Don’t Should All Over Yourself

by Brett on January 24, 2011 · 282 comments

in A Man's Life, Personal Development

Do you ever get the feeling you’re living a life you never wanted? That you’re just doing what other people think you should do?

Maybe you’re stuck in a job you hate because you thought it was something you should do. You’re not really sure who told you that you should pursue that career, but you were certain you had to do it because it was well-respected and well-paid.

Perhaps you’re in college working on a business degree. You really wanted to become a barber and own your own shop, but you thought you should go to college instead because everyone says college is essential.

Or maybe you’ve accepted a request to work as a volunteer leader at a church or a civic organization. You knew your schedule was already packed with work and family, but you felt like you should accept. Now you’re burnt out and falling behind with the responsibilities of your job and your volunteer position, not to mention neglecting your family.

If you’ve ever felt like this, then you know exactly what it means to should all over yourself. It’s not fun and it sure ain’t pretty.

Should-ing Ourselves Silly

Should-ing on one’s self comes in two forms. First, it could mean doing what you think others expect you to do, doing the “right” thing despite what your hopes, your conscience, and your gut are telling you. This first type of should-ing is rooted in a sense of guilt or in a hope of gaining approval from others. The second form of should-ing on yourself involves re-living past mistakes over and over again, saying, “I should have done this” or “I should have done that.”

I know lots of men who struggle with the first kind of should-ing (me included! more on that in a bit) and today I’ll be focusing on this part of the equation, sharing my personal story in the hopes that others can learn from my mistakes.

We’re conditioned since grade school to follow a certain pattern in order to become a mature man. You know the drill. You’re probably living it right now:

Take out massive loans and go to college —> Get a 9-5 job with a decent salary and benefits —> Get married —> Have kids —> Take on a mortgage —> Work 30 years in something you’re not terribly passionate about —>Retire, buy jogging suit, play golf, and hold up lines at the post office —> Die.

This is what most American men think they’re expected to do and for the most part they follow along. Consequently, we end up living, as Thoreau said, “lives of quiet desperation.”

Boys Do as They Should, Men Do as They Choose

When you’re a boy, your life is pretty much laid out for you.  You have a bit of autonomy, but for the most part you simply do what you’re told to do.  And you know what? There’s something secure and comforting about that. Doing what you should do relieves you of the burden of making your own choices and being held accountable for those choices.

Being a man means taking control of your life and being responsible for yourself. A man does as he chooses, while a boy does as he should. However, some men never make this leap; they struggle with carving out their own path in life.

So they flounder. Because they’ve never actually figured out what they really want in life, they end up picking life goals they think they should have simply because everyone around them–/society/television/family/religion–tells them they should have those goals. In short, they should on themselves.

When you do things simply to please others or gain their approval, when you act purely from a sense of guilt, you give up a bit of your personal power. And you head down a path that invariably leads to feelings of  resentment, anger, and depression.

My Struggle with Should-ing on Myself

For most of my life I’ve been a people pleaser. As a boy, I loved getting the adulation of adults by following the rules and doing what I was “supposed” to do. I was the buzz-kill friend in high school who’d say, “Guys, maybe we shouldn’t be doing this,” when we were about to partake in some mostly harmless teenage hi-jinks. My friends, God bless them, put up with me, but they gave me an endearing nickname: Mama Brett.

To give you an idea how entrenched my thirst for approval was, here’s a journal entry from when I was 12 years old:

Today some friends brought some information about going paintballing. I thought it might be fun so I got some too.

My mom thought it was a bad idea to be going around shooting people. My dad thought so, too. He told me that when he trains for his job, he learns to shoot to protect people and himself. He also said shooting someone isn’t supposed to be fun, you only shoot someone if you have to.

I’m glad my parents aren’t letting me go. It shows me that they care about me and love me.

Face palm. My wife burst out laughing when she read this. What sort of 12 year old boy is happy and grateful that he can’t go paintballing?

I continued my quest for approval throughout high school. Growing up people always told me I’d be a good lawyer. Law seemed like a good career. It was prestigious, it paid really well (or so I naively thought), and I enjoyed Law and Order, so I figured why not? I’ll become a lawyer.

But ever since I was a wee lad, I’ve had a passion for teaching. I’ve always enjoyed helping people widen their personal and intellectual horizons. I love mentoring other people and helping them reach their potential.  And I love the opportunities that teaching provides for me to learn new things myself.  My senior year in high school I remember thinking that it would be really cool to be a high school history teacher and coach football. It felt right in my gut.

Then I went and “shoulded” all over myself.

Being a teacher wasn’t as “prestigious” and didn’t pay as well as being a lawyer. I couldn’t shake the feeling that what I should want was to fulfill the American Dream of being better off financially than my parents had been. I felt like I should want the “good life,” and to achieve it, I needed to be a high powered attorney, not some podunk high school teacher.

So I compromised. I told myself that I’d be an attorney for a decade or two, stockpile some cash, buy a house, retire, and then  start a second career as a high school American history teacher who coached offensive linemen in the fall.

I went to college and got my undergrad degree in Classics and Letters because all the counselors said it was a good degree to prepare you for law school. I really enjoyed my classes. I got to discuss philosophy, literature, and history all day.

During college I took a break from school to serve a two year mission for my church in Mexico. While I was there I rediscovered my passion for teaching. It seemed life was trying to nudge me back to becoming a teacher.

