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 }

101 Jon E. January 24, 2011 at 3:40 pm

Great post. I really think that this is the great manly struggle of a man’s life: separating from the should to go with one’s heart.

I’m at such a point in my life.

As a matter of fact, I’ve put myself through 2 Masters Degrees for my should, all the while planning to make money, retire, and teach and coach football at some small religious school.

I’m blown away by how difficult it is to work in the should and not in the place where my heart is.

102 Brett Swanson January 24, 2011 at 4:15 pm

There is not much to say that hasn’t already been said.
Thanks man, I dont know what the hell to do with my own life but, somehow, this article has cleared the fog from my mind a little concerning this subject.
Im going to read this a couple of times, set it in my mind and meditate on that shit!

Much respect to the whole AoM community, and especially Brett, Kate and Lil’ Gus.

103 Jack January 24, 2011 at 4:22 pm

Brett, This is probably your best article to date! I just wanted to say though, I’ve got caught in the should thing so often I have forgotten. The problem for me is finding it is that I REALLY want. Or what I REALLY want seems too hard and will cost the sacrifice and then when I get there, will I be dissappointed? Any advice? Could we have an article, by yourself or another AOM expert about tapping into what we REALLY want?

Thanks again!

104 Alex January 24, 2011 at 4:23 pm

Brett – fantastic article. I esp. like the mantra of replacing should with I Choose. That really hit home. I find myself realizing I’m probably a bit too late to have discovered I “should” be doing something else with my life work-wise. But it’s also OK as I choose to work hard at a job I’m not all that enthusiastic about to support the family I AM enthusiastic about.

Take note young men of the world! If your gut tells you you should be writer and not doctor, be a writer! If your guy says be something that appears unbelievable or unreachable, don’t go for the way of least resistance- GO FOR IT ANYWAY!

105 Brett McKay January 24, 2011 at 4:32 pm

Thanks very much for the kind words everyone. I sometimes find it hard to share stuff from my personal life-especially when it involves making mistakes!-so it’s great to hear that it’s resonated with many of you.


Have you read through our series on finding your vocation in life? It’s pretty much a summation of all our thoughts on finding what you want to do in life.

106 Jennifer M. January 24, 2011 at 4:46 pm

Trust me, this isn’t just a male problem. As a single woman in her 30′s, I struggle with this constantly! I would love to pursue art/writing/living/traveling… anything but what I “should do” – which would be grad school, corporate job, internet dating to land the perfect guy. I can’t quite figure out how to live what I feel to be my truer self without first going after the “shoulds” so that I have the money needed to live the way I want, but… Yeah I totally feel where you’re coming from.

Don’t give up! I love that you’re wrestling with this idea and really trying to live more authentically. You’re setting a wonderful example for your children and showing them that they don’t need to buy into the “shoulds” that our society places on us. Bravo!

107 Matthew Dorry January 24, 2011 at 4:51 pm

It’s great having you back full-time, Brett. I had been curious about why things were getting a little dry here. And congratulations on ‘choosing’, not ‘shoulding’. What you’re doing here is amazing. There are bits of truth about life I doubt I would have even glanced for a very long time without AoM. Thank you. I am forever indebted and glad to have you as a full-time ‘teacher’ again.

108 Patrick K. January 24, 2011 at 4:59 pm

I loved this post!

I’m set to graduate highschool in 4 months and going to the best college in my state. Planning on majoring in engineering and going to law school after, but I’ve always wanted to work in film.

I’ve thought about just making short films while going to school/working, but I wouldn’t be able to give either 100% Knowing that I could be very successful if I do the college route, it would feel like such a waste if I chose film and ended up failing. I’ve ruled out film school, and it seems to be too expensive to go to a good school in L.A.

If anyone has some advice, feel free to let me know.

109 TJ Mullin January 24, 2011 at 5:23 pm


Thank you for this article and thank you for AoM!

110 jorge January 24, 2011 at 5:52 pm

This article reminds me of something Robert Heinlein once wrote:

“Do not confuse “duty” with what other people expect of you; they are utterly different. Duty is a debt you owe to yourself to fulfill obligations you have assumed voluntarily. Paying that debt can entail anything from years of patient work to instant willingness to die. Difficult it may be, but the reward is self-respect.
But there is no reward at all for doing what other people expect of you, and to do so is not merely difficult, but impossible. It is easier to deal with a footpad than it is with the leech who wants “just a few minutes of your time, please — this won’t take long.” Time is your total capital, and the minutes of your life are painfully few. If you allow yourself to fall into the vice of agreeing to such requests, they quickly snowball to the point where these parasites will use up 100 percent of your time — and squawk for more!
So learn to say No — and to be rude about it when necessary.
Otherwise you will not have time to carry out your duty, or to do your own work, and certainly no time for love and happiness. The termites will nibble away your life and leave none of it for you.”

111 Bradley January 24, 2011 at 5:58 pm

This article has perfect timing. I’m 42, have the wife, kids, mortgage, and the unfulfilling job. Thanks for a great post!

112 Greg M January 24, 2011 at 5:59 pm

Excellent! The content on this site consistently challenges me. Keep up the good work!

113 Jim C. January 24, 2011 at 6:00 pm


Very inspiring post. Congratulations on choosing your passion. I am confident that all of us in the AoM community will benefit from your decision. AoM is making a difference in my life and helping me to be a better father and husband. All the best to you, Kate and Gus.

Jim C.

114 Doug H January 24, 2011 at 6:08 pm

I love this article, I have been struggling with college because “I should” and I have found a degree that I’m happy learning about. I know I could make a forester worth anyone’s time and effort but after seeing what nurses did for me growing up and having experience taking care of folks that are sick, then I really think that is my passion. I have been dabbling in applying for nursing school but have been tentative. I might just do it and get away from being a peon at the big corporation.

115 Marty.B January 24, 2011 at 6:43 pm

Kudos on the article Brett, I think that’s really “manning it up” (as my friend says) about honestly sharing your mistaken life-directions. I find that I’m interested in parts of my vocation (architecture) and enjoy parts of it, not all of it. I often have doubts, and will check out that ‘vocation series’. I think the best parts go to those in my profession who ‘hustle’ with long hours, to the detriment of any family / non-work responsibilities. I would rather be a great father and husband than a great architect, and at the moment it seems I cannot do both. So I’m feeling the humdrums a bit with my job and wish I could be one of those people who’re absolutely passionate about their work. Anywho. Your article was great food for thought. One question though – ‘Jagweed’? I’m in Australia and have no idea where they come from. Little help?

116 Kristinn January 24, 2011 at 7:02 pm

I have regularly visited this site for quite a while, but this is the first time I leave a comment.

I just want to congratulate you on this step, and on being able to do something you enjoy. I also want to thank you for having created the Art of Manliness. I have both enjoyed these articles, and benefited from them. For example, I have gotten first date ideas, taken up straight-razor shaving and boxing, and taking up carrying calling cards.

I am myself approaching crossroads, having to make the first non-obvious choice in my education, choosing the direction I will take for post-graduate studies. But as often before, an article here on the Art of Manliness has helped my resolve, and strengthened my trust in my own wants. Manliness really stems from integrity and being true to yourself.

Thank you for this article, and all the time you’ve put in this site.

Yours respectfully,
Kristinn Kristinsson

117 John January 24, 2011 at 7:02 pm

What a great article! Thanks!

