In this interview, Callie Kaminskas, Executive Director of Shadow Her, shares how her definition of success has evolved from climbing the career ladder to creating a life rooted in purpose, flexibility, and presence. She reflects on building community, embracing uncertainty, taking bold leaps of faith, and why the most meaningful opportunities often come when you’re willing to let go of having everything figured out.
When Fulfillment Matters More Than Climbing the Ladder
How do you define success today?
I would describe myself as an incredibly hard worker and really ambitious. For a long time, work was a huge part of my identity. Right out of college, I lived on the West Coast in Oregon for about 10 years. When I was 23 years old, they were building a new program to support female student-athletes at the University of Oregon. There was nothing really like it in the country, so I had the opportunity to build something from nothing. I felt both immense opportunity and intense pressure to succeed, and my definition of success was dictated entirely by the metrics of that role.
Today, success feels very different. I have a 16-month-old daughter, so success sometimes just means getting out the door in the morning. Success means being able to see her during the day. It means being fully present when I am with her, not trying to balance vacuuming, answering emails, and cooking dinner all at the same time.
When I am working, success means finding incredible fulfillment in my work, feeling like I am helping others, and knowing I am building something impactful that can grow into something big and incredible. I need to feel fulfilled even in the daily projects and tasks. If I am dropping my child off for care, I want to make sure that whatever I spend my time doing outside of being a mom is deeply worth it. Right now, success means being both a great mom and a strong professional, and deeply valuing that balance.
Creating Space to Be Fully Present at Work and at Home
What are the habits that allow you to reach your definition of success?
First, I need to be outside and active as much as I can for a quick reset. I find that my best work always happens when I step away from my computer and step away from the work itself. It doesn’t have to be a full vacation; it can just be a 30-minute walk without looking at emails.
I also find that to be truly present with my daughter, I have to intentionally turn my brain off so I can play on the ground, be silly, and just be there with her. That mental shift then allows me to go back into a work headspace refreshed and with new ideas. When I am running work through my head at all times, I become more task-oriented rather than idea- and strategy-oriented. Stepping away helps me reconnect with the bigger picture so that when I return to a project, I am more grounded in why we are doing something, rather than just how.
I also really believe in seasons. There are seasons, whether weeks or individual days, where your focus naturally shifts more to one area over another. In this current season of life, when I sit down at my computer, I maximize my time. I put a certain amount of pressure on myself because I know this is dedicated work time, and I need to get as much done as efficiently as possible.
My daughter goes to bed at six in the evening right now, so I will often shut my laptop down around four, spend two wonderful hours with her, have dinner with my husband, and then revisit and wrap up my work from eight to ten at night. It isn’t necessarily a long-term habit I want to keep forever, but right now, it allows me to be present in all areas of my life, which is what matters most to me.
The Relationships That Make Every Bold Step Possible
How has your community supported and been with you along your journey so far?
During the 10 years I spent in Oregon, I was a million miles away from the family and friends I grew up with. I truly believe that you are born with a family, you marry into a family, and you build a family. I built such an incredible community in Oregon. If I had ended up in the emergency room back then, my parents couldn’t have gotten there before my chosen family did. Because I was removed from my hometown resources, we really had to rely on each other.
The strength of a community is essential to keeping you grounded and human. Left to my own devices, my drive and ambition around work can easily wrap me up completely. Having reasons to step away, feel supported, have fun, and refresh my brain is so healthy.
That community was vital for that season of life. When I moved back here, we were surrounded by family again, which is incredible, but I realized something was missing. I didn’t have a local group of women who were striving for the same kind of balanced lifestyle I wanted. My Oregon community was built naturally through work, but here, I had to put in deliberate effort to build a network. I started meeting people for coffee, and if I met someone I connected with, I’d just say, “Hey, I don’t know many people here yet. Let’s get a drink and hang out.”
Because of that effort, I now have a strong group of women I can lean on. I can ask them for feedback on a job, ask for connections, or talk candidly about how to transition back to work as a mom of a three-month-old. Having people you can call who have walked the path before, or who know someone who has, and being able to be vulnerable with them is absolutely essential.
Why Letting Go of the Plan Opened the Right Doors
What does your dream life look like for you?
Before my current role, I was working in finance. This new opportunity presented itself when I wasn’t looking at all, but it arrived at the perfect time. I get to work with women I genuinely love and am inspired by, both my colleagues at the O’Connor Group and the women entrepreneurs I support every day. It also offered more flexibility, which I deeply appreciate, while still allowing me to build something fulfilling and use my brain in strategic ways.
At the moment, this is a dream scenario for me. I truly don’t think anything could be a better fit.
One of the biggest lessons I’ve had to embrace in my career is learning to let go. I am a planner by nature; I like to build out stages, set goals, and work backward step-by-step. But at several points in my life, I’ve had to release the need to have my entire career mapped out.
