Tech career thoughts

Once upon a time last year

In the spring of 2025, I had a sense that it was time for a change in my career. I had already experienced two layoffs back to back, and my instincts were telling me to do what I can to avoid a third. So I started to look for a new job.

I spent about 5 months applying, interviewing, and getting rejected. In some cases, my application was either completely ignored or immediately denied. In others, I passed the initial screening but then failed the “technical” interview portion, which generally consisted of a “leetcode” style interview (see my thoughts on this below).

I went the distance with several companies, completed take home projects, did full interview panels conducted over multiple days, but they all ended up passing as well.

I tried not to take it personally, and reminded myself that this is just part of the game. I tried to keep in mind that times were tough for everybody, and that I was in very privileged place, especially since I was still employed, and also that previously things had worked out marvelously for me. That said, I was feeling quite anxious about the future.

A quick and dirty analysis of my email over this time period shows the following:

- applications: 67
- explicit rejections: 21
- ghosted: 45
- offers: 1

Not captured here are the dozens of calls with recruiters, LinkedIn messages to colleagues and connections, and time spent crafting cover letters…

I am very grateful for my new position.

High minded punditry

The point of this post isn’t to pontificate on the industry or complain about things I have no control over. I only want to share my experience, and describe the things that worked for me and the things that didn’t.

Clearly, given the wild ratio of success to failure exhibited above, I am not a particularly authoritative source on this topic. Below are things that helped me through my numerous job hunts, and perhaps they will be useful to someone else (or myself in the future if I’m in this position again).

Practical Principles

Stay organized

First and foremost, I need to write things down, and in such a way that I can track and reference where I am in the process with each company. For me, a board like Trello/Asana/Linear whatever works best, but if you love a spreadsheet or a text document, then just maintain it. Things useful to track are:

• The name of the company
• The link to job description
• If you were referred by someone, their name
• How you found the position (job board, blog post, whatnot)
• Who initiated contact (recruiter reached out? applied via website?)
• Current phase of process, whose court is the ball in?
• Names and positions of people you’ve been in touch with

These are important because:

• When talking to your counterparts and you know these things, you come across as a professional
• If they haven’t gotten back to you within some reasonable time frame, follow up
• Thank people who refer you even if you don’t end up getting the position

Do your homework

Different companies make use of different assessment methods in their hiring processes, but ultimately their goal is the same: to find the “best” person for the job.

For technical positions, fit is often evaluated across two axes:

• Hard skills: your ability to solve technical problems in a specific domain.
• Soft skills: how you communicate, collaborate, and work with others.

For better or for worse, companies have historically indexed heavily on hard skills when considering applicants. This means that you might be an outstanding ebullient charmer, with a solid technical background, but haven’t yet accomplished any very impressive projects; someone who has a track record as a tremendous contributor will get the job, even if they are abrasive and even offputting.

That said, one thing that is in your control is how much work you put into the preparation for each phase of the process. Read about the company, its mission, its stated values. Read up on the competitive landscape and significant milestones in the company’s evolution so far. Read the bio of the person interviewing you.

Read the documentation for their products, or see if they have any open source projects published and see what you can learn about them from those. All of this information can be useful in the course of your conversations with them, and it will also be a good indicator how much you care to actually apply or work with them.

A side note on Data Structures and Algorithms interviews

Much has been said on the topic of the effectiveness of DSA interviews, and the discussion seems to range between two extremes:

• DSA interviews are meaningless and useless; we never use them in our jobs, these are solved problems, they are not a good measure of the quality of a software developer/engineer.
• DSA interviews are the best objective qualitative indicator we have of a person’s ability to solve problems with software. They provide strong signal for a person’s ability to apply computer science principles toward real world problems we encounter daily as engineers.

Clearly neither of these polarities can be completely correct. As I see it DSA interviews de-facto matter. I find that the industry is wildly biased toward people with a computer science background. It might make intuitive sense, but falls apart quite quickly when looking closely at what types of problems the majority of engineers are actually dealing with on a daily basis. To me, these tests seem to be as effective as other sorts of standardized tests that society has accepted as common practice despite no evidence linking high scores to successful outcomes (see IQ, SAT, etc.).

I don’t really have a great solution or alternative to propose, I’ll just note my own discontent with the situation, which stems in no small part from my own limitations on this front. If it serves you as a means to get the job you want have at it. The more you do, the better you’ll get at it. Just don’t think it means anything about you if it’s hard for you at first.

Be empathetic, be real

If possible, try to imagine your candidacy for the position through their eyes, and ask questions about what type of work needs to get done, and how you in particular can help them achieve their goals.

Be honest with yourself about why you are applying to this particular job. If it is because the pay is good and you like nothing else about it, that’s fine, just be real with yourself about it. You don’t have to necessarily disclose your exact motivation, but it is good to deliver a message you are somewhat aligned with, as inevitably you will be asked why you want the job. People can generally detect a lack of authenticity.

Don’t give up

My first job in tech was in the year 1999. I am writing this in 2026, and started my job last year at company number 15. This has meant more interviews than I would ever care to count over the years.

I’ve also been on the other side and conducted probably over a hundred interviews both as a hiring manager and as an engineer. All this is to say is that sometimes it’s just not a good fit. Sometimes a company will also simply not be able to assess the fit very well. Sometimes they drop the ball. Sometimes the candidate drops the ball. I know I have.

It’s a big world out there. Don’t be shy to leverage your network. See a company that’s hiring? Check LinkedIn to see if you know anyone there who can put in a word for you and make a referral. Feeling shy? Embrace the awkward and move on. It can do wonders to differentiate your application, especially in a competitive market.

I’ve witnessed first hand several economic ebbs and flows in my career so far: the dot com boom and bust, the 2008 financial crisis and subsequent recession, crypto hype cycles, COVID-19, and whatever we’re calling the current calamitous gloom.

I am thankful to have gotten through most of it unscathed (not to say oblivious), but I’ve also had to scramble a few times, and I’ve probably received many hundreds of rejections. Some job hunts resulted in multiple offers, and I felt very confident and proud. Some yielded nothing, and I had to stay for another year at a job I hated.

Work is important, and in some cases even tied to our survival, however, it has served me to resist the tendency to equate my ability to earn a salary with my own personal self-worth. This hands over more power to capital, which already enjoys enough leverage.

All this is to say, just keep chipping away. If you’re not applying, study. If you’re not getting responses, broaden your criteria. Network with people, do practice calls, find someone who has been through this and talk to them, find a mentor. Try to find a local group of like minded folks to talk through your experiences together.

Don’t give up!

Okay fine, “AI”

I have thoughts on this, but this post is long enough as is. All I know is that if it serves you, use the tools. LLMs can be useful to do things like:

• Punch up your CV
• Take your punched up CV and a job description, and write a cover letter using the company’s values as a reference framework
• Formulate and walk through possible interview questions
• Walking through coding problem solutions and explaining systems and principles

Resist anxiety related to the machines replacing you. As software engineers, “AI” can augment our productivity, but it ultimately doesn’t do much of anything without us guiding it and checking its work. I like to think that “AI” assisted coding is to writing code by hand, what a drill is to a brace. Power tools have unlocked tremendous capabilities across industries, but ultimately both of these make holes. Deciding where the holes go and why is still our choice, whether we’re programming a CNC or cranking on the handle. A 3d printer is not a replicator, and never will be.

I can’t say “don’t believe the hype”, because you should believe what you want, and what you understand to be real. I will, however, advocate for us to make choices from a place of hope rather than out of fear. We can and certainly should be skeptical of who is served by the hype.