Raise your rates, lose the drama

✉️ You carried clients through summer; your rates stayed in spring. Now it’s time to raise them, without raising anyone’s blood pressure (yours included).

Welcome to Tool Sherpa AI, the best community for small teams and solopreneurs navigating the avalanche of new AI tools, tips and strategies. This week’s focus: raise your fees without drama. Use real numbers, friendly scripts, and invoicing that sticks. (3-minute read).

🔦 Week’s highlights

• Tool Spotlight: Tap Toggl Track to help justify a rate increase; FreshBooks to lock new rates and ease faster payments.

• Sherpa’s Shortcuts: Humanize your rate bump with a 45-second Tella video; shut down scope creep with TextExpander.

• The Ridgeline news: Free Perplexity AI !, and Claude forgets unless you pay.

• 😝 Tools Gone Wild: Canva triples team pricing, then scrambles back down the mountain.

AI tool spotlight:

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

🔍 Toggl Track: show proof for a painless raise

Why it matters: Freelancers don’t get raises by saying “I feel busier.” Clients don’t care how you feel. Toggl Track is a simple timer: hit start when you’re writing, editing, or stuck on Zoom. Hit stop when you’re done. A few months later, it delivers a chart showing your billable hours—and how much was free labor. Drop that chart in your “new rates” email and suddenly your rate bump looks like math, not whining.

Who is it for:

• Writers juggling multiple clients and sneaky “quick edits”

• Freelancers who forget half their time is unpaid

• People who prefer invoicing to wrestling with spreadsheets

Best use case: Run a 90-day report before you raise rates to reveal exactly how much time went to actual deliverables versus calls, emails, and revision purgatory. Paste into your note. Clients see the gap. You see the raise.

Pros: Toggl makes invisible work impossible to ignore. It tallies every draft, quick call, and edit. The resulting chart then whispers: “You’re undercharging, and here’s proof.” 

Cons: Forget to press start, and it’s as if the day never happened. Free plan works fine, but juicier client-by-client breakdowns live on paid tiers.

Pricing: Free for solos. Paid starts at $9/month.

👉 Try Toggl Track free

🔍 FreshBooks: raise without chasing checks

Why it matters: Raising rates is half the battle. The other half? Actually getting paid. FreshBooks makes it painless with polished invoices, pay-now links, and automatic nudges that handle the awkward stuff for you.

Who is it for:

• Freelancers who hate chasing money

• Writers moving clients from hourly work to neat retainers

• Anyone who wants rate changes to look official, not awkward

Best use case: The week before your rate kicks in, update recurring invoices in FreshBooks. Clients get the new number, the same polished format, and a big green “Pay Now” button. That single click says you’re serious, without a single “per my last email.”

Pros: Recurring billing locks in new rates. Late fees send reminders so you don’t have to.

Cons: After the trial, you’ll pay to keep the automation. For fancy accounting reports you may still need your spreadsheet (or an accountant).

Pricing: Free trial. Paid starts at around $17/month.

👉 Try FreshBooks free

_{Disclaimer: Some links may earn us a small commission, but they never affect what we recommend.}

Sherpa’s shortcuts 🪓

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

🪓 Sherpa’s shortcuts

Hack #1: the 45-second raise video

Problem: “Hi, my rate’s going up” reads like a ransom note.

Solution: Record a Loom or Tella so it feels human and a bit harder to argue with. Keep it under 45 seconds.

Three bullets: One win you delivered (“24 posts, zero missed deadlines”) • One thing that isn’t changing (quality, turnaround, your sanity) • One Toggl Track chart showing unpaid hours → followed by the new rate (+15%, starting Oct 15)

Steps:

1. Screenshot a Toggl summary (billable vs. freebie hours).

2. Hit record. Smile once. No TED Talk, just bullets.

3. Auto-caption it so nobody pretends they “couldn’t hear.”

4. Paste the link at top of your rate-change email.

Camera-shy option: Skip the face. Record the Toggl chart + slides with a voiceover. Same effect, fewer bad-hair worries.

Result: Clients get proof, continuity, and a confident raise in under a minute. You look like a pro, not a hostage negotiator.

👉 Try Toggl Track free

Hack #2: the scope-creep smackdown

Problem: Clients love sneaking in “just one more thing.” That “thing” usually eats your weekend.

Solution: Set up a canned reply using TextExpander or your OS text replacement to drop a polite but firm request: pay more or wait longer.

Steps:

1. Create a new snippet in TextExpander (or Mac/PC text replace).

2. Paste this macro:

“Great idea! That’s outside our current scope. Two options:

1. Add-on: I’ll include it this cycle for $___ (+2 days).

2. Next round: I’ll slot it first next month at the regular rate. Reply ADD-ON or NEXT and I’ll confirm the timeline.”

3. Save it, test it, then use it when scope creeps.

Result: Arguing over scope stops. The macro does the dirty work. Clients pick a path, you get paid, and your weekend stays yours.

👉 Try TextExpander for free

The Ridgeline news🏔️

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

Let’s trek:

🪙 Freelancers, meet free Perplexity: We said it last week, saying it again — it’s that good. Your PayPal or Venmo account = one free year of Perplexity Pro. 🔗 Grab the freebie

🤖 ChatGPT-5 sweats the small stuff: Writers test it on essays, emails, and stories. Verdict: nails tone, flubs facts, still needs a human chaperone. 🔗 See the verdict

📒 Prompts that protect your work: Five sly ChatGPT prompts that crank out content clients can’t swipe or recycle. 🔗 Try the prompts

🐟 Claude’s pricey memory: Anthropic will remember your chats, if you pay. Otherwise, your AI sidekick forgets faster than a goldfish. 🔗 Read the fine print

📈 AI grows your solo biz: A solopreneur’s playbook for stacking new clients with AI without selling your soul (or Sundays). 🔗 Get the playbook

☕ Final sip: AI’s trying so hard to “be human,” it’s basically doing open mic night, while you cash the tips.

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Tools gone wild! 😜

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

Triple trouble pricing

Canva tried the old “because AI” move: “Teams” pricing for the popular graphics app jumped from ~$120 → $500/year (with a oh-so-generous 40% coupon). Users howled, forcing Canva to hustle back to legacy pricing for loyal accounts.

📌 Lesson learned: Don’t drop a 3x hike overnight and expect applause. Phase in new rates, grandfather loyal clients for a time, and explain the added value. Blaming AI? Leave that at base camp.

🧭 What’s Next?

Next week we’ll tackle new hacks for client communication. Until then, a shout-out to our sponsor Every.io — helping freelancers and solopreneurs incorporate fast, stay compliant, and protect their business without the paperwork headache (+ with cashback!)

👉 Check out Every.io below

—Your Sherpa team 🏔️