Michelle Penczak

CEO and Founder

Service Member's Branch - Marine Corps

Service Member's Status - Currently Serving - 15 years

What has been your military spouse career/entrepreneur journey so far?

My journey as a military spouse and entrepreneur has been a rollercoaster of challenges and triumphs. It all began when I lost my job while pregnant, prompting me to start my own business, Squared Away. The initial struggle turned into an opportunity to empower fellow military spouses by providing remote job opportunities. Over the years, we've grown exponentially, with 95 percent of our 400 employees being military spouses. Our focus on employee benefits like health insurance, mental health days, and paid maternity leave reflects our commitment to improving their lives. My unexpected path to becoming a CEO has been incredibly rewarding, and our mission is to continue supporting as many military spouses as possible on their career journeys.

Tell us about yourself.

I've been a military spouse for 11 years. I have two wonderful tiny tornadoes, aged 8 and 4. My passion for exploring new places and my love for books provide me with moments of solace and adventure amid the challenges of military life.

Tell us about a "typical" day in your professional life.

As a CEO, work-from-home mom, and military spouse, my day is a dynamic balancing act. It begins with coordinating kids' schedules and handling household responsibilities. I then dive into CEO duties, juggling meetings, strategy sessions, and decision-making. Flexibility is key as I navigate unexpected challenges while remaining focused on the company's growth. Being a military spouse adds a layer of adaptability to my professional life, requiring seamless transitions when duty calls. It's a demanding yet fulfilling day, embracing both my family and career with dedication and resilience.

If you've been stationed overseas, how did this affect your career and or business?

N/A

What has been your biggest military spouse career struggle and how did you overcome it?

My biggest military spouse career struggle was when I lost my job at Zirtual while three months pregnant. It was a devastating setback, especially since my husband and I had carefully planned for our family's future. However, I didn't let this challenge define me. Instead, I seized the opportunity to start my own company, Squared Away. I worked tirelessly to ensure a smooth transition for my clients, even as I was adjusting to motherhood and a significant time zone difference after my husband got orders to Hawaii. This journey tested my limits, but my determination to have something that was just mine and to support fellow military spouses ultimately prevailed.

What role did mentors and sponsors play in your journey?

None

How does your career path differ from what you imagined for yourself?

My career path has significantly diverged from what I initially imagined for myself. While I always knew I wanted to take care of people, I had initially assumed that meant pursuing a career as an attorney or a nurse. However, life had different plans for me. Losing my job while pregnant and subsequently founding Squared Away led me down a path I never anticipated. I became a CEO and an entrepreneur, championing the cause of military spouses by providing them with meaningful employment opportunities. Despite the unexpected twists and turns, I'm incredibly proud of the unique path I've carved out for myself and the impact I've had on others' lives.

How did military life (PCSing, deployments, trainings, etc) factor into your career decisions?

Military life, with its constant changes and challenges, played a significant role in shaping my career decisions. When I lost my job at Zirtual while three months pregnant, it highlighted the need for flexibility in my career due to frequent moves and unpredictable deployments. This experience prompted me to create Squared Away, a company that caters to military spouses facing similar obstacles by providing remote job opportunities. My own experiences with PCSing, time zone differences, and the difficulties faced by military spouses in finding employment directly influenced my decision to build a company that not only serves these individuals but also empowers them with essential benefits and support.

Have you ever had to geo-bach due to your career/entrepreneurship?

What resources have you found to be useful in your career/entrepreneur journey?

Throughout my career and entrepreneurial journey, I've discovered several invaluable resources that have been instrumental in my success. Firstly, professional peer groups have provided me with a network of like-minded individuals who understand the unique challenges of being a military spouse and entrepreneur. These groups have offered support, advice, and a sense of camaraderie that has been crucial.

Business resources for women have also played a pivotal role. Organizations and initiatives focused on empowering women in business have provided me with access to mentorship programs, funding opportunities, and educational resources, helping me navigate the entrepreneurial landscape effectively.

Perhaps most importantly, having a trusted group of supporters in my corner has been a cornerstone of my journey. Family, friends, and colleagues who believed in my vision and offered unwavering encouragement and assistance have been my pillars of strength. Their support has been immeasurable, and I couldn't have achieved what I have without them by my side.

Final word: what are your top tips for other military spouses about navigating a career within the military lifestyle?

For fellow military spouses, my key advice is to embrace your individual identity and not be afraid to pursue personal aspirations outside of being a spouse and parent. Seek remote and flexible career opportunities that accommodate the military lifestyle. Build a strong support network by connecting with other military spouses and consider entrepreneurship if traditional employment doesn't align with your needs. Continuously invest in skill development, stay resilient, and adapt to the unpredictability of military life. Seek mentorship and guidance to navigate your unique career journey. Your path is distinctive, so follow your passions and strive for fulfillment.

Listen to an interview with Michelle
to hear more about her story.

Tell Us YOUR Story