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"Fitting out" instead of "fitting in"

Not to be the cranky person railing against social media, but isn't it crazy to see the comparison mindset that has been created in our lives through it? For all of the good we get from Instagram (keeping up with family and friends, tips for cooking and home decoration, travel ideas, hilarious videos, and links to those random products you never knew you needed but suddenly can't live without), we also have some very serious downsides of constant comparison. I sometimes wonder how many of the accounts I follow on Instagram are posting simply for the pleasure of showcasing what brings them joy and ensuring their friends and family can easily connect with them, or how many people are posting to simply appear in a way that is comparable to what they believe expectations of them are.

Of course, we don't just find this comparison game in social media. Let's circle back to one of my favorite topics in my blog posts: sports. As a fan of a mid-market baseball team, I am constantly aware of what other teams are spending to field a competitive team. I find myself yelling at the TV, "Well if only we had spent what other teams had spent, we wouldn't be playing so poorly!" However, don't think that comparisons are just something fans of sports teams do. We often see in sports that when one team makes a big trade or free agent signing, the executives of that team's rival will look to also make splashy moves and remain (or appear to remain) similarly competitive.

As much as we focus on it, maybe this comparison game doesn't always lead to the best outcomes for us. History is filled with success stories of going against the grain, zigging while others are zagging, and finding a new path yet to be discovered. We can take a look at Phil Knight's memoir, Shoe Dog, and see how he realized that the best way to grow a successful shoe company in the United States was to find suppliers in places no one else was going and to pitch his product in ways that finally resonated with shoe companies' key consumers. We can read the book (or watch the movie) about how the Oakland A's built a "moneyball" mentality when running their MLB franchise to compete in new and unique ways when the financial constraints of the team were holding them and others in the sport back. All it takes us is one quick Google search to find a decade-old article about how Apple has historically aimed over the years to be unique in the tech and software industry to find consistent paths of competitive advantage. There is no shortage of examples showing us how being different can lead to immeasurable success.

So, is all comparison bad? Of course not! In so many ways, comparison is healthy and incredibly helpful. Some examples of comparison providing value are when we share with our friends our restaurant recommendations, places to buy a bike, or seats we should look to buy for our next baseball game. Comparisons at work can also be helpful by allowing us to judge our own performance, identify paths to promotions based on the actions of others, and hopefully unlock powerful insights, like salary transparency.

So, at what point do comparisons become counterproductive, harmful, or debilitating? As leaders, how do we create awareness of the negative aspects of comparisons in our careers to ensure we are putting ourselves in the very best positions to feel enjoyment and fulfillment from our work? And then, how do we share this awareness with our team members to allow them to see their own worth, value, and aspirations as amazingly unique so that they are not simply comparing and following what others have done in their careers?


After graduation from Kellogg, I had the chance to take some time off, sit on a beach, nap, and read some books I had been wanting to get into. One of these was a book my brother passed along to me before I started my MBA program, Ahead of the Curve: Two Years at Harvard Business School, written by Philip Delves Broughton. After completing my MBA at a top business school and gathering my own thoughts and feelings about the process, I was interested to see someone else's perspective on navigating an experience with so many parallels.

A key takeaway from Broughton's book was that he felt a constant need to conform to the expectations of what someone in a top MBA program "should" be pursuing. There was an always-present reminder of the industries and companies his classmates were joining and how their paths often fit the exact mold of what MBAs are expected to aspire to. However, this is something that clearly confused Broughton during his time at HBS. The school brought in dozens of speakers and business executives that provided insights into their own journeys and how they had risen the ladder to success. But, in all of these talks, there was either a sense, or an outright acknowledgement, that rising to the ranks that were sought after by MBAs and other business leaders often led to a significantly decreased quality of life. Sure, there was more money than you could imagine, private jets, and prestige that is reserved for only the most well-known individuals in an industry, but these speakers missed out on some of the most important things in their lives, like time with family. Broughton would listen to these talks and wonder if these careers had really been worth it - if maybe their pursuit of attaining success by others' standards had impeded their abilities to actually achieve a balanced life that was fulfilling in the most important ways.

