my "oh, shit!" moment (and what I learned from it)


This is the third part of the weekly blog series, where I'll be posting a new excerpt from my upcoming book, Living Forward, Looking Backward, right here each week.

If you missed the first two posts, go back and check out Part 1  and Part 2.


My "Oh, Shit!" Moment

- the bigger the failure, the more learning you gain -

As backward as it felt in the moment, I realized that one of my life’s most meaningful lessons had just been delivered through a devastating mistake. The bigger my failure, the more colossal my loss, the more learning I gained.


Once Greg and I were back stateside, my story continued in the normal workingman’s world of riding a train to and from an office building each day. I worked for a consulting firm in a fancy downtown Chicago skyscraper, and I considered it my first “real job.” There was a human resources team, a closet full of pens and notepads, 10 different options of coffee, and people who worked the same hours every day to take home the same paycheck every two weeks.

Before my consulting job, I helped build the sales team at a startup company that distributed branded tea. I also worked at a leadership-training nonprofit, and I’d had some other short-term gigs. This, however, was a major-league consulting firm. Our job was to provide financial valuation expertise to headlining legal cases and the law firms that handled them – Apple vs. Samsung, for example.


“Oh, shit.”

I don’t really cuss. I don’t have anything against those who do, it’s just not me. My friends laugh when I let a curse slip because it’s something of a rarity. It wasn’t a slip this time, however. I really meant it. I had screwed up big time and I felt horrible. I’d been given a tremendous amount of responsibility as a first-year consultant and I dropped the ball at the single, most critical moment of my project.

This was my “Oh, shit!” moment.

My job was to build the financial models behind the cases that vice presidents brought to the firm. Simply put - I created really, really big Excel spreadsheets that translated a bunch of raw data into one single price so that a lawyer knew how much money a certain technology or legal case was worth, and under what conditions. That doesn’t sound like fun, but it was. Building financial models is like putting together a big puzzle. It was tedious work sifting through thousands of pages of deposition testimonies, corporate files, and legal documents to collect the data we needed to create the models, but once we did, I liked the intellectual challenge.

We worked as a small team. Jeff, Chris, Jon, Steve, Ashley, Ahmed and I were all pretty tight-knit. It was good to have friends in the office during those late nights. We all worked on the same cases, but after a few months on the job, a vice president, Chris, needed help with a new case from just one consultant.

The consultants who typically worked on Chris’ cases were all tied up with other projects. I was known for being able to chew through large stacks of legal documents fairly quickly (I’m a fast reader) so I was given the chance to own the financial model for Chris’ case. I was thrilled. It was an assignment I could build my reputation on. The case itself was intriguing, too. We were valuing the technology for a videogame system, which I found more appealing than some of the cases other consultants were stuck with (valuing parking garages or gravel piles, for example).

We had two months to produce a 100-page report and an equally large Excel model, which would be the final products for our clients. Chris would write the report and I would back up his conclusions with the financial model and corporate data.

The case progressed smoothly for the first month. The second month, I essentially lived in the office while trying to complete my work in time. I didn’t really mind the long hours, however, and my roommate, Daniel, also worked late. Plus, our clients gave me permission to put dinner on their expense account if I worked more than 10 hours a day. Free food, baby! I even opted to work late some nights just to expense my dinner. I was still building my bank account balance back to five digits after my summer travels.


“How’s that model coming along?” Jeff asked, setting a small orange basketball on my desk.

Jeff and I sat next to each other, separated by a low-profile cubicle wall. He had a picture of a fighter jet strung across one wall of his cube and a small basketball hoop stuck to the other. Whenever we needed a break, we’d take shots from different spots in the office and distract our other cube-mates.

Chris and I were about two weeks away from our deadline, so I shared with Jeff, “Pretty good. Coming along well. Chris is having me take a shot at writing some of the narrative for the report, so that’s cool.”

“Good stuff man, that’s not supposed to happen after just a few months in your role. Nice work,” Jeff encouraged me.

It was good to hear him say that. Jeff had more experience and a grueling yearlong case under his belt. It was one of the infamous war stories told around the office. He even had to leave his family’s Christmas party to battle through the case that year.

“Thanks dude. Chris is making my life pretty easy – he’s fun to work with. I’m diggin’ it.”

Jeff laughed in agreement, “I’ve never worked for Chris directly, but that sounds like him. Whenever he’s at Lloyd’s, I’ve never been able to buy myself or anyone else a drink. He always picks up the tab, even if he just sees you across the room and isn’t sitting with you.”

