The Silicon Valley Voice

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Work Daze – Quitting Time

Ding! Dong! Ding! Dong!

Those are sounds you hear every working day. They’re the chimes of your own personal Big Ben, telling you it’s time to quit a job you hate.

But how do you know when it’s time to quit a job you like? This is not so obvious; especially if the job you like comes with a paycheck you absolutely love.


Like it or hate it, making the decision to quit a job is never easy. You’ve always believed that if a company were willing to employee you, and pay you, and ignore your shenanigans, that was a job you’d only quit when hell freezes over. And since global warming has made it far less likely for hell, or anyplace else, to freeze over, it’s probably become a job you plan to keep forever.

But times are changing and it may not be the best course of action to wait for a undeniable sign from above saying it’s time to go — a sign like two uniformed goons appearing at your workstation to confiscate your laptop, shred your badge, throw your Hummels into a cardboard box and escort you and the “Little Goat Herder” to the sidewalk.

To provide answers to these questions, I recommend Heather Yamada-Hosley’s recent post on — “How to Know When It’s Time to Quit a Job You Like.”

Yamada-Hosley suggests you “think about your long game.” To do this, there are four factors to consider, which are a lot of factors for someone whose limited brainpower is totally overloaded separating Lannisters from Tyrells in “Game of Thrones.”

Let’s take them one at a time.

Factor No. 1 is “Skill development.”

Are you learning the skills you’ll need in the future? As companies deploy more advanced workflow tracking devices, will you still be able to take a morning and an afternoon nap, or will your failure to keep up with technology limit your naps to daily staff meetings?

Understanding the long-term future for your company’s products and services is Factor No. 2. What if the downturn in 8-track cassette sales isn’t temporary? Will there always be a need for chimney sweeps, or will a flashy app disintermediate the entire chimney sweep industry? (Think it can’t happen? When is the last time you saw a help-wanted posting for lamplighter or rat catcher?)

Factor No. 3 is “will the company, and your manager, invest in keeping you happy when it comes to your salary, including raises and bonuses?” You did get a cost of living increase in 2015. Unfortunately, it was based on the cost of living in Moldova.

“Career Path” is Factor No. 4: “Do you, or your manager, see a clear path for you within the company? Maybe your manager’s job, or transitioning to another team?”

Even if you do detect a career path you may not like the eventual destination. I refer, of course, to the shortcut from the lofty position you occupy today to the bench you occupy tomorrow at the unemployment office.

Of course, you must also consider the positive factors of your current job. You already know the location of the bathroom and the break room, for example. That’s a real advantage in staying where you are, since it will take you months, if not years, in a new job to learn how to go from your desk to a snack machine and back again without GPS.

Once you have determined it’s time to move on, the experts recommend that you “prepare to leave gracefully.”

“Wrapping up things well before you leave will help you preserve the professional relationships you’ve built and boost your reputation.”

Fortunately, for you, there’s nothing to preserve.

The professional relationships you’ve built with the lunch bunch at The Kit Kat Klub will last forever, as will your reputation for coming in first, second and third in the annual speed-eating contest, Buffalo wings division.

To these people you are an immortal.

You are also advised not to brag about your “flashy new title or big salary,” which shouldn’t be difficult since you are probably getting neither.

A final consideration is to “prepare for a counteroffer.”

Prepare all you like, but the most likely result of the announcement that you are leaving is the sound of high-fives echoing up and down Mahogany Row.

Your co-workers will be happy, though, because they’ll finally have the answer to a question that has plagued their own analyses of their own employment situations.

If you can get another job, anyone can.

Bob Goldman was an advertising executive at a Fortune 500 company, but he finally wised up and opened Bob Goldman Financial Planning in Sausalito, California. He now works out of Bellingham, Washington. He offers a virtual shoulder to cry on at


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