My Software Career So Far: An Unapologetic Recap

This content originally appeared on DEV Community and was authored by Anonymous Dev

Contents

This blog will be split into the following sections:

• Foreword: A Note from the Author
• Chapter 1: Over-Romanticizing Software Engineering
• Chapter 2: Education - a Quick Recap
• Chapter 3: The Internship Experience
• Chapter 4: First Role at Company #1
• Chapter 5: Stagnation & Leaving Company #1
• Chapter 6: Moving to Company #2
• Chapter 7: Experience, Red Flags & the Exit from Company #2
• Chapter 8: Navigating Interview Hell
• Chapter 9: Company #3 & Beyond
• Afterword: The End

Foreword: A Note from the Author ✍️

In the beginning, when I first sat down to write this little blog, I thought to myself how far back do I want my story to begin? The start of my first job? Second job? College? Senior high? Elementary school? And then I realised that I was asking the wrong question. I should have been asking why am I writing this article?

Well, the purpose of me writing this article isn't really to go viral and get thousands of views, reposts, shares or whatever. The original purpose was simply to act as a personal journal entry for myself.

But then I thought, hey there might be a chance that someone else will benefit from reading the things I have to say here - that someone out there might be able to relate to the angst of being young, the challenges of starting out as a software engineer in 2025, the fear of stagnating in one's career, and allllll the other things I'm gonna yap about here.

However, since this was originally intended to be more of a personal blog, it might be a good chance for me to reflect on my life as a whole and who knows, it might even help me to understand more about myself: why I am the way I am, why I've done the things I've done, why I think the way that I think. But fear not, I'll do my best to leave out the boring parts 😛.

So, without further ado, here we go!

Chapter 1: Over-Romanticizing Software Engineering 🌹

For as long as I can remember I always thought that the idea of building something out of nothing was the coolest thing ever. Just you, your laptop, several cans of the most lethal energy drink money could buy, an idea, and a belief that you could change the world (or at least build something moderately cool 😎).

This and other similar trains of thought, led me to over-romanticize what it was to be a software engineer (SWE). And this eventually led me to feeling anxious and miserable, crippled with imposter syndrome, and ultimately burning myself out. Was it worth it? I guess we'll find out.

Hi, my name's Anonymous. I'm 25 years old and I'm a software engineer at a tech startup. To be honest, I wasn't always comfortable calling myself a software engineer. Whenever people asked me what I did for a living, I usually just told them that I was in tech.

I didn't really like to specify that I was a SWE because, quite frankly, I didn't think that I was deserving of the title. I thought that being a software engineer was all that. That SWEs were superheroes of some sort, the cream of the crop, the best of the best. I thought SWEs were the coolest people ever (and to be honest, I still think we're pretty cool 😎 but I prefer not to glorify it anymore).

Chapter 2: Education and a Quick Recap 🎓

By the time I finished senior high, I was feeling pretty lost and not sure what to do in college. Having no one older to talk to about this stuff, I had to make the decision on my own. I eventually ended up choosing Engineering from a process of elimination of things that I didn't want to do, instead of "following my passion" or whatever else people did.

Although I ended up deciding to not pursue engineering, one positive of my time in engineering was an elective I chose which happened to be a Computer Science (CS) subject which I absolutely adored. This course was the main reason I decided to pursue a degree in CS.

Chapter 3: The Internship Experience 🐣

I started at my first role in industry as an intern. The role I applied for was a Cloud Engineer (intern). However, I found myself in a very technical SWE role. And my college degree did not prepare me for this. I was feeling extremely out of my depth.

There were a couple of interns in the team who started 6 months before me that were running circles around me (which made me realise that these supposedly “less prestigious” colleges actually prepared their students for working in the real world a lot better than my college ever did, leaving me feeling stupid, betrayed, and jealous of my fellow intern colleagues).

To be honest, I've never admitted this to anyone, but the reason that I did what I was about to do next was because I couldn't keep up with the work that I was being given at the time. It was my first real job in tech. I was still learning what Agile was. I was still figuring out what all the roles in the team were responsible for. I was still figuring out how to navigate corporate life during COVID where I couldn't meet my team members in-person. I was still figuring out how to navigate the team's gigantic codebases.

