Toni Ann Careccio is the Chief Customer Officer and a Board Member at PortPro Technologies, Inc.

From the outside, it might look like progressing your career is a straight path forward. But this journey is rarely linear. My own experiences are proof of the winding road success can take you on.

Trucking is my family’s legacy. In the 1950s, my grandfather scraped together the little money he had to buy one truck. It was a small start, but he and my grandmother had the most incredible work ethic. They built their trucking company from the ground up.

My mom started working at the company when she was 15 years old. When I was a kid, she would bring me to work, making me run papers between various offices. Sometimes I’d huff and puff about it. But secretly, I admired the boss woman that my mom was at work.

Working in trucking is certainly impactful. The industry’s gross revenues contribute more than $940 billion to the American economy. But the industry is tough; it’s low margin, high risk and sometimes family drama can seep into the business. I heeded my mom’s advice and didn’t pursue a path in trucking—at first.

My Winding Path

Although I studied dance in college, I was a small fish in a big pond. So I picked a different road: Wall Street. I started with a six-month internship and was captivated by the trading desk. When a job opened up on the trading floor, I took it and ultimately worked my way up to vice president.

The glory eventually ended as I realized my passion had faded. Around the same time, my cousin proposed an idea to build an Uber for trucking. I quit my Wall Street job, and trucking edged its way back into my life in the form of Axel Technologies. But the company wasn’t a success, and we sold off our solution and customer base.

I then went to work for a venture capital firm but didn’t feel that I could thrive there. Eventually, my cousin and I reconnected, as his new trucking platform was achieving product/market fit. The company we run today, PortPro, provides software to trucking companies operating in and out of ports and railyards.

This was my full-circle return to trucking. It was a way to bring my mom and grandfather’s legacy into the future. I had new connections, varied expertise and was eager to work in trucking with a fresh perspective.

Three lessons from my journey

Like many people, my journey wasn’t straightforward. But this taught me key lessons about what it really takes to become successful, no matter how many pitstops your career path may take. Here are my top three:

1. Careers—and salaries—aren’t linear.

In my days on Wall Street, I was living the high life, making a generous salary. When I quit, I could sense disappointment and nervousness from my family, who had been so proud that I had rapidly climbed the ladder.

In hindsight, the distinct pieces of my career brought me to where I am now. The early days of going to work with my mom and seeing paper everywhere inspired PortPro, bringing tech and efficiency to trucking. Failing with Axle Technologies made me realize that the product had to be right for the industry. Working in VC showed me what matters to investors.

At times, my journey’s unexpected twists and turns felt like setbacks. In the moment, I was on a curvy road with an unclear direction. But looking back, I see how it all got me from point A to B today. If you’re feeling stuck in your career, try to embrace the twists and turns as a means of growth and new adventures, rather than barriers. The uncertainty I felt when I left my Wall Street job made me all the more ambitious to do something impactful. If you know you’re ready to make a career pivot, think about the skills and network you have and how those could transfer. Who do you know in your target industry? Do your leadership and communication skills work across sectors? Lean into what and who you know.

2. Failure can be the gateway to success.

When we launched Axle, we didn’t have experience yet and underestimated the lack of tech adoption in the trucking industry. If we hadn’t failed with Axle, I may not have worked in VC, which taught me so much about what makes a successful pitch. We may never have launched PortPro or been able to obtain over $12 million in funding—a huge success, considering that venture funding for logistics startups plummeted from $25.6 billion in 2021 to less than $3 billion last year.

It can be hard to dwell on your failure, but try to reframe it as a teachable moment. Be specific—was it the product itself, the marketing or just a busy time of year? That can help you pinpoint exact missteps and how to fix them for the future. For example, one of the problems with our previous company was that we didn’t have the right product-market fit and prematurely spoke with investors. Talk to your mentors and confidants. Chances are, they’ve failed at some point too, and have come back better and stronger from it.

3. Inspirational people matter most.

I was raised in an entrepreneurial family and saw the values of work ethic from the beginning. Being on the trading floor motivated me to climb the ladder. Working in VC inspired me to try again with PortPro. No matter the industry, being around hard-working people was the best thing I did for my career.

Think about qualities you admire in people, and seek them out at networking events, trade conferences, on LinkedIn or even as you’re recruiting and interviewing for a position at your company. You can teach and mentor them, but you also never stop learning and being mentored—even by people who may appear junior.

The path to success is often winding and unpredictable, filled with valuable lessons and unexpected opportunities. As you embark on your own professional journey, remember that each experience, whether triumph or setback, shapes your unique story.

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