World Reimagined

33 Entrepreneurial and Career-Driven Women Reveal the Biggest Challenges They've had to Overcome

While it’s certainly appealing to envision a career path free of challenges, it’s often those very challenges that allow us to grow in ways we never thought possible. For the following 33 career-driven women, what mattered most was not the obstacles themselves, but rather the lessons they learned as they responded and moved on.

From running a company as a single parent to navigating feelings of anxiety and overwhelm, each of the hurdles below led to impactful discoveries and an opportunity to continue on their journey better than ever. It’s an important reminder for us all: leaning into life’s difficulties often reaps rewards that far outweigh the initial challenges.

Christina Blacken

Founder of The New Quo, a leadership development and inclusion consultancy.

Christina Blacken

“Seven months into my full-time entrepreneurship journey, I was ghosted by leads, ignored on emails, and under-appreciated and devalued by potential partners and collaborators. Thank goodness the seeds I sowed over the years from building reciprocal relationships across communities and sharing my work online started to bear fruit, and completely flourished in tandem with the terrible incidents of multiple social and health pandemics that forced people to make unconscious social issues conscious.” 

Lexie Smith

Founder of THEPRBAR inc., an online coaching brand that helps entrepreneurs expand their impact, influence, and revenue.

Lexie Smith

“The biggest challenges I have faced have been self-induced and mainly point to one culprit—my own thoughts and mindset. I’ve turned to my support system outside of work when needed, invested in coaching, and immersed myself in communities of fellow female-entrepreneurs so I am consistently reminded that I am not alone.” 

Annelise Hillmann

Co-Founder and CEO of FRONTMAN, a Gen Z self-care brand offering immediate cosmetic solutions for guys.

Annelise Hillmann

“My greatest challenge has been preserving my mental wellbeing while raising, launching, and creating. The pressures of getting a startup off the ground are only exacerbated by the lack of funding or support for female founders. I'm continuously adding to my support system of advisors, mentors, fellow founders, and teammates who can be there through both the highs and lows.”

Meredith Noble

Co-Founder of Learn Grant Writing, helping those ready for a career change become paid grant writers.

Meredith Noble

“As an online course creator, my biggest challenge was finding product market fit. Ironically, what helped me overcome this obstacle was learning from other online course creators. Once I finally focused on my favorite customer segment and only spoke to them, we found success.”

Deepali Vyas

Founder and CEO of Fearless+, a digital subscription platform that develops leadership and life skills. 

Deepali Vyas

“When you're just getting started, you do everything for the company. To try to succeed, you attempt to do your best, even if it means putting in 100 or more hours a week. I overcame the challenge by taking on trusted and experienced partners who brought unbelievable expertise and hired people who were way smarter and better than me at their piece of the business.”

Alex Cooley

Founder and CEO of AC Electric, a womxn’s leadership consultancy.

Alex Cooley

“I’ve learned to put on my big girl pants and own my authority. I experienced a fundamental shift when I decided to lead. The biggest thing for me was making the choice to grow into the career version of adulting—to show up, learn, and ask for help.”

Daria Leshchenko

CEO of SupportYourApp, a Support-as-a-Service company that provides secure customer support to startups and tech businesses. 

Daria Leshchenko

“My company hadn’t been growing much for the first five years. I still don’t know how I managed to find more and more creative ways to grow, but I know that the enthusiasm of my team fuelled me in the most desperate moments. You can teach hard skills to anyone, but only people with the same values and energy will support you in the hardest moments.”

Anouck Gotlib

CEO of Belgian Boys, a CPG food brand passionate about spreading sweetness in people’s lives.

Anouck Gotlib

“The pandemic disrupted our business as we knew it. This forced us to pivot—and fast. We experienced through-the-roof growth online and hired four people over Zoom who we still have not met in person!”

Dorothy Kolb

Founder and CEO of dk east associates, providing C-suite support to businesses.

Dorothy Kolb

“I started my entrepreneurial journey as a single mom of four who had no financial or other support. It took me a long time to realize that asking for help, outsourcing, and finding communities were not signs of weakness or that I couldn't do it all. They were indications that I understood how to function at my highest and best use, and how to allow others around me to rise to their highest and best use.”

Shabrina Koeswologito

Content Creator of Slow Travel Story, a travel platform that encourages exploration of the world more slowly and sustainably.

Shabrina Koeswologito

“Growing up in Indonesia, the cultural norm to travel solo as a woman was rare. Yet, I knew I could never be something that I’m not, so I kept going with my intuition. I worked several jobs at the same time, learned public speaking, applied to over 100 jobs outside of Indonesia, and taught myself personal finance. 2016 marked the highlight of my career when I got to move to New York to finish my master’s degree.”

