Asking for Career Help: What I Wish I'd Known

Transitioning from non-technical work to a technical career like software development is difficult. Getting help and advice shouldn’t be though. There are developers in every community who believe that a rising tide lifts all boats and want to help you lift your boat.

When you think of learning as a journey and attaining a developer job as a destination, this metaphor can be extended. Even with a rising tide, a boat needs direction and motivation. It’s easy to overcomplicate things for yourself and unintentionally make your journey more difficult.

Quite Difficult

A boat with sails but no motor or rudder, It could go far but only with a big push in the right direction.

Similarily to Tenderfoot in Pamela Vickers’ “Crossing the Canyon of Cognizance” presentation, you are standing on one side of what seems like an impossible to cross canyon, but you see someone like you on the other side. Maybe you can just ask them how they crossed and you can do the same.

“Hi. I have read your blog and noticed that you taught yourself programming. I am also teaching myself programming and would like to transition to a career in software development. Would you mind telling me how you got your first programming job?”

Maybe at the outset, this doesn’t look like a really big ask. This person is just asking for a little bit of information.

“Would you mind telling me how you got your first programming job?”

When I hear this question though, I hear “Just tell me the secret formula you used, so I can use it too.” Unfortunately there is no secret formula.

When I receive this question, I see two ways to answer it: a lengthy but accurate response or a short but sweet response. The lengthy but accurate response won’t be very helpful because the take away from that story is “be in the right place at the right time.”

I did have a little bit of experience with programming which may have given me an edge, but I also was looking for internships at a time when many others weren’t. The market I work in didn’t have any local code bootcamps when I started learning so I didn’t encounter groups of 20 cohorts graduating at the same time, all applying to the same positions.

The short but sweet response is that I applied for every job I thought I was qualified for, showed anyone who would look my small “portfolio”, and answered every single recruiter message no matter how shady it appeared. It’s not very accurate though because like I said before, timing was on my side. But more importantly, I had the help of a lot of kind people.

Now that you have this information, maybe you realize that my story (and most of those you might collect) doesn’t reveal a formula you can replicate exactly for exact results. You have more information, but it probably hasn’t made your transition to software developer much easier. Not to mention, it’s a bit taxing to write out everything that happened and explain why those things matter, so it’s not a great question if you want a timely answer.

What you probably wanted to learn was what specific things you could or should do to become a paid developer.


A boat with a motor but no rudder, It could go far but far in what direction?

After going to some meetups you finally met some of these kind developers who want to help, so why not “leverage your network” like people online are always recommending? That’s how most people get their jobs now, right?

“Hi. I see that AtlantasMostFunDevShop has a job opening. I’m really interested in working there, can you connect me with the correct person?”

This is definitely more specific. Narrowing your scope to a job available at my company is certainly a smaller set than all possible jobs. So simple, all I need to do is connect you with the correct person.

“can you connect me with the correct person?”

The correct person for what though? The correct person to tell you their experience in that job or team? The correct person to help you get an ‘in’? I’m really not sure who the correct person is for you but the intentional vagueness does make me suspect you’d like to bypass the traditional application process. I really want to help you, but sort of backdoor/under the table type things make me pretty uncomfortable and hesitant to help or expose my coworkers. If you’re looking to get more information about that role, just ask!

“Hi, I saw this job opening at your company and I’m really interested in learning more. Do you know someone on that team I could speak to to learn more about it?”


“Hi, I saw this job opening at your company and I’m really interested in learning more. Would you be interested in grabbing coffee to chat about AtlantasMostFunDevShop?”

Hey! I can definitely help you with that. By being explicit that you’re looking for more information and not a way to bypass the system, I’m comfortable introducing you to my coworkers because I know you won’t put them in a position of discomfort or pressure. By meeting my co-workers with the intent of discussing the role and seeing if you find common ground instead of “leveraging” them like a resource, you can expand your network of people interested in helping you.


This is a sailboat with a rudder but no motor, it has direction but only given the right wind.

You know that having a network of developers can help you, so you reach out to one who works at a company where you are interested in working:

“Hello, I was looking at AtlantasMostFunDevShop's website and came across this posting for a WorldsBestLanguage job. Can you tell me anything about the job?”

This is a little bit better, the question is referencing something specific but the question itself is very very broad.

“Can you tell me anything about the job?”

Dang, the answer to that could really be well anything. I know what I would want to know about the job. Do they value test driven development (not necessarily test first)? Are all members of the company treated with equal respect regardless of experience level or technical ability? Does the company value learning and give everyone space to learn and teach? I could list off all of the things that compelled me to take the job, but I don’t want to bore you with details, so I would probably provide a broad response to this broad question.

This might help you get an idea of why I chose to join this company, but you hopefully are looking for more specific, actionable information for yourself. If you’re thinking about applying for jobs and not looking for more specific and actionable information, I’d recommend reading through this presentation by Britni Alexander to help you firm up what your career goals are and what you’re looking for in a job.

If you’re looking for something specific though, why not just ask? You probably want to know if this job will be a good fit for your skill and experience level.

“Hello, I was looking at AtlantasMostFunDevShop's website and came across this posting for a WorldsBestLanguage job. Do you mind if I ask you a few questions? I noticed that the experience level is pretty ambiguous, do you know if they are considering junior level developers? I am still learning and studying a lot, are you given time at work on new skills? Is there a mentoring program at your company?”

Hey, I know the answers to some of those questions! I can definitely speak to my experience with those things you’re concerned about, and the things I don’t know are simple questions for me to find the answers to.


A boat with sails, motor and rudder. This boat has direction and its own source of motivation.

“Hey, I saw that AtlantasMostFunDevShop is hiring WorldsBestLanguage developers. I’ve been writing WorldsBestLanguage and really want to work on SpecificSoftwareOrCultureIssue, I was reading an article in Interesting Publication about it just the other day. If you didn’t read it, I recommend checking it out! Do any of the teams at AtlantasMostFunDevShop do anything like that?”

Hey there, this one is actually pretty great! You mentioned something specific you are interested in working and you’re excited about it. If my company isn’t working on that problem, I bet you I know someone at another company that is.

Let’s say we do work on SpecificSoftwareOrCultureIssue. I love how excited you are about it and how much information you gave me. It’d be really cool if you applied to work with us, and I’d definitely mention your interest in SpecificSoftwareOrCultureIssue when you do. Let me know if you’d like me to read over your cover letter or if you have any questions about the application or interview process, I’m here to help!

Letters to a Young Developer

This was part of a series called “Letters to a Young Developer” where I’ll share the great advice I got, or the advice I wish I’d gotten when I first started learning Ruby.

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