A Zoomer’s Guide to Getting (and Keeping) Your First Job
The content in this article reflects my own research and experience. It does not reflect the opinions of my employer.
Most career advice is garbage. It’s either written by productivity influencers with a coaching seminar to sell, or by anti-work haters who think having no ambition counts as class warfare.
We can do better. I’m 26, but I’ve gotten involved with recruiting and management at my organization. I know what it’s like to be on both ends of the table as a young person navigating the post-COVID era.
Who I Think You Are
In this guide, I make some guesses about you. The more wrong I am, the less this guide will apply to you.
You’re a Zoomer in your early 20s. You got a smartphone in high school and spent some amount of high school, college, or grad school on Zoom.
You went to school and are looking for a full-time job in the United States.
You’re looking your first “knowledge work” job.
Your prior work experience, if any, is all in retail, food service, and maybe internships.
If you had internships, your employer at best handed you a discrete project, left you alone for 3 months, and asked for a single presentation on your last week.
You’re facing difficulty in finding work. You’re not crazy—the first job is the hardest one to get.
You want career success beyond the minimum to raise a family in a quiet town.
A quick note on family money—in small cities like Tulsa, Chattanooga, Des Moines, and Colorado Springs, $40 an hour is enough to raise two kids with a stay-at-home spouse—eminently doable with professional qualifications. If you just want a house and family, that’s easier than you think.
This guide will assume you want more.
Knowing Where to Look
The Landscape
Let’s talk big picture first—it doesn’t feel it, but you have serious leverage in the job market.
Zoomers are scarce compared to Millenials. The reason companies ask for 3-5 years’ experience on entry-level jobs is because overqualified Millennials were that desperate in 2012. But now everyone’s scrambling for young staff...
...Because the Baby Boomers have largely retired. The more staid the industry, the more catastrophic the labor shortage has become. Employers are desperate.
On top of these demographic shifts, the past 3-4 years gave us COVID, the Russia-Ukraine War, the advent of generative AI, and (finally) some real movement on climate change. Every single industry is burning. The old rules don’t apply anymore.
Crises are the best time to be young and ambitious. If you pull the career-track equivalent of “buying the dip,” you’ll reach your early 30s as one of the youngest people to fully understand the New Way of Things once that coalesces.
But you need a story to build your career on—you need a pitch.
Building Your Pitch
You’re not owed a job. You have to convince someone to pay you. I’m not sorry.
The bad news is that if you’re fresh out of school, you technically have no skills. Don’t worry if you’re qualified for the job—you’re not. The good news is that no one hiring entry-level staff cares. Employers hire entry-level staff because 1) they’re cheap today and 2) could be valuable in 3-5 years.
Your pitch should keep that trajectory in mind, and it should have three components:
Your industry
Whether you’re a specialist or a generalist
Your temperament
Let’s go piece-by-piece.
Your Industry
This is pretty straightforward. The first level of filtering is your major, and the second level of filtering is the advanced classes you took in your senior year of college or post-grad training. But there are two exceptions to this:
Exception 1: Business, Accounting, & Entrepreneurship
Business school technically prepares you for any industry. But you have to pick one and learn the technical jargon quickly. If you don’t know what to pick, go with something boring, invisible, and essential—like commercial shipping. The challenge and pay will make it interesting for you.
Exception 2: English, Philosophy, & History
If you picked an old-school liberal arts major, you majored in “read anything and communicate what it means.” Every industry lives on narratives, so their writers get paid accordingly. When in doubt, pick an industry that’s complex in a way that spreadsheets can’t assess, like law, advertising, or civil service.
Specialists Vs Generalists
To build a successful career, you need to be hard-to-replace by your 30s and indispensable by your 50s. There are three rough ways to get there—you can be a Specialist, a Generalist, or a True Generalist.
