Career Management: Is It Time to Go?

Deciding whether or not it’s time to leave your current employer is among the more pivotal moments in a career. Motivations to leave range from excitement about new things or improved compensation to frustration with a current employer’s unwillingness to promote. On the other hand, I see people toil on through bad situations where “the writing is on the wall”.

So when is it time to leave?

We’ll walk through evaluating the situation dispassionately to ensure a quality (rather than purely emotional) decision.

Note – I’ll stipulate that I’m talking about leaving a company, not just changing positions. Some of the same logic applies, but the company change makes it a relatively larger decision.

Question 1 – What’s bugging me?

I’m going to assume you are in a position where you are considering a change. Start with a simple question: “why am I considering moving on?” There are a ton of sensible reasons that are natural. In the normal course of any role, we can feel unhappy, stalled, underpaid, underappreciated, badly treated, stressed….the whole gamut of emotions.

The real question is when do these feelings rise to a level that drives you to look elsewhere?

The biggest “satisfaction” question to work through is “am I generally happy and things suck right now?” vs. “there’s no way this is likely to change in the reasonable future”.

To answer this question, you need to disaggregate the problem. First, get to a personal definition of “satisfaction/happiness”. There are a number of dimensions that make sense. I suggest a balanced scorecard that includes your broad life-goals and has work built in. Elements include:

The nature of your work: Do you actually like the day-to-day of what you do?

I find that people under-estimate the importance of this earlier in their careers. They “over-index” on pay, title, prestige because those are externally validated. Joy in the process doesn’t get talked about a lot.

The quality of your teamDo you like who you work with?

If you do it sure helps keep an even keel and having fun, even when things are tough.

The culture of your company or business unitDoes it work for you?

If your basic personality doesn’t mesh with your employer’s culture it can be hard going. “Fit” actually matters.

Your compensationAre you paid fairly?

If you don’t know, find out. Figure out both internal (relative to peers in your company) and external (relative to similar jobs at other companies) equity. If you aren’t paid fairly, here are some thoughts on getting a raise. If you are, let it go. But either way, you should be able to get data.

Career goal alignmentIs this job helping move you in the direction you want to go?

If you have a plan, is this a part of it? If you don’t have a plan, figure one out!

LifestyleAre you able to live the life you want given work requirements?

This takes a little thought and the changes over time may surprise you. My basic expectations of personal control have changed dramatically over the last 20 yrs. So remember to continually calibrate.

MeaningDoes your job give you some degree of meaning that is important to you?

Are you mission driven and work is a big part of this? I think of my minister, or my friends who are teachers or physicians. Jobs that have a clear service component that drives some societal good can be powerful motivators.

These categories are not scientific, but they work for me. Feel free to adapt them. But once you decide on your categories, then what? I’m a big proponent of writing things down and forcing yourself to be specific about how you feel. So here’s a way to get this on a single sheet of paper.

1 – Write each category down on the left (or put it into a spreadsheet)

2 – Write an “operational definition” to the right of the name. It needs to be a one sentence definition of how YOU define it.

3 – Rank order the categories. They can’t all be equally important. Whether you rank them 1-N and sort, or you allocate 100 points across them doesn’t really matter. What matters is you force yourself to confront your values.

4 – Quantify/rate your current satisfaction. You could do High/Med/Low, score it 1-3…whatever. However you do it, force yourself to evaluate it.

5 – Sort based on leading “dissatisfiers”.

Mock Example




H-3, M-2, L-1


H-1, M-2, L-3



Nature of my work I like the day to day of what I’m doing




Quality of Team My team meaningfully contributes to my work




Culture I like the environment  I work in




Compensation My pay is fair




Career Alignment I’m moving in the right direction and can see interesting opportunities




Lifestyle Work doesn’t significantly interfere with the life I want to live




Meaning I feel good about the impact my work has




Now we have a tangible starting point to evaluate where you are.

Taking the (mock) example above, it’s quickly clear that what I’m most concerned with is the day-to-day tasks and perceived career progression problems in my current role. I can eliminate a bunch of buckets of worries (pay, meaning etc.) and focus in on what’s really bugging me.

