Redefine Your Executive Job Search Expectations

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Whether cramming for finals, dropping the 60th edit of a presentation while pre-boarding an international flight, or any other method of (often self-inflicted) midnight oil-burning rituals—one thing is certain—many executives have become habituated to hellacious demands and an expectation to always to be doing something more of themselves. 

Often this starts in childhood (maybe from overbearing parents, hmm hmm?) and continues into perpetuity or mental breakdown. Whichever comes first. 

I digress.

What happens when the executive mentioned above finds themselves out of work? 

Perhaps you are that executive. Maybe you are out of work right now.

What do you do if you’ve grown accustomed to the grind but no longer have anything to grind? Who are you? What is your identity? Do you really have to do all the menial and laborious busy work to get a job? Yuck-o.

Indeed, you must be doing something meaningful with your time; otherwise, your head will explode from all this free time you’ve found yourself with. After all, looking for a job is a full-time job, they say. And nobody is better at working your ass off than you. Right? 

So hop to it. 

Here’s your day one job search checklist.

  • Doom scroll LinkedIn. 
  • Hire a coach. 
  • Pay for a resume rewrite. 
  • Sign up for infinite job alerts. 
  • Take a class. 
  • Refresh the job board again.
  • Score an interview—but get ghosted.
  • Learn that some other expert says your expensive new resume is trash. 
  • Be told to create pedantic LinkedIn posts instead. 
  • Realize you have nothing meaningful to say.
  • Feel dumb.
  • Reach out to an old work friend. 
  • Finally, realize your friends are useless, and you’re screwed. 
  • Wallow in despair. 

What does day two involve? 

Surprisingly, for many, it’s often more of the same. 

Rinse and repeat for 6 to 9 months before frustratingly taking a job at 35% less pay to end the misery of spending 50 hours a week painstakingly following up and conducting menial process work to get calls. 

Fun times. 

I know what you may be thinking now, “Jacob, you’ve read my soul, but what’s the remedy, Mr. career guru man? I need work now!”

First, you’ll need to understand how you ended up in this situation and set the right expectations for your performance. Otherwise, you’re cursed to find yourself doing this again before you know it. 

Your Job Search Expectations Are Jacked Up

I’m likely biased toward pessimism here—or perhaps unlucky—but some sum much greater than 50% of executives I speak with have significantly underestimated what it takes to find meaningful, career-forward momentum, and rewarding executive employment. 

Note that this is different from ‘just a job’ to pay the bills. I’m talking about an opportunity and role you get fired up about—not settle for in defeat. 

Too often, I hear executives target a 2 – 3 months transition time. Perhaps this is plausible if you’re already interviewing—and honestly feel enthusiastic about the opportunities you’re exploring. 

But most that I hear from are less fortunate. To be fair, you probably wouldn’t call me if you were happy with what you could generate on your own; therefore, my perspective is highly biased. 

If you find yourself in the camp of the less fortunate—yet still naively optimistic regarding your transition timeline—you may not like reading this. 

Truly kick-ass executive work can take a year to foster. It could be longer. 

It really depends. How many irons have you kept warming in the fire for the last five years or so? 

Oh, none? 

Well, shit. Your search is likely to be more complicated than you think. 

Depending on your financial circumstances, you may not have any legs to stand on for an extended executive job search.

You may need to take a filler job to stem the financial bleeding of being out of work while you prepare to find something more fulfilling next. 

Remember, beggars can’t be choosers. 

The mistakes that hinder your job search (and negotiation leverage) today were made years ago—when you either didn’t foster the right career-defining relationships, didn’t build the financial nest egg necessary to sustain your chosen lifestyle, didn’t diversify your revenue streams, or didn’t prepare for the reality of a tightened market, heated competition, extended periods of unemployment—or the slew of other challenges executives face in transition.

Why does this happen?

Is this because many first-time executives are transitioning and must figure out what to expect? 

They were promoted into their roles, have limited knowledge of transitioning to their new level of seniority, or have an elevated/vanity title and don’t truly possess marketable executive skills yet. If this is you, you’re entering uncharted territory. No hard feelings!

Or is this because job search differs from what it used to be in the old days? A firm handshake, mailed resumes, and a starched collar no longer cut it. All the new processes and tools may feel foreign. 

