What to Expect When You’re Expecting to Retire

A friend and former colleague of mine recently emailed me to tell me that he was about to retire. He has spent the last few years in an intense and stressful job and he said that it had taken a physical and mental toll. His financial advisor had signed off on the plan and in a few weeks he will take the plunge.

Like me, my friend has worked for nonprofit organizations for most of his career. Those of us who choose this kind of work, are often driven by the mission of the organization, by the purpose of the work as much as we are by the need to pay bills. For those of us who are lucky enough to find work that we deeply believe in, work is more than a paycheck. It is an expression of our identity and sense of purpose.

This very fact means it can be very hard to call it quits and after one does, it can be a significant, even painful adjustment.

Like retiring from any job, there is the psychological impact of not earning. After a lifetime of saving for just this day, it is very difficult to turn off the tap and allow the water to start running out of the bowl. Your calculations (or your advisor’s) that tell you that it will be fine, that you have a great chance for success, don’t help much. And no, the number on the paper doesn’t matter. The discomfort has little to do with how much you have and everything to do with the mental transition going from saving to spending.

Second, for those of us for whom work is a part of our identity, there is a feeling of being adrift. Who am I if I am not [insert your job title here]? What is my purpose if I am not working, earning, providing, and serving the mission?

Finally, for those who have often spent more time at work than with their own families, work provides a large part of one’s social life, human interaction, mental stimulation, and yes, relationships. When you leave your job, things can get very quiet awfully quickly.

My friend and I are getting together for lunch a few weeks. He probably won’t ask me for my advice on retiring but if he does, here is what I will say.

If you can, you should.

Not everyone can retire. You have to be able to make ends meet. How much you need depends on lots of factors including your age, your financial obligations, and how you’d like to live. If you have a financial advisor, ask them to help you run an analysis. If you are a do-it-yourselfer there are lots of online resources to figure it out (ask me, I’ll point you in the right direction). But if you determine that you can retire, you should. There are simply too many other interesting things to do and too little time to do them. I have had friends who told me that they haven’t retired because they can’t imagine what they would do with themselves all day. To which I say, “Imagine better!” Others have told me that they had friends who retired and dropped dead shortly thereafter. But, it turns out that those who don’t retire also die. Whether you remain at work or not your time is not infinite. Of our 4,000 weeks (average human lifespan) if you are 60, you have maybe 2,000 left.

Time is of the essence.

Don’t wait to do the things you want to do. Once you retire you should have a plan of how you want to spend your time. It could be travel, volunteer work, outdoor adventures, or classes. Whatever it is, don’t wait. You might have 20 years of good health ahead of you, but you might not. If there is something you dream of doing, do it. Three days before my wife retired, we set out on a 3 month road trip to Alaska. The next spring we did a big trip to the National Parks of the southwestern U.S. including a hike to the bottom of the Grand Canyon. In the course of the following year, we both had some health complications that made traveling more difficult. Those issues only kept us home for a few months but they were a wakeup call. Don’t wait for anything. You just don’t know how much time you have. As far was we know, we get just one shot for our singular consciousness, unique in the history of the universe, to experience everything it can.

You have to work hard at maintaining the friendships that are important to you.

When you stop working, most of the people who were a part of your life day in and day out just vanish. They are still up to their eyeballs juggling work and family. Getting together with you may not be their top priority. Even if it is, you might find that without the current crisis at work in common, you may no longer have that much to say to one another.

Having said that, social relationships are even more important in retirement. Figure which friendships are most important to you and take the initiative to keep in touch. The onus is on you to call, email, and suggest getting together. If your friends are still working, make it easy for them by meeting them for lunch near their office or home. And if they don’t seem interested or motivated, that’s ok. As painful as it may be sometimes you may be more interested in maintaining the friendship than they. Move on. Sometimes it is easier to focus on other friends who are retired. They may be craving social interaction too. Hardest of all is making new friends but I can tell you it is possible.

Stopping paid work doesn’t have to mean loss of purpose and meaning.

