In this conversation, Matt Ochalski (Booth '23) shares his journey from working seven years in debt capital markets in New York to pursuing an MBA at Chicago Booth School of Business. He discusses his methodical approach to the application process, including his extensive planning timeline, managing applications while working 90-hour weeks in banking, and his authentic essay strategy centered around bringing kindness to the professional world.
Matt emphasizes the importance of authenticity in applications, detailing how he wrote about kindness as a core value in banking and how this theme helped differentiate him from other candidates. He also covers practical advice on managing recommenders, visiting schools during the pandemic, and making the most of business school experiences. The conversation concludes with insights about Booth's culture, balancing academic rigor with social opportunities, and successfully pivoting within the banking industry.
In the professional world, people always think that you have to be tough and you have to be resilient and you have to be strong in order to get ahead, and oftentimes I think that can be almost a conflict of interest, or that in order to get ahead you have to almost push people out of the way. I wrote on a lot of my essays the importance of kindness. I come from a banking background and I am going back into banking, a very different part, and for me kindness was something that was not necessarily a value or a virtue that was highly important, and I think it should be.
My name is Matt Ochalski. I am a born and raised midwesterner, originally from a town called Lake Forest, which is about 45 minutes north of downtown Chicago. I didn't go very far for college. I always thought I was going to go to the West Coast and get far away from my parents, but that did not end up happening, so I ended up going to UChicago for undergraduate, down in Hyde Park. It was a great experience, close enough that my parents could visit me once in a while, but still far enough away where they're not there every single day.
Did you enjoy undergrad? UChicago's got a reputation where fun goes to die.
When I look back now, I probably have a better memory of it than at the time. At the time it was very difficult. I, like a lot of other people, was an economics major, which is what UChicago is well known for, and at the time it was a lot of work, a lot of late nights in the library, and a lot of problem sets. So now, looking back, I have much more fond memories of it, but at the time it was totally study mode.
Even when I was an undergraduate, I actually was in a program at UChicago that was dual enrolled with Booth, so I was taking classes when I was 19, sometimes with people that were 29. Now that I'm back at Booth for the second time, it's very interesting to come back and be in that older position and see the students that are not even 21 and having class with them. It's a very different experience to do it.
It is very much full circle, and you realize just how smart some of these undergraduates are that are in some of your classes, and you just are amazed at how bright they are.
After graduation at U Chicago I ended up working in banking. I worked in debt capital markets, helping companies to raise debt by issuing bonds to institutional investors, and I did that for the last about seven years, with about five of those being in New York prior to coming back to Booth. I also had a specific focus covering clients within the tech, media, and telecom sector, so some of the big players in that area were people that were clients at the time. It was a very good experience, very exciting to be in New York, but ultimately I just wanted something different and wanted to pivot within banking. I also felt like it was a really good time to come home, visit my parents, spend some time with family again. So I knew I probably wanted to apply to business school, and that's why I ended up back here.
No, I honestly never realistically thought that I would go back to business school. I never really saw it as something that I needed to have. Especially within debt capital markets, an MBA is not necessarily something that you really need to advance within your career. You can make a very good career and move up the ladder without that. So for a long time, when I first started, I never anticipated going back to school. I thought I would just stick at a bank, and maybe switch banks, still doing DCM.
But ultimately my interest just changed at a certain point, and the easiest way to make that transition and get the skill set was to go back to business school and to make the connections. It's a little bit easier to have the banks come to you when you're recruiting at a business school, rather than me having to much more proactively try and form connections.
The thing that really saved me is knowing that I wasn't going to rush the process. It was very, very challenging at the time because I was still working a lot of hours, probably about 90 hours a week. So it was really challenging and I had to really just focus on when I'm at work I'm at work, and when I'm not at work I have to devote all of my energy into different parts of the application. I'll be completely honest. I really wanted to take as much time and do it well and have all my application components done and not be trying to finish something at the last minute.
So I really planned for this. When I knew that my interest changed and I wanted to go to business school, I said, okay, what's a realistic timeline? So I think it was probably 18 months to two years of me, whether it be studying for the GMAT or GRE. I initially started at the GMAT and then decided I'm going to take the GRE because I do better in that format. And then thinking proactively even who are my recommenders going to be for these applications, and do I have a good enough relationship. I'm a planner by nature. I thrive in a setting where I can schedule my time and think proactively about something, and so that is something I think that really helped me in the application process: being organized early and sticking to a timeline.
