The Masculinist #48: Rethinking Career Scripts

Welcome back to the Masculinist, the newsletter about how we live as Christian men and as the church in the modern world.

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I have an article up over at the Federalist about how being a nice guy gets you stuck in the friend zone - and how to get out.

I was a guest on several podcasts this month. The folks at the Endangered Species Podcast (the endangered species in question being the godly man) had me on for a great episode. I loved their descriptor of this newsletter as “observational exhortation.” Related to both this newsletter issue and the one about financial life in the negative world, I recorded an episode with the folks at Abraham’s Wallet.  And I was featured in an episode of the Love Thy Neighborhood podcast all about men, part of a three-episode series they did on gender. Thanks to all these folks for having me on.

On the Masculinist Podcast (subscribe via AppleGoogleweb site), I’ve started my promised series on political conservatives with an episode about how the Republican Party hates your guts. As you can tell from that title, this series is going to be red hot. I guarantee you this series will have information and perspectives on conservatism and the Republican Party that you’ve never heard anywhere else. I include some thoughts on the events of January 6th in the second episode of my series, which covers the founding of conservatism. Thanks to the 132 of you who left ratings on Apple podcasts. Thanks to you, the podcast has a 5.0 star rating. I appreciate it.

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And be sure to check out the Masculinist web site and blog, with new articles posted frequently throughout the month. You might be interested in reading about the normalization of out of wedlock childbearinghow to get started with FIRE (financial independence, retire early), or how to build spiritual disciplines. Some are by me, others by guest posters. So check it out.

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Rethinking Life Scripts

Prior to going into tech, Peter Thiel got a degree from Stanford Law and went to work at a big law firm in New York. He only lasted a short time there. I watched an interview with him a while back (unfortunately I didn’t save a link to it) in which he talked about why he didn’t stay in the law. He said one reason was that he noticed that things were changing in the firm such that his generation of associates would never get as good a deal as the generation before. The previous Boomer generation of partners was pulling up the ladder behind them.

I saw the same thing happen in the consulting world, though I did not get clued into it as quickly as Thiel did. There was a huge and unbridgeable gap between the best possible deal my cohort of colleagues (Generation X) could have ever achieved and what the cohort just five or so years ahead of me (the last Baby Boomers) were able to get. Throughout my career I watched the tide go out in lockstep with each year of experience. I would never get the perks and privileges that someone even a couple years ahead of me in experience got. Shortly before I would have been eligible to be admitted to the partnership, the existing partner base (all Boomers) IPO’d the company and capitalized all the future cash flows that they took off the table for themselves.  (Goldman Sachs went public about the same time, and for similar reasons, although it’s still a great gig to be a GS partner). On the other hand, I was a member of the last group of people to get some leftover perks, such as having an executive assistant. One of the benefits of being Generation X is an ability to know through lived experienced how the American deal changed in the wake of the Boomer generation.

Thiel went on to talk about how there were certain life scripts that Baby Boomers were able to follow that mostly worked pretty well for them. In that era, if you just followed the path laid out for you, things probably went alright. But over time, the level of success you can have from following the script has declined, as he discovered in law and I did in consulting.

There’s a lot of wisdom from older generations that the Millennials and Gen Z have not listened to or taken advantage of. But there’s also a lot of older wisdom that doesn’t work well anymore. Today’s generations need to rethink the scripts that they’ve been handed down.

Career Management in the Negative World

To refresh your memory, I created a model of three worlds of how Christianity is perceived by the culture.

  1. Positive World (pre-1994): Being a Christian is seen as a social positive. Christian morality is still socially normative in society.
  2. Neutral World (1994-2014): Being a Christian is a neutral status attribute. It’s one of many things a person can be in a pluralistic public square. Christian morality ceases to become socially normative.
  3. Negative World (post-2014): Being a Christian is seen as a social negative, particularly the professional-managerial class. Christian teaching is increasingly seen as undermining the new social morality.

The positive and neutral worlds each had characteristic Church ministry and political strategies. The positive world was the era of the Boomercon religious right. The neutral world era was that of the cultural engagers. The negative world has yet to develop strategies, which is part of what I’m doing with this newsletter.