Ashli Weiss

Attorney at Weiss Law LLP, a law firm helping companies grow and build their businesses.

Ashli Weiss

“The most obvious challenge was having feelings of isolation. I’m now a part of a digital community where I share experiences with and learn from like-minded women in leadership positions.”

Jessica Sikora

Founder and CEO of SUPERBANDS, a nonprofit dedicated to building a community of hope at the interaction of mental health and music. 

Jessica Sikora

“When I first had the idea for SUPERBANDS, I was told that it was not worth pursuing. Because I was starting with no money and no previous business experience, I relied heavily on online free resources and using social media to spread the word. Through that, I was able to build up a network of people who believed in our mission and vision, and who helped me build the foundation of what the organization is today.”

Jessie Young

Manager, Strategic Initiatives at Uber, a technology platform that moves people and things from point A to point B.

Jessie Young

“The biggest challenge has been drawing and enforcing boundaries for myself. I have applied the corporate strategy of choosing to be bad in order to be excellent.”

Andreea Bodnari

Product Manager at Google, a technology company that makes the world's information universally accessible.

Andreea Bodnari

“One of the first obstacles I had to overcome in my career as a technology businesswoman was speaking with authority without being perceived as aggressive. My come-to-Jesus moment was when I realized how to be kind without being nice.”

Gloria Chou

Founder of Gloria Chou PR LLC, helping early-stage founders go from unknown to being seen, heard, and valued. 

Gloria Chou

“The limiting mindset that I need to be fully ready before doing something. Success comes from those who take imperfect action, and the number one thing that’s helped me grow my business from zero to multi-six figures is turning failure into lessons.”

Aura Telman

Founder and CEO of 13thrive, a leadership and human resources consulting firm.

Aura Telman

“I initially had trouble trusting myself with big decisions without seeking validation from others. I overcame this setback by creating a mindful decision-making process that worked for me. First, I check in with my head, then my heart, and finally my gut. If all these align, I’m confident in my decision making.”

Ko Im

Founder of konakafe, a mindfulness-based creative and hosting service provider.

Ko Im

“Feeling like an imposter and simply getting started were issues for me. I formed an LLC once I realized that I had to hire others for a project, but I wish I had started sooner!” 

Kelly Ann Collins

Founder and CEO of Vult Lab, an integrated marketing communications agency that focuses on social good.

Kelly Ann Collins

“I’ve struggled with making tough decisions that are not always popular opinion. Whether it was the choice to start my company despite the naysayers, or making budget cuts at the height of COVID-19, it's all challenging. Making the hard decisions, and sticking to them, is what benefits everyone in the end.”

Yewande Faloyin

Founder and CEO of OTITỌ Leadership Coaching & Consulting, an organization that coaches high-achievers and entrepreneurial leaders. 

Yewande Faloyin

“Quitting my job and not knowing what I wanted to do was a challenge. The decision itself was strangely easy, but the path leading up to that was extremely difficult because I was in the middle of my second burnout in two years. What helped me overcome it was to stop, connect, decide, and trust.”

Dina Kaplan

Founder and CEO of The Path, a meditation community dedicated to bringing meditation into the mainstream.

Dina Kaplan

“I had to learn how to speak up and ask for what I want. Now I have finally gained the confidence to say what's on my mind, and to do so with calmness and without fear. It took practice but now I am a much better leader and my team can trust me because they know I am speaking the truth.”

Rachel Soper Sanders

Co-Founder and CEO of Rootine, a company optimizing health and daily performance with precision nutrition. 

Rachel Sanders

“I’ve learned to maintain my best health and energy levels while founding and running a business. I find that when I take care of my physical and mental health I am a better leader, team member, and colleague. I make sure to optimize my health in areas like sleep, exercise, and nutrition, even during the busiest of work days, which leaves me ready to take on the tasks and challenges of leading a startup.”

Janet Alexandersson

Negotiation Consultant at On Your Terms, helping women executives and founders to optimize deals and negotiate without playing power games.

Janet Alexandersson

“The biggest challenge I have faced has been to focus on one path at a time—I'm an idea person and I'm easily excited about new things. I now allow the “idea” part of me to mostly become something I do during play as a way to exercise my brain.”

Thamina Stoll

Founder of Femme Hive, an online platform to support young female professionals. 

Thamina Stoll

“Overwhelmed, anxious, and lost—that's how I felt after graduating from college and kicking off my career. I suffered from depression for almost three years until I sought professional help and realized that most young women my age were going through a similar experience when transitioning from school to work.”

