Wherever you’re currently at in your journey, looking back on where you’ve come from and all that you’ve achieved can be enlightening. You likely have some advice you’d give to your younger self and lessons you’ve learned the hard way. But how often have you considered what your younger self might say to you today after seeing all you’ve accomplished? 

To gain some insight into this question, we tapped into the Dreamers & Doers collective to hear from 31 trailblazing women how they think their younger selves would react to seeing where their paths have led them. Their responses are a reminder that while looking to the future is important, reflecting on the past and acknowledging all you’ve overcome is crucial to finding true joy in the journey.

Monique Guevara

Co-founder and CEO of SoulWell, a boutique digital booking and discovery marketplace.

“You are the woman I always dreamed of becoming—you followed your own path and trusted the process of doing the things that light you up. There are so many paths you could have taken, but it is clear that your impact has been far greater because you chose to walk with purpose and passion as your guides.”

Aura Telman

Founder and CEO of 13thrive, a boutique mindfulness consulting firm helping leaders design workplaces that value and celebrate everyone.

“I am so proud that you continued to be brave and take risks throughout your life and career. I’m amazed that you—a little girl from a small village in Romania—are now living a life you could have never dreamt of in your wildest dreams, building a business helping humans find peace, while staying true to your roots and honoring all the experiences that helped build you along the way.”

Antoinette Alexander Adefela

Founder and CEO of Exp.Design LLC, a creative agency that designs and develops custom learning solutions.

“For all of the times you wrote down your goals, created make-believe businesses, and read success stories in Black Enterprise, Essence, and Ebony—you have exceeded what you could have planned for yourself. You took risks and took action when you were afraid. I wouldn’t have imagined you developing elearning, but it totally makes sense and matches your curiosity, creativity, and love for learning.”

Dorothy Kolb

Founder and CEO of dk east associates, providing fractional CFO services and accounting strategy to small to midsize enterprises.

“I knew it. I knew you could and would do this. You just needed life to show you that you were strong enough, smart enough, resourceful enough over and over and over again until you listened. I, your younger self, knew no limits until you started putting them in place. I’m proud of you and what you’ve accomplished.”

Ko Im

Founder of konakafe, a creative hosting and holistic wellness service.

“You have done so many things. You have come out of your shell. You inspire me. Thank you for taking care of me, your inner child, in your adult healing journey. I feel loved and supported.”

Lis Best

Founder and CEO of Coaching for Impact, the secret weapon for women who are changing the world.

"Wait, what do you mean you didn't get married in your 20s and have three kids by 32?" 

Muirgheal Montecalvo

Founder and CEO of Vacayou Wellness Travel, a wellness travel platform and marketplace.

“You accepted the challenge, worked hard, and you never gave up on your goals of being successful. Dreams do come true when you put your mind to it.”

Thamina Stoll

Founder at Femme Hive, helping young, female professionals feel less overwhelmed in their 20s.

“I am so proud of you for having gone after your big dreams in the most unapologetic and authentic way. It’s comforting to know that all the work I’m putting in now and staying true to myself will pay off eventually.”

Far Momin

Founder at She Plants Love, an artisan skincare rooted in self-love and inclusive beauty.

“I’m proud that you’re comfortable in your own skin. It shows me that I have what it takes to create my corner of joy so long as I continue to believe in myself.”

Alice Braccini

CEO and Founder of Violetta Group, a PR and communications agency dedicated to bringing awareness around creative individuals and companies.

“Wow—you are much more fearless than I thought! I knew you would not become an actress but I didn’t think you’d become an entrepreneur, as I didn't even know what that really means back in 1990s Italy.”

Sonia Byun

Co-founder of Pomcare, an online clinic for common vaginal conditions.

“I’m impressed by how confident you have turned out and that you’ve come to recognize that confidence is not something that you’re born with but rather earned throughout your career.”

Kristine Locker

Founder of LOCKER, a Chrome extension and social shopping platform.

“Look at us go! I would not have expected us to be creating a lifestyle technology company but I am not surprised we are an entrepreneur. I am so proud of how we reinvented ourselves after so many years of feeling so lost.” 

Lori Sussle Bonanni

Founder and Communications Consultant at elssus, LLC, a multi-disciplined communications consulting firm.

“You always did love the quote, ‘Leap and the net will appear.’ It's thrilling you kept that mindset front and center for your 20+ year career. You always had intrapreneurial roles at multinationals where you had to be scrappy and creative. It's no surprise you're thriving as an entrepreneur.”

Arielle Shnaidman

Executive Coach at Arielle Shnaidman LLC, executive coaching for founders and leaders. 

“You have your own business?! You work for yourself?! You're a coach? But you hate sports!" 

Yewande Faloyin

Founder and CEO of OTITỌ Executive Leadership Coaching, a coaching business serving serial high-achievers.

