The Abridged Diary of a Workaholic

September 16,1967. Ten days ago, I started my sophomore year of high school. Not yet 15 years old, dad decides it is time for me to start working at The Depot, a restaurant where he is employed. As the name implies this upscale steakhouse is a converted NY Central Railroad depot on the Erie Canal. Until today, my vocational pursuits include mowing lawns and running a pop-up soda stand on the 14th tee of a local country club. A budding entrepreneur, I cajoled each of my family members to purchase a discount case of soda (one case per customer) for five cents per can. I, in turn, sell them to golfers on hot summer days for fifteen. It is my first lesson about supply and demand. Knowing I am embarking on my first real job as a busboy makes me excited and anxious. It is work with regular hours, a boss, and a paycheck with a stub documenting my social security withholding. Getting and holding a job is one more “rite of passage”, another step closer to being a grown-up. Nepotism gets me the job, but holding the post is another matter. Each weekend, I must prove I deserve another week.

April 28, 1975 – Today, I start my first career job. Since my busboy days, I have always had one way or another to put food on the table and a roof over our heads for my wife, and later a first son, and then three years later a second one. Now exiting graduate school, I have my first “real” job. It pays less than my stint as a cashier working the night shift at the grocery store chain, but I suspect it will take me further. I don’t know where it will lead, but I am a computer salesman, or more accurately a computer sales trainee.

August 1975 – I am a terrible computer salesperson, but an outstanding computer program analyst and designer (or so it would seem). In any event, that is what I am told. This is a great job for an introvert with good communication skills.

August 15, 1977 – Longer on hubris than real skill, I have hung out my shingle. I am taking the deep dive into the entrepreneurial pool. So much has happened this year, a new house, a new daughter, a new venture - a business delivering custom computer software – what could go wrong?

October 1, 1979 – Today, I started my first ever “traditional” data processing programmer job at a bank. It is a nice 37.5-hour job with great benefits and a decent salary. I caught public transit to downtown this morning. I am getting to know my kids. The last two years of 90-hour weeks has provided many useful lessons that I can only hope will serve me for a lifetime. The most important one – being successful is hard work.

February 11, 1980 – What a breath of fresh air! I have never felt so trapped as sitting in a cubicle from nine to five, testing and retesting programming code of no real interest to anyone except the bureaucrats running the bank. This new job is a godsend. I will be managing a team of programmers to do much of what I did when I owned my business. The big raise will be handy. I can split my time between working with clients, analysts, and programmers. I am going to love this job.

January 1, 1985 – The last twelve-month stint as project director for the steel mill automation project has paid off both because the project was so successful, on-time, under-budget, and now I have my own practice to run. I have enjoyed my five years with this company and the opportunities offered. I am the youngest practice manager among my 30 peers.

October 19, 1992 – The last twelve years have had more good times than bad, and a diversity of experience unparalleled elsewhere. My second son has started university and it is time for me to cash in. I would have been happy to continue my career with all my friends and colleagues, but the 70% raise and the opportunity for a new adventure in a new city is too appealing. My best friend recruited me, and he assures me that I will be working fewer hours, more time for family.

September 11, 1995 – I was so excited to move here three years ago. I was thrilled to embark on my “executive” career. I had hoped to reconnect with loved ones, too often ignored during the first decades after graduate school. Two layoffs in two years have provided me plenty of free time, much of it consumed with job hunting. Today, I have decided to hang out the shingle again. This time I am much longer on experience and much humbler. Getting fired twice will do that to a person. My programming days are behind me, too long ago, too many technological advances. What I can do is work with executives to advise how technology can be deployed to deliver process excellence. Now if someone will pay me to do that.

December 4, 1995 - Sprint interviewed me last week and has asked me to come to Kansas City and work with their team to implement technology to better understand their metadata. This is not the gig I imagined, but it will pay the bills and it should an interesting use of my experiences.

May 4, 1998 – I am still consulting for Sprint having just completed a project to deploy the first corporate-wide intranet. The enabling technology is the brainchild of a group of Bay Area engineers. I start as the president of the company today. The technology is cutting edge and I understand the myriad of applications for its use. The company is small. The energy and promise of the young entrepreneurs are contagious. At 45, I am the old man in the room.

