Jaclynn Brennan On Helping Women Find Their Purpose Path

Life's too short to live a life that doesn't light you up! Today's guest has made it her mission to empower women to live a life they love. Jaclynn Brennan is the powerhouse Founder and CEO of Creative Duality Consulting and the Co-founder of Fyli. Fyli is a female mastermind membership community that provides resources, community, and support for early-stage female founders. In this episode, Jaclynn chats with Ellie Shefi about helping women find their purpose path and creating a space for women to grow and thrive. She also shares powerful practices that you can implement to truly become the architect of your life.


Watch the episode here:

Listen to the podcast here:

Jaclynn Brennan On Helping Women Find Their Purpose Path 

Our guest is a powerhouse Founder and CEO of Creative Duality consulting who has mastered living life on her own terms. She's a creative director and global influencer who has worked with over 22 major corporations and luxury brands along with countless leading entrepreneurs to help them efficiently design and execute branding strategies across a wide variety of industries. She designed Serena Williams' first jewelry collection, and collaborated with Lord & Taylor and Bloomingdale's on designing ready-to-wear collections for UNLEASHED, with net profits going to NGOs focused on girls’ education.

Beyond supporting girls’ education, she is also the Cofounder of Fyli, which stands for tribe, a female mastermind membership community that provides educational masterclasses, accountability, peer-to-peer mentorship, leadership advancement, and funding opportunities for early-stage female founders. She is a champion of self-expression and positive body image. She continues to leave her mark as a woman with drive, determination and creative genius to take brands, organizations, and entrepreneurs to their next level of success. Welcome, Ms. Jaclynn Brennan.

Thank you so much for that fabulous introduction. I'm excited to be here with you.

Thank you so much for joining us. You have dedicated over a decade to helping women find their confidence, embrace their beauty and create a life that gives them the time and money freedom to live a balanced, joyful, and abundant life they love. Where did that passion and drive come from?

This is something that has been cultivated over the years. When I started my career, my passion was definitely fashion, helping women feel good and confident in their skin. As my career developed, I had some amazing mentors that empowered and showed me that we could use fashion for good and that our net profits can give back to local organizations. They helped me pave the way into my focus of what I do now. My whole mission is the advancement of women. My personal mantra and mission, as well as Fyli, is to help women rise in all aspects of their lives, renew, inspire, support, and empower.

This is definitely your calling. What was that moment when you knew that this was your purpose?

Fyli started off as a passion project. The moment I knew I needed to do this was when being involved in a first tech startup, which was originally a SaaS B2B software with a few male partners. When I felt like I failed, that my voice wasn't heard, I didn't understand my vesting schedule, I didn't have the right lawyers, and I didn't know how to raise capital. When I felt that inkling of failure from that tech startup, I knew I needed to do something to support other female founders and past the roadmaps, so they wouldn't make as many wrong turns as I did. I created this business along with my Cofounder, Summer, because it's something that I needed.

Failures are so important in this journey of entrepreneurship. We need them to grow, to learn, to get better.

How would you help someone find their purpose and step into their calling?

I feel my unique gift and secret sauce is to help individuals find their purpose path. That's truly what I do in Fyli and the consulting side of my business. It's more than just a job or a career, but something that connects them to their soul, values, gives their life meaning, and that is what I do for individuals. I help them find that purpose. It took me a very long time to find mine, and that's how I can empower other founders.

How would someone use their creativity and skillsets to create their own career of their dreams and live into their purpose path?

It all starts with belief. The first part of being the architect of your own life is deciding that you are capable of creating your own life circumstances. You have a choice every day. I'm a huge believer in manifestation, creative visualization, feeling it, dreaming it, but then helping individuals put in the actionable steps that they have to take to achieve those dreams and goals.

Talk about that moment in that tech startup. When was the first pivotal moment where you decided that you wanted to go into business for yourself and become an entrepreneur?

I remember that clearly. That was 2018. I had a wonderful career in fashion as a creative director. I worked for some fantastic leaders that were great mentors to me. I remember saying to myself, “I have built everyone else's business for over a decade. Now it's time for me to create my own.” I was very naive in that thought process, but I started consulting while working full-time. I always tell founders this, “You have to build your network. You have to have a reliable and secure income as you're in that transition period to go off on your own.”

