Make the Leap: Career Leap
You already know
you're built for more than this.
The Sunday dread that starts Saturday afternoon.
Watching people with half your skill build twice your life.
Knowing something needs to change - but not knowing what you'd change to.
Take the AssessmentFree. 10 minutes. Results are instant.
For professionals who want a path forward.
Taken by 5,000+ professionals so far.
The most advanced career clarity system available. Built on proven frameworks and behavioral science to connect what you're good at, what you actually want, and what's been stopping you - then map exactly where to go.
Who it's for.
Putting out fires. You’re spending your days putting out fires and sitting in meetings about meetings, doing work that doesn’t use what you’re actually good at.
Salary flat. Skills growing. You’re working hard, watching your salary stay flat, and feeling like you’ve outgrown the role but don’t know what’s next.
Between jobs. You’re between jobs or coming back from a break, tired of guessing what every recruiter wants without a clear sense of where you should even be looking.
Bored in a job you used to love. You’re bored at a job you used to love, doing it on autopilot, wondering when it stopped feeling meaningful.
Senior. Stalled. You’re plateaued at a senior level with no clear next step, watching peers move on while you wait for a roadmap that actually fits you.
You've done the thinking. That's not what's missing.
You’ve scrolled the job boards, taken the quizzes, and told yourself ‘maybe next quarter’ so many times it stopped meaning anything.
You have the skills. The experience. The quiet certainty that you’re built for more.
What you don’t have is a clear direction. And every month you wait, the gap between where you are and where you could be gets wider.
The reason you're stuck isn't a character flaw.
You’ve been trying to solve a direction problem with willpower. Telling yourself you’ll figure it out eventually. Reading one more article. Taking one more quiz.
The issue was never motivation or effort. It was that nobody looked at YOUR specific skills, experience, and constraints and said: here are the three directions that actually make sense for you.
That’s what Career Leap does. A 10-minute assessment about who you actually are. 3 career paths built from your answers - with real income projections, not inspirational guesswork.
The first one takes 10 minutes. It’s free. And it’s more specific than anything you’ll get from a $300/hour career coach.
Most people who take it say the same thing: ‘I didn’t know that path existed, and now I can’t stop thinking about it.’
What you walk away with.
Not another personality label. A map with actual roads on it.
Your 3 career paths
3 specific directions built from your answers, with income projections and difficulty ratings. Not generic job titles pulled from a database.
A way to test before you commit
2-4 hour exercises to try each path this weekend. Without quitting your job, spending money, or telling anyone.
A plan that actually moves
Weekly guidance that turns ‘I should do something’ into ‘here is exactly what I am doing this week.’ Built around your specific resistance pattern.
A look inside
Personalized career paths with income range, difficulty, and 5-year outlook
Month-by-month income projections
Step-by-step exercises with time estimates
Printable experiment worksheets for each path
Structured 4-week program with progress tracking
Included with your Roadmap
Your personal AI career coach
It already knows your Career DNA, your 3 paths, and your resistance pattern. Ask it anything for 30 days - interview prep, resume angles, next steps, motivation. No re-explaining your situation.
This isn't a personality test.
MBTI told you you're an INTJ. StrengthsFinder told you you're strategic. Great. You still don't know what to do Monday morning.
Career Leap is built on Ikigai mapping, resistance pattern science, and a proprietary analysis system that cross-references your skills, values, constraints, and blind spots to generate career paths with real income potential and 5-year durability. Not types. Not labels. Paths you can test this week.
It reads between the lines of your answers and finds connections you can't see yourself - the gap between what you're good at and what you enjoy, the pattern that's kept you circling, and the direction that fits your actual life, not just your resume.
10 minutes. Four phases.
Four phases that map your career from every angle.
Phase 1
Where You Are
Your current situation, frustrations, and what’s been pulling at you.
Phase 2
What You Bring
Your skills, strengths, and the things people come to you for.
Phase 3
What You Want
Your values, dream scenario, and what’s actually stopping you.
Phase 4
Reality Check
Your constraints, risk tolerance, and willingness to move.
What this feels like.
Early responses
“I’ve taken every career quiz on the internet. This is the first one that told me something I didn’t already know.”
Sara L., Product Manager“The ‘Work DNA’ section was wild. It connected dots between my hobbies and my career that I’d never seen.”
Keith R., Software Engineer“I spent six months paralyzed about what to do next. This gave me three clear options in 20 minutes.”
