Entrepreneurial Women: How Asking for Help Transformed Their Journey
The entrepreneurial journey can be challenging to navigate. However, there is one method that can ensure a business has a higher chance of success: asking for help.
While some may view asking for help as a sign of weakness, it takes a strong person to admit they don’t have all the answers and seek out those who may be able to support them. As the following 23 entrepreneurial women have proven, asking the right questions in the right ways can make all the difference.
It’s essential to put our pride and self-sufficiency to the side at times and remember that the hardest part of seeking support is often asking that first question. Yet doing so can quickly lead to game-changing impact.
Nics Asawasudsakorn
Founder of Lovanie, a sustainable fashion brand for petite women 5'4" and under.
How Asking for Help Supercharged My Journey: I signed up for a six-month accelerator and mentorship program for sustainable fashion brands with Factory45, and that's when I began to work on my dream seriously. With the structured courses and one-on-one mentorship, I was finally able to launch my own sustainable brand, Lovanie, a year later.
My Advice: The first step is to identify where you need help for your business. The second step is taking the leap of faith to invest in yourself. The best type of mentors to look for are the ones who have been in your shoes before.
Meghan Carreau
Co-Founder and CPO of Aztech Digital, a creative commerce consultancy that works with founders to design, build, and grow their companies online.
How Asking for Help Supercharged My Journey: By asking for help, I formed closer relationships with so many people, many of whom are now my life-long mentors. People are problem solvers. If you have a vision and can explain what you're struggling to figure out, most people will do their damndest to help you. In the end, they feel closer to you when they feel valued because they helped you.
My Advice: Don't be afraid to tell a handful of people about what you're struggling with. If the first person doesn’t help untangle the knot, move on and explain it to the next. By explaining parts of a problem, you start to lay it out more plainly, even for yourself. The gaps become crystal clear, and then you can chart a course to a solution one step at a time.
Chithra Durgam
Founder of Blue Check Skill, a company that works with celebrities and large brands who want to amplify and monetize their owned content through Amazon Alexa voice skills.
How Asking for Help Supercharged My Journey: I created my own voice skill, the Dr. Durgam Experience, so I could fully relate to the user and influencers creating their own voice skills. By bunching content creation––which I have expertise in––with the technology, I was able to quickly overcome my hesitancy, ask questions confidently, and develop a great product. Creating an initial prototype, rather than just theoretical questions, really made a difference in the end.
My Advice: Fail fast, fail early. Ask for help early and don’t be afraid to say, "I don't know." Yes, we go through many iterative processes as entrepreneurs. But you can considerably save time and resources when you ask for help. A lean enterprise is much more fruitful and has more longevity than one built through the sole lens of one person.
Yewande Faloyin
Founder and CEO of OTITỌ Leadership Coaching & Consulting, an organization that coaches serial high-achievers and ambitious entrepreneurial leaders to accelerate into more impactful positions.
How Asking for Help Supercharged My Journey: Asking for help has 100% fast-tracked my business. I remember early on hesitating for fear of bothering people, affecting long-term professional relationships by asking for favors, or not knowing what I was doing. But that was not the case. People were excited to help and hear about what I was doing. It helped me fast-track my growth by leveraging other people's skill sets and providing me with more space to do more of the CEO-level strategic stuff.
My Advice: Recognize that asking for help is not a one-way street—it is often very beneficial to the other person. Find the win-win and put that forward. Not sure what the other win is? Then just ask. Be genuinely curious about what's top of mind for them and then say something like: "Thanks so much for your help—I really appreciate it! How can I support you with what you're doing?"
Kodi Berg
Founder of EQUIPT, a fitness company that fuses functionality with design to create fitness tools you want to use.
How Asking for Help Supercharged My Journey: When I pivoted careers, I had no background in business, product design, or materials. I simply knew what I wanted to create. I started hanging out in steel yards and would be forthright: I don't have experience here but am curious about x—could you help share a bit of knowledge? Keep it short and sweet and be gracious.
