Pasta, Purpose, Plan — A 7-Day Italy Retreat for Corporate Women | A Sharp Coach
Villamena villa, Umbria

Pasta,
Purpose,
Plan.

Get clear on life after corporate —
and whether coaching is your calling

Villamena · Umbria, Italy

Umbria, Italy · August 26 – September 1, 2027

Reserve My Spot Not sure yet? Book a coffee chat with Alyssa →

If you're a high-achieving corporate woman who knows something needs to change — you're just not sure yet what that looks like, or whether coaching could actually be your ticket out.

This is seven days in the Italian countryside to find out.

Between identity coaching sessions, long meals, and good wine, you'll get clear on who you're becoming, whether coaching is your next chapter, and what your first real steps look like if it is.

Imagine…

It's the second evening.

You're sitting at a long table outside, the kind that takes twenty minutes to set because there are too many dishes to fit at once. The wine is already open. Someone across from you just said something that made the whole table laugh, and you realize you haven't thought about your inbox in three hours.

Stone courtyard at Villamena, golden hour
Women sharing wine at dusk on the Villamena terrace

The hills are going gold. Dinner is coming out in courses. You don't have anywhere to be.

And somewhere between the pasta and the second glass of wine, a thought settles in — quietly, clearly: I know what I'm doing next.

That's what this week is designed to give you. Not a vision board. Not a five-year plan you'll abandon on the flight home. A decision you can actually trust, made in a place that gave you the space to think straight.

Panoramic Umbrian landscape, rolling hills and vineyards

That's what Pasta, Purpose, Plan is built for.

Sounds like exactly what you've been waiting for? Let me tell you what we've created for you…

What Becomes Possible

If you're reading this, you've probably already tried the logical next step. The promotion. The side project. The weekend away that was supposed to reset you. And you're still here — which means none of it touched the actual problem.

You're not stuck because you're not capable. You're stuck because you haven't stopped long enough to hear yourself think.

Burnout disconnects you from yourself. This retreat brings you back.

You're not running on empty because you're weak. You're running on empty because you've been optimizing for everyone else's definition of success for so long, you've lost track of your own. This week gives you the space, the stillness, and the structure to come back to yourself. Not the version holding everything together — but the woman underneath that.

Woman at peace on the terrace, sunlight on her face
Woman gazing at Umbrian hills, contemplative and free

What if you left Italy not just inspired — but so clear on who you're becoming that going back to the old life felt genuinely unthinkable?

When you know who you are, you stop tolerating a life that doesn't match her.

Not because Italy was beautiful — but because you finally made a decision about yourself that you actually trust.

Fear of failure is rarely about the business. It's about what it means about you if it doesn't work.

Your identity as a capable, worthy woman isn't on the line here. We'll make sure you know that.

We do the identity work that separates your worthiness from your results — so you can move forward not because the risk disappears, but because your belief in yourself is finally stronger than the fear.

Small group session in the garden, warm and connected
Woman journaling in the morning light, coffee beside her

The story that says you're not enough, not ready, not qualified — we look at it directly. And we build a new one.

You don't need more time, more credentials, or more proof. You need to decide who you are. That's what we do here.

Grounded in evidence and your own lived experience, you'll leave knowing yourself as a coach. Not just wanting to be one. That internal shift is what makes everything else possible.

You'll define your niche, shape your offer, and stop second-guessing your expertise.

Confidence in your offer begins with confidence in yourself. You'll leave knowing both.

Because when you understand yourself clearly, you know exactly who you were built to help.

Alyssa coaching 1:1 on the terrace, Italy backdrop

You're not stuck because you're not ready. You're stuck because you haven't had the space, the clarity, and the right support — all in the same place, at the same time.
That's what this retreat is.

Where We're Going

Villamena, Umbria

Villamena is a charming 19th-century retreat nestled amidst the rolling green hills of Umbria — just 5 km from Assisi, the city of San Francesco. This historic residence is a place where the pace of life slows and everything unnecessary falls away.