I remember feeling so invigorated and excited to dive into startup life. I wasn't fully prepared for it, but I do feel like there are some interesting steps that one should take as they're in the midst of that transition to get to running a business full-time. That's about financial planning, putting your team in place, and figuring out how you're going to sustain your income while you're in that transitionary period.

What was the biggest obstacle that you faced, and how did you overcome it?

One, I can always say that I reframe failures into discoveries. Failures are so important in this journey of entrepreneurship. We need them to grow, learn and get better. I don't think that I made the right decisions when I was leaving my full-time corporate job and going into entrepreneurship. I learned from those failures and discoveries for my transition personally. I believe it was not agreeing or seeing eye to eye with my cofounders or my male partners in this tech business.

I didn't find my voice. I wasn't speaking up or advocating for myself, and I didn't feel prepared. That was that pivotal moment of feeling powerless and not heard, feeling like I have a fire within me that's going to fuel this passion to help other women, to give back, find the mentors and resources even that I needed to move forward in my career.

What did you do to find your voice? What did you do to harness that fire in your belly and to break free and say, “I am tired of being unseen, unheard, unvalued, or disrespected?” What did you do to step into the bravery and boldness of using your voice and making that next transition?

The first piece of it was that I believed in myself and that I could create the life that I wanted. I then made an action plan. I thought about, “What are the resources that we need as women? What are we lacking?” I started doing research on it. I visualized it, prayed on it, meditated it, dreamt it, felt it and then I started to look for opportunities. I started to educate myself to see what was on there on the market, what resources I needed, what classes I needed to join, what other groups were out there and happening. I started to seek out mentors and connect the dots between what I thought I needed, what I truly needed, and what was missing from my life.

Believe that you can, and find people who are further along in your journey who can help you. There's no need to reinvent the wheel. Find a community like Fyli or a mentor who can say, “Take my hand. Journey alongside me and let me help you go further, faster,” while avoiding all of the costly mistakes that they have made along their journey. Now that you've done that, what are your biggest tips for staying in that alignment, in your power, disregarding and silencing the critic in your head, breaking through the limiting beliefs that may arise from time to time? How do you do that?

The first piece that I want to start with is learning how to ask for what you want and what you need. Culturally and as a society, women are taught from a young age, “Don't ask for things. Be polite. Say yes. Say thank you. Don't ask for too much. Don't be too much.” My number one piece of advice is to start asking for what you want, what you need, and accepting help from individuals. I believe that there is such power in making your ass and also being able to receive.

Structure sets us free.

Another big piece of this is creating the structure so you can have the freedom that you want in your life. Something interesting in the overall design principle, the decision-making structure consists of things like rules, agendas, mandates and plans. When these things frame our choices, it frees us to focus on our substance of work. I always say, as a creative, who manages more than one business, structure sets us free. It's creating those routines, plans, and structures that help us feel our most free and do our best work.

In touching on structure, self-care is critical. You need to fill yourself up before you can effectively support your community and clients. What do you do to refill your cup?

The number one thing that I do to refill my cup is my morning routine. I started doing this many years ago. I need it to keep my consistency and to refill my own cup before I can even start my day. I wake up early. I spend an hour exercising. I do twenty minutes a day of meditation, then I journal and I write through, “What are my goals? What am I going to achieve today?” I take a moment for gratitude. I do this almost every day, at least six days out of the week. I try to stick to it. Sometimes it goes to shit, or it's hard when I'm traveling, but I do my best. That gives me the structure to then create, be present, be patient and bring my best so I can show up for the work that I do.

Another big one is taking time for myself, creating healthy boundaries, not sleeping with my phone, not looking at my phone first thing when I wake up because then I'm automatically reacting. It's setting my intention and starting my day by choosing to bring joy, happiness, and gratitude into the moment. That's crucial for me, and that took me years to learn how to do that instead of going and reaching for my phone.

