This Woman Just Changed Your Whole Career Plan

penelope trunk
image courtesy of eschipul

No one has influenced the way I think about career like Penelope Trunk. Not even close.

Her ideas are so big and so smart, and she manages to kill my dreams and inspire me in a span of two minutes, while covering the same topic. Penelope’s changed everything I thought I knew about professional life.

As I brainstormed key takeaways from her work to include in this post–originally intended to pay homage to all her views that have had an effect on me–I realized there’s no way I’d be able to highlight the many lessons learned and insights gained from hours of browsing her archives, and decided to categorize them.

These are the career-related ones.

Don’t Go to Grad School

My newsletter subscribers know how tough this message is for me to accept, as just a couple of weeks ago I shared with them a gigantic meltdown I recently had about academia. The gist: I had compiled hours of research on my personality and talents (because my quarterlife crisis is totally not over. Yay!), presented it to John, we both very clearly saw academia as the best career path for me, and then almost immediately realized it was a completely unrealistic goal due to life circumstances that are beyond the scope of this post. And I took it hard.

But maybe I shouldn’t be so upset–Penelope argues that in general, working toward anything more than a bachelor’s degree (and maybe even that) is a waste of time and moneyIt’s not like higher education institutions have a stronghold on all the world’s information, and if you’re looking to learn more about something–pretty much anything–you can learn it for free by picking up a book or doing research online. How many employers would love to hear that? “No, I didn’t go back to school, I just know all this because I’m ambitious and disciplined enough to teach myself.”

Related, while your main role in life is a student, and you’re spending so much time studying, you’re not exactly stacking up what employers truly care about: achievements.

Now, if your intended career exists in academia itself, then yeah, it makes sense to get an advanced degree…except it doesn’t, because there are no jobs in academia.

Don’t Listen to People Who Laugh at the Words “Quarterlife Crisis”

When I acknowledged I needed to make a career change, and subsequently realized I had no idea what to do, I felt like I was dying. What made it worse is that I felt ridiculous and alone–I thought everyone else had their shit figured out. At least way more than I did.

I was introduced to the quarterlife crisis concept on Penelope’s blog, and felt so much relief. I later used the term in a conversation with a middle-aged man who laughed so hard at the idea, and, because of the knowledge I now had, it didn’t upset me.

Don’t Freak Out About the Possibility of Being Fired

I’ve mentioned before that I have a history of ending up in jobs I should be fired from. You know how this makes me feel? Stressed beyond belief. And BROKEN.

Actually, it used to make me feel broken, until I read about Penelope being fired from a lot of jobs, and her friend Melissa being fired a bunch, too. And then I thought, maybe I’m just part of this subset of people who aren’t good fits for most jobs. Plenty of successful people have been fired before. The universe will find a place for me.

EDITED TO ADD: There was another section right here, but I deleted it. It was about women and work–a topic I’m still feeling my way around–and what I’d written suggested something I didn’t mean. I plan to revisit the subject in the future. Apologies to anyone who was offended; my intention was actually the opposite.

Don’t Do What You Love

I’ve come back to this post of Penelope’s over and over again, because it’s so radical, and without the information in front of me, more popular messages skew my thinking. (Another example is my initial resistance of following the Paleo diet. ‘But how could we have been told so often for so many years that grains are good for us is they really aren’t? But the fiber and the nutrients and…’ Eventually, you find truth, and the more you expose yourself to it, the more it sticks.)

So we’ve been told to follow our passion and make the thing we love into a career. And Penelope and others are trying to tell us that’s poor advice. The idea is that it’s dumb to think we should be paid to do what we love, because we’re already doing it. For free. Because we love it. Not only that, but also when you make it your work, it starts to suck. You have to start making compromises and tough decisions and thinking like a businessperson instead of just enjoying your hobby, and you suck the love right out of it.

So the better option is to do what you’re good at, and what will help you achieve the lifestyle you desire. And keep the thing you love untouched so you keep loving it and have a nice free time activity.

I agree with all this, but I think it’s very complex. For example, pretty much everything I care about and everything I’m good at is represented in my role as a blogger. So it isn’t easy for me to identify some other skill I possess that I don’t use to run this site, and find a job that uses it, because my talents and interests are all at work here. Part of me thinks I should make this my career, because look, there is no better fit. The other part thinks I’d end up hating this thing I love if I do that, and I should find something unrelated.

Clearly, I’m still sorting this one out.

Don’t Dismiss Alternative Career Paths

Penelope’s entire approach to career is unconventional. She challenges things we all just accept to be true, and points out flaws in common ways of thinking. I realized shortly after John introduced me to Penelope’s work that I could define “career” however I wanted. I could call being a mother my career. I could call a series of random jobs my career. I could spend 40 hours a week doing work that’s fine and say it’s my job…but actually call blogging my career.

A career can be a messy mish-mash of roles, projects, and experiences. Likely, it should be. And really, following a traditional path can majorly delay your success.

I guess overall, the theme of everything I’ve taken away from Penelope’s writing is that we’re screwing ourselves by failing to challenge “rules.” And hey, that’s what the Alternative Badassery philosophy is all about!



Who has influenced your notion of career? What’s some unpopular advice that’s helped you?

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Your thoughts?
  1. Austin says:

    the topic on grad school is really relevant to me right now. i really enjoy the career/job/whatever you’d like to call path i am on right now, but i get a sense that i will not be able to make it to the next tier without an mba. after doing a lot of researching, i completely agree that you can learn just as much, if not more, self teaching yourself everything you need to know. the problem is how to convey that potential employers. as ignorant as i think it may be to require an mba to even consider a candidate for mid-senior level positions, the majority of companies still do it. convincing some drone recruiter who is programmed to look for requirement X, Y, and Z that you know more than your typical mba student is going to be pretty difficult to do.

    • Cassie says:

      Really, really good point. I think a way around this would be connecting with people already in jobs you want, and getting their advice on the skills and experience *actually* needed to be successful in the role. And so the idea would be that you work to attain and develop these while simultaneously building your network, and then you get the job you want by leveraging your connections and demonstrating you have a full understanding of the job requirements and have been working independently to build yourself into the ideal candidate. Bypassing the gatekeepers who are only going to compare your on-paper candidacy to their list of criteria (and who may know very little about the job itself anyway) would be key. I do think MBAs *could* be an exception here, though–as in, I can see how the investment might actually be worth it in terms of what you’d learn and the experience you could gain. Either way, great comment!

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