Silkarmour Boardroom In Conversation With Penelope Trunk

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Introducing one of the most popular career advisors on the internet and one of TechCrunch's list of 30 Women Revolutionizing Tech –the irony being she lives on a farm in the middle of Wisconsin.

The hidden reason women are held back, the importance of trial and error and why Penelope decided to become a stay at home breadwinner, according to Penelope Trunk.

Penelope Trunk in Conversation with Silkarmour Boardroom
For Trunk, who was once a professional beach volleyball player, moving into the world of entrepreneurship was a decision fuelled by curiosity and the age-old approach of ‘picking yourself up and trying again’. Her first ventures in start-ups were ECityDeals and, a maths-tool resource for the teaching community, which was funded by Encore Software. Her most notable pursuit however is co-founding BrazenCareerist, an online career management platform for the next generation of professionals. What BrazenCareerist does differently is allowing its members to highlight their ideas within the workplace and towards their own projects, to depict a more personalized impression of themselves; something beyond a person’s black-and-white credentials. 

What’s more, Trunk took her thinking a step further in gearing the site to encourage communication within its community, allowing networking to evolve through conversation. Today, Trunk runs her co-founded company Quistic, providing online courses to help manage said career progression. Having gathered all her experience and flogged it in a best-selling career-advice book, ‘Brazen Careerist: The New Rules for Success, it’s safe to say she knows what she’s talking about. 

But not everyone agrees. True to form in the age of the internet and the freedom of speech it brings, Trunk’s honest and candid approach to guiding people through their careers attracts as many critics as it does fans. Starting out at Fortune Magazine where Trunk shaped her bold and vivacious tone which expanded to guest writing roles at Business 2.0, BankRate and Yahoo Finance, She is now known, and equally divided in popularity, for her articles on TechCrunch, the verified ‘gospel of tech’ and her own website, Racking up 1 million monthly readers - and a slew of comments to follow – Trunk’s abrupt headlines lure in readers for the click-bait but hooks them with advice on career management, personal life, the complexities of being a working woman and sometimes, the verbal backhand we need to stop whining and just get on with the task at hand.


Trunk grounds her readers in the competitive rat-race with brutal, practical honesty whilst approaching some of the most relevant and progressive issues in both men and women’s careers.  In an equally frank discussion with Silkarmour, she disclosed her attitude towards modern education, the sacrifices that need to be made for a career and her lessons learned from failure.

Penelope Trunk Silkarmour Boardroom Conversation

You’re an incredibly accomplished writer, what do you believe were the most important factors in your success?

Well, I think in order to get to be in a place of power, you have to really know yourself, because of the incredible commitment it takes. In order to be that committed to something you have to really understand your priorities, so every time you miss out on something else, it make sense to you. I think, especially for women, because women are not as singularly focused as men - typically they are juggling a lot of things. The women at the top, you can see they have thought very hard about who they are and where their priorities lie. 

And what was your process in deciding what your priorities are for you? 

I think trial and error.  I started out as a professional athlete, playing beach volleyball. Then I realized it was really boring; so I just kept trying things and if they didn’t feel right for me, I would try something else. I think my willingness to fail and fail quickly and do it again is what allowed me to be successful but there are also some really huge failures like my second start-up. I got kicked out of the start-up, ended up losing a lot of my own money and I felt really terrible and embarrassed. But when I looked around, I saw that it has happened to others, lots of people have the same kind of experience, but they spin it like they’re God’s gift to entrepreneurship; so I just started re-framing things. I think that was really important and I don’t think many people are willing to say that they failed, publicly, over and over again unless they have learned how to present those failures in a way that shows how they have grown because of them. 

"I just kept trying things and if they didn’t feel right for me, I would try something else. I think my willingness to fail and fail quickly and do it again is what allowed me to be successful"

You have very vibrant comment threads; how do you deal with so many people with so many things to say about you. How do you brush that off? 

I do live and die by my comments. People say ‘Oh Penelope has so many comments, she doesn’t read them all’ but if I don’t get many comments, I have a bad day. Some people have bad days; I have ‘no comment days’. If people think I’m stupid, they take the time to tell me I’m stupid - to me, that’s an achievement because they care enough to pay that attention to what I've said and also because it had an impact on them, raised an issue in a way they haven't thought of perhaps. 

