(A Very Niche) Problem

 An Ennie award winning blogger issued an impromptu, Cleric themed blog bandwagon, due to an avid Undertale fanboy passing away. 

Allegedly, the author is a (P)OSR blogger who adores dabbling in lighthearted heresy (see above). However, said author also bounces off most medieval fantasy settings; i.e. the stereotypical setting for Clerics.

(An Even More Niche) Solution

Coincidentally, the author accidentally catfished said Ennie award winning blogger with the promises of a Dicepool Based, Mark of the Odd Heartbreaker. While that project is at best trapped in developer purgatory, one of the concept backgrounds was the "HR Vicar."

If only there was some well known, Sci-Fi-esque Mark of the Odd system with bespoke backgrounds the author could adapt this idea to... I think you can see where this is going:

 Justifying Failed Careers in Electric Bastionland

 Roughly 2/3rds of Electric Bastionland is FILLED with potential starting backgrounds; over 100 "Failed Careers." However, the book itself offers little guidance in homebrewing your own Failed Careers.

In fact, the only (convenient) resource on writing Failed Careers focuses on fleshing out existing ideas. It isn't specified how to fit said Career within the implied setting of Bastionland.

 Of course, Electric Bastionland's setting is a type of "Vibes-based Cannon," uniquely molded to each table. However, unguided creativity can be its own type of hell.

Thus, the author posits 2 questions that may help when sculpting a new Failed Career:

• Does this "Career" fit Bastionland's general setting?
• Why did this "Career" fail?
  

Lets use this custom made Failed Career, for example:

Why yes, this terrible drawing is the reason the blog missed the original deadline. Also forgive the author for bastardizing Alec Sorensen's work.

Does it Fit the Setting?

Unfortunately, this is still up to individual taste. However, designing towards a "20-Century Oddball Urban Fantasy" setting should act as a "solid" baseline. 

When in doubt, envision Brazil, anything by Franz Kafka, and a Muppet's Christmas Carol

For our example Career, a company Cleric preaching the Holy doctrines of the business is a dystopian concept that can gel with the legalese spaghetti code of Bastionland's bureaucratic hellscape.

Why is it a Failed Career? 

In Electric Bastionland, you can infer several reasons why a character has a Failed Career:

• It's not actually a Career, but an Origin/Event. (Dead-Shoresman, Mockery, Failed Citizen)
• It's outdated by Bastionland's standards. (Expelled Lamplighter, Apprentice Sweep)
• It was horrible enough to take the risk. (Contract Castaway, Paid Fighter, Animal Vassal)
• It was too niche to be stable (Sky Trooper, Cryptohistorian, Avant Guardsman)
• The Character was just unlucky.
  

 From our example Career, we can immediately rule out the first 2 reasons. Both the HR & Clergy part of the HR Clergyman implies this as a recent type of work one isn't born into.

The next 2 reasons, however, require further examination. Consider Maslow's Hierarchy of Needs:

By Hamish.croker - Own work, CC BY-SA 4.0, https://commons.wikimedia.org/w/index.php?curid=164544166

 Maslow's Hierarchy of Needs vs Character Motivation

Anyone already familiar with this pyramid knows that all needs on a given tier only matter if all needs in the tiers below are satisfied. Since adventuring is an inherently volatile trade, the safety needs will never be fully met.

Thus, any Career that fulfills both the bottom 2 needs of the pyramid is logically a "better choice" for the well adjusted character then risking your life adventuring. Additionally this covers the obvious case of "the Job's pay was too pitiful for any hope of paying off the dept."

For the HR Clergyman, the Career presumably pays well enough to fulfill the bottom two needs; at best, it could fulfill the next 2 needs on the pyramid too if the character was a sociopath. Thus, it wouldn't make sense for the Character to willingly leave their job to pay off the dept.

Maslow's Hierarchy of Needs vs Societal Motivation

Thinking abstractly, we can apply Maslow's Pyramid to a society's own needs. I.e. a Career can be thought of as fulfilling some need within Bastion or a settlement in Deep Country.

 Then, if a Career satisfies a lower tier need on the pyramid, it is critical for a society's well being. Consequently, the inverse implies a Career operating on a higher tier isn't "essential" and thus a more volatile industry.

Of course, this line of thinking is very Corpo/Productivity Centric; perfect for a game about a modernizing society. If you have any more doubts, please ask an artist and a plumber how comfortable they feel about their job security.

Applied to our HR Clergyman, we can argue the Career operates on the middle tier of the pyramid. Thus, this Career occupies a sort of middle ground between too niche and secure.

The "Boring" Reason

By process of elimination, the HR Clergyman is a Failed Career due to bad luck/other external factors. There's nothing actually wrong with this, several of Electric Bastionland's Failed Careers imply this.

 All this means, is that HR Clergyman needs justify 6 interesting situations for such bad luck, while still adding appropriate flavor to the class. 

Mix and Match

Of course, there's nothing actually stopping you from mixing and matching all the given reasons. In fact, it'd be very Bastion-esque if there was a clown car of almost paradoxical justifications for a Failed Career.

Damn it, the answer was vibes based worldbuilding all along.