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Lady Trucker Trudy Jacobson Paved Her Own Road to Success

Trudy Jacobson came from humble beginnings and now is the Founder, Owner and Chairman of the Board of Jacobson Holdings Inc. Her hard work as a LADY TRUCKER and her success in the industry pave the way for potential career opportunities in trucking for women today.

Her new book that captures her life in a fictional novel titled “Diesel Smoke and Dangerous Curves” is in the making. Hear her journey in her own words.


1.Q.. As a businesswoman you had a unique job in the trucking business tell us how that came about.

I worked for a truck dealership in a small town in Missouri and learned my way around the industry and the people involved. One day I met a “trucker” who happened to have started a major trucking corporation called National Carriers. We were married and I was thrown into playing a key role in his business in Western Kansas. I felt blessed to have such an opportunity to prove that women have potential to be successful in a male dominated work environment and industry. The top leaders of the company were my husband and father-in-law, Executive VP and CEO, respectively, of the Fortune 200 publicly held meat processing, cattle feeding, and trucking operation. As leaders of the company they were respectful and intimidating at the same time. I was eager to learn and gain credibility in an industry in which I was interested and passionate about. I even went as far as becoming a driver, or “meat hauler” myself! I got my commercial driver’s license and began hauling meat from state to state. I loved every adventure on which I went, despite the dangers of the roads, because I felt empowered and could experience what my co-workers lived every day. My first trip took me from Kansas to New York, then to Michigan, Utah, Oregon, California, and back to Kansas again. The trip took two weeks. We broke down, I peed in a cup, and did not rest because we did whatever it took to deliver on time. It was a hustle, and it was common for meat to be stolen and truckers to be robbed along the way.

2.Q.What have been the biggest difficulties as a woman you encountered in this job?

The biggest difficulties I encountered as a female in the trucking industry began with becoming confident to make my voice heard in a room full of men. The common perception is that men handle “tough” jobs like driving, handling the equipment and responsibilities that come with management; but in reality, I was just as capable to do everything associated with trucking and more. 90% of all positions in trucking were occupied by men. I was a strong leader who trained drivers, and I had a passion to advocate for them. Getting product loads that weigh 40 tons from place to place takes a lot of determination and grit, and I was happy to be one of the ones hooking up the trailer and getting the job done. My main focus was to do a good job with John, my husband, as a co-driver. I had to back the trailer into docks and perform numerous difficult maneuvers. Even though I had earned the respect of my co-workers, I still ran into trouble when pulling into truck stops along the route. I was denied a bathroom in many locations, and most memorably in the southern states. I encountered discrimination in the 80’s as a female trucker, and thankfully that environment has changed for the better today.

3.Q There will be those who think that you are very lucky, so tell us also about the difficult times you have lived before your success.

Everyday I wake up and feel how lucky I am to have married a man who shared the same passion and drive that I have. We gave up so much of our time for work. Our relationship was based around work, and I even considered us to be workaholics. This led us to grow apart, because we did not make time for intimacy and closeness. We were constantly absorbed in work-related responsibilities. I often felt isolated in the small town in which our company was based. We worked through holidays and rarely spent personal time together. We hired amazing people of diverse backgrounds and held events such as safety banquets and business dinners with customers. We were social with people within the company and considered them family, as they often came over for barbeques and backyard fun. John and I stuck together because as big fish in a little pond, we were constantly under scrutiny, and much was expected of my husband and me. There was always much to be done, and I barely had any downtime. After the first company was sold, we started another trucking company from scratch near Kansas City, Missouri, TransAm Trucking Inc.. Starting a company requires full devotion and there was little room to pursue other passions that I had, including motherhood. Later my son was born, and I faced the dilemma of prioritizing my career and being a mother with the never-ending responsibilities of the new company. Most of the parenting responsibilities fell on my shoulders as my husband directed all his focus on the company. It was nothing short of an impossible feat!

4. Q. What would you consider as the most influential time in your life and career?

While isolated in the small town in Kansas and working at National Carriers, I took advantage of the amazing community in which I found myself. I took a leadership role and found fulfillment as an organizational leader and community influencer. I served as Chair of the County Economic Development Committee and was an officer on the Chamber of Commerce in the community. I was a representative of our company and was working in leadership positions in my early 20’s. I learned to adapt to a position of power and responsibility and consequently developed excellent leadership skills that I later applied to starting my own company. Being respected as a community leader trickled into all other aspects of my life and helped me become a skilled businesswoman. These leadership skills helped as well in my participation in philanthropic organizations in the Kansas City area as I became more involved in leadership roles. It was empowering to hold these positions and be well-respected within the community, and it was at this point I realized I was capable of anything. People looked to me for inspiration, and I exemplified strong leadership capabilities in executive careers that I have filled throughout my career.

5.Q. Being a woman in today's competitive job market can be a challenge not only do women face a wage gap, but also they have to compete with men. What is your advice to other women that want to get into Trucking? The question is how can a woman beat a man in the race for a job in the Trucking business. What opportunities are there?

