Chapter 4. Moving Forward

In this chapter, we’ll look at the signs to pay attention to when it comes to thinking about quitting your current job and how to define an action plan based on where you are now and where you want to go.

Signs It’s Time to Move On

In 2020, when the pandemic started, our way of life and work changed dramatically and abruptly. Over 18 months or so of pandemic life, many people had more time to think about what they wanted from their jobs and the kinds of conditions they were willing to accept, the impact of which became known as “the great resignation.” For knowledge workers, this conversation has often been about perceived entitlement, such as those who didn’t want to return to the office.

Regardless, your current job is just a moment in your overall career, and it’s worth thinking critically about whether it’s serving your longer-term career goals. Leaving a job isn’t necessarily a sign of giving up or of being unsuccessful. Instead, it may be the best thing for your career, and making a move might be a really positive step.

So, here are five reasons why you may want to think about moving on.

You’re Not Learning (and You Want to Be)

It’s normal to move between periods of higher growth and periods of consolidation, and sometimes it’s a relief to be operating well within your comfort zone. But if you’re poking your head up and looking around, and your next growth opportunity is nowhere to be seen, it’s worth considering that your next growth opportunity could be elsewhere.

The trap

As mentioned in Chapter 1, sometimes five years of experience is just…the same year of experience, five times over. This can really set back your career trajectory, making it harder to interview or get hired for roles you think you should be qualified for by now. Employers who interview in depth will suss out if you’ve been stagnating and will be more likely to pass on you for a “more qualified” candidate whose experience has been more varied.

Before you quit

Talk to your manager about what growth opportunities they see for you. Especially if you’ve struggled personally for whatever reason, it’s worth talking about how whatever was going on is behind you now and laying that period to rest between you, making it clear you’re ready to take on more. Many nice and understanding managers may let people drift a bit, not wanting to add pressure when they’re going through a tough time; being clear about what you’re ready for will make it easier for them to help you get it and know that it’s time to start pushing you again.

If you move on

Be intentional about what kind of learning and growth you can really expect in the new role, and be clear about optimizing for it, even if that comes at the expense of other things you care about (like job title).

You’re Learning Coping Mechanisms Rather than Skills

Every organization has their quirks that people find their way to work around. Perhaps the reporting is a little overly arduous, or your manager’s manager is a little political, or the culture is a little too argumentative for your liking. Over time, we learn to cope with these things: we set aside extra time for the reports, make sure we take the time to sell the political person on our ideas, or learn how to argue.

The trap

Sometimes organizations are (or become) sufficiently dysfunctional that we’re investing more time in developing and refining the coping mechanisms than the actual skills. If your list of things to develop is really a list of things that you won’t have to do in a more functional environment, none of which will make you more employable elsewhere…it’s time to walk away. The coping-mechanisms trap is particularly vicious because the more time you invest in refining them, the more time you’re going to have to spend untangling them in a healthy environment—if you ever make it to one.

Before you quit

Talk to someone you trust who won’t just support you but will also challenge you. It’s important that they have an external or at least dispassionate perspective—someone who’s also deep in the same coping mechanisms will be more likely to justify them, or you’ll just end up venting together. An external coach, a previous manager, or a close industry friend can all be good people to turn to. Ideally, they can check you on what’s bothering you: are you overreacting? Would the grass really be greener elsewhere?

If you move on

Put real thought into what coping mechanisms you have developed and expect to find new ones in your next job. You’ll have to commit to untangling them, and that can be hard, so figure out what support you need.

You Feel Morally Conflicted About Hiring

I’m not suggesting we should all be a corporate shill, but if you’re hesitating mentioning that the company you work for is hiring and you’re offering a lukewarm view or even “I don’t recommend it” to friends who ask you, it’s worth asking yourself: if they deserve better, maybe you do too?

The trap

We tend to consider moving on to the next job much more deliberately than we do considering staying in the one we have. It’s easy to keep ticking along because things are “mostly fine,” but sometimes the questions that people ask when interviewing can remind us that we don’t have great answers to those questions ourselves if we let ourselves think about it. For example, in interviews people will often ask questions around company culture, growth opportunities, and commitment to DEI. It’s worth asking ourselves those same questions from time to time.