118 Erick R. January 24, 2011 at 7:09 pm

A very good article! I think I’m going to send it too my brother and reread it a couple times myself. Also, I was always kind of curious if you ever went of a mission, and it is interesting to see you mention it in this article. Very cool.

119 Mike January 24, 2011 at 7:16 pm

Great article!

120 Hector January 24, 2011 at 7:20 pm

Awesome article! I understand clearly because I’m about to graduate high school and everyone tells me that I should be a lawyer or enter into politics. I care for both but none of them are what i would like to do. i would like to be a teacher because it’d be something cool. This article was just superb.

121 Justin January 24, 2011 at 7:39 pm

Thank you! inspiring read.

122 Gareth January 24, 2011 at 7:56 pm

Great post, Brett. I think a lot of people can identify with the struggles you illustrated so well from your own experiences.

123 Jesse H January 24, 2011 at 8:18 pm


I have read some fantastic, fantastic articles on this website and it has been a guiding light for me for a long time now.

This article, however, I must commend you for – it is the best, most personal, and most educational article I have ever read from you. And to show your ‘manliness’ was the fact that you had the heart – and the balls – to admit all of these inner weaknesses in full detail to all of us.

Congratulations. Congratulations to you to finding what you really wanted to do in life and congratulations for choosing and making a choice that was both intensely personal and wholly, 100% yours.

You ARE a teacher, and you have taught many men how to center themselves around being better – for themselves and for everyone around them, and I’m proud of you and I’m very lucky to be part of your audience.

Keep doing what you love and kudos to you for being a true man.

124 Andy January 24, 2011 at 8:30 pm

@ Manuel:

I can only recommend the place I’ve been at, Phromthep Muay Thai. It’s more fitness focused rather than muay Thai, but then you get friendlier people instead of meat-heads that fill up places like Tiger Muay Thai (most popular place in Phuket, but bad reputation as well). My advice would be to stay out of the Patong region if coming to Phuket. Also, I’ll be at Ko Samui at Super Pro which I’ve heard good things about. Bangkok and Chiang Mai have some great camps as well, but Chiang Mai is generally for more serious students and Bangkok can be hard to live in. Good luck!

125 Michael January 24, 2011 at 8:50 pm

Congratulations on taking the leap, Brett! Your substantial mettle shines, and you’ve built a platform of integrity that will help you construct even greater successes. Like everyone, I’ve “shoulded” when I would have been better served to follow my heart, and like you, I’m embarking on a new journey – at times scarier than the “should” version, but more soul-satisfying to be sure.

Another thing: I’ve noticed and appreciate how your posts reflect more humor and personality as time goes by. Cheers!

126 Sam January 24, 2011 at 9:16 pm

This is one of the best AoM articles I have read and it has come at a point in my life where it really touches on what I am going through. I’m a college student struggling with what direction to take my life in, and without going into too much detail, this article really hit home. It has left me with an optimistic outlook on my future, and what I choose that future will entail. I’m very glad to hear you will be back full time on here, and I want to thank you for all the great work you have done on here and for always leaving me motivated and hungry to be a better man.

127 Hugo Stiglitz January 24, 2011 at 10:02 pm

Good article, and some good comments, but I think some people need to stop daydreaming for a little bit and get back down to earth. Hey, sometimes life isn’t fair and yeah, it sucks that some of us have to put in 60 or more hours per week to make a living and support our families, but when you think you’ve got it tough just remember the thousands of 19-year-olds who stormed the beaches on D-Day and never had time to think about what they “shoulda and coulda” done. Working a sucky job is a menial sacrifice compared to the ultimate sacrifice that thousands of young men made many years ago and still do this very day. Yeah, I guess in a way it is manly at times to go against the grain and follow a passion, but as a few other people have pointed out, that only makes sense if you can afford to do so financially and otherwise. Of course just about anyone would LOVE to quit their job and follow their “dreams,” but face it, the jobs that pay well are jobs that are tough hard to fill. Case in point is post #106 above: “I would love to pursue art/writing/living/traveling…” well, DUH, who wouldn’t want to??? That’s why jobs are called “going to work,” NOT “going to play.” This country is being overcome with a sense of entitlement on all fronts, and that is why we are falling behind the rest of the world in just about every measurable statistic of success.

128 Keith Brawner January 24, 2011 at 10:09 pm


Thank you for the great post and your continued time and investment into this site. I hope that this site continues to be your passion. It has helped me in more ways that I can possibly list here, but I’ll list a few anyways:
Professional – inspired me to go out and find my passion. This has led to a 25% increase in salary, more satisfying work, greater happiness, and a brighter future in general. It’s odd how hunting your passion produces better work.
Personal – has helped provide date and relationship ideas to myself and my wife.
Fun – Nothing is more fun than an adventure. My adventures are no longer complete without my Saddleback. We will go on a European backpacking trip this summer with a number of the tips provided here.

Thank you. Your help is invaluable. Also, your law degree is not wasted, it has tempered a number of your articles at this site.

– Keith

129 Ann I. Ball January 24, 2011 at 10:16 pm

Thanks for sharing. There’s a lot of unnecessary bravura when you get into the “should” careers – people not wanting anyone to think less of them because they don’t continue “that job;” other people willing to tell everyone that “so-and-so just couldn’t hack it and that’s why he left.”


I’m happy that you not only know what you want, but you also know how to make it pay (this latter part stops people in their tracks).

It has taken me three years to become accustomed to a job that I dislike. The only change, really, has been my attitude. I’m still looking for (and trying to build from scratch) the job that fits my career wishes, but for now I’ve chosen not to make people miserable during my journey (including myself). Having definite goals and deadlines keeps ones spirits buoyant.

130 Jim January 24, 2011 at 10:22 pm

This is a great article! I’m going to pass it along to some friends who “should” read it.

I resisted a lot of “should-ing” on my path to medical school (right down to not wearing a blue or black suit to interview), and I’m glad I did. I’m now interviewing candidates and secretly rolling my eyes at the cookie cutter applicants who never thought about what they could do to separate themselves from the competition while pursuing their actual desires.

Cheers, Brett!

131 Doug Mathers January 24, 2011 at 10:30 pm

I JUST did this too. I shoulded myself into going to school for something I really don’t give two cents about! Just have to find a way to do what I love on the side.

132 Alejandro January 24, 2011 at 10:38 pm

I wish I’d read something like this 20 – 30 years ago! I’ve always pretty much done what I should do, instead of what I wanted to do to make myself happy. I’ve spent a good part of my life trying to ensure other people satisfied are with me; that is, pleasing others at my own expense. I ended up with little self-confidence and a recurring sense of victimhood. When I was a teen in the early 1980’s, my parents told me I should go to college to study computer science because that was a growing and very lucrative field. So, when I started at a community college, I did just that – took computer science courses. Of course, I didn’t know what the hell I was doing because I really wasn’t that interested in it. Now, I know a lot about computers because of the current environment. My parents also told me I should meet a nice girl, get married and have kids – after I earned my computer science degree. But, I was too shy just to go out and meet anyone. It wasn’t until my mid-30’s that I slowly started to realize how much I’d lived my life to comport with other people’s ideals of how I should be. Now, instead of listening to what others think is the proper way to live, I cut them off before they get too sanctimonious. Other people’s rules don’t necessarily apply to me. Life is too short to worry about what people think of you!