Although nothing was expected of me as an intern, I had expectations of myself. And I couldn't live up to those expectations. I didn't know how to help myself. And for the first time in a long time, I felt completely hopeless. Like I had failed.

I was too scared to ask for help for the 1000th time. Not even knowing basic testing frameworks like jest. Not knowing my way around macOS/Linux and the terminal. Not knowing the first thing about how to read through and understand a codebase, let alone the seemingly endless tech terminology, concepts, frameworks (and back then we didn't have ChatGPT to explain this stuff to us😭).

And so I'm not proud of what I did next, but at the same time, I didn't know what else to do.

I asked the HR team that was handling all the tech interns to swap me into a more cloud engineering role like the job description originally advertised. Although I did this for a few reasons including: originally signing up to be a cloud engineer and wanting to go back and explore that stream, liking the sound of being a cloud engineer because cloud was all the hype at the time (and still kinda is) - upon reflection, the main reason I left was because I was struggling to keep up with the team and the work that they did.

This ended up being a horrible decision because the next team I got put in was awful. I mean the people were nice but the work they were doing was completely dead/boring (at least to me) and I feel like it had no career progression.

Upon reflection, I should have spent more time trying to understand what I was doing in my first team. Instead, I was using my idle time during my internship, studying for college, trying to get good grades - which, looking back, was definitely a waste of time. If I had instead used that extra time to actually study for what I was doing at work, or building side projects, that would have been a much more productive use of my time.

For graduate roles, I landed 2 companies (one of which was the current company I was interning at) after which I stopped applying altogether because of my hectic schedule and burnout. In the end, I decided to stay at my current company at the time partly due to laziness “it was easier to stay where I was” which was a bad decision.

Chapter 4: First Role at Company #1 🏗️

I won't get too deep into it, but my first rotation was pure hell (iykyk)

My second rotation was in the cloud domain. I considered myself fortunate because it was as close to a SWE team in the cloud/Platforms domain as one could get (other teams in the domain were mostly managing infrastructure, vendor products, and onboarding internal customers onto cloud). From my point of view, this meant getting the best of both worlds (cloud/software) which was a big plus because at this point in time, I was still tossing up between cloud engineering vs software engineering.

Although I worked in the cloud every day, across both AWS and Azure, and developing applications I wouldn't say it was your traditional software engineering team. And the applications we worked on weren't exactly traditional either. Retrospectively, I would say that they were more like applications that were based on automating cloud infrastructure - that's the best way that I can put it.

But no, there was no frontend, no APIs, no databases that held any useful/production-scale data. And at the start I didn't really mind this at all.

However, after I matured in the team (and after learning a lot 🙂) which meant: being familiar with the team's processes, applications, scope of work, team members, roles, domain/space - I think the fact that I wasn't in a traditional SWE team, working on external-facing traditional applications left me feeling like a fraud/imposter. But hey, at least I started to know more and more that I wanted to do traditional SWE, I just hadn't fully convinced myself yet.

Chapter 5: Stagnation & Leaving Company #1 📉

I rolled off at Company #1 as a mid-level engineer. And just to be clear, I'm telling this part of the story not to shit on anyone, but to explain why I felt like I needed to leave. Also I don't know how to write this in a way that doesn't make me sound cocky or egotistical, so if it comes across that way I sincerely apologise, it's hard to convey things when writing isn't one of your natural talents. Anyways, let's continue.

When I looked at some of the senior engineers in my team it was very apparent to me that, compared to them, I was adding more value to the team. In my eyes, I was doing more work than them, in a shorter amount of time, at a higher quality, whilst maintaining better communication, writing proper unit tests, writing good documentation (which no one in the team seemed to ever actually do) and contributing more consistently in team meetings (not just having my cam off and going for walks in the park lmfao) whilst getting paid less.

Don't get me wrong, some team members were clearly more senior than myself, not only in their tenure at the company, but also in their skillset and experience. Just to be clear, these are not the engineers that I'm talking about.