When I got back from Mexico, I went back to college and proposed to Kate. She knew about my goal of becoming an attorney, and she was mildly supportive of it.  One night we were having a talk about our future life together, and I told her of my dream of becoming a high school teacher and coaching football. I laid out my plan of practicing law for a few years, making lots of money, and then pursuing a teaching career.

Kate just looked at me blankly and asked: “Why are you putting off what you really want to do for twenty or thirty years?”

I hemmed and hawed. “Well, everyone has always said I’d be a good lawyer and I’d enjoy practicing law… It’s, um, prestigious… It would certainly make my parents proud…And I want to make enough money so we’re financially well off. I mean, I don’t want to buy fancy cars or have a giant house, I just don’t want to have to worry about money. I mean, shouldn’t a man want that for his family?”

Kate continued the blank stare. “Those are some really dumb reasons to pursue a career.”

That’s my wife. Always telling it like it is.

But she was right. I really had no interest in the law, nor did I know much about it as a career. I just made it a goal because I thought it was something I should do.

That night I started making a new career plan: to become a high school teacher. Kate and I were both excited and felt really good about it. Yeah, money would be tight, but with Kate teaching as well, we’d make it work. I started scheduling the classes I needed and researching the teaching certification requirements in Oklahoma.

And then it happened.

I shoulded a should load all over myself. The Should Monster paid me another visit:

“Brett, look at all your friends! They’re becoming doctors and lawyers and investment bankers. You should go for a prestigious, well paying job too!”

“Come on, Brett, you should want to take your family on nice vacations and buy them a nice house in a nice neighborhood.”

I caved. I told my wife that I was going to follow-through with my original goal of becoming an attorney. Teaching could wait. She was disappointed, but she supported my decision. I promised myself and her that if I was going to do this law thing, I would give it my all. I also promised I would try to avoid as much debt as possible to earn my JD.

For the next five years, I hustled my ass off. I graduated with my undergraduate degree a year early by taking summer school, doing classes over Christmas break, and overloading my schedule in the spring and fall semesters. In my spare time I prepped for the LSAT. I was spending close to 30 hours a week studying for that dumb test. It paid off, though. With the score I earned on the exam, combined with my GPA, I was able to get a near full ride scholarship to law school.

At the beginning of law school, I quickly learned the “shoulds” of young law students: graduate in the top 10% of your class, get on law review, and land a big firm summer clerkship that paid mega bucks. Being the consummate shoud-er that I am, I made those shoulds my goals.

And I achieved them. First semester of law school, I was first in my class. My second year of law school I earned a spot on the law review. The summer between my second and third years, I landed high paying summer positions at two of the most prestigious firms in town.

Despite achieving these goals, I was miserable. But I kept on trucking.

My internships during the summer were my first real experience with the practice of law. And I quickly discovered law wasn’t for me. 60-70 hour work weeks. Billable hours. Work that didn’t interest me.  However, I feigned excitement so I could convince the hiring partners to bring me on full-time because I thought I should want to work at a big firm. I explored government work and small law thinking maybe it was just the big law firm atmosphere I didn’t enjoy. But I got the same results. It was official: I had no interest in the law. Sure, I was good at law, but it just bored me to death.

My third year of law school I decided that I was going to do everything I could not to practice law. I would try to find another career that would put my law degree to use, pay off my debt, and cut my losses. It was then that I had a moment of agnorasis. I realized I had spent the past three years of my life working for something I didn’t really want simply because I thought “they” (whoever they are) said I should want it.

Let me tell you–it’s a sucky feeling to realize your unhappiness stems from the fact that you tried to conform your life to someone else’s expectations rather than following your own inner compass. I was angry at myself for not having the spine to go after what I really wanted. I felt guilty for having made Kate a law school widow for three years without a definitive purpose.

During law school, I started blogging as a creative and mental release. What was interesting was that my articles naturally gravitated towards content geared towards helping people. Blogging provided me a chance to learn new things and then share what I learned with others. Basically, blogging let me be a teacher in a less traditional mold.

My first blog was called The Frugal Law Student. I started it in 2006 and had some mild success with it. Then in 2008, my second year of law school, I started The Art of Manliness. (If you want to see why I started the site, read the about page). In just a few short months it was receiving large amounts of traffic, getting great publicity, and growing a small, but passionate community. I was spending around 20 hours a week on The Art of Manliness back then, with even more hours spent on writing our first book. This was on top of law classes, law review, and a part-time job. But I didn’t care. I loved working on the site.

By the time I graduated in 2009, The Art of Manliness was enough of a success that doing it full-time was a viable option. I was now putting at least 40 hours a week into the blog and so was Kate, who I had brought on to help me share a work load that had become far too big for one person. We would be barely scraping by, but would have enough money for a roof over our heads and food in the fridge. And most importantly, I’d be working in my vocation. I’d be happy with my work. So I decided to throw myself into building up AoM.

And then I dropped a big should on myself. Enter stage left–the Should Monster:

“Brett, you really should put that law degree to use. It’d be a waste of three years if you didn’t.”

“You should take the bar exam even though you don’t want to practice. You know. Just in case.”

“You should get a “real” job. You can’t be a blogger for a living. That’s just silly.”

“Health insurance! You’re going to start a family soon. You should get a job that has good health insurance!”

And once again, I caved.