My weekends were definitely devoted to studying for a lot of the tests, and when I had time, trying to work on a lot of my essays.
I was at the very early stages. I even went to go visit you at Harvard at the very beginning of my process, so probably in fall of 2019. I was still trying to do my due diligence on which schools I was going to apply to, and slowly trying to visit schools. I was in New York, so trying to make the trip up to Boston. I knew some of the schools like Kellogg, and I knew Booth from the Midwest. What were the other ones, whether it was Wharton or whether it was Dartmouth, anything going to NYU or Columbia? So trying to tick those off and see them in person. That was in the fall of 2019.
And then we know what happened in spring of 2020. I was supposed to visit a lot of schools in the spring. I was initially supposed to visit some friends at various schools, not in the dead of winter, but COVID completely changed that. I would say that COVID actually helped me. Business slowed down in 2020 a little bit, so I did a lot of work and a lot of due diligence in 2020 when I maybe had a little bit more free time. So it benefited me from that sense, because work was a little bit lighter.
You can't go anywhere really, so what else is there to do but work on your applications, study, go on TikTok for some fun.
Did you post some dance videos yourself?
No, I'm horrible at choreography. I cannot to save my life do the choreography. I watch the TikTok videos, but no, I am not one of those people that can do that.
I was familiar with Booth and knew what Booth was like, and so everything was somewhat in comparison to that. I really wanted a really strong alumni community. I also didn't necessarily want to be in a rural setting. I really wanted to be a more urban campus, where I thought it's better maybe from a networking perspective and to be able to launch your career. From my perspective, that was something that was very important to me, being able to travel and network. I also think a general sense of community, like where do I fit in. And I did look at a lot of other schools as well. Booth was not just the one and be-all, end-all. But I think that the sense of community, alumni, and realistically access to career and job opportunities were the factors that really influenced me the most in looking for a school.
What was the final list of the schools you ended up applying to?
So it was Booth, obviously, and Kellogg, just from a perspective of family being here. HBS, Wharton, MIT, and NYU Stern. It is a lot. I might have bitten off more than I could chew during the process. Too much. It's hard. It was a lot. I think people think that essays are all really similar, but from my knowledge - and I don't remember what Booth's was - the essays, you cannot copy paste.
Once I knew that the application was going to go live, I started looking at what are the different components of the application, specifically within the essay, and where is their overlap, if any. I knew even very early on, talking to friends for instance, that MIT had a video component of the application, and so I actually knew I was going to need to do that and film that very far in advance and had to brainstorm ideas. So trying to just be proactive and get things done that is coming up, trying to the extent that you can share parts of applications. And then also, for me, the brainstorming is very much part of the planning, and I'm a planner by nature, so that was really important to me. Spending time listing out your ideas for prompts saved me to really be very focused in what was the story that I wanted to tell for each application, rather than going through a lot of drafts and writing and hoping it to come out in that type of freestyle form. So planning, and realistically just doing that brainstorming much earlier maybe than certain other people like to do it, yes, the month before, something like that.
Were you by yourself in this, or did you hire a professional consultant?
No. I thought about hiring the professional consultant, I definitely thought about it, and at the end of the day I just felt like I had so many people that had gone through the process prior to me even applying. Whether it was somebody like Julia, or some of my friends that are at Wharton, or some of my friends are at Kellogg, or even people that I knew had went to Booth before, trying to make use of people that had been through the admissions process before I was even applying and getting their feedback on what were things they wish they knew before they had applied. And then trying to bribe them with a beer or a dinner to read my essays and maybe look over my resume and ask some favors in that way. But I never formally hired an admissions consultant, no.
So I've always been a big Disney fan ever since I was little. I've been to several of the parks around the world, and my family always does a trip to one Disney theme park around the world every single year. My parents even go without me and without kids, and my parents are close to 70 and they go on their own, just my mother and my father. Kind of funny that they still do that even when I'm busy or my sister is busy. But that was something even that I had included in my video application to MIT. It was February of 2020 and I knew that I wanted to do something very interesting for the MIT application, and I had asked Julia prior what was the MIT video component, so I had an idea on time. And this is right before the pandemic hit, and I still remember going to Disney World in Florida towards the end of February before things started to, we all know. And I was able to film part of my admissions video in Disney World right before all of it was to close down, so that was kind of a fun thing. I liked that portion of the MIT application because it allowed you to be kind of creative and show a side of myself that maybe I wouldn't necessarily in a traditional application.