Or all these tight-wallet whipper-snapper founders hate the aged and their seasoned experience—and don’t want to pay what’s fair!

Whatever your reason, you need a pragmatic solution to fix your chapter-turning career moment. 

So here goes.

Do Less. Play A Longer, More Intentional Game

Like many things in life, doing more isn’t always more. 

There are diminishing returns to obsessive job search activities, which can take an emotional or psychological toll on anyone out of work for an extended period. 

No matter how many alerts you set up or jobs you apply to and what pace you aggressively pursue new opportunities, the market stays the same. 

There are a limited number of compelling executive opportunities. Tomorrow, there will still be a limited number of compelling executive opportunities.

Depending on how specialized or niche your experience—or how specific your industry, location, or other search demands are—it could be a week or two before another compelling opportunity pops up.   

That’s a lot of doom scrolling, refreshing, and thumb twiddling. Or waiting for that rewarding triggered dopamine hit of an email notification from a recruiter, only to immediately scoff and realize it was a LinkedIn notification for someone selling you lead generation services.

No matter what you do, you cannot change the reality that there are a small number of opportunities and many people chasing them. (You can create your opportunity elsewhere and pursue other avenues for money, but you can’t control the creation of awesome jobs in most cases).

In other words, you can’t outwork your job search. 

So chill out and stop kicking your own ass for not landing a job sooner—even if your peers have. 

Hell, your peers may not even be happy with the job they took; they may simply have too much pride to tell you. They may be masking.

I’m not suggesting giving up. 

But instead, rather than hammering away 50-60 hours a week to grind out a job, focus your work on 20-30 meaningful hours of search only. 

Schedule 2 days off to be with your family, enjoy a hobby, or go for a walk. 

I’m talking, no phone, tech, or checking email to see if that recruiter stopped ghosting you. 

There are two good reasons why I’ve found this strategy to be effective. 

1) Most executives work to the bone, and time off is a new concept. 

Forcing a lighter work week can help you discover new hobbies, form a new appreciation for your family, fall in love with a book, or find joy in ANYTHING BESIDES WORK. 

2) Your time becomes even more valuable. 

I didn’t expect this to work, but it does. I hold sacred two days a week when I don’t engage with clients on the phone. I found two things from this that I also promise apply to your job search.

First, I spend more time with my wife and son on those two days. I love that time more than anything. It would take a lot of money to convince me to break that time away, so I value my time much more, increasing my perception of how much my time is worth. 

I’ve found that your value is capped less by what someone is willing to pay and more by you—and what you think your time is worth. So you must learn to value your time, even when you’re not working.

Second, I need to fit all my client time into three weekdays. That makes my calendar exceptionally tight and always in demand. I used to book 10+ calls a day, five days a week. Great for learning quickly—but terrible for sustainability and mental health. By forcing my calendar into three days, I added a big squeeze on those 50+ calls I would typically schedule. My clients not only valued my time more as I did—but they began respecting my time much more as well. The quality of the conversations we had significantly increased. 

In your job search—if you’re lightning quick to get back to a recruiter or hiring manager—you’re making it too easy on them. As a result, you may come across as desperate. 

Your sense of urgency to find work only sometimes matches the employer’s urgency to hire. You cannot make yourself that easy. 

Take a day to respond to inquiries. Be less available. It can make you more attractive. Consider adding a polite reason when you respond to drop a hint that you value your life or are in demand from other suitors. 

For example: 

“Thank you for bearing with me. I was out of the office camping with my family in the Redwoods. I’m available to connect on Friday. Does noon work?”

Something like this indicates that you have a life, and they should respect it if they want to hire you. 


“Great to hear from you. I am keen on learning more about the direction of leadership that you need, and I suspect that XYZ COMPANY is my leading choice if given my pick! Thanks for bearing with my delayed response. I was at an onsite interview downtown and heads-down in meetings.” 

Something like this indicates that other people are considering hiring you enough to bring you onsite. They may need to speed up the process if they want you.

In short, your job search isn’t going to implode if you take time for yourself and your family. Yes, that even applies to workaholics like you and me.

So schedule a day or two off each week. Then, hold your time sacred and do literally anything else but look for work.

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