Power Women: Jessica Calzaretta on How to Successfully Navigate Work, Love, and Life as a Powerful Woman

Originally published in Authority Magazine

How does a successful, strong, and powerful woman navigate work, employee relationships, love, and life in a world that still feels uncomfortable with strong women? In this interview series, called “Power Women” we are talking to accomplished women leaders who share their stories and experiences navigating work, love and life as a powerful woman.

As a part of this series, I had the distinct pleasure of interviewing Jessica Calzaretta.

Jessica Calzaretta is vice president of Insight Global. A founder of Insight Global’s Women’s Leadership Council, she has been instrumental in earning the company a spot on Fortune’s Best Workplaces for Women list for three consecutive years. As a wife and mother, she is a passionate advocate for helping women find their personal and professional balance — or “their new 100%” as she has coined it.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your childhood “backstory”?

I grew up in Columbus, OH with two amazing parents (who are my role models) and my three younger sisters. I learned early that hard work is key to earning success, and while we certainly were comfortable, I was never given an allowance and was expected to have a full-time job beginning at 14 years old. My family grounds me and inspires me as I build and raise my own today.

Can you tell us the story about what led you to this particular career path?

I always knew I wanted to have a career somewhere that allowed me to be rewarded for my hard work. It needed to be an industry that had seemingly limitless opportunity. I always joke that I didn’t choose staffing, but instead, it chose me.

I started at Insight Global back in 2009 with a pretty surface-level understanding of the staffing industry. But I loved the business model and opportunity for growth. Fast forward 14 years and here I am, heading up the Insight Global Health practice with a true and deep knowledge of this special industry. What I love about Insight Global is its openness to taking a chance on people. In life, I certainly wasn’t the most accomplished student or athlete, but I knew that I could work hard because I had done that my whole life. Insight Global took a chance on me, hiring me as a recruiter and allowing me to grow throughout my career to get to where I am today. It is a company that grows when its people grow — that’s pretty magical.

Can you share the most interesting story that happened to you since you began your career?

They say that failure makes you who you are, and I couldn’t agree more. I’ll let you in on a secret. I failed ROYALLY at my career several years ago. In fact, I tried to quit at least five times. I was on a performance plan, and in hindsight, I deserved it. I wasn’t making the right choices, and I wasn’t delivering on my responsibilities, all of which stemmed from massive insecurities and trying to be everyone’s friend instead of the leader that my people needed. I will never forget my leader (now CEO) telling me that I had every ability to make the right changes, but only if I wanted to. That turned it all around for me. Failing is the reason I’m in the role I am today. Once I lived through that failure, I stopped fearing it.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

High character: No questions asked, you have to have high character to be successful, and even more so than that, to be a good person. I consider character table stakes to advancing as a leader.
Listening: I’ve learned so much through active listening. I listen intently and then try to emulate those things in a way that stays true to who I am. Being an intentional listener is a key part of being a successful and highly engaged leader.
Humble confidence: I am cheating with two traits in one here, and while humility and confidence don’t often go hand-in-hand, the combination is lethal. You must know your worth while acknowledging where you need to grow. You also can’t let those growth areas stand in your way. When I moved into my current role, I definitely wasn’t the obvious choice, but after hearing about the position and learning about the role’s ability to positively impact lives, I felt confident that I could do it, despite not having the perfect resume for the job. I knew I could, and those small moments of opportunity can create big rewards.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. The premise of this series assumes that our society still feels uncomfortable with strong women. Why do you think this is so?

The best — and strangest thing — is that I don’t think society really knows what to make of strong women. In fact, I think most people are puzzled by the notion of a strong, powerful woman.

Society also has an outdated notion of what is considered a strong female. Too often, society depicts a strong woman as either a really strong-willed, dedicated mother with a career in the home or as a really strong, alpha-type professional that doesn’t have the time or space to raise a family. To a degree, I think we, as women, are at fault for this notion. And unfortunately, it’s hard to find celebrated examples in this society of women that do both. I hope that in due time we can change this narrative. Strong doesn’t require perfection, and the strongest women in my mind are those that embrace their responsibilities and choices, however imperfect they may be.

Without saying any names, can you share a story from your own experience that illustrates this idea?

I will never forget my first exposure to Corporate America. I was working at a Fortune 20 company in its marketing group, which was led by an incredibly strong — and (at least to me) intimidating — female. She was my first example of what a kick-ass female with major responsibilities at home and professionally looked like. She was the breadwinner, a devoted mom of three, and a senior executive of a major Fortune-ranked enterprise. She was the type of woman who always charged first into a crowded elevator rather than waiting to be escorted in. I didn’t fully appreciate how groundbreaking she was. She stood up for herself and took charge in a time where, unfortunately, I think too many didn’t know or understand what to make of her. She eventually left to start her own business, something that now having launched our healthcare business, I especially admire. I learned so much from her and she opened my eyes to what was possible as a woman in business.

What should a powerful woman do in a context where she feels that people are uneasy around her?

NEVER apologize. Don’t apologize for bringing intensity to a conversation. And don’t apologize for being who you are.

