Starting Over at 59

Confessions of a GenX Black Man navigating depression, financial insecurity, exhaustion and lost love

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  • Tues Nov 4 2025

    Yesterday was a rough one. I’m now substitute teaching just to keep busy and bring in some additional money. I really enjoy the kids (elementary school) and the fkexibility enables me to continue the food truck/catering business. I’ve dialed back the number of events to be more reasnable with the teaching. Last night I didnt have a pop up event for the food truck, so it was time to prepwhen I got hime from the school.

    When I finished cooking for the night, I like to watch TV for a while and decompress. I also unfortunately scroll through social media. It was then I realized my most recent ex had blocked me on Facebook. This immediately sent me into a tail spin. I wound up having more evening cocktails than normal, and eventually started stalking her on other platforms. I discovered she hadn’t yet blocked me on TikTok, So, I proceeded to peruse her recet posts. This contoinued until oh, about 2am… not good.

    I’m not a TikToker, so in the light of the morning, I deleted my TikTok account. I need to make a conscious effort to limit alcohol intake and social media use during this transition time.

  • Health & Weight

    Getting old sucks. If I’m being honest I’ve been “getting old” since I was 40. At 40 I tore and had surgically repaired my right meniscus. Due to an astigmatism, a had to start wearing glasses. Then the coup de grace, high blood pressure, high cholesterol, and…. Diabetes.

    So now I’m 40 with Type 2 Diabetes. I wasn’t surprised. I’ was a walking risk factor – black male, seriously over weight with family history.

    For almost 20 years I’ve attempted to manage the diabetes with medication alone, rather than make significant diet and exercise changes, with mixed results.

    At my heaviest I was 350 (at 6’2”). But the diabetes was getting more difficult to manage the older I got.

    I love good food and drink. Fortunately (or unfortunately) many of my jobs afforded me the opportunity to travel and entertain clients and/or staff.

    Diets didn’t work, or at least not for long. And exercising really wasn’t an option for me. With the arthritis and neuropathy getting worse, not better something drastic had to be done.

    In the year between two rotator cuff reconstructions, I had bariatric surgery. Gastric Sleeve to be specific. This is when they remove 3/4 of your stomach to force you to eat less.

    It worked. At least at first. I lost 80lbs in the first 6mos. Easy peasy. but I missed eating and drinking. Like any good dyslexic, I figured a way to still enjoy my indulgences. I just had to limit the portion sizes, and I’d be good. Yeah, OK. If my ability to portion control wasn’t a problem, I wouldn’t have needed the surgery in the first place. Then there was the side effect of eating anything you wanted…. Google “dumping syndrome” when you get a chance.

    My weight fluctuated up and down by 50 lbs over a 3-4 years span. Naturally my diabetes didn’t get markedly better either. Eventually, I was prescribed Ozempic – for the Diabetes. But I also helped me to reduce the weight.

    Fast forward to 2023. I’m down to 240, low enough to have the knee replacement surgery I’d been putting off. Through rehab, trying to be conscious of portion sizes (if not food quality) and the Ozepic, I’ve been able to maintain for nearly 2 years. As of Nov 2025 I’m holding at 235. And frankly I’m probably holding 15-20 lbs in loose skin from the weight loss still…

    With no FT job, (healthcare benefits) it’s difficult for me to continue my medication regiment as consistent as I have. I’ve not had the Ozepic or several other meds in nearly 2 mos. I’ve also not seen my Endo specialist since last November.

    I need to look into Medicare. I need something less expensive than what I’ve been paying as an independent consumer.

  • Career & Job Search

    1993-2000

    Upon moving to NJ I accepted a job as an Account Exec (sales) for an IT staffing firm owned by my “brother-in-law candidate”. He quickly became my mentor and taught me the staffing business well. He took good care of me and I was earning more money than I could have ever imagined. 9 years and several promotions later, it’s now 2001, I was VP of Consulting Services, responsible for 15 sales reps across 5 offices in 5 different states. Then 9-1-1 happened, and I quit.

    2002 – 2004

    It’s 2002, I’m now 36 with a young family. My mentor taught me well and I decided to take the same leap he did, and start my own staffing firm. Of course my timing was awful. I’m the immediate aftermath of 911 staffing in the NYC metro area grind to a halt, especially IT staffing. I lasted almost 2 years, burned through 90% of my savings, but was forced to abandon the dream. My kids were now 7 and 4, and I now know the financial strain was the beginning of the end of my marriage. She never forgave me.

