Jackelyn Keller, a marketing leader, strategist, and educator—and Founder of Jackwell Partners, a marketing consultancy—shares her journey from sales assistant to CMO and what it taught her about trusting your instincts. Known for translating complex technology into clear, actionable strategy, she explores career pivots, building confidence without certainty, and why mentorship and relationships often matter more than resumes. Takeaways Confidence isn’t about having all the answers–it’s trusting that you’ll figure it out. Career growth comes from trying new things rather than staying where you’re comfortable. Relationships often matter more than what’s on your resume. Mentorship works best when it’s rooted in empathy and active listening. Taking care of yourself shapes how you show up at work and in life. Chapters 00:00 Introduction to Jackelyn Keller and her background 02:30 Building a career across marketing, teaching, and entrepreneurship 06:10 Knowing when to push through versus when to pivot 07:45 Taking risks before feeling ready 10:00 Redefining confidence as self-trust 11:40 Overcoming fear of public speaking through teaching 14:15 Mentors who shaped her career 16:20 What makes a great mentor 17:20 Why leaders struggle to ask for help 18:20 Managing self-doubt and personal pressure 20:00 The importance of outside perspectives 22:20 Advice for early-career professionals 23:15 The value of mentorship and community