Create Your Oh Sh*t Contingency Plan & Be Ready When Life Goes Sideways
What’s your plan for when things inevitably go off track? This week, we dive into contingency planning, along with a peek at our ongoing remote business experiment and recommended reads & resources.
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Not to be dramatic, but things will go wrong. A location-independent life isn’t all spectacular sunsets and delicious street food. What’s your plan for when things go sideways?
A good “Oh sh*t” contingency plan isn’t complicated. It’s a simple, quick-reference blueprint for what you’ll do when (not if) something major goes sideways.
Start by asking yourself:
What’s my backup income source if my main gig disappears?
If I had to leave this country in 30 days, where would I go next?
Do I know how to access local healthcare or get emergency care abroad?
If my laptop died tomorrow, how fast could I get back up and running?
These aren’t fun questions, but answering them now means less panic and more clarity later. You’re not trying to eliminate risk; just outsmart it.
For example, I make sure my travel insurance includes device coverage for my laptop and phone, as these are my non-negotiables for remote work. I have a backup eSIM in case the Wi-Fi drops. I’ve mapped out where I’d need to go for care if my blood disorder acts up. Even chronic health issues don’t have to hold you back, but you do need a plan.
And when it comes to flights, I only book non-refundable tickets if the deal is so good I could afford to lose it and buy a new one. Otherwise, I want the freedom to rebook and bail if a location isn’t working out.
Listen, healthy optimism is great… blind optimism, not so much. Be real about what you’re planning and what could go wrong, and you’ll be in a much better place to take a risk.
Take 30 minutes this week to write out the worst-case scenarios for your next steps, and your immediate responses. Don’t worry about having every answer; you can explore your options and add more detail as you ruminate on the possibilities.
Even a rough plan gives you an edge when life throws a curveball.
Update: First Steps in Our Remote Business Experiment
Last week, I promised that Trevor and I would share our progress as we build a new income stream. It’s an experiment, and it might fail spectacularly. That’s okay.
As he inches ever-closer to retirement from his very location-dependent career, it’s time to build something completely remote-friendly to take him into his next phase — which is traveling (more) with his lovely wife.
So, here’s what we’ve done so far:
Bought the domain
Set up a new Substack publication
Connected that publication to the new domain, and to my company’s Stripe account
Designed a logo and created a brand kit for it in Canva
Set up a new Gmail account
Used that email address to set up a new YouTube channel and claim our name
Set up an open Facebook Group to establish a presence there
So far, total investment is our time + around $25 for the domain. Canva Pro is around $150 CDN per year, if you wanted use of all features, or you may have another design tool you prefer. You may have zero design skills and need to outsource that part, which would require an investment that way, instead.
At this point, you might also grab your handle on Instagram, TikTok, or any other social networks you plan to use. We didn’t bother with a Facebook Page as the reach has become so abysmal in recent years, and groups are more interactive and fun anyway.
Now, we didn’t have to set up a brand new business entity for this. That means no new corporation, no business licensing or registration. That’s because this new publication is an allowed business activity inside my existing Estonian corporation, which I set up in 2021 thanks to Estonia’s e-Residency program.
In fact, many different income streams can exist within that business type… books and blogs, contract services, online sources, real-world workshops, and more.
So that’s where we’re at so far! Depending on how much progress we make and how quickly, I hope to bring you an actual name and URL you can check out soon.
If you’ve been considering starting an online business of your own but unsure where to start or how to even approach it, I hope this helps. Even if your business concept is entirely different, you’ll at least find some helpful perspective and tips — and maybe a confidence boost, too.
Now, on to recommended resources… here are a few great reads I’ve stumbled across this past week, plus a tip for making the most of an AI travel coach:
🌍 Why Midlife Nomads Should Embrace the Language Barrier
Brian Clark’s latest shares why learning a new language shouldn't scare you off from relocating abroad — it should inspire you. From his base in Cerritos Beach, Mexico, he argues that midlife is actually the perfect time to take on the challenge. Beyond opening doors to affordable, welcoming destinations like Mexico and Spain, learning a language boosts brain health, expands your worldview, and may even pad your wallet.
👉🏼 Read Why You Should Insist on Learning a New Language on Futher: Live Long & Prosper
📰 How to Avoid Being an “Ugly American” Abroad
In this article, Elizabeth Silleck La Rue offers a timely and necessary guide for Estadounidenses seeking to live abroad without replicating the same extractive behaviors that drove them to leave. From respecting local laws and learning the language to minimizing your environmental and economic footprint, her nine-point checklist is a must-read for anyone serious about ethical emigration.
👉🏼 Read How To Avoid Being an ‘Ugly American on The Conscientious Emigrant
Jenna Park is Embracing Her “Granny Hike” Era
In her beautifully reflective piece If Not Now, When?, Jenna Park captures the vulnerability and courage of midlife travel after chronic health setbacks. With gentle humor and heartfelt honesty, she invites us into her “granny hike” era—where the trails are shorter, but the meaning runs deep. A reminder that adventure doesn’t end when your energy shifts; it simply evolves.
👉🏼 Read If Not Now, When? on Everything is Liminal
🧰 Tool Tip of the Week: Make Your AI Travel Coach Smarter
Before you open the AI Travel Coach, jot down your top 3 non-negotiables — the things you must have in your next destination (think: LGBTQ+ rights, affordable healthcare, visa access, walkability). These priorities will help the AI give you way better, more relevant results. Use the workbook to rate how potential destinations stack up on what matters most to you — not what travel influencers say is trending.
For just €9, you’ll get a dynamic workbook and access to a custom-built AI coach that helps you pinpoint where to go based on your values, budget, and lifestyle — not someone else’s top 10 list.
👉🏼 Get it in Midlife Nomads Academy
That’s it for this week! If you’re comfortable sharing, I’d love to know: Have you ever had to put your “oh sh*t” plan for travel or remote work into action? How did it go?
✌🏻 Miranda
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These are such good questions! And ones I've thought about very often. With our ages and our economy, I think everyone should always have contingency plans. Also, your remote business experiment journey sounds very familiar to something we started a year ago. Good luck!
Thanks for the plug! Good advice here on planning. I'll also note that it's becoming increasingly apparent that moving for purely selfish reasons and without a Conscientious Emigration™ approach and ethic can land one in hot water. Case in point: https://theconscientiousemigrant.substack.com/p/becoming-a-maga-loving-expat-in-russia