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The Mercenary’s Guide to Should I Stay or Should I Go?

Look at that!  It’s Monday and I’m actually doing reader question Monday.  Just kidding.  Once again, I’m doing reader question Monday on a Tuesday.  In fact, I am going to pull the trigger on switching it to Tuesday going forward.  My wife and I are experimenting with a 4 day week that would make Tuesday the new Monday for us.  Also, for those of you interested in blogging advice, Tuesday is a better day to publish posts, anyway.

Enough of This!  What’s The Question?

Alright, housekeeping aside, let’s get down to brass tacks.

Do you have advice for helping one answer the age old question, “Should I Stay or Should I Go?” At what point is it time to throw in the towel and move on?

I don’t want to be a quitter and always have regret that I missed out on the company becoming an awesome place six months after leaving. Yet, I don’t want to waste six months of my life and career on hopes and opportunities that never manifest into reality.

I’m well aware the grass isn’t always greener on the other side and all companies have problems. However, in today’s developer advantaged job market, when is it time to change one’s attitude from “I can make a difference” to “Not my problem anymore”?

Thanks for writing and publishing such thought provoking content. I really enjoy reading your articles; even though you write faster than I can read 🙂

Well, first of all, thanks for the kind words!  Failing to create enough volume of content has never been a problem for me, to be sure.

I Have Biases, So Let’s Get Those Out of the Way

Now, before writing this post, I need to address something.  I have, in the past, written posts encouraging you to job hop, saying that you should always be leaving, and that you take jobs already thinking of your exit strategy.  I also wrote a book with an entire part devoted to the merits of viewing the very existence of a company as a limiting illusion.  So there’s that.

I mention this because you need to understand where I’m coming from with my advice.

This isn’t to say that I can’t conceptualize enjoying being part of a larger whole or regarding a company as a potentially benevolent entity.  It’s more that I would tend to view those things as creature comforts that conflict with career advancement.  For people looking to get ahead, I wouldn’t recommend a company collectivist attitude.

That said, I’ll do my best to put aside my own preferences and beliefs.  Just know what those are as you read: I’m a mercenary and a lone wolf and, when it comes to jobs, a quitter.

You Could Be Missing Your Next Big Opportunity Because You’re Reading This Blog Post!

If you’re the sort of person that skips section headers, indulge me for a moment.  Go read the one right above this paragraph.

What I’ve done there is marketing trick, except that it would make me the worst marketer in the world because I inverted it.  Marketers take advantage of a human cognitive bias known as “FOMO” or “Fear of Missing Out.”

Our brains, as it turns out, are hard-wired to fret endlessly over the road not taken.  Did your failure to check Facebook all day result in you missing the best meme ever?  Should you eat at that Thai place on the corner that you don’t really like simply because it’s going out of business and you’ll never again have the chance?  What about that job interview you passed on for “Junior Tester?”  Sure it doesn’t sound like a fit, but it might have been a great company that would have seen your talent and promoted you to a better role.

Probably even just reading that paragraph triggered a mild unease in you, for at least one of those questions.

Cognitive Bias to the Rescue

The reader question here is loaded with FOMO, and that can become paralyzing.  Will I miss out if I go?  Will I miss out if I stay?  Argh!!

Luckily, you can fight cognitive bias with cognitive bias.  A form of confirmation bias has us disproportionately look back and conclude that we’ve made the right decision.  We convince ourselves that we chose wisely, and that, in turn comforts us.  As humans, we tend to be content with what we do, no matter what it is.

So rest assured.  And I say this not even with my tongue in cheek.  Whether you choose to stay or to leave, you will almost certainly be happy with your choice on a long timeline.  (Unless you’re acutely miserable, in which case you’ll just make a new choice and be happy with that one.)

But however you cope, fight the FOMO.  It’s our brain tricking us into irrationality, and it will not help your decision-making.