In June 2009 I started applying for a position with a legal publishing company that I worked for as a law student. The position was actually a really sweet gig. It paid an awesome salary, it involved teaching, and my hours were flexible. Still, I knew it would be tricky. Complicating things was the fact that Kate was pregnant. Could we both work on the blog and take care of the baby while I worked a second job? But I convinced myself that I could do it all. I  justified the choice by telling myself that blogging wasn’t a “real job” and that I needed a back-up plan…but really I was once again just doing what I thought I should be doing.

I got turned down every time I applied for the corporate gig for about a year, and in the meantime I kept plugging away at AoM. We even published a book during that time. Our income from the site was starting to provide us a comfortable living, but it still felt like a hobby despite the fact I was working on it full-time, seven days a week. So I kept applying for that legal publishing position.

I finally landed a job here in Tulsa. I was pumped. I had achieved another goal I had set for myself. I had a “real” job. This the spring of 2010. By this time, AoM was growing faster than ever and keeping me increasingly busy. New opportunities were showing up. We got a second book deal. I was getting some speaking gigs. Everything was awesome.

But then Gus arrived. Late-night feedings, diaper changes, and comforting a crying newborn was a lot more work than I thought it was going to be. I kept soldiering on, but I was hitting a wall–physically, mentally, and emotionally. I was working 40 hours a week at my day job and putting in another 40 with the Art of Manliness. There was no way I could keep this up for very much longer. After five years of putting in 70-80 hour work weeks my body and mind had had enough.

Things came to a head over the winter break. I realized that I couldn’t do both things well. I had to decide: keep going with the respectable, well-paying corporate gig or take a risk with something that I was really passionate about, doing what I actually wanted to do. It was a choice between should-ing and choosing.

After 28 years of doing what I thought I should do, I finally decided to follow my heart and my inner compass.

But it was still a tough choice. I don’t like to quit things because a man shouldn’t quit things he starts. I also felt guilty for leaving my boss after only 7 months on the job. The man is an amazing manager, and I learned a lot while working for him, so leaving was hard. It took me three weeks to work up the nerve to tell him the news. I kept vacillating between should-ing and choosing. But I stuck with my choice. My boss was completely magnanimous. He congratulated me and wished me well and was genuinely excited for me.

My last day with my corporate job was this past week. I’m now devoting myself 100% to The Art of Manliness, and I’ve never been happier. It feels good to do what you want and not just what you think you should.

Stop Should-ing on Yourself

Learning to stop doing things out of guilt or the need for approval was a long, hard process for me. And it’s still ongoing. But here are a few things I’ve learned along the way:

Find out what you want really want. If you’ve never sat down to figure out what you want out of life, do it today. If you’re a young man just embarking on life’s journey, do some soul searching to see if you’re in the right career or major. Ask yourself  “Am I doing this because I want to or am I doing this because I think I should?”

If you’re a man who’s years into his career or life choices, and you feel like you’re not living the life you want, figure out what you’d like your life to be and start hatching plans to make it a reality. It might be hard to navigate family obligations and your dreams, but it’s possible.

Just say no. Start saying “no” to requests of your time and energy. I think most men who should on themselves automatically say yes to most requests because they want approval from everyone around them or they operate out of guilt. Don’t fall into that trap. You don’t have to be a jerk when you say no. Just politely and firmly say, “No thanks!” and walk away.

Replace “I should” with “I choose.” You’re a man. A man does what he chooses, a boy does what he should. Instead of saying “I should,” say “I choose.” “I choose to go to college.” “I choose not to volunteer this weekend at the company BBQ.” It’s amazing how much more powerful and in control of your life you’ll feel when you start choosing instead of should-ing.

Balancing Responsibility with Your Personal Autonomy

Now let me be clear. I’m not suggesting you become a selfish jagweed in your quest to quit should-ing on yourself. Sometimes doing what you should means doing the honorable thing. We all have duties and responsibilities we have to fulfill even when we don’t feel like it. It will take some judgment and wisdom on your part to balance doing what you should and doing what you choose.

For example, you really should be faithful to your wife. That’s a no brainer. But should you stay at a corporate job you hate out of guilt that they need you even though you have a better opportunity somewhere else? A corporation that wouldn’t bat an eye before downsizing you? Probably not.

The difference between mere “shoulds” and real responsibilities is sometimes easy to discern and sometimes very difficult.  It’s something we get better at as we mature, consult with trusted friends and family, and learn to become attuned and responsive to our own inner compass.

Alright, what do you guys think? Have you had a problem with should-ing on yourself? Any suggestions for men who do?

{ 282 comments… read them below or add one }

201 Graham Wilson January 30, 2011 at 10:57 pm

You know something? Without changing a word, this post COULD be turned into a book and become a best seller. Go for it!

Thank you, Graham.

202 JR January 31, 2011 at 1:54 am


Thank you for this post; I needed it.

203 Kris January 31, 2011 at 5:16 am


I would add, “stop should have” yourself, too.

Occassionally, we would tell ourselves, “I should have done…” this or that. I say, stop that as well. Your choice is made – act on it, re-consider the situation, re-adjsut to the circumstances, and continue.

Sometimes we wonder should I do this, because I should or should I do that because I want to. Then we act. Then we face the circumstances. And there must be no “I should have done otherwise” or “I could have done this other thing instead.” You did it. Period. Don’t should have or could have yourself either. Live with it, improve, perfect, do it better next time, but don’t blame yourself.

Take responsiblity.

