What To Do When You Don’t Fit In

Written a couple weeks ago … July 25, I think. I couldn’t stop editing it.

If TL;DR … The Moral of the Story

Sometimes you don’t fit in and it’s not a bad thing but you should leave. Sometimes, you don’t fit in and it’s a good thing so you should leave.

Sometimes you don’t fit it in and that’s a good thing so you should stay. You don’t fit in, but if you resist taking the easy way out and you lift them up you’re a good fit.

If you want to read, BEGIN HERE

The other day, I sat in my boss’ office while he and a co-worker repeatedly told me, among other things, how unprofessional and uncooperative I was. Finally, my boss just stopped and, asking me to be honest, said, “Do you really think you’re a good fit here?”

His implication that I don’t fit in is certainly accurate and I’ve been going out of my mind trying to figure out the reason.

INSERT: Picture of me looking lovingly into a mirror

If you ask me, I’m ridiculously brilliant, obscenely talented, hard-working, charismatic, and not to mention really, really good-looking. All things being equal, I should be a total rock star. Unfortunately, my rock star status has been more Tony Martin than Ozzy Osbourne.

Looking back over the last four months and, more importantly, over the last 25 years, I was able to identify what I was doing when I succeeded and what I was doing when I failed. I’ve had more than my fair share of both. It all has to do with how I responded when I didn’t fit in.

Whether you’re late in your career, just starting a career, retired, or it will be years until your first job, I think and I hope these lessons will work for you.


This isn’t a new issue for me—when I was in 8th grade, my well-meaning Mom bought me How to Be Popular by “Dear” Abby Philips-Van Buren—. You might think, “But I’m in 8th grade, too—I don’t have any control over anything!” That’s incorrect. If what I’ve said resonates with you, I’m quite confident you’ll think of something—just don’t let anyone tell you it won’t work.

This riveting graph represents my career trajectory—the ups and downs—from 1990 until now, mid-2015. The line is starting to head upward again, but the star represents my current struggle with not fitting in.


In the interest of full disclosure, the lines weren’t quite that smooth. That first ten years would really look something like this.


Before you get too bored, I’d like to emphasize to young and old the difference between what I consider success and how much money I was making—just in case you stop reading before I get to my main point.


Notice how my income continued to rise even as my happiness, fulfillment, stimulation, pride in my work, growth, etc. rapidly plummeted to levels far below where I was before I even started my career. Also note that my income rose and fell rapidly and repeatedly while I gained momentum in the beginning. At one point, I was even losing money but I can’t emphasize enough how worth it those times were.

And, lastly, note that my salary took a dive when the red success line started trending upward with the optimism and potential of my new gig. Again, more than worth it.

So, how have I dealt with not fitting in? Not being a good fit? Usually, I left but this post is about two times that I stayed and how I handled it.


For the first twenty years, every time I didn’t fit in, every time a job no longer had anything to offer me, every time, every time we didn’t have the same values or standards, every time I hit a ceiling, I left. I went on to bigger and better things. Sometimes that was my decision and sometimes it wasn’t. I wrestle with whether or not I have regrets but, regardless, it was always time to leave and the trajectory always continued upward. Every time I didn’t fit, I left—except twice.


This part is really important. There are two times I stayed where I didn’t fit in and with drastically different results. I handled those two situations very, very differently. In the first case, the result was extremely positive. In the second, my career took a fatal nosedive.

As long as I mentioned money, it’s probably also beneficial to look at my marriage.


I got married about the same time my career was skyrocketing. Since we were both perfect, the marriage was perfect and we never fought or had any problems or fights which is why the line is so straight. Just in case you’re naïve or stupid enough to believe that line of bullshit, I’m joking. What isn’t a joke is that, based on my strategy at that second crossroads, my personal and professional life spiraled downward together. Eventually I lost my long-suffering wife as well as my miserable job. All the while, my income rose. My salary and hourly rate at its peak might not seem like much to some of you but it was a heck of a lot to me.

So, to the point—what did I do right and wrong that affected my career so severely in each case?

In each case, I did not fit in. It could be said I wasn’t a good fit. For the record, I consider those two different things. At present, I do not fit in with my team or department but it’s quite possible I am a good fit. You’ll see what I mean.