It's also about giving myself space and time to play, think, dream, create and travel. As an entrepreneur, I know that can be challenging because you feel pressure. You have deadlines. You have to get stuff done. You feel guilty for not always working, but learning that time to dream, play, and create makes you a better leader. I make time for that for myself too. I schedule it in my calendar like I would a business meeting.

To everyone out there in the audience who says, “I don't have five minutes in the day to meditate, to journal, to exercise or to go and play,” what I hear you saying is, “Prioritize yourself. Make time for that because when you do, you'll be much more efficient, present and focused on the rest of your day. You can increase the amount of time, metaphorically speaking, that you have.” What would you say to someone who says, “That's all well and good? You talked about boundaries and asking for what you need. What if I don't know how to do that?” What is something that you would say for that woman out there who is feeling trapped and unsure of how to begin the process of prioritizing herself, establishing boundaries, finding and using her voice? What can she do now?

The first thing I’m going to say, get comfortable feeling uncomfortable. That is when you grow. Number two, find your tribe. Find people that are going to motivate you, inspire you, challenge you, hold you accountable. If you don't have the funds to join a professional mastermind group or the time, build your own tribe, make an accountability group, show up for the people around you because together, you move mountains if you're more powerful collectively. Find that group that's going to give you energy.

The last thing I'm going to say is you are the architect of your life. You create the life that you want. You choose joy or stay in a job or a relationship that you hate. You choose not to have time or create time. Everything we do in life is a choice. You could make better choices and surround yourself with individuals that can help you learn how you do that step-by-step.

Piggybacking on that, what's your biggest tip for making that mindset shift so that you can make better choices, decide, commit and take action to follow through?

I'm going to say how I did it personally because it took me a long time to trust myself, understand my voice and learn how to do that. The way that I can say I started was to make promises to myself and start keeping them. Once you start making promises to yourself, even if they're small, “I'm going to go to bed at this time. I'm going to wake up early. I'm going to commit to exercising. I'm going to commit to this meditation.” When I do those things, I tell myself I'm going to do them and then I show up for myself. I trust myself. My intuition feels good, then I can make better decisions. I can listen to my inner voice. I can tap into my guides, meditate and spend time with myself.

Once you do that more, you build a relationship with yourself. It becomes easier to hear the voice, trust yourself, make those decisions, but like anything in life, like riding a bike, being an expert is you have to practice. To be considered an expert in something, you have to put in 10,000 hours. How do we become experts in listening and trusting ourselves? We got to put in the work.

You've talked a little bit about Fyli, but tell us more about how it came to be about some of the incredible things that it has been up.

I love what I do. I feel blessed and grateful to wake up every day and run this amazing community, this tribe, this family with people that I love. Fyli has been operating as C corp. This started out as a passion project. My co-founder and I met at a Female Founders Pitch Event at the New York Times. We built our friendship and relationship. We started doing a lot of research. Our original goal was, “Let's join a mastermind group together so we can hold each other accountable.”

We found that the average buy-in for these groups was $50,000 to $75,000 per year. They were male-dominated and they only met once a quarter. We saw more traditional organizations, which are amazing, like YPO. You have to have $2 million in revenue, and a certain amount of employees, or you have organizations like Chief, which are also great. They focused on corporate executive women.

We are all capable of greatness. We were all created with a special gift, talent, and ability. That's what makes each of us unique in this world.

We found that there wasn't a lot in the space for early-stage female founders, except your accelerators, which are all fantastic. What's that starting point for women? How do you enter into that? How do you build your tribe and community? We both needed it ourselves. We started a product because we needed it. We never imagined how it would grow and expand into a global business, 8,500 women globally. It has been an incredible journey to watch this idea of something that we both needed turn into something so much larger with a bigger global vision.

To the state, Fyli has given over 150 free masterclasses. We've helped our women raise capital in their pre-seed seed and series A round. We've prevented burnout for so many members. We've been there to support them in terms of life crises or financial situations. We've supported over eighteen local nonprofits financially through our Active Listening or Resilience To Rise series. We're excited. We're expanding into Shanghai, China, in Q3 2022.