204 Mango January 31, 2011 at 12:12 pm

Sub’d. Man this was good <3

205 Lindsey February 1, 2011 at 10:17 am

OUTSTANDING post and truly inspiring! Thank you so much for sharing Brett!

206 Kelly February 1, 2011 at 2:33 pm

I agree with Graham – turn this into a book! As a lawyer turned digital strategist for blogs and all things social media (after much soul-searching), I can totally relate this post. Very inspiring, indeed.

207 Bill February 1, 2011 at 3:15 pm

It’s good to read this post. I went through a similar life change recently. For many year I was frustrated that I was never able to serve in the military. When I was young I had acute asthma and would never be able to make it through basic training. By the time I got in the best physical shape of my life, and could endure the physical aspects of military life, I had a child and would not leave him behind. It took some time and soul searching to come up with a plan B out of what time I had left. I started school at 39 years old to become a machinist with a goal of custom rifle building. two years later and I’ve got two classes to finish before graduation and I’m still working on the dream.
I’ve got some secondary goals in mind as well. I will start this summer learning German. After that, who knows. I just had to realize that I still had time left to do things I wanted to.

208 Chandler February 1, 2011 at 7:43 pm

Thanks Bret, I’ve been really struggling with this for a while, especially the last few days.

209 Kenneth Jones February 1, 2011 at 11:47 pm

Great article! I’m now teaching English as a foreign language in China, because it’s what I chose to do. Choose what tugs at your heartstrings — it’ll work out.

210 Z February 2, 2011 at 2:34 pm

Wonderful post, and I whole heartedly agree. I’m not a good (or cohesive) writer, but here’s an attempt at my story:

I loved building and designing things since I was a kid, and when I got into college, I decided to follow that and studied both Architecture and Engineering. As soon as I graduated, I was offered a well-paying job with a general contracting company, which I accepted. I worked there for a few years, and it was nothing like what I expected. Long hours of paperwork, politics, unnecessary bureaucracy. The fact that the actual building and problem solving only accounted for 5% of my time there really put me off to the job and eventually made me very depressed.

So at the end of 2009, two years of seeing “the real world,” I left. I started doing some small freelance work here and there to make ends meet until I found something more suitable. I interviewed at multiple companies, with no one offering what I wanted. So I decided that if no one can give me what I want, I’m gonna give it to myself.

I started advertising my services, and working on small jobs with clients, assisting in design and problem solving. In my remaining free time, I started taking courses and got educated and certified in some niche areas. It was tough, as I do not have a professional state license, but I trooped on with what I knew and did what I could. The first few months were hard, but I kept moving forward and eventually found some good contacts.

Now more recently, I get calls from clients for more work than I can physically do, giving me the ability to pick and choose only what i want to do. With my new schedule, I work 4 days a week, attend sabbath, take out my fiancee anywhere she wants, and still have time left over to enjoy my life and continue learning. I’m working, but I’m doing what I want, I’m stress free and I’m making enough money so keep saving and move forward. I did what I wanted, and its been wonderful. When people ask me, I recommend the same thing, move forward with what you want, and with hard work and persistence, you’ll get to exactly where you need to be. It’s similar to the article on this site about “no”, you’ll get a lot of them, but what one “yes” will eventually pay off.

211 zman February 2, 2011 at 11:51 pm

This is great. I actually made what most people seemed to consider a risky and sort of free-minded decision to get a master’s degree in painting (ultra prestigious school of course). Did I need the degree? Do I need the mountain of debt? Who was I trying to impress?

Should have done what I wanted and not worried about pleasing/impressing family, friends, the world. I’m trying to do it now but the MFA almost killed me, was totally beside the point and has me buried in debt. I have the diploma. I don’t know where it is (would like to wipe my rear with it and send it back). My kids are proud that their dad went to this school and wear shirts bearing its logo. When the time is right, I’m going to make sure they know how meaningless this sort of thing is and encourage them to do what they want – no need to please or impress me.

212 zman February 4, 2011 at 11:04 am

In spite of the some of what I wrote, I have to say I completely agree with Kris’s comment.

213 BillM February 4, 2011 at 11:24 am

Just be careful to realize it when what you “choose” to do is not working out. The you “should” “choose” to do something else. No point flogging a dead horse.

I have made many choices during my life: musician, calligrapher, student, librarian, journalist. and each time I changed directions it was because I had reached the limit of either my interest, or my abilities… and knew it was time to move on. As the singer said, “You got to know when to hold them, know when to fold them, Know when to walk away, know when to run.”

214 Andrew February 4, 2011 at 2:52 pm

You really laid it all out here Brett, exposing much of yourself and your life, admitting to failures and miss-steps and illustrating how not being prefect helped you to grow into the sort of person that embracing living for yourself (with integrity of course) and not for others. Probably the best piece you have written for this blog, once again showing that being open and unashamed of short comings is damn manly…

Well done Sir, from one ‘Man in the Area’ to another…

215 Niki Turner February 4, 2011 at 3:05 pm

Wonderful post, thank you! I linked to it in my post today on my blog.

216 MerrillMonty February 5, 2011 at 11:33 am

This is a wonderful post, excellent for my position in life of just starting out as a young married man in his first “real job.”

However, while “choosing” what one wants to do is highly essential for self health, it sometimes can be a selfish action. Great article, but it makes me really want to produce careful decisions that the “choosing” I do is for the right motives and not selfish ones.

