Trudy Jacobson Chats About Her Personal and Professional Life

trudy jacobson

Trudy sits down with a member of her team at the Jacobson Talent Press to chat about whatever comes to mind so her readers can learn who the real Trudy is.

Welcome to the first article of our Trudy Jacobson Chats series.
In this series, we at Jacobson Talent Press sit down with Trudy to talk about whatever is on her mind; entrepreneurship, life challenges, faith, tips for success… you name it. We want to give you a direct look into who Trudy really is, what she’s about and what drives her.
By learning more about her, her background, and her philosophy, you’ll also learn about yourself and what it takes to accomplish your own goals and live out your dreams as well. You are capable of achieving everything you want; Trudy just wants to bring that out of you.
Our Interview Article
In this article we talk about her rise from a quiet, small town midwestern girl to successful business owner, entrepreneur, and Manhattan socialite.
It wasn’t an easy path. In fact, it was her trials and tribulations that forged who she became. As a young, quiet, and shy woman, Trudy made the decision that she needed to break out of her routine and take life head on. So, she jumped right in the arena and grabbed the bull by the horns and went to work – in a clerical position.
We at Jacobson Talent Press (JTP) sat down and talked about her wild ride and what it was like to go from a simple trucking company clerical worker to a world-class entrepreneur and CEO of a Fortune 200 company.


JTP: So how did you end up in the trucking industry?
Trudy: I came by it naturally because my husband was in a family business. It was, and still is a predominantly male industry. There were very few women at the time accepting clerical positions.
I was a young bride, and the issue was I married a workaholic. I could have either developed my own career or be a part of the family business and have that in common with my husband. Part of the decision was that I could spend more time with him.
JTP: Once you entered the trucking industry, what did you learn? Was there anything surprising about it?
Trudy: I loved it. Frankly, I loved working with men because I had a keen ability to understand the difference between men and women and their egos, and the value of me being a female.
I enjoyed it immensely and I loved working with truck drivers, and I loved being with the people who did all the work to make us successful. I was surprised at how much I loved it.
Another thing that surprised me about it was it was like getting a master’s degree in business. While I was sitting at the table for lunch with company leaders – for lunch – not for the meetings, and I sat quiet, listening to them. I grasped all that I could, I learned how a successful business worked together and what’s necessary in the organization. I absorbed it so well I became like a sponge.
JTP: The trucking industry is male dominated. Did you run into any resistance or discrimination?
Trudy: Yes. When I started in the industry, there were no laws to protect women from sexual harassment. Every other minute there was some off-color joke, and that was their energy that was spent. It was a high anxiety environment.
JTP: How did you overcome it?
Trudy: I just laughed when it was appropriate, or didn’t pay attention to it because frankly, it got boring, they weren’t funny anymore. To me… it wasn’t that offensive to me individually. Was it disrespectful? Of course. Was it objectifying women? Of course. I just looked past that, no one ever treated me with disrespect.

trudy jacobson

Jumping in Head First

JTP: At some point, you decided to become a trucker to learn more about the industry. That was a major decision. Can you tell us more about that?
Trudy: I wanted to be respected as a capable person. I wanted to be respected by the drivers who I was training. And I wanted to be respected on a linear basis as being a potential executive. I wanted to empathize and understand the drivers and their lives and what they did – that was the key to success in our business.
JTP: You have proven to be a success both at working at the family business and later building your own thriving business. What advice would you give the young generation of female entrepreneurs?
Trudy: Rely on relationships more than technology when you’re doing business with others. Nothing surpasses the personalization of looking someone in the eyes and creating a bond.
JTP: As an entrepreneur and business owner, you understand the value and importance of leadership. What can you tell entrepreneurs about leadership?
Trudy: You can be the best inspiration. My experience has been, if you earn respect from your people, that’s half the battle. Inspiration is another component, being able to inspire others is great.
Another is being real. Avoid talking about something you really don’t understand. And it’s the idea of bringing value to what you do with leadership – to work, to yourself, to others, it’s that value quality.
All the things that go into making you valuable to yourself, to others, to the community. You are a role model and that’s the best way of teaching it, is by doing it.

End of Interview

Trudy’s experience taught her a lot about life, business, and womanhood. From a small-town girl to an influential businesswoman enjoying the fruits of her labor, she brings a lot of life’s lessons, proven leadership, and inspirational words to the next generation of women.
Trudy earned everything she has today and worked hard for it. Furthermore, she also understands that women everywhere can achieve things well beyond what they believe is possible.
Her goal is to help them understand it and, more importantly, believe it.
We will sit down with her regularly in our Trudy Jacobson Chats series to discuss whatever else that will bring value and hope to women everywhere.
That’s why Trudy wants nothing more than to empower, encourage and inspire women to break down their barriers and build something special. And it all starts here with Trudy Jacobson.

Follow Trudy on Instagram to stay in touch.