How to land your dream job, despite improper planning

The Plan Everyone Gave Me

Growing up, the path forward seemed obvious. Every adult in my life repeated the same formula:

Study hard and do well in high school
Go to college
Earn a degree
Get a job

Simple, right? Follow the steps, collect your reward.

So I followed the steps, and like I mentioned in my introduction, I failed — spectacularly, repeatedly, and in ways that should have derailed everything.

The problem wasn’t effort. The problem was that the plan is incomplete. It’s missing crucial steps, and nobody told me what they were until I’d already stumbled through a decade of unnecessary mistakes.

Here’s what I wish someone had explained to me at 17.

The Plan Is Backwards

The standard formula presents life as a sequence: high school leads to college, whcih leads to a degree, which leads to a job. Each step unlocks the next, like levels in a video game.

But this framing has a fatal flaw because it doesn’t tell you which job you’re aiming for.

Without knowing your destination, how can you possibly optimize the route? You can’t. You just default to “get good grades in everything” and hope it works out. For some people, it does. For the rest of us, we waste years preparing for a destination we never actually chose. As they say, “You can do everything right and still not win.”

The fix is simple but counterintuitive: start at the end and work backwards.

Instead of “do well in high school → figure out the rest later,” the actual sequence should be:

Identify a career direction (not a specific job, but a general field)
Research what credentials and skills that field actually requires
Choose education paths that build those specific skills
Focus your high school efforts on what actually matters for step 3

This sounds obvious when written out, but almost nobody does it because nobody tells you to. It also requires making decisions when you feel least qualified to make them.

“But I Don’t Know What I Want To Do”

This is the objection I hear most often, and it’s completely valid. How is a 16-year-old supposed to know what career they want?

Here’s the thing: you don’t need to know your exact career. You need to know your general category.

Most careers fall into a handful of buckets:

Trades (electrician, plumber, welder, HVAC, etc.)
Healthcare (doctor, nurse, technician, therapist, etc.)
Business/Finance (accounting, marketing, management, etc.)
Technology (software, IT, data, engineering, etc.)
Creative (design, writing, media, arts, etc.)
Education/Public Service (teaching, government, nonprofit, etc.)
Science/Research (laboratory work, academia, R&D, etc.)

You don’t need to know if you want to be a cardiac surgeon or a physical therapist. You just need to know if healthcare interests you more than technology, or if you’d rather work with your hands than sit at a desk. And remember, you can always jump to a different career path.

That level of self-knowledge is achievable at 16, especially if you’re intentional about exploring options.

How to Figure Out Your Category

Here’s a simple exercise I wish I’d done:

Step 1: Think about the last three times you lost track of time doing something. Not something you were supposed to do — something you chose to do. What were you doing?

Step 2: Think about the adults in your life whose jobs sound interesting when they describe them. What do those jobs have in common?

Step 3: What subjects in school feel like the least amount of work, even when they’re hard? Why do I enjoy those subjects? What career fields make use of my favorite aspects?”

Your answers won’t point to a specific job, but they’ll usually point toward a category. And a category is enough to start planning backwards.

I always enjoyed science classes, and physics spoke to me more than biology or chemistry. I found myself particularly interested in light, lenses, and lasers. My answer was to specialize in optics!

The College Decision Matrix

Once you know your general category, the college question gets much simpler, and the answer isn’t always “go to a four-year university.”

Here’s a decision framework that would have saved me years of confusion:

Path A: Skip Traditional College

Best for: Trades, some technology roles, entrepreneurship

If your target career is in the trades (ex. electrical, plumbing, welding, HVAC, construction), traditional college may be the wrong choice. Trade schools and apprenticeships get you earning faster, cost less, and provide more relevant training.

Similarly, some tech careers (particularly in software development) are increasingly accessible without degrees. Online bootcamps, self-study, and portfolio projects can be faster paths in.

The math: A plumber who starts an apprenticeship at 18 can be a licensed journeyman by 22, earning $60-80k with zero student debt. A college graduate at 22 is just starting their job search, often with $30-50k in loans.

Path B: Community College → Transfer

Best for: Anyone uncertain, anyone cost-conscious, anyone who struggled in high school

This path is criminally underrated. Community college lets you:

Figure out if you actually like your intended field before committing $100k
Complete general education requirements at 1/4 the cost
Build a college GPA from scratch (your high school grades matter less)
Transfer to a four-year school with junior standing
Allow you to dual credit — take a single class satisfying both high school and college courses at the same time

I actually did this, and saved myself time and money in the process. My shaky high school foundation meant I wasn’t ready for university-level coursework, and I paid the price in failed classes and damaged GPA.

