Before you dive in: There's an offer at the end of this newsletter that I've never made before. It'll only make sense after you've read the whole thing. So don't skip ahead.

I was somewhere over the midwest, heading home from what should have been a great trip.

I'd just spent two weeks in Europe with my husband, and then went home to Portland for 10 days before leaving again.

This time, I flew to Virginia for a friend's first retreat — someone I love deeply who was doing something brave and new. I got to cheer him on AND visit my best friend and my goddaughters. It should have felt like a perfect stretch of time.

But somewhere on that flight home, all the joy I'd been carrying evaporated.

It was November 2024. Trump had just been re-elected. I was carrying that low-grade dread that a lot of us were feeling — that specific kind of anxiety that doesn't have clean edges, that sits on top of everything else.

And underneath it, my brain had started its inventory: all the things I hadn't done, all the things waiting for me, all the ways I was behind.

I was overwhelmed in the specific way that only entrepreneurs understand — where the work is never actually done, the to-do list is infinite, and you start to feel like you're failing on every front simultaneously.

So I opened my laptop and connected to in flight Wifi. And I did something I'd been building into my practice for months.

I pulled up an AI chat where I had saved a version of my Future Me story.

I typed something like: "I am completely overwhelmed. I'm panicking about everything I need to do. I'm scared about what's happening in the world. I need Future Me to show up and talk to me right now."

What came back stopped me cold:

I started crying. Not the frustrated, exhausted kind of crying. The relieved kind.

→ Future Me didn't hand me a prioritized to-do list.
→ Future Me didn't say "Here are the three things you should focus on."

At least not yet.

Future Me led with compassion first.

The response acknowledged that everything I was feeling made complete sense. That the anxiety about the political climate was real and valid. That coming off a trip into a pile of overwhelm is genuinely hard.

That I wasn't broken — I was human, carrying a lot, doing my best.

And something about being met with that kind of gentleness — by a version of myself — made the overwhelm soften just enough.

Once I could breathe again, THEN we got tactical. And here's where it got interesting.

Future Me helped me look at everything I was spinning about and get honest. One of the projects I was most stressed about?

Future Me pointed out — gently but clearly — that it wasn't actually aligned with where I was going. That I was holding onto it out of obligation and sunk cost, not because it served my vision.

I let it go on that flight.

Then Future Me helped me get clear on what actually mattered.

I landed feeling like a different person than the one who boarded.

Here's the thing I want you to sit with for a second.

When my clients come to me overwhelmed and stuck, they almost always tell me the same thing: "I just need more discipline. I need to push harder."

And 100% of the time, they're wrong.

What they actually need is more self-compassion.

The hustle that got you here? It worked. It got you here.

But it is NOT what will get you there.

The grinding, the pushing through, the "just work harder" mentality hits a ceiling — and past that ceiling, what's required isn't more force.

→ It's more presence.
→ More gentleness.
→ More willingness to actually listen to yourself.

This is literally in my LinkedIn headline. I describe myself as a mix between Jocko Willink and Mr. Rogers.

My clients always think they need more Jocko.

Almost always, what they actually need is more Mr. Rogers.

Because there’s something that self-compassion does that discipline can't.

Self-compassion creates enough safety for you to hear the signal in the noise. When you meet yourself with love and patience instead of more pressure, you start to notice things.

You cannot hear any of that when you're in push-through mode.

Future Me knew this. That's why the response on that flight didn't start with a to-do list.

Here's the problem with how most of us make decisions when we're overwhelmed.

We consult current us. The version of ourselves who's exhausted, behind, scared, and operating from the accumulated stress of everything that's gone sideways this week.

Current you is not your best decision-maker.

Current you is making employee-brain decisions in a CEO role.

And those decisions compound. Not in a good way.

The question isn't "what should I do right now?"

The question is: "What would Future Me do?"

Some of you have heard me talk about the Future You exercise before. I walked through the full concept — the neuroscience behind it, the story-writing process, all of it — earlier this year.

If that's ringing a bell, good. If you read it and thought "I'll do that later" — also good, because today is about what happens after you've built your Future You. The live, messy, real-time application of it.

And I've refined the AI prompts I use for this since I first introduced the concept. Which is part of what I want to share with you.