“Ha! Don’t I know it,” I grinned.

Lloyd’s was the bar on the first floor of our building. I had been the beneficiary of Chris’ dependable generosity many times. On half-price appetizers night, he would walk through the office to rally as many people as he could to go down to Lloyd’s. There wasn’t a single staff member who didn’t love Chris. While there were some vice presidents who you knew would be ruthless at worst and uninteresting at best, Chris defied every stereotype. I actually enjoyed walking into his office every morning.

I continued, “You know, it’s funny. To me, Chris is totally understated and humble, yet the most interesting man in the world. He speaks quietly and doesn’t push any bravado across the table at you. But if you begin to ask him questions, you learn that the guy runs trails barefoot, builds drones in his garage, and races snowmobiles. I’m sure there’s more I don’t even know about him yet.”


“Nate, new news. Stop by my office, okay?” Chris said as he walked by my cube.

I always appreciated that Chris was human enough to walk to my cube to talk with me. He didn’t just beckon me with an email that said, “Come here. Now.” I wondered what would be waiting for me behind his office door. Part of me hoped Chris had just added a new set of exotic fish to his five-foot tall tank. The realistic part of me said it couldn’t be that fun.

“Hey Chris, what’s up?” I asked, standing in the doorway waiting to be motioned in.

We were two days away from our project’s deadline, when we’d submit the final report to our clients and the courthouse. He waved me in and brought me up to speed.

“We had some new documents sent to us overnight. The opposing counsel just released them. An amateur move – they’re trying to spin our wheels with last-minute data. There could be nothing in the files, or… there could be something major in them, and they’re hoping we don’t find it. Either way, we have to know, and we have to know soon.”

My nerves began to tingle inside me but I replied calmly, “Sure. Anything else?”

“Yeah, one more thing. Make sure someone QC’s the model for us,” Chris said, referring to a “quality control” process where someone outside our case double-checked my work for accuracy.

I grabbed the small, black hard drive from Chris’ desk and reassured him, “Yeah, will do. Dave’s helping me out with that.”

I took the long way back to my desk and reassured myself I wouldn’t find any bombshell documents waiting on the hard drive. Most likely, it was just a stall tactic. Besides, if there was something material lurking among the new files, we’d have the chance to argue that a last-minute document shouldn’t be allowed to influence a report compiled over the course of months.

Yet, I couldn’t shake the feeling that bombshell document or not, this surprise wasn’t going to be a good one. I even missed what Jeff asked me as I walked by, consumed in thought.

“Hey. Hey. Hey! Nate! What was that all about?” Jeff said after managing to grab my attention.

“Oh, just a little gift from opposing counsel – more docs to go through before our report is due. You know, the one due in two days...” I filled Jeff in on the hard drive and how now, for the next 48 hours, I’d be a ball of nervous energy wondering if I had missed something important.

“Oh man, that’s a bummer. Sorry about that. Can I help out?” Jeff offered.

“Eh, it’s fine. It’s only like another 100 files. I should be alright. Thanks though,” I shrugged and plugged the new hard drive into my laptop.


“I think we’re in decent shape – I’m going to grab a sandwich. Do you want something to eat?” I asked Chris, looking down at my watch.

My watch’s gold hands told me it was 7 p.m. – five hours before our report’s midnight deadline. I already knew that, though. I had been watching the clock all day to ensure I left enough time for last-minute edits. My parents gave me the watch as a gift when I first started working at the firm. It had a brown leather band and a gold-rimmed face, and I felt important and professional when I wore it.

On this particular night, however, my watch felt more like a tyrannical dictator. It was shackled to my wrist as an oppressive reminder that I wouldn’t have enough time to fully review our report before submitting it. The minutes continued to melt by, counting down to our midnight deadline. I figured that if I walked out of the office to get a sandwich, I’d distract my nerves and shake the dreadful thought that I had missed some critically important detail.

Chris typed fiercely onto his keyboard. “No, I’m fine. I just need to make one final change to one of these sections based on the docs we got – you go ahead.”

Chris called me shortly after I arrived back in the office with a grilled chicken panini. “Hey Nate, we’re going to make a minor update to the royalty rate – can you make sure this gets changed in the model?”

I set my half-eaten chicken and tomato pita bread on his desk and I rolled the change through my spreadsheet to update the final numbers.

