I finally got my first remote job.
Customer support specialist. $42,000/year. Work from anywhere. I was thrilled.
Then I almost got fired in my first 30 days.
I made rookie mistakes that nearly cost me everything. My manager pulled me into a one-on-one after two weeks: "We need to talk about your performance."
I thought remote work would be easier than office work. I was wrong.
Here are the 5 mistakes I made—and exactly what I'd do differently if I could start over.
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Mistake #1: I Didn't Overcommunicate (And My Manager Thought I Wasn't Working)
What I did wrong:
In my office jobs, people could see me working. My boss walked by my desk. Colleagues saw me at my computer.
When I went remote, I kept the same communication style. I'd finish tasks and move on to the next one. I didn't update anyone unless they asked.
After two weeks, my manager said: "I have no idea what you're doing all day. Are you actually working?"
I was working 9 hours a day. But because I wasn't visible, it looked like I was doing nothing.
⚠️ The Remote Reality
In remote work, invisible work = no work. If your manager can't see your progress, they assume you're not making any.
What I'd do differently:
Overcommunicate Everything
Morning check-in (before 9am):
- "Good morning! Today I'm working on: [List 3 tasks]. Will update by EOD."
End-of-day update (before 5pm):
- "Today I completed: [List completed tasks]"
- "Tomorrow I'll focus on: [Next priorities]"
- "Blockers: [Any issues or none]"
Real-time updates (Slack/Teams):
- When you start a task: "Starting on [task name]"
- When you finish: "Completed [task name], moving to [next task]"
- When you're blocked: "Need help with [issue], waiting on [person/info]"
This feels like overkill. It's not. It's the difference between looking lazy and looking productive.
Mistake #2: I Didn't Set Boundaries (And Worked Myself Into Burnout)
What I did wrong:
Remote work = flexible schedule, right? I thought I could work whenever I wanted.
So I did. I worked at 7am. Then 10am. Then 3pm. Then 9pm. I answered Slack messages at midnight because "I was still up anyway."
Within three weeks, I was exhausted. No energy. Resenting the job I'd been so excited about.
My manager noticed: "You're responding to messages at 11pm. That's not sustainable. We need you to set working hours."
The Burnout Timeline
- Week 1: "This is amazing! I can work from my couch!"
- Week 2: "Wait, why am I working 10 hours a day?"
- Week 3: "I never leave my desk. Is this healthy?"
- Week 4: "I hate this. I want to quit."
What I'd do differently:
Set Hard Boundaries from Day 1
Step 1: Define your working hours
- Example: 9am-5pm Monday-Friday (or whatever your company expects)
- Block these hours on your calendar
- Tell your team: "I'm available 9-5 ET, offline outside those hours"
Step 2: Create physical boundaries
- Work from one specific spot (not your bed, not your couch)
- When work hours end, physically leave that spot
- If possible, close the door or turn off your monitor
Step 3: Use status updates
- Slack/Teams status: "🟢 Available (9am-5pm)" during work hours
- After 5pm: "🔴 Offline until tomorrow"
- Don't respond to non-urgent messages after hours
Step 4: Take real breaks
- Lunch break: Leave your desk. Eat somewhere else.
- 15-min break every 2 hours: Walk, stretch, look away from screen
- Don't eat lunch while working (I did this for 2 weeks—terrible idea)
Mistake #3: I Assumed Everyone Understood My Messages (They Didn't)
What I did wrong:
I sent a lot of messages like this:
Me: "Hey, can you send me that file?"
10 minutes later...
Coworker: "Which file?"
Me: "The one from yesterday"
Coworker: "We discussed multiple files yesterday. Which one specifically?"
In person, I could point at my screen or gesture. Over Slack, my vague messages caused constant confusion.
My manager's feedback: "Your communication needs to be clearer. We're wasting time on back-and-forth."
What I'd do differently:
❌ Vague Messages (What I Did)
- "Can you check that?"
- "When is this due?"
- "Did you see my email?"
- "Can we meet?"
- "This isn't working"
✅ Clear Messages (What I Should've Done)
- "Can you review the Q4 Report (Google Doc link) by Friday 5pm?"
- "When is the Johnson project deadline? (Client says they need it by Dec 15)"
- "Did you see my email from today at 10:15am about the budget approval?"
- "Can we meet this week to discuss the marketing plan? I'm free Tue/Wed 2-4pm"
- "The login button on staging.example.com isn't working - getting Error 500 when I click it"
💡 The 5 W's of Remote Communication
Every message should answer:
- What: What specifically are you asking about/referring to?
- Where: Link to doc, file location, website URL
- When: Deadline, time frame, urgency
- Who: Who needs to do this/who's involved?
- Why: Context so they understand importance
Mistake #4: I Didn't Ask Questions (Because I Didn't Want to Look Stupid)
What I did wrong:
I was new. I didn't understand half the company jargon, tools, or processes.
But I didn't want to look incompetent on day 3, so I pretended I understood everything.
