18 Trailblazing Women Share How They Successfully Created a Life With Immense Freedom and Flexibility

From turning side hustles into full-time jobs, adjusting business models, and everything in between, these women are creating the life of their dreams each day, and have tips for how you can too!

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Many of us crave a life of freedom and flexibility. Whether that involves working for yourself instead of someone else, spending more time on travel or passions, or removing the upper limit of your salary, it’s normal to want to call the shots. However, the appeal of these types of freedom doesn’t necessarily make them easy to achieve. In fact, it can be quite difficult to break the mold of how we’ve been living our lives in exchange for how we want to be living our lives.

At Dreamers & Doers, we are all about challenging the status quo and turning our big dreams into reality, which is why these women are in the perfect position to weigh in on how they’ve successfully added immense freedom and flexibility to their day-to-day routines, and how you can too. 

We hope the following pieces of advice catapult you into living the life of your desires. There is no moment like the present to create your ideal reality.

Shinjini Chatterjee

Founder and CEO of Headlamp, a platform to discover and book female nature and activity instructors outdoors.

My experience: Last year, I left my safe lawyer corporate job to start my own business and write. It was a scary, exhilarating, and transformative decision. The best part of the transition has been claiming ownership of my career and creating a future I believe in. 


My advice: Listen to your instincts, do some soul-searching, and then form a plan. Recognizing that you aren’t feeling fulfilled at work is valid and powerful. But before you jump ship, I recommend visualizing what kind of life you want to lead and then strategizing what changes you can make to get there.

Katie Hawkins

Creative Director at Here For Good Films, a video production company on a mission to tell stories about people doing good and leaving their communities better than they found them. 

My experience: I work hard but I also play hard. I travel often for work but it’s very common that I take a few days on the front or back end for some scheduled play around business calls or edits. Sometimes, I decide to just come home. Having the flexibility and freedom to choose my next adventure is one of my favorite things about being a business owner.


My advice: Try saying yes. You’ll be amazed at how far “yes” can take you—to new experiences, new opportunities, and new adventures. Any time you try something new, freedom and flexibility won’t be far behind.

Tiffany Yu

Founder and CEO of Diversability LLC, a community whose mission is to elevate disability pride through community, visibility, and engaged allyship.

My experience: The pandemic made me realize that my work could be remote. Today, I run my community business, Diversability, which supports our team of 10. I am also a speaker and a content creator. I call this “creative entrepreneurship.” I also made a smart decision in my 20s and ended up purchasing a piece of residential real estate. That rental income enables me to have passive income to pursue passion projects.


My advice: The majority of your income doesn’t have to come from one place. I used to feel a little bit of shame that I wasn’t generating enough income from one place to support myself, but I took a great masterclass from Arlan Hamilton on creating multiple income streams and it made me realize that it was my combined income that mattered. Take the time to write out all of the places where you generate income. If it isn’t yet enough to support yourself, do you have the capacity to create a new income stream for yourself?

Christina Lopes, DPT, MPH

Founder and CEO of Christina Lopes International, a fast-growing purpose-driven company focused on the advancement of human consciousness.

My experience: When I first became an entrepreneur, I thought that freedom and flexibility came naturally through no longer having to answer to anyone but myself. But I was sadly mistaken and it took a complete burnout for me to define what flexibility and freedom truly mean to me as an entrepreneur. Today, it means jumping off the hamster wheel of constant action, doing, and hustling. Freedom and flexibility now mean that I am growing a highly-impactful, purpose-driven company without the need to constantly be pushing myself beyond my limits. It means structuring my entire business around the mission of serving others and creating abundance while I sleep. 


My advice: Prioritize your health and well-being above all else. Without that, your impact in this world will diminish.

Dina Kaplan

Founder and CEO of The Path, a meditation community.

My experience: I was tied to New York for the first five years of running my company, and I felt like I could do an hour of meditation a day and still not advance on my practice. I wanted to liberate myself from needing to be based in our headquarters. After a year of work with an extraordinary strategy consultant, I was free! Now instead of in-person weekly practices and month meditations, we host a once-a-year retreat and a wonderful online meditation teacher training program. I feel so grateful that I can travel full-time and continue building my company from the most beautiful places in the world. 


My advice: If you can’t find a way on your own, I highly suggest hiring someone with a big picture, strategic view of your life and company products. Sometimes an outside consultant can see things that you can’t, and their fee is worth every penny.

Jessica Sikora

Founder of Rou Collective, a full-service creative agency dedicated to building unforgettable brands and designs for social good.