    I slogged through jobs with 3 different staffing companies over the next 2 years. Under employed ,making a fraction of what I was earning, the stress continued and I kept looking for new roles.

    2005-2018

    I finally landed with company that provides outsourced services to Pharma companies. Now I wouldn’t be “selling” anymore, but still client facing and leading a team of recruiting. I was making the transition from staffing company to client-focused recruiting. I loved it! And the comp package was lucrative! I was back!!

    14 years and a promotion later, I was let go. My company had merged with a complimentary company and there were several redundant roles eliminated.

    Now divorced, remarried and with mortgage and alimony payments to choke a horse, I was 53 and unemployed. As a recruiter, through the years I had interacted with several “seasoned” candidates. They struggled to understand how, with 25+ years experience and a great track record, they couldn’t get another job in their field of expertise. Sitting as I was between the candidates and hiring clients, I knew the reason. Clients can hire candidates half the age of these professionals at a fraction of their salaries. Why pay that much for someone on the backend of their career, when I can get “the same” results with someone who costs peanuts and they can mold to their will. It was a no-brainer.

    2019 – 2023

    Now it was my turn. Let go in August 2018, it took until March 2019 to land a new role. I was earning less than half what I was, but the mortgage and alimony (and now college) payments didn’t stop.

    Then, a few months later a company I interviewed with months prior called and offered me lifeline. Still less than I needed to make, but this was a Fortune 500, big Pharma company. I jumped at the opportunity.

    4 years and a promotion later, I’m now leading a team of 15+ recruiters spread across the country supporting arguably the companies most important function. But, in those same 4 years I had 5 different leaders. The instability combined with the unspoken sentiment that I was stalled at best or being managed out at worst, made me nervous.

    2023 – present

    As always I kept all options open. Through networking I developed a relationship with a CHRO. We spoke nearly once a month for years. When he called with an opportunity to build and lead a recruiting team for their fastest growing BU. 👀👀 Sure! I’m available!!

    Build a dedicated recruiting team to support this BU – check!

    Reduce reliance on outside recruiting agencies – check!

    Improve KPIs such as time to fill, 0-30 day retention, hiring manager and candidate survey results – check, check and check.

    Didn’t matter – 18 mos later, citing a significant business lull and client loss, I was impacted by a series of lay offs, again.

    Now it’s 2025 and I’m 59. I’ve worked my network, applied to literally hundreds of jobs and managed just 5 interviews in 8 mos. What’s worse is I’m struggling to get any traction for roles for which I’m seriously over qualified.

    Just to bring in some income I’ve started substitute teaching. At $15/hr that is not a long term strategy. But it does offer me the schedule flexibility to continue to ramp up the catering and food truck business.

  • In The Beginning….

    What is this blog about??

    More than just a mid-life crisis, I’ve experienced several traumatic events over the last 10+ years. My therapist has encouraged me to journal as a means to cope. I’ve made the decision to turn this “journal” into a blog. 

    First some truth – 

    Born in March 1966 I’m on the cusp between GenX and Boomers. I’m claiming GenX.

    My Why – 

    I’ve had a very rough last 11-ish years. Spent much more time miserable than happy. I’ve decided to try something new since what I have been doing certainly hasn’t been working. And, maybe there are other men experiencing similar crises. Perhaps sharing my story can help them to not feel as alone as I do now. 

    Some Background

    After 22 years of marriage and 2 kids,  my wife decided I wasn’t enough for her and engaged another man to satisfy her. Weeks of gaslighting led to me questioning my sanity, even spending a few days in a mental facility. Fed up, I filed for divorce and moved out of the house that I was paying for. 

    This was my college sweetheart. Very quickly after the wedding, we moved to her home town in NJ so we could be closer to her family when we started having kids. The unintended (maybe) consequence was that I was disenfranchised from my friends and family (more on this later). 

    Over the years I took on the role of breadwinner and she was the “stay at home mom”. It was fine. I threw myself into my work with the sole focus on providing for my family. 

    I made good money, really good money. Enough to buy a 4100 sq ft house in central NJ with 2 acres of land. EG – not cheap. 

    Over time, we grew distant. I travelled more for work (sometime on purpose). On family vacations I took conference calls instead of spending family time. Sex was non existent. My myopic life led to a fracturing of our relationship. We grew apart, the love left, and I acknowledge that it was mostly my fault. 

    In 2014, my mother was suffering from ALZ and died in the spring. While I was in the throes of that trauma, my wife began a relationship with another man, someone she worked with. I’ll spare you the details but it was based on a sexual nature that was certainly absent in our own relationship. 

