My first job out of college was as an art director at a boutique print ad agency. It was a poor fit for me and I lasted three months before switching to web dev. Before I quit, I took a walk around the block during my lunch hour and thought long and hard about whether I should quit or not. What were my criteria? I ended up with six questions and my answers to these questions gave me the confidence I needed to acknowledge that it was time to find a new job. I've been using these questions to guide my career ever since.
1. Are you learning and growing?
By gaining new skills and experience you can prepare yourself for the next step in your career, whether that's at your current company or somewhere else. For example, exposure to new domains can enable you to switch fields more easily, thus hardening your career against economic downturns. And deepening the experience you already have can prepare you for greater levels of responsibility and subsequent promotions.
In the case of my first job, my responsibilities required me to work with well-established tools and technology (anybody remember Quark XPress?), working in a medium (print) which was rapidly being displaced by digital media. I felt like I was learning skills that were already obsolete.
2. Are you getting paid enough?
Your compensation should grow steadily each year as you gain experience and take on more responsibility. If your comp isn't keeping pace with the value you provide, it's time to move on. Early in your career is the best time to switch jobs after brief one- or two-year stints, boosting your salary with each job hop.
In my situation I was fresh out of school and had very little insight into what my skills were worth so I'm pretty sure I was underpaid from the start. But by switching jobs I was able to increase my salary by 40%.
3. Is your company in a high-growth industry?
Companies in stagnant industries often have to pay more to retain individuals. Think about all the COBOL code that runs our ATMs and banks. You can make plenty of money working on these systems, but inertia will grow over time as you specialize on those legacy systems. You can gain more freedom in your career by working in industries that are growing because your experience will be in higher demand, resulting in more job opportunities.
Print is dead today and was already on its last legs when I started working in that industry. Did I want to make a career of working in print? The thought made me feel queasy. Not good!
4. Does your company confer prestige?
Google. Amazon. Stripe. Netflix. Apple. These companies carry strong positive brand recognition and when people see them on your resume they subconsciously associate those positive impressions with you. Companies can also lose prestige – for example, one could argue that Facebook's rebrand as Meta cost it some prestige or that Microsoft has lost its prestige since the 90s. If your company's reputation has dwindled, then it might be time to move on to a company that still shines. Will Larson shares a valuable perspective on prestige in his post, "A 40-year career".
My career started off at a company that held zero prestige, but once I focused on tech I began considering the brand-name recognition of the companies I would join. While it wasn't always the deciding factor I did weigh it against salary, role, growth opportunity, and the other items in this list.
5. Are you growing your professional network?
The friendships and relationships you form through work can make the job more enjoyable, but they also represent a professional network that can lead to referrals and job opportunities in the future. This is another topic that Will touches on in the blog post I linked to, above. Is your network continuing to grow during your tenure at your company or has it plateaued? If you've already built all the relationships you can, that might be a cue to move on.
I got along OK with my coworkers at my first job, but they didn't inspire me or seem interested in the kind of challenges I was interested in. I knew after a few months that our careers were likely to diverge and we probably wouldn't stay in touch.
6. Are you having fun?
Starting a new job is an exciting time. You're learning your way around and glowing with the accomplishment of taking the next step in your career. But stick around any company long enough and you'll notice the warts. If you find yourself becoming frustrated or cynical, or if you discover your company's culture is toxic, my advice is to leave.
My first job was exciting by virtue of being my First Real Job. But after the thrill of simply having a real job wore off, I found myself super-bored and looking at the door.
Setting a threshold
At the end of my lunch-time walk, I found that I had answered "No" to each of these six questions. Without a doubt it was time for me to move on. But what if I had answered "No" to five of them, or four? Or only one? How dissatisfied do you have to be before you look for your next job?
This is a personal threshold you have to set for yourself. Once you know how many "No's" is enough, you can start using these questions to tell when it's time for you to take the next step in your career, too.
Leaving one job and starting another is how we build our careers. We want our careers to go up-and-to-the-right along all dimensions -- growth, compensation, prestige of the company we're working for, and all of the other aspects that these questions touched upon. But rarely does it work out this way. For example, you might take a pay cut in exchange for working in a new domain that you expect will yield higher-paying opportunities in the future. Gergely Orosz wrote an excellent article related to this topic called "The Seniority Rollercoaster". I recommend reading it to gain specific insight into the tradeoffs you'll make between the dimensions of level and compensation as you move between "lower-tier" and "higher-tier" companies in your career.