10 Careers For Aspiring City Planners

I’m a professional transportation planner, and have been for nearly 15 years, but these generally apply to most planning pathways.1 I’ll note where I don’t know enough and had to reach out to a friend, and if there’s anything particular about the pathway. I’ll also muse on a potential fun pathway from one pathway to another. I think that’s fun. Let me know what you think below.

1. Traditional Public Sector Planner

This one will look familiar to lots of my colleagues. You can start, continue, or end your career in public service. This can manifest in many different roles, both individual contributor and management, and can exist at all levels of government: from hyperlocal (block-level) to Federal. This type of role is ubiquitous and often essential to swan-dive into and/or out of at various points during a life: here, you’re part of the client team and see projects through, unlike some of the other paths below, whose roles often interact tangentially with projects or plans.

A pathway here could include seeking professional certification as a member of the American Institute of Certified Planners (AICP) or other organization (TDM from the Association of Commuter Transit, Professional Planner for New Jersey planners, etc.).

Potential pathway: School (undergrad or graduate) → “Planner I” → “Planner II” → Consulting → Director / Leadership (either in consulting or public sector work)

2. Civil or Traffic Engineer…or Literally Driving Trains or Buses

Traditionally, a transportation “engineer” was an operator. Think a conductor on an olde-timey train. This job certainly still exists, and it’s a good union job, whether driving a train or a bus, or doing support work for either or both at a transit agency. A word to the wise here: even if you decide to go the other route, designing our systems, it’s good practice to seek out operators and drivers to understand their perspective and to make friends with people from different backgrounds. Don’t ever be a snob. You’re not better than anyone because you make more money or have more time in school. In fact, because these jobs are union, you can make a great living as a skilled and tenured operator.

A pathway here likely includes studying for and passing the Professional Engineer exams that allow you to “stamp” drawings that are used for construction. These take time and require both experience and judgement that only come with time. It’s not a short path.

Potential pathway: School → Grad School → Public Sector Designer / Private Sector Designer → Engineer-in-Training (EIT) → Professional Engineer → Leadership / Contribution Mastery

Potential pathway: School → Good Union Job → Leadership → Good Union Job → Union Leadership?

3. Policy Analyst or Government Affairs

The next pathway is less design or traditional planning, but more helping to write and influence the rules that make planning and engineering work. This pathway often runs parallel to traditional “planning,” with many policy-oriented folks earning public administration degrees instead of, or alongside, urban studies papers. Jobs here are also public or private: many offices inside the Executive Branch of many mayors’ (or equivalent) or governors’ offices hire policy hands to write or edit governing documents. Alternatively, many private firms exist to support this development; these particular shops leverage resources so the private sector can do more. These shops also work, in certain circumstances, to help advocates or think tanks develop solutions to problems they have developed on their own or with partners. Just a word to the wise: know what it is you’re getting yourself into politically.

Potential pathway: School → Grad School → Executive Branch (public sector) OR Policy Shop/Think Tank (prviate/nonprofit) → Elected Official or Staffer (legislative branch) → Leadership (public/private/non-profit)

4. Elected Official or Staffer

This one is narrower by nature. There are fewer elected officials than there are roles supporting them, and running for and holding office is a completely insane skill set that if you’re interested in, you can just…do. We need more “urbanists”2 and planners and engineers in elected office with power to make better decisions about spending and prioritization for built environment solutions. So if this appeals to you, it’s a great opportunity to think about building relationships early and learning as much as you can about your place. This path does require tenure or at least immunity from carpetbagging allegations.

Potential pathway: Literally anything → Get Elected

You can also work with electeds. This is similar to government affairs, but you work for the legislative branch, so your daily tools will be oriented toward lobbyists. The main difference is the essence of the job: working for the executive (DOT, Planning, Environmental, Housing, Finance, etc.) means working to implement or administer, while working for the legislative branch means you’re interested in changing the rules that we all (supposedly play by).

Potential pathway: School → Work a little to get some experience → Volunteer on a campaign (likely door-knocking at first, unless you already have some experience here; it’s relatively easy to move up with some dedication) → If your candidate wins, there may be a job for you at the end of the line.