133 Matthew Dorry January 24, 2011 at 11:30 pm

@Patrick K. “Knowing that I could be very successful if I do the college route, it would feel like such a waste if I chose film and ended up failing.”

You should never think like this. It’s spiritual suicide. Work hard at what you truly want to do. School or no. Success comes later. If it doesn’t, you can look back on your life with pride that you roughed it for the things you yearned for in life. You can never hate yourself for that, but you can hate yourself for letting fear and money rule you. I once filled myself with thoughts of failure, but I realized that even if I do fail (Which I think is actually impossible), no matter what it is, at least I can know I gave it my all and learned something about myself. That builds character. If you don’t try, then you’ve already failed.

Film is an art form and as hard as it is not to think of money when going in to film, it’s not about the success. It’s about the creative expression. John Cassavetes (Who you should look up) once said that he didn’t make movies to make money; he made movies to spend money. A similar, illustrative story is that of one between Diogenes and Aristippus:

Both were philosophers. Diogenes, a cynic, lived an ascetic life, living on streets, sleeping in public tubs. Aristippis, on the other hand, was a hedonist, the founder of the ultra-Hedonist ‘Cyrenaic’ school, and concerned himself with being a part of the ‘cool crowd’. When Aristippus encountered Diogenes on the street, he said (Not verbatim) “Diogenes, friend, if only you would learn to offer thanks to the god Dionysus and adjust yourself to the customs of the wealthy, you would not have to sit here, eating mere lentils.”
To which Diogenes wisely replied: “O but Aristippus, if only YOU would learn to live off of mere lentils, you wouldn’t have to thank Dionysus or adjust yourself to the customs of the wealthy.”

Think about it.

134 Jesse January 24, 2011 at 11:33 pm

Love it. Thanks.

The only thing I would add is this. I have noticed over the past couple of decades (just turned 39 in December . . . wow . . .) that ‘choosing’ rather than ‘shoulding’ is something that requires frequent re-visiting. If you are really practiced at ‘shoulding’ yourself, your brain can be soooo subtle with the justifications. I find myself looking at choices from the back end wondering ‘wait, did I really choose that path, or did I just scam myself?!?’

Great post. Thanks again.

135 Carlo d. January 24, 2011 at 11:52 pm

Outstanding article! How do you do it?! hurrah!

136 Jimmy January 24, 2011 at 11:56 pm


Thanks for another great article! I’ve been a fan of AoM for a while and I got the book for Christmas. Glad to hear you’re officially doing this full time. My father gave me some of the best advice of my life: Do what you love, and you’ll never work a day in your life. I’ve followed this advice throughout my life and it’s led me to a fulfilling life as a designer. I’ll never be rich, but hopefully I’ll be happy. I hope others will do the same.

137 Chris Sandor January 24, 2011 at 11:58 pm

Very well put. I’ve ran into this problem. I went from studying engineering and going into the military to being an Airline Pilot and a history degree. I’ve figured out what I am passionate for and pursued it. Thanks for the article, once again very well written.

138 John R. Alley January 25, 2011 at 12:04 am


Thanks for the amazing article. I should all over myself all the time, to the point I’m up to my next in should. As you pointed out shoulding “leads to feelings of resentment, anger, and depression.” This is where I presently am. But thanks to your article I am going to reconsider what I truly want to choose to do.


139 Powers January 25, 2011 at 1:08 am

@Matthew Dorry: That story reminds me of one of the benefits of living a frugal lifestyle: freedom from an unhealthy obsession on salary, or working just to acquire more crap. I think too many folks prostitute themselves out for more money at the expense of self-fulfillment or meaningful work. I first had this realization when I heard recruiters from some high-powered consulting firm speak at a college career fair. Sure, you could make good money if they hired you, but you were expected to work 50 to 60 hours per week in a high-stress office environment. No thanks. Instead, I gravitated to the Forest Service’s booth, learned about some of their awesome positions, and am now studying to get a (lower paying) but awesome job in natural resource management.

140 Bay January 25, 2011 at 2:10 am

So, my husband, who is always right (blessing & curse) has sent me a few of your posts and I gotta say; they really hit the mark. I have been on a career tirade for the better part of 5 years now and it’s really exhausting. I’ve really pushed it. Can’t get the job I want? Not enough education/experience? Whuppah! Got an MBA! Take that, suckaz! Only thing is, I graduated in a recession and can’t get out of my government job, which is not-so-slowly but surely sucking the life out of me. My undergrad wasn’t particularly intelligent (“Anthropology? Writing? But what can you DO with that?”), but I did co-ops so I’d get my foot in the door after I graduated. The only problem is, my foot’s been in all the wrong doors.
I was going to be a dancer/actor and a writer. Someone creative and fun, to match my creative and fun self. But now I’m ancient for dancing and acting, and writing in all the wrong places is killing my desire to write.
So, while I can read this post & nod along, I find myself need more: How do you get yourself off the merry-go-round? I grew up dirt-poor and am terrified of being that way again (though, I’m not doing well, salary-wise, and certainly not for an MBA who has to, um, pay for their MBA while her husband is in law school). So now what? Advice? Tips?

141 Ali January 25, 2011 at 4:58 am

Thanks a lot for sharing your story buddy! I too am, not an exception of this ‘should’ thing and could relate to it very well.I have thought a hundred times to give up living according to others’ expectations, but never had that courage to surprise and embarrass my loved ones because of my decisions.Another reason behind this is, may be I am unaware of the ‘thing’ that would lend me satisfaction when I call it ‘work’.I don’t know whether other people face the same problem as I do, but the fact is that when I sit to think of what I like to do the most , my mind goes blank.May be a long stint with this ‘should’ thing have taken it’s toll.:)
At present, I am in between of another should thing i.e a Masters’ degree in Chemical Engineering(though I always scored above 90 in mathematics:), but those lifeless equations never appealed to me).I hope when I get out of it, I am able to choose something that actually pleases me , and for that I know a lot of soul searching is required on my part. But it would be great if I get some help from you my dear friend, Brett:).I mean, if you share an article regarding, ‘how to figure out for yourself,what you actually want to do’, it can be of help to scores, for I hope, I am not the only one facing this problem!!

142 Josh Knowles January 25, 2011 at 6:43 am

Thanks for your honesty in this. It’s encouragement to me as I plod my way through seminary while working on the side. As I look around, I see plently of guys my age (25) who have a “real job” or a “career,” who make way more than I do, and who have way more and way nicer “stuff” than I do. And I wonder how many of them have already realized that they’re just putting in one more day until they can retire – 40 years from now.

In my weaker moments I start thinking those should thoughts. Maybe I should’ve taken a degree in something that would guarantee me a big salary. Maybe I should’ve gotten a job with the power company so I could retire early with a goverment pension. Maybe I should’ve at least worked a high paying job for ten years or so and then… Maybe I should’ve, maybe I should’ve. But then I realize that once I had purchased all the toys I wanted, the truth would have hit me. I don’t like this.

Thanks again.