Keep up the GREAT work Brett, and CONGRATS on going AofM full time!

217 CSULB James February 6, 2011 at 4:03 pm

Thank you for writing this article. Hearing your story inspired me to break free from everyone’s wishes and begin to live my own life and make my own decisions. I had a problem of “should-ing” myself especially during high school. I would always be doing people favors in high school when I really didn’t want to do stuff they told me to but I couldn’t say no. Everyone said I was a nice person but the things I did for my friends didn’t make me happy but for them only. In my mind I was thinking I should of said “no” but I got through the phase what if I do say no what will people think of me. Every day I can guess everyone has to make a decision that can effect someone’s life or themselves. Individuals begin to wonder if their decisions were for the best or clearly created a negative impact and we begin the regretting stage. By eliminating the “should of” individuals will start building confidence and will never regret anything that they do because they know they have made the right choice. Once we start regretting our actions we become flawed and confused of what we really want because it’s a conflict between the mind of society and your own thoughts.

218 scott February 8, 2011 at 12:01 pm

While the realization that you can choose what to do with yourself is crucial, the devil (as always) is in the details. It’s one thing to make a course correction when you’re young; it’s an entirely different proposition when you’re middle-aged, and the execution of a change can become extremely complex, if not impossible. I speak from experience.

219 Rhino February 8, 2011 at 5:36 pm

I just found a book this morning about this topic. The Art of Non-Conformity.

I live this should-less life as much as I can, but damn it can be difficult!

220 CA Brown February 8, 2011 at 7:44 pm

Should-ing has been the story of my life. Thank you for an excellent post Brett. I have really been struggling with this for the last few years.

221 Steve February 9, 2011 at 5:12 pm

Wow dude! As a fellow law student … this resonates so deeply.

222 Mr. Wheat February 11, 2011 at 2:52 am

I’m pushing 40 and come to the conclusion that I hate what I do (IT). This article was written at the right time as I’m looking to go into doing something I wanted to do years ago but didn’t because I should all over my self. “Bird in hand.” reasoning. Thank you Brett.

223 Nicholas February 11, 2011 at 2:07 pm

Brett, congratulations on making the big step!

I’m exactly in the same predicament. I am recently married, just bought a house, and have an 8-week old daughter. I have a nice job at an insurance company that pays the bills. However, this week we had interviews for me to move from my temp position to a permanent one. I felt so out of place having to grovel before my boss to get a position I only slightly wanted.

At the same time, I am toying with starting a business I know would be successful. It’s very time sensitive, and I know I have to act on it now if it’s going to work. At the same time, I feel my family obligations mean I SHOULD keep my job. Tough dilemma.

I resolve to take the time to pursue my business interest. There is no reason for me to hold back, and this post confirms it.

224 Asher Rieck February 12, 2011 at 11:54 am

Brett, I feel that I have to tell you: Write another book. What you’ve written here is truly inspiring. If you went into detail about this message and your personal story, you could change even more lives than you already have. I would be first in line to buy your autobiography/self-help book. Thank you for all you’ve done.

225 Mac February 15, 2011 at 11:02 am

I am 58, and have practiced dentistry for 30 years. Maybe it’s time to do something I would really enjoy! I’ve done what I ‘should have done’.
love the website.

226 D.J. February 16, 2011 at 8:15 pm

Brett (and Kate),

I have no idea if you’re still reading comments on this post, but I just wanted to thank you for inspiring me to get off my duff and do something with my life. From one bored lawyer to another, I have to say, I’ve “should” on myself way too often. I’m trying to change this, slowly but surely, and your story helped give me the confidence to move forward with some plans that have been on the back burner far too long.

Also, great work on the site. Whenever I stop by The Art of Manliness, I know I can expect thoughtful, entertaining, and (most of all) useful articles. Keep up the great work!

227 OSolano February 20, 2011 at 1:41 pm


This was definitely an inspiring post for me.

I’ve actually started putting your advice to action and am really taking the necessary steps to carve the type of future I want.

Keep up the great work! You are definitely teaching, helping and making a difference!

228 Keaton February 22, 2011 at 10:59 pm

Dear Brett,

Im currently a student at Ohio State University. As it was as of 5 minutes ago I was a Finance student trying to get a math minor, and take my LSAT to law school. Hah I always wanted to be a math teacher even though my friends, and family think that I would be selling myself short. I was gunna go to law school and work for a few years until i started teaching. Thanks to you I’m going to become a math teacher. When I read this I so suprised at how close our situations were.

I appreciate this so much.

229 Caroline Johnson November 30, 2012 at 8:28 am

I’m actually a girl, but my boyfriend showed me this article and it is SO appropriate for both men and women. He and I are both mega “should-ers”, and this article really opened both of our eyes to the way we’re currently living our lives and the way we want to be living our lives. Thank you so much, and good luck with everything!

230 Josh December 5, 2012 at 11:39 am


Thank you for this post. I feel like I can closely relate. This is really hitting me hard. I have spent the past ten years gearing my life towards medical school and it has always felt like it is something I “should” do. I was a smart kid who was really good at science as well as being the oldest in a family of six meant that I was good at taking care of people…med school was just something everyone thought I should do. It has the prestige, salary, and personal satisfaction but I have been having serious doubts if it is something I really want to do with my life.

I finished my undergraduate degree, got married, and have been trying to get an MCAT score that will get me in.
I feel like I have run out of fuel in my “should” tank and I just can’t force myself to take the final steps that I need to take to make it happen.