Two issues ago I looked at financial life in the negative world. It was focused on how to restructure the cost side of your life with approaches such as Financial Independence Retire Early. Today I’m looking at the revenue side, the career tracks side of your life.

As with the cost side, on the revenue/career side, there are reasons to be rethinking our approach to out careers apart from the world’s view of Christianity. As Thiel noted, the old scripts just don’t work as well as they used to.

The old script might go something like this: go to college, go to work for a blue-chip company, work hard and move around the country upon corporate command, live in suburbs full of people just like you, retire at age 65 with a pension and gold watch.

This sounds old fashioned, but less than 20 years ago a number of large corporations actually still had traditional pension plans for even white-collar employees. I was a participant in such a plan for a while until it was terminated. I consulted for multiple clients where many employees stayed for life and were able to retire comfortably. That’s not true anymore for most. In a world of large-scale outsourcing and offshoring, a shift to 1099 work and the gig economy, increasing corporate consolidation, etc., uncertainty looms larger than it used to.

Beyond the declining rewards, the traditional scripts come with much more risk today. Consider the 11 students at Northeastern who were suspended - without a refund of their $36,000 tuition - for violating Covid rules. Or the high school girl who had a classmate save a video of her singing a rap song excerpt with the n-word, then sat on the video for three years and dumped it on her university to get her admission rescinded. Feckless university administrators today are practically looking for reasons to stab their own students in the back. With the rewards of society being distributed into fewer and fewer hands, this Game of Thrones style taking out of rival peers by dumping “oppo research” on authorities is sure to only increase as well.

This should be prompting all of us to do a rethink of how we are structuring our careers. I’m going to look at this today in terms of two elements: college and the corporate career track.

To be clear, college is still the right default choice for many. And corporate careers work very well for many as well. I don’t want anyone to think I’m advising him not to go to college or to quit a plush corporate job. But you do have to go into these today with your eyes open and at least evaluate the alternatives.

Rethinking College

I have a three-year-old, and my ambition for him is that he will not have to go to college. I hope that by the time he turns 18, there will be alternative paths for him to launch himself into life without having to spend the time and money that were previously expended to obtain these “launch” credentials.

Let’s be honest, for 95% of people, college is purely about vocational credentialing. They go to college so they can get a good job coming out of it. For most high paying positions today, a college degree is still the price of entry. In some professions, the amount of formal education required to practice is still going up.

But in others it’s changing in the opposite direction. And that change is a good thing, though we need a lot more of it.

Keep in mind that for the Baby Boomers, college was not necessarily a requirement to get a high-level job in corporate America. My step-mother, for example, got married at 17 and went to work as a teller at a savings and loan. Years of work and several bank mergers later, she ended up as an executive vice president of one of the largest banks in Louisville, overseeing all mortgage lending in the state of Kentucky. No degree.

Eliminating the requirement for a degree would just be a reversion to the status quo ante of not that long ago, not some radical overturning of some eternal order.

While a degree is still the default path today, there are a number of alternative paths opening up that are right for some people right now.

One is the famous Thiel Fellowship, which pays students $100,000 to drop out of college and start a company. The fellowship’s account recently tweeted, “In 2011, we gave talented young people $100k to work on something cool instead of attending college. Larry Summers called it ‘the most misdirected piece of philanthropy’ ever. 10 years and 226 Fellows later, Thiel Fellowship projects and companies are worth $70 billion and 99% say they learned more during their Fellowship than they would have in a classroom.”

Obviously you’re probably only getting one of these fellowships if you are pretty elite with a superb business idea. But there are other programs designed to allow people to bypass college and enter good paying employment.

There are a ton of coding type bootcamps, for example. One that’s gotten a lot of press, and generated some controversy to be sure, is the Lambda School, which gets paid via an income share approach. Their CEO Austen Allred is a killer marketer and his twitter account is well worth a follow. He claims some companies are now paying off the income share owed by students as hiring bonus. There are a lot of these coding bootcamp programs out there with various models.

Not all bootcamps are coding focused, however. Praxis is a college-alternative business bootcamp designed to rapidly move participants into employment at growing companies after six months. It focuses on skills like business writing, sales, and content marketing, and many of its students are people from Christian home-schooled backgrounds. If you don’t get a job after successfully completing the program, it’s free. Jon Elordi, who’s been helping out as the managing editor of themasculinist.com is a Praxis grad and has been super-helpful in getting it launched.  (Full disclosure: Praxis is owned by a major backer and client of mine).