Specialists
Specialists do one thing at a high level. They typically have specific certifications that take 5-15 years to achieve. Think “licensed marriage and family therapist,” “professional engineer,” or “US Air Force pilot.” A Specialist can work in a lot of contexts, but they are one of a few people who have the licensure, training, and (often) liability insurance to do what they do. Specialists have a straightforward path to employment because the qualifications are clear: have the right letters behind your name, or go back to school until you do. A max-level Specialist is a wizard in a tower or a manager of lesser Specialists.
If you want to keep your head down and avoid office politics, become a Specialist.
Generalists
Generalists are go-betweens, working in two or three disparate fields at the same time. They typically have parallel tracks of skills, which allows them to translate jargon across teams. This is why most companies are held together by Generalists. Think “engineering manager,” “technical sales representative,” or “fine art seller.” A Generalist can combine any two or three fields, but there’s typically at least one technical or creative field and at least one business or communication field. If you feel like most of your college education didn’t prepare you for work, it’s likely because your major filled just one of multiple skill tracks you use at work. Generalists have to hunt a bit for jobs, but they can find their niche by drawing a Venn Diagram of things they’re good at and finding work at the intersection. A mid-level Generalist typically becomes a project manager. A max-level Generalist typically becomes a Director of Something or a C-Suite executive.
If you want to maximize your pay and influence, become a Generalist.
True Generalists
True Generalists are strange creatures. We draw a circle on the map of human knowledge and commit to learning everything in that circle. This returns a miles-wide, inches-deep, “big picture” understanding of the world centered around some locus point like personality psychology, geography, video game music, or—in my case—residential energy use. A max-level True Generalist advances the future, because they are best-qualified to do jobs that don’t exist yet.
The challenge with being a True Generalist is that committing to knowing everything in a given circle doesn’t make you employable until you know everything in that circle. Until then, you’re handicapping your career by being under-qualified across the board relative to your peers. If this is how you want to work, I suggest you work analyst positions at consulting firms until someone lets you write your own job description.
Temperament
Two of the biggest factors in your personality are genetics and early childhood experiences, so by age 20, your personality is stable enough to make years-long bets on your career. This is important, because your personality is your primary differentiator for entry-level jobs.
Know yourself. The Enneagram and MBTI models are bunk, but the Five-Factor Model has some real science behind it. The best personality assessment accessible is the IPIP-NEO by John A. Johnson. Refresh your understanding of bell curves, take the 30-40 minute assessment, and copy-paste the results into a Word doc—the website doesn’t save your results.
Pulling Together Your Pitch
Once you have your pitch components, you need to pull them together into a coherent narrative. Let’s take my background as an example:
Industry: I got a Bachelor’s in Electrical Engineering with a minor in Philosophy, with my most notable classes being:
Electric Infrastructure & Delivery in the Developing World
Solar & Direct Energy Conversion
Senior Thesis: Using computer vision to identify lightbulbs from mobile cameras.
Senior Design Project: Using thermoelectric coolers to build a low-cost air conditioner.
Based on these classes, my industry of choice should be something like “the green energy transition”—and it is.
Specialist or Generalist: As I mentioned above, I’m a True Generalist freak. I know a little bit of everything about the green energy transition: building energy systems, utility distribution networks, global energy markets, AI implementation, technical communication, and so on. And I’ve started an MBA program, which adds a whole other category of things to know, from accounting to management.
Temperament: The most important factors on my Five-Factor assessment are my Agreeableness (high), my Openness to Experience (very high), and my Extraversion (freakishly high). I’m typically the chattiest person in the room, and I’m so energetic that caffeine doesn’t do anything to me.
If we pull all this together, my pitch for an employer becomes:
I know the future of green energy, I can get other people excited about it, and I have the technical chops make it happen faster.
Yes, it’s cocky. Your pitch should be, too—you’re selling yourself!
I was qualified for a job that didn’t exist when I graduated college in 2019, so I worked in consulting for a couple of years until I found a company that let me run wild.
OK But What Jobs Do You Apply For?
First off, don’t mass-apply to every job you’re vaguely qualified for. That just drives you insane.