September 21, 2001 – I am back home, literally. I took the summer off in Half Moon Bay recuperating from three years of 70-plus hour weeks which resulted in taking the start-up public and my promotion to CEO. My reward is not a huge stock option payoff, but rather a dot-com bubble burst which took down the deserving with the undeserving (pets.com). I had brought in the chairman of the company I had worked for in the 80’s as a board member to help us weather the rough seas. I was counting on his forty years of information technology expertise to provide necessary counsel. The financial markets are unkind. We were beyond help. He offered me the opportunity to move back to his company as the Vice President of North American operations. I have 23 direct reports and an organization of 1200 professionals in fifty cities as far flung as Anchorage and Jacksonville. It is good to be back working in Western NY.

July 1, 2004 – Well it is true, you cannot go home. The company that I returned to was very different from the one I left a decade earlier. My wife grew tired of my endless travel routine which included too many flyover commutes from Half Moon Bay to Buffalo. While I was absorbed with endless work details, I woke up one morning with all my kids out of college, married, and four grandchildren. “Let’s do something different. Let’s work together again.”, she pleaded. So here I am. We are about to embark on a new adventure, ranch managers for a bison ranch in Bondurant, Wyoming for a self-made billionaire. It is a small ranch by Western standards and a huge farm for a kid who grew up in the dairy belt of New York State.

November 11, 2021 – What a ride! I would commend to everyone finding a billionaire to work for each day. Gird yourself with patience and prepare yourself for too many projects, too eclectic for a sane person to connect the dots. For seventeen years, I have been living vicariously, feasting on my boss’s visions. Today, I am president of a bison business, restaurant operations (full circle from my busboy days), and co-CEO of a digital news business. The moment I believed that I cannot be surprised, he astounds. He made an extraordinary offer this morning. He is willing to gift me the one-year-old news media company. This is not as altruistic as it sounds. The business has yet to realize any revenue but is on the cusp. There is so much left to do. My entrepreneurial juices are flowing again. I am giddy. Well, more accurately, I am feverishly excited commensurate with my 69 years. Of course, I am flattered.

Still November 11, 2021 - I have turned to people I trust for advice. This is an email thread with a close friend who was faced with a similar challenge four years ago. I am entrusting this to the journal for posterity.

Me: Boss came to my office this morning and offered to gift me the news company. He could have just as easily offered me his jet. I cannot afford to keep up either. The business has assets of about a million dollars. That is an interesting fact, but not relevant to decision-making. The monthly expenses are currently running at $500K with no revenue. He is offering to loan me the money to ride out some period (a year?). I can do much as you did: Cut expenses to the bone and run it as lean as possible. When we made a similar overture to you, you were at your prime, much as you are now. I can pretend that I am, but you and I know the truth. One bout of illness and rather than ride my bike an hour a day, I will be lucky to walk from here to there. If I do this wrong, I could be a pauper. That is not so much a worry. My real dilemma is I would have let down all the people who love me and the employees who count on me. I think if I say “no”, then I will have to retire. Then what do I do? I find entrepreneurship terrifying (because I have done it and know how much work). I find retirement equally terrifying. I am reminded that I was ready to take a flyer on your venture a few years back, but much less risky and sadly, I was a bit younger.

K: Wow, that is a big decision to make. I guess to decide, you need to take a hard look at what 'success' of this gift would look like:

1. Do you feel passionate about the company and making it a success?

2. When you envision the potential, is it exciting or does it feel like a burden to endure so you 'don't let others down'?

3. Can you honestly trim 'the fat' and make it generate a significant revenue stream within the next few months? How? I frankly don't understand how someone could be pouring 6 million dollars a year into a company and have no revenue to show for it. What does 'loaning' you the money mean? Is it really something you will have to pay back if you find you have spent a few more million with nothing to show in a year?

4. If this opportunity truly is the 'next big thing' that has massive money-making potential, would there be an opportunity to take a more passive role in the day-to-day grind by this time next year?