The application writing allows you to showcase your personality in a creative way, and it also really forces you to do that self-reflection on who you are as a person. Oftentimes we're so busy in our careers and getting the promotion, or just trying to honestly survive and get through the day, get through the week, get through the month, that we sometimes don't necessarily sit down and think what is maybe next, or what do we really want. The application process really forces you to do that, so I found the essay portion of the application to be actually enjoyable. It really helped me to go into business school very sure of myself, what are my values, and ultimately what do I really want to get out of business school. So it's really important to set that time, because if you come in and you don't know yourself, you aren't going to necessarily utilize your time to the best of your ability, because it goes by incredibly fast.
I completely agree. In very many ways it's a form of therapy, just being able to put down your thoughts onto theoretically paper and get them out there, and it helps you focus and see what are your values. For me it really helps solidify what are my values, and what do I stand for, and what am I ultimately going to bring to any of these institutions that I'm hoping to be the next stage in my career, in my life.
What was the Booth essay prompt, or were there multiple?
I don't honestly, candidly, I don't remember that well. At a certain point they kind of are blending together, so I don't really remember truthfully.
A lot of the themes of my essays were about kindness and how, in the professional world, people always think that you have to be tough and you have to be resilient and you have to be strong in order to get ahead. Oftentimes I think that that can be almost a conflict of interest, or that in order to get ahead you have to almost push people out of the way. I wrote in a lot of my essays the importance of kindness. I come from a banking background and I am going back into banking, a very different part, and for me kindness was something that was not necessarily a value or a virtue that was highly important, and I think it should be. When we think about our careers, we spend so much of our time with our colleagues or peers at work that we have to be kind to one another, because we're all going to face moments of adversity and we're all going to be challenged. It's just so important to be kind because you never really know what people are going through, and I wrote about that in one of my essays.
I had one boss who was really outstanding, and when I really needed somebody to pick me up, I was fortunate enough to have a manager who really stepped in and was really, really kind. That was an example that was set for me and something that I know I want to bring to my next position in banking. That was really what I focused on in a lot of my essays, just that virtue that had been shown in my prior position, something that I wanted to incorporate into Booth: just being a kind person. It sounds so easy, but yet sometimes it can be so challenging. That's realistically what I focused a lot on in my essays and what I tried to communicate and show.
In the essay process, and your whole application, my advice to anybody applying would be: be authentically you, whoever that is. Be true to yourself in the application. Don't try and fill a spot that you think that they want, or be somebody who you think they want you to be. The best essays, and the most personal ones, and the ones that receive the best attention and feedback are the ones that are just authentically that person, that you go, "Wow, this can only be Matt," or "This can only be Alex," or "This can only be Julia," that is so unique to them. Those are the best essays, and that's ultimately where people trip up in the whole process: they think they have to be something. You don't. Just be you.
I recruited for banking, and as I said, kindness is not necessarily something you think about when you think of the warm fuzziness of banking. But especially in the interviews for recruiting once you're here, it's the same lesson: show up and be authentically you for whatever you're recruiting for, whether it's consulting, whether it's VC, whether it's tech. Just be you. That was a lesson that ultimately came from the admissions process and something that you can still take with you as you recruit for whatever position you're trying to go for.
Who did you have read your essays to gut check whether they were authentically you?
I had one of my good friends from Wharton, who I went to U Chicago with, read some of my essays for Wharton and other schools, and then I also had a friend of mine from Kellogg, from high school, read some of my essays as well. A very wide variety of people at different schools, to try and get a diversity of opinions to see what people think. I tried to get my family to read them as well and just use them as a sounding board and say, "I think this sounds like me. Do you think this sounds like me? Can you tell this is authentically me?" Trying to get anybody in your life, whether it's family, a colleague, your peers at other schools, anybody you can get that actually knows you so well, those are the people that provide the best and most honest feedback. They'll tell you, "Oh, this is horrible," or "You need to be more concise," or "I would take this out." That's the only way you're going to get good, honest feedback, is by people that are willing to be honest with you.
The earlier the better. The planning process I always felt was key, even just trying to let your recommenders know very early in the process so they're not writing a recommendation on your behalf at the last minute. That was something I thought was super key, letting people know early, whether it be your peers that you're going to need to workshop your essays or look over your resume, or whether it's your recommenders, just giving them the prompts and helping guide them.