When I first stopped working in 2020 I had the chance to meet up with a childhood friend who now lives in Denver. We went fishing together. (Well, he went fishing. I watched). I told him that although I had retired, I still felt that I wanted to make a contribution. My friend who had spent his career teaching history and economics told me, that if I was in a position to retire, the all-knowing marketplace was letting me know that I had already made a sufficient contribution. Notwithstanding, I still felt like I had more to offer. Shortly after that, I launched my blog and began writing a post every week. In addition, I have added some volunteer work and then there is the non-stop occupation of helping family and friends with their Apple products. Most people, I think, find it rewarding to be useful to others, to society. Find something that you are good doing or making and give it away.

If you can afford to never again work for money it doesn’t mean that you shouldn’t but be selective about it.

When I was planning to leave Hillel at the University of Rochester, I had thought that I might take another interim gig somewhere. But then Covid happened and there were no gigs. June 30, 2020 was a cold, hard stop. The phone stopped ringing, The emails stopped. There were no more zoom meetings or deadlines to meet. It was a shock but I am glad it happened the way it did. I was forced to confront what it meant not to work in terms immediate and real. It was the first time, I had been without a job since 1986. The longest vacation I had ever taken was two weeks. Other than some one-off teaching gigs, I didn’t do any paid work until March of 2022 when my friend David asked me to join his organization in a part-time finance role. By that time, I had made piece with the fact that would probably never work for pay again and I had realized that I was ok both financially and in terms of having things to do. So when David approached me, I was able to consider the offer in light of whether it was something that I really wanted to do. I didn’t feel like I needed to do it if I didn’t want to. I decided that I would enjoy working with him and I took the job. Two years later, when David left the organization, I quit too. I  just didn’t think it would be fun without him and I knew my life could be completely full without paid work.

Now my only criteria for considering work is: will I enjoy it? Will I have the opportunity to learn something new? Will I like the people I will be working with? The answer to all of these must be yes. If not, thank you for thinking of me, I’ll pass. Every job, even volunteer work, can have some amount of aggravation and stress. But if the aggravation exceeds the pleasure, I’ll find something else to do.

Being retired requires more discipline than working.

Without deadlines, bosses to be accountable to, and the pressure of proving that you are worth your paycheck, it is easy to get lazy. To procrastinate. If you want to do more than just run out the clock on your remaining years, you need a plan and you need to execute it. It’s ok if that plan is to “become as good at golf as I possibly can” as long as you have examined yourself and determined that is what you truly how you want to use your remaining time.

I have work to do in this area. I don’t always use my time as fully as I might but here is what find myself working on/doing:

Volunteer work

I serve on a volunteer committee for a fantastic nonprofit, The Good People Fund, and do some one on one consulting for their grantees. I have also taught my class Financial Basics for Nonprofit Managers a few times in the past year.

Exercise

I walk 90 min to 2 hours per day and try to get to the gym twice a week. The gym doesn’t always happen, but the walks pretty much always do. During my walks I listen to podcasts about history, philosophy, or ideas.

Blogging

My recent sabbatical notwithstanding, I try to write a blog post every week. Sometimes, I am not sure if anyone is reading them, but I decided that I write them for me and if no one reads them, I am ok with that.

Household Choirs

I spend a not insignificant amount of time grocery shopping, cooking, and managing our finances. It’s all stuff that had to get done before I retired but somehow it seems to take more time now. Barbara and I often scratch our heads and wonder how we got anything done when we were working not to mention when we were raising children!

Travel

Since 2020 my wife and I have driven to Alaska and back, visited the parks of the southwestern U.S. Had a bike trip to Wisconsin. Spent a week in Maine. A few weeks in Florida during the winter. Drove to North and South Dakota and back. Most recently we spent a month traveling to Big Bend National Park in Texas and back. We’ve put more than 100,000 kilometers on our camper van. This fall we are planning our first international trip since covid. (Stay tuned for details.). We pretty much always have a plan for some trip coming with within the next few month. Not everyone enjoys traveling but if you do retirement gives you the time to do it. And you don’t have to be wealthy to do it. We travel cheap and slow. We mostly camp which is usually $15-40 per night and we mostly prepare our own food, which means we spend the same or less on groceries as we would at home.

and, yes, some work

Until April, I was doing some paid work. Right now I am not, though there are some possibilities on the horizon. If the right thing comes along that would give me the chance to do something fun, learn and work with good people, I will do it though the most I would consider would be a quarter to one-third time.

