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Cocky Boss Cuts Out The Middleman, Then Begs For Help When His Container Gets Stuck At Customs

by Annie Nguyen
February 9, 2026
in Social Issues

There is a certain kind of workplace clash that many professionals recognize instantly. The seasoned employee who understands the risks meets the confident newcomer who believes those risks are exaggerated. When business decisions hang in the balance, that dynamic can become especially tense.

In this case, a purchasing manager found himself caught between doing his job and letting his boss learn the hard way. What began as a simple discussion about saving money quickly evolved into a real-world experiment in international shipping. The outcome was far from what anyone had predicted. Keep reading to see how this corporate gamble unfolded.

A purchasing manager watches her overconfident boss insist on handling a 40-foot import

Cocky Boss Cuts Out The Middleman, Then Begs For Help When His Container Gets Stuck At Customs
not the actual photo

My boss insisted we cut out the middleman to save 15%, so I let him handle the logistics of a 40-foot container.

I work as a purchasing manager for a mid-sized home goods retailer.

We have used the same domestic importer for our seasonal decor for five years.

They charge a markup, but they handle the customs, the quality checks, and the shipping. It is hassle-free.

My new Director of Operations is convinced that he is a business genius. He called a meeting last month

and lectured me about how we are hemorrhaging money by using a local distributor.

He told me to cancel our contract for the holiday shipment and go directly to the source.

I warned him. I told him that dealing with freight forwarders, tariffs, and port delays is a full-time job.

He told me I was just being lazy. He actually said, “Just get me the contacts, I'll close the deal myself.”

So I did. I spent a few days on Alibaba compiling a list of legitimate Chinese manufacturing companies

that produce glass ornaments. I handed him a spreadsheet with twenty factory contacts,

their MOQ (Minimum Order Quantity) requirements, and the time zone differences.

I sat back and watched the show. He realized that the FOB Price does not include shipping to our warehouse.

He wired money to a supplier but forgot to hire a customs broker, so the shipment got flagged by CBP.

The container sat at the port for ten days because he didn't understand what an ISF filing was.

The demurrage fees (fines for not moving the container) alone cost more than the 15% he was trying to save.

He came to my desk yesterday, looking incredibly humbled, and asked if I still had the phone number for our old importer.

TL;DR: Boss thought international trade was easy; I let him manage a direct import order

and he ended up paying double in fines and fees.

Being labeled “lazy” after offering hard-earned expertise can leave a lasting emotional sting.

In the Reddit story, a purchasing manager’s careful warnings were brushed aside by a new Director of Operations, who was convinced he could save 15% by bypassing their trusted importer. The result was a logistical disaster that ultimately cost far more than anyone anticipated.

At the heart of this narrative lies a classic case of overconfidence bias. The Director’s belief in his superior business acumen led him to underestimate the complexities of international trade, customs, tariffs, shipping logistics and overestimate his ability to manage them without prior experience.

This cognitive bias often results in individuals taking on more risk than warranted, ignoring potential pitfalls, and making poor decisions.

Interestingly, overconfidence isn’t exclusive to novices; even seasoned professionals can fall prey to it.

A study published in Research in Organizational Behavior highlights that experts, regardless of their field, can exhibit overconfidence, leading to misjudgments. This underscores the importance of humility and continuous learning, regardless of one’s position or experience.

In this scenario, the Director’s failure to heed the purchasing manager’s warnings led to tangible consequences: delayed shipments, customs issues, and financial losses. It’s a stark reminder that confidence should be balanced with caution, especially when venturing into unfamiliar territories.

For organizations, this tale serves as a lesson in valuing and leveraging internal expertise. Encouraging open dialogue, fostering a culture where concerns can be voiced without fear, and recognizing the limits of one’s knowledge can prevent costly mistakes. After all, acknowledging what we don’t know is as crucial as applying what we do.

In conclusion, while ambition and initiative are commendable, they must be tempered with humility and respect for established expertise. Organizations thrive when they balance innovation with informed decision-making, ensuring that confidence doesn’t overshadow competence.

