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 ($19) - 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. 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. For Money Leap - Free: Your Money DNA type, financial blind spot analysis, 3 personalized financial action areas, resistance patterns, and a financial readiness score. Paid: The Money Playbook ($19) - full breakdown of all 3 moves with impact projections, comparison matrix, resistance counter-moves, and specific next steps. The Money Roadmap ($49) - everything in the Playbook plus a 90-day financial plan, weekend financial audit, move-specific templates and scripts, a 4-week guided program, and an AI money coach for 30 days. For Leap Up - Free: Your role map, gap analysis, alternative role suggestions, competitive landscape overview, and 5 AI coach messages. Paid: The Leap Up Plan ($49) - a comprehensive gap analysis with learning resources, 90-day action plan, conversation scripts for your boss, visibility and positioning strategy, compensation guidance, network map, and 30 days of AI advancement coach access.

Most briefs are ready in about 5 minutes and roadmaps in about 10 minutes - we'll email you as soon as yours is done. Because every section is generated specifically from your answers (not from templates), some occasionally need a closer look to make sure we got it right. If yours does, give us a couple hours. We don't send it until we're proud of it.

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. Each assessment is designed for a different situation: First Leap for students and early-career professionals who don't know what direction to go, Career Leap for experienced professionals ready for a career change, Leap Up for professionals who want to advance in their current career track, Freedom Leap for anyone ready to go independent, Money Leap for anyone ready to transform their relationship with money, and Life Leap for anyone facing a major life decision. They work powerfully together but you can take any one independently.

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 your friends 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 ($19) 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 that's been specifically configured around frameworks Jon developed through 9+ years of coaching and retreat facilitation. It 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 result is 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.

First Leap is a career direction assessment built for students, recent graduates, and anyone early in their career who feels lost. It maps your 6 core strengths, identifies your resistance pattern, and generates 3 personalized career directions with income projections, difficulty ratings, and AI-proof scores. It's not a personality label - it's a concrete starting point.

First Leap is for people who don't know what direction to go yet - students, recent grads, and early-career professionals. It focuses on discovering your strengths and exploring possible directions. Career Leap is for experienced professionals who know they want a change but need to figure out what's next. It maps your Work DNA, identifies transferable skills, and generates career paths based on your existing experience.

First Leap identifies your strengths across 6 dimensions and assigns you a Strengths Identity type that captures who you are when you're at your best. Types include The Catalyst, The Strategist, The Builder, The Guide, The Analyst, and The Creator. Each type reflects a unique combination of what energizes you, what you're naturally good at, and what others already rely on you for.

The First Leap Blueprint ($19) fully maps each of your 3 career directions with detailed breakdowns: what the work looks like day-to-day, what's included in each path, qualification mapping showing why your background makes you a fit, income ceilings showing long-term earning potential, AI-proof career scores, and your specific first steps for each direction. It also includes your full resistance pattern analysis and a personalized transition timeline.

Leap Up is a career advancement assessment for professionals who want to move up in their current career track - not change direction. It maps the gap between your current role and your target role, then generates a personalized plan to close it. The free assessment includes a role map, gap analysis, alternative role suggestions, and 5 AI coach messages. The Leap Up Plan ($49) adds a full 90-day action plan, conversation scripts, learning resources, visibility strategy, compensation guidance, and 30 days of AI advancement coach access.

Career Leap is for people who want to change direction - different industry, different role, different career entirely. Leap Up is for people who love their career but want to advance: get promoted, move into a leadership role, or level up where they are. Different assessment, different analysis, different deliverable. Career Leap generates career paths. Leap Up generates a gap-closing plan with conversation scripts, learning resources, and a 90-day action plan.

The Leap Up Plan ($49) includes: a detailed gap analysis across every competency standing between you and your target role, a 90-day action plan with specific weekly actions, conversation scripts for your boss and key stakeholders, a personalized learning plan with courses and resources, a visibility and positioning strategy, a compensation brief with negotiation guidance, a network map of who to connect with, and 30 days of AI advancement coach access. Every section is generated from your actual assessment answers - not templates.

First Leap is designed to be taken by the student themselves - the questions ask about personal experiences, feelings, and preferences that only the student can answer accurately. However, parents are welcome to take it alongside their child to better understand the results and have a more productive conversation about career direction. Many parents find the results help them understand what their child is actually drawn to vs. what they assumed.

No. Money Leap is a financial education and self-awareness tool. It helps you understand your financial patterns, blind spots, and goals - but it does not provide personalized investment advice, tax guidance, or legal financial recommendations. For specific decisions about investments, taxes, or financial planning, we recommend consulting a licensed CPA, CFP, or financial advisor.

The free assessment reveals your Money DNA type (your financial personality), your financial resistance patterns, a blind spot analysis, and 3 personalized financial action areas. The Brief ($19) adds detailed breakdowns, impact projections, and specific next steps. The Roadmap ($49) includes a 90-day plan, a weekend financial audit exercise, templates and scripts, a 4-week guided program, and an AI money coach for 30 days.

No. Money Leap never asks for account numbers, passwords, or exact balances. The assessment asks about income ranges, spending categories, debt types, and financial goals - enough to generate personalized insights without requiring sensitive financial data.