How to Dress Like a $10M Business Owner (Before You Get There)
What if the way you dress is silently costing you sales, clients, and credibility?
In this episode of the Happy Productive Podcast, Jennifer sits down with personal brand strategist and Prosperous Image founder Lee Hayward to talk about why your image is one of the most underused tools in your business—and how aligning your presence with your power can fuel serious growth.
This isn’t about fashion. It’s about identity, alignment, and energy. You’ll learn how to show up like the 7-figure version of yourself—before you get there—and why your image might be the very thing blocking your next breakthrough.
In this episode:
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Why your image is repelling (or attracting) high-value clients
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How to align your wardrobe with your future business, not your past self
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What it really means to “dress for success” (hint: it’s not just about looks)
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How to lead with confidence—even when your body, mindset, or business is in transition
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Simple ways to uplevel your presence without sacrificing comfort or authenticity
Timestamps:
00:00 – Do You Look Like You’ve Already Closed $150K Deals?
00:22 – Why It’s Not About Clothes—It’s About Self-Identity
00:36 – Intro: Why This Conversation Matters
01:13 – Meet Lee Hayward: Brand Consultant & Author
01:49 – Lee’s Story: From Fourth Grade to Founder
03:43 – From Styling to Full-Scale Brand Strategy
04:40 – Jennifer’s Confession: “I’ve Always Struggled with Image”
05:49 – Where to Start When You Have No Style Roadmap
06:50 – The Real Question: How Do You Want to Feel?
08:15 – Why Comfort & Confidence Are the Baseline
09:07 – Aligning Your Wardrobe with a $10M Business Vision
11:06 – How a Prosperous Image Attracts More Sales
12:23 – Why First Impressions Are Built on Image
13:57 – Creating Trust Through Consistent Brand Experience
14:25 – Who Are You Really Dressing For? (Hint: Two People)
15:48 – Your Image Should Say: “You’re in the Right Room”
16:29 – Essentials for Upleveling Your Brand Image
18:21 – The Curse of $1M: Why People Wait to Show Up Fully
19:42 – Lee’s Wake-Up Call: “Would You Dress Like This If You Were Already Successful?”
20:55 – Showing Up to Events with Confidence & Alignment
22:13 – The “Impression of Increase” (And How to Use It)
24:21 – Quick Tips for Looking Aligned—Even in Yoga Pants
24:53 – How to Find the Right Branding Expert or Stylist
26:23 – How Lee Helps You Hold the Vision for Your Future Self
28:04 – Why It’s Never Just About the Clothes
28:23 – Image Isn’t Just Personal—It’s Company-Wide
30:28 – What If You’re Not Comfortable in Your Body Right Now?
32:40 – Strategic Dressing at Every Stage of Life
34:22 – Where to Find Lee + Get Her Book Strategically Suited
36:01 – Final Takeaway: Don’t Just Listen—Take One Aligned Action
Whether you’re scaling toward 7 or 8 figures, hosting live events, or just trying to show up like the boss you are—this conversation will rewire how you think about confidence, visibility, and brand presence.
Grab Lee’s bestselling book: Strategically Suited → [ Amazon link ]
Connect with Lee:
Jennifer Dawn is a business coach helping high-performing entrepreneurs scale smart, ditch burnout, and build a business that fuels their freedom and adventure.
Connect with Jennifer: www.jenniferdawncoaching.com
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