Instead, target your applications to specific companies and job openings. If you’re a Specialist, this is straightforward. If you’re a Generalist, you’ll have to root around for companies that fit in your Venn Diagram. Keyword search is your friend. If you can send tailored resumes to every position you apply for, you’re on the right track.
Prioritize jobs in boom towns, headquarters, and skunkworks labs—wherever the action is. Do not seek out fully-remote jobs, “soft girl” jobs, or jobs in low cost-of-living areas. A “flexible” job implies you have a life that’s more important than work—and if you’re a young adult with ambitions beyond humble comfort, you should not. You can seek out nice housing and work-life balance once your career has momentum, but in the meantime, you should prioritize growing your skills in the presence of hot singles. You can have it all—just not at once. And the slow-life strategy of most Zoomers means no one really expects you to make serious money until you’re thirty. Move to a remote gig or a cheaper city once you have the skills and influence to name your price.
Applying for a Job
The best way to find a job is through your network. In your mid-career, this will look like friends and old colleagues pointing you to a cool position they caught wind of. In your late career, this might look like someone calling you and saying, “I need a Director of Widgets, and you’re the only person who can do it.”
Your network is simply the people in your life who know you and like you. It’s your relationships up close and your reputation from afar.
But if you’re fresh out of school, you have no reputation and only a few connections. Building your network is a slow, incremental process that will help with your second job. This is why your first job is always, always, the hardest one to get.
Start With Whatever Network You Have
You may not have a large network, but you should have something—family, friends, professors, internship supervisors, alumni in your school, alumni from your fraternity or sorority. Does someone with power, influence, and budget like you and think you’re going places? If so, they might offer you a job or call a powerful, influential friend who can. If someone I respect gives me your resume and says, “I’ve worked with them, and they’d be perfect for your job opening,” I’m immediately vouching for you in the hiring process.
If literally no one of consequence has found you worth investing in...you’ve fucked up.
Career Fairs Are the Next Option
Career fairs are the workaround for the fact that college students have no network. I may not know you, but I can at least talk to you—remember, you have no skills, so I’m checking for temperament.
But the odds are against you. Working at a small company, I can get 20-40 resumes from a single career event. The day after the event, I sit down with some higher-ups, and we shuffle through the resumes. We spend at most 30 seconds on each resume, looking at names that I’ve mostly forgotten in the intervening twenty-four hours. You win the career fair if I remember you when we get to your resume.
Pick a Shortlist of Companies the Night Before
Do some research on five, maybe eight employers. What does my company do? Why am I hiring people in your major? What’s happening in my industry? A couple of minutes of research will distinguish you the 80% of students who lead with, “So what does your company do?”
Then, make a game plan. Order your list of employer conversations based on your energy for social interaction. Do you need two conversations to warm up? Do you only have the endurance for four conversations before you need a break? You should be your most social for the employer you think you have the best shot at.
Dress Formal, Especially if You’re Not Required To
I don’t expect formal clothes at a career fair, but you have five minutes to be memorable—take every advantage you can get.
For the ladies, think “girlboss”: pantsuits, dark colors, maybe pencil skirts, maybe heels, maybe some hoop earrings for flair.
For the fellas, spend five or six hundred dollars on a made-to-measure two-piece suit from a company like Indochino or MTailor, and another two or three hundred for formal black leather shoes and a matching belt. Your options for the suit are navy, black, or gray; pick one. You need a matching set of jacket and slacks, but you don’t need a fitted shirt. Yes, this is a lot of cash, but this is your career, and I can tell when you bought off-the-rack. Spend money to make money.
Prioritize Interesting Conversation
Talk to me. If you already know what I do, lead with industry chatter, or with why you care about what I do. If you don’t (because you’ve already completed your shortlist, right?), then listen closely when I explain what I do. It’s okay if the conversation hinges around your pitch or your resume, but it’s better if you break out the resume after a good conversation.
I go to a career fairs with a script: This what we do, this is why we do it, and we’re looking for this. If you break me out of my script, I’ll remember you better. If you truly impress me, you become a top candidate on the spot.
