My First Letter of Instruction

Like the thousands of other attorneys starting in New York in 2004, my first year associate experience followed a prior summer filled with lunches, wine and cheeses, sporting events and bar reviews. Not just in New York, but I was also flown to London for six weeks to experience the virtues of the UK summer associate scene. 

What an amazing summer! When talked about today those summer associate months are either cherished with a tinge of longing or frowned upon as terribly excessive, sometimes both. They are always viewed as something of a less mature Wall Street past. Whether or not Wall Street is the better, worse, or a different flavor, whether Millennials are harbingers of the end of an era of Protestant work ethic, and whether the Great Resignation is overdue or an act of the greatly spoiled, are all topics I will try to avoid here. 

Far more critical to my own professional development were the first few months of my time as a new associate at a major New York law firm. It was a time of real professional growth. Twenty years later I reflect on the small, conceivably stupid things that I was asked to do that caused me terrible stress and anxiety, but ultimately proved incredibly invaluable to me in my career. My reflections may come across as humorous or sarcastic, but you can rest assured it was not funny at all to me at the time. These were the first days of my career and as a magna cum laude graduate of a pretty good law school at a top 10 law firm on Wall Street. Serious stuff. 

I started my career drafting Letters of Transmittal (LOTs) for debt tender offers. I don’t know how many people can say that, but it is certainly not the type of work that will make anyone’s eulogy. Drafting LOTs is not purposeful, relevant, useful or honorable in any way imaginable. No balanced professional review would conclude to the contrary. 

The majority of people reading this note have no clue what a letter of transmittal for a debt tender offer is. Many talented professionals, some of them my contemporaries, probably don’t know either. By definition a LOT is a cover letter. In the world of debt tender offers, a LOT is a letter of instruction that tells bondholders how to tender their bonds into an offer by a company that wants to change the terms of their bonds (amend, waive, extend, etc). A LOT was so useless that it was separately papered from all the material information about the offer so it could be easily tossed. A LOT would not dare comment on the actual terms of the debt tender offer. That important information was left to a far prouder document called the offer to purchase (the “OTP”) 

I’ll risk a tangent. For those curious, the more important and actual terms of the offer, the OTP or Prospectus, would be sent to the banking team at a top Wall Street bank. It probably would not be read by these bankers, but by their internal lawyer (if at all). Internal bank lawyers were generally paid to attend meetings and read legally “material” but commercially unimportant documents like the OTPs. The bank lawyer was responsible for commenting on whether or not the terms presented were “standard” or “customary”. If you needed something more formal or expert you’d go back to outside counsel. 

If the terms of the offer were “standard” and “customary” then no actual confirmation was required from the bank lawyer and they would say nothing. As far as everyone was concerned, that was best. Important business people on Wall Street don’t trifle with lawyers in the ordinary course. So, a lawyer that didn’t comment because the terms were standard was a lawyer that could be relied on and knew their job well. To be fair, if you knew what you were doing, most terms were customary and standard. It was the less capable lawyers that unnecessarily raised alarm bells on issues that weren’t really issues at all. So, if you were really good, no comment was typically required, expected and appreciated. And as all lawyers know, if we can get away without saying anything, then we really aren’t at risk, and a well paid Wall Street lawyer not at risk is one that is sated and happy as a proverbial pig. This is a pretty good Pickwickian example of the extraordinarily expensive, symbiotic relationship of professional silence on which trillions of dollars of financial instruments are traded every single day. It only breaks down when people actually don’t do their job, fail to identify what is not customary or standard, and when that happens, all hell breaks loose. 

The LOT, however, has no relevance to this material, silent exchange of trillions. As a new associate, I couldn’t be trusted with something that important. Thus the LOT was my first, most daunting, stressful, drafting assignment of my entire career. And somehow the LOT, feeble unloved transaction document that it is, managed to provide me with some of the most valuable substantive knowledge of the workings of Wall Street, and some of the major philosophical underpinnings on which I would build a reasonably successful career. What an amazing letter of instruction! 

I began reading the LOT that would serve as the precedent for my draft. On first review I found it completely incomprehensible. The precedent was an exchange offer swapping old notes for new notes. I had taken Securities Law in law school so understood the declaration that the Notes were registered under the Securities Act of 1933 and that was significant. I did not understand the role of an Exchange Agent, the S-4, the guarantees of signatures, TINs, the DTC, or how the LOT was grounded in regulation. Google Search wasn’t the omniscient legal scholar that it is today. I was completely lost. 