5. Why is retirement terrifying?

To be perfectly honest, I would 1000% retire right now (and I am not even 49 yet) if I knew I could comfortably do so. I don't understand why people feel the need to be 'productive' until the day they die. I don't think it means you are lazy if you retire, however if doing 'work' is your only motivator each day, then you have your answer - take the company and throw yourself into making it great. If you do that, however, I would have some non-negotiable time limits on meeting specific goals.

Lastly, and this may sound insensitive, but if you do decide to take this on, it should only be because you are passionate AND optimistic about the potential of the company. This decision should not have anything to do with the people you would be paying to keep it afloat.

(Lots more back and forth dialogue)

November 12, 2021 – K: I like hearing where you work this all out in your mind but the one thing I haven't heard you say is that you are excited by the opportunity. You are grateful and flattered (it's a big deal!) but it doesn't seem like you feel passion or excitement for it. Would you agree?

Me (On Retirement) - “Terrified” might be a bit of hyperbole combined with a writer’s device of literary repetition – terrified of this and terrified of the opposite. However, I am writing this to face my fears. Retirement can be a new beginning, but it certainly marks an end. It is a journey into the unknown and reinforces the truth of our mortality. In business, we retire assets when they have outlived their useful life. And so, it is with people. I am nowhere near the end of my ability to contribute. The calendar would suggest otherwise. Retirement forces us to redefine value. I mentioned that I have been working since 1967. For all the years since, and likely many of the years before, watching my mom and dad, value was measured in converting ergs into cash. That is what it means to be working class. People talk about sweat equity as if there is an alternative for the working class. If I am not working, who am I. If I am not providing for the ones I love, what is my purpose? If I cannot spoil the people most important in my life, what is the point? You know how I am this way. I pass no judgment on myself either way, I leave that to others. The rational mind (even my rational mind) knows that most people in my life might rather have me and my time than anything material. But this is its own dilemma. I do not want to turn my time over to children, grandchildren, great grandchildren, wife, mother, mother-in-law. Today, I am a wallet, carefully managed. Retired, I am an hourglass, with sand needing to be consumed. What better thing do I have to do but what others imagine? Retired, I am a vessel of minutes to be disbursed for activities of no particular interest to me. My avocational interests are deemed frivolous by those who resent my inattention. How much can a person write and about what? How much can a person read history or economics, and to what end? Running an estate is hard work and there is always something better I should be doing, but, of course, there is not something that I need to be doing. I have people who do that for me. No one thinks I am going to chainsaw a tree or landscape a bed. In fact, no one would trust me to do either or be satisfied with the result.

I have not figured out what retirement looks like with me smiling. Today, it feels like an epilogue with the last line – And then he died. I thought years ago I might become more involved in community activities, and that might work out except that I am not fond of people, especially people who like to organize and manage community activities.

November 15, 2021 – Me: Of all the counsel, I received, you are the only one who asked the right questions. Confirms my instinct of reaching out to you first. What seems natural (self-evident) to you does not to others. You were the first I sought out for advice, and you are the first to know the outcome. You deserve both. I have decided to pass on his offer. Harder for me than you might think. I am a process guy. I love the challenge of it all. But your words got stuck in my brain like an ear worm – “passion and excitement”. Ironic, I was forced to reflect this weekend, alone in my corporate apartment, what gives me passion and excitement. When was the last time I had that in my life? Do I now? With it, I can write day and night. With it, I do not sleep but am never tired. I understand passion and excitement. It provides singleness of purpose. It creates a clear picture of priorities. I did not have to imagine how it might feel. So, the irony is you being the only one to remind me it must permeate one’s soul, first and foremost.

January 1, 2022 - I have resolved to retire in 2022. New Year’s resolutions are not a habit, but like so many people, any day of the year I might commit to better behavior. These include eating and drinking less, sleeping more, losing weight, exercising more. In that moment, I am very disciplined, but the next annual physical reveals how fleeting my determination. I wonder about my commitment to retirement. Any to whom I have nonchalantly mentioned the plan, have laughed. None of my kids, siblings, friends believe it. First and foremost, is the daily bread. Earning and saving for retirement is more satisfying to a Scotsman than withdrawing dollars. Second, more important, is the finality of retirement. Habits developed over half a century are hard to modify. The decision to end employment is at some level, existential. Who am I, if not that person who directs, decides, advises? Third, and closely tied to the second, what do I do next?

