Never accept less than the love you deserve. Not ever.
If you’re new here — I’m Amanda Carroll, personal dating and relationship strategist for high-achieving women, and a former nationally syndicated radio host. This Substack is your playbook. Every week I hand you one play: a single, named move you study once and then run in your real life. Not a theme. Not a mood. A play. Read it, then go run it.
You can describe your attachment style in three clean sentences.
You’ve read the books. You’ve done the therapy. You can name every pattern you’ve ever run, cite the research behind it, and explain — precisely — why you keep doing the thing you keep doing.
And you’re still single. Still guessing. Still stuck.
Here’s what nobody made you notice: you have answered one question about your love life obsessively, for years. What’s wrong. You have a full report. What you’ve never once answered is the question that actually decides the outcome.
Not “what do you want.” You’ve got that list. He’s successful, he’s emotionally available, he’s tall, he reads.
The question is: how do you want to feel?
Most of the women I coach have never sat down and answered it. Not really.
You’ve diagnosed the problem for years. You’ve never defined the target.
My guest this week handed me a play I had to steal
This week on The Playbook podcast, I sat down with Heather Chauvin, expert on Energy management for women in leadership. She is a former therapist, cancer survivor, and one of the sharpest voices I know on how high-achieving women spend their energy. She does not coach dating. She coaches capacity. And she said something on the record that stopped me cold, so I’m translating her play into ours.
The full conversation drops Wednesday on The Playbook podcast — this is the one move I couldn’t wait to hand you.
I put my client in front of her live on the show. You. A woman in her 40s who runs a department, a practice, or a company. Earns more than most of the men she dates. Done the therapy, read the books, listened to every podcast, can name her attachment style on command — and has been single for years and cannot figure out how to fix it.
Heather’s first move? “Stop going to therapy.”
I know. Sit with it for a second, because a former therapist saying it means something different than a stranger on the internet saying it.
The thing nobody tells high-achieving women
You are excellent at defining the win everywhere else.
You would never launch without knowing what success looks like. You set the metric, then you build the plan, then you execute against the target. That’s how you built everything you’re proud of.
In your love life, you skipped the first step entirely. You went straight to executing — the apps, the dates, the endless analysis — against a target you never defined. So of course it feels like guessing. You’re running a strategy with no scoreboard.
Heather’s clinical read on why smart women stall is worth quoting directly: therapy becomes the comfort zone. Not because it’s bad — because it’s familiar. You go, you talk about the problem, you understand yourself a little more, and you change nothing. As she put it: you’re a perfectionist as a coping strategy, so your brain goes looking for the broken bits. You get very good at the analysis and it quietly becomes a place to hide from the behavior.
That’s not a knock on the work you’ve done. It’s the opposite. You’ve done enough of it. You didn’t have a missing insight. You had a missing target.
You cannot think your way through an emotional decision. You have to aim, then act.
Where this play was born
Heather did not learn this in a seminar. She reverse-engineered it on a bathroom floor.
Pregnant at eighteen, she left a relationship with an addict, decided the whole thing was on her, and did what women like you do — she overachieved her way out. University with a baby on her hip. A career in social work. A business she built before the online space was cool. Every adult around her said look at you, you’re doing so well. Inside, by her own account, she was disappearing.
Then, in 2014, stage four cancer. She was taking client calls from a hospital bed. And one night, mid-panic, she asked herself the only question she had left: how do you want to feel?
The answer came fast — alive — and then the terrifying part landed. She had no evidence. No memory of an identity where she’d actually felt that way. She didn’t know the target, so she’d never once steered toward it.
So she built the map backward. Name the feeling. Then build the life that produces it.
She had read the books, hired the coaches, gone to the retreats — and still found the gap. So she built the framework herself.
If that arc sounds familiar, it should. It’s mine too. Divorced at thirty-four with every external box checked and no framework for the one thing I wanted most. I didn’t need more healing. I needed a system. So did she. So do you.
How you run it
Here’s Heather’s method, translated into strategy you can actually execute.
Write the “wouldn’t it be nice if” list. Don’t start with the intimidating version — what do you want — because your answer is “at this point, I’ll take anything,” and that’s useless. Start soft. Wouldn’t it be nice if I had someone I didn’t have to chase. Wouldn’t it be nice if I didn’t have to be on guard. Let it pour out, unedited, line after line.