This is definitely a global mission. When we first thought Fyli, we were operating like a mom-and-pop shop. It’s very one-off focused on human connection, which we still are focused on human connection, but now, I look at this as a global NaaS business, Network as a Service, that has a true ability to scale 10X and make a huge impact in this world. I'm very excited to see this journey and how we transition and keep helping early-stage female founders get that support that they need to show up and do their best work in this world.

One of the things that I find most powerful about that is that all of this was done during COVID. For Fyli to explode means that all of these female founders who are in your community have been able to weather the pandemic together. They've been able to pivot, diversify, build their dreams and their businesses because you started this and you have shown up powerfully throughout this pandemic.

At a time when people have been silenced, people's communities have been disrupted, their outlets have been disrupted, businesses have been going down the drain and people have been getting laid off and there's been more and more isolation, you and Fyli have been able to create community, connection, and the space for people to flourish. I honor that. What has been your secret sauce to do that during the pandemic?

Nothing great is ever accomplished alone. We have such a powerhouse founding team, my Cofounder Summer Yanyi Li, our COO and Head of House, Catherine Szpindor, our Community Manager, Mi'a Callens and our Digital Media Manager, Alyssa Stratford. That's the core team. We have moved mountains together. During COVID, we had two decisions. We close shot, or we put everything we've got into this business and give it our all. In March 2019, New York City shut down. We were operating Fyli with in-person events only based in New York City out of Soho House, who was our pilot partner, and we made a decision.

Within 24 hours of the shutdown, I winded up calling every mentor and amazing human in my life and said, “Would you give 30 to 45 minutes of your time to give back and empower our community?” We need masterclass sessions. We need to hear from leaders. We need inspiration. We made this free for eight months for everybody who wanted to be a part of it, male, female, or however you identify. We decided to lean into the community, make it free and open for everybody and keep pumping value at a time.

That was tumultuous and tough for many of our members. After COVID, we leaned into our business model. I don't even want to say after COVID because we're still going through COVID. There are still so many unknowns, but we transitioned into two products for Fyli. Our close cohorts, year-long commitment, small groups of up to ten women, and our fully virtual online subscription community. We dived into a strategy and a plan. Before we did that, our number one thought process was, “How do we give back and make an impact for these people?

What would you say has been the biggest challenge that you've seen within your community? What are the female founders struggling with, and what has been the smallest hinge that swung the largest door for them and navigating those challenges?

The obstacles that we see when they start are surrounding imposter syndrome, raising capital, knowing how to ask for that, and feeling confident being the leader or leaving their full-time job into entrepreneurship full-time. Those are the things that we see our women struggle with. Within the first two months, throw that out the window because they gain a global community of support. They feel empowered, confident and ready. That work is so purposeful.

What's your biggest tip? Imposter syndrome is probably one of the largest obstacles that people in the entrepreneurial space, coaching space, speaking space tend to face. How do you navigate your members through Imposter syndrome?

I would like to give a very simple solution, even for myself, how I worked through imposter syndrome because we all have it. It's there. I have my days as well. I simply have a note on my cell phone that I will look at when I am feeling not my best to remind myself what I'm capable of and what I have achieved. I write this little note to my future self. I look at that on those days that are tough. I remind myself of my power. I also want to shout out one of our cohort members in our icons cohort, Katie Fink, who does video recordings of herself.

She'll probably do this once a week or once a month. She'll say her mantra and remind herself her strength, power and play her own voice to herself. That helps her conquer imposter syndrome. That's something we've all been doing because it's peer-to-peer mentorship. We learn through each other. Those have been some helpful tools on how you can deal with it daily. Those little notes and reminders, voice recognitions on, “You are strong. You are capable. You are powerful. Look at what you've been through. Look at what you can achieve.” That helps.

Those are powerful, easy-to-implement, actionable tools. You've given us many golden nuggets already that people reading can implement immediately. You've got make a decision, decide, commit, take action, set up a routine, stick to your routine, make it a non-negotiable commit to your routine, leaving yourself notes, the voice recordings. That's all powerful.

Surround yourself with people who are going to call you out.

What is an actionable tip that you can give for people who might still be caught up in the external and in living to satisfy other people's expectations, demands or beliefs? What would you say to them to shed that so that they can come home to themselves and decide for themselves who they are, what they stand for, and how they want to show up in the world?

