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The Red Thread This Week:
"If a man knows not to which port he sails, no wind is favorable." — Seneca
June’s in the books and it’s officially July.
The natural midpoint of the year on the calendar.
If you're reading this, I hope you used the first half to start something. A project, a business, a body of work, an idea you'd been circling for a while.
I also hope you've stopped at least once to ask whether it's still pointed where you meant it to be.
That's the whole reason this newsletter exists. To help you see across your own work, catch the patterns, and turn what you notice into better decisions.
Back in December, I shared the exact framework my team uses to build our annual plan, plus a prompt library to help you build yours. If you did that work, consider this issue the other half of it.
A plan you set at the start of the year was built with the information you had at that moment. You've learned a lot since then.
Before sailors had GPS, they used something called dead reckoning. You take your last known position, your speed, your heading, and the time that's passed, and you estimate where you actually are. Not where you hoped you'd be. Where you are.
Then you correct.
Being off course was never considered a failure. It was a normal (and VERY common) condition of the trip.
The real skill was checking often enough to fix it before it got away from you.
So this Red Thread this week is a mid-year check. I've been running it on my own work this month, and I want to hand you the version I use.
~ Jaime
🔑 The Unlock
The Midpoint Is a Position Check, Not a Report Card
Most of us hit the midpoint and instinctively grade ourselves. Did I hit the number? Am I ahead or behind?
That's a report card. Report cards measure the past.
A position check asks something more useful:
“Given everything I know now, is my direction still right?”
Here are 3 moves that turn a vague "how's it going" into a real mid-year check.
1. Check your position, (not your progress.)
Progress measures you against the goal you set in January.
Position measures whether January's goal still deserves your back half of the year.
Those are different questions, and the second one matters big time because direction over speed was the whole idea back in December. At the midpoint, you honor it by checking your position, not just how fast you're moving or how much ground you’ve covered.
The version of you who set those goals was making bets with the information you had at the time.
You now have 6 months of new data. Real customers/audience/team members instead of imagined ones. Real feedback instead of assumptions.
Don't use the midpoint to defend the old plan. Use it to ask whether that plan's assumptions are still standing.
Sometimes they are, and you sail on with confidence.
Sometimes they expired back in April, (maybe without you even noticing,) and you've been navigating by a star that’s actually gone dark.
Either way, you can't correct a heading you never check.
2. Go back to the core questions underneath everything.
When I start any piece of work, 2 questions come before all the others.
Who is this for?
What is this for?
In December I called this frame clarifying the customer reality. The midpoint is when you find out if the frame moved.
In January, those answers may have felt settled. By June, you've actually met the people and shipped the work. And often the reality for your customers (their goals, needs, desires, pains, hopes, etc.) has moved.
The "who" has narrowed. The audience you imagined may have turned out to be a sharper, smaller, more specific group than you guessed.
The "what" has likely also clarified. The job the work is really doing isn't quite the job you wrote down at the top of the year. That’s OK!
This matters because every other decision you’ll make this year going forward, sits downstream from the answers to those 2 questions. Your products, your formats, your channels, your offers, your content calendar, etc.
If the foundation shifted and you didn't update it, you're optimizing a plan built for someone who might not be your real audience or customer anymore.
Re-answer both, out loud, as they're true today. Not as they were true 6 months ago.
3. Decide what to STOP.
A mid-year review will try really hard to generate a longer list. New ideas. New channels. New bets for the back half.
But the year has a fixed amount of room in it. Adding without subtracting is how a good plan becomes an impossible one.
In December I called elegant strategy "subtraction, not addition." The midpoint is where you actually subtract.
The harder and more strategic move is to name what you'll stop.
The project or repetitive task that's become a tax.
The format that made sense in January and doesn't now.
The bet that hasn't paid and won't.
A gardener doesn't grow a healthier plant by adding. Mid-season, they prune, so the plant sends its energy where it counts.
You have that same opportunity right now, with better information than you'll have at any other point in the year.
Use it to cut, not just to add.
💡 Mindset Shift
Before you grade the first-half, look hard at the scoreboard you're tracking.
We’ve inherited a very narrow definition of success from a hundred years of industrial age thinking — “More.”
More revenue, more reach, more followers; everything bigger than last quarter.