    Never get divorced in NJ. Due to the 22 years in which I was the breadwinner making good money, the court, in an effort to balance the income, assessed me an alimony payment that is more than what 95% of Americans earn. Fine. Whatever. I could afford it. 

    Emotionally though, I was broken. In my zeal to prove that I was still worthy, I jumped way too quickly into a new relationship (and later marriage). She was the complete opposite of my ex – fun, free wheeling, and carefree. And she loved me, desperately. 

    I proceeded to spend way too much money in buying a house that was as close as possible to the size and location as the one my ex wife got to keep (thanks to my alimony payments).

    Then….. I lost my job. It was 2018, I’m 52 years old, making $250K+. It took me 8mos to find another job – now making $85K. Combined with a “non-modifiable” alimony payment, I was financially devastated and filed for bankruptcy. 

    In 2019, I realized why my new wife was so fun and care free – she was an alcoholic. We (sister, friends and me) convinced her to go to rehab, but she only stayed for a week. 

    In 2020, the COVID pandemic hit. I’m now working for another company making more, but not enough, and my job went remote. I decided to get out of NJ. 1) I needed to reduce expenses; 2) maybe a change of scenery will help my new wife’s recovery. 

    So we landed in Newark DE. Back in the shadows of the University of Delaware where I graduated years and years ago. 

    However, things didn’t get much better. Financially things were still tough. My job was fine but I was not making enough to sustain us. And my wife couldn’t hold a job more than a few months since she was still drinking all the time. 

    We started a catering company to try to generate some additional income, but it’s tough for an alcoholic to do anything consistently or professionally, for long. 

    Over time, things got worse and worse and in 2024 a friend convinced her to go to rehab. This time she stayed 30 days. While she was gone, I made plans. When she got out I insisted she stay at a half way house to get herself together. She got kicked out of 2 of them before I filed for divorce. In July 2024 the divorce was finalized. 

    This was the first time in 30+ years I’d been alone. I was miserable and longed for a partner. But, I was building my catering business and started a food truck. My staff encouraged me to get online and start to date. 

    After a few dates with a few different women, I settled on someone new. She was very different than anything I’d experienced (no matter how limited my experience was). 

    I was enthralled. She had a double masters in Education, tatted from head to toe, a yogi with a “witchie” spirituality. She talks about the “universe” and believes in sage burning and tarot cards. 

    Not a classic beauty, but she exuded sexuality. God I loved kissing her. And those thighs…. Whew! 

    Like all of us at this point in our lives, she came in with a ton of baggage. Several failed marriages and relationships. Many of which left scars that impacts how she handles situations, whether she acknowledges it or not. 

    After the 3rd or 4th date she told me she loved me. I already knew I did as well. Not long after she proclaimed that I was her best friend. As someone who has precious few (1) real friend, I swooned. 

    Given my history, I was grateful she resisted my attempts to have her move in with me after just 5mos. 

    While living apart, we talked every day. Sometimes multiple times each day. I recognized that often these conversations were 80% about her and her day and 20% about me. I was OK with this as I found her fascinating. A latter recognized something else. 

    I discovered that her past relationship trauma resulted in a singular focus on herself. She needs to make sure she was good, before anything or anyone else. OK, I got it. Fine. I can deal with that. 

    Then – in March 2025 I lost my job… again. She was very supportive, but at 59, I struggled to get an interview much less a new job. The food truck turned into a FT job, but it is still not enough to sustain me and my expenses. 

    Meanwhile our relationship continued to grow and evolve. This past summer she got a new job near me and moved in to my place. She knew I didn’t have a job, but I insisted that all would be fine. Soon, I’d get a job and we’ll be Ok. I’d always landed on my feet. I honestly believed what I was telling her and myself. Evidently I was wrong. 

    Within 30 days, my vehicle got repossessed and she moved out. I know she had previous financial trauma due to one or more of her exes and, while she denied it, I believe this played a factor. Stating a lack of trust in me and not feeling “safe & secure” in our home, and that I was not in a position to “support her”, she moved out and got her own place. 

    Naturally I fell apart. In the span of six months I lost my job, my vehicle and my girlfriend. She maintained that there remained the possibility that we can stay together given enough time and space. I held onto that possibility like a life raft. 

    This morning, Nov 1 2025, she texted me and told me she was done. More specifically, “I’m better without you in my life”. 

    A text – after more than a year together. I still have no FT job, no vehicle. And now no girlfriend. Where do I go from here? 

    I am so lost…