But you gotta start somewhere. So I read, clause by clause, looked up every term, pulled every cross reference to the US securities laws, and read the treatise summaries reviewing the importance of those clauses. Then I stumbled on this institution called DTC, the Depository Trust Company. When I couldn’t figure out what it was, I went to the library, which still had real books back then. I wandered and read random things and relevant things and generally enjoyed the peace and quiet and great views of New York City at night.

It was 9 o'clock at night on day two of my LOT adventure and no one was really left in the office except some red eyed unwashed senior associates that were playing their role as Atlas of firm productivity, preparing to be partners. I dared not ask them a question – I could be eaten or something. There were a few young associates like me, no doubt trying to discover and understand the obscure mathematical operation of a purchase price adjustment mechanism or some arcane provision of the US Securities Laws. So, lacking mentorship and guidance, I resolved that rather than schedule a meeting with the partner to get his view on DTC that I would call DTC in the morning. 

That call was both exciting and constructive. Exciting because this was the first time I actually spoke to someone outside a law firm. I was moving and shaking on Wall Street. Constructive because I was directed to a middle manager at DTC that knew everything about DTC. I learned that DTC acts as a nominee holder of bonds and is of fundamental importance. They custody over $87 trillion in securities now. The DTC rep had never spoken to a big law lawyer before and felt enamored that someone cared to ask about his job, and so he talked a lot and I learned a lot. In consideration, he asked if I would buy life insurance from his brother-in-law at Northwestern Mutual. I still have that life insurance policy today. 

By the time the week was over no one had called me to obtain my work product or chat. I’m pretty sure at this point my seniors had completely forgotten about me or maybe they just didn’t know where I had hidden. Some young associates probably went lost for years prior to technological tracking. We were a class of 100 newly minted lawyers so that is bound to happen, and the partners and seniors have their own assignments and clients and lives. The weekend came and I wanted to push ahead in my mastery of the LOT. 

On reading the LOT for the fiftieth time and having the benefit of this intensive and comprehensive research I concluded it was a terribly constructed document and could be vastly improved if it were entirely rewritten by me. This would be my great first contribution to the field of law. As a first year associate I could make my mark by fixing this nonsense of a document and draft something people could read, comprehend and action. 

On I went, rewriting the entire LOT. I changed the order, content and the font of the document. Nothing was the same, but everything was better. I will grant myself some credit here, it was absolutely better – best damn LOT ever written if you ask me. On completion, I was absolutely spent but eager to deliver my work product to the partner. I got on the partner’s calendar for a meeting – what a long two days it was to get in front of him, and he was the relationship partner for a major client. I itemized my questions and prepared my defense of anticipated questions. I was prepared to impress. 

I charged into the partner’s office with confidence and successfully but just barely managed to not trip over the glass cocktail table between me and the hot seat. I put my LOT on his desk and he picked it up to peruse the document. Do I jump in and explain to him why I rewrote the LOT, why I drafted this opus magnus, or do I stay silent? I stayed silent. With an eyebrow raised, he says “What was your approach here, Chris?” I explained it all, bumbling in some five minute monologue that was well-rehearsed but came out Klingon. 

“Uh huh,” he paused. “Well, looks like you really thought this out. You know this is all electronic now in the bank systems? I don’t even know why we draft these now at all to be honest, computers and such you know.” 

What a sinking feeling. Emotionally, I wasn’t a deflated balloon, I was the Hindenberg. #%@!% Technology! But, by the end of the meeting I had been asked to draft the OTP, and specifically asked to grab a template from a senior associate … What a relief and what an accomplishment. 

About fifteen years into my career, when in a position of some authority and managing about 30 attorneys at a major firm, I would periodically spend scheduled time with my junior attorneys. Some were doing great and some were struggling. Often I would get questions like “I don’t understand how you do what you do. I don’t see any of the issues you see. I need to be able to comment and contribute the way you do and I can’t .” A lot of these statements were colored with frustration, exasperation and a concerning sense of failure. These sentiments weren’t a fair reflection of their talent. These young attorneys were tremendously more talented than I was at that stage of professional development. We’d embark on a long discussion about important research treatises, legal templates, time allocation, better communicating with colleagues, and all that. I’d assure them they were doing well. 