It was getting close to midnight. I felt a bead of hot sweat slip down my back as I read through everything one last time, scanning for typos, spelling errors, or other items that the opposing counsel might use to discredit the veracity of Chris’ report. After not finding any additional tweaks, I pressed “send.” Our report was officially submitted to the court and forever sealed into the legal records. It couldn’t be changed, so come hell or high water, the project was done.

I eased back into my chair, believing we had completed our case. I drew a deep breath for what felt like the first time in two days and I looked at my watch again. Now, it felt more like a scoreboard, congratulating us for crossing the finish line.

“Want some?” Chris asked, wheeling his desk chair over to a case of black-labeled wine bottles in the corner of his office.

“Oh yeah! Thanks.” I accepted and took a more-than-generous sip of wine well-earned. It was good wine to be sure, but it tasted even better knowing we just submitted the report for my first big case.

We began to cherish our wine but our brief stint of joyous relief came to a screeching halt when the computer dinged with an incoming email.

“Uh, Nate…” Chris said, reading the email from our client. “The numbers in the report’s final table don’t match the numbers in the model. They’re off. Why?”

“Oh, shit.”

To this day, I’m not sure if I thought it, said it, or whispered it. I remember with certainty, however, feeling the heaviest, most crushing sinking in my stomach. I wanted that feeling to drag me down below the desk, through all 34 floors of drywall, and right into the basement where I could hide from the firestorm of anger that was sure to be unleashed on me. I had just let down the most trusting and encouraging vice president in the firm. I could own up to my own errors, but the report carried Chris’ reputation. I felt like I had just jammed a knife into Chris’ back.

I was red hot, trapped inside my own clothes. I wanted to run. I looked at my watch, hopelessly deliberating if I’d have enough time to make this right before Father Time declared midnight and decreed my mistake irreversible.

The silence in the room was deafening. I racked my brain for an explanation. I braced myself and came to grips with the fact that I’d watch my livelihood burn before me that night. I was marching toward the gallows. I was sure that my budding consulting career would spoil into nothingness as Chris moved Earth itself with his pent-up rage. I had no doubt that a tsunami of vitriol had been welling up inside of Chris, and my error had just triggered his ocean of wrath.

“Okay,” Chris said. “Let’s go home.”

I blinked.

“What?” It was all I could muster.

My initial horror transitioned into a slightly more manageable panic as I thought of solutions. I had to fix this; I was responsible. I was ready to sleep in my work clothes for the next three days, working ‘round the clock to pay some type of overtime penance for the catastrophe I’d just wrought upon my boss. While fixing the report would be a quick process, I wanted Chris to unload hundreds more hours of work on me, just so I could claw my way back into good standing with him. Your reputation is everything in consulting, especially in legal settings.  

“Yeah, it’s time. There’s nothing more for us to do tonight,” Chris said before his phone rang. “Hello, this is Chris.”

I couldn’t hear the conversation on the other end. The phone masked the lawyer’s words, which I assumed were scathing criticisms. I imagined they skipped all pleasantries and started off by yelling at Chris, “What the hell happened here?! It’s in the court record now! This is permanent! We look foolish!”

Chris spoke evenly into the phone, “This is what happens when we have documents given to us last minute, with changes in the case strategy and final edits all needed at the same time.”

To my disbelief, Chris continued, “I missed it. It was my fault. I just missed this one. We’ll send a redlined version tomorrow so you can resubmit it to the court.”

He spoke calmly, as if he had just woken up from a nap on some office hammock. I was dumbfounded and motionless. I stared at Chris as he set the phone in its cradle. “I think I’ll take a cab home tonight. It’s too late for the train now. You should do the same, Nate.”

I couldn’t believe it. Chris had accepted the blame for my mistake, flat out. No yelling, no crippling amount of extra work, no saving himself by casting the first-year consultant to the wolves. Somehow, he was genuinely concerned that I made it home safely.

“Uh, okay. But what can I do to help out tonight?” I asked once more. I knew I wouldn’t be able to fall asleep without doing something to dig myself out of my hole. I didn’t want grace to come that easily, you see.

“Go home Nate. There’s nothing more for us to do tonight. Sleep,” Chris ordered.


Do you remember how we said in Part 1 that stories keep things simple? That stories and the principle of paradox help us discover greater meaning in our everyday lives? This is never more visible than against the backdrop of our greatest failures, which often leave us confused and frustrated.

