How to Know When It’s Time for a New Job

I have always been curious about how people know when it’s time for a new job. 

This question became especially relevant for me last year, when I started to wonder about my next step. Though I really enjoyed my job working at a technology marketing agency, I knew that staying somewhere just because it was comfortable wouldn’t ultimately get me where I wanted to go. 

But wait, where did I want to go? I’d always been an ambitious person when it came to my career but I’d really only thought about it in vague terms: I wanted to do meaningful work, I wanted to be financially independent, I wanted a job that I enjoyed doing (after all, the average person will spend one-third of their life at work). Beyond that, I was clueless.

When I found myself wondering how I could possibly know if it was time for a new job — much less what that new job should be — I realized that I couldn’t make the leap until I figured out exactly what I wanted from my career.

Career Conversations

Up until this point, I had always made my career decisions during times when finding a job was my top priority, like when graduating college or moving to a new city, so I had never quite had the luxury of sitting down to contemplate what I wanted out of my career long-term.

Around September of last year, I had begun listening to the Radical Candor podcast. That’s where I first heard about the concept of Career Conversations: a technique for managers to help their team members grow by facilitating structured conversations about their professional goals, desired areas of growth, and how they can work together to make it happen. It sounded like the perfect way to get some guidance and perspective on my next step. The only problem? My supervisor had never heard of Career Conversations. 

So I decided to adapt the technique to help me map my own career goals.

If you feel like I did, a little unclear about how to determine what you want for your career or how to get there, then this technique is for you. These three exercises will help guide you through career planning so that you can learn what is important to you, understand where you want to go, identify the stepping stones you need to hit along the way and build the best possible plan of action for getting there. 

Step 1: Themes from the Past

The most important thing I did at the start of my search was to map my career path. I started by creating a timeline for my personal career history. Under each year, I listed what job I had held, my main responsibilities, the industry, and what my trigger was to leave. 

For example, I started my career doing editorial writing, then worked as a marketer in higher ed, nonprofit, small business, and freelance capacities before joining the agency world. I also created the same timeline but for my non-professional pursuits: the things that occupied my time outside of work, including hobbies and volunteering — things that I would do even if no one was paying me.

I noticed that across all my paid and unpaid pursuits, some common themes emerged: writing, learning, technology, and strategy. I quickly recognized that the time I’d spent in the tech industry had been the most engaging and challenging work so far. I also realized that I thrive when I am able to deep dive into a single brand and build a strategy from there, rather than working with multiple clients or simply doing tactical execution.

Write down the big themes that appear in your own timeline. Ask yourself: What didn’t you like about each of those roles? What did you love? Hone in on those major pivots and transitions — why did you make them? What did those transitions teach you about your work? This should help you start to understand your motivations and values, the things that drive you. They should be a core part of your decision-making process when thinking about your career.

Whether your timeline feels like a clear, linear path or a zig-zagging journey, pause to ask yourself where it is taking you. Your career will continue to move forward whether you’re thinking critically about it or not. If you don’t start to actively shape the path you’re taking, you’ll still get somewhere eventually. It just may not be the place you wanted to go. I had gotten some great experience and refined my skills during the three years at my current job — but if I continued down that path, it would take me further from (not closer to) my ultimate goal.

Step 2: Vision for the Future

You know that question that sometimes gets asked in an interview: where do you see yourself in 10 years? Before the start of this process, I had a vague idea of what I wanted to do for a living. The purpose of the “Vision for the Future” exercise is to clarify those dreams, bring them into focus and then create an action plan.

I started with research. I invited friends, colleagues, and people I admired out to coffee to learn about their career paths, job histories, and where they saw themselves in 10 years. I started thinking about my own future in more detail: Where do I want to be at the peak of my career? What job title do I want to hold? What industry and stage/size of company do I see myself in? What will I be working to achieve? I wrote down the answers to these questions and a picture started to form of where I was going:

I wanted to transition from agency to in-house.
I wanted to work for a bigger company.
I wanted to become more immersed in the tech industry.
I wanted a chance to focus on strategy, not just tactics. 
I wanted to work alongside a team of smart, inspiring people. 
I wanted room to grow, in both terms of responsibilities and leadership. 
I wanted to learn and be challenged in my day-to-day work. 

All of the exercises above helped reveal a few important things, both about my next job and my career as a whole. The next step was to take those goals for the future and figure out how present-day me was going to get there.

Step 3: Plan for The Present

“Themes from the Past” showed me the path I’d taken so far, “Vision for the Future” helped me identify the destination ahead — and “Plan for the Present” is where I charted out the stepping stones that will would help me get from here to there. 

In Step Two, I’d figured out what job title I wanted to hold in 5-10 years, so I brainstormed a few variations and looked up job descriptions for that role. I went to the Linkedin pages of people who currently hold that title and see what steps they had taken to get there. 

Based on this research, I started compiling a list: What skills are required that I am missing or not as strong in? What experiences do I need to be getting now to prepare myself for a decade from now? Are there new responsibilities I can take on? On-the-job certifications I can work toward? I identified concrete skills I want to grow in, training I want to pursue, and conferences I should attend. I still keep this list up-to-date, reference it on a daily basis and continue to add to it when I identify new gaps or opportunities that I could work on.

Once you have your own list, it’s important to remember that you don’t necessarily need to get a new job to start marking things off. Many times, you can get that experience right where you are. That was the case at my last job when I shared all of this with my boss and invited him to be a part of helping me achieve my goals. His response exceeded my expectations: once he understood my career goals, he enthusiastically offered his mentorship and guidance. He became my advocate and sponsor at work, completely transforming my job description and day-to-day responsibilities so that I could get the experience I needed to set me up for my next step.

I know from my own experience that it can feel a little daunting to share these goals with your boss, especially when it means admitting you have ambitions beyond your current company. But having ambitious, engaged employees who are focused on their personal and professional growth will benefit the entire company — and any good leader will recognize that.

The Outcome

After completing all three of these exercises, I had a vision for where I wanted to go and I also had a clear idea of what my next move would need to be to get there. It made the prospect of leaving a comfortable, enjoyable job make sense in the context of my larger career. So I started interviewing.

Even during the job search process, having a clear idea of what I wanted made interviewing and decision-making so much easier. I’m happy to say that after considering a few different options, I landed a new job that is perfectly aligned with my career goals!

I’m curious: if you’ve quit a job before, how did you know it was time? If you’re just starting to think about your next step, what questions do you have? Let me know if you try out any of the modified Career Conversations exercises above. I would love to know what you got out of them.

1 thought on “How to Know When It’s Time for a New Job

  1. Vanessa Carranza

    I really enjoyed this read Lane. It seems that your relationship with your boss was great. What if it is not on good terms? How would you present this technique to them? Any advice?

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