My Speaking Challenge
Sixty days · One city · Sixty conversations

Stop studying English.
Start speaking it.

A sixty-day speaking challenge through Chicago. Real situations — clearing customs, ordering coffee, disagreeing at dinner, giving a toast. Scored, instantly, by Vox.

See the journey

A1 challenges are free. Unlock further bands for $9 each.

The challenge

Sixty real conversations. Not sixty grammar lessons.

Real situations, not drills

Every challenge is one encounter on a sixty-day trip — booked, lived, scored.

You speak. Vox listens.

Every response is recorded and rated for fluency, pronunciation, grammar and vocabulary.

Built for adults

No cartoon owls. No streaks for streaks' sake. A graphic-novel world that respects you.

Your double

You're not playing yourself.

Pick a protagonist on day one. You'll spend sixty days inside their head — arriving, fumbling, finding your feet, becoming someone in the room.

Marco Rinaldi

Marco Rinaldi

28. Junior Product Analyst from Milan. Sharp in Italian. Nervous in English. Just landed in Chicago for a sixty-day placement at the company's downtown office.

Marta Conti

Marta Conti

28. Junior Product Analyst from Milan. Sharp in Italian. Nervous in English. Just landed in Chicago for the same sixty-day placement. Marco's twin in every way that matters.

The journey

Six bands. Sixty days. One city.

Each band is ten challenges — ten encounters on the trip. You start at A1 with passport control; you finish at C2 giving the toast.

A1

Arrival

Days 1–10 of 60

Welcome to Chicago. Before any of the work begins, you have to land, get through the airport, and turn a hotel room into somewhere that feels like yours. These first ten days are pure arrival — the small, ordinary exchanges a guidebook never mentions, the ones that quietly decide whether a new city feels survivable.

By Day 10 you can hold your own across a counter, a desk, a sidewalk. Not fluent — functional. The nervous half-second before you speak is still there. That's fine. It's supposed to be.

A2

Finding Your Feet

Days 11–20 of 60

Arrival is over — you've got a room, a routine, a coffee place. Now the city itself opens up: the trains, the museums, the food, the small daily logistics a tourist never has to solve. Ten days of moving through Chicago like it's starting to be yours.

By Day 20 you can move around the city on your own — buy what you need, ask what you don't know, hold an exchange that isn't just a transaction. Still translating, still a half-step behind. But finding your feet.

B1

Into the Evenings

Days 21–30 of 60

Three weeks in. The daytime city is handled — now the evenings ask something harder. Not transactions: conversation. Recommending, disagreeing, telling a story, holding your end of a room. These ten days are the social city — where English stops being a tool you use and starts being a way you are known.

By Day 30 you can hold your own in a conversation that has no script — disagree, joke, recommend, decline, all without rehearsing. Still translating, sometimes. But in the room, not just surviving it.

B2

Friction

Days 31–40 of 60

Five weeks in, and the city stops being easy. Things go wrong — a charge you didn't make, a plan that falls through, a conversation that sours. These ten days are about handling trouble in English: complaining without losing your temper, repairing a misstep, making your case, holding steady when someone else isn't. Not surviving the city — managing it.

By Day 40 you can handle things going wrong without going quiet — push back, repair, negotiate, de-escalate, and still leave the room intact. Pressure doesn't shrink your English anymore.

C1

Higher Stakes

Days 41–50 of 60

Seven weeks in. You're not getting by anymore — you're someone in the room. Ten days that ask for finesse: leading a conversation, asking a hard favour gracefully, challenging a view without bluntness, telling a friend the truth kindly, marking a moment with the right few words. English as something you wield, not just use.

By Day 50 you can shape a room, not just hold a place in it — lead, challenge, welcome, and tell a hard truth gently. English has become a way you carry yourself.

C2

Mastery

Days 51–60 of 60

The last ten days. You arrived sixty days ago unable to order a coffee without rehearsing it. Now the city asks the hardest things of you — persuade a skeptic, mediate a fight, hold your ground, mend something broken, and at the end, stand up and send the whole trip off in a few words. English isn't something you're learning anymore. It's something you do.

By Day 60 you can do the hardest things a conversation asks — persuade, mediate, defend, repair, and rise to a moment in front of everyone. You came to learn English. You leave having become someone in it.

Scored by Vox

Every word, rated.
Every challenge, a verdict.

You record. Vox listens. In seconds you get a CEFR-level read on what you actually said — and where to push next.

Vox heard a B1-level response.
Fluency82
Pronunciation76
Grammar68
Vocabulary71

Pricing

Pay for the band, not a subscription.

A1 is free. Unlock further bands one at a time, or grab the full Chicago path at a discount.

One band

$9/ band

Ten challenges. One-time payment.

  • Ten real-world challenges
  • Unlimited recordings & Vox scoring
  • Lifetime access
  • Path briefing for that band
Best value

The full Chicago path

$39$54

All six bands. Sixty challenges. Save $15.

  • Every challenge, A1 through C2
  • Sixty days, sixty conversations
  • Lifetime access
  • All future Chicago updates included

Secured by Stripe. One-time payment. No subscription.

Day one is waiting at
passport control.

The first challenge is free. Take a minute. See how it feels to speak.