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How do you know when it’s time to quit your job?

August 21, 2014

Answer by Edmond Lau, engineer at Quip

A number of red flags should cause you to reconsider your position at your current company, including:

Being compensated unfairly.

Being mistreated, undervalued, or disrespected.

Disagreeing with the fundamental strategy or practices of the company and not being in a position to change them.

Failing to get along with your manager and your teammates.

Failing to fit in with the company culture.

These types of reasons aren’t too hard to identify and provide concrete justifications for trying something new.

It’s also time to leave when your learning rate at your job tapers off and starts to plateau. This is a much more subtle reason for leaving that’s harder for people to recognize but likely affects a much larger group of people. Transitioning to another team or company provides an opportunity to switch to a different learning curve and to accelerate your learning.

Paying attention to your learning rate is important in general but particularly important for young professionals. Learning is an investment in yourself for the future. It also compounds — knowledge not only begets knowledge, but more knowledge gives you a foundation upon which to gain knowledge even faster. This is why most people learn more in college than they did in high school and more in high school than they did in earlier years. Ideally, out of college, you should set yourself up to learn even more than before.

Palantir Technologies co-founder Stephen Cohen captures the importance of the compounding effects of learning in an argument for why college graduates ought to work at startups instead of established companies:

If you graduate from Stanford University at 22 and Google (GOOG) recruits you, you’ll work a 9-to-5 job. It’s probably more like an 11-to-3 job in terms of hard work. They’ll pay well. It’s relaxing. But what they are actually doing is paying you to accept a much lower intellectual growth rate. When you recognize that intelligence is compounding, the cost of that missing long-term compounding is enormous. They’re not giving you the best opportunity of your life. Then a scary thing can happen: You might realize one day that you’ve lost your competitive edge. You won’t be the best anymore. You won’t be able to fall in love with new stuff. Things are cushy where you are. You get complacent and stall.

Startups might not be for everyone, but the message about not shortchanging your intellectual growth rate still applies.

What about a passion for what you’re working on? A strong passion and excitement in your company mission or in what you’re doing is critical to sustaining a steep learning curve. Passion and meaningful work supply the motivation for long-term learning and allow you to stay in a state of flow more often. Mihayli Csikszentmihalyi, one of the world’s leading researchers in positive psychology, developed the theory of “flow,” a state where you enjoy what you’re doing so much that you don’t even notice the passage of time, and found that more flow generally leads to more happiness. It’s hard to stay motivated to learn or to enter a state of flow in the long run unless you believe in and enjoy what you do, and it’s also hard not to be getting better if you love what you’re doing.

Assessing your learning rate first requires identifying the many different types of learning at a job:

Technical learning specific to your job function. For a software engineering position, for example, this might include things like learning a new language, getting familiar with new tools, improving your ability to design new systems, etc. Getting better at these skills makes you more proficient as an individual contributor.

Prioritization skills. Oftentimes, there are tens or hundreds of things that you could be working on that might generate value. Figuring out the highest leverage activity that generates the most value for the least amount of work at any given point is hard, but it’s probably the single most valuable lesson you can learn professionally.

Execution. Learning how build and deliver a great product or service and how to do it consistently and on time takes practice.

Mentorship/management skills. The faster an organization grows, the sooner you become a more senior member of the team. Seniority provides opportunities to mentor or manage other teammates, to shape the company culture and values that develop, and to influence the direction of the team.

Team leadership skills. The skills needed to make a team function effectively differ from those needed to be productively as an individual. How should milestones be organized? How do you coordinate effectively and minimize communication overhead? How do you make sure a team gels?

At various points in your career, you’ll value these skills differently and should seek out opportunities that develop the skills you value. All of these skills are mostly generalizable beyond your job at your current company. You take those skills and experiences with you to your next job.

There’s also a type of learning that’s important for career success but that is less transferable to other companies. And that’s institutional learning on how to function well within the specific processes defined at the company: how to get the approval of key gatekeepers for decisions, how to get projects you believe in prioritized on the roadmap, how to negotiate for more resources for your team given the company’s resource allocation process, etc. Some amount of this is necessary to do well, and some of the negotiation and persuasion skills will help in the future, but to the extent that much of this learning deals with the particular bureacracy or process that you need to deal with, it’s significantly less valuable than other types of learning.