Path C: Four-Year University

Best for: Careers requiring specific credentials (medicine, law, most engineering), research/academia, careers where school prestige matters

If you’re going the four-year route, which school matters more than most people admit, but in specific ways, because different schools are known for different things. State flagship universities are not interchangeable.

For example, when I was choosing schools in Kansas:

University of Kansas (KU): Strong medical school, good for pre-med, healthcare paths
Kansas State University (KSU): Strong engineering, biology, and agriculture programs

A student interested in medicine would be better served by KU. A student interested in engineering or veterinary science would be better served by KSU. Yet many students choose based on campus feel, sports teams, proximity to family, tradition, or where their friends choose to go.

How to research this:

Talk to people actually working in the field and ask where they’d go if they were starting over

Google “[your target career] best undergraduate programs”

Look at where professionals in your target field got their degrees (LinkedIn is useful for this)

Check if specific employers recruit from specific schools

The Maturity Variable Nobody Talks About

Here’s something that took me years to understand: the standard timeline isn’t right for everyone.

During my undergraduate years, I lived with three other physics majors. Two of us came straight from high school, but the other two had taken “time off” — one spent several years in a death metal band, another did four years in the military.

The difference was night and day.

The students who had taken time off knew exactly why they were there: they showed up to class prepared, they treated assignments like job deliverables, and they had figured out who they were and what they wanted before arriving. They were clearly focused on getting the best education they could.

Meanwhile, I treated college like an extension of high school. I assumed showing up was enough. I didn’t take it seriously because I didn’t have a clear picture of what I was building toward. I was following the script without understanding why. Many students fall into this trap, encouraged by sororities/fraternities, sports team enthusiasm, and other campus hijinks.

My GPA reflected my lack of focus. And my weak undergraduate performance absolutely affected my graduate school options — I ended up at a lower-ranked program than I might have otherwise.

When to Consider Taking Time Off

You might benefit from a gap year (or more) if:

You have no idea what field you’re interested in, even at the category level
You’re going to college because it’s expected, not because you have a goal
You struggled significantly with motivation in high school
You’ve never had a job, managed money, or lived with real responsibilities
You’re burned out and going through the motions
You’re honestly not read for a full-time 4-year commitment.

What to do during time off:

Work a real job. Any job. The point is experiencing responsibility and understanding what you don’t want to do forever.
Try things. Volunteer in different fields. Take community college classes in subjects that interest you. Shadow professionals.
Save money. Even a year of full-time work at modest wages can meaningfully reduce your future student debt.

The military and AmeriCorps can be excellent structured options that also provide education benefits.

High School: What Actually Matters

If you’re still in high school (or have kids who are), here’s what I’d prioritize knowing what I know now:

Things That Matter More Than People Let On:

Developing genuine skills. Can you write clearly? Can you do basic math without a calculator? Can you learn things on your own from books and videos? These fundamental abilities matter more than any specific class.

Building a track record. Anything where you stuck with something difficult over time and got better at it. Sports, music, robotics club, a part-time job, a personal project. Colleges and employers care about evidence that you can commit and improve.

Exploring career categories. Job shadows, informational interviews, summer programs, volunteer work. Anything that gives you data about what different careers actually look like day-to-day.

Things That Matter Less Than People Say:

Taking every available AP class. A few AP classes in subjects relevant to your intended path? Great. A schedule packed with AP classes that leaves you stressed, sleep-deprived, and with no time for exploration? Counterproductive.

Perfect grades in every subject. A student interested in engineering who gets an A in AP Physics and a B in AP Literature is in better shape than one who gets B’s in everything trying to be well-rounded.

Prestigious extracurriculars you don’t care about. Depth beats breadth. Being genuinely committed to one or two things you care about beats a resume padded with activities you joined for the bullet point.

The Revised Plan

Here’s what I’d tell my 17-year-old self:

Figure out your category. Not your specific job—just your general direction. Use the exercises above.
Research backwards. What do people in that field actually do? What credentials do they have? What do hiring managers look for? Talk to real people, not just guidance counselors.
Choose your education path intentionally. Not all paths go through four-year universities. Pick the route that actually leads where you want to go.
If you’re not ready, wait. There’s no prize for finishing fastest. A year or two of working and exploring can be worth more than four years of unfocused college.
Once you’re in, treat it like a job. You’re there to build specific skills and credentials for a specific purpose. Every class, every project, every relationship should connect to that purpose.
Plan for the long game. Your first job isn’t your last job. Optimize for learning and options, not just starting salary.

The plan everyone gave me wasn’t wrong—it was just incomplete. It assumed I knew where I was going and just needed to walk there. The truth is, figuring out the destination is the hardest and most important part.

Start there. The rest gets easier.

Next up: How to build a successful side hustle, despite failing

Previously: How to boost your income despite poor grades