For day in and day out, I find that an afternoon propped in the bed with a good history book, inevitably leads to a nap. Presently, this is a rare, sumptuous experience that I would love to have become a habit. In my library, I have 1000 books, unread. Apparently, I enjoy the collecting more than the consuming. Imagine how many naps would be instigated by 1000 books.

I usually wake early. Today, knowing that whatever chore I might start will be interrupted by my morning staff meetings, I too often squander those minutes. An empty calendar would be a blessing. I could jump out of bed, rested, having turned in before ten. There would be no worries to keep me awake or trouble me through the night. I might tackle either a workout followed by writing or writing followed by a workout. I look forward to finding out which routine works better. What to write? I am blessed that I find most topics interesting and rarely suffer a lack of words. Yet, over the course of my life, I find myself circling back to two themes, the foundations of economic thought, and the intersection of economics and technology. If I thought I could provide original exposition, I might like to try my hand at several serious essays, in addition to the poetry, short stories, and Vocal challenges.

I like to bicycle. The house we purchased a few years ago at my wife’s bidding is wonderful. Ironically, we refer to it as our retirement cottage, so very little retiring involved. I master downsizing equally well with retiring, so no one would mistake Baron’s Walk, our country estate, for a diminutive bungalow. This part of the world is not known for shoulders on the roads or patient drivers. It is always better to find a recreational path. The closest bicycle paths are a 30-minute drive. Employed people do not have several hours per day to execute such a feat. It would be delightful to have the time.

In 2005, I was fortunate to spend 13 weeks in County Cork, Ireland at a culinary school. I enjoy the creativity of cooking and would enjoy practicing and improving my skills. I can envision doing more inventive cooking and blogging my latest creations. I feel the same way about playing blues on my Gibson, but fair to say that there are not enough years left for me to get truly good. My guitar playing is like my typing, but there is no backspace or delete key on the acoustic.

An improbable interest reserved by a few as vocation and the vast majority as tedium is tax preparation. I went back to graduate school part-time a few years back and earned a master's degree in taxation. I like the puzzle of being presented with a taxpayer’s situation and figuring out how to leave, legally, more cash in her pocket. I could imagine spending the colder, non-bicycling months, doing tax preparation a few hours each week.

I have been approached more than once to serve on boards of startup companies. I have always deferred for lack of time and avoidance of any conflict of interest. In retirement, I could replace those time-wasting drives to the airport with drives to the city. It would be rewarding to help the next generation of entrepreneurs attain their dreams. It would be even more gratifying, if I could teach them to embrace and enjoy the journey.

I love dogs. Having convinced myself that I am part canine, having a pack with whom to frolic is a pleasure missed. My life has not been conducive to adopting a hound of any sort. I have taken dozens of online quizzes with titles like “What dog is best for me?”. Retirement would give the time a dog deserves. We could learn the agility course together as she weaves and jumps, responding to my every command. We could be as one.

I am a man in his statesman years of middling height, waning upper body strength, and zero mechanical aptitude. However, I am married to a sexist. She believes there are certain chores that can only be done by the male of the species. Her loving arms terminate with hands that hold the Scroll. The Scroll is a register to which items are added at twice the speed of those deleted. To refer to the Scroll as a “honey-do” list would be an insult to both its scale and its author. The Scroll is an unnecessary edifice. My wife can recite all its contents and does so on any Saturday or Sunday. Before managing our estate, she was a professional estate manager. She took care of the residence with guest homes on a 1300-acre ranch. She ran multi-million-dollar construction projects at the ranch and her principal’s second (or third or fourth) home in Manhattan. My spouse combines the exacting skills of a Jockey underwear quality assurance inspector with the imagination of someone with much greater means than I. Should any of my moments be spent in quiet reflection, the silence is deafening for her, a vacuum to be filled with some chore. In retirement, would my weekdays become an extension of my weekends?

As I reread this piece, retirement sounds exhausting. Maybe, I will hold off until 2023.