Resumes are the Weakest Link
A resume—by its nature as mere text—is the weakest part of your application. If that’s all you have, you’re just a name in a pile. And hiring managers will only leaf through that pile if all their other leads ran dry.
I’m give a resume thirty seconds. If this is your first impression, you’re already screwed.
Let’s See Paul Allen’s Resume
You have limited scope for individuality in a resume. I might notice if you used Canva or LaTeX, but I won’t appreciate a distracting layout. Your self-expression is largely in your typeface choices. You don’t have to go crazy, but don’t use defaults like Arial or Calibri—that reads as laziness.
What I’m Looking For
I’m looking for three things:
Major: Are you in the right industry? If you’re looking for an internship, I’m checking your graduation date. Rising seniors and grad students are looking for “real” internships, but I’ll temper my expectations for underclassmen.
Key Classes: Again, are you in the right industry? I don’t trust anyone’s “Skills” section, but if you took a class in something, I’m inclined to believe you know it.
Projects: Internships, senior theses, research under a professor, lower-level class projects if you’re applying for an internship. I’m trying to gauge how interesting you are. What did you do? How? With what tools? What was the result? These will come up in an interview. Prioritize your two or three most relevant projects to the position—the more projects you have, the more you get to tailor your resume for each position.
Other Notables
If you worked a retail or service job through college, give it a line on your resume—it shows work ethic.
If you’re a U.S. citizen or permanent resident, mention it up top, especially if your name doesn’t sound white.
Pronouns are okay, especially if your first name is androgynous or uncommon in the United States.
Good luck—you’ll need it.
The Interview is For You, Too
If an employer selected you for an interview, you’re probably in a short list of 3-5 per position. We already think you’re qualified enough for the job, and the interview is just to assess whether we like you.
You don’t have to impress the interviewers again—you should instead assess whether you like us, because the only thing worse than not getting a job is getting a job you absolutely hate. For this reason, if the interview feels like you’re idly talking shop for forty-five minutes, that’s a good sign.
Interviewers will ask you questions like “tell me about a time when you [blank].” It will sound like HR-speak, but the point is to hear a story about how you work. We want to know whether you’re a fit for the company—the cliché is real!—because workplace culture genuinely makes or breaks an organization.
The most important part of the interview is the last ten minutes when we ask you for questions. Grill us. First, because you should know what you want from work and whether this company can give it to you. Second, because tough questions let interviewers know that you were paying attention.
Succeeding in Your First Job
Congratulations! You just signed the offer letter. You’re not done. It takes three to six months to find your footing at a new job, a year to become a fixture in your team, and up to two years to rack up some real wins to your name.
Those wins differentiate a career from a series of jobs.
Getting Shit Done
If you attended even a moderately prestigious college in the early 2020s, I assume you know how to work hard—even if that hard work only comes in late-night cram sessions. But I want to address some unfortunate myths sold to us Zoomers about how to succeed in the workplace.
MYTH: You Should Have a Side Hustle
For the start of your career, you should have three priorities—in order:
Your health
Your career
Literally anything else
Good health—physical, mental, spiritual—comes first, because it enables everything else in your life. After that should come your career—the sooner you achieve some wins, the better. For this reason, don’t concern yourself with side hustles. They dilute your effort at the time when all you have to offer is effort—remember, you have no skills yet.
If you want an extra stream of income, earn a promotion.
If your job doesn’t challenge you, take on more challenge.
If you still have time to spare, exercise more, work longer hours, or ask your work to pay for night classes.
Diversify your assets, not your effort.
MYTH: Passive Income, as a Concept
Anyone selling you a passive income or “online business” strategy is a con artist trying to take your money. The labor theory of value is real—you don’t make real, sustainable money without producing something people want.
No amount of talent, coaching, or first movers’ advantage can replace in-demand skills and hard work. Even investing takes effort if you want to outpace an index fund without losing your shirt, because you can only pick two out of high returns, low risk, and low effort. If making a lot of money was easy, everyone would do it. Even if you found a magic money machine, you would lose to someone who took apart their money machine to made it work better.