143 Colton Wilson January 25, 2011 at 8:28 am

Awesome post, Brett! I had often wondered if you might be having this struggle (between law and AoM). Glad to see you made the “right” choice! I went through a very similar experience myself. I started going to engineering school, even though I had wanted to be in a teaching ministry since I was 12. I had even been teaching classes at my church (even to adults) all through high school. But somewhere along the way, I caved, too. About every semester, the regrets would start piling on, but then, so would the shoulding. Finally, at the end of my third year, I came to my senses, “dropped out” of college, and started Boyhood Restored, the ministry I knew I was meant to do. Amazing how things work together. That very same summer I met my wife and we were married in January. The following spring I started turning my high school job into a full-time lawn service. I’ve been able to make both my dreams (being in ministry and owning my own business) reality. And they are both seeing great success. Now that I’ve got one kid and another on the way, I am more excited than ever about what the future may hold (especially when it comes to seeing how four people can live in a 1bd/1ba 800 sq.ft. house). “Choosing” not “shoulding” was one of the best decisions I’ve ever made.

P.S. Even though I often look back on my experiences and am tempted to think, “what a waste!” I usually realize that even the time I spent in college taught me a lot of useful things that I am using now. Nothing is a waste. Go forth and conquer, my brother!

144 Stephen January 25, 2011 at 9:02 am

Awesome post. I have “should-ed” myself for much of my career. It’s nice to realize I am not the only one who thinks like that.

145 Am January 25, 2011 at 9:37 am

First off, congratulations. You obviously inspired a lot out there. More power to AoM.

You were in the same situation as I am now, different only in that I have a medical (not law) school scholarship. I feel the same way about med school like how you felt about law school (like I should pursue it for the money and the prestige). I just have to ask this out of curiosity:

What do you think of your going to law school? Was it a waste of time? A mistake?A blessing in disguise? Something you regret? Something else?

Thanks man.

146 Colin January 25, 2011 at 11:40 am

You are an exceptional teacher, Brett! Thank you for your commitment to this site and providing a resource for men to continually learn from.

147 Daniel Gardner January 25, 2011 at 11:41 am

Beautifully said, Brett. Thank you for sharing. God bless you, Kate & Gus. Don’t look back.

148 Rick G January 25, 2011 at 11:42 am

Great post, Brett! It sounds like you found your Chazown! ( If more men followed their vision or their passion, they would be happier and their families would probably be happier, too. Thanks for challenging me not so should on myself.

149 Josh W January 25, 2011 at 12:21 pm

A lot of “shoulding” can come from fear of failure and a lack of belief in yourself. I know many times in my own life I’ve taken the “safe” road, which is usually a “should”, because I was afraid that what I wanted was impossible or at least too difficult to obtain. I would remove bits and pieces from my dreams and shape them into a nice safe “should” that gave me all the zest of stale water. Or I would drop a love or a goal because I wasn’t good enough, and therefore “should” do something else. I’m currently trying to clean up the mess and get to the road of doing what I love, which is much more difficult the further down the path of life you get. To all the posters in high school, do what you want right now. Don’t put it off. Cause once you’ve got the “should” degree and rely on that office job for money, and have a couple kids to feed and a mortgage to pay, changing gets lot more difficult and complicated.

Congrats on making the switch Brett. You’re doing a great job with AoM.

150 Allen January 25, 2011 at 12:29 pm

Ahhh…the price one pays for experience, I should have read this article 30 years ago had it been written but they too would have had to have the experience of dealing with all the “shoulds” in their life also. As I look back now I know it was the fear of the unknown as it is today with any man wanting to follow his dreams. Mother told me that saving twenty five cents out of every dollar that came my way would ease the fear of how I was going to survive in life as a man but did I listen, no. Excellent read my friend, now to the younger men reading……….will you listen to the voice of experience?

151 Isaac January 25, 2011 at 1:22 pm

Awesome article.

My life has been a constant evolution from “should” to “do”. After high school I went into computer science because I had good math skills, liked computers well enough, and it was a hot field… so I was told I “should” do that. Well, after a couple of years I realized that sitting around writing code all day was awful.

So I switched to Finance, because I liked business and was good with numbers, plus there was good money in the field. Well, I graduated with that degree and worked in the banking industry for a year. I hated that, too. It was basically the same as writing code.

During that time I’d become very interested in the gym and had become a certified personal trainer, more out of interest than anything else. I was given the opportunity to go back to school for Exercise Science. Everyone told me how stupid that was given my advancing finance career. I jumped anyway (my first real “do” over “should”). After two years I had a Master’s in Ex. Phys and was going to rule the world.

Fast-forward a few years later and I’m getting ready to be married to a girl that it wasn’t working out with (should), training wealthy, lazy people that I didn’t like (should), and feeling pretty miserable.

Things finally blew up and I had a breakdown. I’d been living like a boy in a lot of ways and especially in doing what I was told that I should do.

I’m not going to lie. It was a long, hard year to get myself back to where I was feeling good about things. Now, though, I run my life on my terms. I’m fire-hardened and the failures taught me to do things the way I want to do them. Some lessons I think have to be learned the hard way and this part of being a man might be one of them.

Once you do, though, your life is going to change.

152 Brett McKay January 25, 2011 at 2:04 pm


Going to law school definitely wasn’t a total wash. My writing improved many times over and I learned valuable critical thinking skills. I also sometimes have to look over contracts with stuff for AoM, so it comes in handy then as well. So I’m grateful for the way it sharpened my mind–I just wish I had done a less long, expensive, and soul-sucking way of doing that-say, getting a masters degree in something I was actually interested in. But to me, the way I think about it is that who knows if I would have started AoM if I hadn’t gone to law school and needed a creative outlet? So even our “mistakes” can bear good fruit.

153 Joshua Lowe January 25, 2011 at 2:59 pm

Brett, you are a inspiration.

I too want to teach History but everyone around me keeps saying “Josh you were born a lawyer!” Sure i can talk and think with the best of them, but im not sure i would be happy being a lawyer while i know would love to teach. And this is a critical point in my life because im in my first year of college so the chioce is looming ahead. After reading your story it has helped me realize i am not alone. My family never understood my wanting to teach so they can not relate to my feelings. There is just some thing about passing knowage on and helping sculpt young adults into the best people they can be that almost has a romantic quality to it I cant ignore. And this article really speaks to me.

So thank you Brett.

154 James January 25, 2011 at 3:10 pm


Thanks for being so transparent and sharing this with the AoM community. You’ve created an awesome thing here and I greatly appreciate the work you have so diligently put into it. The fact that I am wearing a sport coat as I write this is a testament to the positive influence AoM has wielded among its readers.

I am currently going through a similar process of “should-ing” myself as I am in my last semester of college. When I joined the Navy seven years ago I learned about the Navy SEALs and became enamored with the idea of joining up. But I was very out of shape and the dream seemed impossible. I started training diligently and after years of hard work (thanks to Crossfit) I have achieved a level of fitness that I would have never thought possible. I decided to go back to college and finish my degree before I embarked on my warrior journey, but as graduation rapidly approaches I find that I am second-guessing my decision. Some of my friends and church family are against it, and others say that I will never be able to have a family. My mom wants me to be a lawyer and become “financially successful.” I keep fighting against what I should do, and what I really want to do. Thanks for the encouragement, and keep up the good work!

155 Jay January 25, 2011 at 3:18 pm

I have to say, Brett, this article made me incredibly thankful that I *didn’t* go to law school. Law was once my dream career, for frighteningly similar reasons: the automatic, baseline prestige, the “guaranteed” high-paying job, the lifelong barrier against anyone looking down on you. There was just one problem: I had absolutely no intrinsic interest in the law!