Anyways, about 6 months after I had rolled off, I was kind of feeling a bit stuck and bored with my current role and felt like I may want to explore something else. So I was casually browsing other job opportunities, I even applied to some, but not seriously I said to myself. I was reasonably comfortable in my current team and didn't really see a compelling reason why I should leave other than that I was getting bored.

During one of my 1-1s with my manager, I raised the idea of getting promoted. This was partly due to the aforementioned reasons, but also because I felt like I deserved it. Plus I felt that I had a bit of leverage tucked up my sleeve due to our most senior engineer leaving recently (special shoutout to him btw, he's goated and will leave an everlasting positive impact on me).

Yes I know it was very eager of me since I had literally only just become mid-level engineer and now not even 6 months later I'm asking to be promoted to senior. But hey what can I say, I felt like I deserved it :') Anyways, the conversation with my manager was quite positive. He took it pretty well and said that I was “definitely on the right track to getting promoted soon”.

What did “soon” mean? I didn't get an clear answer at the time, but I was satisfied enough with “soon”. And this conversation cleared my mind of any thoughts of leaving Company #1 because I was surely going to get promoted soon right?

A side note: My manager

I would consider my manager at the time to be quite charismatic, as in he knew his way around words. I suppose to get to his position, one would need to be able to have some sort of persuasive prowess.

I'm leaving this note here because I feel like I did not convey well enough that in all my conversations with my manager, at the end of every conversation, I was always left feeling good, and very convinced that I was going to get promoted (when in reality this was not the case).

My manager also recommended me to get an AWS certification to boost my qualifications. He said that it would help him to build a case to the higher-ups for my promotion.

Anyways, around 3 months after that initial conversation, I had gotten my AWS Solutions Architect - Associate certification and during my next 1-1 with my manager I told him that I got my certification and asked him about the prospects of getting promoted now.

This time he approached the conversation from a different angle.

He asked my why I felt the need to get promoted. He asked me if it was the money and he told me I shouldn't look at others in the team and compare myself to them because how others performed was irrelevant. And so I told him quite frankly that I felt like I deserved it due to both the quantity and quality of work that I was outputting.

He went on to give me a 20 minute explanation about why he couldn't promote me. He mentioned things like: “it's not up to me”, “it's not in the budget”, “the tech industry is in a very bad place right now”, “you're lucky to just have a job in the current state of tech”, “we have a hiring freeze right now”, "the company's current strategy involves a lot of hiring offshore" “it's been less than 1 year since you rolled off as a mid-level engineer” and a bunch of other reasons that flew right over my head because all I heard was “no”.

I was frustrated. And he might've noticed.

At the end he said something along the lines of “Look I can't promote you now, but at the end of 6 months, I can look to review your current salary and give you a raise”. And I was like hell yeah I don't really care about the position title - as long as I was getting compensated what I felt I was worth. And once again, this conversation cleared my mind of any thoughts of leaving because I was surely going to get a raise soon.

A side note: Rat story

In the 1950s a scientist and graduate of Harvard, Curt Richter, performed an experiment. He put a rat into a jar filled with water. The rat swam and swam and after a few minutes of swimming eventually gave up and drowned. Next he repeated the experiment, but just before the rat was about to give up and drown, he saved the rat, pat it dry, gave it some time to breathe, and threw it back in the jar. The rat continued to swim for 60 hours before drowning.

I don't know what you took out of this story. If you're an optimist, maybe it was something about the beauty of hope. Personally, I took it to mean that if you give someone a crumb of hope, they will cling onto it for dear life. They will stay longer than they were ever going to stay because hope was given to them.

I felt like I was the rat and my manager was the scientist, just stringing me along, giving me tiny crumbs of hope, trying to take as much from me as possible whilst paying me as little as possible. Taking advantage of the fact that I was early on in my career. Taking advantage of the fact that the tech industry was not in a good state. Taking advantage of me, or at least that's how I felt (it could have just been all in my head lmao).

But anyways, that my friends, is why I decided to leave Company #1

Chapter 6: Moving to Company #2 📦

In the month or two after my manager at Company #1 told me that there would be yet another delay in my promotion/raise, I decided to look around for other jobs. Nothing too serious, but I applied here and there just to get a general feel of the market and possibly try to understand where I stood and the type of compensation I could fetch with my current skills and level of experience in industry.

