If I were Eighteen again
Recently the CEO at Anthropic (Dario Amodei) stated that AI could wipe out half of all entry-level white collar jobs in the next five years. l can only imagine how disheartening this statement must be for young adults today, so I thought I’d share how I would handle the current circumstances if I were eighteen again.
I empathize with the challenges that today’s young adults face ❤️🩹 and so I share these thoughts from the perspective of a Millennial who graduated college at the bottom of the stock market crash resulting from the 2008 Financial Crisis—and as someone who likewise struggled to find employment during the early years of my career.
But first, some caveats
I want to start by acknowledging a few important caveats that have shaped my opinions as a result of my lived experience.
Firstly, I’m turning forty this year. I was just prescribed my first pair of “progressive lenses” (think: bifocals) 🤓 and I’m closer to withdrawing from my retirement accounts without penalty than I am to being 18 years old.
Likewise, I’m a Caucasian male in America—which means I’ve been afforded privileges that I did not have to ask (or fight) for. I also grew up in a rural region of the United States (New England). There were literally more cows than people in my town growing up 🐄 and because of this, I’ve been “extremely online” ever since there was a commercially-available “online” to begin with.
And finally, I’m a mid-career Information Security professional in a leadership role. What has worked for me in this industry may not work the same way for you.
Having said all that, in this post I intentionally share guidance that is—in my opinion—timeless. My hope is that it will be useful to individuals from all walks of life and career aspirations.
Read long-form content
Some of the most successful individuals of the 20th and 21st century—Charlie Munger, Warren Buffett, Steve Jobs, Satya Nadella, and Jensen Huang, for example—are known to have been avid readers of long form content (meaning books). This is likewise true for some of the most successful security professionals today—such as Daniel Miessler, Jason Haddix, Dan Guido, and many others.
You see, reading is a skill that develops your brain. And similar to muscle, the brain is strengthened through consistent use and challenge—a process known as neuroplasticity. Unlike listening-to or watching content, reading requires a level of engagement that has been shown to provide both deeper and more complete learning. Seriously, just read anything that interests you!
Having said that, pay attention to the types of content you’re being exposed to—irregardless of the format. In this age of algorithmic recommendation engines, being intentional about the content you choose to consume is crucial. It will shape how you think, which in turn controls how you behave. Just as it’s important be mindful of what you eat, you need to also be mindful of what you feed your brain.
Write long-form content
Additionally, you should be writing (and publishing) your own long form content. It will stretch your mental muscles further, and can produce some really great content that you can use to build and maintain your online brand (more on that later). ✍️ Most importantly, by writing and publishing your thoughts on a perpetual medium (such as a blog), you will have produced a body of work that you can point back to when applying for jobs.
If you’re looking for content to write about, start with writing about things that you’re learning, practicing, or reading. It’s easiest to start with writing about what you’re interested in, and then branch out as you become more confident. And while it can feel daunting to publish content that others might judge or ridicule, the best advice I can offer comes from my best friend and mentor: “Do it scared” (thanks, Jason ❤️).
Finally, it’s also important to recognize when it’s time to update your public opinions—especially when you’ve been presented with new evidence. Being able to do this successfully is a powerful skill at a point in history where so many have been wholly consumed by the latest hype cycle.
Learn how to learn
Before committing yourself to a massive amount of debt from college loans, it’s important to identify the ways in which you successfully develop and retain skills. While reading is more neurologically engaging than listening or watching content—it can only take you so far.
There’s a big difference between knowing something and being able to do it. If you can figure out how to transform what you’re reading into something that can be actively practiced, you’ll further deepen and strengthen the knowledge you’ve gained.
It’s also important to learn how to take effective breaks; I wrote about this concept a couple of years ago. My advice is to try adhering to a “Read, Do, Write, Relax” loop—while keeping everything in moderation—which will allow you to accelerate and sustain your learning while avoiding burnout. I share this because I spent way too much time relaxing and playing video games in my youth. By the time you’re my age, you’ll start feeling a sense of regret for the things you didn’t pursue when you were young (and presumably had more time).
Develop critical thinking skills
After you’ve figured out how you learn, it’s worth exposing yourself to content that challenges and reshapes your thinking (in moderation). To quote Charlie Munger, “never hold an opinion on something when you don’t know the other side’s argument better than they do.” By exposing yourself to a diverse body of content, you’ll identify and develop connections between fields of study. Unlike Large Language Models (LLMs), this network of ideas will enable you to make intuitive leaps—and allow you to capture even greater forms of knowledge over time.
