Sinking forward

It’s been almost six weeks since my last post. As mentioned in October, I’ve been losing motivation on pretty much every front. Even updating this journal has become a chore.

Job Search Update *** 

The good fortune of my wife finding a job in Chicago did simplify my job search. I can now focus on one geography. So, in early November, I pushed hard to find a local position. After a few hundred more resumes, all I got was a handful of rejections. These ‘no’s’ included a few jobs I figured were ‘lay-up’ interviews. Now I know for sure that such thing does not exist.

After spending some time reading about job searching for more senior professionals, I’ve made the following changes, followed by explanations:

  1. Gutted out my resume leaving only a few straight-forward factual statements;
  2. Taken my academic graduation dates off my resume;
  3. Placed more focus on cover letters.

Many of the jobs I apply for are mid-level. Higher-level positions usually don’t have any postings as they are conducted through executive recruiters. Therefore, most of the positions are mid-level. The only chance to maybe get an initial interview is to tone down my resume to read more like what they would look for in these positions.

At this point, you may be asking … “why don’t you just contact the executive recruiters then?” Well, (1) executive recruiters ignore unemployed people because they know you’ve sent your resume to everyone in town. They don’t want to be in the position of getting you an interview that turns into a job then have the employer tell them “well, we can’t pay you because we already had this person’s resume in our system.” (2) Frankly, you just don’t look like a good candidate — it makes it look to their clients like they are reaching pretty far to find candidates. A headhunter always wants to convey the appearance that they have a deep database of great candidates to pull from. (3) Adverse selection. If you were worth wasting time on, why hasn’t someone else done so already? No one wants to prove the fool.

I took the academic dates off my resume in order to hide my age. Ageism is real. When submitting a resume to many jobs, it is initially caught by an applicant tracking system or (ATS). These programs filter out resumes that don’t fit the guidelines of what the hiring manager is looking for.  Like it or not, these systems look for graduation years to back into candidate ages. Many hiring managers don’t want applicants that are older than the people they would report to. Therefore, you get blocked out before a human even reviews your credentials.

When using a resume that included my dates of graduation, I began to detect a certain pattern. Similar online application programs would send out similar rejection emails at the same time the following morning. This is not a coincidence. It’s the automatic ATS screening out “non-fit” candidates. Therefore, one needs to try to work around these systems.

Lastly, I’ve begun to put more work into customized cover letters and the faces of emails I send out. I try to demonstrate better what I could offer for the position. I also try to show that I know the industry, company and/or person I’d report to well.

With all of this said, overall, I have not really witnessed any better results. I can only say that I’ve received a couple of more personal rejection notes.

Lastly, I’ve revisited networking to try to wedge into several interviews. This only resulted in awkward calls and emails. In one circumstance, due to a misinterpretation of a conversation with a hiring manager, I was told that I had a good chance at getting an interview for a position and should aggressively follow up. This only resulted in an embarrassing and cringe-worthy situation where, long story short, I felt like a stalker. I wanted to dig a hole and jump into it.

So… basically, the job search is a giant waste of time. I’ll keep pushing for a few more weeks until year end just to go through every major employer in the Chicago-land area. At this point, I’ll need to move onto focusing on something entrepreneurial. Its just not worth spending more time on this as its clear there is absolutely no market for my skills. Its only leading to deeper levels of depression.

At this point, I no longer have any hope in finding a professional job. I also have no confidence in my ability to keep a job. I truly feel like a fraud that will be quickly discovered just a few weeks into any position.

NYC Apartment Selling Update ***

No good news here either. I’m still heading to NYC almost every weekend and sitting here alone hoping a buyer shows up at one of the many open houses. I’ve had a few people call and say they would be sending an offer…. then, nothing. Just silence. When I try to follow up, more silence.

Looking back, I wish I just had silence instead of these few fleeing glimmers of hope. Not only did they lead to despair but they also caused me not to lower my price.

Tomorrow, I’ll be taking the apartment off the market. I cannot be here next weekend and I there is no sense in keeping the clock ticking during the holidays. The listing is already stale but why make it look ancient. I’d rather stop the clock and restart it in February when the supposed “selling season” is here. I need a rest from it anyways. Sitting here alone, I feel like a prisoner in the bad decisions of my past. Its hard to move forward in any way with this ball and chain around my ankle.

Once I re-list in the spring, I’ll lower the price. If it still does not sell, I’ll drive down the price like a manic. I need to get rid of this piece of shit and just move on with my life. The financial loss just isn’t as bad as the psychological pain this place is putting me through.

Overall Finances ***

Perhaps the largest event over the past month has been an end of my unemployment benefits in mid-November. Losing this $450 a week hurts. In fact, its terrifying.