For too long, the fact that it was “a good career for communicators” was enough to give me enthusiasm. But the more I thought about it, I realized my true passions lied with entrepreneurship and the only reason I thought about law is that’s “guaranteed” and entrepreneurship isn’t.

Of course, as you said: if the only (or main) reason for doing something is because other people will be less critical, that’s a really BAD reason. At 24, I now run a wildly profitable business with my best friends and could not be happier about that choice.

Thanks for the inspiring article!

156 Jim January 25, 2011 at 3:19 pm

WOW! This article is serendipitous to say the least. I am a 4LE, my wife is pregnant, and in my third year of law school I discovered I did not want to practice law. With only one year to go, however, I figured it was best to get the degree (still, I think, a wise choice).

My first year, of course, was a meat grinder. But, I escaped relatively unscathed, procured a student rep position with Lexis and a law clerk position at the Public Defender’s Office, made Dean’s List every semester since my second semester, have won several very nice pieces of paper that tell me I was very skilled at learning a specific subset of law (the omnipresent law school should goal called the “High A” award), and won a few awards from nationwide organizations who misspelled my name every time (really ABA…really???!!!).

Now, I’m in my last semester and I have been attempting to figure out exactly what I want to do with the rest of my life. Law school was a should for me. I am 36 years old. Before law school I was an Iron Worker. I made good money, for the most part enjoyed the work, and really loved the brotherhood. Unfortunately I tore some ligaments in my knee and was unable to work for a few years. During that time I returned to school and finished my undergraduate degree (I started it in 1993, but life took me on a few adventures and I ended up having a great time instead of getting a degree). A bit wiser, I really enjoyed school and found that I was very, very good at it. I graduated summa cum laude in 2006 with my BA in political science. And then I found myself in the midst of a “should storm.” “Jim, you should go to law school, you’d be great at it.” “Hey, you should go to law school, you can make some serious money as an attorney.” “You shouldn’t waste your degree by getting a masters or PhD, it’ll take too long, you should get a practical degree, like a law degree.” Shoulds rained down like hale. And, eventually I got sick of the storm and ran inside……..I ran right into the LSAT, right into first year, right into the most insanely competitive academic environment one can imagine, right into tenured professors hiding the ball, and right up should creek without a paddle.

Now I’m at the point where I have to decide which way to go: take the bar, keep up the charade, and continue to strive for personal mediocrity; or, take some initiative, really dig down and find my vocation, and parlay my degree into something meaningful? I choose the latter. From one law school vet to another, thank you Brett. Thank you so very much.

157 serg January 25, 2011 at 3:38 pm

This reminds me a little of me…. the only difference is that I could not preform well in any other tasks besides what my gut told me to do.

Still it took me 5yrs to grasp that fact.

158 Katie January 25, 2011 at 3:59 pm

Thank you for writing this. I’ve been trying to get myself out of the “should” category for a couple years now. I’ve taken a step into getting a different job and being able to go back to school to become a police officer. Now I know that I need to stop pussyfooting around and just do the damned work.

159 Insomniac January 25, 2011 at 4:46 pm

This is a great article. I wish I had seen this about, oh, twenty years ago. My life course has been one of shoulding on myself (and others who should all over me along the way). It’s a miserable, soul-sucking, self-negating path. If you haven’t gone down that road yet, don’t.

160 Chris W January 25, 2011 at 5:01 pm

I enjoy your website. Reminded me how to properly tie a windsor knot not too long ago.

I, too, went to school in Oklahoma (Oklahoma State). I, too, have a passion for teaching. I, too, went to law school (twice, long story) for all the wrong reasons. I have now been practicing law for almost 15 years. I now own my own law firm (after working at 2 law firms for others). What I have found is that I enjoy “teaching” my clients about different options for their situations. I enjoy “teaching” staff how to handle different projects and watching them succeed and grow in their jobs. I think that you can take the situation that you have “shoulded” yourself into and mold it so that you can use your talents and passions. It takes guts, patience and hard work, but my point is that sometimes you take lemons and make lemonade. Don’t let a situation dictate to you how you act within the situation. Be true to yourself in whatever situation you find yourself. Sometimes you don’t have to recreate the wheel to be happy.

161 Jim January 25, 2011 at 5:52 pm

Chris W–Fantastic points! Particularly: “Don’t let a situation dictate to you how you act within that situation.” Making the best of a bad situation may just lead one to his vocation when it’s all said and done. Bravo man.

162 Richard, Ogden, UT January 25, 2011 at 6:02 pm

This is a great article! Thank you, and keep these good things coming.

163 DLB January 25, 2011 at 6:33 pm

I was fortunate to choose I career that I loved, conducting music and teaching. However, I also spent most of my life living daily with the “shoulds” that I thought others expected.

In retirement, I am definitely finished with “shoulding.” I now choose what I wish to do and choose what I wish to accomplish. My friends are upset that I am not continuing to clinic and conduct choirs. They don’t understand that I loved my job but now I want to explore a lot of things I didn’t take the time for when I was so busy conducting and teaching. I get up with each day with a sense of joy and wonder and can’t wait to tackle a new day. My new interests include composing, reading, cooking, working out in the gym, shaving with a straight razor, listening to music, and logging on to AoM.

164 Simon January 25, 2011 at 7:04 pm

Conrgats! Your community here is strong, and we preach the gospel of AoM! :-)

165 Scott January 25, 2011 at 7:50 pm

Excellent read. Thank you for the inspiration. I should-ed for 8 years in the IT industry, because that’s what was expected of me as a young father to provide for the family. I finally made the switch to what I really wanted to do about 7 years ago to public service as an emergency manager. I don’t make nearly the money I once did, but I love my job, I love my co-workers and am passionate about what I do everyday.

166 Ann I. Ball January 25, 2011 at 8:58 pm

A few of things I’m learning after abandoning “shoulding” (this is an on-going journey)-

(1) How to be gracious when people insist on referring to you as that thing you’ve decided not to be. I realized that I spent too much time thinking about this and not enough time thinking about my next move. My focus was off. I haven’t yet mastered grace, but I’m a sight better now that I’m focused on a goal.

(2)The degree was not a waste of time because I learned lots of new things. Yes, it was more expensive than necessary to learn those things, but still, I did gain some confidence in mastering a subject.

(3) I have better instincts than I thought. Even before graduation, my initial reluctance for pursuing the “should” career was vindicated. As a consequence, I have stopped the knee-jerk dismissal of my own decision-making skills and evaluate them as objectively as I can, just as I would any one else’s advice

I learn a lot from the wisdom of others, but I take notes from myself as well. I’m finally accepting myself as an adult who has something to offer.

(4) In reassessing the exploratory years, the ones where I wasn’t sure if I should do this or that, I realized that I had not compromised my core values, which makes me happy.

167 MCH January 25, 2011 at 11:10 pm

Good read. I’m definitely a recovering “should-er.” It’s nice to know someone else out there struggled with being a people-pleaser. It’s definitely a challenge reading your own interests and seeing if they are what you’re meant to pursue or not.

168 John January 26, 2011 at 12:02 am

Many people have worn those shoes. I graduated top of my class as an undergrad and jumped right into my masters. I “should” all over myself on this decision and I ended up dropping out of a nationally ranked program, and for all the right reasons. The funny thing was, I knew exactly what admissions wanted and I should myself all the way into the university. After spending a semester contemplating, I knew exactly what I wanted to do all along, to join the army as an officer.