Before you quit

Is it the company, or is it you? Burnout can make us feel ambivalent about things that we’d normally enjoy. Try taking a real vacation and seeing how you feel.1

If you move on

Make sure what you’re looking for is realistic. It’s easy to think that other companies have a “perfect” culture based on their external presentation, but no organization is perfect in reality. Validate by asking questions that help you understand the realities of people’s day-to-day—not just what’s on the website.

Your Job Is Affecting Your Confidence

The best advice I received early in my career was “If it’s affecting your confidence, then it’s a problem.” It’s something I still think about and assess situations against. Something might be annoying and easy to shrug off, but things that erode your confidence should be paid attention to. As a rule, over time you should feel more capable, not less. It’s particularly cause for concern when you can look at your achievements and the way you’re being treated and see a real mismatch.

The trap

Once you stop feeling valued and start doubting yourself, it becomes harder and harder to find something else. You’re not valued, you don’t feel successful where you are, so why would somewhere else value you, and why would you be more successful elsewhere? The truth is that success is a product of personal and environmental factors. Maybe all you need is a different environment to help you thrive.

Before you quit

Make the time to thoroughly and (as much as possible) dispassionately review the things that have been eroding your confidence: are there things you can learn from and use to genuinely improve? We talked about getting the most out of feedback in Chapter 3, and again, I highly recommend the book Thanks for the Feedback by Douglas Stone and Sheila Heen. If it’s other things, such as the way your coworkers communicate, consider whether the signs are isolated things you could build some resilience to or trauma from previous bad experiences.

If you move on

A totally new environment can also be a short-term hit to confidence, as we have to learn how to navigate it and ramp up to being effective. Don’t expect a new environment to be an instant solution; give yourself time to adapt.

If you have a good relationship with your manager, you can try asking for what you need. For instance, if you struggle to get the most out of their coaching because you’re so worried you’re not meeting their expectations that you can’t engage with it, try telling them that and see if they can offer some reassurance first.

Your Job Is Affecting You Physically

Stress is physical. At the point where it’s noticeable in your heart rate, sleep (or lack thereof), and physical well-being, you have internalized it.

The trap

The physical effects of stress can sneak up on us, and when you’re not feeling well, the stress and overhead of looking for another job or risking your health insurance may be the last thing you want to deal with.

Before you quit

You know your work environment, and you know yourself—so you know whether it’s worth trying to set boundaries and/or build healthy habits. If you draw a line at stopping work at 6 p.m., will it be respected? If you carve out time for healthy habits, will it be enough to make a difference? If it is, I recommend Gretchen Rubin’s book Better Than Before (Crown) and particularly the Four Tendencies framework as being helpful for thinking about building (and maintaining) habits.2

If you move on

Remember that stress takes time to dissipate and rebuilding healthy habits is a process. Shifting to a new organization can be an opportunity to reset and rebuild healthy habits, but if you’re not intentional about it, you may fall back to the ones you had before.

Making Decisions

Forty hours a week—or, let’s be real, more—is a lot of time to be unhappy. Being unhappy at work bleeds into other areas of our lives, affecting our physical and emotional well-being and personal relationships. I’m not advocating job hopping—there are always things you can try to improve your situation, and we’ll talk more about those things in Section 2, “Self-Management”—but as a hiring manager, I find that the people who make me saddest are those who have stayed in one place too long at the expense of their own growth and overall career. Regularly thinking critically about what you’re getting from your environment—and what you’re not—is key to sustained and sustainable growth. Even if you have a great manager, you’re still the DRI of your career, and abdicating that responsibility doesn’t set you up for long-term success. Tanya Reilly, author of The Staff Engineer’s Path (O’Reilly), has a spreadsheet template you can use to check in on these factors every one or two months.

And if you’re a manager thinking about how to retain people on your team, consider that your best retention play might—ironically—be making it easier for them to find a job somewhere else. Making sure people feel valued and that they’re learning and growing in ways that provide value to them personally and to their overall career trajectory makes it more likely they’ll choose to stay. It’s much harder to trap people when the market is competitive—but that was never a good way to manage, anyway.