None of these bootcamps would position themselves this way, but I look at them as almost an option on the future. If you are high school graduate who does not want to go to college, you can give it a shot with one of these programs. If it doesn’t work to launch your career the way you hope, you can always go to college and just treat the bootcamp as a gap year experience. It’s not like you are taking a huge risk by permanently closing the door to college by going to a bootcamp that’s more aligned with your interests. And if it does work out, which it seems to for most, you not only save a huge pile of money, you get to make a pile over the years you would have spent earning $0 in college.

Again, right now boot camps or Thiel Fellowship type alternative approaches are for the minority. But significantly expanding this to make college optional is one of the great to-dos of our day. I’m personally invested in this as I want my own son to have the option of choosing against college.

For those who do still go to college, I see people choosing new strategies to avoid having to spend and borrow as much money. One strategy is students choosing to start at a local community college, then transferring to a major school to complete their degree. This isn’t just people who are tight for cash either as may have previously been the case. I know at least one multi-millionaire whose kids did it. These folks are figuring out that the only things that matters is the university name on your diploma, not where you took Psych 101. Community colleges now basically have packets that tell you exactly what classes and credits transfer where so that people can readily execute this strategy.

Certainly, even for those who do spend the traditional four years in college, there’s more focus than ever on value for money and graduating debt free. Smart colleges are responding. For example, at Purdue University, president Mitch Daniels has frozen tuition for nearly a decade. He’s also focused on creating accelerated programs to let non-technical majors finish a degree in three years, income share arrangements, and other ways to cut costs and lower debt. Obviously balancing the quality of the school, the career prospects of what you are studying there, and the amount you pay (especially the amount of debt you take on) is important.

Rethinking Jobs

Again, I don’t want to disparage corporate employment. I did it and it was a great experience. And strategies like FIRE are pretty much predicated on people having a fairly high paying job in technology, consulting, or something like that. I think the key for corporate employment is to not get lured into the lifestyle escalator. Instead use that period of corporate employment to gain skills, get a good brand name on your résumé, build a network, and save a bunch of money. Avoid using it to just fuel a hipster consumption lifestyle that traps you. Use your corporate job, don’t let it use you.

Some careers are pretty all consuming. If you go into investment banking, consulting, or law, for example, you are probably going to be working massive hours. That’s just part of the deal.

Most careers are not like that though. Outside of select markets, most corporate type positions don’t come with a big expectation of working lots of overtime. This gives people the opportunity to develop a “side hustle” or incubate a new business.

The idea of a side hustle seems to have taken root among some Millennials such that they just assume everyone should have a side hustle. I’m of two minds about it. If you have a side hustle then you lack focus on your main gig. That’s going to undermine your performance at some level.

On the other hand, having a side hustle allows you to build a secondary revenue stream that reduces the risk that comes from placing all your chips on your day job. It can give you experience working in an entrepreneurial mode, which is a different skill set from working for a corporation. And taking it a step further, it lets you incubate a new business you want to launch.

This incubation of new businesses and careers is something that I’ve done multiple times personally. It’s much more difficult than commonly believed to fundamentally switch careers after you get past the age of 30 or so. I may do a blog post or entire Masculinist on that at some point. Starting off in a new venture as a side hustle lets you build expertise and credentials at a point when you might otherwise be unable to take it on full time.

For me, I started a blog about urban policy while I was still working full time in the consulting space. It quickly became very popular, Later, after I’d won an award for public transit innovation from the Chicagoland Chamber of Commerce, gotten my picture on the front page of the newspaper, and informally consulted with public officials, I felt like I was ready to venture off to try to make a full time go of it. Ultimately that “side hustle” as an urbanism blogger led to an entire second career in urban policy.

The Masculinist of course, is another example of that. It’s a third career, if you will, that I’m still building. But I spent four years on it (and multiple years of research before that) before it became my primary gig.

Obviously these aren’t totally separate. Although the domains are different, they build upon layers of skills that I’ve built over the years, going back to some things I even learned in high school. And each thing I’ve done has allowed me to add to my collection of skills that benefits every domain of professional life, which is another benefit of side hustles. Side hustles helped me build my talent stack and expand networks of people I know into many other domains.