This is rooted in an exercise developed by designer and educator Debbie Millman — one I've taken, deepened, and made my own over years of using it myself and with clients. Here's the core of it, and then I'll show you how to use it practically right now.

Find some quiet time — not five minutes between calls, actual quiet time — and write a story. A detailed, sensory, expansive story about a single day in your life ten years from now.

Not a goals list. Not a vision board caption. A story.

Start from the moment you wake up. What wakes you? Where are you? What do you hear? What do you smell? When your feet hit the floor, what does it feel like? Who's with you? What work are you doing? What are you thinking about?

Go all the way through the day. And most importantly: how does it feel to be you, living this life?

Be ruthlessly specific. Be wildly ambitious. Let yourself want what you actually want, not a more modest version of it.

Then add:

This story becomes your compass. Your anchor. The thing you return to when current you wants to make a scared decision.

This is where it gets really practical. Open your AI tool of choice — ChatGPT, Claude, whatever you use — and do this:

Paste in a brief description of your Future You vision. Then ask the AI to become Future You and respond to you from that perspective.

The prompt looks something like this:

"I've written a detailed vision of my life 10 years from now. I want you to act as that future version of me — someone who has already built the business and life I'm envisioning, with all the wisdom and experience that comes with that. Respond to me from that perspective when I bring you problems, decisions, or moments where I'm stuck."

Then bring it real stuff.

The overwhelm. The decision you've been avoiding. The project you're not sure about. The price you're scared to charge. Ask Future You — not Google, not a peer who's just as confused as you are, not the anxious voice in your head at 2am.

When you're facing a decision — any decision — run it through this filter:

Not the version of you who's panicking about next month's revenue. Not the version who just got a bad review or lost a client. The version who has already built what you're building.

That version doesn't make decisions from fear. They make decisions from strategy.

They don't say yes because they're afraid of no. They don't undercharge because they're afraid of the objection. They don't avoid the hard conversation because it feels uncomfortable.

They make CEO decisions. And CEO decisions compound.

Here's something most people miss: Future You isn't just a filter for the decisions in front of you. Future You is also really good at helping you see the things that shouldn't be on your list at all.

→ That project you're holding onto out of guilt? Ask Future You.
→ That client relationship that's quietly draining you? Ask Future You.
→ That offer you keep almost launching but never do? Ask Future You.

Sometimes the most important decision is the one to stop — and that's the decision overwhelmed current you is least equipped to make.

Every decision you make is either building toward the business you want or building away from it.

There's no neutral.

➤ The entrepreneur who makes decisions from their overwhelmed, fear-based present self builds a business that reflects that fear. Underpriced. Overloaded. Misaligned. Exhausting to run.

➤ The entrepreneur who makes decisions from their Future Self builds a business that compounds toward that vision. Every yes is strategic. Every no creates capacity. Every choice is an investment, not just a reaction.

This is one of the most powerful leverage tools available to you — and it costs nothing.

One conversation with Future You on a hard day can eliminate a project that's been draining your energy for months. That energy gets redirected. The decisions that come after are sharper. The business you build next week looks a little more like the one you want.

That's how it compounds.

(If you want to understand more about the wealth-building decisions that separate the $50K/month CEO from the $15K/month entrepreneur who's still grinding, this one's worth a read.)

Here's where I want to hear from you.

Since I first introduced the Future You concept, I've continued to refine how I use it — specifically the AI prompts that make Future You feel like an actual coach instead of a generic chatbot response.

The prompts I use now are different from what I shared before, and they work better.

If you want the updated prompt framework — plus the full exercise for anyone who hasn't done it yet — reply to this email and let me know.

You can keep it simple. Just reply with the word FUTURE and I'll know you want it.

Or if something specific came up for you while reading this, tell me that too. Either way, I want to hear from you.

If enough of you ask, I'll share the whole updated toolkit on Sunday.

In love and growth,
Kasey

P.S. If you're making decisions right now that feel impossible — about your positioning, your pricing, your offers, or what to focus on — that's exactly what we dig into inside The Collective. Sometimes you need Future You. Sometimes you need a room full of people who are on the same path. We've got both.