Career coaching, whatever stage you're at

You're better at your job than you are at describing it.

Penny is a career coach that helps you find the words for what you actually do well — then put them to work. Between roles, quietly looking, or just wondering where you are at your best.

3-day trial period · $29 a month after · Cancel any time
Session one
Strengths
Before we touch your resume — tell me about a week at work when you felt genuinely useful.
Probably when the platform migration was falling apart and I ended up running comms between three teams.
That isn't "comms". That's holding a cross-functional program together under pressure. Let's find three more like it — then we'll write it down properly.
Where you are right now

Same starting point. Three different journeys.

Everyone starts the same way. Penny walks you through your lived experiences, professional and personal, and names the strengths she finds — usually in the chapters you would never have put on a resume, because the hardest ones hold the clearest evidence.

That correlation is the hard part, and it is close to impossible to make on your own. Adversity gets filed as damage rather than evidence. Shame keeps the worst chapters closed, so the places holding the clearest proof of what you are good at are the last places you would think to look.

The migration nobody wanted to own so I handled it for 6 weeks while holding 3 teams together that had stopped speaking to each other.

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Crisis communication · Cross-functional coordination · Initiative

The racism I grew up with, before I had a word for it, helped me support my colleagues today who are treated blatantly different.

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Situational, cultural, & self awareness · Kindness

The restructure. Supporting the team's anxiety & stress while my own job was under review.

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Composure · Compassion · Empathetic leadership

Examples. Yours would be your own.

Between roles

I need to find something, and soon.

A resume that lands, and a search with a rhythm instead of a grind.

In a job, looking

I want out, quietly.

A shortlist of six roles, and a way to work it around a full-time job.

In a job, wondering

I want to know where I'm at my best.

An honest read on whether the answer is a move, a conversation, or staying put.

Why it's hard

It can be hard to describe what you're good at.

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You did the work. Articulating it is a separate skill, and nobody ever taught it to you.

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Advice is everywhere. None of it is tuned to you as an individual — to the strengths you actually have, or to the career, the field and the role that would genuinely fit them.

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It's never the right week. Either you're too busy to think about it, or you're job-hunting so hard there's no room left to think at all.

Your skills summary

The document everything else is built from.

Every line names a skill and the moment it came from, in your own words. It runs long on purpose and keeps going for as much as you are willing to share and learn about yourself. This is why nothing is generic. An authentic reflection of who you are.

Your skills & strengths summary

Everything here is rooted in what you actually lived — not a generic list.

Soft skills

Crisis communication When the migration was falling over and three teams had stopped speaking to each other, you were the one moving information between them. Six weeks of it. Nobody assigned you that.

Holding a team steady You absorbed the pressure your team could not control, and told them the truth about what you could and could not change. That is why they stayed.

Technical skills

Cross-functional program delivery You ran a live platform migration across three engineering teams without formal authority over any of them.

Character strengths

Resilience under pressure You worked for a year under a manager whose mood set the weather. You did not harden. You got better at reading a room.

This is a short extract. A real summary runs far longer — it keeps going for as much of your life as you walk through with her.
Your why

You know what it costs when nobody is holding the middle. You have spent your career making sure somebody is.

An example. Yours would be built from your own experience.

Meet Penny

Hi, I'm Penny.

I'm not a person — I'm software. What that buys you is a coach available at 11pm on a Sunday, who never tires of your third draft, and who has no stake in what you decide.

My job is to walk you through what you've actually done, in a psychologically safe way, until you can say what you're good at without hedging.

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Grounded in positive psychology and organizational behavioral psychology
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Available whenever the doubt turns up, which is rarely office hours
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Built by Yen, who founded Sirius Stuff after twenty years running teams
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The framework comes from her master's thesis in Spirituality and Psychology at Teachers College, Columbia University — a framework for surfacing soft skills and strengths

Penny is not a substitute for a career coach. She is what you bring to one — or to an interview, or to the conversation you have been putting off.

What makes Penny different
What's included

Everything a good coach would do, on your schedule.

What you see
When Penny connects the dots
THE LAYOFFRESTRUCTURETHE MIGRATIONCAREGIVING YEARHolds steady under pressure

Strengths profile

Not a personality quiz. A picture of what you do well, built from what you have actually done.

CV, resume, and LinkedIn language

Written with you, in your unique voice, for the roles you're going after. Nothing about this is generic.

Practice before it counts

Practice the answer you keep fumbling, as many times as you need, without burning a favor.

As often as you need

Come back the night before an interview, or three weeks later. Every conversation starts fresh — you bring the summary, and it picks up from there.

Skills you never thought to name

Soft skills and technical skills you have been using for years without a word for them. Penny names them, and tells you which ones are rarer than you assume.

Evidence, not adjectives

Every strength is tied to the experience that produced it, so you can back it up in a room rather than simply claim it.

It starts with being able to say what you're good at.

Start with one conversation. If it isn't useful, cancel before you're charged again.