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5 Lessons From Our CEO That Will Take Your Trucking Career to the Next Level

One of the most unique parts about Legacy is the fact that we are a family-owned company that operates all around the United States. 

We are one of the fastest-growing shipping companies in the midwest, and we’ve been expanding our services and locations for years. 

Our recent upgrade to a larger headquarters in Joliet is particularly noteworthy because this company started out of the back of our founder and CEO’s (Isaac Issa) semi-truck. We started in the back of a truck, and now we’re operating our HQ out of a massive truckyard and warehouse in Joliet, Illinois. 

Recently, we stole a few minutes out of Isaac’s busy day to talk about lessons that he’s learned from his experience in the trucking industry that spans more than a decade. 

Here are some of the biggest takeaways from that conversation. 

If you love what you do, it’s easier.

“At the time I was so young, I loved it. I always loved driving trucks, so to me – driving trucks – wasn’t a job…it was a lifestyle that I enjoyed.” – Isaac on his early days as a truck driver.

They say “if you love what you do, you’ll never work a day in your life”. The reality might be a little more complicated than this broad quote, but as Isaac said, if you love your job, you’ll be able to persist through the difficulties that it presents on a daily basis. 

Burnout is real. Fight it with balance.

“Burnout is very real in transportation, so if you plan on doing this for a long time, whether it’s behind the wheel or on the admin side. Burnout is extremely real and trying to find a balance between work,  family or even your own sanity, it’s very important to be successful in trucking.” – Isaac on his advice for newer truck drivers.

We’ve written countless times on this blog about the high turnover rate in the trucking industry, and our leadership knows that this is a very real problem. It’s important to work hard, but it’s even more important for drivers to have a balance in their lives. 

We want you to be a part of our team for a long time. Part of our mission at Legacy is to fight the turnover rate in trucking.

People can smell bad leaders.

In shipping, leadership is especially important because there are a lot of moving parts and a lot of people involved. 

Bad leadership is the difference between a shipment arriving on time and not arriving at all. 

This is Isaac’s leadership advice that he’s used in building a company that’s lasted more than a decade in a tough industry: 

“Be genuine. People can sniff out B.S. a mile away, treat your people good and they’ll treat the business good, right? That’s an old cliche, right? But it’s true. It’s so true. You treat your people good, and if you’re genuine, everything else will follow. Also, being the hardest working person in the room never failed me.”

The secret to success is simple.

In whatever you do in life, be it building a company, driving a semi-truck, or playing the violin, you need only a few things to succeed. 

For Isaac, it’s all about hard work, dedication and focus. If you put in the time and energy, you’ll see the results you’ve worked for. He puts it very well:

”Hard work, dedication and focus. It’s a simple recipe. Trucking is a business where as long as you are OK with and accept that you will be working hard. Excuse me – extremely hard – for a long duration of time, you’ll get to where you want to go. Again, it’s not an easy industry. Working hard for long duration of time scares people away – whether it’s in transportation or anything else. wworking hard is difficult. And usually, people only do it for a temporary period of time – a year or two years, months, whatever the case may be. There’s usually an expiration date behind it.  You need to forget the expiration date and focus on the goal.

Remember that your people are people – not just employees.

Legacy is a family-owned business and one of the most important parts of being family-owned is that we maintain a family-first mentality.

For us, treating our employees like family is the most important thing on our agenda. It’s our deepest truth. 

For Isaac, he doesn’t take this responsibility lightly. 

“It’s taking individuals within my organization and elevating them. The company is growing so quickly and our people are graduating through the company. Seeing the evolution of my people makes me extremely proud and working with them to continue that evolution, continuing that graduation to develop their careers.” – Isaac, on the most fulfilling part of his job.

Closing Thoughts

The growth that Legacy has seen in just the last few years is inspiring for any truck driver or entrepreneur. We’ve leveled up in our facilities and services all while maintaining a family-first mentality. 

This mentality is a top-down approach. All great things start with great leaders, and we’ve got a great leader here at Legacy that places tremendous value on his people. 

To get in touch with Isaac, check out his LinkedIn profile. To stay updated on all things Legacy Express Trucking, follow us on LinkedIn, Facebook, Instagram, and now, TikTok!

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