Having taken on multiple side hustles, I’m obviously a fan. But I would encourage you not to underestimate the risks and downsides of dividing your focus. From a purely professional point of view, I would probably have been better off financially by never taking on any side hustles and simply doubling down with all my energy on consulting.

I’d also encourage you to do your due diligence on intellectual property ownership. Most corporate employers shove a pile of papers in front of you on your first day to sign. One of them probably assigns the company all IP rights. These agreements are typically extremely one sided and not infrequently egregious. I’ve read some that claim ownership of everything you produce, even on your own time and on your equipment, meaning that technically they claim to own the IP to your personal family photos, your Facebook page, etc. I heard that colleges often claim they own anything students create no matter when, where, and how they do it.

I’m not a lawyer and I doubt you can afford one for this, but reading and understanding what you sign is important. Rules also vary by state. You might want to network with your local tech entrepreneurship community to get a read on the situation where you live.

The next step beyond a side hustle is of course business ownership. You can either start or potentially buy a company. A deep dive on entrepreneurship is beyond the scope of this post. But you should understand the economics of the business you want to get into, and look for something with significant upside. Too many businesses come with high risk but little reward even when successful. Most of these are passion businesses, like restaurants. There’s nothing wrong with that, but you should be aware of what you are getting into.

If you want to escape the political constraints of major corporate America, you probably also need to avoid creating a venture capital funded business, a government contractor, etc. The best kinds of businesses are so-called “lifestyle businesses” that don’t have venture fundable economics, but still create significant possible scalability.  This could be a technology company grown organically using the Basecamp model, for example. But it could be a much less sexy business. Years ago, for example, self-storage companies were extremely good investments (though that may no longer be the case).

If you start or buy a business, obviously the due diligence is on you. And not everybody has the skills or psychological orientation to succeed in running a business. But business ownership is one way to escape some of the political constraints of the mainstream business world today.

Finally, I’ll just mention that some people are increasingly touting skilled trades, some of which have labor shortages, as an alternative path. For those who like to work with their hands, or outdoors, or in other ways besides traditional office work, this could have an appeal. I don’t know enough about this to say more, so do your own due diligence.


While the traditional professional track of going to college and then to work in corporate America is still the right choice for many, increasingly today that comes with possible downsides (like debilitating student loans) and risks (such as being attacked for some kind of political transgression).  Christians and non-Christians alike may want to consider whether alternate structures are right for them and their children.

This could include rethinking college such as by going through a bootcamp or other alternative credentialing system. It could also include pairing corporate employment with a savings regime like FIRE, starting a side hustle, or going into business for yourself.

These alternative approaches are not right for everyone. While they are suitable only for a minority of people today, hopefully they will expand in their addressable market over time, especially enough to remove the general requirement to get a college degree in order to obtain a well-paying job.

Too many young people today are massively overburdened with student loan debt and stuck in some corporate salt mine trying to pay it off. It’s incumbent on people coming of age today (and their parents) to figure out how to keep that from happening to them.

Positive Family Stories

There’s a ton of negative news and bad stories about American men and families today. As I pointed out in Masc #28, the grim contents of so many Christian marriage books can be almost enough to make a single man decide to hold off on getting married for a while.

But there’s a ton of great things about family life too. Back in 2019 I posted reader submissions of great family photos or stories designed to show the joys of family life. Reader Joel wrote to me with this family picture and story to tell.

He writes:

My family trekked up to higher elevation last weekend here in Arizona and harvested a Christmas Tree. It was a family affair including a nice picnic in the crisp, quite cold, mountain air. We hiked around for about 40 minutes before snagging our tree. After loading the tree up on top of the truck I set my phone on our little camp table for a quick snap, and it turned our great. I tinker with and restore old Land Cruisers on the side and this photo captures a happy synergy for me… combining family time with the fruits of my automotive competence.

I want to keep showcasing the good in marriage and family, so if you have pictures or stories to share, send them my way.

The Junior Classics Podcast

Another thing I want to do more of is cross-promoting the work of Masculinist readers and others that may be valuable to some of you as well.