You'll gather in a large indoor Refectory dining hall, linger over quiet reflection on the panoramic terrace, and unwind by the pool between sessions. Each apartment has been thoughtfully renovated using traditional materials and period furnishings — and features its own private garden where you can enjoy meals al fresco.

Modern comforts, ancient walls, and a warmth that wraps around you the moment you arrive.

Villamena villa exterior Panoramic view from the terrace Villamena terrace Villamena apartment interior

The Table

Food That Tastes Like Italy

Welcome to Pasta, Purpose, Plan, where every meal is a celebration of connection and flavor set against the stunning backdrop of Italy's Umbrian countryside. Picture yourself dining al fresco at our large communal table, where the lively, social atmosphere invites you to share stories and laughter with new friends.

In Umbria, the food is rustic, earthy, and deeply rooted in tradition. You'll savor dishes crafted from the region's prized black truffles, expertly prepared pork, and hearty mountain legumes — the "green heart of Italy" on your plate.

Your day begins with a delightful buffet-style breakfast: pastries, eggs, freshly brewed coffee, tea, and orange juice. Lunch is light and fresh. As the day winds down, dinner becomes a comforting celebration — fresh-made pizzas, local specialties, a glass of regional wine, and the people who are quickly becoming your people.

We accommodate all dietary needs — vegetarian, gluten-free, and beyond. Just let us know when you register.

Communal table at Villamena Italian cuisine Wine and aperitivo Umbrian food spread Fresh pasta and local ingredients

Your Week

The Journey, Day by Day

August 26 – September 1, 2027 · Click each day to expand

Arrive, settle in, and breathe. Leave the weight of your everyday life at the door. You'll have the opportunity to connect with your fellow participants, setting a foundation of camaraderie for the week ahead. With intentions thoughtfully set, you'll feel relief and relaxation wash over you — grounding you in the present moment and preparing you to embrace the transformative days to come.
Through guided visualization, you'll connect with your future self — the version of you who has already made this leap. You'll dive into an expansive realm of possibilities, where dreams feel tangible and decisions are made with clarity. You'll discover that the secret to rapid success lies in embracing this future version of yourself.
The morning begins with a bold exploration of your personal definition of success. You'll engage in expansive goal-setting exercises that challenge conventional limits, daring to envision a life that excites and inspires you. You'll redefine what it means to be successful — granting yourself permission to aspire to a life that aligns with your true desires.
Today, you'll delve into the practical aspects of building your coaching dream. You'll gain clarity on identifying your niche, understanding its significance, and learning how to avoid common pitfalls. This exploration brings a sense of certainty to your path — empowering you to know exactly whom you want to help and how to meet their needs.
Today, you'll focus on designing an irresistible coaching offer tailored to your niche — a program that excites both you and your potential clients. As you build this offer, you'll gain confidence in your ability to lead your ideal clients on a transformative journey. This critical step solidifies your vision of transitioning from your current career to a fulfilling coaching practice.
On this pivotal day, you'll revisit the identity work that began your journey. With a clear understanding of your niche and offer, you'll practice embodying the successful, confident coach you aspire to be. We'll also introduce strategies for promoting your services and finding clients — so you leave ready to speak about your coaching journey with assurance.
As the retreat comes to a close, you'll gather with newfound friends to reflect on your journey. We'll support you in setting actionable intentions and goals for the next 30, 60, and 90 days — ensuring that your transformation continues beyond this experience. With a heart full of motivation and newfound confidence, you'll depart ready to begin the next chapter of your coaching journey.

What You'll Come Away With

Strategy. Identity. Both.

Most retreats give you time to breathe and a yoga routine. This one gives you strategy AND the internal foundation to actually use it. Because here's what most programs miss: you don't just need a plan. You need to become the woman who executes the plan.

Group session at Villamena, women engaged and energized

You'll know yourself outside of your title.