"Can you update the CRM with the latest pipeline data from the Q4 deck?"
Me (having no idea what this means): "Sure!"
I spent 2 hours Googling, guessing, and making mistakes. I updated the wrong system. I used the wrong data. My manager had to redo my work.
Her feedback: "Why didn't you ask? It would've taken me 30 seconds to explain."
⚠️ The New Employee Trap
Not asking questions doesn't make you look smart. It makes you look like you're guessing—and wasting everyone's time when you get it wrong.
What I'd do differently:
Ask Questions Like a Pro
Template 1: When you don't understand a task
"Quick clarification on [task name]:
- You mentioned [thing I don't understand]. Can you explain what that means?
- I want to make sure I do this correctly the first time."
Template 2: When you don't know how to use a tool
"This is my first time using [tool name]. Can you point me to:
- Any training docs/videos?
- Or would you have 5 min to show me the basics?"
Template 3: When you're not sure about priorities
"I have 3 tasks today:
- [Task A]
- [Task B]
- [Task C]
Which should I prioritize first?"
When to ask questions:
- ✅ When instructions are unclear
- ✅ When you don't understand company-specific terms
- ✅ When you're not sure about deadlines or priorities
- ✅ When you've tried to figure it out for 15+ minutes and still don't know
When NOT to ask questions:
- ❌ Before checking documentation/wikis/previous messages
- ❌ When the answer is in the original instructions (reread first)
- ❌ Questions you can easily Google in 30 seconds
Mistake #5: I Didn't Track My Work (And Had Nothing to Show at My Review)
What I did wrong:
At the end of my first month, my manager scheduled a check-in: "How do you think your first 30 days went?"
Me: "Uh... good? I've been working hard."
Manager: "Can you tell me specifically what you accomplished?"
I froze. I knew I'd done a lot. But I couldn't remember details. I couldn't name specific wins. I sounded unprepared.
Meanwhile, a coworker who started the same day as me rattled off:
- "Resolved 47 customer tickets with 98% satisfaction"
- "Created 3 help docs that reduced repeat questions by 30%"
- "Joined 12 customer calls and got 5-star feedback on all of them"
Guess who looked more impressive?
What I'd do differently:
Track Your Wins Daily
Create a "Wins Doc" (Google Doc or Notion)
Format:
Week of Dec 2-6, 2025
- ✅ Resolved 12 customer support tickets (avg response time: 2 hours)
- ✅ Completed onboarding training (100% quiz score)
- ✅ Created template for common customer question (saved team 1 hour/day)
- ✅ Joined 3 team meetings, contributed ideas for Q1 planning
- ✅ Fixed bug in customer portal (reported by 5 customers)
Update this doc every Friday
Spend 10 minutes listing what you accomplished that week.
Why this matters:
- ✅ You have proof of your work for performance reviews
- ✅ You can quickly answer "What did you do this week?" in 1-on-1s
- ✅ You can see your own progress (motivating when you feel stuck)
- ✅ You have examples for your resume/LinkedIn when you job search later
What Happened After I Fixed These Mistakes?
I went from "on thin ice" to "employee of the quarter" in 90 days.
Here's what changed:
- Overcommunication: My manager knew exactly what I was doing. No more "Are you working?" questions.
- Boundaries: I stopped working evenings. Felt less burned out. Actually enjoyed my job again.
- Clear communication: Fewer back-and-forth messages. Teammates said I was "easy to work with."
- Asking questions: I learned faster. Made fewer mistakes. Looked competent instead of clueless.
- Tracking wins: At my 90-day review, I had a list of 47 specific accomplishments. Got praised for "exceeding expectations."
Remote work isn't harder than office work. It's just different.
The skills that make you successful in an office (being visible, asking questions in person, casual desk chats) don't translate directly to remote work.
You have to learn new skills. And the faster you learn them, the faster you'll succeed.
Your Action Plan: Start Your Remote Job Right
Before Your First Day
- ✅ Set up dedicated workspace (not your bed)
- ✅ Test your internet, camera, microphone
- ✅ Download our First Week Checklist
- ✅ Prepare questions to ask on day 1
Week 1: Establish Good Habits
- ✅ Send morning check-ins + EOD updates daily
- ✅ Set Slack/Teams status to show availability
- ✅ Ask clarifying questions immediately (don't guess)
- ✅ Create your "Wins Doc" and log first week accomplishments
- ✅ Set working hours and stick to them
Week 2-4: Build Trust
- ✅ Overcommunicate progress on every project
- ✅ Use the 5 W's for every message (what, where, when, who, why)
- ✅ Update your Wins Doc weekly
- ✅ Schedule 1-on-1 with manager to ask for feedback
- ✅ Join team meetings with camera on and contribute ideas
Month 2+: Level Up
- ✅ Take on small projects to show initiative
- ✅ Document processes to help future new hires
- ✅ Build relationships with teammates (virtual coffee chats)
- ✅ Prepare for 90-day review with your Wins Doc
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