In addition to reading and writing long form content, practicing mindfulness will play a central role in developing your critical thinking skills. You can try taking your learning a step further by asking philosophical questions about the content you’re engaging with. What were the forces at work which led to the creation of a piece of content. 🤔
Practice mindfulness
Presence of mind is a superpower that will pay dividends across many facets of your life—from financial management to relationships, skill development, peace of mind, and building healthy habits that improve your longevity. It’s the thing that helps you acknowledge and redirect your thoughts before they become actions.
In order to cultivate presence of mind, I’ve found that meditation is an essential practice that enables you to achieve a sense of mindfulness that lasts. For better or worse, mindfulness is not a skill that can be developed from reading books or sitting for a few practice sessions—it requires patience, consistency, and longterm commitment in order to draw out all the benefits it can offer.
Over the last 11 years, I’ve found success adhering to a daily meditation practice by using the apps HeadSpace and Rainy Mood, along with a set of mala beads that I wear wherever I go. 📿 Noise cancelling headphones can also offer an extra level of tranquility in loud settings.
Build & maintain a public brand
After you’ve established these foundational skills, arguably the most important advice I can offer is to build and maintain your online brand; I wrote about this in my very first blog post three years ago. As my friend and mentor, Jason Haddix, recently shared: “employers now expect you to have a body of work they can reference before they’ll consider you for a role.”
You can see for yourself how successful this strategy is from recent college graduates like Olivia Gallucci, who has published a mountain of content to showcase her skills. She now regularly speaks at conferences around the world, and successfully landed a Senior Security Engineer position right out of college. 👩🎓
I previously shared some resources for building your brand in my “Advice for breaking into InfoSec” blog post from two years ago—and in 2025, your public brand is the difference between being a “Non-Player Character” (NPC) 👤 and being a “Player Character” (PC). I believe this analogy from Daniel Miessler effectively summarizes why passive individuals (NPCs) are no longer achieving job security (or career success) in the Information Security Industry.
Seek out mentorship
For starters, it will be easier to acquire strong mentors if you already have public content that proves you’re putting in the work. As a mentor myself, I can tell you there’s nothing more disheartening than spending time and effort to help someone grow—only to have them continuously ask for things while putting in zero effort. It’s even worse when they complain about making zero progress. 😞 Mentorship alone cannot make you a better security professional; only you can do that. And that means putting in the work.
That said, it’s worthwhile to pursue a mix of mentors who can provide guidance on different aspects of your career. Some can help you develop the hands-on skills you need as an individual contributor (IC), while others can help you navigate business politics and leadership challenges. Some of the greatest mentors out there will help you develop skills that span the entirety of your career.
I’ve personally benefited from having a number of different mentors over the course of my career, including: Jimmy Vo, Will Vandevanter, Ethan Feller, Casey Dunham, Lea Snyder, Jason Haddix, Josh Corman, Bryan Inagaki, Mike Zusman, and many others. I’m incredibly grateful to all of them for having helped me progress in my career. 🫶 Many have even become lifelong friends who I continue to learn from.
Thoughts on formal education
Should you pursue college?
As LLMs chop away at the “lowest rungs of the career ladder,” you’re going to need public content you can showcase to prospective employers. Pursuing a degree at a prestigious college or university is no longer guaranteed to land a lucrative job. Even Summer internships don’t automatically lead to job offers these days.
So why would you want to put yourself through four years of toil and take-on incredible amounts of debt? Well, generally speaking a college education provides a greater positive benefit to marginalized groups when seeking employment. Choosing not to pursue college may inadvertently harm your long-term career prospects, so carefully weigh this into your considerations.
That said, if I were to pursue college again, I’d spend at least the first two years living at home and attending a small, community college in order to reduce costs while completing General Education requirements. After that, I would only consider the leading schools in the field I’m pursuing—and even then, I would only attend the school that offers the best financial aid package. 💸
While at college, I’d also spend a non-trivial amount of time either in a research lab working to publish content—or in a club that actively participates in Capture The Flag (CTF) competitions. 👾 I’d strongly encourage focusing on CTF challenges over things like the Collegiate Cyber Defense Competition (CCDC), as the types of skill development (and job opportunities) available to talented CTF players are much more lucrative than the alternative. Just ask Dominik Czarnota.
What about certifications?
Like a college education, certifications also have a greater positive benefit to marginalized groups when seeking employment. That said, not all certifications are created equal. Pursue certifications that offer a practical exam as a way to highlight your ability to actually perform a given task at a professional level.