I constantly found myself wrestling with the same thoughts while at Kellogg. I was once in a class that had a guest speaker talk to us mainly about the ways he was able to strategically lead change in his career, but also more broadly about his own career journey. He mentioned taking a job in Europe simply because it was asked of him by his company, which forced his family to uproot their lives to follow him across the globe, while still not getting to spend enough time together. While this kind of career decision was not uncommon to hear from class speakers, it stuck with me because our guest mentioned that his son, a senior in high school, was forced to follow the family in the move, leaving behind friends, a girlfriend (now his wife), sports, and what is supposed to be one of the more memorable times in a young adult's life. Our guest mentioned that nearly two decades later, he and his son are still repairing their relationship because of that decision. All of us in class could so very clearly see the hurt in his eyes as he told us this. We could almost see him replaying a question in his mind that had likely surfaced hundreds of times since: Was it really worth it? And if not, what caused him to make that decision?


Something that makes a top MBA program a "top" program is the employment data of each graduating class. By placing graduates in jobs with brand-name employers that pay significantly more than peers, schools can showcase that their graduates have more favorable outcomes than other peer institutions. As a Kellogg graduate that will benefit from the doors Kellogg has opened for many years, I am not upset about this fact at all. What brings me pause, however, is the pressure this could place on students who are looking for their next job after graduation.

Take a look at Kellogg's Employment Statistics page. You can very quickly see a list of prestigious employers and the median base salary of graduates. In many ways, this is amazing! It is a testament to how Kellogg prepares its students to enter high-level positions at some of the most well-known organizations in the world and potentially help lead them some day. But how well are schools also showcasing the other opportunities for their graduates to find "successful" careers?

Graduates, of course, want their MBA experience to be "worth it". This often first means financially. Because most of us are taking out loans to attend these schools, we want to pursue jobs that will create a justifiable ROI. But in another sense, at a top program, you feel pressure around the type of job, the industry you are entering, or the role you are taking to also be "worth it". For all of the time you spent getting good grades in undergrad, studying for and taking the GMAT, and sacrificing time and grinding through schoolwork, cases, and group projects for two years, you also want to be able to tell the world that this experience was "worth it" and that you earned the job or salary that will make everyone nod their heads and say, "Yes, what you did going through that experience and attending that school now makes sense when I see where you ended up. Bravo!" But that seems kind of strange, right? You went through that experience. Shouldn't you be the one who decides what "worth it" is to you?

When we think about a successful career, we often think about the stuff that is easy to measure, like title and pay. What we have a difficult time measuring is how the salary you earn can be compared in a direct, monetary way to a more meaningful career, time with family, or the ability to pursue other passions alongside your job. I'm not saying we have a way to quantify that, but I am saying you don't see many articles written about the person who gets home every evening to have dinner with their family, pursues passions in and out of work, and has ample time to be a volunteer in the community. We also don't hear a lot of testimonials from the people that took jobs just to meet a certain expectation placed upon them, be it compensation, prestige, or industry, who quickly realized that they made an incorrect choice for their careers and suddenly felt stuck by an overwhelming workload, lack of daily inspiration, and lost time to advance their careers in more meaningful and fulfilling ways.

Because MBA students are the product of schools, not the consumer, it is understandable to see which industries, companies, and goals we should be striving for to find the "successful" career. What can become harmful for students, however, is to view what others are doing as what they should also be doing. Just because 33% of your class is going to one of the big consulting firms doesn't mean it's necessarily right for you. Maybe you'd really be happier pursuing work in the nonprofit sector and not working 80+ hour work weeks. Just because the median salary of graduates is at a certain amount does not mean you also should compare your journey and expectations to that and take a job that meets someone else's expectations of salary. Maybe you would be better off taking slightly less money now to be more aligned to your passions so that you can achieve the intrinsic motivation we are all so desperately searching for! However, this is a difficult mindset for us to snap out of when there are so many opportunities to compare ourselves to others, along with the weight of those outside expectations. As leaders, we can certainly struggle helping those that we lead to see this as well. So, how do we work through this dilemma? How do we find helpful opportunities to combat the inevitable comparison that will pop into our minds, and how do we change our mindsets and the mindsets of those around us to ensure we truly make the best decisions for our own needs and motivations?


