I’ve reached the point in my career and have enough gray hair that people sometimes ask me for career advice. Usually they are in tech, trying to make a transition into a different role, or are trying to get into tech. I do my best to answer these questions because it is obvious that they have experienced some sort of trauma and/or have run out of better options if they are at the point where they can look into the melancholy and barely obscured madness behind my eyes and think “This is someone who can help me.”

To save others from having to brave the same journey, here is a small FAQ that reflects the common themes of those discussions.

How do I get started in X?

You just do the thing and keep doing it until someone is willing to pay you money to do it.

You become a writer by writing.

You become an engineer by engineering.

Unless you need a license (*I* won’t judge how you learned to remove appendixes, but others might.), you just need to start doing the thing.

This is not the answer people want or are looking for. But it really is that simple. There are no shortcuts or lifehacks. Simple != easy and that sometimes makes our brains sad. I’m sorry.

What tech do I need to learn to do X?

There are admittedly different fundamentals required for different types of jobs, but if you’re asking about specific technologies the answer is that it doesn’t really matter.

Python or Ruby? Doesn’t matter.

AWS or Azure? If you can figure out one, you can figure out the other.

If you have a specific role in mind, do some research on the thematic pillars of that role and pick 1-2 pieces of tech in each pillar to focus on. Do not go down the rabbit hole of infinite research trying to decide on the perfect lineup of tech to learn. That’s not a thing. You’ll just delay doing anything useful.

There is one “trick” I recommend here. People have mixed opinions about certifications, but if you can use studying for a target certification as a learning path, go for it. It may focus you a bit.

When is it OK to list X on my resume?

Have you made a thing or two that worked using X and can speak about it in the appropriate context? OK then, go for it unless the job was explicitly defined by X, like “Unity Developer” or “AutoCAD Tech”. The ancillary stuff is fine to list if it is relevant to the role and you have actually used it.

Is X just a word you saw somewhere? Do not put it on your resume. I generally don’t delight in making people squirm in interviews, but I will create a “learning moment” that may be uncomfortable if I catch someone keyword stuffing.

How do I answer interview questions about things I haven’t done without lying?

I have never lied in a job interview. I have, however, re-framed my experience in the context of the job I was applying for.

When it comes to the actual interview where you’re asked “Have you done X using Y?” and the answer is “No”, try going with “I’ve done A using B which is very similar to Y” – shifting the focus to how you solved a similar problem rather than the specific one they asked about. Granted, you can’t pull this trick for every question without coming off as evasive, but it’s a legit tool.

It’s also OK to not volunteer unprompted caveats like “I’ve done X… but never in production.” They don’t need to know that. You aren’t marrying this person. Just say “Yes” and move on.

Nailing an interview is more about being able to sell yourself than proving what you know, with exception of coding interviews which are a crap shoot (I prefer take home exercises.). The “selling” part feels icky to a lot of us, but it shouldn’t. All you are saying is “I’m worth hiring and would or could be good at this.” not “I am the platonic ideal of a human.” Selling your value isn’t lying, it’s being honest about your worth, which may require you working on liking yourself.

If you don’t have *any* experience and have made it to the interview stage, the person interviewing you either knows that or is an idiot. You should be good in either case, although I would recommend not working for idiots. It is in your best interest to be honest (generally, but especially in this case) about your lack of experience (again, don’t volunteer answers to unasked questions) because it will be very easy to sniff out a lie – assuming you’re not with the idiot.

I feel like I’m under qualified for all the jobs I look at.

To be fair, this is a statement and not a question, but here’s the rub:

Don’t assume that everyone applying for or working in a job knows more or is more experienced than you.

“Think of how stupid the average person is, and realize half of them are stupider than that.” – George Carlin

Some of those stupid people have the job you want. They may have even got the job because of how oblivious they were to their own weaknesses and came off confident as fuck.

Regarding “job requirements”: ignore them past how they frame the nature of the role. In most cases they are an aspirational wish list that someone copy/pasted from someone else’s aspirational wish list. That folks often ask for more years of experience in a specific tech than the tech has existed is testament to the lack of thought that goes into most postings.

If you see a job description and immediately think “I’m qualified for this.” you are probably over-qualified or very senior and have an appropriate level of confidence.

When I write job descriptions I try to use the requirements to filter for “I need you to be somewhat familiar with this branch of tech.” vs. “I need someone with exactly 5 years of experience writing Terraform.”

On paper, I’ve never fully met the requirements for the roles I’ve been hired for. I don’t even have a college degree and sound like Hank the Cowdog when I talk. Don’t let the “requirements” stop you from applying for something.

I mean, they let me in. You’re probably way nicer than I am.

It says “senior”. I’m not a senior.

Again, not a question.

Here’s a secret. Job titles are bullshit. Ignore them.

Their functional purpose is almost entirely for creating pay bands. Just work hard, be kind, remove bottlenecks, and solve pain points.

Ignoring your title and the scope that it implies can carry your career a lot farther than trying to adhere to some rigid definition. Stretch your wings and get involved in whatever interesting work you come across. If you approach work that wouldn’t typically fit your title with humility and thoughtfulness, you will generally be welcome.

Summary: The stakes are low

If you’re reading this, it’s unlikely that you’re in a situation where getting a specific job is literally the difference between life or death. To paraphrase the mostly problematic founder of GoDaddy – No one is going to eat you if you fail.

Apply for roles that interest you. Pitch yourself with confidence. Learn something from every interview, whether you get the job or not.

And when you do get the job, reach a hand back down the ladder to help someone else up.

Photo by Andre Mouton on Unsplash