Beginner travel series the nomad experiment plans vs backup plans
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Analysis Paralysis? Rigid Plans Are Overrated—BackUp Plans For The Win!

Analysis Paralysis? Rigid Plans Are Overrated—Backup Plans For The Win!

I get it. Especially if you’re not exactly well-practiced at travel, the idea of going on a trip without a real plan seems crazy. I know, since I used to be that guy that would have every single detail of a trip down before I ever got on the plane. A super Nervous Nelly about things outside of my “control,” so I attempted to make sure I had everything planned. (“Control” in quotes there because we all know that the idea of actually controlling things is a bit of a farce.)

But here’s the thing, I’ve actually learned over time that having firm plans can be kind of counterproductive and limiting. Stick with me here, especially if you’re dreaming of diving deeper into travel, changing your job or career, or maybe even going full nomad.

Free your mind up a bit by making loose plans (or goals, or intentions…) and make sure you concentrate more on plenty of comfortable backup plans. 

This little mind shift can really free you up. Especially if you feel handcuffed by fear or uncertainty no matter what area of life you’re talking about. Here are a couple of arguments in favor of lightening up on the plan in favor of having multiple outs. 

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Plans vs. Back-Up Plans And Travel

Unless you’re one of those super planner types that live to plan, simply the idea of filling weeklong travel plans with details might seem daunting. As I mentioned, I used to do this, and I have many friends that are like travel planning ninjas at this. But since I’ve started traveling more, and made long-term travel my current life goal, I’ve realized that planning every moment is really friggin’ exhausting! Of course, that realization does come with a bit of practice and “knowing thyself.”

Here’s the thing—especially if you’re going to a new place—with new languages, customs, food, and so on—having backup plans is a monumentally important factor in how successful your end-view of the excursion will be. The more you get comfortable with the potential alternatives to your main goals, the more comfortable you’ll likely be with all outcomes. 

My current example is that I’m planning for three months in Portugal…having never been…late in the pandemic…over Christmas and New Year…and having not traveled internationally since being diagnosed with Type 1 Diabetes. That’s some heavy shit right there! 

I’ve had friends ask me if I have plans, or if I know where I’m staying, or if I’m renting a car. No, No, and No.


It’s true. As of now, a month before I leave, I have nothing but a flight…and a lot of research and bookmarks and pins dropped of places I might want to visit. I will have my first couple of nights of hostel accommodations booked in Porto, but beyond that, I’ll likely go with the flow and where the wind blows me. Of course, that’s with a general understanding of the country, costs, language, and how easy it is to get around.

But What Happens If Things Go Wrong?

The most important part of all of this is that if shit truly hits the fan with my diabetes, or I implode emotionally, or, or, or—my end-all backup plan is to simply change my return flight. I’m going into this with the reality that I may have to pay the $100 or so fee, cut my trip short, and come back to the states and regroup. This is almost always an option for you too.

The tricky part is swallowing your pride and doing what’s right for you and not allowing outside pressure to dictate for you.

I also always make sure to have travel medical insurance in case of time-sensitive medical issues abroad, and highly recommend you do too.

Plans vs. Back-Up Plans With Job Changes

Another place I like to encourage a bit of a mind-shift is with jobs and careers. Releasing a little bit of the pressure on yourself here can really open you up to new opportunities. It can also be a bit dangerous to ever fall into the idea that you actually have control of your job, career, or means of making a living. We rarely really do. 

First, I suggest making every effort to not live in debt and avoiding that whole keeping up with the Joneses thing. But second, realize that you have options…like lots of options! (This book helped me get out of $50k in debt over 4 years…along with a lot of short-term sacrifices.)

If you’re in your teens or 20s, the sky really is the limit on what directions you could go in and jobs you could take. I highly suggest you explore your options at this age. And if you’re 30+, there’s likely an absolute shitton of things you’ve learned and are more than entry-level at.

Answer me this: If you got fired right now but had to choose a job different than the one you’re doing (like in a totally different industry), what would you choose to do?

Don’t get in the weeds and overthink this question. Just dream, my friend!

That Sounds Scary AF…

Well, yes…yes it does...and yes it is!

But so does waking up in ten years realizing that your life truly hasn’t changed much because you were afraid to take some calculated chances…with perfectly acceptable back-up plans.

READ NEXT: Truth Be Told I’m Scared Sh!tless I Have No Idea What I’m Doing…

In the past few years, I’ve completely gotten rid of my income stream to then rebuild towards clients that understood I will be working from anywhere in the world. I spent a year watching my (meager) savings dry up to do that. During that time…and now…the constant thing I tell myself is that I know I have the skills to get a job to at least pay the bills. And because I live minimally, that doesn’t have to be a high-paying job. 

Yes, I would prefer to make enough money to put some in the bank, but if I have to pause that goal for 6-months or a year, it shouldn’t be the end of the world. These ideas are my backup plan so far as income goes. The mind shift allows me to explore what I really want to do instead of what society tricks me into thinking is what I have to do. Things like taking a few months to write and design a book, which I likely would have never done in my old default life…mostly because I wouldn’t have had (read: chose to prioritize) the time. 

Plans vs Backup Plans…And The Experiment Mindset

This all comes back to the whole experiment mindset. Not viewing each idea or move in your life through a black-and-white, right or wrong kind of lens. That mindset is extremely limiting. Thinking of each move you make as more of an experiment really does start to free you a bit of the pressure that comes with the need to be exacting or committal. 

And yes, I understand that we’re talking semantics here. Even choosing not to have a plan is kind of a plan in and of itself. But you might just find that your load is lightened a bit, and your ability to pull the trigger on some bigger life changes is increased, if you choose to put less pressure on a rigid plan and put more of your efforts into the “what if that doesn’t work,” back-up plans.

If you’re OK with those, then what’s holding you back? 

Cheers friend! 


BTW. If you’re not yet, I would love it if you followed over on Instagram, where I put shorter thoughts to pictures from my travel. 

Travel Planning Tips

Figure out where you are going & how are you getting there…
I suggest using at least 2 to 3 different travel search sites. Start with Skyscanner or Orbitz or Booking …or whatever aggregator site you prefer. Then when you see what airlines to use, check their respective sites for better deals or rewards flights.

Figure out where you’re going to stay…
If you’re interested in hostels, search Hostelworld or Hostelling International. For longer-term or more private digs, look at Airbnb, VRBO, or you can look for hotel rooms in the links from the search engines listed above. 

Get comprehensive travel insurance, or in the least, travel medical insurance if internationally…
Especially with Covid not going anywhere, get covered. Start with an insurance aggregator like Insure My Trip, or with SafetyWing, World Nomads, or another. Then decide what is important to you; trip cancellation, baggage coverage, medical, or all of the above. And get a yearly evacuation plan, since you’ll have to get home after your emergency! 

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