This is a personal story….

I’m 55 years old and have been married and divorced twice.  I’m healthy and have the best profession in the world. I’m no Robert Redford, but certainly presentable. I bike 4 times a week, so I keep in shape.

My hair has stuck with me (how?), but I don’t think women care about hair, do they?

Neurosis?  Sure, I have my share. For the full picture, you can call either one of my ex-wives at 867-5309 and ask for Tommy (Free resume review if you get the reference).

Starting the dating process yet again feels so much like starting a job search.  I don’t want to, but know I need to.  I feel awkward, weird, vulnerable, insecure. How do I explain 2 divorces at age 55?

Here are the top 5 reasons why my dating and your job search are essentially the same.

#5: It takes sooo much time

Dating takes so much time.  Where should we go, what shall we do? I spend so much time planning. I try to keep it simple like a coffee or a walk.  However, what restaurant? What neighborhood? Will I look cool?

If we have a coffee at 3, can I turn it into dinner at 6, drinks at 9 …well you get the picture.

I’m exhausted thinking about it. I might as well hide in my career coaching job since I know I’m pretty good at it.

Job search is also a massive time sync.  Gin up your resume and LinkedIn profile (5 hours). Start networking (10 hours) and keep networking (20+ hours) until you secure that coveted spot.

Looking for a job is a full-time job!

#4: No Instant gratification

Maybe she and I will have a connection.  Even if we get along really well on a 1st date, I never go for the kiss. So, I wait until the second date.

I don’t want to wait; I feel lonely and have so much to offer.  When I see a Facebook post by a friend celebrating 30 years of marriage, I reply “You’re supposed to stay married?” I joke not to feel.

In my opinion, 2nd dates should follow 1st dates with 5 minutes in between.  Just enough time to change shirts, refresh the mouthwash, and breath to calm my heartbeat.  I don’t want to wait; I just want to bang on the drum all day (another free resume review if you get this one).

You always get immediate feedback after a 1st interview.  You don’t wait 3 weeks.  Potential employers actually treat you like a human being.  Wait… no..

Interviews are like black holes. You connect with an employer, have a great conversation, and hang on. Just hang on. Just hand on Snoopy hang on.

Why is the system so broken that you rarely even hear a “no”? Even if you hear a yes, it is weeks, months later. Talk about cruelty.

#3: You have great momentum then… nothing

I would think after 3 great dates, I would get a 4th (I’m in the hypothetical now since I haven’t even started).  The conversation is flowing, I seem like a great guy since I help people for a living, earn their living.  She laughed at my jokes: with me, not at me (I think?)

Then the music stops.  She doesn’t call back.  Did she speak with either of my ex-wives?  I certainly hope not. I don’t get it.

You made it to the final round with Goldman Sachs or Coinbase.  You did it by the book. Practiced for your prior 10 interviews.  Did all your research, covered all your bases. Then nothing. Nothing!

Then the momentum dies. How is that possible? You call HR, even check-in with prior interviewers to get some feedback.  You still hear nothing.

#2: Taking a risk is scary

Putting yourself out there for love is really hard.  I’m scared since I feel so vulnerable and unsure of myself. I have not dated in 15 years. Let’s face it, my track record is not great.

I like certainty.  I don’t want to take any risks and have my heart stepped on.

Many of my clients have been in the same company for 15 years.  Changing to a different company and needing to prove yourself all over again is a huge risk.

However, changing roles with a new company is even harder since you are thrown into something really brand new.

#1: Dating apps and online job applications are worthless

I have tried dating apps. Nobody looks like their picture.  Everyone does yoga and is in perfect shape.  Everyone claims to be 35 and appears to look like Susanna Hoffs from 1984 (If you just said “who”, OMG).

Where is the truth?

Nobody claims any neurosis. Everyone has well-adjusted kids (remember I’m 55) that don’t need a lot of work. Nobody has ever been to a shrink since their lives are perfect.

Everybody likes to take a sunset beach walk. I don’t like walks on the beach at any time.  Too many flies; too hot; the smell of saltwater makes me think of … nothing pleasant.

I wish I could just say in my profile “Nice 55-year-old man in decent shape seeks same age women with as many life’s scars”. Should I?

Every online job posting is accurate, written well, describes a real job, and only you know about it.  Right.

50% of job postings are fake since an internal candidate or an already identified external candidate has the job already.  25% of the jobs are just stale since companies pay less money to keep jobs up longer.

75% of the jobs, therefore, don’t exist. Fake, Fake, Fake (thanks Elaine).

Bottom Line

As I begin this process called dating, for the 3rd time in my 55-year life, I can’t help but feel, really feel my client’s pain.

Click for our Weekly Report on People Moves from the Street to FinTech

Sign Me Up