Is Investment Banking Stressful?

The stress isn't the hours. I expected the hours. Everyone told me about the hours. What nobody told me is that you can't plan anything. Not "you work weekends." That I was ready for. I mean: you cannot make a plan for 8 PM tonight because at 6:47 PM your VP is going to send you an email that says "can you pull the precedent transaction comps for cardiovascular devices, need by morning" and your evening is gone. It's the randomness. You're never truly off. You're never in a state where someone can't reach into your night and take it.

Last month I had tickets to see my college roommate Shane play a set at a bar in Williamsburg. I bought them two weeks in advance. I told my associate, Christine, about it. She said "should be fine, we're between deals." At 4:15 that afternoon, our MD landed a new pitch. Christine sent me the target company's financials and said she needed a preliminary valuation by 9 AM the next morning. I left the tickets on my desk. Shane texted me the next day: "Missed you last night." I said "work thing." He's an audio engineer. He does not understand what "work thing" means in this context. To him, a work thing is staying an extra hour. To me, a work thing is the dissolution of my entire evening with 2 hours and 45 minutes of notice.

The error. The potential for error. That's the stress. Everything we produce has numbers in it and those numbers inform decisions that involve tens or hundreds of millions of dollars. If I build a model and there's a mistake in the revenue growth assumption, and that mistake flows through to the EBITDA, and the EBITDA flows through to the valuation, the client could make a decision based on a wrong number. They could pay $22 million too much for a company. Or they could sell for $22 million too little.

Three months ago I found an error in a model that one of my analysts, Rohan, had built. It was a formula issue in the depreciation schedule. The formula was referencing the wrong row. It was off by one row. That one row meant the depreciation was understated by $1.8 million annually, which overstated the EBITDA, which inflated the valuation by about $14 million on a $200 million deal. I found it at 11:40 PM the night before we were sending the CIM to buyers. I sat there in my apartment in Beacon Hill looking at this formula and my hands were shaking. Not figuratively. Literally shaking. Because if I hadn't checked, that $14 million error would have gone out to fifteen potential buyers, and by the time anyone caught it, the credibility of the entire process would be compromised.

My boyfriend Soren was asleep in the next room. I fixed the model, updated the output pages, emailed my VP the corrected version, and then I sat on the kitchen floor for about ten minutes because I needed to be somewhere that wasn't my desk chair. Soren found me there when he got up for water. He asked if I was OK. I said yes. What I meant was: I just prevented a very bad thing from happening and nobody will ever know, and that prevention is the whole point of my job, and it terrifies me that the next one might slip through.

The thing that stresses me out most is the deal dying and knowing it's not your fault and also knowing it doesn't matter. We spent four months on a deal last year. Leveraged buyout of a business services company. I ran the sell-side process. We had a buyer, we had a price, we had a signed LOI. Three weeks from closing, the buyer's credit committee pulled the financing. Market conditions. Rates moved. Their fund decided the risk-return wasn't there anymore. Deal dead.

Four months of work. I had two analysts on this deal full-time. Hanna and Kwesi. Hanna specifically deferred a two-week vacation to Australia to stay on the deal through closing. I told her the deal was solid. I believed it. And then on a Sunday evening my MD called me and said the buyer walked. I had to call Hanna and tell her. She was quiet for a long time and then she said "OK" and hung up. She rebooked the Australia trip but she looked at me differently for about a month afterward. Not angry. Just recalibrated. She learned that the thing you're killing yourself for can evaporate with a phone call, and there's no appeals process, and nobody compensates you for those four months, and the only thing you carry forward is the experience of having done it.

My wife Celina asks me sometimes if I "won" when I come home after a deal closes. I don't know what winning means in this context. The deal I spent four months on dying felt like losing. The deal that closed in six weeks felt like nothing because it was too easy. There's no clean scoreboard. You just keep going.