So when we run a midpoint check, we hold the work up against "more" by reflex. And if the number we’re tracking didn't climb up and to the right, we feel behind.
So, here are a few questions worth considering:
What number are you truly measuring?
Is it a number you picked, or did someone else?
Does that number dictate how you feel about your work?
I have this conversation with musicians all the time, and music is an easy example: imagine you’re a jazz musician, opening your Spotify dashboard, and being smacked with pain and frustration at your monthly listener count, or streams, or followers because they’re “small.”
There's an easy fix for making those numbers bigger. Stop making jazz and start making pop music. Pop is, by definition, more popular. That's the whole purpose of the genre.
Except…that was likely never the work you set out to make. And Jazz, measured against the scoreboard of Pop music, will always read like a shortfall.
But, if your jazz music is measured by what it's actually for — its ability to matter to someone else, and your ability to keep doing it in a sustainable way — it might actually be considered a wild success.
This is how a lot of good work gets abandoned at the midpoint. The work was still doing its job. It was just being measured on the wrong scoreboard.
Renowned jazz pianist Patricia Barber has played a Monday night residency at the Green Mill in Chicago for more than 2 decades. The room holds about 100 people. It consistently sells out.
That's what success can look like. What enough can look like. A full room, on your terms, week after week, for years.
Decide which numbers actually matter to the work you choose to make, and put your attention there.
🎲 Prompt Playground
The Mid-Year Check-In
This is the part where you can roll up your sleeves and get to work today.
The files I’m sharing below turn everything in this issue into a guided session you run with your AI tool of choice.
Here's the move:
Download the file(s) below. (I’ve included a PDF for easy reading, or a “ready-to-run” markdown file for easy AI ingestion/usage.)
Upload the “ready-to-run” version into Claude, ChatGPT, or Gemini, etc.
Block 30min somewhere you won't be interrupted.
Copy and paste the prompt below to begin.
“Ready-to-run” markdown file → Download the 2026 AI Prompt Library for Breakthrough Planning
Once the file is uploaded, copy/paste this to start:
I've uploaded the 2026 AI Prompt Library. Act as my strategist and run a mid-year check-in with me.
Start with the Mid-Year Quick Start. Work through it one prompt at a time, and ask me your questions one at a time. Don't move on until I've answered.
Push on my assumptions. Tell me where my thinking is soft. Be direct, no hype.
Let's begin.
Don’t feel like downloading? Here’s a no-download path that gets you part way there. Not as in-depth as the full approach above, but still helpful.
Copy/paste this, and let your favorite AI tool run a lightweight check-in with you:
You are a sharp, honest strategist and my thinking partner for a mid-year check-in.
We're going to do a "dead reckoning" on my work: figure out where I actually am at the midpoint of the year, not where I planned to be, and whether my direction still holds.
Run this as a real conversation. Ask me one question at a time, and let my answers shape what you ask next instead of following a fixed script.
When something I say sounds important, unclear, or a little off, follow that thread. Push gently. Reflect my own words back to me.
Cover this ground over the course of our talk, in whatever order the conversation earns:
What I set out to do this year, and what has actually happened since.
Whether the direction I chose is still the right one, given what I know now.
Who I'm really serving today, and whether that has shifted since I started.
How I've been measuring success, and whether that's the right way to measure this particular work.
What I should stop doing to make room for what matters in the back half.
I control the pace. At any point I might say "keep going," "go deeper on that," "pause," or "wrap up." Every few questions, check whether I want to keep going or land it.
When I ask you to wrap up, stop asking questions and give me a direct read: is my direction still right, am I measuring on the right axis, and what is the one thing I should stop doing.
Be direct. No hype. Tell me what I need to hear.
Start by asking me your first question.
⚡ Before You Go
Here are other ways I can help:
🗓️ 1:1 call: Grab 15min on my calendar.
🎙️ Podcast support: Get pro-level guidance without hiring full-time.
🚀 Speaking & workshops: Hit reply, let’s talk.
🤖 AI Prompt Library: 12 prompts to use AI as a strategic thinking partner (same free download from the Prompt Playground section above)
And I’d appreciate your help:
🧶 Take a 2-minute survey to help improve the newsletter.
💬 Leave a short testimonial if this newsletter has helped your work.
Both make a real difference.
Thanks for spending time with Red Threads this week, I’m glad you’re here.
~ Jaime