I understand entirely that sometimes we can be our own worst enemy. “The professor thought you should do it, its a safe career move, the money will be flowing someday from the gods.” And that’s exactly what is wrong with our society. It’s so easy to get caught up with what everyone else is thinking and we care too much about the alphabet soup that comes before or after or names (ie. MD, JD, PhD.) and it becomes a place to hide when its time to make a decision. Sometimes it takes a leap of faith and trusting your gut instinct no MATTER what anyone else thinks because YOUR the only one who is going to suffer the consequences.

This article has much to do with learning how to lead your own life and disregarding the static that society creates. I read this from an online interview of Major Dick Winters who was portrayed in the HBO series Band of Brothers and I believe he grasps the concept of this article. I read it probably 5 years ago and it has stuck with me to this day and I believe it applies to this situation. Its about knowing how to read the situation and taking time to gain perspective:

“For the nine months prior to the invasion, I was there and studied, developing my own personality, my own personal perspective on command. Most of the other officers never had that. It was a chance for self-analysis. If you listen and pay attention, you will find that your own self-consciousness will tell you if you are getting off track. Nobody will have to tell you that what you are doing is incorrect or ineffective. If you take advantage of opportunities for self-reflection, and honestly look at yourself, you will be able to be a better leader.”

169 Ed January 26, 2011 at 1:16 am

Of course, I think there is an option between SHOULD and WANT. I call it HAVE TO. I am working at a job that I neither want to be at nor should be at, but at this point in time I have to be at. After nine months without a job my bank account was down to single digits before this job got offered to me. I borrowed a few dollars from my parents to be able to afford to go to work for the first few weeks and since paying them back last fall I’ve been trying to build up some savings. I’m slowly improving those numbers, but in this environment I feel like I’m going to be stuck at a relatively dead end job for the foreseeable future.

I know you didn’t mean it this way, but some of us don’t have the luxury of quality choices. Should doesn’t always come into play. Sometimes we merely have to trudge through for a few years.

I moved twice in four months last year before finding a place cheap enough with a friend to carry me into the summer before I got this job. I was sleeping on an air mattress for eight months with barely any heat in the apartment last winter while counting on a 20lb bag of rice my mother gave me to be the base of most of my meals.

Plenty of people have it worse than I have as I at least landed a job last summer, but SHOULD just doesn’t cut it at times. We don’t always have choices worth taking. Sometimes we just have to take what is offered.

170 Ozone January 26, 2011 at 1:23 am

What an awesome article! I *think* I’ve found the profession I want to be in (higher education), but in hindsight, there were probably a few ways to get there. But what hit home for me is that I often “should” myself on minor things each day. Sometimes in retrospect there was something I indeed should have done differently; but for many things, I chose to do things the way I think should be done, so why second guess myself, and why care so much about what others think? I just finished a conversation with a former colleague of mine who has since gone to another organization. I’m considering a position at this organization as well, and I was asking a lot of, well, “deep” (probing?) questions. I suspect at the end the questions may have been getting uncomfortable – not on a personal level – but treading into waters that he would rather not go. I hung up, thinking I “should” have not asked so much, but then, these are things I – or anyone else for that matter – would honestly want to know. In the end, it is what it is, and frankly, I don’t think there is any real way around asking what I *should* ask about.

171 Vaughn Griffeth January 26, 2011 at 2:12 am


I believe this to be the most powerful and honest article you have ever written on this site. I can’t imagine the inner turmoil and indecisiveness that you’ve gone through in order to arrive at your true aspirations. I feel embarrassed to passively read through this site after implementing what I’ve learned from it, now that I understand how much hard work and sacrifice that both you and Kate continue to put into it.

With my own child on the way, and an uncertain future, your site has given me a heightened sense of knowledge and ideals that I may not have gotten otherwise. You and Kate have my sincere thanks and gratitude for creating it, and for providing me the inspiration to begin removing my own “should’s”.

Rest assured, as difficult as I’m sure the decision was to write for the “Art of Manliness” full time, your work is very much appreciated.

172 Tayo January 26, 2011 at 2:14 am

Mr. Brett McKay, you never stop impressing me with your articles. I really love this articles. It reminds me of when i quit my job to years ago because i did not like the way i was treated. I was the only black/African person amongst all the white people. I wasn’t happy, so i quit but my mother made a big deal out of a $10/hr job. I have no kid or family to feed.

My mother keeos bothering me about how i should have been done with college and start a good job. The thing is that, i just want to finish school and work on project myself but my main passion apart from electronics is politics. But i keep getting bogged down from my mother,. She is always yapping about getting a good paying job, having a house and family. Truth be told, i find it quite boring. A life of quiet desperation.

Thanks for writing this article. Really made my day.

173 Evan Page January 26, 2011 at 5:36 am

I sympathize with this sort of position. Currently I am involved in studies with the goal of Veterinary Science in mind. It was never my initial drive to do this, it was something someone said I would be good at because I cared about animals. At first I pushed it aside, but later on when my circumstances changed I re-thought it over and decided I would do it. It seems like a decent job and something I could be proud of doing. Another thing is that I would be working for myself which is something I do want as I could not stand having to work for someone else for the rest of my life. The problem is I really don’t know if it is what I want to do. It sounds great and all but the passionate drive that most people have in their career goals seems to be lacking. It is exactly as laid out in this article, feels like something I should do. My only problem is I have no other goal or future in mind. Therefor is it safe to say it is okay to pursue this path into something I feel I should do if I have no other dreams or ambitions for a career?

174 Kris January 26, 2011 at 10:31 am

I read the message as if it mean “Stop doing what you think you should and start doing what you want to do.” What a dangerous advice to give out to people!

Count the number of fathers fed up with their children’s crying and their wifes stopped looking as sexy as 10-20 years ago. Should they stay with their families, work on the job to bring food and provide shelter. Should they cope with the teenagers at home if they feel fed up with the obligations of taking care for someone else other than themselves? No, they should choose the freedom to spend their money as they feel fit and not spend it on kids clothes and home comfort — they can actually abandon the life of responsibilities their “should make a family” and “should take care others” false-cirtue shoulds and choose to leave home. Live the life they choose to, not the one they should.

And you begin counting the number of lonely mothers, single parents and children without father. Because apparantly, the message is “Do as you want, not as you should.”

But let me raise against that – A man should do the right thing, A man should choose to do the right thing, even if that means not giving up to that other tempting desire to do what his desires tell him he actually wants to do.”

175 Insomniac January 26, 2011 at 11:53 am

No, they should choose the freedom to spend their money as they feel fit and not spend it on kids clothes and home comfort — they can actually abandon the life of responsibilities their “should make a family” and “should take care others” false-cirtue shoulds and choose to leave home. Live the life they choose to, not the one they should.

Kris, it appears you didn’t read the article. Brett didn’t say that anywhere in the article, and was quite careful to say quite the opposite.

