73 Days of Email Writing Disasters: My Boss Was Speechless

I once replied-all to 200 people with "sounds good babe" meant for my partner. That wasn't even my worst email disaster.

My actual worst: sending a client a proposal with my internal notes still visible. The notes said "Quote them $5K but we'd do it for $3K if pushed." They pushed. Hard.

For 73 days, I documented every email mistake I made or witnessed. I collected disasters from colleagues, friends, and the depths of Reddit. Then I reverse-engineered what went wrong and built a system to prevent each type of failure.

Here's everything I learned about email that nobody teaches you.

The "Send" Button Is Your Enemy

Most email disasters happen in the two seconds between clicking send and realizing your mistake.

I now use a 60-second delay rule. Both Gmail and Outlook let you set an "undo send" window. I maxed mine out and use every second. During that minute, I ask three questions:

1. Would I be comfortable if this was forwarded to anyone?
2. Is there anything that could be misread?
3. Did I actually attach the attachment?

That third one catches me at least twice a week.

The Tone Problem Nobody Talks About

Written words carry no tone. Your reader supplies it based on their mood, their relationship with you, and what they expect from you.

"Please advise" reads as neutral to the writer. To some readers, it's passive-aggressive. To others, it's formal. To a few, it's lazy.

I started rewriting my most common phrases:

Instead of: "Please advise" I write: "What do you think?" or "I'd love your input on this"

Instead of: "As per my last email" I write: "Building on what I mentioned before..." or just re-state the point

Instead of: "Going forward" I write: "For the next project..." or "Starting Monday..."

The goal isn't to be casual. It's to be impossible to misread.

The Subject Line Framework

Bad subject lines guarantee your email gets lost or ignored. Here's what consistently works:

For requests: [Action needed] + specific topic + timeline Example: "Quick review needed: Q3 budget draft by Thursday"

For updates: [FYI] or [Update] + what changed Example: "Update: Client meeting moved to 2pm"

For questions: Specific question as subject Example: "Should we include case studies in the proposal?"

Never use one-word subjects. "Meeting" tells nobody anything. "Tuesday's client meeting agenda" does.

The One-Screen Rule

If your email requires scrolling on a phone, it's too long. People skim emails. They don't read them.

My format for any email over three sentences:

Opening line: Why I'm writing (one sentence)

The ask or update: What I need or what happened (bold the key action)

Context: Background only if necessary (bullet points)

Next step: What happens now and when

Nobody has ever complained that my emails were too short.

CC vs BCC: A Survival Guide

Improper CC use has destroyed more workplace relationships than actual disagreements.

CC someone when:

• They need to be aware but don't need to respond
• You're creating a paper trail they should see
• Their boss asked to be kept in the loop

Don't CC when:

• You're trying to pressure someone by involving their manager
• You want to show off that you did something
• You're covering yourself preemptively

BCC is for:

• Large distribution lists where replies would spam everyone
• Introducing someone who's dropping off the thread
• Protecting email addresses from external contacts

Never BCC to secretly include someone. It always backfires when they accidentally reply-all.

The Reply Timeline

I experimented with response times for three months:

Immediate replies (under 5 minutes) set a bad precedent. People expect you to always be available.

Same-day replies for anything urgent or external. Clients shouldn't wait overnight.

24-48 hours for internal non-urgent emails. This is completely acceptable.

Never: Reply when emotional. I draft, close the email, and come back later.

My Pre-Send Checklist

Before every important email:

• Is the recipient correct? (Check twice for similar names)
• Is the subject line specific?
• Did I attach the attachment?
• Is my ask clear and bolded?
• Can this be read in under 30 seconds?
• Would I be okay if this was forwarded?
• Is my tone impossible to misread?

For high-stakes emails, I read it out loud. Awkward phrasing becomes obvious when spoken.

The Real Shift

The biggest change wasn't a technique. It was realizing that every email shapes how people see me professionally.

When I started treating emails as real writing—with drafts, revision, and intentional choices—my relationships improved. People respond faster. Miscommunications dropped.

Start with one change: the 60-second delay. You'll catch more disasters than you expect.

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