5. Advocate, Activist, Organizer

Who are these people that attempt to influence lawmakers or lawdoers? Advocates, activists, and organizers. They all do so in slightly different ways:

• Advocates work for organizations that fight for more general theories of change. They gather constituents around specific ideas and prove that there’s power in good ideas and big numbers. They’ll fight for causes like safe streets, affordable housing, better schools, safer environments, and so on. If there’s an injustice somewhere that donor(s) are willing to fund, there’s likely a nonprofit advocacy organization ready to go fight for it. These guys are the white hats and as close to pure good-doing as you can do in our field.3

Potential pathway: School (or not?) → Some level of domain expertise OR Deep nnthusiasm and a track record that demonstrates willingness to learn → Volunteer or Apply for entry-level jobs → Work experience → Public sector planner or policy analyst OR Staffer OR Elected.

• Activists are the strong version of advocates. They’re often more radical and more public-facing and focus more narrowly on a particular project they do or don’t like and are willing to get arrested for the cause. (Sometimes. I do NOT advocate or suggest that you get arrested or do any crimes or crime-adjacent things.) Activists play a particular role in the stakeholder power map, and even if you don’t feel passionately about one particular topic enough to lay your reputation at a minimum out, you should continue to be aware that these people exist and will either be your greatest help or your biggest pain in the ass.

Potential pathway: REDACTED.

• Closely related to the above jobs are organizers. These folks are the people-oriented staff inside organizations. They could work at any of the above jobs. Sometimes these workers are called community engagement specialists and have a particular set of skills geared toward the presentation of information and the receipt of related feedback. This process will make a project better if done right and will make a project worse if done wrong. The best engagement specialists/organizers are people with a deep empathy, domain expertise, and endless patience.

Potential pathway: School → Life → Demonstrating extreme levels of patience → Flowing in and out of different career pathways depending on the need to organize and fix misinformation.

6. Academic / Researcher

The purest career path on this list. You go to school, then you go to school some more, then you keep going to school, then you take a few tests, and then you go to school more, but this time there’s school to take the place of school. The challenge with the academic route is that it’s not easier than a non-academic path. Finding the program that fits your needs and style also has the right staff to support you and funding to help make you not die of scurvy. Then you have to find a job, which is extremely niche and scarce. You have to at least tolerate teaching, and you are often forced to publish to earn tenure. But once you get tenure, you can sort of …do whatever. As long as the program still exists and the world still needs academics to baseline practical application, these jobs will continue to exist. Godspeed.

Potential pathway: School → School → School → School → Advisory? → School → Retirement.

7. Transit / AV Tech Development or Sales

This is a relatively new field: there’s tech in planning, too. These companies often provide support to the public sector or compete directly if the public sector isn’t providing what the market has demanded.4 There’s certainly room for tech in planning. I see it as multiplying the impact of existing resources and keeping people who otherwise would go do tech elsewhere tethered to fighting for accessible streets and Good transit. There are lots of roles within these companies that align with the above career paths, but there’s also something here that’s different: sales. In public sector work, “sales” is just convincing the elected officials to spend OUR money on projects. In the private sector, especially in the tech world, sales is convincing elected officials to spend YOUR money on projects.

Potential pathway: School → Tech → Go work at the public agency you serviced while at tech → Consulting / Back to tech.

8. Traditional / Management Consultant

This is the place where you can make the most money if you want to work a lot of billable hours. I currently do this kind of work, and I enjoy it because I like the creative pursuit of projects and diversity of clients. I enjoy being able to get in and out of teams to work on pieces of a larger development. I like that I can be relatively mode-agnostic and work on pedestrian/bike projects, transit projects, road projects, etc. This works for my entrepreneurial brain and motivations. I like that I can work internationally and domestically and learn every day from people who’ve done this work for decades. I recommend every planner take a stop at a consulting firm at some point, if for nothing else than to earn perspective, which is always helpful.

Potential pathway: School → Grad School → Entry-level public sector or consulting → The other one → Leadership, hopefully.

