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The Investment Banking Deal That Finally Broke Me

Updated: Feb 19, 2022

As I look back on my experience in financial services, I am delighted to share some of my life-changing career moments in the hopes that they can inspire you to make important changes in your life.

To read the popular Social Musings by Austin post from last year about the Story of My First Day on Wall Street, click here.

This week, I share the Investment Banking Deal that forced me into the realization that I needed to find another job in finance.

I remember specifically the moment I knew I could not work another day in investment banking.

I was standing in the shower in my New York City apartment in NoLiTa near Broadway and Lafayette Street.

For every day during the previous month, I had toiled at my Midtown Manhattan desk from 8am until 4am, followed by a scant few hours' sleep and then back to the office to work another 20-hour shift.

It really didn’t matter if it was a weekend, my work hours were always the same. It was like I was stuck in a workaholic's version of Bill Murray in the movie Groundhog Day.

My employer, JPMorgan, was pitching for a major piece of business, potentially one of the most lucrative of the year 2002.

Since I was a highly-regarded junior investment banker who had done good work for the Vice Chairman (one of the highest-ranking females at the investment bank) on another deal involving one of her largest clients, I had been added to the deal team that was going to “pitch” for the business.

“Pitching for the business” as the Investment Banking Analyst on the deal team involved building a financial model in Excel that envisions every single potential merger and acquisition (“M&A”) scenario and provides an estimate of potential shareholder value for each scenario.

The goal of the exercise is to maximize return for the shareholders taking into account the elements of taxation, feasibility and sensitivity.

I spent every single day and night for 45 days working on both the financial model and corresponding “pitch presentation,” which was the visual representation of all of the numbers from my Excel model.

These slides I created would ultimately be unveiled in the client meeting when JPMorgan's senior investment bankers would pitch against its competitors to earn tens of millions of dollars in investment banking fees that inevitably would be generated as part of the transaction.

In order to wow the client, my PowerPoint files would be produced into novel-worthy, bound, glossy pitchbooks by JPMorgan’s Production department and display over 100 pages of colorful charts, printed tabs and diagrams.

The hope was that this pitchbook would captivate its audience with scores of numbers on every page, weaving a numerical story of what the client should do strategically, and why they should ultimately hire JPMorgan to advise them through every necessary step of the complicated process, which loomed like a financial markets minefield.

As we approached the client meeting on one Thursday during this 45-day stretch, the Vice President in the M&A group who was supervising the junior investment bankers’ work reviewed the entire presentation to get the pitch ready for the client meeting.

It was 8pm that Thursday evening, and I had probably just finished dinner at my computer.

The phone rang at my desk, and I looked away from an Excel spreadsheet with which I had spent more time than anything else (even my own bed) over the past month.

I answered.

"Hello?," I murmured.

The senior M&A banker was calling all of the junior members of the deal team to his office downstairs.

"OK," was all I could muster.

With a significant amount of trepidation, I took the elevator down to the M&A floor of 277 Park, where JPMorgan's Investment bank was housed.

As I crowded into his office amongst the others on the deal team, I noticed that he had marked up and completely revised EVERY SINGLE PAGE of the massive deck. Every slide was a complete redo; I have never seen so much red ink in my life.

I also knew that I was the ONLY ONE who would have to do the work as well.

At the end of the meeting, this now legendary investment banker who is still doing mega deals on Wall Street looked right at me. He handed me the large stack of his PowerPoint markups and said: “I want to see this again on Monday, with all of my edits incorporated.”


What a gut punch.

Mind you, I am now at the office at 10pm on a Thursday with a Monday morning deadline.

I knew that my weekend was toast.

As I returned to my desk in a disoriented daze after the disheartening news, my mind raced.

Settling myself in my chair as I threw down the PowerPoint edits, I thought:

I will be inside this building working for the next 72 hours.

While most normal people will enjoy a weekend of much-deserved free time and rest, I will be here in this Park Avenue cubicle staring at a computer screen praying that I can please my boss on Monday.

Happy Happy Joy Joy.

Not that I was missing much anyway.

I had no life.

For the past few years as an Investment Banking Analyst who had recently been promoted to Associate, I had spent the vast majority of my life immersed in Excel spreadsheets and PowerPoint presentations.

And like so many weekends before over the last few years, I would sleep very little as I struggled to meet my deadline.

Let me tell you something about pulling all-nighters.

When you experience sleep deprivation, the world takes on a different sheen.

You find yourself laughing at mundane occurrences.

You find yourself speaking to yourself in different languages and tones of voice.

You find yourself commiserating with your miserable colleagues who are also stuck in the Investment Banking maelstrom, and you wonder frenetically what life must be like for the "normal people" who have a 9-5 job.

When pulling all-nighters, I think your brain is oxygen-deprived or some important neuro-chemical that comes with sleep desperately needs to be replenished, and as a result, you feel like a robot.

Robotically, I endured a three-day stint of minimal sleep supported by caffeine and Adderall.

And now here I was in the shower.

It was the Monday morning after the weekend of all-nighters to get this presentation ready for the Vice President.

Barely alive, I hung my head submissively allowing the shower water from the subpar New York City water pressure drip onto my hair from my subpar New York City showerhead.

My chin was on my chest, as in my former college fraternity days when we, as pledges, would have to line up in the basement and avoid eye contact with our pledge-masters.

As I let the water run through my hair and down my face and took stock of my situation, I thought that maybe I hadn't progressed that far in my life after all:

Here I am. Supposedly with a great career. Having an amazing experience. My parents are so proud.

Yet all I feel is exhaustion and mental fatigue.

There is no bright light at the end of the tunnel. There is no meaning in my life.


At that very moment, I decided that I needed to find another job.

I suddenly found that achieving balance in my life was more important than success, and while this awareness led me to several other jobs in finance, it was not until a near-death experience recently that I realized that exploring my childhood passions was more important than striving for financial reward and career progression.

So wherever you are in your career, make sure that you aren't sacrificing the other important things in your life just for hedonic, extrinsic factors such as money and social status.

NOTE TO READERS - This text is an excerpt from my upcoming memoir. In the meantime, please check out more excerpts from my book and other original stories on my Social Musings by Austin Apple podcast: Link here.

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