Reflections on Job Hunting in 2023.

Exasperations on Job Hunting. Spoiler alert: it's not great, but it could be better.

Let’s start this with a quick promo: I’m actively looking for work, either on a contract or permanent basis. If you (or someone in your network) is looking for this exasperated person to help with any of your projects, I’m happy to chat! My email is samuel.b.sklar@gmail.com and I’m very responsive on LinkedIn!

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Job searching is exhausting.

I’m not here to complain about job hunting, really. It’s part of the normal process of post-post-recession life that it should be a challenge to find the fit that works for both employer and employee. Skills and credentials matter less and less (I think), relationships matter more and more (I think), and, ultimately, at least in the world of jobs and work that involves the public sector (all planning jobs), it should matter that principles and values align. Investing in labor is a tedious and costly process, and shouldn’t be taken lightly. There is ostensibly a process to match mutually interested parties to do good work.

But the process is totally broken and it’s nobody’s fault, which is why it’s so hard to fix. I’m really not bitter about my inconsistent level of professional success in this arena. The nature of work has changed and those who change with it are doomed to a swirl of confusion; there’s some truth in the return-to-office aesthetic that dominates lots of “work” conversations. But that focus is a red herring—it’s not about work at all. As I see it there are two dominating, intertwined problems:

1. There’s a serious lack of clarity regarding what organization(s) are looking for and communicate they’re looking for and

2. There’s a disconnect between the people doing the recruiting, the people doing the hiring, and the people doing the work.

I want to reiterate that I’m not bitter. I’m coming at this as objectively as possible, and to maintain professionalism, I’m not going to go into specific examples. Instead, you’ll just have to trust that I’ve interviewed at dozens of “top” agencies and companies in the last 7 years and have found almost all of the interviews less impressive than that last. There’s no such thing as an “urban planning” emergency, either, as it applies to day-to-day report writing and “check-ins.” The emergency is our planet and people dying because of the choices we continue to make. Let’s make sure we’re all on the same page about that.

Deeper into the problem.

Let’s quickly dive in:

Regarding point #1: there are two paths workers can travel if not self-employed. There’s the individual contributor route and the management track. Both bring different value to an organization and both are valid pathways to pursue as an employee. As a job seeker, you’re told that you eventually have to make a choice. I’d say I’m about 70% management and 30% IC, which is the nomadic route that is often never accounted for. I’m a professional problem identifier and I produce solutions.

Despite my relative arrogance¹, I do not bring ego to my work. I lift others and others’ ideas up. I’m not looking for credit and praise. If you’ve worked with me, I hope this is the impression I’ve left. I admit when I’ve made an error and I’ll work to fix it. I love digging in and doing the hard analytical and comms work and I love helping to usher along a project’s goals in service of the public. I’ve told no lie that I’m always looking to get better at both, learning from peers, bosses, and charges. There’s always a way to be a better people person and always more skills to refine. There’s always a way, through experience, to try and preempt problems so that they don’t happen again.

There’s no room in an organization for this exact role below Chief of Staff. Maybe that’s what I’m destined for. The challenge there? These roles aren’t as plentiful and available as a lower-tiered role at an organization. Maybe I’m not looking for the right role. That’s got to be it.

Regarding point #2: I think this is the more serious issue in hiring. It starts at the job description level. Actually, I think it starts the first time you’re graded for performance—in elementary school². I digress. There’s an avirtous cycle around crafting job descriptions. Too many job descriptions are too narrowly focused or too broadly written to make sense for narrow thinkers to apply. Lots of government job descriptions are legislatively set and unalterable, so there’s a further disconnect if the exact job doesn’t match the exact description. Scope creep and miscommunications before the process even starts.

Obviously, we’re all looking for the top right: high performance and high trust. My experience is that lots of recruitment sees the process as one-dimensional. But how do you test for trust? It starts with clear signaling from both sides. You have to care; actually, care about building a relationship. The upper left is what happens when you don’t. The caption is too long.