Through guided reflection and identity work, you'll get clear on who you actually want after corporate — not just what looks good on paper, but what's true for you. You'll leave moving forward with real direction, self-trust, and quiet conviction.

You'll stop looking outward for permission and start leading from your own inner knowing.

You'll stop feeling like leaving is betraying your past.

Through future self integration and honest coaching conversations, you'll reframe leaving your career as the most aligned decision you've ever made — not a rejection of your past, but a powerful reclaiming of who you're becoming.

The woman who built a corporate career and the woman building a business are both you — and here, you'll learn to own both fully.

Alyssa in session with the group, energy and warmth

Days later, I'm still thinking about all the breakthroughs I experienced in my time with Alyssa. She helped me look at places in my life where I feel stuck around finances and how to shift into a different perspective. After our session, I felt invigorated and inspired to try new things in my business. For anyone who's on the fence about working with Alyssa to connect with your future self, I'd highly recommend you take the leap and see how she can help you discover your own breakthrough.

Taylor

Villamena pool and garden at golden hour
Woman with notebook, confident and clear on her direction

You'll know your niche — and own your expertise.

Through niche work and offer development exercises, you'll define your ideal client and craft an offer that feels like an honest extension of who you are. You'll stop second-guessing your value and start owning your expertise — because when you understand yourself clearly, you know exactly who you were built to help.

Confidence in your offer begins with confidence in yourself. You'll leave knowing both.

You'll have a real first step — and the belief to take it.

Through focused business mapping and self-efficacy work, you'll identify the right first steps and build the internal confidence to take them. Not just a to-do list — an identity shift that makes the plan stick.

Strategy without self-belief stalls. Here, you build both.

Working with Alyssa has been incredibly eye-opening. I had convinced myself that I needed to wait until I received my ICF credential before I could start. Alyssa helped me realize that I don't need to wait for the credential to begin. She encouraged me to take action now, and that shift in mindset has been truly empowering. I'm so grateful for her guidance and support.

Li-Wen · IT Manager turned Life Coach

You'll know how to show up online — as yourself.

Through visibility coaching and identity work, you'll build a real sense of self-assurance that translates directly into how you present yourself. Not a persona. Not a script. You — clear, grounded, and recognizable.

The most magnetic thing you can show up as online is the most honest version of yourself. That's what we uncover here.

You'll come home as yourself again.

Surrounded by beauty, good food, and spacious time, through guided restoration and reconnection, you'll reset your mental load and come back into contact with yourself — not the version running on fumes for everyone else, but the woman underneath that.

Burnout disconnects you from yourself. This retreat brings you back.

Women walking through Assisi, joy and belonging

I was feeling like I was going in circles, not knowing where to begin or how to do a lot of backend work for my business. Alyssa lays it all out to help you realize your goals sooner and do so in alignment with your favorite version of yourself. Her energy, knowledge, and experience were abundantly clear. And then she went above and beyond all my expectations. Her enthusiasm to help me reach my goals has kept me going even on days I struggle to summon my own belief.