It is so scary to try to think about what I want to do with my life other than this because I honestly don’t know. All of my life has been dedicated to what I should do.

231 letgoletlive December 19, 2012 at 9:32 am

Hi Brett,

Great article. It was just what I needed to hear today. I made a choice yesterday that was the right thing to do and it made me feel great. I knew it wasn’t what I should do. I spoke with others who said I shouldn’t have. I had to make a choice or just should. There was a time when my vocabulary consisted of shoulds, woulds and coulds. It was pointed out to me and I began to take notice of how frequently I said these words. Now, when I am about to say them I think to myself, “Shoulda, woulda, coulda. I shoulded all over myself today.” You might have to say it out loud to get it.

232 James McKnight January 8, 2013 at 9:43 am

Thank you. This has eased my mind greatly. I am currently denying a job and scholarship for a Master’s in Counseling that my family thinks I “should” take; however, I am going to choose what I want to do and apply for mission trips with an organization or to go out and search and find myself, even though it is risky. Today I am a man.

233 Father Muskrat January 8, 2013 at 1:51 pm

Great read!

234 RQ January 24, 2013 at 10:05 am

Wow, after writing a personal journal entry asking myself what I’m doing with my life, this post couldn’t have come at a better time. Thanks so much for sharing!

235 jimmy January 24, 2013 at 11:31 am

Great piece and for those who want to delve deeper check out Daniel Levinson’s ‘Season’s of a man’s life’. Among other things it contains a warning as to what can happen at mid-life when you’ve been driven by the ‘should monster’. For me this is about value systems. Either you live by your own or someone else’s. Each has it’s own consequences.

236 GENE February 13, 2013 at 7:36 am

Thank you for the great article. We all at some time or other compromise ourselves getting lost in the toll of should and not reaping the rewards of the could. Each day the price of should mounts up if not checked into what could of been in a more self empowered life of gratitude without servitude to what does not gratify your state of self esteem of being.

237 Daniel February 17, 2013 at 4:43 am

Great article, I see so many men my age (mid twenties) should themselves into terrible jobs and even worse relationships (myself included). It wasn’t until I stopped doing what I thought others wanted me to do that I started being happy with my adult life. You might want to add a prequel article about teaching your son/daughter to learn choose over should at a younger age to help facilitate their transition to adulthood.

238 Wayne February 21, 2013 at 9:12 am


Thanks so much for the inspiration. I reached a point of my life where I struggle with the exact situation and your blog allowed me to identify with my feelings. Now I can formulate a plan for myself to “choose” my course in life. Many Many Thanks

239 Daniel Rojas February 28, 2013 at 9:07 pm

Hey Brett, you were a superb student even if you did not liked what you study.

Congratulations for the posts and the website.

240 Matt Whitney May 17, 2013 at 9:18 pm

Thanks for everything you do. Your articles always inspire me and this one is no different. Hearing a wise man telling me it’s okay to say no and not do what I “Should” all the time is freeing.

241 Daren June 3, 2013 at 6:50 am

This was perfect and came at a f***ing PERFECT time.

242 Dillion June 30, 2013 at 11:01 am

Thank you for the article. I had a similar experience in my “career of choice”. From a young age I showed a lot of interest (and skill) in accounting. When it came time to start college I did what any accountant “should” I went for my CPA. …It didn’t work out, and while I LOVED bookkeeping I gave up on the career entirely due to my disappointment in myself. I have a good career now, which I am happy with, and the skills I’ve learned from bookkeeping help out quite a bit, but those “shoulds” are more problematic than helpful!

243 Geary July 30, 2013 at 10:28 am

Guess I “should” comment… ;)

Excellent article and makes me think about the things going on in my life.

A small group of close friends and I have, in the past, been invited to another friends house to party on a couple of occasions and others in our group always want to skip out early and head to the dance club. I don’t feel right about it, but was thinking at the time, I “should” follow my close friends; even though our company and attendence was important to the other. A party is coming up soon and can see the same situation developing.

This time I will “CHOOSE” :)


244 Charles August 14, 2013 at 12:18 am

Wow…just wow. I read this after a bout of insomnia and this post really hit home. It’s helped give me some perspective. Thank you for a great site! You do amazing work and overall, this site has to be one of the best things to happen to the internet!

245 bert September 18, 2013 at 4:25 pm

I feel just like it: having done what I felt I should have done and not what I have wanted to. Thanks for your advice. Great post!

246 Don September 28, 2013 at 7:59 pm

I have lived too many days shoulding and now it is very hard stop. I have a hard time planning. Life is very scary right now and now will say I will plan better instead of I should have planned better.

247 Juan October 9, 2013 at 2:08 pm

Thank you for this post. Don’t know why, but I’ve landed on it and read it in a moment of my life where I was needing something like this.

Thanks. Juan

248 Madeline October 24, 2013 at 1:51 pm

EXACTLY what I needed to hear today. Thank you. No, I’m not a man-but my husband recommended I read this-because he also knew I needed to hear it. Inspirational.

249 Edward December 5, 2013 at 9:57 am

Thanks great advice, i want more on this topic, thanks for making life for men better.