You don’t fear what other people may think is right but you get validation from what you do and how much people appreciate it. Do you think that’s important in keeping your sanity?

This may also be the problem - I’m doing this big career but I’m also raising my kids. I just had to yell at my kid, I’d have more patience if I weren’t working now and weren’t taking a million calls. 

Do you really think that’s a bad thing for your kids, the fact that you’re working?

I don’t think it’s bad for them; I think that I miss out. I just had a moment where I could connect with my son and show him empathy - in my fantasy life, that’s what a good mum does, uses an opportunity to connect with her kids. But I’m not very empathetic anyway; I have to work really hard at it. It’s fun to talk to someone interesting and it’s not fun to have to connect emotionally with a whiney hungry child, honestly, so I’m always torn.  I wish I could find my kid as interesting as I find you asking me questions about how women manage themselves. 

I feel, as a mum, this is a special part of life. I’m going to be alive, let’s say for 80 years. I get 15 years when I’m the most important person to this kid and they like, just want to be with me so much and I can enjoy that time. Or he can be independent and he’ll be fine but I think that I want that experience of having such a closeness each day because when he’s 17, he’ll be saying things like ‘Mum get away from me’. I don’t want to miss it as it’s so short. 

"I want to hear that from everyone, I want Sheryl Sandberg to tell me what she gave up, I want Barack Obama to say ‘here are all the things I gave up to be President’. Everyone should write about that all the time; that is the only honest thing to write about"

It sounds like there are no good options for women; it feels very unfair because men don’t have anywhere near as hard of a time with balancing work and family. 

Here’s the problem I see;  most educated women are married to a guy that will make enough money for both of them, so most educated women with kids are working because they want to contribute something big - but, people don’t do big, important things, part time. No one does. There’s actually a lot of talk about women who are at four days a week and they’re getting paid part time but they’re working full time and it’s a terrible deal, it’s like slave labour.

On the the other hand, I think it is fair, because if you’ll commit 100% to your work, you’ll get to work with other people who will commit 100% and people who commit 100% do amazing things. But the problem is that we raise girls telling them the reason they go to school, is so they can go to a better school, to get a better job in order to do something big with your life. People tell you your purpose is to come to school so you can do something big when you grow up, you hear phrases like ‘You’re such a smart girl you’re going to go to college and do something really big after college.’ 

Isn’t this really unrealistic? Why do we have to spend 18 years or more preparing to do something big when very few people want to devote their whole adult life to that. Honestly, I think the problem is school because we sell kids a really raw deal and women don’t need it - they’re going to be pissed off when they find out they’re going to work part time and they’re going to have kids. They’ll spend 18 years doing school really well only to work part time because they have kids. Why are women working so hard in school? Why don’t women go into the workforce when they’re 15? Men have all this time to do work, and young guys waste all this time in their twenties, because they have all their thirties to do work and women are under the gun in their twenties, so why don’t we just let women enter the workforce earlier? We’re just holding women back.  

How would you do that? How would you change the system? 

I took my kids out of school so I could be an advocate for it, especially for girls. We already know you can’t teach someone to run a company in business school, which means you don’t need to go to school to learn how to run a company. Kids should just start doing cool stuff they’re interested in. There’s an incredibly large amount of research that shows that kids will learn anything up to algebra in maths on their own; so I did that with my youngest kid and it worked. There’s a lot of research that says educated parents don’t need to teach their kids to read, they’ll learn it on their own. The reason we don’t publish that research is because we wouldn’t know what to do with the kids that don’t need school. We will literally not know what to do with them and just want to send them out of the house. It’s so insulting to people, to be told that they need to learn stuff. Everyone will find something interesting to do and learn a lot as a result of the doing, it’s the human condition.

Penelope Trunk techcrunch

 What advice do you have for women who want to change careers?

Since you know you are going to have multiple careers in your life, changing is not high stakes. Don’t make a huge deal about it and don’t spend five years searching your soul. Just start testing the waters - put a toe in the current to see how it feels. Then take a leap, and if you don’t like where you land, reframe your landing pad as just a stepping-stone. And start putting your foot in the water again. 