My body started keeping a ledger. That's the stress. Not the intellectual kind, the physical kind. I developed TMJ in my first year because I clench my jaw in my sleep. My dentist, Dr. Patel, fitted me for a night guard. He asked me if I was under unusual stress. I said "I work in investment banking" and he just nodded, like that was a complete diagnostic explanation. He sees a lot of us, apparently. Finance and law, he said. Those are his night guard demographics.

I also lost about 15 pounds in my first eight months without trying. Not because I was exercising. Because I was skipping meals. Not intentionally. You just forget. You're in the middle of a restructuring model at 2 AM and you realize you haven't eaten since the salad you had at your desk at noon, and by then you're not hungry, you're just running on adrenaline and the cold brew you bought at 4 PM that's still sitting there with an inch of liquid at the bottom that's basically coffee-flavored anxiety.

My roommate Kaia is a pediatric resident at NYU. She works awful hours too. But she comes home physically tired. I come home mentally vibrating. We'll be sitting on the couch watching something and she'll fall asleep in ten minutes and I'll be awake for another two hours because my brain won't stop running scenarios on the liquidity analysis I was building. The difference between her exhaustion and mine is that hers comes from doing something and mine comes from thinking about something. Both are real. But mine doesn't feel earned. It's hard to complain about being tired from sitting at a desk when the person next to you was on her feet for 14 hours with actual children.

The stress at this level is entirely relational. I don't build models. I don't make pitch books. I haven't opened a spreadsheet in earnest in about three years. What I do is manage relationships with people who are making the biggest financial decisions of their careers, and I carry the weight of that. Last quarter I advised the founder of an oilfield services company on a sale. His name is Gene. He built the company over 25 years. Employed about 340 people in Midland and Odessa. His entire net worth, his retirement, his family's financial future, all of it was tied up in this company.

We got him a good outcome. $165 million. But during the process, there were three weeks where the deal looked like it might fall apart over an environmental liability in one of the properties. The buyer's environmental assessment found potential contamination from a legacy well. The remediation cost estimate was $4 to $7 million. The buyer wanted to escrow $10 million of the purchase price against it. Gene wanted to escrow $3 million. The gap threatened to kill the deal.

During those three weeks, Gene called me every day. Sometimes twice. Not for updates, because there were no updates. For reassurance. He'd say things like "Tell me this is going to work out." And I would tell him that we'd find a path, because that's my job, but I also knew there was a scenario where it didn't work out and Gene would walk away from this process with nothing except eight months of legal bills and a company he no longer wanted to run. I carried that. I went to sleep carrying it and I woke up carrying it. My daughter Wren, she's 8, she asked me why I was "being quiet at dinner again" and I told her I was thinking about work. What I was thinking about was Gene, sitting in his kitchen in Midland, wondering if 25 years of work was going to resolve into a number or a lawsuit.

The stress I didn't expect is the ethical ambiguity. Not illegality. Nobody's doing anything illegal. But there are moments in a deal process where you're presenting information in a way that is technically accurate and strategically selective, and the line between "good advocacy" and "misleading the buyer" is thinner than anyone outside the industry would be comfortable with.

Last year I was advising a SaaS company on a sale. The company had a customer churn issue. Gross revenue churn was 14%, which is high. But net revenue retention was 108%, because their expansion revenue from existing customers more than offset the losses. Both numbers are true. Both tell a different story. The management presentation emphasized net revenue retention. The buyer's due diligence team asked about gross churn. We provided it. But we didn't lead with it. We led with the number that tells the better story. Is that dishonest? No. Is it the whole truth? Also no. My colleague Oliver and I had a conversation about it. He said "we're advocates, not auditors." He's right. But I went home that night and my partner Aoife asked how my day was and I said "fine" and what I meant was: I spent the afternoon deciding how much truth to put on which page and I'm not entirely sure I got the calibration right.

That's the stress that doesn't get discussed on Wall Street Oasis or in the recruiting brochures. It's not the hours. It's the accumulation of small judgment calls that are each individually defensible but collectively make you wonder what kind of professional you're becoming. Aoife is a barrister. She has clear rules about what she can and can't do. I have guidelines and norms and "market practice." Market practice is just what everyone else does. It's not the same thing as right.