Lysa Middleton’s Stories, Lessons & Insights

We’re looking forward to introducing you to Lysa Middleton. Check out our conversation below.

Good morning Lysa, we’re so happy to have you here with us and we’d love to explore your story and how you think about life and legacy and so much more. So let’s start with a question we often ask: What do you think is misunderstood about your business? 
I think that people misunderstand that entrepreneurship is no longer a luxury, it’s a necessity. Society has demonized multi level marketing and calls anything that requires investment a “pyramid scheme”. So many people do not realize that you must invest in your own future or spend the rest of your life building someone else’s.

Can you briefly introduce yourself and share what makes you or your brand unique?
Heyyy! I’m Lysa tha Boss Lady—entrepreneur, travel advisor, business coach, and lover of all things pink, purple, glittery, and purpose-driven.
I’m obsessed with entrepreneurship and helping others build something real. Over the past 8+ years, I’ve trained more than 7,000 agents and built a thriving travel business that lets me live out my passion while helping others do the same. I believe everybody can win when they’re equipped with the right mindset, tools, and support—and I’m here to make sure of it.

Whether I’m planning group cruises, coaching entrepreneurs, or turning up at sea while making money in my sleep, I stay focused on legacy, impact, and elevation. I don’t just travel—I create freedom through travel. I don’t just mentor—I transform hustlers into CEOs.

If you’re ready to boss up, book the trip, or finally bet on yourself—I’m your girl.

Great, so let’s dive into your journey a bit more. What part of you has served its purpose and must now be released?
I’m no longer a people pleaser. Tha Boss Lady has room for purpose only and reinvention includes putting myself 1st

Was there ever a time you almost gave up?
I’ve almost given up lots of times. You’re not going hard enough if you haven’t. Entrepreneurship is a roller coaster. Anyone going hard enough after their dreams will want to quit. The important thing as that you don’t quit, you keep going.

I think our readers would appreciate hearing more about your values and what you think matters in life and career, etc. So our next question is along those lines. What important truth do very few people agree with you on?
Accountability
Society has made accountability optional. It’s very important to be accountable for your future. If you allow others to dictate our shape your plans, you’re allowing them to write your paycheck. Own your actions. If you don’t like them, change them. Nobody has control over your future but you.

Before we go, we’d love to hear your thoughts on some longer-run, legacy type questions. When do you feel most at peace?
I feel the most at peace at sea. I love cruising! 2 a.m. on the balcony with just God, the ocean, and the moon is priceless. Peace just settles into your soul and I chase that feeling constantly.

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