9. Professional Critic or Content Creator

This is a relatively new role, and it grew with the rise in social media. It’s a new way to communicate and, honestly, doesn’t take any credentials at all, and can bring ideas to new audiences often out of reach from traditional media outlets. These people write for essay outlets and can support themselves through multiple projects, and the most successful ones can fully support themselves through the social media environments. That number is vanishingly small, and often these creators make little to no income from content creation alone, so this path, while requiring the least up-front investment, also has the lowest ceiling for success. If you do decide to create content for a living, you might want to find a secondary or tertiary source while you do this.

Potential pathway: A pen, a pad, a phone, a dream, a secondary job → ??? → Profit

10. Land or Property Developer

This last one is less transportation-related but still tangential: in a sane world, dense transit accompanies dense housing and mixed-use development. So you can become a property or real estate developer to work on TOD (Transit-Oriented Development) or otherwise new housing that we desperately need—everywhere. If you’re just starting your journey and transportation isn’t for you, then I really do suggest you learn Excel and surveying and get to building. You can work in non-profit development or for-profit development (we need all housing) and can work on building affordable housing, missing middle housing, or luxury development (I repeat, we need all housing for reasons you learn in grad school).

Potential profit: School → Grad school → Public sector planner / Development firm / Urban Designer → Developer.

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1. 80% of the battle is showing up.

How does anyone meet anyone? Whether you’re new to any field (I’m specifically going to talk about planning) or you’re a seasoned professional, you won’t meet people to build your “network” if you’re not in the rooms. Part of the problem is access and availability. How should you know what room to be in if you’ve never been in one? How can you find out about happy hours, lectures, events, conferences, meetups, and activities if you’re very new to the field? Practically a few starter tasks:

• Find your local chapter of a professional organization. If you’re younger, find the “Young Professionals of xxxxx”. But there are a ton of organizations in every city or region that help to organize our profession: the American Planning Association has a local and national chapter in most places in the US, the Institute of Transportation Engineers unironically loves when planners join, and the Women’s Transportation Seminar is a good place to start. Membership can be nominal and each organization likely also hosts free events sporadically.

• Separately, so it doesn’t get lost: there are local groups that also have lots of great influence and organizing power. These groups may be hyperlocal down to the block level, but they might also be more niche depending on your particular interest, and they may be political. You may be able to do meaningful work right away that helps you develop a reputation. Often, you can find out about these groups from the larger umbrella ones mentioned above.

• Individual outreach might be a good path. It’s OK to cold email someone whose career path interests you, who works at a place that might be hiring, or someone who you’ve seen talk and you’d like to follow up with. Warning: do not ask for anything right up front except perhaps to buy them a cup of coffee where’s most convenient for them. This person does not know you, and you shouldn’t develop a parasocial relationship with them. Most people will agree to a quick cuppa somewhere, and, honestly, it’s a red flag for someone to say no for any other reason than they might be busy. Their time is not intrinsically more valuable than yours, and it speaks directly to their character. I really do believe in karma in this instance.

Takeaway: Be confident, be in the rooms, and be willing to sacrifice quiet time for this endeavor.

2. Be interesting and interested. (Thanks, Dave)

It’s really hard to know what it means to “be interesting,” and there’s no one way to do it. Here’s where lots of people—interesting and not—falter in their quest to connect with strangers: being yourself is enough, but there is a way to prepare for situations like this. If you’re involved in any hobby or have any interests whatsoever, you can learn how to present them in an engaging manner. Warning: do not be boring. Bragging is the fastest way to get anyone to stop listening to you. Unless someone asks you to elaborate specifically, keep descriptions of your accomplishments in gruesome detail for your grandma. But talk about how you got started, what practicing or honing looks like, and share some thoughts about it. This shapes you as a person because how you spend your time says how you value it QED.

Being interested is much more straightforward. Don’t talk over people (most times), don’t look to one-up them, don’t think about the next thing you’re going to say instead of listening. Do ask questions and expect an equally pompous answer: if you’re asking a question to set yourself up to talk more about you, that sucks. If you’re asking a question because you’re genuinely interested in the answer, that rules.