To be honest, none of my applications never really got past the initial resume screening stage. But I told myself that I was okay with this because the tech industry was in a horrible market and I wasn't really applying seriously anyways.

Upon reflection, this was a coping mechanism for one of my deepest fears. That I wasn't good enough. That I wasn't experienced enough. That I didn't have the skills required to land another job.

Anyways, little did I know that my “casual” applying would soon come to an end. A recruiter had messaged me on LinkedIn with one of those generic LinkedIn messages:

Example

Hi Anonymous Dev,

Company #2 is currently recruiting for the role of Platform Engineer in the XYZ Domain. Looking at your profile, we think you'd be a great fit. If you are interested in the role, please get back to me with your resume.

Sincerely,

Recruiter

I applied for the role and after 2 rounds of interviews and 1 round of LeetCode I managed to secure it. Accepting it was another bad decision.

Ignoring red flags

When I got the call for the quick phone-screening interview from the recruiter, he actually mentioned to me that this role was probably going to be less coding than what I'm used to 🚩 and he even asked if I was okay with that. I said yes 🤦🏻‍♂️.

I was ecstatic. I couldn't wait to rub it in my manager's face at Company #1. I couldn't wait to see the look on his face as I told him I was leaving.

Chapter 7: Experience, Red Flags & the Exit from Company #2 🚩

My first week at Company #2, I did fuck all and honestly this made me super anxious and worried that I was in a dead-end job with no growth trajectory. And I don't think I was wrong. The next week, things picked up a bit, but not in a good way.

The work that I got assigned included: writing emails, writing documentation, contacting internal teams, contacting external vendors, and research & investigation into pointless stuff. I was an “engineer” by title, but I was doing the least engineer type shit. It was only 2 weeks in, but I already knew that I needed to leave.

You know how they say when someone ends a relationship ends, to the person being broken up with, it seemingly comes out of the blue, but for the person doing the breaking up, it had probably been months or even years in the making?

They just needed a catalyst, something to push them over the edge. Well this is what my conversation with a former colleague was for me. It was the thing that made me realise that what I really wanted to do with my career.

Initially we were just chatting about life, and catching each other up with what had been going on since we last saw each other. Then we got to chatting about each others' career aspirations and she was telling me how much she initially loved her team and the work that she did, but now she was feeling like she had learned everything there was to learn in her team, and that she was beginning to stagnate.

For some context, she was a software engineer working to develop backend microservices, building customer facing and production-grade applications. And I can't pinpoint exactly where it was in the conversation, but somewhere along the way, I realised that that was what exactly what I wanted to do. To build apps, to develop features, to design complex software architecture, and be a part of abstract and philosophical conversations about software.

To be honest, I think this is what I wanted to do for a long time now, but this was the first time that I admitted it to myself and that was a scary thing. It was scary because, after I admitted it to myself, I opened myself up to disappointment. Disappointment of never achieving it, destined to becoming a hollow shell of myself with broken hopes and dreams. A sad human that was never able to achieve his goals and get to where he wanted to be. I think deep down this is what I have been most scared of for the past 2-3 years. And I guess my internal logic went something like if I never admit to myself that this is what I truly wanted to do, then I would never have to face the disappointment of never reaching my goals.

Internal Applications

I'll keep this section short, mostly because I simply can't be bothered recalling everything that happened. But basically, it ended with me having a conversation with my new manager at Company #2 and basically he soft-threatened me, in that oily corporate double-speak, saying that if I were to apply internally, he had it within his power to prevent me from leaving the team.

So yeah I guess I hit a dead end or at least I wasn't willing to go through the effort of applying internally until I had exhausted all my options externally.

External Applications

After accepting my fate that I wasn't going to be able to make an internal move any time soon, I decided to look elsewhere. I started doing what I wanted to do the least. I began applying to roles externally. And seriously this time. I made a routine of it. Every Sunday I would dedicate a couple of hours.

In the beginning, this was mostly polishing up my resume, updating my LinkedIn, writing a generic cover letter, procrastinating. After I had done all the preparation I felt like I needed to do, there was only one thing left to do - begin applying.