Being your own boss won’t give you easy money.
Trading in risky assets won’t give you easy money.
Doing what your parents did won’t give you easy money.
Do you know how to make $10,000 per month from the comfort of your home? You work flat-out for ten years until you’re so important that you can negotiate a fully remote position in return for a 30% pay cut.
Do you want a new Ferrari? Then become the CEO of a firm valued around $500 million. Think “mid-size shale drilling company” or “small tech startup launching an IPO.” And that’s just for the base model.
I don’t care what the market is doing; the best financial strategy is to be more skilled, hardworking, and adaptable than everyone else around you.
No shortcuts.
MYTH: Going “Above and Beyond” Isn’t Worth It
A lot of “quiet quitting” and “anti-work” advocates are motivated by the belief that hard work doesn’t pay: your boss will take credit for your work, your coworkers will take your effort for granted, and you’ll never get promoted anyway.
But that’s largely a problem of communication—does anyone in your office know how hard you work? Your boss and coworkers are too busy to know exactly what you’re doing with your time—and it’s a problem if they’re not. So if you do a lot of great work without telling anyone, no one will know that you deserve a raise.
Frequently tell your colleagues what you’re up to, especially if you’re helping them.
“I’m working on the XYZ project this week. I’ll give you an update on Wednesday.”
“I ran that analysis you asked for. It’s in your inbox now.”
“I got your email. It’s handled.”
“Do you want help with that? I have some time Thursday.”
This is how you build a reputation as someone who gets shit done. This is how people know your value.
And when you achieve those career-defining wins, write down what you accomplished and how you did it. That blurb goes on your resume, on your LinkedIn, and in your pitch when you float the idea of a raise no less than eighteen months into your job.
MYTH: Burnout is Caused by Your Job
If you’re burnt out, it’s likely some combination of:
You’re neglecting your health
Your job doesn’t mean anything to you
You’ve committed to at least two people’s worth of work
I cannot stress enough how important your health is to your work. I exercise 3-5 times per week, eat clean, track my sleep, and avoid alcohol because if I didn’t, I would not be able to work as hard as I do. Health is not a product of success—it’s a factor towards success.
If you’re healthy but still burnt out, assess you care about what you’re doing. If you get Sunday Scaries, you’re in the wrong job if not the wrong career. If you don’t wake up excited to go to work, you will fall behind people in your field who are.
If you love your job and you’re still burnt out, you’re probably overburdened. A little bit of overwork is good for you—it keeps you focused. But if you can’t remember all the things you’ve fallen behind on, you’re dramatically overcommitted. Tell this to your supervisor, and work out solutions. Learning how to pass off tasks to someone else—or decide a task just won’t get done—is your first step towards becoming a manager yourself.
If your work life is fully dialed-in, then your burnout may truly be from a toxic workplace suffused with the envious and craven. But be careful about blaming burnout only on your job. Even a burning company still offers a chance at glory, provided your coworkers at least get out of your way. You should make an exit only if your coworkers actively hinder your ambitions and resent your success.
The anti-work types claim burnout is only your boss’s fault. It’s only half their fault—if you’re dialed in, you will work harder than you thought possible and love it.
MYTH: Gen Z is Ready to Lead
No, we’re not.
We, like everyone before us, will start at the bottom of the hierarchy and rise with experience.
Yes, there are some folks our age leading protests, running startups, and printing money making “content” for social platforms. Assume you’re not that remarkable. You have to convince people you’re worth following, and most people want to follow competent figures. Remember, you have no skills yet.
Your career will last at least 40-50 years. You’ll be considered “young” until you’re 30 or even 40. If, by age 55, your title has words like “director,” “principal,” or “chief,” you’ll have at least ten years to be the Big Cheese, which is more than most get—zero.
Have some patience.
Earn your seat at the table.
MYTH: You Need to Be Successful to Be Happy
All the advice I’m giving is optional. Material success is optional. You don’t need a rockstar career to have a good life.