Retirement is not exactly what I expected. I had a fantasy of days of endless travel, stacks of books, long backpacking trips, and music lessons – somehow all at the same time. The reality of it is that it is more or less life is as was before but less work and more time for the fun stuff. There are some things I miss about working. I miss the camaraderie of the workplace, the sense of shared purpose. But I am also aware of how much more there to do besides work and I am grateful that I have some time to do it.

The world’s a narrow bridge; fear nothing.

Bully Besting

“He’s not supposed to fight back, he’s supposed to have thick skin.
He’s supposed to lay down and die when his door is kicked in.”

— Bob Dylan, "Neighborhood Bully" from the album Infidels

I got bullied a fair bit when I was a kid. Nothing horrible. A bunch of name calling. Some banal Jew hatred. The occasional shove. Every once in a while, some kid would get more physical.

In junior high school a small kid, probably six inches shorter than I picked me out to get hostile with for reasons I never understood. He started confronting me in the hallways. I wasn’t afraid of him. He was a tiny thing, but I didn’t want to fight. Well, maybe it wasn’t that I didn’t want to fight, I had no idea how to fight, having been raised a pacifist. I tried to flee but a school is a small place. There was nowhere to go. One day he decided to pursue me. I ran into the principal’s office, and he followed me in.

The principal talked with each of us separately. When I expressed complete bewilderment as to why this kid had it in for me, the principal told me that the kid had said I had called him “no neck.” When I continued to be confused, the principal explained that the kid had a deformity and had a very short neck. I hadn’t noticed this much less made a comment about it. The kid wasn’t on my radar. I couldn’t have told you his name. We had no classes together. We had never spoke a word to one another as I recall. If I had spoken to him, I certainly wouldn’t have insulted his disability and as I said, I wasn’t aware he had one.

The principal suspended us both. The other kid got three days off from school; I got one. The principal told my mom that he knew I had done nothing wrong, but he would be perceived as unfair if I got no punishment. I thought it would have more fair if I also had gotten three days off from school!

This kind of thing wasn’t too common. I am not claiming victimhood or blaming my current neuroses on the fact that I was bullied. But it did happen. Why? Who knows? There was something about me that attracted unwanted attention. I liked to read. I was uninterested in sports. I generally preferred hanging out with teachers to other kids. Maybe it was the fact that I didn’t seem to care that I was different that signaled to others that I thought I was somehow special.

If I am honest, I kinda did think that.

Fast forward a few years. I was 16 years-old and in high school. Another kid whose name I don’t remember (I think his last name began with a T) decided he didn’t like me and made me well aware of the fact on the bus, at school, and around the neighborhood. One hot summer afternoon I was walking to Jeppe’s Comic World in Catonsville to pick up the Marvel literary universe monthly haul when I saw T slouching toward me on the sidewalk of Edmondson Avenue.

I don’t have a great recollection of what happened next. It was nearly 50 years ago but I am pretty sure I didn’t start it. He blocked me or maybe shoved me and I, to my own surprise, did something I rarely or never did.

Perhaps it was nascent levels of testosterone racing through my bloodstream. Perhaps the heat of the day had made me irritable. Maybe I was channeling my favorite Marvel superhero the Hulk. Maybe, I’d just had enough. I shoved him back as hard as I could (which was likely not very hard by any objective measure). We ended up in a bit of a tussle right there on the sidewalk. I had taken wrestling for a few years at the J and I tried to get him in the forbidden full nelson head lock. I failed miserably. I was a lousy wrestler. Plus, he had the advantage of me in size, strength, and without a doubt fighting experience.

Then it was over. He got up. I got up. He looked at me for a moment and laughed. Then turned around and continued his way as if nothing had happened.

I was physically unhurt. No black eye. No blood. Not even a bruise that I recall. I dusted myself off and continued to the comic bookstore and picked up the stack of comic books, The Avengers, The Fantastic Four, and X-Men and walked home.