If you hadn't gathered already, this was the part that I was dreading the most, applying with the hope that I would actually get a role, with the hope that I would actually hear back, with the hope that somehow my resume would stand out among the sea of AI-generated resumes that were crafted specifically to beat companies' ATS (application tracking systems).

But alas, I applied. I spam applied. Every Sunday I would apply to anywhere between 10 and 20 different companies. Over the span of about 6 weeks, I applied to 80+ companies. Out of these 80+ applications, 60+ of them came back with rejection emails and the remaining I never even heard back from.

At this point in time, things were picking up a bit at Company #2 and I was finding myself more busy at work. This, coupled with being beaten down from rejection after rejection from every company I was applying to made me feel like I needed to take a break and so I decided to give myself exactly one week of relaxing and self-loathing :')

But good things never last I guess as I got a call back from 3 companies in 1 week.

A side note: A letter to those that are burnt out

To anyone reading this that's going through a tough time with job applications,

I just wanted to say - I feel you. I'm not going to say that for sure that it gets better or that you will definitely get a job (because I don't know your specific set of circumstances). I feel the struggle that you're currently going through: the tens if not hundreds of applications you've submitted, the tens if not hundreds of rejection emails that you've had to read (without even making it past the initial resume screening stage), the endless interview prep that you're doing, the feeling of not knowing what to do next, the endless upskilling, the feeling of hopelessness. I feel you. And I'm sorry that you're going through such a rough time. And I really really do hope that it gets better for you <3

Chapter 8: Navigating Interview Hell 🔥

Finally, I got what I was praying for all this time. I had received calls back from 3 companies letting me know that I had progressed to the next stage in my applications. I considered this both a blessing and a curse. A blessing in that I got calls back from 3 companies. A curse in that I had to sit through interviews with 3 different companies in such a short time span.

Long story short, I somehow ended up getting offers from each of the 3 companies and ended up choosing Company #3 based on a number of different factors including potential career growth, salary, and job stability among various other things

Chapter 9: Company #3 and Beyond 🚀

So, what now?

Well to be completely honest, I don't know.

For the past 2 years (it's honestly felt like much longer), I've been studying at least 12 hours a week, without fail - only taking one break a year for a yearly holiday with my partner. I've stayed consistent through the hard days and on the good days/weeks I have often exceeded my self-set 12 hours of study. And now, I almost don't know what else to do other than study and stay productive.

For the longest time, I've had the fear that if I stop now, I'll fall behind. That I'll fall behind and I won't be able to catch up. I've heard 100 times that “comparison is the thief of joy” that “we all have our own journeys” and that “we shouldn't compare ourselves to others”. But that's much easier said than done (at least for me).

And maybe this fear has been my main drive to work hard. But when I say this aloud it feels wrong. Doesn't it? Shouldn't it be that anyone's main drive to do something is because they want to, not because they feel like they are pressured or have to.

Drive should come from a place of passion, not fear, right? But also what if losing this fear means abandoning my drive to succeed? Maybe I need this fear to save me from complacency. Or maybe it's time to turn a new chapter in my life. I'm still not sure which one it is. In fact, it might be (and most likely is) a hybrid approach that combines both of these to strike some sort of healthy in-between?

Well one thing I do know is that I want to enjoy my life.

I want to be able to find joy in the simple things in life like: going for walks on a nice day ☀️ without feeling guilty for not spending that time being productive, spending time with my beautiful partner ❤️ and spoiling her as much as possible, spending time with my friends on weekends, enjoying brunch/coffee 🥐 in cute cafés ☕️, discovering / doing fun & novel things 📒, discovering myself, learning how to love myself 🧘🏻, going to the movies 🍿, explore new hobbies 🛹, and find what I actually want to be doing in my spare time 🙌🏻 (which is hopefully something that brings me joy).

I want to start romanticising my entire life, not just my work/career.

Honestly, I still probably want to be building things and learning on the side just because that's who I am as a person and I don't think that'll change in the foreseeable future. However, I hope to do it because I want to, not because I feel like I have to.

Conclusion: What have I learned and what do I still need to figure out?