Takeaway: The key to being interesting and interested is how vulnerable you’re willing to be.

3. Follow up and be persistent, but not annoying.

Most neophyte networkers think that shaking hands with someone is the activity, and having the conversation is the relationship. But I beg you this: it’s not. Most people don’t follow up, send the text or email, connect on LinkedIn, or ask for a meeting or coffee. Then they wonder why their counterpart isn’t doing the same thing out of…pride? Fear? I promise you, if you’re not thinking of doing it, no one else is either. No one’s not thinking about you that much. That said, send the email and follow up a week later, once. If you hear back, great; if not, time to move on. That wasn’t meant to be. It does beg the question of why this person is sharing contact information if they don’t intend to be contacted.

Important: Just because someone hasn’t responded to you doesn’t mean they won’t. It just means they haven’t. If something is urgent, pick up the phone. Your preamble is less than urgent.

Takeaway: Send a follow-up and then follow up once. Don’t write your life story in an email, and don’t bury the lede. You want a meeting or call, and you’re free at these times, etc.

4. Give way, way more than you ask for.

This is true in marketing and in sales, and it’s true in relationships, especially in romantic ones, but also in professional ones. Assume that your give/take ratio is 60/40 and that your partner’s is also 60/40. I would modify this to 80/20 in a professional context if you want something: a job, a connection, a contract, someone’s actual billable time, etc. It’s one of the reasons I continue making exasperated content: my “give” is the ability to help a person publicly tell their story and philosophy to over 2000 people. It’s fun and non-threatening and takes about an hour of someone’s time, which is often available, especially if planned months in advance.

If you’re interested in making a new connection, ask what YOU can do for THEM, or even better, use the information you learned through your follow-ups and synthesize and ask to take the burden of through off your connection even more. “Hey, I saw you’re working on this project and met someone who’s doing similar work—can I connect you?” Something like that.

Takeaway: Don’t ask for people’s time or connections without offering something in return. Nuance: it’s not quid pro quo since there’s always asymmetry in an ask, but remember when someone did something helpful for your unprompted or didn’t want anything in return? Be that other person.

5. Don’t gatekeep, but do protect your network.

Here’s a weird one: if a new someone asks you to introduce them to one of your established contacts, when, if ever, should you say no? The answer is almost sometimes, and it’s situational. Sending an email doesn’t cost anything (for now), but connecting a valued friend to someone you don’t know carries reputational and diminishing returns risk.

• Reputational risk: if you’re not an excellent judge of character and don’t believe you can read people incorrectly, by all means connect the dumbest person you’ve ever met who asked for a favor to someone that you’d die (professionally) for. What does that say to your friend about your ability to make good decisions with limited information? Not a really hard one here, but be careful about the person who’s asking too much too quickly and isn’t interesting or interested. Spot the users and ditch the losers.

• Diminishing returns: There’s only so much you can do to help someone who won’t also help themselves. There’s such a thing as too much inch-deep connectivity that can waste everyone’s time. Avoid this.

Pro tip: When you’re asking for a connection, don’t say: “Who else do you know?” apropos of some basic search. This isn’t always a bad question, and like every bit of advice you’ll ever get, it is situational, but coming forward without being prompted with a handful of people you think someone might know and you’d like to speak to is better than the alternative. There are instances where the conversation is very specific—or very new—and there might be a reasonable time to ask an open-ended question, but I’d much rather tease out some homework for myself rather than burden my connection.

Takeaway: Don’t hide people you want for yourself, but be careful about connecting people you don’t know to people you do. Use good judgment and err on the side of the person you do know.

6. Also, protect your peace. Don’t overdo it.

Once you get somewhat good at this, it’s tempting to broaden your horizons and find rooms to be in all the time. It’s exhilarating to be sought after and to seek out the next person that can become your friend/partner/colleague/wife??1. You can practice small-to-medium talk by simply doing it a lot. Eventually, you’ll walk into rooms where you know more people than you don’t, that’s comfortable, and now you’re not learning anything. And you’re exhausted. And you’ve got too many meetings that only happen once or not at all.