Connor M., Account ExecutiveThree levels of depth.
Start free. Go deeper if it resonates.
Free
Free Assessment
Start here
- ✓28 questions, ~10 minutes
- ✓3 personalized career paths
- ✓Income ranges and difficulty per path
- ✓Resistance pattern analysis
- ✓Instant results
$29
Career Brief
Go deeper on the 3 paths
- ✓Everything in Free
- ✓Detailed breakdown of all 3 paths
- ✓Month-by-month income projections
- ✓Outreach email templates per path
- ✓AI prompt library for cover letters, interviews, resumes
- ✓Job titles to search per path
$79
Career Roadmap
Build the actual plan
- ✓Everything in Brief
- ✓Ikigai map
- ✓90-day transition outline
- ✓Weekend experiments per path
- ✓Resistance pattern counter-moves
- ✓4-week guided email program
- ✓AI Career Coach for 30 days
Questions.
Is the assessment really free?
Yes. You take all 28 questions and get your full results, including three personalized career paths, free. The Brief ($29) and Roadmap ($79) are optional upgrades for going deeper. The free version stands on its own.
How is this different from MBTI, StrengthsFinder, or a personality quiz?
Those tell you what type you are. Career Leap tells you what to do Monday morning. Personality tests stop at “you’re an INTJ” or “you’re a strategic thinker.” Career Leap takes your skills, values, constraints, and what’s been stopping you, then produces three career paths with real income projections. It maps directions, not labels.
Is this AI-generated? How accurate can it actually be?
The analysis is generated by Claude, the most capable AI model available, applied to frameworks Jon developed over years of career consulting, retreat facilitation, and one-on-one work, with patterns drawn from over 5,000 completed assessments. It is not a generic AI dump. Every paragraph is built from your specific answers. The most common reaction in our feedback is some version of “this is more specific than coaches I’ve paid actual money for.”
What if my three paths don’t feel right?
You can refine them once. After you see your initial paths, there’s a “something missing?” box where you describe what feels off, and the system regenerates new paths based on your feedback. Specific context (a constraint we missed, a path you don’t want, a value we got wrong) gets incorporated into the new set.
What if I’ve been out of work for years?
That’s part of what the assessment accounts for. Career breaks, gaps, and re-entries are common in the data we’ve seen. Your paths will be built around where you are now, not where you were three years ago. The system also surfaces what’s stopping you, which for many people in this situation is some combination of “the field has moved on,” “my old network is gone,” and “I don’t know how to explain the gap.” None of those are fatal.
Are the income projections realistic, or aspirational?
Both. Each path includes a starting range (where you’d land in the first 6-12 months) and a 5-year ceiling (what’s achievable at that level with focused effort). Numbers are anchored to current market rates for the role at your experience level, adjusted for location if you provide one. We’re honest when a path requires more time or skill-building before it pays. If your current income is $60K and a path reasonably caps at $90K, we say that, not a fantasy number.
More personalized than a $300/hour career coach. Not an exaggeration.
A good career coach spends the first three sessions just understanding your situation - your skills, your values, what's actually stopping you, what you've already tried. That's $600-900 before they even start giving you direction.
Career Leap does that in 10 minutes. Then it cross-references your answers against patterns from hundreds of real career changers to generate paths that are specific to you - not recycled advice from a framework designed for someone else's life.
Your Work DNA type. Your resistance pattern with the specific triggers and counter-moves. Three career paths with real income projections, Week-1 experiments you can run without quitting your job, and a Launch Kit with ready-to-use templates and a first-week action plan built around your actual constraints.
Every word in your results comes from your answers. No two reports are alike. The Career Brief is $29. The full Roadmap is $79. A single coaching session that delivers less costs six times that.
This is what $120K of personal development research and the most advanced AI available in 2026 look like when they work together. Real methodology. Real personalization. A price that doesn't require a leap of faith before the actual leap.
Built by Jon
Career changer. 73 countries. 9 years building businesses. Went from finance to travel to retreat facilitation to building tools for change. Knows what it feels like to stare at a ceiling at 2am wondering if this is really it.
Read the full story →Free download
50 careers people actually switched to
The Career Change Cheat Sheet. Organized by your current industry - teaching, healthcare, finance, retail, government, admin, sales. Find your field, see what's possible.
You've spent long enough thinking about this.
10 minutes. Three career paths you can test this week.
Free to start. Go deeper if it resonates.
Looking for something deeper? Take the Life Leap →