176 Michael January 26, 2011 at 12:50 pm

Brett, this a terrific article. It so clearly defines what our society fails to point out. Men’s life needs to have a purpose beyond the role of provider. A purpose is something deep and meaningful (something we would do for free) and brings us a sense of satisfaction. However we don’t watch talk shows where the host encourages us to explore our feelings nor do our friends or peers necessarily encourage this type of investigation. In America when things are monetized (a law degree, a self supporting blog, a career in banking, being a successful actor or musician) they are celebrated and receive a certain amount of legitimacy. Rarely if ever are we encouraging non paying interests in ourselves or others. I’m reminded of a passage I’m fond of which says something like “when a job or work looks like a mere means of getting money we are still the victims of unreasonable fears.” People pleasing is a character defect (or challenge) I have to as well but if I peal away a layer underneath is just fear. Fear of not getting what (people to like me) I want or losing what I have (financial security). To put it another way my greatest challenge is self-centered fear. The solution to that for me is two-fold: faith and action. I’m not a religious person but I am spiritual and believe that when I pursue being of service to my highest and best use that I am aligned with the greater good. I’m so passionate about this topic I could go on an on about it. I did make a documentary film about choosing a self directed goal instead of continuing to “should” on myself called “How To Become An Action Star in Ten Weeks”- it’s available on You Tube for free just search under the name. It actually led me to finding my wife, who is now expecting our first child, a boy.

177 Chris W January 26, 2011 at 1:53 pm


Read the last 3 paragraphs of the article.

178 John D. Shea January 26, 2011 at 2:05 pm

Great article, Brett! Keep up the great work. I am in the middle of re-evaluating some of my life choices (not including, thank God, my decision to go to law school), and the timing of this article could not have been better.

179 Bill January 26, 2011 at 2:26 pm

Brett, you always make me want to be a better man. THANKS!

180 Ciro January 26, 2011 at 3:35 pm

This article is absolutely breathtaking.
Good job Brett.

181 Cora January 26, 2011 at 4:35 pm

The word ‘should’ has long been one of my biggest pet peeves. I hated the idea that my life was plotted for me and I wanted something different. Despite this intense desire, I still found myself falling into the same pattern, often leading to failure.
Then, on the very day I was set to move up to college to start working for a degree I didn’t want, I toured a school near my home because I wanted to look at their massage therapy program. I’d always loved massage but I’d given in to pressure telling me that it was a fall back job and I could never be successful. After the tour, I knew what I wanted and I was registered and had books within the hour.
I’ve graduated with flying colors and many recommendations and I Should settle into a career at a chiropractic office or health clinic. I’m choosing a job that lets me help others and also pursue my goals in scouting as I work at camps during the summer.
Thank you for saying following your gut isn’t easy. It’s not, but I’m finding out that it Is worth it. A worthwhile, happy life is what I’m working for.

182 Manny January 26, 2011 at 7:43 pm

This site just keeps getting better and better! This article is incredibly moving. I related to it since for years I worked construction but eventually went back to school to pursue my passion, also for teaching. I am currently getting my Masters in Elementary Education and have never felt better. Thank you for choosing to pursue AoM, this site has enriched my life in ways you may never realize!

183 Diego Benavides January 26, 2011 at 10:09 pm


Quería agrdacerte por tu blog, me parece que entrega un mensaje muy importante que lamentablemente se ha ido perdiendo a medida que la sociedad “avanza”, agradecerte porque me ha servido durante este ultimo tiempo a salir de la confusión de la adolecencia y buscar un camino como un verdadero hombre, en fin muchas gracias, desde Chile.


184 Todd January 26, 2011 at 10:22 pm

I think you miss the point. The article is about the pursuit of one’s calling, his singular passion, not about shirking one’s responsibility simply because it’s easier. A man will be at his best as husband, father, family member, or friend when his life’s work is that which he is meant to do. It seems reasonable to me that failing to grow up and “choose” one’s path could lead to a fairly miserable existence and therein make the abandonment of wife, family, and home as a means of relief seem more attractive than it otherwise would.

My dad, who practiced law over thirty years but sometimes doubted a life of letters as his calling, often said that a legal education was the best preparation for life he could imagine. He claimed it imparted both practical knowledge and thinking skills that few other courses of study could. My brother, now in his third year, claimes it simply imparts boredom. I suspect your training will yet serve you well. Thanks for a thought provoking article, and yes, I’ve should-ed myself to many times to count.

185 Michael January 27, 2011 at 12:24 am

I agree whole-heartedly with this article.

I recently came to the epiphany that I should stop “shoulding” and start “choosing” what I wanted to do. After high school I “should-ed” myself into four years of lackluster service in the Navy, even tho I really didn’t want to uphold the family tradition of serving in the military. To be fair tho I did buck tradition as I went Navy instead of Air Force.

After the Navy I once again “should-ed” myself into a crummy, overty stressful job working security at a Las Vegas casino. Why? Because that’s what young in shape males who grew up in Las Vegas “should” do. Three more years down the drain because of “should”.

Now I’m attending college (ASU, my choice) and loving every minute of it. I must say it is very liberating to say I choose to do this and to hell with the lot of you.

Keep up the good work, and damn it keep on “choosing”.

186 Brian January 27, 2011 at 12:51 pm

Very insightful and relevant. Thanks!

187 Josh January 27, 2011 at 6:38 pm


Thanks especially for this article. Your point was so well made because you used your personal experiences to supply the weight of the lesson here. Thanks for sharing so much private thoughts about your career to illustrate thus. More importantly, congratulations – I didn’t know AoM has become a full-time endeavor! That’s wonderful news for you…and us. Keep up the amazing work.

188 Adam A January 27, 2011 at 6:55 pm

Catcher in the Rye (Holden Caulfield, aged 16):

“Lawyers are all right, I guess– but it doesn’t appeal to me,” I said. “I mean they’re all right if they go around saving innocent guys’ lives all the time, and like that, but you don’t do that kind of stuff if you’re a lawyer. All you do is make a lot of dough and play golf and play bridge and buy cars and drink Martinis and look like a hot-shot. And besides. Even if you did go around saving guys’ lives and all, how would you know if you did it because you really wanted to save guys’ lives, or because you did it because what you really wanted to do was be a terrific lawyer, with everybody slapping you on the back and congratulating you in court when the goddam trial was over, the reporters and everybody, the way it is in dirty movies? How would you know you weren’t being a phony? The trouble is, you wouldn’t.

Robert Frost, The Road Not Taken:

Two roads diverged in a yellow wood,
And sorry I could not travel both
And be one traveler, long I stood
And looked down one as far as I could
To where it bent in the undergrowth.

Then took the other, as just as fair,
And having perhaps the better claim,
Because it was grassy and wanted wear;
Though as for that the passing there
Had worn them really about the same.

And both that morning equally lay
In leaves no step had trodden black.
Oh, I kept the first for another day!
Yet knowing how way leads on to way,
I doubted if I should ever come back.

I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood, and I–
I took the one less traveled by,
And that has made all the difference.

189 Zack K. January 27, 2011 at 11:22 pm

Great post Brett!

190 Dimitar Nikolov January 28, 2011 at 8:03 am

There’s something like a “should I do” pneumonia out there – more and more men have forgotten the art of making things happen and have been contaminated by the lack of self-confidence, leaving them wondering about everything each minute of their everyday lives. Quite sad, since part of being a man is being decisive.

Hey, but I’ve noticed that should-ing yourself is a habit much like having the habbit of being productive and just doing what you’re supposed to do. Having said that, the easiest way to get out of it is to just start acting. Oh, and to be sure that what you’re doing is the right thing to do. So, guys, just start making things happen. It’s no big deal anyway, you just have to start instead of wonder.