When I was in college athletics during my first career, I was hyper-focused on moving up into specific director roles. Then I transitioned into finance, assuming I would build a book of business and that would be the end-all-be-all. I’ve had to train myself to be comfortable with not knowing what the future holds, and to have blind faith that something amazing will come from taking a step.
Right now, I am absolutely living a dream scenario for this season of my life. It allows me to be present for my daughter, work with incredible women, do work I love, and still step away at four o’clock to play with her before jumping back online later. The autonomy I have is incredible.
It’s actually exciting that I don’t know exactly what comes next. If I have such an awesome situation right now, I know things will only get better going forward. That keeps me hopeful and excited about the future.
Having that blind faith also means taking opportunities where success isn’t guaranteed. I didn’t know for sure if I would succeed as a financial advisor, or if I could build a brand-new program from scratch at 23 years old. I don’t know with 100% certainty how every new venture will turn out, but believing that something great will come from it is a learned skill that I carry with me everywhere.
The Real Reason So Many People Never Take the Leap
Why do you think some women hesitate to take a leap of faith or do something big and bold?
I think people are deeply afraid of failure. It isn’t just women. It’s both women and men. I can think of several men who have immense capacity, but they are simply terrified to fail. Many people haven’t had that initial taste of success to build the foundational confidence that compounds over time.
There are also very real, practical factors that contribute to that fear: health insurance, financial security, and lifestyle requirements.
Furthermore, I don’t think everyone is always prepared for the sheer amount of hard work a leap of faith requires. Just because you take a leap and have blind faith that things will work out doesn’t mean it will be a walk in the park. Sometimes people are scared of hard work, scared of failure, and scared to ask for help.
Asking for help is one of the hardest things for people, especially in my line of work. I see so many women who want to offer resources or make introductions, yet the person needing help feels like asking for an introduction or a favor means they’ve already failed or couldn’t do it on their own. In reality, leveraging your community and the support around you is the greatest opportunity you have, because people genuinely want to help.
Purpose and Community Are the Foundation for Bold Decisions
What do women need to take on new opportunities?
Women need community, and they need to pursue work that fulfills them and gives them passion and purpose. I truly believe we can accomplish a great deal across many areas of our lives, but it has to stem from a place of purpose.
If being a full-time mom is what gives you purpose and passion, that is incredible. If being a dedicated working professional is your focus, that is incredible too. Finding that core passion is what propels us forward most effectively.
The other thing I always encourage women to remember is that you don’t have to do it all alone. People often feel like they have to carry everything by themselves, but you simply don’t.
Sometimes the Wrong Path Leads You Exactly Where You Belong
What is a hard lesson you’ve had to learn?
I’ve learned that not everything always works out, and that it is okay when it doesn’t.
In my previous finance role, it ultimately wasn’t the right season, the right place, or the right fit for me. But it was okay that it didn’t work out. At the time, I felt like a failure for not making it work. I questioned whether I should have done more due diligence before making the transition or evaluated the path more thoroughly.
However, I truly believe things happen for a reason. That role prepared me for future opportunities like the one I am in today. It is undeniably hard to be in a position where something isn’t working, feeling like a square peg in a round hole trying to force something that wasn’t meant to be. That was a tough season of feeling like, “What did I get myself into?”
If I hadn’t gone through that, I wouldn’t have gained the perspective I have now: sometimes you just have to recalculate, and that is completely okay.
Trust the Process Even When You Can’t See the Destination
If you could go back to a younger version of yourself, what advice would you give her?
I would tell her that it is okay not to have everything figured out.
The traditional working model I grew up seeing was that you get into a single role or company and stay there. That’s what my dad did as a personal attorney at one company for 30 years. When I was graduating from college, that was still the standard expectation for what a career should look like. I would encourage my younger self to stay open to unexpected opportunities and be creative about who to meet and what to learn.
I would also tell her to trust her gut and her instincts. When I was building that program at the university, I didn’t have entrepreneurial experience, and while I was under the umbrella of a big institution, I was essentially creating something out of nothing, which feels very parallel to building Shadow Her in many ways.
I would tell her to trust the building process. You are going to try some things that won’t work, and you are going to try other things that will be massive successes. When you have an entrepreneurial mindset and aren’t afraid to build and test ideas, it comes back to that blind faith. You have it in you to know what direction to head in.
Looking back now, I think, “Wow, I totally crushed that,” but at the moment, I didn’t feel that way. I would tell my younger self to trust that you can do it, you will do it, and to just keep putting one foot in front of the other.
About Callie Kaminskas
Callie Kaminskas is the Executive Director of Shadow Her, where she’s passionate about helping women entrepreneurs build stronger businesses through mentorship, education, and community. With a background spanning higher education, fundraising, financial services, and nonprofit leadership, she is fueled by connecting people, turning big ideas into action, and creating opportunities that help others succeed. As a mom, she treasures time with her family, prefers meaningful conversations over small talk, and believes a walk around the block, a trip to the beach or a weekend in the mountains can reset just about anything.
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