As leaders, one of our major roles is to help individuals develop and advance on our teams and in their careers. However, if we don't take a proactive role in this by helping to uncover their interests, motivations, and goals, then we often leave career advancement up to simple comparisons of a team member pointing to someone else's path and thinking they should follow a similar progression in the exact amount of time that someone else did. The best-case scenario with this comparison is that maybe that does end up being exactly what our team member needs in their career, and maybe it can be achieved in the exact amount of time that it was achieved by someone else. However, more likely scenarios are 1) that isn't the best role and/or the optimal timing for this individual to see progression in their career, leading to disappointment and confusion, or 2) the opportunity does materialize in the way the team member expects, but they quickly realize this was not in line with their true interests or end goals; it just happened to be the closest comparison point that they could use for their expectations. We should be honored that our team members are all motivated enough to constantly be seeking out new ways to advance, and it is understandable that in some respects any advancement feels better than no advancement. However, what is right for one person may be completely wrong for another person, and this is difficult to always immediately come to terms with.

As leaders, we have a responsibility to model the behavior and actions we want to see from those around us. I would also venture to guess that we can all look back at various moments in our careers where we went out on a limb, took the unconventional path, and experienced opportunities and advancements that may not have been presented or earned had we stayed with the crowd or followed along with what we were "expected" to do or want for ourselves. Therefore, a key first step in aiding our team members is for us as leaders to realize the negative outcomes that can be produced from comparing career outcomes or giving in to the external expectations about how a career should play out and when. Only then can we pass this awareness on to our team members and more purposefully and meaningfully explore career paths that set them up for sustained success and happiness.

Not to declare that I have all of the best tips in this regard, nor that I am always perfect in creating the mindset I'd like to carry with me in this area, but I will tip my cap to the "power of three" rule that was so often mentioned in my MBA classes to outline some ways I have worked to remove myself from the pressures of external expectations and from comparing my path to others.

1. There are two groups of people in your life. This is one of the defining lessons from Harry Kraemer's Managerial Leadership class that I have carried with me in so many decisions in life. One of these groups, he told us, will receive news from us about a new job or a big life event and will be genuinely happy because we are happy or will gently probe about how they can assist with a situation where they feel like maybe we aren't truly happy. No matter what, this group just wants us to be safe, happy, and fulfilled. This group, if we are really lucky, will have at most about a dozen people in it. Everyone else falls into the second group of people. Maybe these individuals are genuinely happy for you with big life moments, but their attention will quickly turn back towards themselves and they won't have much interest or reason to spend energy wondering how you are doing. Even worse, you may find that people in this second group really aren't happy for you; these are people who maybe feel like you "took" an opportunity from them or maybe they now need to shift how they compare themselves to others because of some new bar you have set. So, when it comes down to how you choose to make decisions in your life and career, never make decisions for that second group. Their interest in you is either fleeting or they never wanted you to have success anyway. Make your decisions based on the first group of people in your life being able to sleep soundly knowing that you are exactly where you need to be.

2. Comparison is the death of happiness. This is such a powerful line from Broughton's book, which was presented to him and his classmate at graduation by their class speaker. Broughton zeroes in on this observation when he writes, "Measuring oneself against one's friends or peers could only lead to misery, because always, in some area of life, there will be someone doing better than you." This negative cycle of always needing a new comparison point could truly be a never-ending saga and could drag us away from the one area we should be focusing our attention on for meaningful improvement and happiness: ourselves.

3. It's about the distance traveled, not the heights reached. This is one of my favorite insights from John Amaechi. We all start from different positions of privilege in life, and it can be truly unfair to judge the end accomplishments of people who didn't begin at the same point in life on this scale. Therefore, instead of comparing end outcomes, or heights reached, we really need to be observing how far someone has come in their journey, or their distance traveled. With this mind, 1-to-1 comparisons to any given person can be tricky and will largely be unfair to one or both individuals involved. Compare your distance traveled to your own expectations, not the end goal of someone else.


One of my favorite podcasts introduced me to the regular use of the phrase "fitting out". They normally use this phrase when someone is actively choosing to not be in on the joke they are setting up, so they'll shout out, "Dan, please stop fitting out! We're fitting in over here!" I have started to use this phrase in my own conversations, but not just in the same scenario of joking around with friends. I've used it because I have been able to look back and reflect on all of the times I chose to fit out in my career and have been able to see how it advanced my distance traveled and opened exciting new opportunities for me to find joy in my career.

However, as leaders, how often do we encourage a healthy dose of fitting out instead of fitting in for our team members? Additionally, how often do we provide stories and examples to our team members to show them how fitting out in our career journeys led to more fulfilling advancements? If we are going to encourage our team members to follow the path that is best suited for their strengths, interests, and goals, then we need to be advocates and examples that comparing their path to others and focusing on fitting in will eventually begin to limit their distance traveled, as well as any heights they hope to achieve.


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