Interview with Penelope Trunk - Unconventional and Uncomprimising

Recently I had the chance to sit down with entrepreneur, author and blogger Penelope Trunk. Known for her blunt honesty and no-bulls*%# advice as well as unconventional wisdom about life, women in entrepreneurial roles and people starting out in their careers.


Before I go on I should say that my conversation with Penelope was both educational and eye-opening. I was surprised to find myself on the opposite side of many subjects. Her advice is blunt, unconventional and even seemingly counter-intuitive. What follows are the main points from our conversation.


Before you dive in....Take a listen to the episode first! 

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Unconventional Advice #1: Social media sites like Facebook are a detriment to authenticity.


When asked if authenticity was on the rise, Penelope pointed out that social media sites such as Facebook generate a certain degree of pressure for users to show their positive and engaging lives, even when they aren't. Because of this bias toward positivity (real or not), users who are not happy tend not to say anything at all, reducing the overall level of authenticity.


Unconventional Advice #2: Writing must be a means to an end - something to sell.


Being a writer means always working toward something you can sell. Penelope has always made money through other avenues and as a result, she believes that writing does not generate sufficient income to support a family.


Unconventional Advice #3: Trying to be remarkable leads to too many trade-offs.


Our society seems focused on being remarkable in our work and daily lives. Penelope believes that no one has a 'greater purpose' in this world.


The truth of the matter is most people are not remarkable, and those who are are people you would not want to be around. The sacrifices that need to be made in order to be remarkable are limited to, as she puts it, "stark raving lunatics."


Social media also pressures people to stand out and try to be remarkable. As a result of all this, there's a pretty big disconnect between the supposed goals that people have and what it takes to reach those goals.


Unconventional Advice #4: The pressure to be remarkable is too great - particularly for women.


The pressure on people to do something remarkable can lead to tremendous disappointment, especially for women in their late 20's, many of whom are considering starting a family. As Penelope puts it 

Everybody has just really basic wants for their world. They want to love and be loved and have a family and have security and have an interesting job.


Unconventional Advice #5: Society has more respect for mainstream, unremarkable people.


By the time people are 40 they have a spouse and children, and very few are millionaires, and even fewer are working the ridiculously long hours most entrepreneurs are forced to work. Once you reach the age of 30, avenues begin to close off.

“nobody wants 30 year olds in entry level jobs - so tons of things are closed off to you.”
— Penelope Trunk

She believes that our society has a great deal of respect for making mainstream decisions because people cannot really function as a 40 year old outside the mainstream.


Unconventional Advice #6: Generally speaking, remarkable people are driven by despicable moral values.


Using examples such as Martha Stewart, Bill Gates and the late Steve Jobs, Penelope pointed out that people who do remarkable things are usually found outside the ethical mainstream.


About Jobs she said, "While he was doing all the things he was passionate about he had a kid that he couldn’t support."


When talking about Bill Gates, she explained how he spent much of his time selling something that didn't exist. He didn't know how to build it, but told people it was done. She went on to explain that only a very small percentage of people can sell something that doesn’t exist and that she is one of them.


Moving on to Martha Stewart, Penelope said that she had coached many women entrepreneurs who wanted to be the next Martha Stewart. She believes that to build a brand such as Martha Stewart's you have to give up being a parent, because the demands are simply too great. Sadly they don't take into account the sacrifices that have to be made to achieve those goals.


Unconventional Advice #7: Baby boomers' competitiveness is a key factor in the desire to be remarkable.


Baby boomers are far more competitive than millennials, and as a result, they push their kids to be remarkable, to live outside the mainstream. However Penelope does not believe that most people are comfortable living outside the mainstream. She went on to say that one of the biggest risk factors in divorce is being an entrepreneur.


Unconventional Advice #8: Personal development doesn't take into account families.


At this point in the conversation, Penelope went into what she called a 'tirade' about personal development practitioners. She pointed out that the material assumes that people have one guiding value - one thing that is extremely important to them. Because of this, successful personal development practitioners such as Steve Allen and Kim Seres do not have kids, do not talk about serious relationships, and don’t take care of ageing parents.


She believes they don’t have anything to be responsible for except generating personal development advice for people who don’t have anything else in their life. She concluded by stating definitively that what is needed most is a sense of honesty in creating personal goals, not by looking to people with remarkable lives, but people with stable day-to-day lives and working toward that goal.


Unconventional Advice #9: Entrepreneurship is NOT the key to having it all.


When I pointed out that much of the purpose of my podcast (and this blog) is to show people how they can use entrepreneurship to 'have it all,' Penelope expressed tremendous shock.


She pointed out that entrepreneurs work longer hours than anyone else, and that even people with big jobs can only 'have it all' by having nannies to care for your children.


Of course, nannies require much more income, and the easiest way to build that is by climbing the corporate ladder.


Penelope then went onto explain that the people who get to the top of that ladder fall into a specific personality type - ENTJ. This refers of course to the now famous Myers Briggs Type Indicator, of which there are 16 personality types. ENTJ is sometimes referred to as 'The Executive,' and is thought to be a born leader. She pointed out that only 2% of the world's population are ENTJ, while 100% of Fortune 500 CEOs are of this type.


You can find out your Myer-Briggs score on her site Quistic 


She also cited an article in the New York Times about women entrepreneurs who bring their kids to work, pointing out that all of those women had husbands who funded the company and the day care.


Unconventional Advice #10: Raising multiple children as an entrepreneur is impossible.


When I brought up the example of Jayson Gaignard from Mastermindtalks who is a successful entrepreneur and has a small child, Penelope pointed out that he would not be able to support multiple children with such a business, mainly because the income is only incremental.


She explained that if you work full time, have 2 children and have a lifestyle business, then it isn't really a lifestyle because the business takes away from your family time.


Unconventional Advice #11: You cannot judge the quality of someone's life by what you see on the surface.


On the subject of career advice, Penelope offered this piece of wisdom, "Well people aren’t very honest about what their life is like, right?"


She explained that unknown to most people, Sheryl Sandberg has round-the-clock nannies for each of her children and has them go to her sister's house every night for dinner. Because she doesn't talk about that, many believe that her life is one to aspire to, when in reality, it's quite different than the one publicly on view.


She also stated that she did not know of any family who truly wanted both spouses working when the kids were 12. The reality for her is that people have to show up somewhere and do things they don’t like to do, so they can get paid enough money to support their family.


Unconventional Advice #12: Being a changemaker is 'bulls*%# aspirationalism.'


Penelope's point of view was, as you can imagine, an interesting one for me. When I asked her what the word 'changemaker' meant to her, I received a typically straight-to-the-point reply. I'll let her explain in her own words:

“Bulls*%# asprationalism. What really matters? At the end of your life what matters? Does it matter that somebody thinks you instigate change? I don’t think so. I think it matters if you can create stable fulfilling relationship and have an interesting life, and I think most people don’t require change to have an interesting life.”
— Penelope Trunk

She then went on to ask me if I needed change to create an interesting life, pointing out that you don't need to make change in the world, it happens to you. She finished up by explaining that what people want stability in a world of change.



As you can see, Penelope’s advice is as uncompromising as it is unconventional. Quite often it’s beneficial to talk to people who challenge our deepest beliefs and assumptions. Respectful disagreement and intelligent debate can open your eyes to new insights, or strengthen opinions you already held.


So...What are your thoughts? Agree ? Disagree? 


I’m really glad to have had the opportunity to chat with her, and I'd love to hear your thoughts on some of the topics we discussed


Let me know in the comment section below!