I’ll repeat myself—in small cities like Tulsa, Chattanooga, Des Moines, and Colorado Springs, $40 an hour is enough to raise two kids with a stay-at-home spouse. That salary won’t let you afford a daily Starbucks habit, regular trips to Europe, or a lifted Cummins, but did you want any of that, really?
Cost of living is only prohibitive in the big cities. A dollar goes further than social media says it does. Frugality and humility are underrated virtues.
I make enough money already. I continue to work because I want more: power, glory, luxury, legacy. That—to me—is worth studying when I’m not working, exercising when I’m not studying, sleeping when I’m not exercising, and reading with whatever time is left.
I love my life. But it’s optional. Success is optional.
Getting Into Office Culture
At the top of this guide, I assumed you have no experience in a knowledge work office as an adult employee. And unfortunately, no one will teach you how to act in that office.
I’ll give a first pass explainer for you.
But first, a disclaimer:
Most People Are Not Evil
At most one or two percent of people rate pathologically high on the Dark Triad personality traits of narcissism, Machiavellianism, and psychopathy. People don’t get into HR to ruin lives. Normal people dislike virulent bigots. Your boss probably hates doing disciplinary actions.
The single common factor to your lot in life is yourself. You can’t choose the hand you’re dealt, but you can play that hand well or poorly. If literally no one is in your corner, that’s not because of racism, or homophobia, or anti-male bias. That’s you. If you believe that someone tries to stop you every time you try to advance, you have an “external locus of control,” which you must fix.
Most people are normal.
Most people are trying to help.
Most problems can be solved with honest, empathetic conversation.
And sometimes, you’re actually in the wrong.
Business Casual, Explained
The first-pass answer to “How should I dress for work?” is “Dress like your boss.” Underdress too much, and you look unprepared for the job. Overdress too much, and you risk outshining the master.
If your job requires a suit, you already know that. If your company lets you wear T-shirts to work, it was probably founded by a Millennial. But in most cases, you’re dressed in business casual.
Business casual is named as such because it’s what used to be Casual Friday clothes. Polo shirts were originally for polo, the sport. If you went to work in business casual in the 90s, it would be the equivalent to going to work in 2023 in athleisure.
And if you’ve gone to Zoom school, you probably need to buy a new wardrobe.
The men have it simpler. Your outfit should comprise:
Tops: Collared shirts, always tucked in. “Spread” or “Straight Point” collars are the default, but a “Button-Down” collar is also fine. Polos might be okay in the summer, sweaters atop collared shirts might be okay in the winter. The top button is unbuttoned. Sport coats and blazers are for meeting bigshots, and they should be tailored. A tie is probably too much.
Bottoms: Slacks or chinos. Maybe jeans, but only if they’re dark and fit like slacks. Consider getting your work pants tailored. Your belt options are black or brown with simple buckles.
Shoes: The uppers must be leather. Get at least two—one in black, one in brown, matching your belts. Loafers are okay, but laces are preferable. Leather shoes with sneaker soles are probably fine. If your job allows full-on sneakers, use an understated colorway.
Women get the same options as men as well as few extras: a wider variety of dressy tops, knee to midi-length dresses and skirts, and heels if you want to elevate the look.
The colors you are allowed are:
White (for tops)
Black
Any shade of grey
Any shade of brown (for bottoms)
Any shade of blue
Light shades of purple or green (for tops)
Other light pastels (for tops, for women and bolder men)
Subtle geometric patterns are okay—checks, plaids, dots. Florals are okay for women and a bold move for men.
If you dress androgynously, bias towards either masculine or feminine. Most people above 30 only know “he/him” and “she/her” and will sooner guess wrong than ask your pronouns. Make sure they can guess easily.