My Advice: Intellect is relative. If you are embarrassed by not knowing, remind yourself that more often than not you will discover people are happy to help. And one answer can lead you to another. Follow the rabbit hole.
Grace Blacksea
Founder and CEO of Quench Collective, an online community and education platform for modern leaders.
How Asking for Help Supercharged My Journey: In the first three years of running my business, I was wary of asking for support as I felt I wasn't ready for it. When I finally invested in support, my business became magnetic. There was an energetic shift around finally letting my guard down to ask for help and allowing someone in to help me strengthen the areas I felt were challenging. After investing in support, it made it easier for me to ask for help in other areas of my business and my life.
My Advice: There are so many people out there who deeply desire to support you in your journey—let them in to help you. The more you practice asking for help, the easier it will become.
Nilima Achwal
Founder of The Female Founders Lab, a virtual support and capital ecosystem for venture ideas that can radically transform industries.
How Asking for Help Supercharged My Journey: As a purpose-driven founder, I never fit into the mainstream tech accelerator ecosystem. I overcame this by investing in personal support from coaches who could really see and hear me and quickly get to the root of the challenges I was facing.
My Advice: Invest in real transformative coaching and mentorship from those who can see and hear you, and don't seek validation from those who can't.
Hannah Nieves
CEO and Founder of Hannah Nieves, a consulting agency and education platform that helps luxury brands and entrepreneurs elevate their brands.
How Asking for Help Supercharged My Journey: I hired three full-time team members within three months in my first year of business. Since then, our business has been able to scale even quicker and surpass milestones I would have never imagined.
My Advice: Look at the opportunity cost. What could you be doing with your time if you had more time in your schedule? I know it can be hard to ask for help or get support but think about how it could propel you and your business forward quicker.
Sara Shala
Founder of Sara Shala jewelry, a jewelry brand that is built on appreciation for traditional craftsmanship and high-tech production.
How Asking for Help Supercharged My Journey: Asking for help and constructive criticism has improved my business. You never know what blind spots you have as you grow your company.
My Advice: Be brave and ask. You'll be surprised how willing people are to help, and let them know that they can always reach out to you for help as well.
Tara Ghei
Founder and CEO of Romp + Tumble, a company that curates and rents bundles of eco-friendly baby clothes.
How Asking for Help Supercharged My Journey: Asking for help builds connections in ways that I never expected. By talking to other founders, we've been able to uplift each other with partnerships and word of mouth. It also helps to get the creative juices flowing and think out of the box.
My Advice: Practice asking the question to someone who you trust. Get their reaction or ask them to help you frame it differently if you are uncomfortable. And then just do it. The worst that can happen is someone will say no—and honestly that doesn't happen very much. Most people want to help in any way they can—small or big.
Amanda Black
Owner and Founder of The Solo Female Traveler Network, the largest global community for women who travel solo.
How Asking for Help Supercharged My Journey: The most valuable lesson I learned from asking for help is that I’m not alone in this entrepreneurial journey. Asking for help has helped me realize that people love what I work so hard to create and they actually want to be involved. It’s made all the difference for my happiness level.
My Advice: Help others! It will come back to you tenfold and you’ll probably make some great, like-minded friends along the way. Remember that you built something incredible that people will be honored to be a part of.
Muirelle Montecalvo
Founder and CEO of Vacayou Wellness & Active Travel, an online travel company specializing in wellbeing retreats, spa getaways, and active adventure.
How Asking for Help Supercharged My Journey: Asking the right leaders in my space to be part of my advisory team has been game-changing. For example, when COVID-19 brought the travel industry to a screeching halt, having those experts to turn to led to the continued growth and success of our company.
My Advice: Trust your intuition and don't be afraid to seek external advice. Believe in yourself and your abilities and stand up for what you believe in. Don't let others hold you back.