Bradley Hasse is a Chicago area Masculinist reader I met at one of my get togethers there a few years ago. He created an interesting podcast out of children’s stories called the Junior Classics Podcast (web siteApple podcasts). The Junior Classics were a ten-volume series of stories published by Colliers in 1912 that included volumes of fairy tales, heroic stories, nature, poetry, etc. In other words, classic, traditional, wholesome stories for youngsters.

Hasse’s Junior Classics Podcast includes high quality spoken word storytelling of these classic tales, plus vocabulary words to learn and a summary of the moral lesson of the stories. His goal is to instill a love of reading in children. If you have kids, this is one to check out.

Reading Recommendation: The London Review of Books

Several people have asked me to put together a reading list. That’s very difficult to do for a variety of reasons. Different people want different things. Some want a list of books with practical “how to” information. Others want more intellectual or scholarly depth. You can’t create a one size fits all list. Also, some books that I’ve found valuable are hard for me to recommend for various reasons. Charles Taylor’s A Secular Age, for example, is 900 pages long and extremely dense. I once led a yearlong discussion group of just that book. I’m very hesitant to recommend massive tomes like that, although if you are interested in it, you can download my notes and study guide as a free resource.

But I will think about putting together a list. In the meantime, I’ll start putting out ideas for those who may be interested, similar to how I previously recommended the books of Nassim Taleb, especially Fooled by Randomness and Antifragile. You can also download my notes on Taleb’s books as a free resource to you.

My recommendation today is actually not a book but a literary magazine: The London Review of Books. The London Review of Books has been called the best magazine in the world and I agree.

The LRB is for those of you with more intellectual inclinations. Issues arrive roughly fortnightly, and are full of super-interesting articles. The non-fiction books are reviewed in such depth that you get an excellent précis of their contents such that you don’t have to actually read them. That makes the LRB a powerful force multiplier in your annual reading. I also appreciate that how reading articles such as a review of a biography some obscure figure helps remind me of how much I don’t know, and how much that’s out there that I’m not even aware of not knowing. That’s really important in keeping a sense of humility about what we think we know, or the limits of our own knowledge.

The LRB is a magazine of the left. The readership of the Masculinist skews conservative. For conservatives, the LRB is especially helpful as a reminder that the left has a lot of very smart people – in fact, way more smart people, and often smarter people, than the right does. American conservatives consume a lot of left leaning content, but it’s typically either a) pure-play activism like say Rachel Maddow or some twitter provocateurs, or b) unimpressive middlebrow cant like The New York Times. This can leave a misleading impression of the left’s intellectual depth.

Not every article in the LRB will impress, but when you read, say, Perry Anderson on Bolsonaro’s Brazil, you realize that he knows a lot more about Brazil then you or I do. I’ve previously linked to some articles in this newsletter before, including James Meek’s look at Cadbury’s move to Poland (which included some interesting commentary on Quaker businesses) or Yun Sheng’s diary piece on husband shopping in Beijing.

The big downside of the LRB is that you can never keep up with the reading – it’s too much. But if you’re an intellectually inclined reader with an omnivorous interest in topics, the LRB is a great one to subscribe to.

Speaking at subscribing, if you aren’t already a financial supporter of the Masculinist, please consider becoming a monthly backer on Patreon or Gumroad, or send a one-time donation via PayPal or by mail to: PO Box 33171, Indianapolis, IN 46203.


This [eugenics, forced sterilization in Western nations] occurred on the basis of this research, under state auspices, pushing back the boundaries of what the state was and could be: the concept of public health goes back to this period, for the idea that the state should be responsible for the health and well-being of the individual is by no means a given, and its attendant notions of healthy minds in healthy bodies, of poverty and darkness and poor health being swept away as the sun shone in on hardship and abjection, which then would jump up invigorated, of poor children being sent to the countryside in the summer, of health visitors and vaccinations, were all about the conjugation of body and state. And it was carried out by decent people with decent intentions, the thought that it might be wrong to sterilize a woman suffering from delusions and unable to look after herself being not at all obvious, since there was a risk, if she became pregnant, that she might pass on her affliction to the detriment of her child, and thereby also burden society as a whole.

- Karl Ove Knausgaard, My Struggle, Book Six

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