The How: Crafting A Career in Transportation

If you’ve both chosen and started a career in transportation, you’re already ahead. Why? In addition to simply surviving employment in 2020, choosing ones career trajectory and purpose, in of itself, is a notable accolade. As someone in their late 30s, I’ve spoken with many of my peers who continue to struggle to find a role where they are both fulfilled and feel like they’re making a real-world impact. As I mentioned in a previous post, if you’re working in transportation, it’s likely your work is having an impact on the world, and everyday people, if even in a small way. Yet in any journey, setting the right course is an important step, but equally important is the preparation for the journey itself. 

In this post, I’ll share some career observations that have been true for me. However, encourage you to challenge these assumptions as they may not fit you or your situation. 

Truth 1: The “perfect job” doesn’t exist     

This statement isn’t designed to discourage one to chase their dreams. It’s incredibly important to invest time to understand yourself, what motivates you, and think critically about roles that provide fulfillment. But when I hear the phrase “perfect job”, it characterizes the impossible, a job as a monolithic state of “perfect” when in fact, jobs are hardly the same everyday. Jobs, like their human executors, are dynamic. It’s highly unlikely in transportation you will be doing the same thing day in and out. In a field like urban transportation, by default, you work within a patchwork of other stakeholders who must all roughly align to make a thing happen. Further, many of us work on a project to project basis, which in themselves are dynamic in how they may fulfill us, or cause us constant consternation. 

This translates into certain conversations, meetings, days, or projects that are far better than others. As a result, the expectation of a “perfect job” isn’t fair to you or the job. However, more experience helps you better understand what jobs create more “perfect” days, where your job needs and your character are a match. From my own experiences, I found as a consultant, I gravitated towards external, client facing opportunities. Unfortunately, that was only about 20–30% of my job. When I moved to my next job, it allowed me to make that 70%-80% of my job. I even recalled periods of the job that felt “perfect”, but was fully aware those moments would come and go. On the flipside, “awful” jobs also have immense value, as they clearly demonstrate what type of work you want to avoid moving forward in your career.

Second, the idea of a “perfect job” distracts us from being present, if we are always fixated on what's next. While we all seek to grow professionally and advance, it’s a disservice to ourselves and others to discard the learning, and the impact of each occupation along the way. I think this is especially true in transportation, which is infinitely multi-faceted. I’ve had the opportunity to experience different levels of government (state, regional, local) and even different professional disciplines (sales, marketing) and found these somewhat fragmented experiences have been incredibly useful in trying to solve transportation problems. 

A final thought on the illusion of  “perfect job” is how it may cloud opportunities that arise. Katharine Kellemann, CEO of Pittsburgh’s Port Authority told me once that your “career is not a straight line, but a plinko board.” If you’re invested and have done well in your role, the experiences and the people you meet at that job will ultimately affect your next. If you’re not incorporating those experiences, its time wasted. Similarly, one’s professional life has the opportunity to be several discrete careers, not a simple solitary path. Every job should shape or contribute towards the next, but does not need to define it. 

Truth 2: The industry is a small town, and the perils and promises are similar. 

I grew up in a town where everyone knew everyone. This was great when there was a problem to fix, as we knew just who to fix it. On the flipside, it was terrible when you got in trouble, because everybody seemed to know instantly. Working in the transportation industry can be a small town. It has a strong sense of community and purpose. It also can unfortunately be a place where poor decisions are remembered for a long time. When I say poor decisions, I’m not describing technical choices, but character choices. 

Transportation is a messy problem. Many things need to go right to influence broad change, and as I mentioned in my last post, transportation challenges pose just as many emotional challenges as technical ones. It goes without saying that transportation professionals should be professional and ethical. But also recognize that your professional peers today will likely still be your professional colleagues for years. As emotional creatures, someone may not remember exactly what you said, or what technical decision was made. They will remember how you treated them, if you were honest, and if you kept your word. 

Influencing changes doesn’t just happen amongst your peers, it happens in community. There are extensive resources on better ways to engage with a community as it relates to transportation. However, it starts with listening. A “transportation expert” is only as effective as her ability to translate that wisdom into local action. Local action can only take place if there is trust. As the saying goes, “people don’t care how much you know, until they know how much you care.” 

Truth 3: As cities change, be prepared to change.

We’ve seen urban transportation change more in the past five years as compared to the past fifty. This means that problems are changing and as professionals, we too have to learn to be dynamic and adapt. Personally, I’ve always strived to be a generalist, and rejected the notion that I needed to specialize to succeed. Maintaining this curiosity, and being open to learn about all aspects of the industry may not lend itself to being the world-renown expert on X (which itself may be fleeting), but it prevents you from being placed in a box, and more importantly, enables you to quickly adapt as new challenges and opportunities reveal themselves.  

While I suggest being a generalist is a winning strategy, there are certain skills that you’ll be able to carry from job to job, and an early investment is worthwhile. Communication skills are mandatory. If you are working in urban transportation, you are in the business of helping people manage change and describing future, potentially intangible concepts. Change is scary, and being able to effectively listen and communicate ideas is an irreplaceable skill. Another critical skill is empathy. When working with colleagues or members of the community, a transportation issue may scratch the surface of far deeper issues. As practitioners, we’re sometimes eager to jump towards a solution, but we can’t help a community if we don’t understand the problem, and sometimes the history of its creation.  

If this post has been helpful, I encourage you to check out a few similar posts including early advice for young professionals, and a transportation planner’s guide for start-ups. Also, please share any “truths” that you’ve experienced across your career!

Next up: The Where: Where to look if you're considering pivoting into transportation as a career.