🔐January-proof your income

🔐 December is winding down. Your inbox is still pretending nothing is coming. January, however, is already warming up its opinions.

This week’s focus: January-proof your income before the scramble starts. We’ve handpicked a few low-drama ways to lock scope, line up work, and turn “let’s talk in January” into actual plans—using tools you already have. (3-minute read)

🔦 Week’s highlights:

• Tool Spotlight: ChatGPT simplifies January follow-ups; Boomerang makes “let’s talk in January” stop ghosting you.

• Sherpa’s Shortcuts: One runway doc. One scope mirror. Fewer January surprises, zero unpaid “extras.”

• Sherpa’s Pack: Ditch “quick calls” with an async update template clients actually read.

• The Ridgeline news: ChatGPT chills out and AI glasses tease hands-free workdays.

• 😝 Tools Gone Wild: Meetings are vanishing at some key companies in favor of async tools.

AI tool spotlight:

Tool Sherpa explores the flood of new AI apps and carefully selects only proven tools.

🔍 ChatGPT: Close the loop without the spiral

Why it matters:
January income doesn’t usually fall apart from a lack of work. It slips because follow-ups stall. Writing “just checking in” feels awkward, emotional, or easy to postpone. Your favorite AI chatbot (ChatGPT, Gemini, Claude, etc.) removes that friction, turning messy notes into short, neutral check-ins that confirm scope and timing, without sounding salesy or stiff. You stop overthinking, send the message, and move on.

Best use case:
Paste your rough notes or half-drafted email and ask for a calm, professional check-in that confirms January scope or next steps. Send it. Loop closed.

Who it’s for:
• Freelancers who overthink follow-ups
• Writers tired of rewriting “just checking in” emails
• Anyone seeking clarity minus emotional labor

Pros:
Fast clarity with a neutral tone. A few well-phrased sentences can prevent January surprises and save mental drag.

Cons:
It won’t press send for you. You still have to be mildly brave.

Pricing:
Free tier available.

👉 Visit ChatGPT here 

🔍 Boomerang for Gmail: Make follow-ups unavoidable (politely)

Why it matters:
Writers don’t lose January income because clients say no. They lose it because emails drift. An editor says “let’s circle back,” a client replies “sounds good,” and the holidays swallow the thread. Boomerang for Gmail makes follow-ups automatic, so momentum doesn’t depend on memory, guilt, or perfect timing.

Best use case:
Send your normal email. If no reply comes back, Boomerang resurfaces it in your inbox on a date you choose, so nothing quietly dies over the holidays.

Who it’s for:
• Writers waiting on editor or client confirmation
• Freelancers juggling multiple open threads
• Anyone tired of manually remembering who to nudge

Pros:
Invisible pressure. Calm follow-ups. No “just checking in” spiral. Threads resurface exactly when you need them.

Cons:
Only works inside Gmail. And it won’t write the email—that’s what ChatGPT is for.

Pricing:
Free tier available. Paid starts at about $5/month, annually.

👉 Learn more about Boomerang

_{Disclaimer: Some links may earn us a small commission, at no additional cost to you.}

Sherpa’s shortcuts 🪓

Sherpa-approved hacks to streamline your workflow in today’s most popular AI apps.
 

⚡ Hack #1: January income runway (one doc)

Problem:
January feels fuzzy. Clients say “let’s talk in January.” You mentally count the money anyway. Anxiety ensues.

Solution:
Create one simple “runway” doc that shows what’s real, and forces clarity before the scramble.

Open one doc:
• Notion or Google Docs

Create three sections:
• Active
• Paused
• Likely January

For each client, add:
• Next paid milestone (renewal, phase, start date)
• One line of scope reality (“Includes X. Not Y.”)

Close the loop:
Send one calm follow-up to anyone in Likely January:
“Quick January check-in, are we continuing with [X] as planned, or has anything shifted?”

Review once a week. Then stop.

💡 Sherpa Tip:
If it’s not written down and confirmed, don’t count the money. Relief is a revenue strategy.

Helpful links:
• Open Notion
• Open Google Docs

⚡ Hack #2: The January scope mirror (for ongoing work)

Problem:
January work resumes, but scope lives in everyone’s head. You assume one thing. Your client assumes another.

Solution:
For ongoing or restarting work, mirror scope back before January begins, so assumptions don’t turn into unpaid extras later.

Pick one ongoing or likely-January client.
Skip completed one-offs. This is for work that continues or restarts.

Write a three-line scope mirror:
• What I’ll deliver in January
• What’s not included
• When we’ll revisit scope if needed

Share it simply:
“Before we roll into January, here’s how I’m thinking about scope so we’re aligned.”

Pause. Let them react.
Silence = agreement. Edits = clarity. Both save you time.

💡 Sherpa Tip:
Unspoken scope is where margins quietly disappear. Name it early and January stays boring, in the best way.

🏔 Sherpa’s Pack

Free stuff to help freelancers get an edge.

Replace “quick calls” with a written update clients can actually follow. Grab Smartsheet’s free weekly employee status report template in a Google Docs format you can hand to clients for async updates: wins, next steps, and anything stuck, without a meeting.

👉 Grab the free async update template

The Ridgeline news🏔️

The latest on how AI is rewriting the rules for solopreneurs and small teams.

Let’s trek:

🤖 ChatGPT got nicer: OpenAI quietly dialed up ChatGPT’s warmth. Fewer robotic replies, more human tone—without drifting into pep-talk territory. 🔗 👉 See what changed

 📉 LinkedIn’s algo backlash: Spam cleanup blamed for new post rankings, while women claimed pro-male bias.
 🔗 👉 Decode the algorithm 

🧪 OpenAI hinted ahead: Prepare for faster image creation, smarter reasoning, fewer hallucinations, and calmer responses. 🔗 👉 Read the signal

🕶️ AI glasses, freelancer edition:* Google’s AI glasses are targeting 2026 with voice. Think hands-free prompts, quick answers mid-task. 🔗 👉 Preview the future

🧠 A quiet freelance drag: Smart people often slow their income by overthinking, perfecting endlessly, and waiting to move. 🔗 👉 Check the list

Final sip:
☕ AI’s calmer, platforms punish fluff, and brains still aren’t the bottleneck. Quiet progress beats loud hacks every time.

###

Tools gone wild! 😜

Let’s end with a laugh — when AI tools take a detour off the happy path.

When meetings finally went extinct

Turns out the boldest productivity move wasn’t another meeting—it was not having one. Shopify went async-first, swapping standing in-person meetings for written updates and decision docs. Fewer interruptions. Faster calls. Way less calendar cosplay. When no one’s waiting for a time slot, work mysteriously…gets done.
Read Shopify’s take on async work

📌 Lesson learned:
Urgency is optional. Clarity isn’t. If a company that big can stop reacting in real time, so can freelancers.

🧭 What’s Next?

We’ll be back next week with more low-drama ways to protect your time—and your income, as 2026 rolls in. Until then, dig into past editions packed with proven tools and calm workflows that set you up early, not frantically.
👉 Explore the Tool Sherpa AI back issues

—Your Sherpa team 🏔️