Yes, business casual is stifling and conformist. Deal with it. You have options for flair, but they’re pretty limited:
Hairstyles, as long as they’re not dyed in dramatic colors
Tattoos, as long as they’re not on your hands, face, or neck
Earrings, even on men
Glasses
Watches & jewelry, as long as they’re not too flashy
Your boss and their peers are hiring a lot of Zoomers. We like weird hair and funky shirts, and they will slowly learn to deal. Someday, even brightly dyed hair will fly in an office environment, but in 2023, we’re not there yet.
Keep it classy, people.
Shooting the Shit is Good, Actually
If you worked in a retail or food service job, you were probably discouraged from lazing about or chatting too much with your coworkers.
That’s not the case in many offices. I once interned a government contractor, and the whole team decided to get coffee. We probably spent an hour there, at which point someone asked, “This is billable time, right?”
And the boss—who had been at coffee with us the whole time—said, “Yeah, this is billable.”
Office cultures are built on the fact that few people can stay focused for hours at a time. There will always be downtime, coffee breaks, water cooler gossip, and post-meeting chatter. Your workplace is a social group, and you are expected to participate.
Get friendly with the people near your desk. Ask how people spent their weekends. Have weekends interesting enough to talk about. Tap into threads of gossip. Linger about as long as your coworkers do. Learn which coworkers say “fuck” and when. See how the conversation changes when the boss is around. Say yes to every invitation, and notice that if the boss comes to lunch, they typically cover the tab.
If your social skills are crap, you’re not the only Zoomer with this problem. If you worry you’ll sound stupid, don’t worry—you already do. Remember that almost every YouTube tutorial on conversation applies to workplace conversations. This is why you should avoid remote work at the start of your career—awkward workplace banter is expected from an entry-level hire but off-putting from, say, a thirty-something.
By the way, if you develop a crush on a coworker, note that in the 90s, a sizable minority of relationships started at work. Make a move. Only freaks would describe asking someone out once as sexual harassment.
Your Boss is Human, Too
Management roles don’t abruptly strip the humanity out of people—in fact, a lot of people get promoted management in spite of their interests.
If your boss is bad, you’ll learn pretty quickly, and your coworkers will corroborate your experience. Follow your coworkers in that case. But if your boss is at least moderately competent, you want to keep them updated on:
What you’re working on
What challenges you’re facing
What you’ve gotten done
Try to minimize the amount you ask your boss for help. Asking for help is good, but your boss is probably quite busy—they hired you precisely because they don’t have the time to do your job. If you can ask your coworkers for help instead, that’s better. If there’s an extant resource with the help you need, that’s best. (If no such resources exist, building them is a great way to make everyone like you.)
The best thing you can do for your boss is remove items from their list of things to worry about.
And from there—chat with your boss too! They’re not some mythic creature; they’re a person in the office too.
Getting Ahead
The most powerful thing you can do for your career is to find someone of incredible vision and follow in their slipstream for 10 years. Do what they say, follow them if they switch jobs, and take notes on what they think until you have a vision of your own.
This is what mentorship looks like. Monthly coffee chats with someone smart doesn’t cut it. You need someone to open doors on your behalf and point you in the right direction, and you earn their personal investment by being a standard-bearer to their cause.
But that is difficult, because people of that level of vision are rare. So your alternative is to read widely, build a model of the next decade tailored to your career, and make sure you’re ready for that job you’ll have in 10 years.
I’m still on that journey, so I can’t speak to what you need to do in detail. Here are some rough notes from what I have figured out so far:
Don’t ask for a promotion until you have bagged a win worth putting on a resume.
Don’t ask for a promotion—ask what you need to do to get a promotion.
Switching jobs every 2 to 3 years is a great way to boost your pay.
Staying in one job for 7 to 10 years is a great way to build power—there is value in institutional knowledge.
Don’t network to get things from other people—network to give things to other people. Favors will come back to you.
Don’t accept promotions to management if you don’t want to be a boss. Ask for harder challenges and looser supervision instead.
You can work harder than you expect by taking an inventory of your life and deciding what you can do without for a few years.
Remember, crises are the best time to be young and ambitious—and everyone’s in crisis. Work hard. Solve problems. Buy the dip on society at large, so that you can name your price in 2035.