Don’t Take or Stay in a Job with the Hope that It Will Become What You Want

So the first piece of concrete advice is in the books.  Become zen with the path not taken and confident that you’ll find happiness with the path that you do take.  If you’re miserable at a job and you leave, you’ll be happy about leaving in six months, even if fortunes at that org improve (which is sorta unlikely, anyway, in my experience).

The second relevant heuristic I’ll offer involves not assuming that things will get better.  This article that everyone I know has been tweeting/messaging/slacking me lately about why someone quit Google has a cautionary tale in it that I hear over and over again.

I can’t say I wasn’t tempted, but by that point, I’d been hearing, “great shot at promotion in six months,” for the past two years.

This is the most common thing ever in the corporate world, and do you want to know why?

Because it’s a lot less effort and company cost to endlessly promise future promotions than to actually grant them.  And same thing goes for any kind of improvement to your station there.  That also applies to job offers, by the way, as I once learned the hard way.  “We’ll start you off as Engineer III and promote you super-quickly once you prove yourself.”  Pff, super quickly was years, and only after a manager that really liked me got creative.

Unless it’s already happened, believe that it probably won’t ever happen.

Get More Concrete Than “Making a Difference”

So far, I’ve talked mainly about what not to do: don’t let yourself fall prey to FOMO, and don’t let vague promises sway you.  Now, let’s talk about what to do.

The first thing I’d suggest is to make concrete any vague reasons you have to stay.  (Though, as an aside, I’d listen to your gut on vague reasons to leave, but that could make for a whole other post.)  For instance, in the case of the question, a compelling reason to say appears to be “I can make a difference.”  But for the rest of you, it might be things like, “I’m comfortable” or “parts of the job really satisfy me.”

Those are all understandable sentiments, but they’re not quantifiable or really even qualifiable, exactly.  This makes them also not actionable.

What does “making a difference” involve, and why do you want to do it?  Does that mean adding 10M in revenue to the top line?  Does it mean having several teammates remark that you’ve helped them?

Once you start answering questions like these, you can start evaluating your motivations.  Are you in it for the feels?  For pats on the head?  For the money?  And what would you like to have achieved in 6 months or a year?

Once you understand those answers, evaluating new employers versus the current one starts to become child’s play.

Understand the Nature of the Company and Your Relationship To It

If you get into this habit of turning feelings and impulses into measurable outcomes and goals, it becomes just that — a habit.  You’ll start to view jobs less in nebulous terms like “culture” and “environment” and more as either obstacles or enablers to your goals and objectives.

From there, it’s not a huge jump to seeing companies in terms of the corporate hierarchy that I’ve defined.  That is, there’s really no such thing as “the company” in any meaningful sense.  Most (non-opportunist) people have asymmetrical relationships with companies.  They perceive a belonging that only exists collectively in their minds.  In other words, they all come together to create the shared fiction of corporation-as-family, whereas the legal LLC and its EIN do not feel the same toward the people since they’re, well, a piece of paper and a number, respectively.

I’m ending on this somewhat cynical note for a reason.  If you want to belong to a group of people and feel a sense of shared culture at a company, then by all means do so.  But also recognize two things:

  1. This is a luxury that often comes at the opportunity cost of advancement.
  2. Savvy organizational managers use this subtly against you (e.g. by creating narratives stigmatizing leaving companies)

So when do you throw in the towel?  What I’d advise is that you quantify everything, including your own desire to belong to the company as a tribe, and throw in the towel when you can make a business case for it.  Because that’s the only way that you or I could answer that question with something other than “when you feel like it.”

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2 Comments on "The Mercenary’s Guide to Should I Stay or Should I Go?"

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Mike Loux
This is timely. Review “season” just finished up at the place where my wife and I both work, and while we both got glowing reviews, hers got pushed down due to the “mandatory curve” (she happens to work in the same group with 2 people who are always “rock stars”), and my raise was tiny due to the whole “market value” thing. Now I’m still waiting for my promotion to manager (I had just been promoted last year as an IC, so got hit with the whole “try before you buy” bit) and it that does not happen before too… Read more »