191 Chris January 28, 2011 at 11:35 am

Great article! :)

192 Chris J. January 28, 2011 at 11:45 am

Great article.

I agree with the totality of this article and think it is well thought out. However, in a business context, (supposing one is already happy with their professional trajectory) I would also opine there’s a fine balance when “Shoulding” while trying to satisfy customers in the short term for a long-term commitment. Temporary concessions to demonstrate commitment to their cause can engender a deep level of customer loyalty. In my experience, customer satisfaction is good, but customer loyalty is everything. Sometimes you “should” do things that are not fun in the short term so you can enjoy the fruits of loyalty, rather than a one-time transaction because going above and beyond isn’t convenient or the customer is difficult at first.

Great article, however. Definitely fodder for the indecisive mind.

193 Rolando Wright January 28, 2011 at 5:19 pm

I thank you for the Anagnorisis. I’ve been stuck for years in both a career i truly am unhappy with, and the dilema of not saying no simply because i never wanted to disappoint. I found that i was doing nothing (and I mean nothing) but fulfilling promises and requests, and taking the focus away from what i wanted. I was doing this because i felt that if I had the power to do something then It would be hypocritical not to. I looked at what i was doing as being selfless. Lately i have found myself saying no, and there is a great satisfaction that it brings. I was shoulding and over crowding my plate, not realizing i was creating a reputation of not being dependable. My older brother would tease by calling me Atlas. Nevertheless, thank you. Your article has inspired some decisions that have long since been stuck on the back burner to come forth. As James Joyce once wrote…”Welcome, O life! I go to encounter for the millionth time the reality of experience; and to forge in the smithy of my soul, the uncreated conscience of my race.”

194 Kingcrowofoctober January 28, 2011 at 10:33 pm

Truly wise writing here Brett. It made me ponder my path. Thanks~

195 Maru January 29, 2011 at 4:30 am

I’ve seen so many things lately that describe my life to an almost scary degree that it is, well, scary.

This is one of them.

It goes to show that even the best people make mistakes. I had thought of you, Brett, as a smart, cool guy who had it totally together. I never realized (but then, how would I?) that you were in a similar position to me: a man living a life of quiet desperation, desperately trying to figure out what he “should” do, rather than what he WANTED to do. And it is beginning to sink in, at long last, that thinking about what I should do is a pointless, fruitless endeavor. No matter how successful I might be doing the things that others think I “should” do, if I do not want to do them, if it was not my own choice, my own will that brought me to them, if I find no joy in them… then really, what’s the point? A man doesn’t lead a life of quiet desperation. He charges forward, ever forward, toward his desired goal. Yamamoto Tsunetomo, the author of “Hagakure,” defined a samurai as one who charges forward without thinking of life or death, victory or defeat, because in that moment, when he has thrown away all thought of his own life to charge towards what may well be a meaningless death, that is when he is most alive and most human. It is a similar kind of bravery that I want to grow within myself, the bravery to charge ahead, to follow my own instincts.

Now don’t worry. I have no intention of charging towards death (at least not yet, heheh), but I do intend to charge towards something that is slowly killing me… that desire to live by pleasing others, constantly worrying over what I should do instead of choosing what I want to do. That wouldn’t even give the pleasure of dying a glorious but pointless death; it would be a half life, a lesser form of life.

It is truly comforting to know that I am not alone in this struggle. Thank you, Brett, for sharing this. I think you just saved me several years that might now be better spent. You truly were meant to be a teacher, Brett; you have taught me a lot already, and you have taught me something very great today. It took you until 28 or so to figure this out, and by your lucid and compelling words, you have communicated it to me (mostly) while I am only 24. I’ll probably fall down a few times more; it’ll probably be a while before I kick that damn should-monster’s ass and whip him into submission. But thanks to you I know his name, I know what he looks like, and I’ll be better able to tell when he comes to bust my ass, so I can turn the tables around on him.

Your wife is an amazing and wonderful woman. I hope I can be so lucky as to find such a woman. I have had the pleasure of becoming friends with three very wise and intelligent women, but fortunately or unfortunately for me, they’re all married or as good as married. Back to the point though, your wife is a wonderful and amazing woman. Don’t ever let her go.

All the best to you and your family.

196 Aaron January 29, 2011 at 9:54 am

As a high school history teacher and football coach I can attest to the general life satisfaction that it brings me, talking about history all day is the only thing I ever saw myself doing. But I have to say the pay is ungodly. We struggle to make bills every month. Makes me want to be a lawyer.

197 Jared January 29, 2011 at 10:50 am

Great article-so much of what I read on this entire website resonates with me and it’s why I continue to return and recommend it to friends.

Important to note is the temptation to “should on yourself” stays with you. Or at least that has been my experience. Right out of college I got a position I wanted in a great school district (I went to school to teach science/biology to middle and high school students). It wasn’t in the locale my wife and I ideally wanted but it was a great job. Ultimately, after two years teaching in what I should have recognized as a great school and position we decided to make the move to the town we wanted to live in. Thinking that with experience but not being too over-qualified, I would be a shoe-in to any position for which I applied.

That wasn’t the case. I had to use the skills I acquired from my Dad and various summer jobs in construction to make a living for the next 5 years! In that time I received my Master’s degree while running a business and growing our family to six! It was tight, very tight. But alas, I finally got back into education in 2009 taking a teaching position about an hour from my house.

Now in my second year with the district I feel that I’m doing what I am called to do. I love my job and I’m coaching basketball to boot. Financially it is still very difficult to scrape by and despite the satisfaction I get in my career, still the “should monster” creeps in constantly. I think often, “I should have never left my first job to live where we live.”: Or, “I should have gone into this or that profession.”

Men, it’s a fight to find your calling. When you do, stick to it. Remind yourself why you do what you do and why you chose to do it. And whatever you do, do it well. Be the best at what you do. Set that standard for yourself.

198 Sam January 29, 2011 at 1:31 pm

All I can say is wow.
I’m in my second year of college now, and I’m so glad I discovered your site. All the articles are so good, and it’s so amazing that they seem to always find me (usually via Facebook) at just the right time in my life. When I first visited your site I expected another one of those oozing-with-pride, narrow-minded “men are better than everyone” websites, but it’s so much different than that. I love how dedicated you are to the topics and how unashamed you are to share true wisdom. You definitely made the right choice when you decided to commit to AoM, because yours are among the best articles I have ever read.

199 Mat January 30, 2011 at 5:07 pm

Great post! Your story mirrors my own in so many ways, it is almost scary. I have been shoulding myself about my career for most of my life, in pursuit of becoming a doctor. During my senior year of college, I considered going the PhD route in something completely different from medicine (religious studies) because I too enjoy teaching. But I told myself to stick to medicine. Then I almost dropped out of med school because I decided it wasn’t for me and there were so many other things I would rather do. Again I the ‘should’ came back and I continued. I am now in Pathology residency, which was the best alternative in medicine for me, and I actually enjoy what I am doing. That being said something is still missing, and I often question why I am still in this profession, despite the prestige and security.

Thank you for this post! This has inspired me to follow some of my other passions so that maybe I can follow in your footsteps!

200 Andrew January 30, 2011 at 10:22 pm

I’m 22 years old and currently planning on returning to school, but quite often I’m torn between what I’d choose and what I should do. This has been quite the inspiring read.

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