What do we need to do as a society to change the unease around powerful women?

This one is simple: get with the times. It is such an outdated, yet widely still accepted norm, that powerful women shouldn’t exist. That’s like saying that AI doesn’t exist. And anyone who doesn’t realize this or accept this truth about AI is out of touch. It’s the same for powerful women. We talk about societal norms as if they are something that controls us — in actuality, we control it, and we can change the narrative.

In my own experience, I have observed that often women have to endure ridiculous or uncomfortable situations to achieve success that men don’t have to endure. Do you have a story like this from your own experience? Can you share it with us?

I had worked extremely hard for a promotion that I knew I deserved. I was told I did everything right and that I was more than qualified, but it just so happened that I was one of the few females in consideration for this level of promotion. At the time, there was an understanding (a horrible one!) that if you wanted to become a mother, you likely wouldn’t move up the corporate ladder. I found out I was six weeks pregnant the same week my President came into town to make his decision about my promotion. I wasn’t ready to share my news, and I also didn’t want to jeopardize my promotion. So, I went out on a Tuesday until 2am with my President and team and pretended to drink — (another understanding at the time was having to prove you could ‘hang’ if you wanted to advance). I did end up getting the promotion, but also ended up feeling angry and resentful. Here I was so excited about this new position and so excited about growing my family, but I couldn’t celebrate both. I am not sure a man will ever fully understand what that feels like.

I learned a very valuable lesson from this experience. Right or wrong, it is on us as women to prove what can be done, not only to ourselves but also to the outside world. If we want to change how society views powerful women, then we have to be the ones to change it. While that may seem like an unfair burden, I believe it is my responsibility to open doors for every female that comes after me.

In your opinion, what are the biggest challenges faced by women leaders that aren’t typically faced by their male counterparts?

Look, leaders face challenges every day, male or female. My experience might not be the same as others, but I feel grateful that the challenges I face as a business leader are not ones I face alone. While women leaders, me included, are often outnumbered by men, the support I feel from my male peers and leaders is not something I take for granted.

That said, there is an unfair standard out there that women “do it all.” We idolize women who have it together and say things like “wow, how does she do it all!?” I think this notion sets women up for failure. It’s not realistic to do it all, and trying to puts women on a fast track to burnout. I often get asked the question — how do you do it all? My answer: I don’t. I have a devoted spouse, an incredible nanny and family on speed dial to help when I need them. I make intentional choices to let certain things go — my kids aren’t perfectly dressed, my house isn’t always clean, I don’t always stick to my workout routine, and I say no to a lot of social events.

Let’s now shift our discussion to a slightly different direction. This is a question that nearly everyone with a job has to contend with. Was it difficult to fit your personal and family life into your business and career? For the benefit of our readers, can you articulate precisely what the struggle was?

I wish I had something profound to say here, but simply put, it’s hard. Really hard. No matter what, life is hard and will be coming at you from all angles, all the time. We have this imaginary idea that work/life balance is something to be achieved. The truth for me is that they are one in the same. My work is a part of my life just like my family is a part of my life. I work because it’s meaningful and fulfilling to me, just like tucking my kids into bed is meaningful and fulfilling to me. Both can be true at the same time.

What was a tipping point that helped you achieve a greater balance or greater equilibrium between your work life and personal life? What did you do to reach this equilibrium?

The biggest thing I’ve learned is that harboring guilt is the biggest hurdle to feeling content in both your work and personal life. So many of us carry guilt about what we’ve done — or haven’t done. In the last seven years between having children, uprooting my family and moving, and growing my career, I’ve learned to put guilt in its place. It doesn’t need to drain so much of my time and energy because it’s just a distraction from the energy I should be putting into the things that matter more.

Ok super. Here is the main question of our interview. Based on your opinion and experience, what are the “Five Things You Need To Thrive and Succeed as a Powerful Woman?” (Please share a story or example for each.)

  • Don’t apologize: I know I said this before, but never apologize for who you are or what you bring to the table. Be yourself, unapologetically, and the rest will follow suit.
  • Put guilt in its place: I know I’ve also mentioned this, but I really feel like guilt is a wasted emotion. Instead, channel your energy into the things that help you feel happy and powerful.
  • Stick to your values: It is easy today to be influenced, but never compromise your values. Your values are your north star and should guide every decision you make.
  • Listen, but filter: I learn a lot through listening, but I also have a strong filter. Everyone will have an opinion of what you should do and what is best for you. Listen and look to those you admire most to help you figure it out.
  • Free yourself from failure: Some people can let failure control them. Don’t let it get the best of you. Learn from your failures and move forward. Some of the best things in my life (including my job) came from epic failures.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

Sara Blakely is a total badass entrepreneur and philanthropist (not to mention, she lives here in Atlanta!). What she has built — from the ground up — and what she shares with the world is such a strong example of challenging societal norms. She is an open book, sharing the good stuff, the not so good stuff, and everything else along the way. I have a lot of respect for how she carries herself and how she has and continues to break barriers.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.