5 Things I Learned From Penelope Trunk

Alexander Yolevski
5 min readApr 30, 2013

Last week, I was given the great opportunity to have a phone call conversation with the blunt, straightforward, and undeniably helpful, Penelope Trunk. She is the founder of Brazen Careerist and two other software startups. Her claim to fame includes her career coaching services and tremendously popular blog, noted as the most recognized career blog on the internet. I wanted to get an insight of her opinions on finding a career you love, pursuing a meaningful career, and a few other things. Here’s what I got out of it.

1. “People are successful because they are good at what they do, not because of their degree”.

Trunk explained that people become successful because of their skills, interests, and their ability to be great at what they do. You are not successful because of the piece of paper given to you after years of studying. For example, a social worker who opens up their own practice becomes successful because they are good at what they, they have the ability to brand and market themselves, they can attract clients and have other entrepreneurial related skills as well. It has nothing to do with their degree. In fact, she said anyone can become a lawyer too… without school. You can teach and educate yourself on the required knowledge and begin marketing your services to others. As per state or provincial law, you may not be able to use the title of a lawyer or its corresponding letters, but you can act as a law consultant etc. Nevertheless, as long as you have a service that people want to purchase, you can become successful at what you do.

2. “To do what you love, you need to take risks”

If you don’t work those jobs that make you miserable, or the ones that require sacrifice of some sort, you will never be able to discover what you hate and what you love. You need to do “stupid things” or else you won’t be fully exploring your options and possibilities. If you want to do what you love, you first need to be good at it. Next, you need to recognize whether or not people will be willing to purchase your goods or services related to what you love. If you can’t do what you love as a career, do you what you are great at and do what you love in the evening. “Everybody has four hours at the end of the day, after work to do whatever it is they want. Most people choose to watch television”.

3. “People don’t need permission to do anything”

Trunk strongly emphasizes that nobody needs to be allowed to do or be anything. You simply need to be great (better than good) at what you do and have something people are willing to purchase. Trunk is one of North America’s most popular career consultants (or therapists, or advisors, whatever you want to call her, regardless, she’s worth $250 an hour **update: now $350 an hour** to get personalized advice from her), and she does not have a Masters in Counselling, Psychology, Guidance or anything like that. She simply recognized that she was great at giving career advice, people wanted to pay for more, and she enjoyed it. That’s all. Nobody can tell her to stop giving advice, or stop “acting” as a therapist or guidance counsellor of some sort just because she doesn’t have certifications backing her up; her clients and satisfaction rates back her up. It doesn’t matter. She is good at what she does, and people benefit from it.

4. “Anyone who takes a loan to go college, has what they deserve”

It is no secret that Trunk isn’t too fond of the education system, more particularly, post secondary degrees. She insists that college is a waste of money, and there are more valuable and efficient ways of spending your money and getting ahead in life. Trunk suggests that for both students who pay for their own school, and parents who pay for their child’s education, the money should be put towards a company rather than school. In Canada, however, she addressed, that because university is “essentially paid for by the government” in comparison to the United States, people may go to school to be independent. In a nutshell, it is ridiculous to shell out money for a degree. Develop or invest in a company instead. If you fail with your first company, you will at least be left with more skills and experience than you would have with a university degree. “Nobody needs a core curriculum. Everyone learns on their own, whether they know it or not.”

5. “Use school for internships and free living”.

Trunk recently wrote that high schools should incorporate more internships and co-op type programs. During our conversation, she stated that people who can afford to go to school without taking a loan, or have their parents paying for them, or live in Canada if anything, should attend school to take advantage of all the affiliated internship opportunities that universities and colleges provide with exclusivity. In fact, she elaborated on this and suggested, in a humorous but somewhat sincere tone, that we should go to school, pick the easiest courses, decided on the easiest major, just barely pass each class (which you can do by just taking the final exam), and become involved with as many internships as possible. This way, not only will you get your piece of paper, but more importantly, you will have a resume of quality experience that will actually help you get a job. In addition, students are able to achieve “free living” and explore an independent life of some sort when their school is paid for by their parents.

Penelope Trunk is known to be radical with regards to her career advice on opinions related aspects such as finding a job, pursuing passions and education. However, she calls is as it is, is GREAT at what she does, and maintains a tremendously popular and inspiration blog at www.penelopetrunk.com. I thank her again for taking some time out of her busy schedule to chat with me over the phone.

Originally published at www.yolevski.com on April 30, 2013.



Alexander Yolevski

I help entrepreneurs create discoverable online content that builds trust, generates income, grows an audience, and establishes a future-proof business.