Erin F. · Parent Coach

Don't Just Take My Word For It

Hear From the Women Who've Done the Work

Questions

Everything You're Wondering

Honestly — this is often exactly who this retreat is designed for. Many of the women who come have spent months (or years) circling the question. The retreat isn't built on the assumption that you've already decided — it's designed to help you get clear on whether coaching is genuinely your path, and what that looks like if it is. You'll leave knowing. Not just wondering.
This retreat is intentionally intimate — capped at 15 women. You'll know everyone's name by the end of day one. That's not a logistical detail. That's the design.
Umbria is one of the safest, most welcoming regions in Italy. And you won't be navigating this alone. You'll fly into Perugia Airport (PEG) — a small, easy airport about 30 minutes from Villamena. We'll send you complete transfer instructions, and by the time you board your flight, you'll already know your fellow participants from our pre-retreat group call. Women who have never traveled solo internationally have done this — and it becomes one of the things they're most proud of.
Consider what another year in a career that's costing you your health, your time, and your sense of self actually costs you — not in dollars, but in you. This retreat is a week that changes the trajectory of what comes next. The return isn't measured in what you spend. It's measured in who you are when you leave Italy.
None. This retreat is not for certified coaches looking to advance their practice — it's for women who are still becoming coaches. The credential comes later. The identity shift starts here.
Yes. You can pay in full at registration or spread your payments monthly, with your full balance due July 25, 2027. Both options are available at checkout. Paying in full also unlocks the Private Pre-Retreat Identity Activation bonus.
We understand life happens. See our full cancellation policy below. We strongly recommend protecting your investment with travel insurance — we suggest Faye Travel Insurance, where you can choose from several policy options.

Everything You Need to Know

What's Included

Included for Every Participant

  • 6 nights at Villamena (August 26 – September 1)
  • 3 meals per day — breakfast, lunch & dinner
  • All coaching sessions & group workshops
  • Wine tasting experience
  • Cooking class
  • Cultural experience [TBD]
  • Pre-retreat group call
  • Post-retreat integration call
  • Private retreat community group

Not Included

  • International airfare
  • Travel insurance (strongly recommended)
  • Ground transport to/from Perugia Airport
  • Spa treatments or personal services
  • Personal shopping or excursions outside the program
  • Tips for venue staff
  • Any meals or beverages beyond those listed

VIP Experience

Your own room.
Your own space.
Your own session.

For the woman who needs to fully exhale to fully receive this.

  • Guaranteed private room at Villamena
  • VIP Private Future Self Session with Alyssa
  • VIP Aperitivo — an intimate evening in Italy
  • One curated Italy welcome gift
Claim a VIP Spot

Getting Here

Fly into Perugia Airport (PEG) — a small, easy-to-navigate airport approximately 30 minutes from Villamena. Complete transfer and logistics information will be sent upon registration. We recommend arriving by early afternoon on August 26 to allow time to settle in before our opening evening together.

Investment & Registration

Choose Your Experience

⏰  Early Bird pricing ends June 25, 2027 — or when 8 spots are claimed, whichever comes first

Save $1,000 when you book before the deadline.

The Retreat

Shared Apartment
7 Days in Umbria

Early BirdRegular
$5,495$6,495
  • 6 nights at Villamena
  • All meals, workshops & experiences
  • Pre & post-retreat group calls
  • Private community group

VIP Experience

Private Room
+ Private Session + Aperitivo

Early BirdRegular
$6,995$7,995
  • Everything in Retreat
  • Guaranteed private room
  • VIP Private Future Self Session (1:1 with Alyssa)
  • VIP Aperitivo with Alyssa
  • One curated Italy welcome gift

Pay in Full Bonus — Private Pre-Retreat Identity Activation

When you pay in full (either tier), you'll receive a private 60-minute session with Alyssa before you ever board your flight. Together you'll identify what you're ready to leave behind, define the version of yourself you're stepping into, and create your personal "Italy identity" for the week. Then, when you arrive at Villamena — a bottle of Italian wine and a handwritten note will be waiting in your room.

Pre-Retreat Identity Activation Italian wine on arrival Handwritten welcome note

A $500 deposit secures your spot. Full balance due July 25, 2027.
Payment plans available at checkout — pay monthly with balance due by that date.

Still deciding? Book a coffee chat with Alyssa →

Cancellation Policy

A $500 deposit is required at time of registration. Deposits are refundable until 150 days before departure. Less than 150 days before departure, deposits are 100% non-refundable.

  • March 26 – May 26, 2027: Cancellations result in a loss of 50% of the total trip price.
  • May 27, 2027 – departure: Cancellations result in total loss of funds.
  • We reserve the right to cancel the trip if it does not meet the minimum. In that event, your deposit is refunded in full.

