asia was mostly closed or extremely expensive to enter
• We rebooked our cancelled flights from 2020 to Turkey
• Started working from travel destinations
• 3 months in Turkey
• 1 month in Crete, Greece
• Moved to Spain to birth our 4th child
• Geo arbitrage in Spain at that time was pretty good
• Remained in Spain until December 2022 due to birth certificate complications
• Ended this period with a good amount of savings and a great supply of RSUs
• Took a hit with some Bitcoin that was saved in Celsius Platform that went bust due to poor management
• Felt more stable with Bitcoin savings (even at the bottom of the market)

Digital Nomad Remote Working Slow Traveling Family Back to Asia: 12 months

Months 44-56: December 2022 to December 2023

• Continued saving in Bitcoin
• Traveled to Bulgaria, back to Phu Quoc, and then Hoi An in Vietnam
• Built a travel tribe of families
• Travel industry and travel blogging niche was not performing well
• Pivoted to try a Master Resell Rights Digital Product opportunity
• Made a bit of money but was very burned out and tired
• Couldn’t maintain full-time work and marketing the new business
• This is when I first launched HowtoFund.travel
• Travel community left Vietnam
• Felt increasingly isolated
• Teens wanted a home base
• Opted to give New Zealand a try since we hadn’t lived there since 2011

Returning to ‘Home’: 10 months

Months 56-66: December 2023 to September 2024

• Had hopes NZ might be a great base
• Hubby got work to help fund the expensive cost of living in New Zealand
• I focused on family and trying side hustles (howtofund.travel)
• Failed miserably
• Read books
• Emotional family stuff
• Realized no one in New Zealand that we love has much time
• People are on the hamster wheel working to pay for house and stuff
• It wasn’t quite what we expected
• Only a few family members came to see us more than once
• We were homesick for the freedom we had as a digital nomad family traveling the world
• May 2024 - Work provided an opportunity to travel to NYC for uplisting to NYSE
• Realized it was time to make an exit plan as we had overstayed and now become tax resident
• Booked a trans-atlantic cruise with friends
• September left on our next adventure

Returning to Remote Working Digital Nomad Slow Traveling Family: 12 months

Months 66-78: September 2024 to currently

• Traveled and remote worked around the world
• Felt like we’ve achieved full time family travel freedom
• Malaysia, Spain, UK, a trans-atlantic cruise including stops in France, the Azores, British Virgin Islands, St Marteen, Antigua and Barbuda, ending in Martinique
• A couple of months in Dominican Republic, Colombia, Panama
• USA for a couple of nights on a layover to Japan, then back to Vietnam
• We realized we love Vietnam
• We learned what we love (freedom, warmth, friendly people, safety, good cost of living and close enough to return to our families or for our families to come to us)
• Learned about AI tools which helped me be more productive in my hours
• With AI’s help, relaunched HowtoFund.Travel

Common Mistakes to Avoid

Mistake 1: Not Automating Savings

• Problem: Relying on manual transfers leads to inconsistency
• Solution: Set up automatic transfers on payday
• My approach: 10% of every paycheck goes directly to Bitcoin

Mistake 2: Investing Too Much in Crypto

• Problem: Putting all savings in volatile assets - don’t touch crypto until you first go deep in your learning about Bitcoin.
• Solution: Diversify across savings, crypto, and traditional investments
• My allocation: Learn extensively about Bitcoin before investing. Make decisions from knowledge and understanding rather than gambling.

Mistake 3: Ignoring Company Benefits

• Problem: Not maximizing available company resources
• Solution: Audit all benefits and negotiate for more
• My gains: Additional $10,000+ in benefits over 18 months

Mistake 4: Not Using AI Tools

• Problem: Working harder instead of smarter
• Solution: Invest in productivity tools that save time and can help you and your team achieve more
• My results: 40% efficiency increase, more time for income generation with side hustles that you can actually research and launch

Tools and Resources You Need

Essential Apps for Remote Work Travel Funding

Savings & Budgeting:

• YNAB (You Need A Budget): $84/year - Popular budgeting app
• Mint: Free - Personal finance management
• Personal Capital: Free - Investment and wealth management

Bitcoin Investment:

• Exodus: Easy for beginners
• Important: Don’t leverage your Bitcoin. Be wary of platforms offering APY on your Bitcoin

Productivity & AI:

• Cursor AI - Code assistance and content creation ($20/month company-sponsored + personal paid account)
• Claude - Research and writing assistance ($20/month)
• ChatGPT - Quick tasks and brainstorming
• Gemini - Google’s AI assistant for research and analysis
• Grammarly - Writing enhancement and grammar checking
• Notion AI - Organization and project management ($8/month)

For a complete guide to 56 AI tools for digital nomads, check out my Top 56 AI Tools in 2025 post.

Travel Planning:

• SafetyWing Insurance: $300/month (for six people)
• Wise (formerly TransferWise): Free
• ING Australia Banking: Free and great for rebates on international conversion and ATM fees
• N26 European Bank: Free European banking for digital nomads
• Revolut: Multi-currency banking and travel card

Recommended Reading

• “The 4-Hour Workweek” by Tim Ferriss
• “Digital Nomad” by Tsugio Makimoto
• “The Psychology of Money” by Morgan Housel

Getting Started: Your 30-Day Action Plan

Week 1: Assessment & Planning

• Calculate current monthly expenses
• Identify 3 areas to reduce spending
• Set up automatic savings transfers
• Research Bitcoin DCA strategy

Week 2: Company Benefits Audit

• Review all available company benefits
• Schedule meeting with HR about additional benefits
• Research stock option vesting schedule
• Identify company-sponsored tools to request

Week 3: AI Productivity Implementation

• Sign up for free version Cursor AI (or similar)
• Create productivity workflow
• Track time savings for 1 week

Week 4: Income Optimization

• Research side hustle opportunities
• Set up freelance profiles
• Create digital product ideas
• Plan salary negotiation strategy

Success Metrics to Track

Financial Metrics

• Monthly savings rate (target: 10-25% of income)
• Travel fund balance (create a target for you and your family)
• Bitcoin portfolio value
• Side hustle income

Productivity Metrics

• Hours saved through AI tools
• Project completion speed
• Income per hour worked
• Work-life balance satisfaction

Travel Readiness Metrics

• Destinations researched
• Budget allocated per destination
• Insurance coverage secured
• Visa requirements understood

Frequently Asked Questions

Conclusion

Remote work benefits are more than just flexibility—they’re your ticket to travel freedom. By implementing these 5 strategies, you can turn your remote position into a travel funding machine.

The key is consistency and strategic thinking. Start with one strategy, master it, then add the next. In 18 months, you could have a $36,000 travel fund and the freedom to work from anywhere.

Remember: This isn’t about getting rich quick. It’s about leveraging your existing remote work benefits to create the lifestyle you want.