They have to make a choice to believe that they are capable. We are all capable of greatness. We were all created with a special gift, talent, and ability. That's what makes each of us unique in this world. Number one, believe that you're capable. Number two, write your plan, create a plan, stick to it, take actionable little steps every single day to get closer to your plan and vision, whether that's setting better boundaries for work, advocating for yourself as you're growing your career, finding your mentor or accountability partner to help keep you on track and just keep educating yourself, read things that help you grow, get comfortable, feeling uncomfortable, believe in yourself. Keep those promises with yourself every day because that's how you grow. It's a constant learning process. We all don't know it all. Every day we take little steps to get better.

What steps are you taking to continually evolve and make progress along the plan that you have for yourself?

First of all, my hardest critic and the person that holds myself accountable is challenging, feeling weight and pressure to be on, to be looked at as a leader or a role model. Sometimes I have my days where it's quite challenging for me too. I surround myself with experts and individuals that helped me show up for me.

That's therapy, having a fitness and nutrition coach, having my amazing group of friends that I exercise within weekly classes, and having my team and my partner to check me, my love and life partner and my business partner to say, “You're a little stressed out this week. You need a break. It’s time to put your computer down. Spend some time, take a walk, put your phone down.” We all need those reminders. I surround myself with those people who are going to call me out because sometimes I need it to.

Surround yourself with people who will call you on your stuff, who will put the mirror up to you when you need it, and who will do so lovingly. It is such an important takeaway that everyone can keep in mind. What's next for you?

I'm not much of a resolution maker for New Year. I'm an intention and a goal setter. I have so many personal and professional goals for myself. Personally, setting boundaries, taking more time for play, even more time to have fun, enjoy, unplug, recharge, plant my roots in this city of Austin, Texas, build and grow my own family. That's exciting.

Professionally to continue to show up for my clients, our members, investors, advisors, to be a true leader, to walk the talk and put the action and the steps behind it. I also have some exciting projects that I'm working on that I can share more about in the NFT space that are very thrilling for me because I love to educate myself on new technology and what's happening in the market.

Let's fast forward, and it's coming toward the end of a life best live. You have lived the life of your dreams. You've left it all on the table. What do you want your legacy to be?

The amazing women that I serve and support, my legacy is them. I want to see this next generation build and grow their businesses feel empowered to ask for what they want and need. I want to see women raising more capital, way more than 2.7% of venture capital, especially Black and Brown women. I want to see more women ringing the bell on the New York Stock Exchange. I want to see more women sitting on boards. This is our year collectively to ask for those things and take action to build them.

If you had one message that you want to share with the world that will empower them to reach all of those goals and dreams that you have spoken, what is the one message that you would deliver to them so that they can make your legacy become a reality in their life?

Believe in yourself. You have the power within you. Once you have the belief and you trust yourself, others will too. Start showing up for you. It's all about belief.

Was there a time in your life or a moment where you decided that a belief, a paradigm, or an expectation that you had been raised with or that you saw in society, that moment when you realized, “This is not my path. That is not for me,” and you decided to shed that, change courts and live life for you?

One is leaving my corporate job as a creative director. At the time, that was hard to do. My whole identity was wrapped into that. It was how to rebuild myself? How to stand for what I believe in again? How to create my own core values and mission statement after years of being told, “This is what it is. This is who you are. This is what you represent under this company. This is your public image in fashion.”

Start showing up for you.

Having to shed all of that, throw the ego out the window, rebuild, and go back to my core of what is important to me and how I want to show up for the world was a tough transition and a tough time in my life. That's when I started the tech company when I didn't feel supported or heard or understood, and then shutting the ego of this past life as a creative director, being a big deal, people knowing who I worked for and with. That was a challenging time. It was also very humbling.

Being stripped from your ego and the value that you ascribe to that in the accomplishments, the accolades, the recognition, and then coming home to yourself at that core essence, looking long and hard at, “Who am I without the accomplishments? Who am I without the achievements? Who am I without the labels? Who am I without the accolades? Who am I without the corner office? Who am I really? Do I like her? Is that who I want to be going forward?”