When you first join a company, the learning curve usually starts really steep (hopefully, if you’ve made a good choice). You’re immersed in new technologies, in a new product, and on a new team, and there are opportunities to learn along multiple dimensions. When I first joined Google right out of college, I learned a lot in my first six months there. Google’s done a great job with their GoogleEDU training materials. I soaked in all the codelabs that discussed why core abstractions existed and how they worked. I studied programming style guides to learn best industry practices. I read design docs about search indexing and other scalable engineering systems being built internally. I learned to build and ship something seen by tens to hundreds of millions of people per day on

Your learning rate might decrease due to organizational issues (maybe processes have become too bureaucratic and limit your ability to iterate and launch quickly) or due to maintenance issues where the team doesn’t grow quickly enough to scale with the complexity of the product. The second makes it hard for you to switch projects and work on new things.

Warning flags for me at Google started to appear when I realized that many projects either had no concrete launch paths or depended on non-transparent approval processes over which I had little visibility or control. Being able to launch products was important to the extent that I wanted to learn how to build great products, and quick, iterative feedback is a necessary foundation for learning. When I projected what I could accomplish and reasonably launch by staying an additional year, I didn’t feel satisfied, so I left. There was certainly more I could have learned by staying — I could have dug into the internals of more major systems — but my rate of learning no longer mirrored what I encountered when I first started.

I similarly left Ooyala when I felt that my own learning rate at the company began to plateau. While I was there, I learned about building and selling an enterprise product, the intricacies of flash video and analytics, project estimation and team organization, and more. I left when it became clear to me that I could learn much more on engineering and on building a product by joining a smaller and faster-growing team. A contributing factor that I only discovered after working at Ooyala for a while was that I wasn’t nearly as excited and motivated to work on an enterprise product as I was to work on a consumer product that I would actually use everyday.

Having worked at Quora for two years, I’m happy that I’m still continuously learning new things at a good rate, and it certainly helps that the product itself is also so learning-focused.

When I interned at Microsoft the summer of my junior year in college, I received a good piece of advice second hand from a friend’s mentor: always re-examine and reflect on where you are in your career at least every two years. Even if you’re perfectly happy with your job, the exercise forces you to check that you are actually enjoying your work and learning on the job rather than just being comfortable.

Answer J. Mike Smith, career coach

Good question. It’s tough to answer and know exactly when to quit.

The simple (not simplistic) sign is that you’re not excited about anything you’re doing or can do; you start asking yourself why you’re sticking around.

Having said that though, I just worked with an executive who had a great role (boss loved him, paid well, lots of autonomy, etc.) and who was ready to pack it in but just didn’t realize that for where he was in life (3 younger kids, a job that didn’t cause him to be out of town frequently) he had a pretty sweet deal. Perhaps not a forever deal, but a great role to have at a time where he could put energy into his family before the kids went away for a few years to adolescence.

I think it helps to take a more broadly balanced view. Work, at least for me, is pretty important. But as the saying goes, your job doesn’t kiss you on the cheek at night when you go to bed. It helps to take a look at all the things that make up your life (work, self, family, community, etc.) before you chuck in one element because it’s not perfect.

Answer by Vatsala Shukla, career and life coach

The indicators that it is time to move on start coming to your attention but you ignore them until they cannot be ignored. The fact that you are thinking about it means that there is something that is not quite working for you in your present situation. The most important reason, for me would be potential burnout.

Here are 7 circumstances where I would recommend taking an honest look at your situation and considering whether you should look for new pastures.

You don’t feel like going into work on Monday mornings and often call in sick

You don’t enjoy the work you are doing – it could be under or over-challenging

Your relationship with your boss is far from satisfactory with no open lines for communication

You have lost interest in your professional development to get ahead on your career track

You are not motivated to perform well in your job and only come into work because you need to log in your attendance

The ambiance in the work place is ‘toxic’ (unhealthy levels of gossip, backbiting, politics and negativity)

The stress level in your job is adversely affecting your health and/or personal relationships

If you answered yes to point 7, it might also be pointing toward a potential burn-out.

Answer by Benjamin Shoham, entrepreneur

There’s a disease called “employee numbness” caused by satisfaction from one’s daily routine and compensation. Many employees will keep on doing the same things they did yesterday and a year before, and will avoid any changes, just because it’s all comfortable enough.

I see a professional career as a path to improvement both on the professional and the business level. If you are stepping in place, you’re not following this path.

I like to ask myself two questions every morning (or at least every week): 1. Am I getting more professional doing my job? 2. Is that the best business choice for my current financial situation?

I always keep my eyes open for new opportunities, and always talk to anyone interested in working with me. As long as I keep saying “no” to new opportunities, that means I’m in the right place for me right now. As soon as a better opportunity comes along, I say goodbye and take the next step.

This question originally appeared on Quora: How do you know when it’s time to leave your current job and move on?