Anything but standard advice is what Penelope Trunk has to offer. Author of the book Brazen Careerist: The New Rules for Success. Founder of a startup of the same name, Brazen Careerist, a web service to help companies find candidates. Find out why you shouldn’t think of creating a startup if you want to stay happily married, and why entrepreneurship, like writing, should be something you start out of necessity rather than money. Read on!


Allentrepreneur: Hi Penelope! Very nice of you to drop by Allentrepreneur for a chat. If I’m not mistaken, a brazen careerist should be one who feels no dissociation between his work and life persona. Indeed, work is an immutable part of life. So why is it so many are keen to keep these two apart?


Penelope: I think you can do whatever works for you in terms of mixing personal and work life. I think it probably works different ways for people at different times in their lives. There’s no right answer. A brazen careerist is someone who is dedicated to creating a good life for themselves by consciously examining the choices they make and knowing that most choices impact both work and life. It takes a lot of self-knowledge and risk-taking to create a life you really like.


Allentrepreneur: Are entrepreneurs much more likely to understand this reality, since their work usually tends to blend in more thoroughly with their lives?


Penelope: As a group, entrepreneurs have an extraordinarily high divorce rate. So they are probably doing something wrong in the work/life category.


Allentrepreneur: I’ve asked this in a prior interview and I think it’s worth asking again: follow your passion vs. follow your opportunities. Which is more important and why?


Penelope: We all have tons of passions and tons of opportunities. The trick is to know which of those to follow when. There is no right answer. Bouncing back from bad decisions means more than making good ones.


Allentrepreneur: Your third start-up, Brazen Careerist, is a unique platform that enables a corporation to find the talent it needs amongst the mass. However, success largely depends on your contributors’ willingness to go beyond the resume and make an effort to understand where its content comes from. Why aren’t more companies actively exploring this innovative kind of recruiting?


Penelope: Almost all of the Fortune 500 is using social media in some way for recruiting through employer branding. The Fortune 500 understands that they must join the conversation. They are just unsure of the best ways to do that.


Allentrepreneur: “My career never had a straight path, […] and that’s what makes my career fun. And sometimes scary”. What motivated you to make the transition from the corporate world to entrepreneurship and what are the best lessons you’ve learned from it?


Penelope: When I was getting my graduate degree in creative writing, my teacher said to us, “If you can think of anything else to do for a career, you should do that. Writing is difficult, and destabilizing, and pays terribly for most people.” I think the same can be said for entrepreneurship. It’s very unstable work, the hours are insane, and for most people, they will make more money at a corporate job. So you should only start your own company if you have to. It’s like being a writer. If you must, then do it. Otherwise, choose something safer.


Allentrepreneur: If we could materialize failure in the form of a piñata and take a swing (or 30) at it with a stick, most of us would jump the gap towards entrepreneurship more readily. But no such luck. How did you deal with what I call start-up fright?


Penelope: I wanted to have a fun job, with a lot of people around me, and if I went to corporate life, I couldn’t leave to pick my kids up at 2:30. So I didn’t have a choice. I did a startup so I could have a cool job and still pick up my kids.


Allentrepreneur: Generation Yers like myself are a whole new ball game. Connected, educated, hungry for change, and above all in search of fulfillment. It’s no surprise then, that many of us are saddling up and taking the start-up route. Tell us why trying to create and deliver value on our own terms could a meaningful thing to do.


Penelope: I don’t think you need to have a startup to give meaning to your life. Meaning in your life comes from the relationships you have. Startups are just a way to have interesting work. Your work doesn’t give your life meaning.