250 Edwardo Ar December 8, 2013 at 1:51 am

Omg, love!!! The interaction among the two is astounding. So are your pics

251 Dave G January 7, 2014 at 1:15 pm

Brett – thanks for making the decision to teach. I first learned of this site by following a link for your pocket knife, and have been immersed in your teaching the past few months – though I have yet to buy that knife! Thanks for helping me on my journey, and for giving a modern forum for some classical life lessons and considerations. Way to man up!

252 Kane January 25, 2014 at 6:26 pm

I, too, have been a professional should-er over the past 15 years. A recent shut-down has given me a chance for a course correction. Now if only I could find my wanna, so I don’t have to take another shouldy job.

253 Zack January 26, 2014 at 12:45 pm

Honestly, I may end up burying myself in a lifetime of should-ing. It dictates me every day, after all, as I say it, I should stay in my job, despite being miserable, because I need to pay rent and won’t be able to find work anywhere else.

It’s hard and it’ll keep being hard, but this post was a much needed, encouraging nudge.

Little by little, I suppose.

254 Gary January 27, 2014 at 1:37 pm

Great article….I’m way older now and retired…spent almost all my life ‘should-ing”…not sure what to do at this stage of my life…but so encouraging to read this wonderful article and so enjoy your blog….wishing you continued success …thanks again

255 Bo January 27, 2014 at 1:57 pm

Its as if you live in my head and know what words of wisdom I need and at what time… you are pretty much batting 100% with me… thanks Brett

256 Ariah January 27, 2014 at 2:20 pm

This is EXACTLY what I needed to read today. Thank you! :)

257 Reggie January 27, 2014 at 2:33 pm

I knew there was a reason I love this website! As a 38 year old father of 2, who is currently “existing” at a job that “pays the bills”, I long to do something of my choosing. I was never particularly self-motivated and have spent most of my life getting by but I am growing tired of that existence. It is hard to teach an aging dog new tricks but I am working on it! Thanks for sharing your story. – Your brother in the struggle, Reggie

258 Daniel January 27, 2014 at 2:57 pm

Awesome Blog- just what i needed to read this week. How do you overcome the 2nd “shoulding” of dwelling on the past of “I should have done it this way”…etc… ?

259 Matthew Kuehlhorn January 27, 2014 at 3:03 pm

Thanks for this. I have be shoulding all over myself in the past and to this day.

Shoulding on myself brought me into Chapter 7 bankruptcy.

It also brought beautiful children into my life — whom I could not imagine life without.

Shoulding brings pain and pleasure then…it only sucks when we think we should listen to the shoulds.

It breaks us from our flow.

260 G January 27, 2014 at 3:30 pm

Great article, great timing..


261 Colonel Cardigan-Fitz-Badly January 27, 2014 at 3:37 pm


ie.”I really could lose weight and get fit”
“I really could lead my chaps better”
“i really could be kinder to my wife/girlfriend/ alpaca shepherdess.

Every chap need Cchoices because they’re opportunities.

262 Isaac S. January 27, 2014 at 4:04 pm

I think you should be careful in encouraging people to “pursue their dreams.” I know lots of people who are always working on some new “dream” and somehow end up being broke and living in mom’s basement at 35. While you certainly shouldn’t do something you hate, I think real men need to be comfortable with the idea of a “good enough” job. I may not be saving the world as a manager in corporate IT, but I pay my bills, I feed my kids, and I don’t have to worry about selling my organs if the car breaks down. While sometimes I wish I had done something I was a little more passionate about, I don’t regret having a solid career that enables my kids to live in a nice neighborhood and go to good schools. You were fortunate that AoM worked out so well; many people aren’t as lucky to find a 1-in-a-million niche and manage to find fulfillment going to work at a big company just like everyone else.

263 Alex January 27, 2014 at 4:19 pm

This post hit me right in the chest…..I needed this man. Thank you so much. And Good Luck!

264 Aaron January 27, 2014 at 4:23 pm

Thanks for this. I have recently been thinking about going back to school. After reading this I realized that I don’t want to but rather I feel like I should. Not sure what to do now… think I need to figure out what I really want in life.

265 Sebas January 27, 2014 at 4:53 pm

I read this post right in the perfect moment. Thanks.

266 Jorge January 27, 2014 at 5:02 pm

Awesome article man!
Right now i’m facing a hard decision. Should i stay with her, or not? My family love her, she’s cute, she’s a nice girl. But i don’t feel well with our relationship anymore. I feel it’s gone. Now i’m looking at my female co-workers and start comparing them. And i know that’s wrong.
She’d be a wonderful wife, no doubt. But i’m not sure if she’s the one for me. Should i choose her? That’s my inner struggle right now. I have to choose.

267 allhaileris January 27, 2014 at 6:57 pm

I think this is backwards. Our nation is full of men doing as they choose instead of doing what they should. 40% of children are now born to single moms in single parent households. In the African American community, that jumps to 70%. I think we have far too much focus on self gratification today, and expect government to pick up the slack. Any selfish twat can put himself first and do as he “chooses”. A man honors his commitments and does what he should. Doing as one “chooses” is a luxury enjoyed by college age children.

268 Mike January 27, 2014 at 7:05 pm

Perfect timing. I just happen to have an interview for one of those big firm “should” jobs that I’m not overly excited about this week. I wonder how it will play out?