Certifications like the OSCP, OSWE, etc. continue to be more valuable than the CEH, CISSP, or similar because the latter certifications are just “paper tests.” As I said before: there’s a big difference between knowing something and being able to actually do the work. 👍
That said, certifications are not a replacement for building your brand, or having public content that showcases your skills. They’re also not a substitute for a multi-year college education, but they can serve as public proof of your abilities. At the end of the day, leaders look for Attitude, Aptitude, and Engagement when hiring junior talent. Make it really easy for hiring managers to see these elements through your public content.
Are trade schools & bootcamps worth it?
While the trades (plumbing, electrical, carpentry, etc.) are considered in-demand jobs that pay exceptionally well for the investment costs, such jobs require travel to work sites. Likewise, there’s only so many plumbers, electricians, carpenters, mechanics, etc. that a given city, state, or region actually needs.
I believe that trade schools are great for individuals who are mechanically inclined and skilled with their hands, but there are tradeoffs to consider—like your ability to meet and build relationships with people your own age, the demand for a given trade in your area, and the ability to maintain the long-term physical fitness required to work a trade. 💪
And as for coding bootcamps and the like—save your money. LLMs are, unfortunately, taking the jobs that bootcamp graduates once fulfilled. If you’re really interested in learning a technical subject these days, you’re better off buying a book, going to Udemy, or even pairing with an LLM to start learning the material.
On AI and skill development
LLMs aren’t going away, so it’s worth spending time figuring out which tools add value to your workflow—without inhibiting your critical thinking abilities, or deteriorating your skills. I wrote about this a couple of years ago in a post titled, “Life after the AI-pocalypse.”
In terms of skill development, one example for using an LLM poorly would be to have it write your public content. This is both cheap and easy to spot. 🤖 You gain nothing in terms of skill development from such “zero calorie” content generated by an LLM on your behalf.
On the other hand, using LLMs to get past the “high activation energy” threshold for learning a new skill, starting a new project, or writing new content is worth pursuing. Doing this successfully requires an understanding for how LLM tools can be used, how frequently they succeed (or fail) at a given task, and the amount of critical thinking required to review their output. Failing to critically review an LLMs output is like flying a rocket ship without instruments or a window—you’re effectively blind. You’re also likely to crash and burn as a result.
Having said that, I strongly recommend getting a whiteboard if you’re working with LLMs to write software. This will help you understand how the LLM code fits together, and will allow you to more easily identify the architectural (and security) flaws the LLM introduced to your codebase.
For other tasks, be mindful of how LLMs will shape the way you think about a problem. By selecting and presenting you with a range of options, an LLM will mentally abort the other ways you might approach a given challenge. It’s also worth noting that LLMs will present you with falsehoods from time to time. A whiteboard can help you work through this problem by forcing you to “think outside the box.” Seriously, draw a box for “LLM Outputs,” and then force yourself to identify all of the other adjacent ideas worth exploring.
The alternative, AI-averse path
Finally, as I also wrote about in “Life after the AI-pocalypse,” there is another path available to those who refuse to allow AI into their life—but it should be stated that pursuing this path is incredibly challenging. In the earlier blog, I described this path as creating “Banksy-like” content and experiences, but I’ve discovered a better way to describe what I mean.
The Japanese have a specific word—shokunin—which describes an artisan whose craftsmanship transcends form and function. The works of shokunin are considered so masterful as to be a form of art due to their lifelong devotion to the craft.
Hayao Miyazaki is a shokunin of Japanese animation. There are individuals who make sushi or ramen who are considered shokunin. 🍜 I would consider Allan West a shokunin. Heck, there are people who shine shoes who have risen to the level of being considered shokunin.
All that is to say, if you’re going to pursue a lifestyle free of AI tool use, you need to become a shokunin. You need to produce the sort of crafts or experiences that rise to the level of being an art form, and produce works that generate real (or perceived) scarcity from the extreme attention to detail requried—which in turn will hopefully generate demand.
Think: high-end, hand crafted watches; Unique, physical works of art; Hand-bound manuscripts from books written on a typewriter—errors and all; etc.
If you can produce either crafts or experiences that rise to the level of an art form—and get people to pay you for it—then you’ll truly be free from ever having to think about engaging with LLMs. And if not, then hopefully you’ve adopted the other recommendations I’ve shared in this post.
Either way—may you live in interesting times!
Many thanks to Olivia Gallucci, Daniel Miessler, and Gabe Sherman for reviewing this post and providing feedback!
If you found this post interesting or useful, I invite you to support my content through Patreon — and thank you once again for stopping by 😊 While I consider my next blog post, you can git checkout other (usually off-topic) content I’m reading over at Instapaper.
Until next time, remember to git commit && stay classy!
Cheers,