Outside of my time as a student, I can’t remember a time in my life where I made zero income.  This is a heavy weight on me. From morning until night, its hard not to constantly think about this.

I’ve cut down my discretionary spending to almost nothing now. I purchase just enough food to get through from day-to-day. I watch the unit prices on everything I buy. I think twice about every purchase. I truly understand what it is like to be poor – how painful it feels day in and day out.

I have no idea when any money will flow back into my bank accounts. I’m considering taking part-time work at night or over weekends. At this point, I just need some money to cover my own overhead expenses. I no longer care how humiliating this seems. To be honest, I’m not even sure I can get a part-time job, let alone keep one.

When I was a freshman in college, I worked at a sporting goods store. I was surprised that there were a few older co-workers who actually had college degrees and who were professionals before becoming retail employees. The manager of the store had a masters degree from the same top 10 school I got an MBA from. Anther assistant-manager had a similar masters degree. I remember them saying that the recession caused them to need to find any employment. For the past 25 years, I’ve looked back and felt that I’d never be in a position like these guys. Well, here I am. Probably in an even worse position as they were a bit younger than I am.

My advice for anyone who underestimates their job: learn to put your best foot forward. Don’t assume that a good job will always be there waiting for you. In fact, you may be walking on a thin surface with a long fall underneath.


My health continues to fade. My weight has been fluctuating up and down about 10 pounds. I don’t eat well. I’ll go long stretches without an appetite then suddenly I’m constantly starving. I’ve now gone four months without a drink. As I read, I’m now craving sugar pretty badly – likely from lack of alcohol. The constant candy has led to me putting on weight. Then I feel disgusting and I starve myself.

My back and my leg hurt about every three days. My sciatic nerve flares up quite often. I don’t know why.  I get migraines at least once a week, almost exclusively when I am in NYC. I don’t seem to get them in Chicago.

My son ***

Adding to the long-list of ‘shit gone wrong’, my two year old son is falling further and further behind his peers. This was observable already earlier this year. Other children his same age would be following instructions but he was off in his own world. His language is behind. At first my wife and I believed if we put him into enough classes, he’d catch up. Instead, he’s just falling further behind. We have state-appointed therapists overseeing him a few times a week now. They seem just as puzzled by it as we are.

My dad ***

My dad turned 92 years old this fall. Since his birthday, his health has been rapidly falling apart. He’s been in and out of the hospital a lot over the past month. Just this week, he came down with pneumonia. I worry that he does not have long left.

Unfortunately, my dad is quite disappointed in “how I turned out”. He complains about me constantly. He is very perceptive and knows I made some dumb choices. He’s never quite understood me though. He’s always envisioned me as a person that I’ll never be. He thinks that by my age, I’d be in top management at some corporation or a partner at an auditing firm. He’ll never realize I was never meant to be an accountant or an executive at a corporation. Its just not who I am.

So, unfortunately, as his health fails, its hard for me to spend much time around him. Within minutes it turns into him scowling at me, openly disappointed. He’ll inevitably say I chose to become a gambler and gave away a great career (he just doesn’t get that I was on my way towards fired at an investment bank as well and that I never had a long career there either).

In Conclusion ***

Its hard for me to say anything good is happening. Every week feels like a low point, only to sink further the following week. Whereas most of the events I’m living through in isolation would really impair someone, at this point, I’m just numb.

Over the 18 months of unemployment, I’ve learned the following:

  1. Don’t get excited about anything. It’ll inevitably lead to false hope. The more excitement, the more eventual disappointment.
  2. Don’t over-think anything. Just keep walking forward and going through the steps.
  3. Avoid too much socializing. Hanging out with people, social media, phone conversations, emailing– pretty much all of these may feel comfortable while participating but almost always lead to pain … hurtful comments are easily received, envy of others grows, etc. Its best to just stay isolated for awhile — spend time repairing yourself — or, if necessary, spend time helping even less fortunate strangers.
  4. Try to get exercise and keep the endorphins working — its the only thing that helps with the depression. Watch a good t.v. show or movie every few days but don’t just sit like a mummy in front of the t.v.
  5. Save every fucking penny – no unnecessary spending — no trips, no clothes, no pricey amusement, no cabs, no dry cleaning, no restaurants and absolutely no bars.
  6. Its better not to drink. The mood swings are not as dramatic. Also, it saves money.
  7. Find the rope that pulls you out of the hole. For me, its reading investing literature from a handful of old value guys. This makes me feel better for some reason. If it were not for this, I don’t know what level of depression I’d be in.
  8. Stay humble. Don’t express opinions. No one wants to hear your thoughts. You’re irrelevant – like it or not. Don’t look down on anyone. Before you know it, you’ll realize they look down on you.

Happy holidays.

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