How do you think about staying within a company versus looking for opportunities outside? When do you know it's time to leave?

This is always a deeply personal decision, but over the years, I’ve found myself in scenarios where I stayed too long because I was comfortable. Here is my rubric for determining whether to stay or go: Am I still learning? If you’re not learning something new, it’s easy to become complacent. The earlier you are in your career, the more you should demand to be in a position that challenges and stretches your skillset. If you have great leadership and perform well, you can often find ways to grow ...Read More

I like 2 use 2 things to evaluate a job: I should either learn a lot, or earn a lot (or ideally both!). We try to always favor learning, but sometimes your familial situation makes that earning may become the main criteria at some moment in your life. Overall, your career is not the most important, your life is. Nothing beats feeling good in your life, and this is what you should look for. I don't think there is any way to measure when it's time to leave, but usually you know it. Deep in you, yo ...Read More

There are a couple of factors to consider here: Are you learning anything new in your current role? If not, would staying with the company, even if it is in a different role, or a more senior role (be that IC or management), satisfy your learning? Do you enjoy the domain, vertical, and business model of the company that you work for? What are the company's growth prospects (or if a startup, prospect for success -- however you define success?) Be very honest and don't just take company management ...Read More

There are some absolutes, which may be self-evident, but I'll still mention them for the record: disrespect, discrimination, excessive stress, unreasonable and unhealthy workload, workplace toxicity in all it's forms, the company is unethical or is visibly tanking...and many more.  Otherwise, I suspect the most common reason to leave might be simply put as: a better opportunity elsewhere. Now, this is a very personal calculus that becomes harder if things are not exactly terrible. Perhaps you ar ...Read More

To make this decision, I think of opportunity, ambitions, passion, and time: Opportunity - obviously there is a matter of compensation, but there is also an opportunity for professional growth. For example, joining a startup allows you to grow much quicker -- you will be wearing different hats and working much closer to the company leadership. You will make a lot of mistakes, but the learnings will be much greater. Ambitions - depending on where you at in life, different things might take a prio ...Read More

When considering whether to stay at a company or look for opportunities elsewhere, I always reflect on the reasons I joined the role initially and evaluate how these align with my current experience. For me, a significant factor is the leadership I work under. I often say, "I join a role for various reasons but leave when the boss leaves." The departure of a boss whom I respect and have learned from can be a signal to reassess my position. It's important to evaluate if the change in leadership a ...Read More

As a general rule of thumb - always be on the lookout. Dedicate whatever time works for you: 1hr/week or 1 hr every other week in making connections outside, thinking about a new problem to see if that area is exciting to you, talking to new recruiters to see how your skills are being perceived in the market. If you are thinking about this question, that might be a signal itself. Having clarity on what you're looking for professionally can be useful as well - what do I want vs. what am I getting ...Read More

The answer here is extremely nuanced and will vary from situation to situation. There's a phrase from Graham Weston that has stuck with me from my time at Rackspace: “What we all want from work is to be valued members of a winning team on an inspiring mission.” When that phrase no longer rings true for me, and I see no way to achieve that in my current role, it's time to look for opportunities within the company. If there is no way to achieve this within the company, then it is time to look for ...Read More