In the banking world, do you have to keep it a secret from the people on your team that you're applying?
That is kind of a controversial opinion. I tried to keep it a little bit more quiet and not let too many people know. My recommenders were all bosses of mine, so they were in the know, and they were also very supportive of me wanting to take that next step, because I think they knew that ultimately I was destined to maybe do something a little bit different and they saw this as just improving upon myself. It wasn't necessarily like a divorce, like once you're gone you leave the firm. I'm still very good friends with and talk very frequently to the people that recommended me to go to business school. So I didn't make it publicly known to everybody within the group that I was looking to make a change. I was more selective in who I let in on that information.
Who did you pick, how did you pick them, and how did you prep them to be the best recommenders they could be?
I had two recommenders for all the schools. One of them was our former group head of debt capital markets, and the reason I chose him was I did a lot of really good high-level, outstanding work, more strategic type work around the group that ultimately wasn't necessarily directly tied to my day-to-day job, but it was outside work that I specifically had done for him, so he could talk to one aspect of my professional life. And then I got my at-the-time current manager who could speak to things that I was doing on a day-to-day basis and things that were actively trying to better our group and better our team. So two different managers.
The way that I went about asking them was, once the prompts were officially out, I made a packet with all the questions that were relevant to them, that they needed to know for writing purposes. I put it all in a packet, and it gave the recommender limit or the word count that they needed to fill. I filled that out for them to give them a rough guide, and then ultimately putting this in a spreadsheet and creating a timeline for them as well: okay, I think this would be an appropriate time for you to probably have a first draft, I think this is probably when you should realistically be close to done, and then I would love for you to submit this two weeks before the deadline.
So I actively gave them all the questions that I could with the limits and gave them a very organized timeline on when they needed to have things done by, and I think that eliminated a lot of confusion for them and helped to streamline the process as much as possible, because these are people that are very senior and you are asking them a favor, asking them to spend time on a weekend away from their families to write something on your behalf. So the easier you can make it on them, the better it will go over.
Being able to explain the process matters too. One of my recommenders had an MBA, he went to Columbia Business School and he's American, but one of my other recommenders is Japanese, is not from the US and isn't really familiar with the whole process of applying to business school, and more so not necessarily familiar with writing recommendations. So I had to explain what's this for and what's the ultimate purpose. It was also a little bit of a challenge on the recommender front because my recommender or group head from Japan was in Tokyo at the time. He used to be in New York when I worked for him, and he had actually moved back to Tokyo, so trying to coordinate when Tokyo is 12 hours ahead of you was a little bit of a challenge. There were some logistical issues on trying to get things done and communicate along the way, but it definitely worked out. Some recommenders will need a little bit more explanation than others, and it just depends on if they're familiar with the process or not.
What did you guys get your recommenders as a thank you?
My one manager who was in New York, I think I did a card and a bottle of wine. And then I wrote a card or a really sincere email to my recommender in Japan, because that was also during COVID, and it's a little bit challenging to get things across the world at that time period.
I did Gourmet chocolates from Italy and wrote handwritten thank you notes for both of them. I'm trying to think if I also did a bottle of wine or something.
It doesn't need to be a lot, but just take a minute to really thank that person. Especially because they often will send you what they wrote, and you're like, holy crap, it takes a lot of work. And it's also worth setting them up and keeping them updated as you go through your journey and just thanking them again, because the recommendations can be a make or break.
Now you're in your second year of business school. Tell us about your experience so far, what you feel like you've gotten out of it, some of the highlights.
The good parts are definitely just meeting new and interesting people from all different walks of life, all different jobs, very diverse backgrounds who maybe I wouldn't necessarily have been exposed to. In a banking situation, it's somewhat of a self-selecting career, you really have to want to do it, but you just meet so many very interesting people from all different backgrounds at business school. I've met some of the best people in my life here in my first year at business school.