Your Action Plan to DRI Your Career

We’ve covered a lot in this section, so here’s a suggested path for applying these concepts to your own career. This can be a significant shift in mindset that can take months, so make sure you give yourself time and space, and don’t get disappointed if things don’t change as quickly as you want them to. This list is long, and maybe a little overwhelming, but you’re not supposed to go through it all at once—review your next action and give yourself some time to take it, then come back to it again later.


Step 1: Assess if it’s time to quit.

  1. If it’s time to quit, or you think it might be, figure out your constraints versus need.

    1. Do you need to make your current role manageable to give yourself time to look for something else?

  2. If you’re a “maybe” on quitting, think about what’s pushing you to that point and what you could try to improve your situation.

  3. If you’re a no, great! Less overhead for you. Move to step 2.

Step 2: Look at what options you want to be available to you.

  1. Check yourself on whether it’s a job or a title. What do you really want to be doing in the 40+ hours a week you spend at work?

  2. Assess where you are relative to these options.

    1. For those of you who are on track, great—you’re done here.

    2. For those of you where that isn’t the case, move to step 3.

  3. Define your current moment.

    1. What is your current moment?

    2. What do you need right now?

    3. Given those things, what constraints do you have here?

    4. Discuss the constraints with someone you trust—do they have to be true?

Step 3: Clarify the deal you made with your employer.

  1. Think about what your employer is renting.

    1. Are you building market value?

    2. Are you undermining market value?

  2. Think about what your employer is buying.

    1. Is there anywhere that they’re taking more than they’re paying for?

    2. Are there any boundaries to redefine?

  3. What kind of deal do you want?

    1. What supports your longer-term goals?

    2. What do you need to support your life right now?

Step 4: Identify some proximate objectives.

  1. Come up with some (one to three) shorter-term goals that support what you identified as your overall career options.

    1. Make sure you really nail the “what” and the “why”—achieving this goal is meaningful to you and will represent meaningful progress.

  2. Put together development plans for each of the goals.

  3. Discuss and refine the plans with someone you trust.

Step 5: Think about your relationship to feedback.

  1. Identify what quadrant you’re in for some key relationships.

    1. If it’s receptive and actionable, great: what’s working, and how did you get to that point?

    2. If it’s receptive but not actionable or not receptive but actionable, why is that? What would help?

    3. If it’s neither receptive nor actionable, why is this?

      Is there a way to extract yourself from this situation?

  2. Think about what you could do generally to be more coachable. Pick one or two suggestions from the list to work on.

  3. Think about some difficult pieces of feedback you’ve received. What can you take from them? Is there anything useful here?

    1. Even in the worst contexts, there may be something we can learn about ourselves. And then, it’s much easier to let that feedback go.

    2. Some feedback and feedback relationships need to go in the bin. Do you need to put anything in the bin?

Step 6: Audit your network.

  1. What relationships are good? Celebrate them.

  2. What relationships are OK but could be better?

    1. Think about how things could be better.

    2. Think about things you could do to improve those relationships.

    3. Decide if you want to make some time to invest in those relationships.

      “No” is OK!

      So is “Not right now.”

  3. What relationships are missing?

    1. Think about what those missing relationships cost you: for example, if you have a very small professional network, maybe that makes it harder to find new opportunities.

    2. Think about what you could do to build more of a network. What would be the easiest things you could do? What would you enjoy?

    3. Assess the gap versus what you might do to solve it, and decide whether or not you want to do it.

      “No” is OK!

      So is “Not right now.”

1 In Europe, these last two to three weeks, and emails and instant messages go unseen and unresponded to. This kind of break isn’t always possible for everyone, of course, and vacation length will vary by the customs of your country. But even a one-week break can help.

2 This framework is expanded on in the book The Four Tendencies, also by Gretchen Rubin (Harmony/Rodale).

Get The Engineering Leader now with the O’Reilly learning platform.

O’Reilly members experience books, live events, courses curated by job role, and more from O’Reilly and nearly 200 top publishers.

Start your free trial