Here’s how people reacted to the post:

These commenters agreed that logistics is a full-time industry and the boss learned hard

humanleon − I mean - fair play to him for recognising his mistake and coming back to you.

We learn the most expensive lessons the best.

an_asimovian − My entire job is being that middleman, except for frozen foodstuffs,

that demurrage or any regulatory errors will absolutely k__l you,

its a whole different ball game compared to domestic logistics, definitely something where you want someone

who does it as their job running the show vs trying to figure it out as you go.

Plenty-Aside8676 − Anyone who has spent time managing purchasing and international logistics knows that

this arrangement works well for a reason. It is not only a full-time position it is an entire industry.

Perhaps going forward he will appreciate you more.

Kip336 − As a freight forwarder, I laughed. So many times do I get asked why people pay me to do my job,

what good am I for society etc. It only ever takes one shipment before they call me back.

Sakawatchi − As a freight forwarder who have worked both export to the US and import in the US

I can vividly imagine the entirety of this shipshow. And the fines.

And the possible HOURS spent by the freight forwarder and customs broker on the import side trying to save it.

DW171 − A good customs and shipping broker is worth their weight in "pier passes". lol

Even in good times logistics is a huge pain in the ass.

Right now with all the tariffs and illogical holds on shipments, it's a nightmare. Perfect training grounds for a rookie. lol

LuckyMyLunacy − As a freight forwarder, this made me cackle.

Have had a few customers try this themselves over the years only to come crawling back.

If managing international shipments was easy, nobody would be paying me a salary to do it for other people;

my job would simply not exist.

therandomuser84 − I work in logistics, specifically air and ocean shipments.

Every single shipment has 3-5 people doing more than an hour's work on it to get it from China to the US or vice versa.

Some shipments take upwards of 40 man-hours to get done.

Your boss is incredibly stupid for thinking he can do it all himself on top of whatever else he has to do as well.

These commenters were amused, approving, and fascinated by the chaos of shipping

Pyehole − I'm sure r/supplychain would find this amusing.

PomeloPepper − A few months ago I sat through a seminar on how import/export has changed under the new rules.

Just listening to the import experts, freight brokers, etc.

Talking about routing and tariffs and cost changes along the way wore me out!

These commenters focused on repairing relations with the previous importer

bevelled_margin − Did he apologise to, and make reparations to, your previous importer

who lost out on this important pre-Christmas business? Would they even take you back as a customer?

AMonkeyAndALavaLamp − Since you were the one who actually cancelled the contract with the importer,

I'm glad your boss didn't make you go back to them, asking for help.

These commenters vented about freight drivers ignoring access rules and paperwork

UsernameHasBeenLost − I'm a project manager for an automation integrator,

and I f__king hate dealing with freight companies, especially for federal projects.

No matter how clearly I spell out base access requirements,

no matter how many times I reiterate that there is ONE gate that the trucks can go to,

and it is NOT the delivery address, and no matter how many times I give them my site lead's number,

I still have drivers calling me or getting turned away at the gate for stupid s__t that I told them about repeatedly.

No, I can't convince the US government to accept your jankass BOL that lists a random address not even on base

that I have no idea where you got because it doesn't match anything I sent you,

and no I can't waive the "no felonies" requirement.

The Director’s experience serves as a reminder that cutting corners in complex processes like international shipping can lead to greater expenses and operational disruptions. Engaging professionals who understand the intricacies of logistics is not just beneficial; it’s essential.

Have you encountered similar challenges in your industry? Share your experiences and insights in the comments below!

Annie Nguyen

Annie Nguyen

Hi, I'm Annie Nguyen. I'm a freelance writer and editor for Daily Highlight with experience across lifestyle, wellness, and personal growth publications. Living in San Francisco gives me endless inspiration, from cozy coffee shop corners to weekend hikes along the coast. Thanks for reading!

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