Avoid: Being a serial coffee hopper. It’s too exhausting and expensive if it’s on your own dime. You’re not learning or helping, and you’re known for it. The industry is small.

Takeaway: It’s okay to say no and rot on your couch instead of pushing to your fifth networking event this week.

7. Don’t always seek out mid- or senior-level folks. There’s lots to be learned from your younger peers. (Thanks, Renee)

I love this advice that was given to me by my friend and fellow exasperated human, Renee Autumn Ray2. It’s tempting to seek out folks a career level higher than you for advice and mentorship, but remember, unless you’re literally a baby, you have advice to offer others, too. Seek out folks who look or are younger than you—they definitely understand social media better than you do and have their own lived experience to share that’s different from yours. You might learn a new trend or how young people are consuming information, which can make you better at your job and a smarter thinker because you can communicate better. And so on. Don’t be arrogant and assume that your experience necessarily means expertise.

Wow, Big Brain Alert: Except in one’s own literal lived experience, I’ve found that how long someone’s been practicing often has very little correlation with how good they are at their job. There are definitely benefits to experience, like knowing how to work and being able to heuristic some scenarios to save time and energy (and money), but be wary of the person you meet, younger or older who starts any sentence with, “As a xxxxxxx, ….” or “In my experience as a xxxxxxx, …” or “I went to the University of xxxxxxx, so ….” Reject credentialism and reject experience as proxy for good ideas ipso facto.

Takeaway: Don’t be an elitist or an ageist in either direction. Everyone who’s interesting and interested deserves your attention.

8. I’m split on whether carrying a business card is worth it in 2026.

This was surprisingly the most controversial tip on this list when I socialized the list during drafting. I’ll keep it simple and do a quick pro/con here.

I’m split on this. I use stickers with a QR code of my face, so.

Takeaway: Do you, and it can’t hurt to have some, especially if someone else is paying for it.

9. It’s okay to talk about things other than work; people are interested in getting to know you as a whole person.

If you’re at an industry event, it’s probably fine that you’re talking about topics related to your industry. Try to avoid being overly contentious with people you don’t know (unless you have a reputation for it, like me, and even still, I’m relatively careful about directly offending someone when I first meet them unless they work in “AI” on purpose). And if you’re seeing someone for the second time or more, try to remember a little detail about them or the conversation you talked about last time. It doesn’t have to be about work or a project, but it does have to be fun. I like pop culture and media, I like Formula 1 racing, and I like traveling to new places to eat. Maybe those came up last time. Ask where they’ve been recently or where they’d dream of going and why. Ask about their family if that was a topic that came up. Share a French fry. My god, it’s not that serious.

Takeaway: Ketchup doesn’t belong on French fries. But you belong in the room you’re in, remember that.

10: Remember: it’s not networking, it’s relationship-building. These people can be your friends, acquaintances, partners, or nothing at all.

Some of my best friends are people I’ve met at professional events. We work together and we hang out and do other stuff, too. But don’t force any of this. It’s okay to make professional acquaintances, too. People you can grab a beer with, or someone who makes you feel comfortable being in a new room, because you recognize them from last time. Go say hi and then don’t hang around like a weirdo. My philosophy is this: I want to work with people that I like who can hold their own on their own. I want to hang out with these people and absolutely foam or get excited about anything that’s in front of them.

Takeaway: Thanks for reading 2,500 words on how to be a human being in 2026.

The goal is to make this entire section practical. I’m going to mostly stick to listicles here because these are the quickest way to get these hitters out. Bing bong.

If you have questions, you should send me an email at samuel [dot] b [dot] sklar [at] gmail [dot] come, and I’ll do my best to answer. Share this with a young planner in your life for ~*fun*~.

Ten Ways to Become an Effective Urban Planner

I’m not defining it. Here we go.

1. Going to planning school is not a decision to be taken lightly. At all.

There’s a lingering question that all 21-26-year-olds interested in the built environment have: Should I go to planning school? There’s a flow chart I’ll make for a later date, but the question flow is: if yes, where and why? If so, where, for how long? There is a meaningful, academic difference between planning, design, engineering, policy, comms, law, and social impact. No matter how hard you think about this there is a very good chance you get it wrong anyway.