Heather Smith

CEO and Founder of Juliet, a mission-driven fertility company for women who choose more.

Heather Smith

“In the midst of launching my company, I received an email that the schools were shutting down. I’m a single parent who covers all caregiving responsibilities: emotional, physical, and financial. To make it work, I prioritized the work I needed to complete, sidelined the things that didn’t make the cut, relied on my gut instinct to make quick decisions, and set strong boundaries around when my workday ended.”

Raquel Rojo

Founder and CEO of Innata Style, helping rising women act confidently in life and work by elevating their personal image.

Raquel Rojo

“It was challenging for me to accept that I was at the beginning again in my mid-30s—that I was a beginner in many ways after more than 10 years in corporate and two master degrees. I overcame it when I understood that acceptance of your current situation is not only the key to happiness and performance in the now, but also to productive change in the future.”

Lauren Richardson

Founder and CEO of Radiance & Romance, a line of custom art jewelry.

Lauren Richardson

“I’ve learned to stop getting in my own way. It took me a long time to realize that one of the biggest obstacles to growing my business was myself. I started to notice when I would spiral into a list of excuses and then would work through and reflect on why I made those excuses. Finally, I created small, manageable actions that would get me closer to my goals but that didn’t feel so scary.”

Mandy Bynum McLaughlin

CEO and Founder of Race Equ(al)ity Project, creating content and partnerships to increase social equity in the tech community. 

Mandy McLaughlin

“My own self-doubt. Whenever I’m feeling stuck, not moving fast enough, I sign up for a class or workshop, and treat it as any other investment I would make—the intention is to make a return.”

Patricia Recarte

CEO and Founder of KADO, an enterprise networking and smart client manager for relationship-driven industries. 

Patricia Recarte

“My career has spanned over heavily male-dominated jobs, from investment banking to tech startups and now my own SaaS business. Most VCs backing female founders still focus on femtech, health, beauty, or consumer. Evolving in such big-ego environments has meant one thing to me: it’s not enough to work hard to stand out—it requires working three times harder than any other man to get to the top.” 

Melinda Wang

Founder of MW Projects LLC, a cultural production and art advisory firm.

Melinda Wang

“I began my career during the heyday of “work-life balance” gurus who told us that we were doing it all wrong if we worked long hours or brought work stress home. It was a challenge to reconceptualize their advice and to embrace the fact that, for me, it’s not about so-called “balance” but about priorities. What has made my journey joyful has been the opportunity to work on complex corporate deals, the discoveries that could only come from first-hand entrepreneurship, and the beauty in creating challenging curatorial projects.”

Emily Kunka

Digital Business Transformation Project Lead at UCB Biopharma, a global biopharma focusing on neurology and immunology.

Emily Kunka

“The biggest challenge I've faced within my career is trying to digitally transform the healthcare industry. I've been most successful in overcoming obstacles by making “what digitally-enabled change looks like” tangible for key stakeholders. As people are naturally afraid of what they don't know, giving them first-hand access or exposure to the tools and solutions we are building for patients allows them to experience the very real impact they are having on patient lives.”

Lauren Ephrat

Founder and CEO of Doodle Couture, a modern collection of stylish and innovative dog accessories.

Lauren Ephrat

“I struggled with determining the level of inventory to purchase prior to launching Doodle Couture. Without knowing exactly what the short-term results of our marketing and customer outreach would yield, I leaned heavily into my competitive market research to make the best determination of what the initial levels should be. As a bootstrapped startup, doing our homework was critical to protecting cash flow and giving us the best opportunity for balance and success early on.”

Heather Falconer

Founder of hatchers.tv, a think tank with a global network of creators.

Heather Falconer

“One of the biggest challenges I faced was selling my first business, wondering if it was the right decision, and then seeing the business change under new ownership. Yoga and meditation helped a lot, and seeing it as an opportunity to move on to create something new.” 

Marla Isackson

Founder and CEO of Ossa, a podcast network connecting women-hosted podcasts and women-focused brands.

Marla Isackson

“I had to overcome my need for perfectionism. I need to rapidly test new ideas and approaches in-market. This ‘test, rinse, repeat’ process provides me with timely consumer feedback, helping me to identify and implement ideas that will have the most impact for my business.”

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.

The views and opinions expressed herein are the views and opinions of the author and do not necessarily reflect those of Nasdaq, Inc.

Gesche Haas

Gesche Haas is the Founder/CEO of Dreamers & Doers, a private collective that amplifies the entrepreneurial pursuits of extraordinary women through visibility opportunities, resource exchange, and collective support.

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