3 Signs it might be time leave your Engineering Job

6 min readJun 10, 2022

Tech moves fast… people, even faster. I have worked at 4 companies in 4 years in a wide range of Software Development positions. And throughout that time I found a few common things that always led me to the conclusion that it was time to go.

1. There is no mystery/challenge

I find that I get bored when I know exactly what to expect or exactly how to solve a problem as soon as it’s presented to me. This usually does not happen when you first start a job or even after a few months in because everything is still so fresh, you are learning the ropes, getting used to the people, etc. After a while though, that “newness” starts to wear off and you may find that you get to a point where literally nothing surprises you at work anymore. You fall into the same routine of fixing bugs, running some random A/B test on a button or building the next feature thats going to 10x the company but in reality, it turns out to be a failure.

The root of this issue I believe, is mainly two things. The work you are doing is not challenging enough and you are actively choosing to stay in your comfort zone. DO NOT SETTLE. Settling is the worst thing you can do. Sure, will you collect your paycheck every two weeks and pay the bills? Definitely. But are you going to be fulfilled and happy everyday you wake up? No. The problem with working when you are not challenged at work means that work becomes just that, work. This can lead to really long days at work and a sense of dread when you wake up every morning knowing nothing is going to intellectually stimulate you. So, if this happens consider stepping out of your comfort zone or start job hunting for something you think will excite you more than your current gig.

2. Upper Management seems disconnected from the problems of the business and/or are making big strategic mistakes

This one is a little tricky but can be spotted in a variety of ways. Here are just a few red flags to look out for.

Reorgs occur frequently

Don’t get me wrong a company going through a reorg is a pretty normal occurrence. But, if a company is going through multiple reorgs in a short span of time, that is not so normal. It is a sign that the leadership team hasn’t figured out exactly what works best for the company to operate at maximum efficiency. While it is nice that they are attempting to find that solution, reorgs come with consequences like teams being split up, projects may be scrapped, etc. This turmoil can make the work environment super stressful and is not fun to be a part of, trust me.

Projects are being killed off/deprioritized

This one is pretty clear. If you notice projects around you being deprioritized or just completely halted because they were deemed failures, it’s a red flag. This is especially true if the projects life span was only a few months to begin with. Again, I want to pause and take note that it is not always a bad thing for a project to be deprioritized but everything in moderation. If a project is halted because there are clear metrics to indicate the project is not performing as it was expected to thats one thing. But, on the other hand, if a project or multiple projects are being halted shortly after they have begun it is more a sign that the strategic goals of the business are not super clear and therefore projects are being spun up that are doomed from the start because of a lack of clear business motive for them.

One last thing on this, it is extremely demoralizing as an engineer to be working on a project for months and for management to one day come and just kill your project out of the blue. Whether warranted or not, it just sucks. It makes you feel like you have wasted countless hours of your life on something that didn’t even matter to begin with.

Teams are constantly being staffed/shifted

This one kind of goes hand in hand with reorgs but can stand on it’s own as well. If you notice teams are constantly in flux around you, they are merged with other teams, engineers are being moved from one to the other, new engineers are being introduced because others have left, etc. This may be another indicator that the management team does not have full grasp over the business units that they command.

Something to take note of especially at startups is if you notice the company growing at a faster rate than it can even handle. You’ll notice because at every company meeting a huge wave of fresh engineers are introduced and teams are being created out of thin air. We refer to this as Hyper Growth and even though its a cool thing in some cases, it is also really hard to adjust to as an engineer. It makes it so that you never feel a sense of stability with whatever team you are on which subconsciously adds pressure to your everyday work environment whether you notice it or not.

3. You don’t have a clear path for career progression

I saved the best for last. This point is critical for your career as an engineer and ultimately keeps you cognizant of where you want to make it professionally. If you join a company and there is no clearly defined career ladder laid out, this is a major red flag. No one wants to be somewhere and know that they are going to maintain the same title for the next 10 years because the next title up simply just doesn't exist or people rarely get promoted.

As an engineer I personally always want to have a goal or position in mind at any company so that I know what I am working towards. It keeps me motivated and always pushes me to stay ambitious and driven. Without a clear upward path it makes it hard for me to see how I will stand to gain anything from giving my all to a company day in and day out. Having a clear path to progress as an EM (Engineering Manager) or as an IC (Individual Contributor) are things I always look for when weighing the pros and cons of one company over another.

One last twist to this point. Let’s say there are clearly defined roles at a company but you know that making it to the top is going to take many years of work and you feel as if you are already operating at a higher level than where you were hired. Well, in this scenario there are two options. One, talk to your manager about your career goals and try to get an explicit list of things written down that you can do that will progress you to the next level. Two, you recognize that you want to progress faster than your current company will allow and you start job hunting and applying for positions that will not only give you a pay boost but also the title bump you are looking for.


Once again I am going to call out that not everything I mentioned is a red flag in every single scenario. Some of these things are circumstantial and the only way you will know if it’s a red flag or not will be to experience it first hand and live through it.

These are just some of the things I have noticed throughout the years and countless companies that I have been at that I now know to keep an eye out for. This doesn’t mean that as soon as I feel or notice any of these things that I am out the door. What it does mean is that I am just wary of this because ultimately I want to feel fulfillment, joy, and excitement from my job and being aware of what makes me feel the best at work is one of the many ways I take care of myself professionally.




Prolific Night-Coder. Runs on coffee and Dr.Pepper.