Trip cancellation insurance is strongly recommended. We suggest Faye Travel Insurance — choose from several policy options online.

Be Sure

Is This Retreat For You?

This journey is
totally for you if…

  • You're a corporate woman who knows something has to change — even if you're not 100% sure what yet
  • You're ready to stop waiting for the "right time" and start making intentional moves
  • You believe work can feel meaningful AND pay your bills
  • You're willing to do honest inner work alongside the strategy
  • You're open to connecting with a small, intimate group of women on the same path
  • You're both excited and a little nervous about this trip — which tells you it's exactly right

This journey is
not for you if…

  • You're not willing to look honestly at the stories you've been telling yourself
  • You want a passive vacation without reflection or real work
  • You're not open to the possibility that the answer might already be inside you
  • You're looking for someone to hand you all the answers without doing your own inner work

Who's Leading This Retreat

Alyssa Sharp, founder of A Sharp Coach

I'm Alyssa Sharp.

I was at a black-tie event in New York City — the kind of night that's supposed to feel like arrival — and I remember standing in the middle of it thinking: is this it?

I had the career. The title. The trajectory. I was good at it, genuinely. But the moments that actually lit me up weren't in the boardroom. They were in the quiet, one-on-one conversations with people on my team who were trying to figure out what they really wanted. That's where I felt like myself.

I grew up in Elyria, Ohio — part city, part country, all practical. My parents divorced early. I was a caretaker for my older sister, who has cerebral palsy. I learned to be responsible, capable, and self-sufficient before I had language for any of it. I built a corporate career on exactly those traits. And for a long time, that felt like enough. That felt like success.

It wasn't.

Leaving wasn't a clean leap. It was a decision I made slowly, then all at once — the way most real decisions actually happen. What I found on the other side wasn't just a different job. It was a different relationship with myself. And that's the thing I couldn't have predicted: how much of the work was identity work, not strategy work.

That's what I do now. I help 6-figure corporate women who are done waiting build a coaching business and leave — not by handing them a plan, but by working at the level where the real block lives. Who you believe you are. What you think you're allowed to want. Whether you trust yourself enough to bet on it.

Italy is where I bring women for this work because Italy doesn't let you stay numb. The food is too good. The pace is too human. The hills at dusk are too insistent. Something about being there makes the question you've been avoiding a lot harder to ignore.

If you're reading this page, you already know something needs to change. You're not here by accident.

Join Me in Italy

Because We Believe in Your Success Beyond Italy

What's Included With Every Registration

💬

Pre-Retreat Group Call

Meet the group before you land. Share your intention, ask questions, and learn how to best prepare for the week. You'll board your flight knowing people.

🤝

Private Retreat Community

Connect before, during, and after Italy. Ask questions, share wins, swap photos. The relationships that form here tend to outlast the retreat itself.

🌱

Post-Retreat Integration Call

Gather again 4–6 weeks after Italy to celebrate progress, integrate your learnings, and stay on track. The retreat ends. The transformation doesn't have to.

✨

Pay in Full Bonus:
Pre-Retreat Identity Activation

A private 60-minute session with Alyssa before your flight — to identify what you're leaving behind, define the woman you're stepping into, and set your personal Italy intention. Plus: a bottle of Italian wine + handwritten note waiting in your room on arrival.

🍷

VIP: Private Future Self Session

A private 60-minute session with Alyssa held somewhere beautiful on the Villamena property — terrace, garden, or poolside — with coffee or wine. Dedicated space for the identity shift you're here to make, in a setting worthy of it.

🌅

VIP: Aperitivo with Alyssa

An intimate evening gathering with Alyssa and your fellow VIP participants. Wine, conversation, the Umbrian hills in the background. The most Italy-coded thing we could think of.

Your Next Chapter Is Waiting

Fifteen women. Seven days.
One ancient Italian hillside.

And the version of yourself you've been circling for years — finally ready to land.

Still have questions? Book a coffee chat with Alyssa →

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