A witty column about the genuine, emotional, and humorous exploits of coaching elite executives.


Remote Work Is Not For Executives

empowerment job search strategy leadership

Another Thursday, another layoff. 

The stock market jumps 750 points as we gamble on FED rates bumping 75 points instead of 100. Yet, inflation scorches 9.1%, single-family homes top $2000/mo, and now a hellscape of scorching temperatures matched with COVID summer is prepared to bend you over.  

Something’s got to give. And if you think otherwise, you’re likely in such a position of opulence that you’re blind to the struggles most of America is experiencing.

But maybe ‘they’ are right. Maybe there is nothing to see here—calmly waves a hand of blind obedience with a smirk of a Machiavellian gaslit smile. 

I may simply be bitter because I spent $9.50 on a piece of bread, one slice of (unmelted) cheese, and two pieces of ham—that was presented with a card reader and quivering puppy-dog eyes recommending a 22%, 25%, or 30% gratuity. Then I waited over an hour for the pleasure. And that is in rural Montana—not New York City.

Pardon my f-bomb, but what the fuck is going on here? 


Reduction in force? More like a reduction in FUN

Let’s just say, the economic climate is highly sus. And while I have been known to enjoy my fair share of doomsaying, I’m not wrong. Anyone telling you otherwise is either selling you a house, asking for your vote, or simply stupid.

You need to cover your ass and protect your family during this market fragility. 

And for many executives, the market has already shifted from employee to employer-driven. The rules are rapidly changing—and that means less work-from-home fun in your future.

Are you prepared to sack working from your ski-town condo to head back to the city to maintain your career and competitive edge?


Are you hiring an executive or two kids in a trench coat

In the not-too-distant past, the executive ideal was clear.

Confident, dependable, sharp-dressed, well-respected, and highly regarded. A leading executive walks into the room and changes the temperature. A leading executive is flown around the world to domineer a gravitas that cannot be denied. A leading executive has a paycheck that can be paid back in spades.

Now? Replies are hazy, try again later.

An executive can be three minutes late to a Zoom meeting with business up top, a party under the desk wardrobe. Bouncing a baby, doing dishes on calls, randomly having their spouse’s grocery-getting Bluetooth routine hijack a meeting, and over-apologizing for a yappy dog. 

Many modern executives have a paycheck that can be stripped as a line item to please investors without a moment of pause or a shred of compassion. Welcome to the Summer ‘22. 

All this chaos begs the question: is remote work as we know it really intended for executives—or reserved for middle managers and individual contributors?

I can hear the disdain already.

“But Jacob, do I really have to go into the office? Remote work is just as good, haven’t you heard? You’re just not doing it right. It can be done.”

No. It’s not the same. 

Remote work is not remotely as professional, especially for executives. Our expectation of work quality has diminished so greatly that simply showing up to the office is the newest overtly try-hard trend.

We’ve set the bar quite low. And there is a sizable opportunity for merit-worthy executives to make a stand against the competition in this remote chaos.


Office, remote, or hybrid? 

Let’s say it’s your money and you’re about to invest $500k a year to hire someone to help you build a dream. Your livelihood is on the line. 

200 executives with indistinguishable yet equally-qualified experiences compete for the opportunity to be the one you depend on. How do you narrow the candidates?

  1. Evaluate the executives willing to be always 100% committed.
  2. Evaluate the executives willing to be sometimes 100% committed.
  3. Evaluate the executives almost-never willing to be 100% committed.


I’m Jacob and I’m a career contrarian 

I know I’m not making any friends with this line of strategic career thinking, but reality never cared much for personal feelings anyhow. 

If you’re considering a big-time transition this year, I implore you to consider standing out from your competition by bringing your executive x-factor back into the office more frequently or be prepared to get beaten out by someone who will.  

Want to speak directly with me about your career? Contact me below.

Contact Jacob

Get the latest executive career insights each Thursday.

“I get a lot of newsletters. I skim most of them. I read to the end each time I get one from Jacob. Sign up, you won't be disappointed.”

You're safe with me. I'll never spam you or sell your contact info.