I don’t think I ever told anyone what had happened. It was too humiliating. Not just being bullied, though certainly that. But also, the fact that I had been drawn into his filthy squalor, his moral vacuity. I felt sullied by being forced to brawl with this excuse for a person. T was not someone I hated, didn’t even dislike really. He barely registered as an entity on my mental map of the universe. I had understood that I had no choice but to fight back but I didn’t feel great about it nor did I feel I had acquitted myself well enough to serve as a deterrent to any future harassment.

But here’s the funny thing. T never bothered me again. I don’t remember him ever saying a single word to me or even making eye contact with me again. Nor was I ever in another fist fight. In fact, I have no recollection of being bullied again after that day, at least not physically.

It has become a cliché to point out that bullies are cowards, but it is, of course, true. Bullies generally aren’t looking for a fight. They just want to appear tough. They want to push around those who won’t resist. They want others to fear them. They want to strut about and make themselves look big and important without putting in the work of gaining respect through courage, discipline, and virtuous behavior (understandable since being virtuous is a poor predictor of being respected).

Most of the time just appearing to be ready to stand up to them is enough to discourage aggression. But occasionally, you will meet a bully who finds your very existence to be an affront. One who thinks that the fact that you are different means you think you are better than they. Who is willing to consume resources that they need for their own subsistence if it will make you suffer. Whose story of identity is grounded in destroying you at all costs. Who sees your existence as the explanation for all their failures. And who is itching to fight with little or no provocation.

Bullies of this sort understand only the use of force and sometimes even need to be roughed up a tad until they are forced to consider that maybe, just maybe God is not on their side.

So, when a kid like that comes toward you as if they own the sidewalk, be ready to throw a punch if but only if you must. And if you do have to take a swing, hit him as hard as you can. Even if it sullies you to do it. Even if it is at odds with your story of the essential good in everyone. Even if you know the bully and his buddies will claim that you started it and that lots of folks, even well-meaning ones, will believe him.

When it’s over get up and go on your way. Maybe you won’t need to do it again. Perhaps the one bout will be enough to teach him the lesson: that you have as much right to walk around the neighborhood as he does, that you will stand up for yourself, that you won’t be intimidated, that fleeing is not an option. Especially if there is nowhere to go.

The world’s a narrow bridge; fear nothing.

Four Skills

In the course of a life, one is constantly presented with the opportunity to learn things. Sometimes one is required to learn them for school or for work and sometimes we are drawn to them because of interest or passion. We often ignore the optional opportunities because of time constraints or laziness. But sometimes we take up a learning opportunity and pursue it until we reach a level of competence. For those with talent (or more likely extreme perseverance), a level of mastery may be achieved. Though far from mastery level, these are four useful skills I have acquired and which I continue to try and improve after decades of application. I offer these not as a boast nor to suggest that you pursue these but rather for you to consider what skills you are practicing and be alert to what you might want to take up next. 

I am not including in this list the skills that are essential and that virtually everyone learns. These are so universal as to be taken for granted. (obviously, I understand that they cannot nor should not be taken for granted.) These include, reading, writing, basic math, driving, dressing oneself, etc. I am speaking of optional skills that while anyone might learn them not everyone does. Everyone, I suspect has a list that is unique to them. Here are mine.

Accounting/Double Entry Bookkeeping

Easily the most useful skill I learned for my work life and for understanding and managing my personal finances. As an English major, I assiduously avoided classes that involved business or math. But when I found myself in my first nonprofit job there was a vacuum in the finance function of the organization. I made a deal with the executive director that if she would buy me a Macintosh to work on, I’d get the organization’s books squared away. To be clear, my motivation was getting a Mac to use at work (I already had one at home) not to learn double-entry accounting.

I didn’t know the first thing about accounting. With the help of a college textbook, the organization’s external auditor who was generous with his time, and a lot of trial and error, I taught myself accounting. It opened incredible pathways and opportunities in the course of my career. I used the same professional level accounting software that I used at work to manage my personal finances as well and thus gained a level of understanding that allowed me to make better decisions about investing and our household finances. To this day, I track all our household income and spending to the penny as if it were a small business, which it pretty much is. This level of control is not for everyone, but I can’t imagine not doing it after all these years.