In my opinion, new attorneys and finance professionals are better equipped, better prepared, more mature, intelligent and sensible than my contemporaries and I ever were. What I really want to say to these young attorneys and professionals is something along the following lines: “You don’t understand, I was an awful junior lawyer, terrible at what I did, and I’m not sure I’d keep myself around today if I knew how bad I really was.” Eventually, I would share my LOT story with them to assuage their anxiety and sense of failure because it seemed to give some perspective. 

It’s hard to imagine how being slow to learn can be a professional advantage, but it was really important to my professional development and ultimate success. I think there are a couple of reasons why. 

First, I was self-aware of my ignorance and I knew I could fail and be fired from this privileged overpaid first job. There was no safety net other than that expensive law degree that I had left on the floor of the back seat of my car (for over a year it turned out, with french fry stains to boot). Self-awareness that I didn’t know anything in this big new world, and wanting to make my fortune and future in it, and appreciating that I might not achieve that, was an important motivating factor. In short, there were real consequences to sucking at your job, and that problem was mine alone as I embarked on my new career.

Second, a top-tier education had gotten me into this elite world of finance filled with potential, but the opportunities that I was presented with were actually quite limited. The LOT was what I had in my first days because that was what I was given and asked to do. Choice was not part of the equation. I didn’t have a buffet of options to select from on assignments. If you wanted to work with such and such partner, or be in this particular corporate practice group, you did what was assigned, and I got LOTs for a couple weeks and weekends. What I liked, what work I thought worthy of my time, or whether it was challenging mattered not at all. So, LOTs I did, and I took up that job with all the skills and enthusiasm I could muster and sought to draft the best LOT I knew how. Not because it was important or relevant. I had no idea what was important or relevant. I knew what I was given, and that was limiting in one sense but liberating in another. The LOT was important to me because that was what the organization asked of me, and I needed to do it well. 

Third, as a motivated know-nothing I was a wonderfully curious if misguided beast of a student. Wasteful in the application of my time and energy, I wandered and engaged with all sorts of things; things that were relevant and useful to some objectives and things that were absolutely, most shockingly not relevant at all at times. I would bang my head against the wall, run into dead ends, and suffer terrible bouts of befuddlement. I would ponder the absurd and concern myself unnecessarily with the ridiculous and remote. I would read about things that mattered and things that didn’t matter at all because I found a book or an article laying somewhere, hoping random engagement would provide insight or maybe just some relief from my great intellectual toil. I embarked on a self-education program that was inefficient and terribly frustrating to my superiors and many other people in my life. But, little by little, I learned more and more. My curiosity led me to discover the basic architecture of the world I was responsible for knowing and becoming an expert in. This happened in no particularly organized or thoughtful way. It happened because I was committed to simply knowing more and I pursued my curiosity wherever it led me. 

In short, I was a curious ignoramus with limited opportunities, a hard head with a persistent drive of neanderthal proportions, and suffered from a fantastic fear of failure. As bad as these things may sound, they were key to me becoming in time what some would say is a talented finance professional that is pretty good at what he does. There were a number of things that I was not – genius, ivy league graduate or Stanford drop-out (what’s better nowadays?), self-actualized, balanced and moderated, naturally predisposed to success, brought up in a Wall Street family, exacting and precise in thought, cunningly efficient with my time and energy, well-organized or disciplined. Those were qualities some had, but most of my colleagues and I certainly did not. 

There were also some really important virtues held by my seniors who were responsible for me. 

First, they gave me my space and routinely ignored me and went off and did their own thing. I would go for days without hearing from any of them. At times this induced absolute panic and seemed unfair, and at other times this absence was much needed relief. It allowed me the chance to grow in my own way without constant measurement, pressure and judgment from those on whose every word my future depended. I also wasn’t micromanaged to the highest level of efficiency because I was young, wasn’t worth the investment of time, and they had more interesting things to be concerned about. I wasn’t a widget producing profit hamster vital to their annual measures of success and profit. I could fail, quit, win the lotto, move on in life, and all that was within the realm of possible and just fine. I was replaceable and my future success was not inextricably linked to their own. I wasn’t entitled to more than that and not being important to anyone was critical to learning how to become more important to everyone, including our clients, over time. In short, I was lucky to be there and everyone had that healthy perspective on where I stood, wedged into the ground below some cornerstone of the weighty pyramid that was this elite Wall Street law firm. 