What I Did Wrong (the second time):

In 2009, a talented and brilliant “chef” (Instructional Designer) we’ll call Jack moved from Detroit, a city known around the world as beyond rich in culinary delights, to a town where the only “restaurant” was “McDonalds” (or, McEducation or Fast Food eLearning). To be clear, there is nothing wrong with McDonald’s. They only want to make junk food and for decades that business plan worked for them because their customers only want to buy junk food. The real McDonald’s boasted on their signs they’d sold “billions and billions” of junk food things. Much like my former employer, the real-life counterpart to this metaphorical McDonald’s, boasted they were the “world leader” in what they do. Giving customers what they want and growing rich doing it is fine. But if making and selling junk food isn’t your thing, you shouldn’t be there. You’re not going to change them—they’re achieving their goals, why would they change? You’ll only make yourself miserable. Or worse. Believe me, it can be much worse.

I couldn’t change them and trying just made the job go from totally boring to totally sucking. I decided it was time for me to be “responsible.” To just do my time and take my annual raises. The pay was good and the benefits were great. Who did I think I was anyway? I tried to take everyone’s advice and go with the flow. Go along, get along and so forth. Things got worse. My ideas, standards, and expectations got me labeled a troublemaker. People hired long after me got promoted above me. I was told in no uncertain terms a promotion for me just wasn’t going to happen.

I kept trying to have a better attitude and so on but when you clean stables for a living, no amount of positive thinking is going to change horse manure into a Nobel prize. Unless you can take pride in how high you can shovel a pile of horse manure, you need to move on. I didn’t move on and, eventually, my personal and professional life imploded in a black hole of, well, major suckage.

What I Did Right (the first time):

My beloved school Hillsdale College stopped taking the GI Bill while I was there because Congress voted to place conditions on the schools accepting it and Hillsdale was having none of that. I began my senior year at a brand new school among brand new people with whom I did not fit. Regarding this new student body in general, there were a few factors contributing to my misfit status but when it came to the student newspaper, it boiled down to the fact that the staff had been a team for four years. You could call it a clique but, honestly, that would be unfair–they had a legitimate history and a bond.

Despite years of experience as a student and professional writer including scholarships and internships, I could not an assignment (or, really, a column because, you know, I’m so awesome) I felt was worth writing. Again, there was nothing wrong with the leadership or management of the student paper–they’d earned the right to make decisions about content and style.

Readers consistently complained about the lack of sports coverage and I wanted to round out my portfolio and have experience covering sports for more opportunities to make money. When I asked if I could cover sports, I was told no, they had a sports editor and that was his job even if he was always too busy to write anything.

I decided to start a little “paper” called The Sports Page using the Mac and printer in the computer lab. I made appointments with coaches saying, “Hi, I’m the editor of The Sports Page …” (see what I did there?) I gathered schedules for all the teams, attended games, interviewed players, and took pictures.

While I assembled all of this in the lab, the editor of the “real” school paper stopped and stood behind me. He asked in a very perplexed sounding voice, “Is that … for us?”

“You’re not an asshole, Mark [Zuckerberg]. You’re just trying so hard to be.” – The Social Network

I said no and told him he already had a sports editor and it wasn’t me (I am not always a gentleman, as graceful, or as classy as I should be). He asked if they could use the content since, you know, I’d already written it and I did, in fact, work for the student paper.

I proposed that either I released The Sports Page with comprehensive coverage of all student athletics the same day as his next issue of the official school paper (with no sports coverage) which would really infuriate the already irritated student sports fans … or … I’m the new Sports Editor and I bring all my current material as well as the work ethic and passion that caused it.

As much of a prick as I was being at the moment, stealing a job or shaming them into making me Sports Editor wasn’t my original intent. My intent was to leave because I felt they were keeping or bringing me down. Instead, I stayed and learned something invaluable because, as a result, I lifted them up. Or, rather, I helped the paper lift itself up by being a good influence and making a significant contribution or maybe I unintentionally led by example and I’m just lucky they decided to follow. Regardless, it worked out.

I ended up starting the school’s chapter of the Society of Collegiate Journalists and was elected President by these people that I’d felt really hated me. Don’t fall into the dangerous trap of thinking these people with whom you don’t fit are the enemy.

That’s not always possible. At McLearning, it wasn’t possible. Sometimes you just have to leave. It doesn’t necessarily mean the place you left sucks or, especially if it wasn’t your decision to leave, that you suck.

The Moral of the Story

Sometimes you don’t fit in and it’s not a bad thing but you should leave. Sometimes, you don’t fit in and it’s a good thing so you should leave.

Sometimes you don’t fit it in and that’s a good thing so you should stay. You don’t fit in, but if you resist taking the easy way out and you lift them up you’re a good fit.


3 thoughts on “What To Do When You Don’t Fit In

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