I'd say that I've learned a lot about myself over these past few years. For the longest time, I've said that I don't really know what I want to do with my life and my career. And although I'm still not quite there yet, I think I have a much better grasp of the direction in which I want to take my life and career. And more importantly, I now believe that I have the tools, knowledge, and experience necessary to navigate my life.

I want to stress that this doesn't mean I know everything or can do everything - in fact, it means I know just barely enough to move forward without fumbling at every possible step.

Have you ever started to learn something new, and you quickly find yourself feeling overwhelmed? A large part of that is most likely because, at that point, you don't even know what you don't know - and that's a scary feeling. Once you start to navigate the waters a bit, the path begins to become clearer and the fog begins to dissipate. I feel like that is finally starting to happen for me now.

I've also learned that I'm not willing to give my dreams up for money. Once upon a time, I was offered a (bad) role for some extra money (about ~$50k more than I was earning at the time), and I was really proud of myself for declining the offer in pursuit of something that was more aligned to my goals. However, I was not very proud of myself for accepting the offer I got at Company #2 despite all of the red flags.

I feel like I've also gained a lot of confidence in myself, my skills, competencies, my ability to interview, etc. My self esteem has improved too.

Does this now mean that I have it all figured out? No!

I still need to figure out what I really want in life. I still need to figure out what's important to me, what I want to prioritize. We only have so much time and energy. We shouldn't waste it on things that don't matter to us.

I still need to figure out how far up the ladder I want to climb before settling/getting comfortable (staff engineer/principal engineer/distinguished engineer?). I also still need to figure out when I want to retire and what I want to be doing in my retirement/semi-retirement.

But as I mentioned before I feel like I now have the tools, experience, and knowledge to navigate all these spiky questions in the future. And honestly, this alone has been bringing me a lot of peace.

A side note: Cognitive Dissonance

I wanted to mention that for the longest time, I had an internal conflict with who I was, who I wanted to be, and who I told people I was. I was enough of a SWE in that I could build things, write decent code, and get projects done - but not enough that I felt I truly belonged in that title.

And so I guess I fixed the problem - not by changing the way I framed it, but by actually solving the problem. I expressed this thought to someone in my life recently. My concern was that because I had not changed my view/framing of the problem, that it somehow would pop up in the future.

They said something which stuck with me. It was something along the lines of: "all the reframing in the world isn't going to fix something that's fundamentally broken, life is always going to be a bit of fixing the things you can fix and trying to reframe in order to soften the things you can't. If you're sitting in a vat of acid, you can reframe all you want but you're still going to burn no matter how much you convince yourself that it's fine"

Afterword: The End

This is usually where writers say something like “if you've made it this far thank you for reading!”. I won't say that because this was supposed to be a blog for myself.

But I did want to end this blog by recounting a recent experience I had. I just wanted to preface this short story with the fact that I'm currently an atheist and I don't think that that will change in the foreseeable future.

I recently went to church for the first time with a friend of mine and during the service, the pastor invited everyone to come and write down a problem/struggle that we were currently facing on a very large piece of paper on the ground - and that if we did so, our prayers would be heard and answered by God.

In the beginning, only one or two people came down to write something which is basically what I expected. Personally, I was too shy to go down to write something (maybe because it was my first time). I assumed everyone else was also shy. Or maybe no one else had anything to write because they just didn't have any problems in their lives.

But after a couple of minutes, more and more people went down to write something. In the end, so many people went down that they had to form multiple lines. Overall, probably more than half of the room went down to write something.

And in that moment, I felt like I wasn't alone in my struggles over the past few months (if not years). All my feelings of sadness, stress, anxiety, utter hopelessness felt valid. For some strange reason, I found a sort of peace in knowing that everyone was also dealing with their own problems, and that it's extremely normal and extremely human to not be okay all the time.

So, if you're someone who's going through a rough time right now, whether that be from: work, school/uni, relationships, health, or anything that life has thrown your way, from the bottom of my heart, I wish you the best.

One thing that I've come to realise recently is that everyone is always fighting their own demons. And so whatever it is you're going through (no matter how big or how small) - I sincerely hope you make it out ❤️

This content originally appeared on DEV Community and was authored by Anonymous Dev