Now is the time for women more than ever to “TRUCKER UP” and start their careers in trucking. In today’s competitive job market there are more ways than ever for women to get involved in the trucking industry, as drivers, managers, and executives. Women have more opportunities looking forward because there is a huge demand for workers. There is a nation-wide driver shortage and women now make up 8% of the driver workforce thanks to the efforts of organizations formed and movements in recent years encouraging women empowerment. Women excel in business as partners, communicators and their abilities to work with clients. There is now GPS, mobile communication, automatic transmission in equipment, better safety conditions and comfortable sleeper bunks. Equal pay is a good incentive to get into trucking as a woman because it is not biased. The driver pay is based on mileage, hours or percentage of the load. The trucking business has changed for the better in the last few decades, and women are crucial to the future of trucking and definitely all hold the potential to be management in top trucking companies.

6.Q.. What would a woman wear for a job interview in the trucking business?

Anybody applying for a job in trucking administration should wear a modest and practical business look. It is not critical to look professional in a traditional way. When interviewing for a driver’s position, an outfit consisting of jeans, a nice top, or jacket would be suitable. Wear clothes that look like you are not afraid to get dirty! Dressing for the job in “over-the-road” chic translates that “I can do any job a man can do.”

7.Q. How far were you willing to go to achieve your professional goals?

I learned the hardest physical parts of the job and worked from there into management at National Carriers. 10 years later, my husband and I started our new business, TransAm Trucking, as equal partners. We met with banks for lines of credit, hired a staff, and started putting together our team of drivers. We needed to create a strong customer base and really build the company from the ground up. We had a good reputation in the trucking business, as well as industry knowledge. I spent years getting to the position I hold now and dealt with a lot of challenging situations. It was hard work and I showed up for every day of it. And to top things off, I slept with the boss! LOL.

8.Q. What have you learned from your previous success?

Something that I have learned from previous success is that you must EARN a title and respect. Respect is not given, its only earned, and I learned this lesson in every step of my career. Leadership skills and company knowledge is power; but through everything, I know to always be humble and grateful.

9.Q. Women who have already made it to the top say that the only person who will help you there is yourself. Do you agree?

You need to be driven and push yourself, and along the way reach out to other women in the business world to create a network of empowerment and support. Even if guys outnumber you in the workplace, women can build each other up and create opportunities for others and it is critical to have a positive dynamic with other women for success. I have always found that I learn so much when I connect with women in my industry and feel as though I have a support network. I especially found this to be true when, in most recent years, I was Chair of Women’s Philanthropy of Jewish Federation. I found inspiration working with women to create and invoke success in others. It is a challenge to gain the respect of men in some situations, especially in trucking, and it was often discouraging. I pushed my way through tense work environments to find a seat at the table. Knowing that I had a network of women from my volunteer work to fall back on made me feel not completely alone. It was exhausting to feel as though I had to constantly prove myself in my field with the fear of judgement from men. I wanted to be respected for my skills and knowledge, not for my looks or connections. Through the support of women, I realized that I was a vibrant person with much to offer, and relationships with women brought out my best self and built my confidence to stay strong in anything I choose to do and anywhere I choose to do it. Female co-workers validate your feelings and thoughts, support each other, and it is crucial for women to work together to bring innovation in the business world.

10.Q. Tell us your sacrifices?

I sacrificed so much by devoting all my time to my career. I lost family time, bonding, leisure time and just taking the time to enjoy life. The company was my life and I was there day and night. Finally, I got involved in charity work and slowed down my lifestyle to spend more time with my son. I do not regret making my company a priority because it is very self-satisfying and my efforts were rewarding, and now that I have moved on from daily business responsibilities, my life has more time for moments that bring me happiness and for new opportunities to be explored.

11.Q. You're a Mother which is a very important job. What advice would you give other women working in a man's job that want to have children?

Think about what kind of parent you want to be and set goals. Can you spend time with your kid? Will you teach your kid? It is important to spend quality time with your children, especially in the developmental time of their lives. My advice is to make the decision that is best for you and your family, whatever that may be, and prepare for the ride!

12.Q. Where can we find you on social media?

I can be found on Instagram @trudyjacobsonta for my personal account and my business account is @trudyfriend_. My website is

13.Q. You recently moved from Kansas to NYC. Tell us about your NYC lifestyle.

I had the time of my life when I first moved to NYC! It felt like making up for lost time to live new experiences, despite negative publicity looking into my personal endeavors. My husband and I have no secrets, share everything and he continues to be my best supporter and friend. Today, we are closer than ever and happy living the lives we choose. I wanted an adventure solely for myself after devoting my time to others for most of my life. I was a hard-working business executive, loyal wife, mother, volunteer; and I felt empty at one point. I decided the city would entice me and I was drawn to New York City’s energy. I had been to NYC several times and wanted to try the fast-paced lifestyle after living in the Midwest for so long. I am now fortunate enough to wake up every morning and see a beautiful view of Central Park, and would not trade it for the world.

14. What’s the next chapter in your life?

Talk it up!

A book? Talent agency?

The next chapter of my life still involves being at the helm of our thriving companies, in addition to working with incredible people who believe in my voice and experience and are looking to create some new amazing magic with me. More details are TBD, but my partners and I are looking to open a talent management business, and my life story is being created into a fictional novel. The short summary of the book, titled Diesel Dust and Dangerous Curves, is: “A small town girl from Missouri goes on the journey of her life traveling the country and becoming a trucking icon after finding romance in the most unexpected way.” I cannot wait to see how these next adventures in my life unfold!


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