We recently connected with Jill Olish and have shared our conversation below.

Jill, appreciate you joining us today. Along with taking care of clients, taking care of our team is one of the most important things we can do as leaders. Looking back on your journey, did you have a boss that was really great? Maybe you can tell us about that boss and what made them a wonderful person to work for?

I have considered myself a leader for a long time but didn’t know the kind of impact I might have as an entrepreneur and how much the kind of leader I become will influence that impact. When I decided to start my entrepreneurial adventure, I managed to land myself a client for my virtual assistant business right away. I love this part of our story because I really thought this woman was just a little odd. When I applied I was thrown off and actually a little nervous with her email starting off with “princess.” We connected right away and I made it into her hiring process. It took two years on her team to understand the kind of leader she is. I believe that a great leader can see the bigger picture for others. Without even asking her, she did become my mentor. Leading by example and with many ulterior motives along the way, she has helped me not just grow as a human and get more clear about my business, but also become a better leader. As a visionary she not only has shared her intuition about me, but for many others in our community. She has the others that she cares for at the forefront of her mind and is fierce about them. Her leadership and selflessness are admirable. She has taught me the importance of not only highlighting others but actually getting excited about their things that I might not even be a part of. As a first time mom, entrepreneur, and author, in my mid-thirties, I am living my dream life now because of her leadership and guidance. I am practicing being living proof and living my leadership out loud, to show what is possible and that anyone can have a business that they own and doesn’t own them.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I am an inspiring first time mom and entrepreneur. I became a mom and entrepreneur at the same time in the middle of the COVID-19 Pandemic. My values shifted when I became a mom and my contribution in supporting my family followed that shift. I researched virtual positions for work and decided to invest in myself and become a Virtual Assistant. This allowed for me to stay home and take care of our new baby and still contribute financially. Being home also allowed me to start working on healing my Postpartum Anxiety and Depression.

I am surviving Postpartum Anxiety, Depression and Rage and creating a life and business that is fulfilling and meaningful while being living proof for all moms, that living out your dream life is possible. The clients that I have worked with while a Virtual Assistant have influenced me in doing this. I’ve learned how to get clear on what I wanted for my family and how to make it happen, how to be a better leader, and how I can help more moms.

I founded Mama Outspoken to help moms find their voices and be heard, advocate for themselves, and spread awareness for motherhood transitions. I didn’t know just how hard that becoming a mom and a new family would be during a world wide pandemic. I had people in my life who were already helping moms and new families through Perinatal Mood and Anxiety Disorders and was asked to share my experience. In doing so, the calling to help others speak up about what they have gone through in their motherhood transitions started to show. In going to support groups I realized just how many new and seasoned moms keep so much internalized. I wanted to encourage other moms to be outspoken about how their transitions were going. But in order to ask other moms to be outspoken I needed to be outspoken first, so I try to be living proof of a life where there is healing and having a business that doesn’t own me.

Currently, I have a weekly segment on the live stream Good Morning Entrepreneurs where I get to share about being a Mama Entrepreneur and what I’m learning along the way. I am the co-host of the Mucked Up My Self Care Podcast- unfiltered, real conversations from two global moms, and the Mama Outspoken Podcast. These podcasts have been therapeutic in their own ways in talking about the struggles of self care as a mom and entrepreneur and navigating parenthood. I am also the author of Mama Outspoken. My book has been a crucial part of my business and getting clear on my values. I share my story of healing through a pandemic pregnancy, birth trauma, postpartum anxiety, depression and rage.

How about pivoting – can you share the story of a time you’ve had to pivot?

When I had my first child in the middle of the COVID-19 Pandemic my values shifted. I was working for NY State at the time and had to consider if going back would be a good option. I had the hopes of a promotion if I were to go back, but that meant putting my three month old child in day care and working potentially 10 hour shifts. My husband and I spent a lot of time figuring out the pros and cons of that and we agreed that it wasn’t aligned with our values. I was also a licensed funeral director and we considered if going back into that industry might be an option. Unfortunately, my past experiences were keeping us from choosing that path again.

I researched virtual positions for work and decided to invest in myself and become a Virtual Assistant. This allowed for me to stay home and take care of our new baby and still contribute financially. Starting a business for myself was a completely different ball game compared to the corporate jobs I had worked in the past. And especially having an infant made it even more challenging. One of the benefits of being a business owner was setting my own hours, but in reality, my child set my hours.

Not only did I have a shift in careers, but I had a shift in how I spent my time and what my priorities were. I was overwhelmed with the ‘need’ to work in the first few months that I started my business, but quickly faced burnout. One of my clients helped me to put my priorities in check and change my lifestyle so that my business would not own me but I would own it. Since these shifts I have seen greater change in me as a business owner, having the time to work on and in my business. I’ve seen growth in me as a leader, mother and human. And there has been greater momentum in getting the things I want in life – reaching milestones and achieving goals, both in business and life.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

I think the biggest thing I’ve had to unlearn is that it’s not personal.

As a team member for a client of mine, I am involved in many projects that we do for her business. When I was fresh on the team I had the task to learn a new website builder/host and move the website to it. I took a lot of pride in the work I had done on getting it there, but it really was just copy and paste. We continued to add to it and up-leveling the content. The more that I contributed to the website the more I felt good about it.

Over time we would get feedback and make some changes here and there. But eventually, we needed to make big changes, and I took offense that many of the things I did were what needed to change. It took a while to learn to not take offense to my work being changed. The need for change is bigger than me and my pride – obviously, feedback showed that it wasn’t working. What was the silliest thing was that I was so new that I didn’t know what really needed to be on that website anyway. My ego got the best of me and being on a team, there’s really no room for that.

Contact Info:

• Website: https://www.mamaoutspoken.com
• Instagram: https://www.instagram.com/mamaoutspoken
• Facebook: https://www.facebook.com/mamaoutspoken
• Linkedin: https://www.linkedin.com/in/jill-ann-olish-59592a1b6/
• Youtube: https://www.youtube.com/@JillOlish/featured

Image Credits

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