My experience: I quit a six-figure corporate job to bet on myself. I was burnt out and couldn’t land a role where I had the freedom to be creative, so I took my side hustle as a digital marketer and creative strategist full time. For the first time, I was able to use my outside-the-box thinking to help brands thrive, and was being celebrated for my creative thinking and unique designs. Today, just six months after transitioning to being my own boss, I have a fully-booked client roster and am out-earning what I ever have made in the past, all while working on my own terms and around my ideal schedule.


My advice: Know that it is possible. I spent far too much time admiring others who have this freedom and flexibility, wishing it was me, not realizing that this was possible for me in my own unique way. Dream big and chase building a life that is truly possible for you!

Gabrielle Thomas

Founder and CEO of GT Consulting, a practice management company for health and wellness practitioners.

My experience: Freedom and flexibility starts with my mindset. I like to qualify opportunities by asking myself if it brings me joy, is it within my strengths zone, and will it help me to achieve my primary aim. Doing things because “I want to” or “get to,” not because I have to has been my ultimate freedom. 

 
My advice: Pay attention to what feels restrictive. How does your body react? Then pay attention to what feels good. When you get to know what feels good, do more of that. When you align your intentions with your actions, you have control over the outcomes and ultimately your happiness. Your business is a tool for your happiness.

Arielle Shnaidman

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

My experience: Working for myself has allowed me to work when and from where I like, but what’s added the most freedom and flexibility to my life is being in complete control of what I bring in every year and who I work with. I’m in complete control of my fee, how many clients I take on, and with whom I work. 

 
My advice: Figure out what freedom and flexibility mean to you. Is it the freedom and flexibility to work when or where you want? The freedom to have ownership around what you can or want to earn every year? Freedom and flexibility to work on different projects, or with different people? Get clear on what you want to optimize for first when it comes to freedom and flexibility.

Chedva Kleinhandler

Founder and CEO of Rooms and Words, a full-stack content and strategy agency.

My experience: After years of being a tech entrepreneur, having to answer to investors, work within the realm of enterprise B2B clients and be responsible for my team’s salaries, the pandemic forced me to reroute my career. I decided to listen to it and introduce more freedom to my life. While I still enjoy managing a robust team globally and being accountable to my clients, my new agency is fully remote, our team is mostly made out of digital nomads, and I have learned from my amazing team members to travel, take time to myself, and enjoy the upside of entrepreneurship with much less of the stress. 

 
My advice: I’d recommend therapy. More specifically, I think questioning the paradigm that makes us think our time belongs to something other than ourselves is a great place to start.

Yewande Faloyin

Founder and CEO of OTITỌ Executive Leadership Coaching, showing high-achievers and entrepreneurial leaders how to confidently accelerate into more impactful leadership positions.

My experience: Having burnt out twice during my corporate life, I consciously created my business in a way that my professional, personal, and social lives all complement and support each other. With this mindset, I’ve been able to create what I previously thought wasn’t possible. I have built an impactful, purpose-driven business that I love, coaching leaders and serial-high achievers to achieve their most ambitious goals. And I do so in a way that enables me the freedom and flexibility to enjoy the big things and the small things.


My advice: Do not aim to create freedom and flexibility in the future. Decide what it is and create it now. It is common for ambitious leaders to believe that you have to push hard in the short-term to achieve the balance, freedom, and flexibility that you want in the future. However, all you’re doing is building patterns and learnings that reinforce sacrificing your freedom and flexibility. If freedom and flexibility means working three days a week, maybe start by working toward four and a half. Or pick three days a week where you end your day one hour earlier than usual. You’ll learn that the “impossible” is a lot more possible than you think.

Sara Banks

Founder and CEO of SteamLine Luggage, creating beautiful leather luggage designed to elevate the travel experience.

My experience: I have taken my family of six abroad. We are now full-time traveling and working remotely. For my business, we have given our entire team full reign on working from wherever they want in order to maximize hours offline as well.


My advice: I hear other entrepreneurs talk about the fear that if they aren’t there, it won’t get done. I have found that actually, it is just the opposite. People work better when they trust and are confident in their work. To maximize more freedom and flexibility in our own lives, we give it to our team members. We trust them to meet deadlines and take on more projects, and keep communication open and flexible like our lives. So far, so good!

Melinda Wang

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

My experience: I believe intellectual and creative freedom are the most vital aspects of life.  Creating a multi-hyphenated professional life that’s both “left brain” and “right brain” has allowed me to have freedom and flexibility to take deep dives into different and seemingly disparate fields. As a corporate lawyer, I help clients solve problems creatively and strategically across industries and corporate life-cycles. As an independent curator, I have the freedom to explore new artistic forms of expression and topics that I believe are crucial. As an angel investor, I focus on the industries and new technologies I’m most excited by.