They say what they and then that’s what recruiters look for: many of these recruiters are not trained in the work they’re hiring for and don’t have a sense of who would be good in a role outside of the very vague job description. The managers don’t have time or training to write a job description that would attract the right people. The folks doing the job currently are often not consulted.

It’s a problem of problem identification. But that’s just it, isn’t it? You’ve got to admit there’s a problem and then dedicate resources to fixing it. Too many employers can’t see that this is an issue because they’ve got power and leverage. So many jobs can be taught to the right person—many have to regardless of the level of experience, anyway—so what gives? Power and leverage.

What to do about it.

Anyway here are my fixes:

• Take it seriously, but not SO seriously. We’re talking about livelihoods here, so treating the process flippantly because it’s not your butt on the line is unprofessional and inhumane. On the other hand, it’s work, and work is a four-letter word in our hellscape environment. The planet is dying and we should be working to live not living to work. The work I want to do, anyway, is important to keeping our planet alive and keeping its people and animals alive and safe.

• Dispense with credentialism. Where someone went to school is an outdated heuristic. It does tell a story: that there was a confluence of influence and luck that allowed you to enjoy the resources of an old institution with deep pockets. It’s not a bad shorthand but too often great candidates are overlooked based on where they went to school. As someone who’s been both a job seeker and a job offerer, I’d say my experience is mixed with Ivy sports Leaguers. I think the idea of shortlisting someone based on where they went to school, rather than what they’re doing with their ideas is reductive. Tell me a story. I’ll tell a story.

• Really treat people with respect during the hiring process, which takes too long. Just because the economic value of someone’s time is higher than someone else’s does not give one person the right to waste time or “forget” about it because there are “more pressing matters.” There’s a reason why you’re hiring for a role—to more efficiently distribute resources and responsibilities. Can’t do that if you’re “busy” all the time.³

• Write a clear job description, and hope for lots of variation in responses. Train the team to look for certain personalities or revealed skills during screens and interviews. If you’re getting too many applications of a single archetype, you’re doing the whole process wrong. You want to have to make a hard choice, but you want it to be clear why you’re choosing who you’re choosing. Not just the best of the mehst.

• Both parties should be interviewing each other, despite the power imbalance. Act like it. If you’re looking to disarm your interviewee or lord a job over someone with “tough” questions, you’re just an asshole. Work has changed and “jobs” is a vague enough word that it’s all sort of lost meaning in the deep late-stage capitalist state we’re struggling through (unless you’re some sort of rich person, I guess). An interview should be a conversation, with both parties seeking interesting reasons to work together, not the opposite. Full stop. There are certain corners of the transportation space where this doesn’t seem to be the case. For certain people this works, for others, it’s alienating and exclusive. Yipee, you did it.

• Come clean with yourself and your team about the tediousness of the process. Then embrace it and share it with your candidates. Hiring is very low ROI work that people have a hard time justifying in the short-term mindset that capitalism has destroyed our brains with. We’ve once again heuristically categorized everything into the struggle of opportunity cost: if I’m in consulting, I’m spending more time on hiring, which means I’m spending less on project work — it’s trading a billable hour for a process hour. If I’m at an agency, I want to hire someone but I have to jump through so many legislative and legal hoops. It’s all dread all the way down. We need the time to make the time, but there is no time.

I promise I’m focusing my exasperation.

We’ve got to humanize this process. That’s all. Hire me! Short and long-term opportunities! I’m only a little difficult, but bring a lot of energy, ideas, and execution to the table and I’ve got a good story to tell. Let me help you tell yours.

1. I have a newsletter that I expect people to read. Yikes, big red flag.

2. —but that’s for another conversation about how our entire education system is totally broken and without great teachers fighting against credentialism, we’re totally doomed

3. I know there’s a murky world of legal potholes to avoid here. But process will help with that. We shouldn’t be hiring haphazardly, and that includes making sure you’re keeping yourself out of trouble.