2. This field is the ultimate liberal arts degree. You will be a lifelong learner.

You must understand that you can be good at your niche—housing, transportation, landscape, architecture, urban design, community and economic development—and you’ll never be good at this job if you don’t also have at least a cursory understanding of the others you’ve ignored. Didn’t like math in college? Tough. That’s your ceiling. Not great at drawing or design? Dive into the history and the art direction side. The stories we’re required to tell run very wide and very deep.

3. Develop very deep, core values. Stick to them.

I won’t tell you what mine are, because you have to make these and earn these as part of your development as a professional, and, not for nothing, as an empathetic human. You can’t approach each project and each neighborhood as though you’re seeing problems for the first time. Bring your whole self to a place, and your stakeholders, the real people you’re helping, will help you define problems better to apply interventions more clearly. This does have a downside of not being able to shut it off. Maybe this field isn’t for you.

4. Also develop domain expertise and/or some level of people skills. Yes, even you, engineers.

You see, (2) isn’t enough. At the beginning of your career, no one is going to believe you know what you’re doing, and you can’t be 27 and setting yourself up as a super generalist if no one knows that but you. So pick something—GIS, design software, transportation planning—and dive all the way in as far as you think you can. You can come up later if you’d like and expand outward (management), or you can reach the depths (individual contributions). Specializing does not absolve you from communication requirements.

5. Bring a reasoned point of view to your work. There is no atonal planning.

One pitfall I continue to see with younger planners is a decisive lack of perspective right as they’re leaving school. This makes sense—academic planning is very different than on-the-ground planning and it can take time and experience to shed the ideology of what logic, data, and information say is “correct” and realize what is correct for the right context. That margin is your point of view.

6. As a corollary to (5), understanding the local politics and its history will help you make better decisions.

Knowing how local decisions are made (politically) will only help shape any interventions you suggest or how you tell certain stories (narratively). Even if you think a project is relatively routine, I promise you it is not, and seeking this knowledge from local experts will only endear you to them and loosen likely acceptance of (good) ideas. There’s always the question of where do you, a city planner, sit during a planning process. Do you plan from within your organization as an advisor?

7. It is OK and likely preferred as you enter decade two of this long career that you bop among the private, public, and non-profit sectors.

Not every career decision will make full or even partial sense until the end of your career, but I will advise you to look to the people over the place. Rarely will you notice a firm/agency’s “culture” outside your immediate team, and anti-labor policies that come every now and again from management. You, too, will have to shape dynamics and decide labor policy if and when you grow into leadership over time.

There are significant differences among the private, public, and non-profit sectors, and each has its place in your career development. Frankly, I’d rather hire someone with a sorta bonkers journey than a Planner I > Planner II > Associate Director journey. You’ve not seen enough, and I’m mostly already bored.

8. Show up to stuff even when you’re tired as all hell, but don’t burn out.

Ninety percent of relationship building is showing up again and again. Being in the same room as the people you’d like to work with or for is exceptionally important. It’s not “networking,” which sucks. Eventually, you develop a reputation, and what you do with it is up to you. It takes years to build and a second to break.

9. Our industry, especially transportation, is full of counterintuitive ideas—you’ll have to learn with cognitive dissonance.

This counterintuitiveness, e.g., just one more lane bro makes messaging extremely challenging, which makes decision-making even harder, which makes good decision-making even harder, which makes getting anything built in a timely or effective manner nearly impossible. Your job is to find a way to cut through the noise. You may train for a long time before your messaging gets through, to make an impact. Don’t give up.

10. Ask for help when you need it, but don’t be an annoying tryhard.

All the people you look up to in our industry were once where you are (and I am) now, and certainly didn’t get to positions of (relative) power by luck (on its own) or by working hard (by themselves). Reach out to people (politely and respectfully of their time and limit bandwidth) and ask for something small. Then do the 9 other things on the list a lot. You’ll get there.