Question 2 – Can what’s bugging me be changed?

It’s up to you to be hard-headed is deciding both IF and over WHAT TIME FRAME changes can occur.

For example, if you don’t like the day-to-day work you’re doing, but can see a new position on the horizon in the next six months that might better align with your career goals then waiting may be worth it.

But don’t enter into magical thinking. It’s easy to defer issues, kicking them down the road. Be honest with yourself about where you stand. Having defined what’s bugging you already, be realistic about the likelihood of change. Also remember that the larger the organization, the slower any likely change will be. A former colleague refers to the “rule of pi”, noting that most things take 3.14159 times as long as you think. (That’s a precise and universal bureaucratic constant).

Question 3 – Do I care enough to try and change it?

Not a trivial question. I’ve faced several situations in my career where I thought I knew what needed to be done and believed it could be done, but I knew I didn’t have the energy or will to drive the change. I didn’t want it badly enough.

So given how the pros and cons in your assessment stack up, do you care enough?

If not, it’s probably time to go…

Question 4 – Have I considered everything in reaching my decision to leave?

A few considerations before you pull the trigger…

Risk: What are my switching costs?

People underestimate the value of relationships and persistence. Many Sr Execs made it there thru staying power as much or mare than for sheer performance. So just be sure you aren’t leaving career value on the table out of shorter term frustration.

Also – if you have three kids (like I do), your definition of “risk” is different than my recent grads who are OK eating ramen and sleeping on someone else’s couch. So don’t be hasty before considering consequences.

Options: How good is your exit opportunity?

Leaving presumes (for most) having a place to go. I like to think about whether you are leaving something or going to something. Recognizing that there’s always a bit of both, I’d encourage you to make sure the positive feelings about the new opportunity are pretty high and that it addresses the key dis-satisfiers you’ve laid out. Here are a few thoughts on searches.

Traps to avoid:

Leaving too soon – I see a lot of “jumping”. 3-5 years somewhere is worth a lot more than 1-2. You show potential employers persistence and progression. You also learn A LOT more. Really. Somebody else wooing you and being offered 10% more isn’t that big a deal, so don’t get sold on a bad move prematurely.

Staying too long – On  the other hand, don’t let too much moss grow on you. At a certain point, you are potentially losing your market value. Baseball GM Branch Rickey is famous for saying “better to trade a player a season early than a season late”. Don’t ride a bad situation into the ground.

Paving the way out through underperforming – A variant of staying too long, this is the “I really want to leave, but can’t summon the will. So I’ll just dog it.” Bad, bad, bad…Destroys personal and career capital. You’ll both piss off colleagues, get a bad review and damage your future prospects.

A final thought on the “long-term”. Much like my views on networking, I view this self-assessment as part of larger and continuous cycle. Don’t fixate on “am I happy/learning/advancing” everyday. But do set aside time 2-4 times per year to actually think about it. If you don’t define goals and then reflect on progress, you’ll never recalibrate.

I think we’d all rather be in positions to move from good situation to good situation. This requires you to have some degree of self-awareness, but also to be developing a hopper of interesting opportunities continuously. If you are good and active, you may be surprised what finds you.

So should I stay or go? I don’t know, but now you have a suggestion for how to work through it…

3 thoughts on “Career Management: Is It Time to Go?

  1. I came across this post too for my former position. I can see how, if I’d assessed my situation in the manner you suggest, I may have clarified some of my personal and professional goals, instead of trying to “work through the pain,” which contributed to stress, frustration, complicated relationships, etc.

    I am going to apply your approach as I evaluate new opportunities, which, although too late for the past, is an excellent way to begin in a new role. Thank you!

    • I’m glad it helps. I see too many people stay unhappy for too long. The key to me is stepping back and being concrete about what’s not working (or what is). Let me know how it goes.

  2. I just stumbled on this particular post, and even if it was written months ago, it can still help so many people who are feeling stuck in their jobs and just need to look at their jobs from different perspectives and see if they still benefit from what they do.

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