Coaching session with Penelope

Here’s how a session goes. You’ll bring me a question — should I quit, should I move, should I get divorced, should I spend the savings, should I write the book, should I homeschool the kid. And I’ll spend most of our hour ignoring the question you asked, because the job is almost never the job and the marriage is almost never the marriage. The question you walked in with is usually a decoy you built to keep yourself from deciding. I’ve spent thirty years taking those apart. You’ll leave knowing what you’re actually choosing between, what I think you should do, and why. Sometimes my answer is the one you were hoping for. More often it’s the opposite. Either way you’ll understand it, which is more than you can say for all the advice you’ve been collecting to avoid deciding.

What people book me for

I don’t know what to do next. You’re successful enough to keep doing what you’re doing and unhappy enough that you don’t want to. Maybe AI ate your industry, maybe your company got acquired, maybe the kids left, maybe you’re fifty and just realized you could do almost anything — or that you don’t want to. This is my favorite conversation, because you can’t see the answer from inside your own life, and I can.

I want to write, but I don’t know what to say. You don’t have writer’s block, you have self-protection. The interesting thing you want to write is hiding behind the polished, professional, safe version that nobody reads. I’ve spent twenty-five years making a living writing the sentences other people were afraid to write, and I can find the one you’re avoiding.

My career isn’t working. People ask for help presenting themselves differently – in a resume, an interview, LinkedIn. Sometimes that’s the work. More often the resume is fine and the real problem is that you built a career around someone else’s definition of success. Once you see that, the practical pieces get easy.

I’m worried about my kid. Bright and stalled — graduating into a world where no one trains anyone, choosing a major, choosing a career, recovering from a false start. Parents don’t know how to help because no one helped them do this either. Often the most useful thing I do is get a parent to stop solving the wrong problem.

What it’s like to work with me

The most common unspoken thought in a therapist’s office is just tell me what to do. A therapist won’t, because that’s not the job. I will, because that is the job. I’m not going to ask how it makes you feel or hand you a worksheet. I listen very closely — closely enough to hear the thing your defenses are already moving to cover — and then I tell you what I think. If you want reassurance that you already made the right call, I’m the wrong person. I’m who you call when you want the true thing said out loud, faster than you can talk yourself out of hearing it.

“People call her blunt, but what’s really happening is she says the true thing faster than your defenses can block it. I’ll take that over the self-help that tells you your life is hard because you’re just too generous and selfless.”

Why me

I’ve spent most of my life making decisions people thought were reckless. I started companies and closed companies. I got divorced, remarried, moved across the country twice, homeschooled my kids from first grade, and went back into research in my fifties. Some of it worked beautifully and some of it didn’t, and living through both is the thing no framework can teach you. Inc. called me the world’s most influential guidance counselor. My authority isn’t that I always chose right — it’s that I’ve lived through the consequences of the times I didn’t, which is exactly what lets me tell the difference between fear and information when you can’t.

“I booked a call at the start of the pandemic and it was so harsh I swore her off and badmouthed her to everyone for years. She’d told me I was mistyped, and that I’d be happiest leaving my business to be home with a kid. We had the child. Now I don’t want to go back to work — and she was right about every part of it.”

One session

Most sessions are an hour, and most people only need one. I don’t sell packages and I won’t book you for ten sessions while you stay hesitant. I get to the core problem fast, and once you can see it, what to do is usually obvious — you were never confused about your options, you were confused about which decision you were actually making. That takes one good conversation, not a program.

 

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Coaching session with Penelope

Instructor

Penelope Trunk

Penelope Trunk has been writing online and coaching professional writers for more than a decade. She has published 5 books, and had her advice syndicated in more than 200 newspapers. Penelope taught writing at Harvard, Brown, and the University of Paris. 

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