Second, my seniors tolerated my process of discovery. Perhaps they did so in consideration for their extended absences. Regardless, they were accomplished and secure enough in themselves and could afford to do so. I just now really have some sense of how much billable time they wrote off because it became clear to them that I was on some misguided research adventure akin to Shrek in a flower garden. They didn’t yell at me about this – most of the time. Sometimes I’d get a look or a raised eyebrow when reviewing the billing diaries. Occasionally I’d hear down the hall a yelp followed by an explicative at the lost value that could have been charged to a client that was instead invested in my intellectual wanderlust. At times it became too much and then it was corrected with a fair bit of bottled up explosive anger that could be viewed as abuse today. In response, I would overreact and unconstructively spend time cowering and moping in my office, internalize how awfully stupid I was, and eventually get over it and move on. It wasn’t really abusive at all. It was a much needed correction that was a well deserved moment of instruction. Sometimes we need to be told that we are doing things the wrong way, and there is just no other way to look at it. And sometimes because of that correction we learn our lesson and repeat it less often than we otherwise would. It keeps us on the rails and inside the guard rails. We don’t have to be respected as equals to be well respected, particularly when we are doing stupid stuff that really is in no one’s best interest, including our own. 

Third, my seniors always expected more of me. There was never anything in the end that was perfect or good enough. There was always something more to do, to learn, to be achieved, and to be improved on. There was this seemingly endless horizon of professional expectation not because I was talented or great at what I did or special or unique, but simply because I was there. I had a great job. I was handsomely paid, and they expected that I valued that consideration and would deliver more to them, every single day, because that was the deal. This arrangement was not defeating or humiliating to me. It was not belittling or disrespectful of my humanity or sense of self worth. It was not a big scam or a pyramid scheme to suck the life from me like some occupational vampire. It was the deal I signed up to and it worked out really well for all of us in the end. Opportunity was given in expectation of results. It was my job. 

(All this good stuff and professional development that I experienced makes me wonder – how do we replicate it all in a remote working world?)

The qualities that defined the success of my professional journey seem to be under attack today. Socially, professionally, and philosophically, the current view is that the environment that grew professionals like me was just built wrong. Even worse, many believe it was somehow destructive and abusive to our moral fabric and our ability to find sustainable happiness. 

The consensus is that young professionals deserve a more balanced and understanding approach to professional development and training; a more balanced and healthy approach to life. We need to respect weekends, extend holidays, provide flextime schedules, remote working, guidance counseling, support and mentorship networks, consistent systems of review, and positive reinforcement – and not just a few of those things, they need all of them at once, and they need them all the time. Respecting an individual’s humanity in ideal is manifesting itself in practice in a way that is feeding a strong sense of entitlement. And worse, a consensus is emerging that today’s youth shouldn’t really do anything or get started in life until they are certain an opportunity meets all their needs. Nonsense. Better leadership, positive environments and intense personal reflection are good things, but a great professional landscape matters not at all if we don’t get our young professionals to throw on their rucksack, lace up their boots, and charge into the unknown jungle that is life and career. 

I challenge the conclusion that the way my peers and I matured and were trained in our professional life was misguided. We have worked hard, succeeded most of the time, achieved great things, and built incredible lives filled with wonderful experiences. No matter what data may be presented by the dire and doomsayers about how unhappy we have all become in our midlife crises, we have created a world with more opportunity for joy, wealth, happiness and prosperity and potential than any world that existed before us. 

In doing so we were grounded by the virtues that were important to us, principally that hard work and a sincere commitment to the service of others (and not ourselves!) leads to personal accomplishment and happiness. We owe it to the next generation and the one after that to continue to embrace those virtues, preach them, and hand them down as the most valuable assets of our character. Let’s teach youth to find their own purpose. Teach them the joy of hard work, the thrill of winning over your fears, the awesome potential of a stubborn person with purpose, and celebrate the hard work that creates celebrity, not celebrity itself. Instead of reaching for gratification, throw yourself into the fray. We must talk admirably about all these virtues that defined us, and by better sharing our values with them we may find they are not as lost as we are so convinced they must be.