in: Advice, Character, Featured

• Last updated: September 25, 2021

Don’t Should All Over Yourself

Vintage man scratching head illustration.

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?

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