Is the classic interview question “Where do you see yourself in five years?” still bouncing around your head unanswered? You’re not alone. This week we’re zooming in on the art—and science—of designing a five‑year career roadmap you can actually stick to.
At Mentoring Club our community has grown to 4,200 active mentors, 9,500 mentees, and an average of 170 sessions each week. That’s a lot of road‑mapping power! In this edition you’ll find frameworks, fresh perspectives, and seasoned guides who can help you turn big‑picture ambition into an actionable plan.
Inside: a deep dive on building (and living) your 5‑year plan, eight new mentors with relevant expertise, plus hand‑picked reads & books to keep your strategy sharp.
📅 Design Your Next Five Years
Frameworks, mentors & resources to turn ambition into a living roadmap
Blueprint to Reality: 5 Steps to a Living 5‑Year Career Plan
Harvard Business Review recommends beginning with the destination: picture your role, skills, and impact five years out—then work backwards. MIT’s “future‑résumé” exercise and Indeed’s milestone templates echo that advice, turning a fuzzy dream into concrete yearly goals you can measure.
But strategy alone isn’t enough. Edgar & Peter Schein’s Humble Inquiry reminds us to ask better questions of peers, leaders, and mentors—curiosity unlocks blind spots. Atul Gawande’s Checklist Manifesto shows how simple checklists keep complex plans on track when life gets hectic.
Pair those frameworks with a mentor’s candid feedback. Whether you need ESG know‑how, fraud‑risk insight, or product‑strategy finesse, the mentors below can stress‑test your roadmap, spot skill gaps, and hold you accountable—so your five‑year vision becomes a series of daily, doable decisions.
✨ Meet Your Potential Mentors ✨
Curious? These are just eight of thousands of mentors ready to co‑pilot your next five years—explore them all!
💡 Bring Your Draft—Not Just Your Dreams
Before your next session, sketch a one‑page version of your five‑year résumé. Showing concrete bullet points helps your mentor ask sharper questions (à la humble inquiry) and co‑create a checklist of next steps. Try it, and watch the conversation leap from abstract to actionable.
📚 Food for Thought: Recommended Reads
🗺️ How to Develop a 5‑Year Career Plan
Harvard Business Review shows how to turn the classic “Where do you see yourself in five years?” question into a concrete action plan: identify an inspiring end‑state, translate it into yearly goals, and build the skills, network, and experiences that bridge the gap.
Read More →🚀 Mastering the First 5 Years: Your Path to Career Success
Early‑career essentials—set clear goals, seek mentors, volunteer for stretch projects, sharpen communication, and keep a growth mindset—because proactive habits compound fast.
Read More →📝 Creating Your Five‑Year Plan (MIT CAPD)
MIT reframes the plan as a ‘future résumé’: picture the roles, skills, and achievements you want, then reverse‑engineer today’s learning, networking, and project choices to make that résumé real.
Read More →📋 How to Create a 5‑Year Plan (Plus Template)
Indeed’s step‑by‑step worksheet helps clarify what success looks like, define gaps, and set measurable milestones—handy if you like a concrete template.
Read More →💪 Thriving in Your First 5 Years
29 accomplished women share tips to build visibility, embrace rejection, and ask boldly for opportunities—keys to turning formative years into a launchpad.
Read More →📖 Book Corner
Humble Inquiry – The Gentle Art of Asking Instead of Telling
by Edgar H. Schein & Peter A. Schein
Master the curiosity mindset your five‑year plan needs: ask open questions, build trust, and surface hidden opportunities before you commit to action.
Learn More →The Checklist Manifesto
by Atul Gawande
Complex careers need simple safeguards. Gawande’s checklist method helps keep your multi‑year goals error‑free and moving forward.
Learn More →MEDDICC – The Ultimate Guide to Staying One Step Ahead in the Complex Sale
by Andy Whyte
Turn fuzzy business goals into metric‑driven wins. This framework shows how to qualify opportunities and rally champions—useful far beyond sales.
Learn More →Smart Brevity – The Power of Saying More with Less
by Roy Schwartz, Mike Allen & Jim VandeHei
Craft crisp updates that respect attention spans—key when rallying mentors, sponsors, or teams around your evolving plan.
Learn More →Escaping the Build Trap – How Effective Product Management Creates Real Value
by Melissa Perri
A reminder to measure progress by outcomes, not output—crucial when your five‑year plan risks becoming a busy list of features.
Learn More →Big visions thrive on small, consistent actions. Map your path, check in often, and let mentor feedback keep the compass true.
Ready to sketch—or refine—your five‑year blueprint? Dive back into Mentoring Club and schedule your next conversation.