Frequently asked questions

The core assessment takes about 10 minutes. Some are quick selections, others ask you to write a sentence or two. The more honest you are, the more specific your results will be. The Career Leap assessment also takes about 10 minutes and focuses on your skills, work style, and career path.

No. Personality tests tell you what you are. This tells you what's in the way. It identifies your specific resistance pattern - the way you unconsciously avoid the change you say you want.

This isn't a replacement for either. Think of it as a diagnostic. Therapy explores why. Coaching guides how. This names what - the specific pattern that's keeping you stuck. Many people take their results to their therapist or coach and say 'this is what I need to work on.'

For the core assessment - Free: Your resistance pattern name, four personalized insights (the pattern you can't see, the thing you didn't say, your mirror moment, and your one move tonight), and your readiness score. Paid: The Leap Report ($29) - a 2,000+ word personalized analysis with your resistance pattern in detail, cost-of-waiting projection, 2-year vision, 72-hour action plan, and your one breakthrough question. The 7-Day Audio Program ($97) - everything in the report plus a daily guided audio series with journal prompts and exercises. The Leap + Live Session ($297) - everything plus a 1-on-1 breakthrough session. For Career Leap - Free: Your Work DNA type, skill-joy gap analysis, resistance patterns, 3 personalized career paths with income ranges, a staged transition plan, and your first move tonight. Paid: The Career Brief ($9) - full breakdown of all 3 paths with month-by-month income projections, job titles to search, qualification mapping, resistance pattern analysis, and a path comparison worksheet. Works with AI tools like ChatGPT and Claude for personalized follow-up. The Career Leap Roadmap ($49) - everything in the Brief plus an Ikigai map, weekend experiments for each path, a 90-day transition outline, resistance pattern counter-moves, and a 4-week guided email program. The Roadmap + Live Strategy Session ($297) - everything in the Roadmap plus a 1-on-1 session to pressure-test your path and build an accountability plan.

Yes. The assessment is anonymous - no sign-up required. If you choose to enter your email to save results, we only use it to send you your results. We never sell or share your data. See our Privacy Policy for details.

Jon - a business owner, retreat facilitator, and someone who spent over $120,000 and 5 years studying why smart, capable people stay stuck. He's facilitated 23 retreats worldwide and built this system from real patterns observed across hundreds of people. Read more on the About page.

Yes, as many times as you want. Your pattern may evolve as your life changes.

That's worth paying attention to. Resistance to seeing a pattern is often part of the pattern itself. But also - this is a tool, not a verdict. Take what resonates, leave what doesn't.

Career Leap is a comprehensive career assessment that maps your skills, values, work style, and real constraints - then generates specific career paths with a plan to get there. It's for anyone rethinking their career - whether you've been laid off, you're burning out, or you just know it's time for something different.

The core assessment reveals what's holding you back - your resistance pattern, your hidden fears, and what staying stuck is costing you. Career Leap reveals what's ahead - your best-fit career paths, how to monetize your skills, and a 4-week action plan to get there. They work powerfully together but you can take either one independently.

Yes, and we recommend it. If you've taken the core assessment first, your Career Leap results will be enhanced with your resistance pattern data for deeper personalization. If you start with Career Leap, we'll invite you to take the core assessment after to understand what might get in your way.

When you purchase the Career Leap Roadmap, you get access to a 4-week guided action program. Week 1: test each of your top paths with hands-on experiments. Week 2: build a transition blueprint with income projections, skill gaps, and your first informational conversation. Week 3: identify and interrupt your resistance pattern. Week 4: score your paths and commit to one. Each week builds on the last, and the content adapts based on what you actually did.

The 7-Day Audio Program ($97) is available for the core assessment. It includes everything in the Leap Report, plus a personalized daily audio series that walks you through a 7-day arc: from awareness to honesty to action. Each day includes a guided audio session, a journal prompt, and a practical exercise. A new day unlocks each morning.

No. Career quizzes match you to generic job titles based on a few questions. Career Leap uses 30+ personalized questions including follow-up questions tailored to your specific answers - including what you're good at, what you actually enjoy, what people come to you for, and your real-life constraints - to generate specific career paths you may not have considered. The difference is specificity: not 'you should be in marketing' but 'you should be a fractional CMO for B2B startups based on your ops background and growth skills.'

The Career Brief ($9) is your 3 career paths fully mapped. For each path, you get: a detailed description of what the work looks like day-to-day, a qualification breakdown showing exactly why your background makes you competitive, month-by-month income projections from month 1 through year 5, five real job titles you can search tonight, and a transition difficulty assessment. You also get a full resistance pattern analysis and a side-by-side path comparison worksheet. It's delivered instantly as a PDF and on a dedicated web page. Pro tip: paste your Career Brief into ChatGPT or Claude and ask follow-up questions about any path - resume drafts, interview prep, skill gap research. Your Brief gives the AI the context it needs to give you specific answers instead of generic advice.

Every result is generated by advanced AI (Claude by Anthropic) that's been trained on frameworks developed by Jon through 9+ years of coaching and retreat facilitation. The AI doesn't guess - it cross-references your specific answers against proven career transition patterns to generate paths that are unique to you. No two results are alike because no two people answer the same way. Jon personally reviews assessments and the system is continuously refined based on real results. The AI delivers the depth of a personal career advisor at a price point that makes it accessible to everyone.

When our system detects ambiguity in your answers - like saying you want 'remote work' but also describing hands-on physical work as your dream - it asks 1-2 clarifying questions before generating your results. This makes your career paths significantly more accurate. Most assessments never ask for clarification, which is why their results feel generic. Yours won't.