For you personally, if you had you’re ultimate life, what would it look like?

A rich husband! But I would want him to be rich from something he’s really good at. I’d just be able to do Pilates, I would want a Pilates and yoga instructor living with me, so they would force me to do it every day. I would take care of my kids and then when my kids get older, I would take my husband’s truckloads of money and fund my own company. But it’s totally unrealistic right; the husband wouldn’t want to do that. So now I'm running my own company and raising my children from home at the same time.

What have you found makes the whole task of balancing work and children easier? What’s the most effective, efficient strategy?

Give stuff up. I have to give a lot of stuff up. I don’t have any friends, we don’t travel and I haven’t see a movie in maybe 15 years and all my finances are ruined because I spend it all on childcare. I’m probably faster at giving stuff up than most people because I’m ok failing. When you have to give up a fantasy, you feel like you failed, the first feeling you have is failure.

You said you feel like you’ve failed but you’re the prime example of someone who has done it very well and on your own terms…

But you’re not seeing the bad stuff, the situations where you’d think ‘oh my god I would never want that.’ I’m not with one of my sons three days a week, a lot of the guys I hung out with in Silicon Valley don’t give a shit about me because I take care of my kids, there’s all kinds of stuff that people would hate, they’d be grossed out by the costs I’ve had to incur in order to create the life and success I have right now.

It also has to be said that these sacrifices have to be made…

For me, that’s what’s really important – asking people what they gave up so you can decide what you’re willing to give. It’s interesting to think about it like that, I want to hear that from everyone, I want Sheryl Sandberg to tell me what she gave up, I want Barack Obama to say ‘here are all the things I gave up to be President’. Everyone should write about that all the time; that is the only honest thing to write about when you write about how to achieve success in any area, that is where all our pain is and also the real reason most people never really manage to do what they set out to do. 

Did you ever get to the point where things ended up being far bigger than you expected?

My brothers were all really impressed with me landing the TechCrunch's list of 30 women revolutionising tech, they all think I’m a nut job because the way I got it was I just went out and asked for it. But also these little moments, like when you say ‘you’re so successful’, it doesn’t feel that way.  I just feel like a normal person who eats dinner with the nanny, trying to deal with things.

You seem like a big proponent of women staying at home, on the other hand, you’re a career coach and you do both – you’ve created this new beast entirely where you’re the breadwinner working from home homeschooling the kids

But when you look at what someone’s life is, you have to look at what they did to get there. Instead, usually you’re only looking at the moment when you’re looking at their life. People should know what it’s like to be an entrepreneur, the struggle it is on an everyday basis. 

Do you feel like you’re on top of things?

I feel like I’m used to not being on top, to not having money. If I’m trying to give all my money to my kids and to keep the company going, there’s never any money for anything, ever. That’s something people don’t realise but it’s all out the door, I’m not sure people see that part. I’m not sure if people could handle their card being rejected all the time. 


Silkarmour Selection: The Best of Penelope Trunk

The Modern Woman’s Life Blueprints

Building a career is sometimes the easy part when planning the infrastructure of what is ‘Your Life’.  Trunk teases out the finer, yet essential details on how being a woman automatically changes how you should shape your career, touching on both the personal and the fundamental aspects, far beyond the  ticking of the biological clock. 

The Three Career-Path Types & Finding Yours

Trunk is no stranger to changing careers and her reflection how personality types cater to different roles might be a godsend in starting over. Although soul-searching may be arduous, it needn’t be excessive with Trunks snappy categories on what exactly to engage with in your career – after all buying the wardrobe to match with Silkarmour’s selection will be the easy part. 

Interviews: How to conquer the three classic questions

We love to talk about ourselves, but as Trunk points out, a job interview shifts the dynamic completely. Telling the story of your professional life and career development gets repetitive but as Trunk suggests, each part is to tease out aspects of your personality, which you can then shape to the necessities of the role.

silkarmour boardroom in conversation with Penelope Trunk



Business & Career Silkarmour Boardroom Series

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