Waypoint
Career design, coached — not shortcut.
Waypoint is a career design app from Citadel Projects, built with a real executive coach. It does not hand you a list of jobs. It helps you decide what to aim for, test it in the real world, and keep growing — one clear step at a time.
In Brief
The case for coaching, not shortcuts.
Most career advice is built for speed: write a sharper CV, send more applications, take the first offer. That advice treats a career like a transaction. A career is not a transaction. It is the longest project most of us will ever work on — and it deserves a coach, a plan, and practice, not a shortcut.
Waypoint gives you that coach in your pocket: structured reflection, real-world tests, and a plan that travels with you from one role to the next.
Contents
01 How Waypoint Coaches · 02 The Four Stages · 03 The Arc · 04 What You Walk Away With · 05 Built for Longer Than One Search · 06 Your Data Is Yours · 07 How It’s Built · 08 Who It’s For · 09 Availability
01 How Waypoint Coaches
Why I Built It
The starting point was not software. It was the realisation that most advice about careers is built for speed — write a sharper CV, send more applications, take the first offer. That advice treats a career like a transaction. A career is not a transaction. It is the longest project most of us will ever work on.
I wanted something slower and more honest: a way to work out what matters to you, test it before you commit, and build the skills and evidence to move with confidence. Waypoint is that process, made usable every day.
Working with Miles
For the last three years, I have worked with an executive coach named Miles. Each week we go over what actually happened — not what I planned, not what I hoped — and work out the next honest step. For six months we built that coaching into software: the questions Miles asks, the order he asks them in, and the way he holds you to a standard without rushing you.
Waypoint is not a chatbot pretending to be a coach. It is a structured coaching process, designed with a coach, that you work through at your own pace.
“The delivery adapts. The standard doesn’t.”
02 The Four Stages
Every Waypoint journey moves through four stages. You can move at your own pace, and you can return to an earlier stage whenever your situation changes.
Understand your strengths, values, and what good work looks like for you.
Research roles, industries, and people — and narrow to a short, honest list.
Try a small, real project, conversation, or piece of work before you commit.
Use what you learn to grow in your current role, or to make a considered move.
The amber dashed line is the thread through all four stages: the same standard, applied at each step.
03 The Arc
- Reflect— take stock of where you are and what matters.
- Define— name the direction, in your own words.
- Explore— gather evidence about what fits.
- Decide— commit to a direction, for now.
- Act— take the next honest step.
- Review— look back at what happened.
- Grow— carry the result into the next loop.
The Arc repeats. Careers do not end at one decision, so Waypoint does not end at one plan — you run the Arc again, with better evidence each time.
04 What You Walk Away With
The lasting value isn't a document or a checklist. Those show up on their own, as a byproduct of the work you put in. Three things stay with you.
Grounded in real work, with the demonstrated ability to move toward it.
Between the task system and the arc, you learn to turn an ambition into a sequence of steps and then see it through. That transfers well past careers.
It compounds quietly across the rest of your working life.
05 Built for Longer Than One Search
Most career apps are built for a single job hunt. Waypoint is built to still be useful several roles from now. Context accumulates across sessions and stages, so when you come back after landing something, your history is intact and the coaching resumes instead of restarting.
It also learns how you learn: the formats you prefer, the pace that works, the kind of feedback you actually respond to. The relationship is meant to deepen.
Career development isn't a sprint. People spend months inside Learn and Build. Alignment work surfaces and resurfaces as conditions shift. Interview prep sharpens with every real interview that follows it. A career coaching tool is worth about as much as the length of time it stays useful.
06 Your Data Is Yours
Your career data belongs to you. The conversations with Miles, the context you build, and the work you produce are personal information, and Waypoint treats them that way. Nothing sold, nothing mined, and you can export your full history whenever you want.
The commitment matters more the longer you stay. Every session, Miles understands a little more about your direction, your history, and how you work best. That accumulated understanding is what makes him your coach rather than a coach. Information that personal shouldn't belong to anyone else. Privacy is built in from the start, because a coaching relationship can't stand on anything less.
07 How It’s Built
Waypoint is a native application, built to run fast on devices you already own. The coaching layer is powered by Anthropic's Claude and assembled through a six-layer prompt system that carries your identity, your stage, your prior sessions, and your conversation into every exchange.
A few decisions for the technically minded. Context bridging carries key information across stage boundaries automatically, so the Build coach knows what you studied in Learn and the Prepare coach knows what you built and where you're aiming it. Session summaries are generated when a session closes and injected at the start of the next one, giving Miles continuity without re-reading everything every time. Prompt caching runs throughout to keep latency and cost down. Production users reach the model through a managed proxy that handles the API key server-side. No key entry, no configuration.
08 Who It’s For
Waypoint serves people across three broad career stages, with a different entry point and a different payoff for each.
Early career: students, recent graduates, and career changers who need structured learning paths, a method for building real experience, and interview skills from the ground up.
Mid career: two to ten years in, looking to level up or pivot, needing skill-gap analysis, targeted alignment work, and sharper interview preparation.
Late career: senior people who haven't interviewed in years and need help positioning their seniority, refreshing their approach, and translating deep expertise into a story that lands with an audience that doesn't already know them.
All three share a disposition. They aren't waiting for a career to be handed over. They want to build one that's theirs, with someone alongside them while they do it.
09 Availability
Available on the Apple App Store for iPhone, iPad, and Mac. Price: $5.99/month or $49.99/year, with a 7-day free trial.
Android beta cohort — ask to join.
Request Android beta access
Waypoint for Android is in closed beta. Request access and I'll add your Google Play email to the tester list.