Prologue
In my reflection on being a podcast guest a couple of weeks ago, I shared that I was protecting my summer weekends to focus on my writing. And indeed, it has been a productive, but eclectic run: from musings on a night at the space opera to ruminations on a day in the countryside; from a three-part argument on the basis of identity to an exposition on forging immigrant identity, from an exploration of the mechanics of anger to an examination of the astonishing popularity of “Country Roads”, with a sprinkling of life lessons from parenting not only human children, but also feline ones.
Labor Day this past Monday marks the unofficial end of summer here in the U.S. Technically, of course, the Autumn equinox isn’t until September 22, but at least in the corporate world, this week marks the start of the year-end sprint, for schools, a new academic year, and for college students, the start of job-hunting season.
As such, I’ll be releasing a series of essays built around the theme of “Humanizing Work” – how we can approach our work lives with more grace and human-centeredness. These will complement the essay series I wrote this time last year, DB x AI, on how the shifting of relational and personal formation from human- to machine-centricity will corrode critical societal ligature.
So, starting today and for the next five weeks, I look forward to sharing my thoughts on:
Finding your first job (“Grounding the Hunt”);
Starting your first job (“Stay on Target”);
Navigating the mid-career journey (“True Coloring”);
Leaving a job gracefully (“Better Byes”); and
Handling retrenchment (“More Than Work”)
I recognize this is loaded territory. I cannot possibly cover every circumstance, personal experience, or situation. But what I will offer is what I learnt, what worked for me, and what I wish I had done differently.
I hope at least some of it is helpful.
With that, here we go…
Grounding the Hunt
Advice on Finding Your First Job in the AI Era
The use of AI in recruiting has significantly transformed the game. From using AI to both generate and screen resumes, to candidates using AI to “cheat” during interviews, we are only just starting to descend the slippery slope of depersonalization, at the end of which hiring decisions will be algorithmically determined by API calls. Employers are no longer hiring people. They are hiring digital representations of people. If you are in the job market today, you need to be wise to this, and decide how to grapple with it.
Here is my advice.
Mentality matters. You are going to get frustrated, especially today, here and now in 2025. The market is tight. Employers are narrowing opportunities for entry-level talent. Industries are stressed, and some are undergoing disruption, and none of that is working in your favor. Finding that first job could take a long time. Acknowledge this up front; hope for the best but prepare for the worst.
Play the long game by having the discipline to strive daily, while holding realistic expectations.
Don’t go grok. Grok.AI famously has the ability to adopt the personality you want (unhinged, vulgar, flirty, therapist…). It won’t be long before you feel the temptation to “tune” your resume to “be what they want” because everyone else is doing it.
Don’t. Just be yourself.
Gen Z, I recognize you may still be figuring out who you are. That's natural. But don’t send in a resume that isn’t who you are. Don’t try to be something that you are not. Building your career on a deception is a terrible decision. Even if you get that dream job, pretending to be something you are not will catch up with you in the worst possible way – starting with being surrounded by people who are constantly lying to you about who they are.
That is a living hell.
Mirror, mirror. When I say be yourself, I don’t just mean lying about credentials and experience. After using ChatGPT to improve your resume, put it down for a day then come back to read it. Ask yourself, if I took my name off this and showed this to a friend, would they know it’s me?
Because if your friend doesn’t recognize that resume as yours, one day you may find yourself unrecognizable to your friends, and that would be a terrible shame.
It’s might be ok for your job to change who you are, but don’t let it change who you should be.
Take a Skill Pill. You will need to learn patience. It is a skill that will pay off in the future. You will need a support system. When your teachers, parents and friends say encouraging things, listen. Tell them if you need more of it, and let them give it. Learning how a support system works is another skill that will pay off in the future.
All of this adds up to another skill — self-management. During difficult times, it pays dividends not only in work, but also partnership, marriage, parenthood, and even death.
Fine-Tuning. To run a long race, you need to preserve balance. Don’t be obsessively fixated on getting that job because obsession suffocates and kills.
Instead, keep doing things you love.
Focus on gratitude.
Be a good friend.
You are much more than your job, much more than your paycheck. Don’t lose sight of that. Eventually that interview will come around and you can’t afford to be desperate, soulless, or lost.
You want to be the best version of yourself, so your prospective employer can see what an amazing colleague and contributor you are going to be. But you can’t show them that if you’ve forgotten how to be the amazing son or daughter, sibling, or friend you are today.
Prompt rejection. It’s natural to feel deflated when you are rejected or outright ghosted. But that feeling amplifies every time someone else gets that early offer, and it will downright break you if they beat you in the process. You’re going to feel resentful, and angry.
But comparison is the thief of joy. If you make it a habit to be unhappy because of things you can’t control, you are going to live a very unhappy life, because there are going to be many things you cannot control.
You may find this really, really hard, but try to celebrate others’ victories, even (perhaps especially) the people you don’t like very much.
That doesn’t mean you should be fake. If you need time to absorb what happened and be sad, take it (and see the advice above). But try to bring yourself to the point where you can reframe events, to say good, one of us made it, ok, that’s good for them.
Maybe the next offer will be yours. And you will want others to celebrate your victory. So, try to be the one to start the party. Everyone will remember your positivity and how you stood out as selfless and gracious.
Be the Anti-It. Finally, as you work through all the above, try to maintain a spirit of generosity and do what you can to help others. Not just in their job search, but in whatever they need help for.
This brutal reductionism, this algorithmic addiction, will come to a painful end sooner or later. Nothing in history has survived by embracing dehumanization.
It is the enterprises that believe in, encourage, and promote human flourishing that will ultimately prevail. They will attract the best people, the most genuine people, the most giving people.
At some point you are going to hate this job search process. If you hate it, you have to be the anti-it. And the simplest way to do that is to do the thing that algorithms cannot do: be selfless, be kind, be generous.
Grace and peace in your search, J
Next week: Tips on Starting Your First Job
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Wonderful reminders, Justin. Thank you very much. I really needed to hear this right now!