Heather Falconer
Founder and Creative Director of hatchers.tv, a think tank with a global network of creators in the arts, technology, and sciences.
How Asking for Help Supercharged My Journey: Asking for help created my career. I started my first business when I was 21, which I sold in 2016. That business never would have reached the heights it did without the help of others.
My Advice: People enjoy helping others. It's part of our human nature to connect, form relationships and collaborate. Consider the benefits to the other person—how can you both learn from each other and skill swap?
Jessica Greenwalt
Founder of Pixelkeet, a web development and content management company that works with the biggest names in tech to design, build, and launch products that change the world.
How Asking for Help Supercharged My Journey: It took a few cycles of experiencing the pain of being a bottleneck for me to understand that I needed to step back, ask for help, and rely on my teammates. Trusting them to do what is best for our projects allows me to focus on what I do best, frees up my time, and frankly makes me more enjoyable to work with. Getting to a point where I could ask for and receive help has given my team and our projects the room they need to scale, ultimately expanding the influence of our work.
My Advice: Experience is the best teacher. Keep putting yourself in situations where you have to ask for help to succeed. Work on goals that are so big that you have to get help from others to achieve them, and that you are so incredibly passionate about that you are willing to overcome your issues around asking for help.
Stephanie Danielle Alexander
Founder and CEO of En Soleil LLC, an urban retreat in NYC where guests can relax, refresh, and store their bags between events without needing to commute home in between.
How Asking for Help Supercharged My Journey: Asking for help has allowed me to see that others have a lot to offer and that people actually want to support me and my business. Asking for help has shown me that business doesn’t have to be cold and unfeeling—it is very personal. When you’re able to build a genuine rapport with someone, it’s easier to ask, and easier for them to say yes.
My Advice: The worst anyone can say is no, so step out of your comfort zone and just ask. At the very least it will give you clarity as to who truly is there to support you, and who isn’t.
Candice Smith
Founder and CEO of French Press Public Relations, a business that builds and executes impactful visibility strategies for high-growth social impact startups.
How Asking for Help Supercharged My Journey: When you're building a business that is trying to change the world, you have to be open to feedback. It's not possible to move mountains alone. I had to seek out and build the support system around myself that I could. That is why I credit most of my career progress to support networks like Dreamers & Doers, Spiral5, and The Upside. The guidance I have received when I have faced roadblocks throughout my journey has been invaluable to my growth.
My Advice: If you are an entrepreneur struggling to ask for help, then you may either be struggling with ego or overwhelmed. First, admit to yourself that it is OK to ask for help—you don't have to be an island. When you are comfortable with the idea of asking for help, but don't know where to begin, brainstorm a list of every teeny, tiny task that you need help with. Get very specific and granular about your list. By the end of this activity, you should have a good idea of which tasks you either need to delegate or find support for.
Jacqui Barrett
CEO and Founder of The Bright Arc, a data advisory and consulting firm that helps high-growth, mission-driven tech companies unlock the full potential of their data.
How Asking for Help Supercharged My Journey: I set the goal of having 100 conversations with people who were thriving in all aspects of their life and took notes on everything that resonated with me. Through this process, I realized that I wanted to start my own data and analytics consulting firm in a way that allows travel and the arts to be a more central part of my life. I was connected to so many incredible people and resources that I wouldn’t have known about otherwise.
My Advice: When asking for help, try to find ways that you can also help the person who you’re approaching. Ask them what their goals are and really listen. Don’t discount the ways your own network or knowledge can make a difference.
Dana Kaplan
Founder and Owner of Developing Empathetic Education with Dana, a company that propels children and adults through rich social and emotional learning and intelligence.
How Asking for Help Supercharged My Journey: I embraced my fear of asking for help by focusing on infinite opportunities and possibilities ahead. Friends became mentors, sharing their expertise––and, despite the pandemic––my business went from a dream to reality.