“No way! I can't believe we found something that we are truly passionate about, that we are great at, and that gives us the freedom and flexibility to live anywhere in the world. I am in awe and feel less worried, ready to explore the journey through IT, banking, consulting, business ownership, and beyond!”

Rachel Soper Sanders

Co-founder and CEO of Rootine, a wellness company unlocking better health and daily performance with precision nutrition. 

“I’m so proud of you for taking a seat at the table and voicing your opinions early on. As a founder, CEO, leader, and mom, you are paving the way for the next generation of female leaders to believe they are capable of anything.”

Morgaine Trine

Owner of Honestly Bookkeeping, a bookkeeping and controller services firm helping small business clients.

“You're the type of person I always hoped I'd be. Also, accounting? Really? What happened to all that ancient history stuff?”

Willow Hill

Chief Creative Officer and Co-founder of Scout Lab, a purpose-driven creative agency based in NYC.

“I am so happy that you are proving that making an impact and making money can coexist. Clearly, the old adage of ‘starving artists’ was never real. You’ve shown me that creativity can create abundance.” 

Degelis Tufts Pilla

Co-founder and CEO of TribeTokes, a company creating luxury CBD vape oils, skincare and wellness products. 

“Wow, I didn't see that one coming!"

Lauren Richardson

Founder and CEO of Radiance & Romance, a line of custom art jewelry for those who defy conventionality.

“The only thing you ever wanted to be was an artist. Why did it take you so long to realize it?” 

Jamie Lieberman

Owner of Hashtag Legal, providing legal services to entrepreneurs and creators.

“I am glad you chose to showcase your personality in your business, rather than hiding it. I know you were often told you were ‘too much’ but it looks like you were truly just right.”

Belma McCaffrey

Founder and CEO at Work Bigger, offering coaching and community to high achievers. 

“I’m incredibly proud seeing the career you’ve built for yourself. I’m proud to see that you’ve built a business that’s profitable, makes an impact, and allows you to enjoy life—and that you’ve done so in a healthy way that supports your well-being.”

Jessica Sikora

Founder and CEO of SUPERBANDS, a nonprofit dedicated to promoting positive mental health for teen music fans through wish-granting opportunities. 

“I’m proud that you took the hardest times of your life and the mental health struggles you went through to build the community you once longed for.” 

Ashli Weiss

Attorney at Weiss Law LLP, a law firm helping companies navigate and propel their businesses.

“I had no idea that your bold personality, which often got you into trouble as a teenager, and perceptive instinct, gained from a very humble childhood, could be channeled into building a successful career as an attorney.” 

Shani Syphrett

Founder at Jamila Studio, a business consulting firm for mission-driven creative companies and women of color founders.

“I’m surprised by the portfolio career you’ve built—especially how you’ve balanced corporate work with entrepreneurship. I’m happy that you became successful coloring outside the lines.”

Marla Isackson

Founder and CEO of Ossa, a two-sided marketplace that connects brands with podcast advertising. 

“I’m comforted knowing that you finally recognized that when you follow your instincts and trust your capabilities and experience, you can achieve career satisfaction and success.”

Nina Kong-Surtees

Founder of smART Advisory, serving as a mentor, guide, and resource for mid-career visual artists.

“I’m in disbelief and baffled about how someone with an art history degree could create a business. You’ve paved an uncharted path to building a business to support artists to thrive and continuing your life-long commitment to turn art history into compelling stories and legacies that deconstruct the cultural myth and mindset of ‘starving’ artists.”

Ivelyse Andino

Founder and CEO of Radical Health, working to engage, equip, and empower all people to understand and advocate for themselves.

“Now I understand the bigger picture. All those tough moments I lived through were the driving force to propel and inspire what I’m doing today. I have a better appreciation for those challenging times that started this journey, which ultimately led to creating Radical Health.”

Katherine Sprung

Host and Executive Producer at Sprung On Food, a web series highlighting small businesses in the food and beverage industry.

“You’ve done some pretty cool things! I really thought of my future path as being pretty linear, but it definitely took some really interesting twists and turns. You’ve accomplished things that I would have never thought I'd do!” 

Carolyn Bothwell

Founder & CEO of Freelance Founders, a digital, members-only community and resource hub for the top creative freelance talent from all over the world.

"What is freelancing? I never even knew there was a career path in which I could work for myself and with my ideal clients, and maintain a sense of autonomy and freedom!”

Srujana Bobba

CTO at Librari, a destination for short, mobile learning videos. 

"Wow—what a rollercoaster career you have had! I’m glad that you didn't give up on your dreams and worked hard to achieve them.”

All individuals featured in this article are members of Dreamers & Doers, an award-winning community and diverse ecosystem amplifying extraordinary entrepreneurial women through PR opportunities, authentic connection, and high-impact resources. Learn more about Dreamers & Doers and subscribe to its monthly The Digest for top entrepreneurial and career resources.