As a twice-divorced 56-year-old male on the dating scene for a nice similarly aged woman, I can safely say that dating and job search are incredibly similar. I was laid off in 2007 after the market crash and found out firsthand how difficult job search was.

My last relationship was some time ago. I’m a well-mannered, well-educated dude with my baggage under control. I have a great career coaching business and volunteer with local organizations. I’m a caring father and overall, a nice guy. Recommendations from my ex-wives are not available.

Why can’t women see that? Do I need to print this on the side of the Empire State Building? Why do I keep meeting the wrong women? Am I relationship cursed?

I feel bold enough to share some of the frustrating parallels between job searching and dating, particularly the dating process.

Inherent discomfort

Job search and dating can evoke uncannily similar thoughts and feelings:

• I don’t want to, but know I need to since…
• I feel awkward, weird, vulnerable, and insecure
• How do I explain _____ and _____ at my age?

For the 2 “___” above, I could fill in two painful divorces, a resume gap in 2007-2008, a receding hairline, resigning from my last full-time job in 2017, being single for so long, don’t make as much money as I used to; fill in with your own shortcomings.

I feel like after 2 marriages, I could be seen as damaged goods. Besides, going back for a third time is just a headache. Why should I even try again? I’m comfortable with just me. Do I really need a new love?

Yes, I do, since love is the only thing that really matters!

I spent 15 years in investment banking from 1993-2007 with a 9-figure comp, only to be laid off. I had every insecurity in the world at that point. Depression, anxiety, psychosis… I had them all.

For you, maybe you ask Why don’t Morgan Stanley, Google Pay, or Venmo want me? I can help them grow. Why don’t people understand the value I bring to the table? What’s wrong with them?

Other than death, can you think of anything else that evokes so many feelings as dating and job search? Sometimes, I think dying is easier (never died so I’m no expert). Both bring out insecurities that can date back to your childhood. Is there a therapist out there that combines job search and love therapy?

Why does it take so long?

When dating, it’s important to plan and consider where to go, what to do, and exactly how simple to keep it. Even with a plain coffee and a walk, the choices and considerations still abound: what café? What neighborhood? How long to walk for? I wonder if my sports coat over my jeans is the right look. I plan, then plan, then plan. Aaaaah!

Looking for the right job is practically a full-time job in its own right. Gin up your resume and LinkedIn profile. Start networking and keep networking. Interview and tell your story for the 15th time. Perfect your strengths and weaknesses. Read here for my tips that you can begin right now to fast-track your job search. 

Short term fixes don’t really work

Dating a 25-year-old woman at the age of 56 sounds great for me. Picking up a woman at a local bar. Great in the short term, but do I really want that? In your job search, you could hop to a competitor to do the same job for 50% more. However, will that really move your career forward?

No instant gratification

If the world revolved around me, you would find out about a second date at the end of the first. Sadly, that is not how things work. I can’t ask out a woman at the end of our first date; she could say “yes” just not to offend me. I have done this before, and when I call back 2 days later, I realize her “yes” was just pity.

Let’s say I have a first date, and we seem to connect. She laughs at my jokes which is really great since I’m not that funny. Eye contact, smiles, love the same movies, oh yea! Then I play it cool and wait, because I don’t want to come across as desperate. I want to play hard-to-get a little bit, because apparently that’s what you’re supposed to do.

At least at the end of an interview, they tell you if you got to the next round…Oh, wait, that’s fantasy. You know that interviews are like black holes. You connect with an employer, have a great conversation, and hang on. Just hang on. Just hang on Snoopy, Snoopy hang on (free resume review for identifying the original band who sang that song). The system is so broken that you rarely even hear a “no;” just ghosting. Even if you hear a “yes,” it’s weeks, months later. Wouldn’t it be nice if a company told you at the end of your first interview if you made it or not?

Talk about cruelty.

Sometimes you get some traction, but then nothing

Things seem to be going great with this new woman I met online. Three solid dates: a walk, lunch, then theatre. We even kissed and talked about going away together. All is good…until the music stops. She doesn’t return my calls, and I get one-word text answers if I’m lucky. Did she go back to a former lover? Do I really kiss that poorly? The crickets are chirping, and I’m stumped and pissed. I call her every name in the book.

You made it to the 3rd round interview with Goldman Sachs or Coinbase. You did it by the book and prepared for your prior 7 interviews perfectly. You did all your research, covered all your bases, spoke to lots of people at the companies. Then nothing… nothing! The momentum dies. You call HR, even check in with prior interviewers to get some feedback. You still hear nothing, and all you can do is walk away with feelings of defeat.

Risk, vulnerability, and fear

Putting yourself out there for love is really hard. I like certainty. I don’t want to make myself vulnerable and risk having my heart stepped on. I was married twice for 10 years each time. I like the long game. I may not have liked my marriages after a while, but I knew the dysfunctionality to expect.

In that way, job search and dating are similar. Many of my clients have been with the same company for 15+ years. They know the people, the environment, they know how things work; it’s comfortable. Moving to a different company and needing to prove yourself all over again is a huge risk. It’s like being a freshman in high school and having to learn everything from scratch, from class material to social hierarchy, all while getting slammed into the lockers at least twice a day.

Changing to a new company and a new role is even harder since you are thrown into completely new territory. Sometimes, though, this is the best tactic for your long-term career. Move and grow or else.

Both dating and job search demand putting ego and feelings on the line. Even though there is a strong desire and a goal at the other end, it is often tempting to stay put, stay small, and maintain the status quo rather than risking pain. However, hide the pain and it often comes out sideways. Like fighting about who will get the wagon wheel, the stupid looking wagon wheel.

Oh, and did I mention the lies

Nobody I’ve met looks like their O Cupid picture. Everyone on Match does yoga and is in perfect shape. Everyone claims to be 35 years old and appears to look like Susanna Hoffs from 1984 (If you just said “who?” we can’t work together). Nobody claims any neurosis. Everyone’s grown kids are well-adjusted and Nobel scientists. Nobody has ever been to a therapist since their lives are perfect. Where is the truth?

Every online job posting is accurate, well-written, describes a real job, and only you know about it. Right? However, little did you know that:

• It is estimated that 50% of job postings are fake since they are pre-filled, either by someone internal or by an already identified external candidate
• Another 25% of the job postings are just stale since companies pay job boards less money to keep jobs up longer
• Therefore, 75% of the jobs don’t really exist

As Elaine Benes would say, “Fake, Fake, Fake.” Identify that episode for a free resume review.

Even if the job posting is real, it hardly describes the real job. You could drive a truck through the general wording of some jobs (Amazon in particular). Others are so specific and technical that nobody can possibly have all the skills mentioned. They want 25 years of financial services experience for a recent graduate. They want 100 years of machine learning experience in addition to deep product knowledge of algo trading. Come on!

There’s good news though…

Despite the pain of looking for love, if you look hard enough, you will find it. I found love twice, before and after my first marriage. It took years in between, but it finally came. Did I freak out, worry, and almost jump out a window? Sure. Love takes time. However, I still have some hair, exercise sometimes and try to keep my weight down. Love will come!

A job that moves your career in the right direction will come also. You need a career plan that is well thought out, organized, and has realistic timeframes. You need to execute the plan and stay the course, sometimes with help of a professional.

Love like job search; the process is horrible but there is hope for a happy ending.

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