269 Chris January 27, 2014 at 8:50 pm

Wow, did this one ever hit home with me. I’ve been struggling for 20+ years now in a career “choice” that I’ve hated since day one. You’ve given me a lot to think about, and I thank you sincerely.
I would love to see your take on guiding our children to not “should” on themselves. The “shoulds” were so ingrained in me by my parents, and I don’t want my kids to have the same miserable experiences as adults that I’ve had because I “should” on myself for 20+ years. By the time they are old enough to start choosing, I want my kids to be ready. Ready enough to choose wisely while they are still young and flexible enough to chase down the life they want and make it theirs.

Maybe another blog, entitled “Don’t Should on Your Children” :-)

270 Brent January 27, 2014 at 9:05 pm

I found this especially interesting because it is essentially the reverse of what I have done. I flirted with law school and consulting because I felt like I should- instead, I became a teacher- a career that I have always felt compelled to pursue. I love teaching; despite that, it took years for me to stop beating myself up about NOT doing something more prestigious and/or better paid. It took leaving teaching for a year for me to realize that I had in fact made the right decision.

271 Doc January 27, 2014 at 11:54 pm

Wow – just this morning, before reading this, I was thinking along similar lines.

272 Christian January 28, 2014 at 1:40 am

Wow, my life summed up in 15 minutes of reading.

273 Jacobus January 28, 2014 at 3:36 am

I’m glad you have chosen to do AoM.
Little by little you are actively making me change my way of thinking and doing.

Thank you.

You have not only given yourself power, but you are empowering the rest of us too.

274 Bob January 28, 2014 at 5:10 am

Good article Brett and one that has its timing just right as yesterday I handed in my notice at the College where I have taught for the last 3 years. I am 67 years old (live in the UK) and have had a decent career in financial services, no big money stuff, and when I was laid off ended up bringing the experience to teaching.
Have enjoyed teaching but the demands in red tape, targets etc was doing my head in.
I am now uncertain whether my whole career was a ‘should have’ but having stepped back now it is my time so reviewing where I am and start learning not to ‘should’ myself.

275 Jack January 28, 2014 at 11:39 am

Good stuff for this college student (reluctantly slogging to get a bachelor’s in business). But, if I dropped out now, that wouldn’t be fair to my parents, who are paying my tuition. Plus, I need to think of what I’m passionate about. I need to have somewhere to go in mind of I change course.

276 I'm Just A Girl January 29, 2014 at 1:49 am

I’m of the XX chromosome, but I just had to thank you for writing this blog. It was amazing insight to things that someone I love very dearly is going through. Your blog made me take a step back and go “Okay, how can I be more supportive not of what he should do, but what he really wants to do?” Again, thank you.

277 Ryan January 30, 2014 at 8:00 pm

Thank you so much for writing this. I can’t explain how much it has hit home with me. I would really like a chance to talk more about this with you. As much as it has hit home, i find it hard to put into action. If you ever have a few minutes please email me. Thank you again for what could be a life changing article.

278 Giancarlo Fusco February 2, 2014 at 10:10 pm

What a great article! I am guilty of should -ing on myself, despite knowing better. I’ve started taking steps to fix that, but as you mentioned, after so many years it’s difficult to know what you want to do for yourself. Thanks for the reminder.

279 andy February 5, 2014 at 10:57 am

Bret this is great. I’m actually almost done with my bachelors in history. Like you I always wanted to pursue a career in education. Its been a long journey and I’ve questioned myself in the process. This article not only make me feel more confident in my choices I’ve made but makes me want to try even harder thank you

280 justin February 6, 2014 at 8:32 pm

Nice article,
when I was a child, my father quit working at General Motors to be a Park Ranger.
with a 60% cut in pay.

But he just couldnt stand seeing his children growing up in a big city and himself working in a factory any longer.

We didnt have alot of money, I grew up licing on top of some mountain or in the middle of some swamp.

wouldnt trade it for anything.

my wife and I now live in a city, but we have 8 acres about 100 miles away in the mountains and we try to take our child and spend as much time there as we can.

281 Zachary February 7, 2014 at 10:02 pm

It is a shame I only just found this article now. I have been “shoulding” all over myself for the past 4 years. I graduated from college last year full of regrets. Of things I wish I had done and things I wish I hadn’t done. Now out and working a job that I genuinely like, I still find myself daydreaming and thinking back to the past four years and wishing I could do it all over again. But what’s done is done, and what’s important is what I do today and tomorrow, not yesterday.

282 Matthew April 1, 2014 at 10:59 am

Ironically enough, I “shoulded” myself into a teaching career before I even had the opportunity to ask myself what I wanted in the first place. Similar to Brett’s story, everyone told me I would be a good teaching and I numbly went along with it.

After a year of teaching, I was miserable and horrified by the life I was pursuing. Not that teaching wasn’t rewarding; on the contrary, it was incredibly important, but merely not the life I wanted. (I struggled a lot with giving up a job that was incredibly important. But I finally came to the conclusion that I would be doing both myself and my students a disservice by staying in a job that made me truly unhappy.)

I resigned in June after completing my first year. Family and friends were disappointed, and I don’t blame them. But they liked like the image of their son/brother/friend working an honorable job as a teacher. That was their reality, not mine; I kindly suggested to those that vocalized their disdain to pursue teaching on their own if they found it that inspiring.
Now, I work at a jail, but I’m pursing a degree in forest management and silviculture. Although my current job is not ideal, I know it’s not permanent, but rather something of an income generator that allows me to pursue what I really want. I want to study trees and forests, and manage them.

This article really resonated with me, and confirmed my resolve to live life as I choose it.

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