There is a tradition at Booth, a pre-orientation trip called Random Walk, and it is a way to really meet your class before orientation even begins. You go on a trip with 15 first years and four second-year leaders somewhere around the world for a week, and it's a way to really get to know your class much more intimately, because you're forced in that. You really learn about people when you go on a vacation with them. A lot of my really good friends have come from my Random Walk. I went to Ireland, and I wanted to pay it forward, so just this past year I actually was a second-year leader for a Random Walk and I led a trip to Bali. Bali opened up, and why not. We led a trip with about 14 first years and four leaders of us out in Southeast Asia, and it was a really good experience. It's very interesting now to be in your second year, because you have your old Random Walk, your friends from that, and then you have your new friends from the ones that you just made, and it's kind of introducing the two. It's a good tradition that Booth has.
What's been challenging? What are some of the less pleasant surprises of business school?
One of the challenging things is there's always something going on, and it's realistically just managing your time to the best of your ability and being selective on where you're spending your time and who you're spending your time with. Trying to spend time on a problem set when I'm also trying to manage 50 coffee chats this season with first year students that want to talk about banking, while still trying to go out and have a social life. The most challenging aspect is organizing your time, you have to be good at time management, because you can't do everything. I would love to go on every trip I possibly could, but time and money are the limiting factors there.
Then ultimately it's, when you do have that time, how are you spending it and using it effectively. I don't want to be the type of person that just sits in front of my TV watching Netflix all day. I would hope that I am trying to go work out or do something productive, definitely is not the case. This is the one time probably in most people's lives where their schedule is really dictated by themselves. When we go out into the corporate world again, it's dictated by our projects and our managers, people are pulling us in so many different directions. So what are you doing with your time now when you have the most control over your schedule, and how do you use it effectively?
You came to school to do this slight pivot in banking. Are you on track? Where are you now with your career and what you're thinking?
I successfully made the pivot. I am going back into banking into New York. Prior to business school I worked in debt capital markets, so it is a market facing role, it's more tied to interest rates, you have your six Bloomberg screens, you're getting in at seven. I wanted something that was maybe more inherently tied to the more modeling aspect of investment banking. I'm very excited and very grateful to be going back. I had an outstanding experience going and interning the summer there, and so I'm just very excited to meet all the people and, when I do start working, to get to work.
What stereotype about your school is true, and what stereotype isn't as true as you would have expected?
The stereotype that a lot of people probably have of Booth is that it can be a little bit of a nerdy place, maybe more so than some of our peer schools. At heart we are a bunch of nerds and we all really do enjoy learning. I'm already thinking about the courses that I want to take in the spring quarter and really planning that out. There's a professor here that actually won the prize for economics, Doug Diamond, and I'm hopefully going to try and take his course in the spring. So at heart I think Booth is a very intellectual place, and it's really engaging and very stimulating. Chicago has that saying, the life of the mind, and it's really true of all the schools at the University. So that is very true.
But what I would say is somewhat of a misconception is that maybe people think that Booth is too stuffy, or because it's an intellectual place that we don't have fun. No, we definitely do have fun. We definitely do go out, we definitely do take all the trips that all of our other peers take as well. So we're a good time. That was something that even I was concerned about, and I went to UChicago for undergraduate, but I would say that Booth students are very, very fun. We have a tradition called TNDC, Thursday Night Drinking Club, which is at one bar where all first and second year students at Booth congregate on a Thursday night, and so it can be a wild time.
Yes, I've got my internship, so I am definitely going to try to attend every TNDC.
Would you say you're an introvert or an extrovert?
I would say that at heart I am an introvert, but that I can play the part very well of an extrovert. I'm the type of person that I can be around people all day, but then when I come home I need my own me time and I need my time to decompress. So I can play the part well of both, but at heart I think I'm an introvert.
If you had to pick a new mascot for your school, what would it be?
Oh, that is a good one. How about the UChicago Booth Badgers? Beavers, I don't know. I can't, because MIT already has the beaver, Nature's Engineers. It has to be something with a B, though, because then it can be like the Booth. Right now I think we're just the same as UChicago undergrad, which is the Phoenix, which is cool. It's very Gothic architecture and I think it's still the same.
One interesting thing that I try to do with a lot of the new people that come on campus is I like to give them the tour of campus, because I went to UChicago for undergraduate and a lot of times the business school students don't necessarily leave the business school. There's such great architecture on campus, especially in the fall when it's beautiful weather. I like to lead a little tour around campus to show everybody around, because it's so interesting to see, whether it's the Gothic architecture or whether it's something that's modern. There's just so much about campus outside of the business school that we as business school students don't take advantage of.
I've got some trips coming up that hopefully materialize, just trying to lock down the details, so I'll be sure to share that when those actually happen.