When You Should Leave a Job and Other Career Questions AnsweredQuestions From Our Users

Keyboard, hands, empty coffee cup on a desk with a card that says don't compromise in a job that doesn't make you happy

In our continuing weekly column, our editors answer career questions from around the web. If you have a question on your mind, send it to info@tapwage.com

Dear Tapwage, I know all jobs have their good and bad. I am trying to decide if my current job is “good enough” and if I am just now trying hard enough, or whether it is time to move on. I get the feeling that the company is too large and I am not able to make a difference. Are there things I should try to make the job work better for me, or is it better to move on and start interviewing? — Dazed and Confused

Dazed and Confused,

If you have already done more than a 1.5 years in your current job, you should always be looking. This doesn’t have mean sending your resume out to hundreds of companies. Take a look at openings periodically and see what piques your interest. This regular market check makes sure you aren’t just staying at your current role out of inertia. However, before that period — it’s probably too early to judge a job or a company, so have patience.

The Tapwage Test of Whether It’s Time To Leave:

If you start to feel like your job is getting rote and comfortable, and you aren’t getting the opportunities for learning and advancement, then try this test. Push for more responsibility by taking more initiative. Pioneer a special project that the company needs badly, but no one has gotten around to taking ownership of (large companies have plenty of those). If these proactive steps on your part are getting noticed and appreciated, and as a result you are enjoying the job more — it might be too early to leave. If you feel like people are resistant, or if you are getting more questions than support — then it’s a good indicator that it’s time to move on from this job.

Pushing for greater responsibility and taking initiative often makes the underlying values and culture of the organization clear. The company’s response will crystallize the decision for you.



Dear Tapwage, I have an interview coming up for a role that I now realize is for a more experienced programmer with an understanding of many tools that I am unfamiliar with. I am a recent graduate and was invited back after an initial phone interview. How should I handle it if they ask me questions on the technologies that I have not had experience with? — Stressed in The Valley

Hi Stressed in The Valley,

Candidly — you can’t cram for such an interview. Also if you do get the job by pretending to know 12+ technologies, you are setting yourself up for failure on the job which can be detrimental to your reputation in the long run.

Brush up on the tools and technologies that you know and make sure you come across really strong and confident in those areas. If they probe on the other areas — be clear and confident that although you haven’t had experience with those tools — you are a fast learner, are eager to contribute and build a skill set and be a positive force at the job.

Your best bet is coming across as earnest, hardworking and very knowledgable at the things you do know. Sometimes the most powerful thing to say in an interview is “I am not skilled at that, but I intend to learn it very quickly and have experience with other similar technologies today”. If you try and fake it, you will get caught out either at the interview, or later on the job. If they are indeed looking for someone with experience, perhaps check out our curated channels with entry-level jobs here.



Dear Tapwage, I am a mechanical engineer and am graduating soon. I like designing and building things and I interned with a large energy company last year. I learned a lot on the job and felt people were willing to guide and mentor me. However, a few weeks in, it stopped feeling like a career and turned into a 9 to 5 job. While I am not averse to the occasional mundane task, I felt like a drone. As I look at jobs now, I am wondering whether I should apply to smaller companies, or whether I should continue to look at large companies like where I did my internship. — Small or Large

Small or Large,

You need to be careful about expecting that every job right away is going to give you CEO responsibilities. The question about the job shouldn’t be if the job will be dull to you in a few months, but whether you find your bosses job, and her/his bosses job dull. If the answer to that is yes, then that company is not for you. We say this because the first 1-2 years of your career, especially at a large company are years of investment. You don’t get entrusted with significant responsibilities right away, but as you learn the mechanisms, systems and processes of the organization, the job hits an inflection point in a few years where you have the potential to be significantly rewarded with rich experience, responsibilities and renumeration.

The big company vs. small company is an interesting one, and you are right to value experience over pay. It’s subjective. At a big company, you may not learn a ton by doing and the job can be mundane early on, but you can learn a lot by watching how they operate. How quality control is maintained, how systems and procedures are instituted, how talent is hired, are all lessons that can be instructive early in your career. For a curious mind, such an environment can be a fascinating place early on in your career to build a foundation, whereas at a smaller company, you sometimes learn more by trial and error.

On the flip side, if your itch is to design and build from the get-go, chances are that you will get a better chance to do that at a startup or a smaller company. However, at those types of firms, your immediate boss and your team can be the biggest risk and biggest reward because they disproportionately decide the culture of the firm and the environment you will work in. So make sure to do your diligence and make sure you are working for people you really respect and on a mission that you have conviction in.

Regardless of which route you choose, we have jobs for you. Check out our startup jobs here, and our Fortune 500 jobs here.



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Advice Annie is a team of Tapwage writers and guest contributors who help answer career and workplace questions