I did not like the person I was. When I left that job, I did not even recognize myself in the mirror. I didn't know what I stood for. I didn't have the right values in place. My life was very materialistic. I literally am not the same person that I am now. In 2018, it was making very big changes, listening to myself, building with myself again, my own internal relationship, making those choices and believing in myself without all of that, without the title, job, support, and finances that I was making. Rebuilding and having that belief is everything.

Isn't it amazing that everything can come from nothing?

That's how we grow, evolve and learn. Those failures and discoveries are so important for the steps that we take in our lives.

The moments of breakdown that then when you come home to yourself, when you reflect, present, open, vulnerable, the magic of the breakthroughs that can happen from that space of real raw, transparent vulnerability is magic. The breakdown to breakthrough. Would you say when you left your corporate world and had to examine who you were, whether that was the person you wanted to be and how you wanted to go forward, was your breakdown to breakthrough moment?

That was one of them. I've had many in my life, as I'm sure I'll have many more, but that was the big one, shedding the ego, rebuilding, starting from nothing. That was a huge breakdown to breakthrough moment. That's where the magic happened. That's where Fyli came from and this little idea that we had to start a mastermind group for women in New York City turned into a global community of 8,500 women. Those are the moments where we make decisions on how we're going to show up and believe in ourselves. That's truly where the magic happens.

When you come to yourself, you get super clear on who you are, what you stand for, what you want your values to be, what you want your purpose to be and bring yourself into that alignment and then show up fully and powerfully apologetically as the force that you are living in that alignment, living in your true passion, purpose, calling, and then serving from that place.

That's what it's been about, putting the community first, building and even scaling with the community in mind and how we can magnify that impact through growth and scale, taking investments, speaking to VCs as we grow in scale Fyli. We always have that human connection and community in mind.

It's the foundation of everything. In your wildest dreams, where do you see Fyli?

I see myself and my team up there and some fabulous Fyli orange power suits ringing that bell, doing IPO on the New York Stock Exchange and making this a global publicly-traded company.

Talk about living life by design, free by design, creating a life that you love and taking thousands of women along the way, helping them create the life that they love, helping them be free by design, having a life that they love that's a life on their own terms that gives them the joy, the balance, the time and money freedom to be all and have all that they desire. How can people find out more about you and how can they connect with you?

I would love to connect with everybody here. You can learn more about Fyli and apply at FyliTribe.com. You can learn about our programs or resources, set up a call with our team. Personally, you can connect with me on LinkedIn or on Instagram, @JaclynnBrennan. I check all of my messages personally. I love hearing from other founders and being able to find ways to support them. I'd love to end with my personal mantra. This is something highly personal that I say to myself every single morning after my meditation, “God is working through me now. I am filled with creative energy. I have everything I need within me. The universe always provides.”

Thank you for what you do, for showing up in the world, creating opportunities, supporting so many. The ripple effect is profound. Thank you for showing up for yourself in that moment of transition when you stripped away the accolades and came home to yourself. Thank you for recognizing the light within you, for honoring your call, and for serving so powerfully.

Thank you for having me and letting me share my story. I'm very grateful.

Important Links:


About Jaclynn Brennan

Today’s guest is a powerhouse founder and CEO of Creative Duality Consulting who has mastered living life on her own terms! She is a Creative Director and Global Influencer who has worked with over 22 major corporations and luxury brands - along with countless leading entrepreneurs - to help them efficiently design and execute branding strategies across a wide variety of industries.

She designed Serena William’s first jewelry collection and collaborated with Lord & Taylor and Bloomingdales on designing ready-to-wear collections for Unleashed - with net profits going to NGOs focused on girls’ education.

Beyond supporting girls’ education, she is also the co-founder of Fyli - which stands for “tribe” - a female mastermind membership community that provides educational masterclasses, accountability, peer-to-peer mentorship, leadership advancement, and funding opportunities for early stage female founders.

She is a champion of self-expression and positive body image, and she continues to leave her mark as a woman with the drive, determination, and creative genius to take brands, organizations, and entrepreneurs to their next level of success. Welcome Ms. Jaclynn Brennan!