The gentlest doorway gets you the most honest data.
Go line by line and pull the feeling. Under every “wouldn’t it be nice if” is a feeling you’re actually after. Connected. Respected. Pursued. Peaceful. Desired. Go down the list and name the feeling beneath each want. Nobody ever writes I want to feel disrespected and chronically exhausted — and yet that’s exactly what a lot of smart women tolerate, because familiar reads as safe to the brain. Naming the real target breaks the loop.
Make the feeling your North Star. This is the strategic part. Once the feeling is defined, it becomes your filter. When a man, a date, a dynamic feels off against it — you trust that, and you use your voice instead of talking yourself out of what you noticed. Not a rule you overthink. A compass you steer by.
Define how you want to feel, and you stop auditioning people who were never going to make you feel it.
Audit your calendar against it. Here’s the one that stings. If you say you want a deeply connected partnership, look at your actual week and ask — honestly — how much time am I investing in that result? Be proactive, not reactive. We’re recording this in July. If you want someone beside you at the holidays, the work starts now, not in a panic in November. Connection isn’t built in a sprint. It’s built in small, deliberate investments over time — which, yes, is exactly the pace high achievers hate. Put the things that make you feel alive on the calendar anyway. What’s scheduled is what’s real.
Become the woman who already feels that way. You don’t wait until you’re “fixed” to start. There’s always a next level — you’ll be building yourself the entire time. Get clear on who you’re becoming twelve to twenty-four months out, start dating as her now, and let the relationship be the place you practice the boundary, the voice, the standard. That’s not healing as a prerequisite. That’s execution while in motion.
What happened to Heather
She married the boring guy.
Her words, not mine — though regular readers know it’s my whole thesis. She met her now-husband a year and a half in, felt no spark, and picked him precisely because he was the opposite of the chaos she used to call chemistry. “You’d make a good dad,” she told him. “I don’t care if I’m attracted to you or not.”
Two decades, two more kids, and one cancer diagnosis later, that “boring” man is the steady ground the whole life stands on. She didn’t lower her standards. She changed what she was aiming for — and then she aimed.
Go for the boring guy. He’s not boring. He’s the one who hands you the remote and asks what you want to watch.
Heather Chauvin hosts Emotionally Uncomfortable and coaches high-achieving women on energy and capacity — find her at @HeatherChauvin on Instagram or HeatherChauvin.com.
This Week’s Play
Reverse Engineer It.
Here’s how you run it.
Step 1 — Today, alone, twenty minutes. Open a notebook. Write your “wouldn’t it be nice if” list about the relationship you want. No editing. Fill the page.
Step 2 — Same sitting. Go line by line and write the feeling underneath each one. Circle the three that show up most. That’s your target.
Step 3 — This week. Open your actual calendar and put two things on it that make you feel one of those three — with or without a man in the picture. Prove to yourself you can generate the feeling before you go looking for someone to generate it for you.
Step 4 — When you’re ready to stop running it alone. Naming the target is the start. Running the framework — the profile, the vetting, the five dates — with a room of women doing the exact same thing is how you hit it on purpose instead of by accident. This week, I’m opening the doors to that room.
→ Join the High Value Women’s Collective. ←
Six months inside the framework — plus live coaching every Tuesday at 1pm ET and Thursday at 6pm ET, where you bring the actual situation (the text you’re not sure how to answer, the date that went sideways, the man who went quiet) and we work it in real time. Can’t make it live? Every session is recorded and yours to keep. It’s a private room of women exactly where you are: accomplished, independent, done doing this alone. $497 for the full six months.
Enrollment closes Sunday so I can welcome the whole group in together on Monday.
That’s the play. Run it.
You built the career. You built the life. You are fully capable of building the love — the moment you aim at it the way you aim at everything else.
Define the feeling. Then direct the strategy.
— Amanda
P.S. The full conversation with Heather is out Tuesday on The Playbook — the bathroom-floor story alone is worth the listen. And this week the room is open: the High Value Women’s Collective is six months inside the framework, live coaching twice a week, and a group of women on the exact same path — for $497, less than most people spend on a weekend away. Enrollment closes Sunday; we start together Monday. You’ve spent enough time figuring this out by yourself. Join here. — Amanda Carroll