My advice: Give yourself permission to be curious and say yes to opportunities that intrigue you, even if they might initially be outside your comfort zone.

Sterling Champion

Co-Founder of The SHE Mark, making it easier to identify and support women-led businesses.

My experience: The most impactful way I’ve added freedom and flexibility to my life is through practicing a four day work week. It allows me to prioritize spending time during the week focusing on things like professional development, home improvement, and guilt-free rest. It has also resulted in more productive working hours and equal output of work.


My advice: Give yourself permission to step away from work and focus on activities that are not often prioritized and ones that recharge you. You, your work, your life, and your relationships will be better for it!

Nics Asawasudsakorn

Founder of Nics Design Studio, a Shopify web design and development studio for e-commerce businesses.

My experience: After starting my own fashion brand as a side hustle while I was working at a major tech company, I realized that I wanted to start creating more e-commerce websites for other female entrepreneurs as well. Earlier this year, I took the leap and quit my full-time product manager job and decided to run my website design studio full time. Since then I’ve been able to take Fridays off, go on more trips, and work remotely in Thailand for a month.


My advice: Even when you’re still side hustling, start thinking about what more freedom and flexibility means to you. For example, start setting boundaries and expectations in your email response time or allocating certain days for solo creative work without distractions. You learn what aspects are most important to you as you transition toward the lifestyle that you want.

Christina Salerno

CEO of Magical Teams, a hiring consultancy for small businesses looking to uplevel and build their dream team.

My experience: Freedom is one of our core company values and behaviors –– freedom for everyone to be unique individuals, to do work they love, and to do work in the way that works best for them. The difficulty with freedom is it looks different for each person, and we built a structure to support this freedom. This looks like non-traditional role and responsibility structures, setting a maximum number of meetings per day and “focus block” times, working at 7 a.m. or 10 p.m., unlimited vacation, sick, and mental health days, and loving and looking forward to Mondays.


My advice: Create an appropriate mix of structure and flow where kind communication, treating each other like adults, and clear expectations are at the center of the way you work together.

Sally Wolf

Founder and CEO of LightWorks, empowering executives and their teams to flourish both professionally and personally.

My experience: We often have much more freedom than we realize in life, particularly when we choose to see the ways in which we can be flexible and creative to honor our own needs as well as those of our teams. Back when I was a corporate executive and regularly traveled to Los Angeles, I cherished a Monday night dance class at home in New York that was a great source of both physical and emotional wellbeing. Almost always, even when my boss or team chose to travel Mondays, I could manage my calendar so that I flew out early Tuesday. It took me a full decade in the corporate world to realize I could honor something personal like a dance class I loved, and that there is almost always a way to honor our personal and professional needs simultaneously and flexibly.


My advice: Having the self-awareness to know what truly matters most to you and then fiercely protecting those things on your calendar brings an incredible amount of freedom to our lives. While it can often feel easier to keep our sources of freedom private, in my experience the more transparent we are the easier it is for us—and our colleagues and clients—to honor these parts of ourselves.

Katherine Sprung

Executive Producer of Sprung on Food, a web series highlighting small businesses in the food and beverage industry.

My experience: I changed my business model! I’ve been running my business, Squish Marshmallows, for eight years. I started with e-commerce, pop-ups, and a bit of wholesale. After two and a half years, I opened up a brick and mortar that I operated for five years, along with pop-ups and satellite locations, catering, e-commerce, and delivery. My lease was ending in mid-2021 and I decided to not renew. This was my chance for a new start, to revisit how I wanted to operate my business, and switch the model to bespoke custom and catering orders only. This way, I could accept serious orders only, which would free up a lot of my time to explore other passions and ventures, like freelancing in food media, content creation, starting a web series, and being able to see friends, explore my city, and travel for fun.


My advice: Look at the bigger picture of what matters most to you in your life. Be comfortable with exploring the idea of changing your path, to pave way for that freedom you’re looking for.  Cut down hours, say “no” to things that don’t serve you, or rethink the way you currently operate!

Kinsey Wolf

Founder of Lane Collective, a growth strategy consultancy for future-focused startups.

My experience: In early 2021, I was experiencing burnout as a marketing consultant, even while doing work that I love. Something had to change. I made the decision to prioritize my lifestyle and relationships. To do that, I set a goal to work 20-30 hours per week while doubling my income. Now, more than one year later, I’m proud to say I’ve surpassed that goal. Today, I’m leading a successful marketing collective, and working with some of the most impressive founders around.


My advice: Think deeply about what matters to you, and what’s truly blocking you from a life of your own design. Solve for the non-negotiable—in my case, that was mental space—and be ready to make some hard decisions.

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