Finding courage to steer your career

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It’s a lot easier to give advice than to implement it. You can imagine how acutely aware of this I must be.

After I’ve given out the same piece of advice twenty times (for example, get a mentor), there comes a point when I can’t face myself if I don’t follow it. Sometimes I try to scare myself. I tell myself that my career will go nowhere and I am wasting my time and I will never get what I want without self-discipline. What I really want from that lecture-to-self, though, is courage to do what is difficult.

Part of having career success is finding the courage to implement what you know you should do. Here are three things I’ve come across recently that inspire courage:

1. Courage to start a new business
I have a friend who is studying artificial intelligence at a big university. He tells me that most of the graduate students are ostensibly working on the PhD’s, but they’re really waiting to find some cool company to go work for. I don’t think this is unique to the artificial intelligence geniuses. I think many, many people are waiting for a good idea.

But you can’t always tell it’s a great idea until you try it. When I asked Guy Kawasaki how you know to move forward with a business, he said, “Launch it.” Then he paused and said, “Don’t worry, be crappy.”

So really, you need to just get out and try the business. That’s hard, though. Instigator Blog inspires courage to start by listing five reasons why you should go ahead and say yes to a new business even if you fear it might fail:

You'll learn something. Even if the idea doesn't fly, you'll learn something valuable.

You'll get a rush of adrenaline when you jump in.

You'll realize the value of an idea.

You'll get a chance to connect with people.

You'll be inspired.

(Thanks, Emily)

2. Courage to make networking strategic and deliberate
Of course, networking is good, and you should do it. But it’s hard. And probably the hardest part is fearing that the person will not be receptive to your networking efforts.

But you still need to be strategic, even in the face of rejection. Ben Casnocha, who surely must be the recipient of hundreds of networking overtures, writes that someone recently tried a nifty networking move on him that he liked: “After we met he studied my blog and reached out to a couple of my friends. After they heard I met with him, they too took a meeting. After they met with the guy they emailed me and we shared our mutual impressions (positive!). Great strategy. The more entry points you have in a relationship with someone the stronger it is.”

This is good advice from Ben, but what really stands out to me is that Ben seems to truly appreciate having the chance to meet this guy. This should give you courage to make overtures of your own.

3. Courage to take control of your own time
All sorts of polls show that time away from the office is a top priority for Generations X and Y. But not everyone does a great job at drawing the boundaries that preserve a home life. In general, it’s hard to draw boundaries because it always seems that what we are involved in is so much more important that violating the boundaries this time is okay.

But Mark Zuckerberg, the CEO of Facebook shows us that courage to protect his personal life knows no limits. The Wall St. Journal reports: “During one series of talks with Microsoft, Facebook executives told their Microsoft peers they couldn’t do an 8 a.m. conference call because the company’s 22-year-old founder and chief executive, Harvard dropout Mark Zuckerberg, wouldn’t be awake, says a person familiar with the talks. Microsoft executives were incredulous.”

9 replies
  1. Emily
    Emily says:

    Great stuff, as always, Penelope. Each of your three points hits home for me right now. I think I’m going to make a point of reading one of your columns first thing every day.

    Hey, there’s an idea for you: the Brazen Careerist 365-day desk calendar!

    I’m glad you liked the Instigator Blog list; thanks for the acknowledgment!

  2. Matt
    Matt says:


    I’ve been a reader for the past couple weeks and I’m a huge fan – speaking of “courage to,” I’m impressed with your own courage to offer candor regardless of topic. Too many believe authority and candor aren’t compatible.

    Anyway, I decided to leave a comment after writing last night that “the virtual mentor cometh” – made me think of your blog and wanted to reach out.

    Appreciate the great advice, and glad to hear of another former NYCer in the Midwest!


  3. Ben Yoskovitz
    Ben Yoskovitz says:

    Penelope — I’m glad you enjoyed my thoughts on “reasons to say yes” … it’s nice to see people linking over, and especially to see my name so close to Guy’s.

    I hope you’ll hop over to Instigator Blog and join the discussion there in the future…

    Best of luck!

  4. Alexandra Levit
    Alexandra Levit says:

    Penelope, I love it. Courage is so critically important, as is work ethic. I’m not sure why people believe it’s easier to work for themselves, when in fact self-employed individuals who steer their own careers are hardest working people out there. It’s easy to show up at an office every day and meet the most basic of expectations. What’s difficult is taking those scary, risk-filled steps to go after what you really want in life. I never stop admiring those who can do it without looking back.

  5. Jason Alba
    Jason Alba says:

    not to be a “me too” but I loved this post… especially Guy’s quote on just launching. I did that in May and have made improvements (some monumental and some gradual) ever since. And I launched my blog shortly thereafter, not know what I was getting into (now I’m addicted – a blog junkie).

    I suggest one more, off of Jim Collins, courage to “face the brutal facts.” I’m all about people understanding that they don’t have job security (I thought I did until January), and am amazed that so many people want to ignore this concept, like the big pink elephant analogy.

    Anyway, face the brutal facts is as applicable to you (the reader) as it is to a company that wants to be “great.”

  6. CrankMama
    CrankMama says:

    Great post! Courage to be “crappy” is an excellent message! SO many of us are afraid to take risks… success can be as much of a trap as failure.


  7. Wendy
    Wendy says:

    I also love the line about the courage to be crappy. Or, in the case of seizing control of your own time, perhaps it’s even about:

    “the courage to underachieve in your career so you can overachieve at life itself.”

    (You might be capable of rising to the top of the corporate ladder; but maybe you’d rather stay a middle manager and enjoy evenings with friends or family, taking great trips, and spending weekends just hanging out with your kids.)

  8. PunditMom
    PunditMom says:

    I have such hard time networking or defending my time, but I continue to try at both. I did find the “courage?” this year to agree to be in a local professional association to meet people I wouldn’t otherwise. It is way out of my comfort zone, but I keep telling myself it will be worth it in all sorts of ways in the long run.

  9. Penelope Trunk
    Penelope Trunk says:


    For what it’s worth, I think you do a good job of networking with me via this blog. Your comments are good and the quality of interchange we have via each others’ blogs is higher than some of the exchanges I’ve had at supposed “industry networking events”.

    I think people underestimate how effective commenting on someone’s blog is as a networking opportunity — especially in cases like yours where the commenter has a blog or two as well.

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