How to plan when you hate planning

When you decide to quit your job and jaunt around the world for 3 (plus?) months with no job security on the horizon, you need at least SOME framework to prevent major problems.

And I define major problems from a very macro-lens.

Major problems include unwanted unemployment, bankruptcy, severe illness, and yep, death. (Regardless of your values, I think we can all agree that death is a major problem).

To give you a point of comparison, minor problems include $20 being stolen from your bag, forgetting an article of clothing that you should have brought, and missing an Instagram photo opportunity.

This is undoubtedly a spectrum with some grey area. It would be a buzz kill and extreme inconvenience to lose your passport, but we could all get through it by going to the nearest embassy for temporary documents. The major problems are labeled such because they could literally ruin the rest of your life. Especially death. So, I think it is very important for those of us who like to go with the flow to at the very least plan for the major problems.

 

Major Problem Number One: Unwanted Unemployment

In order to sustain my life upon return—in addition to preventing Major Problem Number Two—I will need a job. I am very fortunate that the jobs I intend to seek are plentiful and if you demonstrate decent people and listening skills, obtainable.

Regardless of what you're looking for, I do think there are some basic “good steps” to combat Major Problem Number One. I really tried to ease the burden on my boss by giving her substantial time to find my replacement. Frankly, we’re all very replaceable in corporate America, but I definitely don’t want them remembering me for the wrong reasons. That could definitely prolong Major Problem Number One on top of instilling some unwanted guilt.

According to this smart lady and iRelaunch founder, Carol Cohen, you also need to let people know that you are looking. I’m gone for no time at all, but I am now actually responding to recruiters on LinkedIn, reaching back out to past references, talking to mentors, asking friends about their companies, and purely absorbing any and all information I can receive on any path that is even remotely interesting (Readers??). People now know that my funemployment is only temporary.

Major Problem Number Two: Bankruptcy

I just dropped a good chunk of change on some flights. And that’s only a portion of my expenses. I still have to pay for hostels, food, activities, taxis and transportation, events, laundry, health insurance, and all the other unforeseen expenses (unfortunately shit happens) that I can’t even anticipate. My bank account is now going only one direction.

That is scary.

The least I can do is make sure it moves predictably and slowly. Current ways that I am trying to control its rate of diminishment include:

1. Find a subletter - I still have a lease. Thankfully, there are plenty of people going in and out of Boston (especially in the summer) who are willing to sublet for a few months. I cut it very close with finding a subletter, so am eating about $150/month. Womp womp. But, it’s better than losing an entire three months of rent.
2. Cut the unnecessary subscriptions - I froze my membership at my gym and cut the Amazon Prime membership. I absolutely refuse to part with my Spotify Premium account (definitely one of the top purchases I made in 2016), but if worst comes to worst, I could close my eyes and delegate someone to click “unsubscribe.”
3. Stock Pile - I’m now feasting off my savings and checking accounts. I want to return to at least enough money to survive for 2-3 months in hermit mode just in case Major Problem Number One surfaces. As a result, I calculated break-even point and have some bank account “warning alerts ” placed along the way.
4. Find ways to make money - that’s right. There are STILL ways to have an income when you’re funemployed! See these fun little links on my posts (and soon to be advertisements)? Every time you click on one of these, I get what seems like a quarter of a penny. It’s not much, but it adds up. I might have a whole dollar by the end of this. Other ways I can actually make some money include credit card rewards points (go look at Chase Sapphire Preferred), travel writing (about the same rate as the advertisements...), and playing music on the street (for better or worse, probably my best bet).

Major Problem Number Three: Severe Illness

I’m about to get political: Healthcare should absolutely not be tied to employment. I am extremely fortunate to have limited liability; I only pay for myself and am generally healthy. However, even coming from such a low-risk perspective, the US healthcare system is a (sickly) walking oxymoron.

With the Affordable Care Act, many more people are able to qualify for insurance. But, it requires some navigation. You can only enroll during open enrollment, and if you miss that time frame, then you can enroll through Special Enrollment (if you qualify). If you are within 60 days of losing your job, then you are special.

I know what you’re thinking, “go on your parent’s insurance until you’re 26!” Unfortunately, that wasn’t an option for me as the Great White North of Canada covers my dad and my mom is currently on COBRA.

“Oh yeah, just choose COBRA as it’s valid for 18 months,” is now what you’re thinking. Yes, well-versed-in-benefits Reader, but at what cost?!? Did you know that if you wanted to keep your health insurance from your past employer, most companies will mandate that you not only pay for the entire cost of the health care plan but also a 2-5% administration charge? I killed that snake in the grass pretty quickly.

As a result, I navigated to the exchange in order to hunt for the cheapest coverage.

Through a series of phone calls, search results, and faxes (apparently people still use fax machines), I purchased something that looks and smells like insurance. Considering that I’m under 30, I qualified for a specific type of coverage called the Catastrophic Plan. Because it fit the bill—and I loved the seriousness of the name—I signed up.

With my Catastrophic Plan, I am essentially covered through really shitty (read: expensive) situations. I pay everything out of pocket up until $7,125 at which point my insurer takes over and opens their wallet. If I got malaria, for instance, my insurer would pay for the bulk of treatment so that I am not left with Major Problem Number Two...and hopefully not left with malaria.

Major Problem Number Four: Death

This is self-explanatory. I am trying to come back alive.

To do that, common sense will play a big part. I started making a list but I really think it boils down to these two points:

1. Don’t go to sketchy places alone with sketchy people - I’m all about meeting new people and finding new adventures, but you have to be a little warier as a solo wanderer.
2. Don’t be stupid, or act that way - For instance, getting super sloppy drunk in a new place, with no sense of direction, with no friends watching out for you, and with no language skills is a very bad idea. And don’t act like that even if you’re sober.

There you have it. The majority of the planning I have done revolves around avoiding Major Problems 1-4. I still have to book 90% of my hostels and activities, and I don’t want to until I’m on the road. But not having a place to stay and not knowing what to do yet are only minor, and frankly not even problems.