“No matter what happens, its your fault.” As a leader, you don’t get to make excuses. If something goes wrong inside of your company, ultimately the blame falls on you. When one of my team members or agents messes something up, I don’t get to play the blame game. I get to jump in and see how we can work together to fix it. Over the last 5 years, I have graciously received almost 3,500 referrals. It’s my name that people trust so when something goes wrong, I have to take responsibility and make it right.
Many successful people reinvented themselves in a later period in their life. Jeff Bezos worked in Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Croc was a milkshake-device salesman before starting the McDonalds franchise in his 50’s.
How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?
In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.
As a part of this interview series, I had the pleasure of interviewing Jessica Stroud.
Jessica Stroud is the Creator of The Lady CEO Initiative. Jessica Stroud’s mission in life is to help Ladies become the CEO of their lives. Jessica is a published author, speaker, and an accomplished business owner. Jessica is one of the top referred Insurance Agents in the Midwest. Jessica also teaches other business owners to create massive amounts of referrals just like she has.
Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?
I would love to tell you it’s something pretty incredible, but it’s not. I like to joke that I grew up on the corner of Welfare and Disfunction. The short version is two divorced parents with no money passing their children back and forth ever chance they go. I learned some hard life lessons early and I am grateful for every single one. When I tell people “If I can do it, you can do it!”, it’s no joke. I came from nothing. I became something. If I can do it, you can do it!
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
“You can’t go back and change the beginning. But you can start where you are and change the ending.” C.S. Lewis. This quote reminds me that I can’t change the past. Too often we want to think about and dwell on things that are out of our control. This beautiful quote reminds me that I can’t control or change what has already happened. But I can control and steer my future.
You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much? If you can, please share a story or example for each.
- I’m not like the other insurance agents or agency owners. When I first started in this next chapter of my life, I knew I had to be different. I knew I had to stand out because fitting in would mean I was going to disappear. I had to find ways to set myself apart from all the other thousands of insurance agents in my area. One of the ways I set myself apart is that I became an “attractive character” on social media. Most insurance agents talk about insurance all the time. I worked hard to make sure I talk about a variety of topics so people think about me for lots of different things, not just for insurance.
- I know that I am not for everyone so I don’t try to be. Finding a niche and going deep with them has been huge for my success. In the insurance world, agents and agency owners are encouraged to be everything to everyone. In my opinion, if you are talking to everyone, you really aren’t talking to anyone. Most insurance agents try to handle every single type of insurance a person or business might ever need. There are certain types of insurance we don’t offer in our agency because it doesn’t fit our niche.
- I am more concerned with helping my niche grow their business than I am with growing my business. Because I serve them at such a high level and help them get where they want to go, I grow and get where I want to go. From the very beginning of my insurance agency journey, I’ve studied how to grow businesses, not just insurance but all businesses. Then I took that knowledge and started sharing it with other business owners so I could help them grow.
Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?
Before the current Chapter I am in, I was in marketing and advertising which lead me into Pharmaceutical Sales. Both of those professions where heavy corporate type jobs that came with lots of reporting and spreadsheets.
And how did you “reinvent yourself” in your Second Chapter?
The first step was that I had to let the old me die before the new me could take over. I had to be honest with myself that my current career path no longer fit with my long term goals for my family. Like most new chapters, you have to bring some of the past with you. My biggest hurdle was that our family is a two-income household like most families. While I knew I was ready for another chapter, I couldn’t put my family at financial risk. I was very careful to continue with my current career while I built up my insurance business enough to replace my income. It’s romantic to hear people talk about how they burned all their bridges or just completely walked away. But that’s not reality for most people. You have to delicately balance both identities until the new one can be fully unleashed.
Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?
In my case, there wasn’t a specific incident or trigger that caused me to want to do a life changing shift into a new chapter. It was more of a slow nagging feeling. The experience of having corporate tell me what my goals and objective were just really started to grate on me. The little voice inside that kept whispering “You were made for more” just kept getting louder and louder until I couldn’t ignore it anymore.
What did you do to discover that you had a new skillset inside of you that you haven’t been maximizing?
I’ve always known I was a people person and a human chameleon. I’d had plenty of sales positions before where I had the privilege of working with many different personalities. It wasn’t until I was in pharmaceutical sales that I realized I had the gift of gentle persuasion. It never mattered what medication your company assigned you, it was your responsibility to figure out how it could benefit the doctors and their patients.
How did you find that and how did you ultimately overcome the barriers to help manifest those powers?
When I moved into selling insurance and working with other business owners, I found that a lot of them were scared to step out in ways that would help them build their business. Social media has been huge for me building my insurance agency. Now, I am able to use my powers of gentle persuasion to help other business owners through their fears and break through to generate massive amounts of referrals for their businesses.
How are things going with this new initiative? We would love to hear some specific examples or stories.
Often the scariest things we can do turn out to be the most rewarding things we can do. I am so happy I finally decided to move into the next chapter of my life. I was so nervous to leave my previous career behind and basically reinvent myself. Because I had the courage to listen to the little voice inside, my life has completely changed. I’m not going to say that being a business owner is all sunshine and rainbows, but every step has been worth it. I’m a better wife, a better mom, a better friend, and a better leader. I am available to make my family a priority, I have learned so much to help other business owners grow, and I provide opportunity for my team that other companies and jobs don’t provide. It was truly one of the best decisions I have ever made.
Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
Yes! The person who has made the biggest impact on my journey has been my friend and mentor Ryan Stewman. Ryan has been in my life for about four years. From the very beginning, he told me I need to figure out how to help OTHER business owners. He told me I needed to be different from all of the other insurance agents and focus on others instead of myself. While other insurance agency owners are focused on generating their own leads, Ryan had me focused on how I could generate leads for my fellow business owners. He flipped my thinking to be a mentality and mission of serving others so that my business would grow. Even after 5 years in business, Ryan still has me asking myself “How can I serve others in a bigger way?’
Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?
I still struggle with believing in myself. The day I think I am the best at everything is the day I know I have an issue. One of my main challenges is not recognizing and celebrating my wins. I can acknowledge that I have accomplished some amazing things but its hard to be proud of it because I know I can do so much more. Years ago, I stopped comparing myself to others. We never know the full story of other people’s successes so we shouldn’t compare their journey to ours. I track my progress based on what I know I am capable of accomplishing. I belong to an Elite Group of Business Owners called Apex Executives. It’s Ryan Stewman’s group. We often talk about how we move the goal post on ourselves. Every day we strive to get better. Which means every day I am capable of more. I hope I never catch up to the goal post of my potential.
In my own work I usually encourage my clients to ask for support before they embark on something new. How did you create your support system before you moved to your new chapter?
That’s a powerful question. When you move away from one chapter and into another, you have to leave behind certain members of your support system. That was definitely the case for me. I had to leave behind my pharmaceutical sales partners, but I knew it was for the best. I was able to use social media to put myself in the vicinity of other business owners that I could learn from and provide value to. I looked for other groups and events where I could surround myself and connect with other people trying to better their lives and businesses. Owning a business and being an entrepreneur can get lonely if you let it. I’m still constantly seeking out and connecting with others that I can learn from and serve.
Fantastic. Here is the main question of our interview. What are your “5 things I wish someone told me before I started leading my organization” and why? Please share a story or example for each.
- “No matter what happens, its your fault.” As a leader, you don’t get to make excuses. If something goes wrong inside of your company, ultimately the blame falls on you. When one of my team members or agents messes something up, I don’t get to play the blame game. I get to jump in and see how we can work together to fix it. Over the last 5 years, I have graciously received almost 3,500 referrals. It’s my name that people trust so when something goes wrong, I have to take responsibility and make it right.
- “If it’s your fault, you can fix it.” The good news about that is if something gets messed up in your organization, as the leader, you have the ability to fix it. Unfortunately, that might mean making a staff or system change that effects your team, but you have the ability to make those changes.
- “You won’t get it right the first time.” You probably won’t get it right the second or third time either. But there will be lessons along the way and eventually you will get it right. There are so many hard lessons that can only be learned by actually doing things. For every great idea I have that works out, there have been at least 5 or 6 different ideas or different approaches that didn’t work. Failing is not an option when you are committed to building something great. As long as you don’t quit, you will find a way.
- “You have to be bad at something before you can be good at something.” When I first started my company, I sucked at just about everything. I sucked at hiring, I sucked at customer service, I sucked at time management. When I first started leaning into social media, I sucked at that also. But the more I became committed to doing all of those things, the better I got. I won’t say I am incredible at doing any of them but I am way better than when I started. And I am way better than the person who never got started to begin with.
- “You will build your own prison brick by brick.” Most entrepreneurs don’t have the luxury of a fully staffed office or a big bank account in the beginning stages of their business. This means you are responsible for doing everything. Marketing and closing deals are just the beginning. Most of the time once you actually get the business is when the work begins. And as the business owner, all of it falls on you. Until you are bringing in so much business that you can’t physically keep up, you don’t get to make your first hire. There’s this extremely unpleasant part of growing a business where you just don’t think you can go on. But you can and you will. Feeling like you are in a prison that you built is actually a sign that you are ready to scale. That’s the best feeling in the world for a business owner!
You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?
If I could do something all day long and not have to worry about finances, I would tell people how amazing they are. I would speak love and light into so many people that their hearts would burst open. Very few people have someone in their lives that see how incredible they are and that tell them great things about themselves. I would be everyone’s cheerleader and encourage them every single day. I would follow them around and remind them that they are remarkable.
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. 🙂
I would love to have breakfast or lunch with Tom Brady. It wouldn’t have to be private. That would be a little weird for me since I am married. He could bring his lovely wife and I would bring my amazing husband. We could double date. Tom Brady is a perfect example of someone who doesn’t compare himself to others. At his level, there isn’t anyone for him to compare himself to. He studies his body and his own performance and is constantly looking for ways to improve. He also has a tremendous amount of haters. When you lead from the front and are the best in your class, people take shots at you and want to pull you down. Tom Brady continues to rise above and block out that noise to push himself. It’s incredible to watch. Love him or hate him, you know his name and you know he’s the best at what he does.
How can our readers further follow your work online?
Facebook — Jessica Stroud
Instagram — JessicaStroud_LadyCEO
Thank you so much for sharing these important insights. We wish you continued success and good health!