My Advice: Make a list of all you want to accomplish and experience in your business. Immediately circle the must-haves, and list all connections that will propel you toward executing your dreams. Most importantly, ask again and again until you receive.
Kristine Locker
Founder and CEO of Locker 2.0, Inc., a Chrome extension and social shopping platform that allows you to save, share, and recommend favorites across hundreds of brand websites.
How Asking for Help Supercharged My Journey: At times, asking for help can feel extremely difficult due to the internal dialogue we have that tells us that doing so is admitting defeat. I acknowledged my weakness in the marketing realm and reached out to a fellow alumna of Southern Methodist University, Emma Paye. Emma's expertise has helped me build out Locker's social media marketing, which continues to help us grow.
My Advice: Just remember that everyone having different strengths and weaknesses is what makes the world go around. In acknowledging this, you will be able to build the necessary community around you to set yourself up for success.
Kristen Carbone
Founder of Brilliantly, a platform that helps women with the transition from confronting breast cancer to embracing life.
How Asking for Help Supercharged My Journey: The first thing I did when I thought about starting Brilliantly was make a list of the things that I'm not good at and another list of the people I knew who were experts at those things. Then I invited those people over for a brainstorming session, which became the first meeting of what's now my advisory board. Admitting I needed help right from the get-go and having a network of thoughtful experts to guide this process has been an absolute game-changer.
My Advice: Collaborating, brainstorming, and having a diversity of ideas is honestly the best way to improve the process of building a business, product, or community. Learning to ask for help and engaging people who are experts helps with everything from burnout to fundraising.
Gracie Thomas
CEO and Principal of Gracie Thomas Agency, a brand development and consulting agency for modern, luxe, female-founded brands.
How Asking for Help Supercharged My Journey: When I started my first business, I thought that asking for help was a sign of weakness. After selling that business, I crashed with exhaustion and said I would never be an entrepreneur again. It took an autoimmune disease diagnosis and constant entrepreneurial itch to send me back into entrepreneurship. This time, I promised myself I would ask for help every chance I got and outsource what drains my energy. I can proudly say that our business growth has skyrocketed compared to my previous business, and I'm working a quarter of the time. Asking for help has allowed me to be creative, innovative, and forward-thinking so that I can lead our team to the best of my ability.
My Advice: Put your personal fears, ego, and desires aside and think about your actions as the business' actions. By asking for help, you are making the most efficient and safe decision for your business, which is what all CEOs should strive to do. Understand that asking for help is not failure and that it actually can benefit your reputation within your company and in your community.
Lily Scott
Founder of Lily's Ladle, a soup company that crafts frozen bone broths with ingredients sourced from Southern New England farms with sustainable farming practices.
How Asking for Help Supercharged My Journey: I reached out to a presenter from a food incubator program I'd graduated from two years prior, and he was immediately responsive. As a result of sending one email with a question about margins, I found an advisory board of engaged leaders in my industry, and ultimately strategic investment partners.
My Advice: First, ask a targeted question and prepare for a closed, direct answer. Then, have a backup question that is broader in scope and can spark a larger conversation between you and your contact. In this way, you'll get your problem solved and open the door for further conversations.
Elizabeth Entin
Founder and CEO of WTF Just Happened?!, a book, podcast, and brand on Liz’s exploration as a sciencey-skeptic into any evidence of an afterlife and an honest approach to grief.
How Asking for Help Supercharged My Journey: I make getting help a priority instead of a “once I have funding” thing. I hired people to help with branding and SEO, I joined a writing feedback group and a business coaching group, and I also reach out to my community in places like Dreamers & Doers where I ask for help and feedback, as well as offer it.
My Advice: Join entrepreneur communities and trade knowledge. It is not only fun to help others but you form friendships and people want to help those who also give. Hire someone for a few consulting sessions if you cannot afford to hire someone full-time. That is also a great way to build relationships so you have an idea of who you would want to hire once you do have funding.
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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