More importantly, I have come to appreciate double-entry accounting as one of the most beautiful and perfect systems devised by human beings. It is also the closest thing we have to a near universal system adopted around the world (but for the U.S. the Metric System could be that). Virtually, every business in the world that has an accounting system double-entry bookkeeping.

Bread Baking

Ever since that first loaf, I baked to write about for Freshman English in 1980, I have been an avid baker. I conservatively estimate that I have made more than 2,500 loaves of challah, hundreds of bagels, and countless loaves of wheat, rye, and kamut, breads. Last week, I obtained a portion of sourdough starter from my dad, I have begun a sourdough journey with four loaves having already come to fruition. Two of them were good and two had disappointing oven spring. They were still quite edible notwithstanding.  Aside from the few who eschew gluten for health or theological reasons, people love bread. Friends and family are always delighted to receive a loaf of bread. It is an easy way to make people happy and the process of turning flour, water, and salt into bread is rather magical. In most cases any bread you bake at home will be better than anything you can buy at a grocery store. Far less expensive as well. It is a rare week that I don’t bake at least one loaf.

Knife Sharpening

I love to cook and nothing makes cooking more enjoyable than a good sharp knife. It is hands down the most important tool in the kitchen.  If your knife is sharp, you work faster and more effortlessly. You will cry less over your onions. A sharp knife is safer to use since it is less likely to slip.

The best way to sharpen knives is with a set of whetstones but finding the process somewhat intimidating, I avoided them for years. I tried every other sort of sharpening system including manual handheld sharpeners, electric sharpeners and a system where the blade was held in a fixed position and the sharpening stone was pushed against the blade. None of these systems proved satisfactory. I wanted a blade so sharp I could shave my arm hair with it.

Around 10 years ago, I broke down and bought my first set of Japanese whetstones. I watched countless YouTube videos on sharpening, and I made many a knife worse before I started making them better. But after a few hours over many months, I got the hang of it. Now I sharpen my knives every six months or so and in between I hone them on a ceramic hone that brings them back to razor sharpness with a few strokes. My favorite knife is a fussy santoku with a carbon steel blade that will rust if not washed and dried immediately after use. But it is fast to sharpen, holds and edge, and is perfect for my hand. Let me tell you it glides through food. Keep your fingers away from the blade! Why, it’s sharp enough to shave the hair from your arm! But don’t. Safety first!

American Sign Language 

We found out our daughter was deaf when she was 10 months old. A week later, we left on a family vacation, a road trip to Montreal, with a brand-new copy of The Joy of Signing open in the front seat. That week my wife, my daughter and I learned our first signs and a few weeks later my daughter made her first sign. It was a request: “Milk.”

If the only thing learning sign language allowed me to do was to communicate with my kids, dayenu. It would have been enough. But it did so much more. Learning ASL opened me to a world that a scarcely knew existed. The Deaf world is a vibrant and robust subculture.  It also led me to an involvement in Jewish life that I had previously been a stranger to. (That is a story for another day.)

Some of my most fulfilling experiences were the twelve Birthright Israel trips where I staffed the ASL trip. The Deaf students and Israelis that I had the opportunity to get to know over those 10-12 day trips changed the way I see the world. I was on one such trip when Apple announced that its new system software would allow iPhone users to make video calls “FaceTime” allowing Deaf people to have synchronous conversations over the phone as hearing people had had for more than 100 years. I don’t know that I have ever seen anyone so excited about a new technology as those students were.  

My ASL skills have stalled in recent years. With my kids far away and no opportunity to sign every day, my level of competency, always more conversant than fluent, has stagnated somewhat. Still, I can mostly keep up my end if my conversation partner is patient and slows down for me. It is the closest I come to a second language.

Check out the new Deaf President Now! movie on Apple TV+ to see how Deaf people took control of their destiny at Gallaudet University the year before my daughter was born.

Each of these skills took between 10 and 20 years to attain a level of competency. In none of them am I even close to among the best. In fact, the most I would claim to be at any of these is adequate. Still I am always on the lookout for the next learning opportunity that might present itself. I might just have enough time to get pretty good at one more thing.

The world’s a narrow bridge; fear nothing.