Penny Wrenn Media · Philadelphia
You have decades of judgment and a computer that can finally keep up with it.
I'm Penny Wrenn. I spent twenty years making national magazines. Now I help people use AI to expand their digital footprint and their fingerprint — so the meaningful attention you deserve can finally find you.
Nothing here is gated. Take what's useful and go.Three doors, no email required
What's in the garden
One thing to buy. Two things that are free and actually free — no brochure pretending to be a gift.
The If I Were You Session
$50 · one hourYou leave with an AI-leveraged 3-to-4-month action plan built around your quarterlife — a blueprint for expanding your digital footprint and fingerprint until the right people find you.
Pick a time on my calendar → Free magazine101 Things I'd Do If I Were You
Free · 25-page PDFTen articles, 101 ideas, one quiz, exactly one ask. A whole magazine made with AI in a workweek — for people who've been working longer than the internet has.
Download the PDF → PlayChoose Your Own Adventure
Free · 5 minutesThe career game. Answer honestly, take the turns, find out which of the four Cs you actually are — conscientious, confused, confounded, or curious.
Start the game →The framework
Four quarterlives. Pick yours.
A hundred years, four quarters. The plan I build for you depends entirely on which one you're standing in — because the same advice is malpractice in three of them.
The Setting Out
First quarterlife · 0–25- You have no track record yet — so we build evidence instead of padding a résumé.
- Turn coursework, part-time jobs and side projects into three public artifacts a stranger can find in ten seconds.
- Learn the AI workflow now, while nobody expects you to already know it. That head start compounds for fifty years.
- Practice the ask. Most people your age are waiting to be picked. You're going to send things.
Three to four months out: a searchable name, one portfolio piece you're proud of, and one grown-up ask you've actually sent.
Build my first-quarterlife plan · $50The Building
Second quarterlife · 26–50- You have proof — it's just scattered across old employers, dead links and folders nobody can see.
- Consolidate a decade of work into one findable place that argues for you while you sleep.
- Use AI to raise your return per hour, not your output per hour. Volume is not the goal. Leverage is.
- Name a price you can say out loud without your voice going up at the end.
Three to four months out: a clear offer, a live pitch list, and a rate that doesn't sound like a question.
Build my second-quarterlife plan · $50The Reckoning
Third quarterlife · 51–75- You have more judgment than the market currently knows how to price. That's a packaging problem, not a you problem.
- Translate twenty-five years of pattern recognition into something a person can actually buy.
- Treat AI as leverage, not threat — it has never sat in the room where it went wrong. You have.
- Rebuild a footprint that reads as in practice, not as winding down.
Three to four months out: a named practice, a first paid engagement, and a public presence that doesn't apologize for your age.
Build my third-quarterlife plan · $50The Handing Down
Fourth quarterlife · 76–100- Legacy is a documentation problem before it's a sentimental one.
- Get the stories, the records and the know-how into a form that outlasts a hard drive and a password nobody has.
- Let AI do the transcribing, sorting and captioning so you can do the remembering.
- Decide what has your name on it — and put your name on it.
Three to four months out: an archive your family can actually open, organized the way you'd want it explained.
Build my fourth-quarterlife plan · $50The one thing I sell
The If I Were You Session
One hour, one human, one plan. We look at where you actually are, and I tell you — plainly, the way I'd tell a friend — what I would do if I were you.
You leave with an AI-leveraged 3-to-4-month action plan keyed to your quarterlife. Not a worksheet. Not a webinar funnel. A sequence of specific things to make, send, publish and ask for, in an order that builds on itself, using tools you already have access to.
It's a blueprint for expanding your digital footprint — what people can find — and your fingerprint — what only you could have made. Both, on purpose, so the meaningful attention you deserve knows where to land.
It's built for the four Cs:
- career-conscientious
- career-confused
- career-confounded
- career-curious
"Right, but for my situation…" — good. That sentence is the whole reason this session exists.
On the house
Take something on your way through
Six things you can do this week without me, without paying anyone, without permission. If you only ever visit this page once, leave with these.
Google yourself in an incognito window. Screenshot page one. That's your résumé now — it's the one the robot reads first.
Paste your last three job descriptions into an AI and ask it one question: "What am I selling here that I'm not charging for?"
Write one sentence that says what you do without naming your job title. Put it in your LinkedIn headline before you close the tab.
Find the longest email you wrote this month. Ask an AI to turn it into a 200-word post. You already did the thinking — collect on it.
List ten people whose work you admire. Send one an unsolicited, specific, useful note. No ask attached. That's the whole exercise.
Say your price out loud, to a wall, until it stops sounding like a question. Then say it to a person.
Get the 101 magazine
Ten articles, 101 ideas, a quiz and one ask. Take the PDF with you — or read the designed issue in your browser at pennywrenn.media.
Download the PDF → Free · 5 minPlay the adventure
Choose your own career adventure. Every path ends somewhere useful, which is more than can be said for most careers.
Start the game →Who's telling you this
Penny Wrenn
I've been a magazine editor for most of my working life — Essence, Esquire, Redbook and O, The Oprah Magazine, plus Glamour and a good many others.
I know exactly what an issue costs in people, in months, in meetings. That's why I take the AI part seriously rather than sentimentally: the distance between knowing better and doing better just collapsed, and I'd like you to be standing on the right side of it.
Outside the magazines, the work has been stubbornly practical: digitizing and updating an archive at WebMD; doling out financial advice to twenty- and thirtysomethings at LearnVest; teaching digital literacy in Montessori classrooms for an edtech company; working with an operator of caregiver services; and helping a health-tech company bring vision care into community health centers.
I'm a graduate of Spelman College. I live in Philadelphia, in Roxborough–Manayunk. I substitute-teach in the School District of Philadelphia, which keeps a person honest.
Penny Wrenn Media is the venture all of this now runs through.
Four essays, four subjects
Love, legacy, livelihood and lethargy. Twenty years of writing, roughly summarized.
- Twenty-plus years in national magazine editorial
- Digital leadership at WebMD and LearnVest
- Spelman College graduate
- Philadelphia — Roxborough / Manayunk
Keep wandering
Elsewhere in the garden
Other things I've built and keep building. All live, all free to walk through.