There has never been a perfect person in the history of stories. Well, at least in the history of interesting stories. Characters inevitably screw up as the plot unfolds, and a story’s core conflict is always rooted in the main character’s shortcomings. This is crucial because we all crave to see conflict resolved. Imperfect characters keep us engaged, sitting in a movie theater or reading a book for hours.

If not outright failure, at the very minimum, we prefer the characters we watch to have some type of personality flaw or past regret plaguing them. We relate to wounded characters. We root for them to pull through in the end because it mirrors our own experiences – we’re not perfect people either. I mean, can you imagine reading a book about someone who does everything right, and faces no opposition whatsoever? Of course not. We’d either tear the book in two before finishing it, or we’d finish it and feel like losers by comparison.

The same concept applies to our daily lives. While we shy away from conflict and we fear failure, these experiences serve as open doors to grace, growth, and new lessons learned.  We mature as we deal with the fallout from our mistakes. We become more interesting characters. If we can accept – and in fact, demand – flawed characters as critical to the stories we watch and read, we must learn to do the same in our own lives instead of viewing failure as a fait accompli. This perspective is the path to finding greater meaning in our most frustrating letdowns and confusing defeats.


I sat in a cab watching Jimmy Kimmel Live on the back of the passenger seat. It was helpful to focus on something other than spreadsheets, lawyers, and office buildings. I turned to watch the city lights stream by as the cabbie turned down Orleans, crossing the Chicago River. The city was still wide awake at 1:00 a.m. I wondered if the shadowy outlines in office windows were people huddled over Word documents, meticulously checking their work into the early hours of the morning to ensure they were error-free for tomorrow’s presentations.          

“How do you screw up as a cab driver?” I thought to myself, legitimately considering a career change. I debated if I’d be able to sit in a car for 10 hours a day and decided against it. Crashing into other cars for half the salary didn’t feel like a good trade.

The cabbie pulled up to my apartment and I tipped him double. He’d driven me home accident-free and it’s not every day, after all, that you get your job done without screwing it up.

I slid out from the back seat and walked into my apartment before dropping my keys into a wooden bowl. A loud, clanging noise echoed from our 15-foot tall ceilings. I wanted to wake up my roommate, Daniel, just so that he could ask me about my day. Then I’d have someone to commiserate with. No sound came from his room, however. I didn’t have a choice. Maybe it was best to go to bed pretending it was a normal day.

I crumpled into my sheets and rolled onto my back with a groan. As my eyes adjusted to the dark, I tried to grasp what exactly I should have been learning from my mistake. While I had screwed up before – hurt people I loved, failed exams, and other run-of-the-mill missteps – I had never fallen flat in such a way that I directly torpedoed someone else’s reputation, with the entire blame landing squarely on me. I racked my brain for some type of lesson to help me move forward and avoid repeating one of my most public failures.

Sleep evaded me as I stared at the ceiling’s plastered ridges and grooves. I ruminated over Chris so calmly instructing me, “Go home Nate. There’s nothing more for us to do tonight.” Those words haunted me. They didn’t offer any opportunity to atone for what I’d done. I botched our report in the grandest of fashions, yet Chris had no less respect for me. He treated me no differently. I couldn’t make heads or tails of it.

As backward as it felt in the moment, I discovered that one of my life’s most meaningful lessons had just been delivered in the form of a devastating mistake. The bigger my failure, the more colossal my mistake, the more learning I gained.

What’s more, Chris embodied a perfect picture of grace. He had entrusted me with our report, granting me full autonomy and responsibility. Still, I fell short. I missed the mark. There was no way I’d be able to repay him, and I knew that even if I could, he wouldn’t have allowed it. Chris readily accepted the blame for my error as soon as he discovered it. He showed me that the harder we fall, the more grace we receive.

In the same way, the collective story of our world, the “Big Story,” says that our author (God) didn’t create flawless characters (us) who produce error-free reports. Instead, He knew imperfect characters who can decide to love Him or walk away from Him, choosing conflict and a broken relationship, make for a better story. Knowing full well we’d fail, our Creator not only proceeded to write us into existence, He made grace central to our story’s resolving event – death on a wooden cross we built for his son over 2,000 years ago.

In my finest moments, that sentence, “Go home, Nate. There’s nothing more to do tonight,” rings out when I’m affected by a friend, colleague, or family member’s mistake. Chris helped me see that if I’ve been given a second chance, how can I demand perfection from someone else? I try to ask myself in moments of mindfulness and my own missteps: what’s the lesson hiding behind this failure?  


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