DAWN FLEMING
DAWN
FLEMING
Helping ambitious women live their Boldest Years
SEE DAWN IN ACTION
KEYNOTE #1
Redefining Retirement: How to Create a Midlife in Paradise in 90 Days or Less
Audience Best For:
Retirees or those who are preparing for retirement
KEYNOTE #2
ROL vs. ROI: Why Return on Life
is Your Best Investment
Audience Best For: Professionals &
career changers who want midlife reinvention.
WHAT PEOPLE SAY ABOUT DAWN
My biggest takeaway from Dawn's talk was you always have to be prepared really for the unexpected. You never know what's going to happen. We've had stock market crashes, real estate crashes and COVID. And if you do not have your exit plan in place and know what you're going to do, when things seemingly fall apart, your world may fall apart. So always be prepared. - Jonathan Ellis, Owner of Kleen Crete, Inc.
I heard Dawn's talk about claiming your dream life. I'm so excited! I had no idea. I thought my only options were in terms of what I could create, where I could live. I've learned about all these different things you can do. I didn't know you could buy real estate or meet people aligned with you outside of the United States that are looking for the same thing. So I'm so blessed that I got to experience her talk. My mind is definitely expanded and I can't wait to see what's next for me - Afiya Al-Fayiz, Co-founder & CEO at Underdog Millionaire Business Accelerator
If you haven't heard Dawn speak, I highly suggest you do. If you feel stuck and that you're not living your dream life, Dawn has a very interesting perspective from her business, legal and life experience. You can really tell that Dawn has so much wisdom and I personally am looking forward to hearing whatever else Dawn has to share, because I know that there's so much more that I can't even fathom. Joseph Tomczyk, Realtor
I just heard Dawn talk. Her story is really inspirational and really, really cool. What I took away was you ought to go for what you want, everything. You go all in no holds barred. Stability should be planned because as she shared her story, if you don't play your cards right, life can take you out. So I really think that she knows about real estate, business and life cycles because she really knows what she's talking about. Dawn has lived and breathed it. - Curtis Van Driesche
Dawn Fleming doesn't just speak about reinvention—she's lived it.
An attorney turned alchemist, bestselling author, entrepreneur, and speaker, Dawn has reinvented her own life multiple times. After overcoming financial devastation, she and her husband Tom sold nearly everything they owned, sailed through the Panama Canal, built a successful business in Mexico, and proved it's never too late to create a life you truly love.
Originally from Minnesota, Dawn began her career in real estate before earning her law degree from Western State University College of Law. As a California attorney specializing in international business transactions, she developed a unique ability to combine strategic thinking with practical problem-solving.
That blend of business acumen and legal expertise later helped her become an award-winning entrepreneur, top producer, and sought-after sales trainer.
For more than two decades, Dawn mentored thousands of entrepreneurs, helping them build successful businesses while creating lives of greater freedom and purpose.
Today, as the founder of Boldest Years, she empowers ambitious women to navigate life's transitions with clarity, courage, and confidence.
Whether she's speaking to entrepreneurs, professional women, business leaders, or organizations embracing change, Dawn inspires audiences to stop waiting for "someday" and start creating lives filled with freedom, purpose, possibility, and adventure.
Her presentations combine powerful storytelling, practical strategies, and genuine encouragement, leaving audiences equipped to take the next bold step toward the life they truly want.
