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My Career Story gets interesting …

Posted by Amy Wilson on January 24, 2011

Amy Wilson: Risk-taker?

As Jason Seiden suggested long ago, I’m screwing my career path and living my story.

Today I say goodbye to TalentedApps and begin my new online life as Shiny & Useful.  In parallel, I am bidding farewell to Oracle after 13 wonderful, continuously challenging years (6 at Oracle; 7at Peoplesoft) to start my own research and advisory firm Wilson Insight and to join Constellation Research, a highly esteemed group of independent analysts.

In making this decision to take a giant career leap, I asked myself a few questions.  This being TalentedApps (a primary source of career advice for us all, let’s be honest), I thought you might be interested …

Am I risk averse?

The prospect of giving up a steady salary, a well-crafted organizational infrastructure, and the comfort of knowing how to do my job well may be considered “risky.”  I certainly thought so!  And so, my first question to myself was “am I the kind of person who takes risks?”  Chris Melching, of Power Camp fame, asked me this question awhile back.  I hedged, and said something about creating  opportunities for myself that allowed me to choose change.  I had indeed made major shifts in my career, moving product lines (Financials to HR) and moving functions (consulting to development to strategy).  But the thought of striking out as an entrepreneur on my own?  No … safe to say, I fell in the risk-averse category.

Is this risky?

Given my general risk aversion, I needed to determine just how risky this opportunity was.  As I thought about it, I realized just how much support I had – coaches, sponsors, friends, network, family.  In fact, I have huge support in taking a giant gamble – it’s sort of like playing roulette with bumpers.

All in all, not that risky – but I did need to figure out just how I felt about success and failure.

Can I imagine myself in the role?

It’s really important before you take on a new role or responsibility to imagine yourself doing the job – imagine the skills you will need, the kind of work to be done, and, of course, the feeling you’ll get from the work.  There are indeed huge gaps in my vision of what this is going to look like, but generally speaking, I had enough observational and experiential data to realize what my life would look like.  And, it felt good to imagine myself doing it.

Can I envision success?

Doing it is one thing, but being successful at it is another.  What does success look like for me?  Here, I find it important to strike a balance between specific goals and broader aspirations.  It’s almost like a Chinese menu of success possibilities.  I will feel successful if I accomplish a, b, and d or if I accomplish c, d, and e.  The important thing is to realize what a – e are, not necessarily to get my heart set on mastering every one of them.

But as Ken mentioned, success is just one side of the coin.  There is also failure.

Am I OK with failure?

If this just doesn’t work out, am I OK with that?  I realized that I was.  It is an experience from which I will develop, regardless.  I will learn; I will grow.  I will know more about myself and what I’m capable of than I did before.  I will still have opportunities and possibilities.  Ultimately, this answer was the most important.

Here is to failing spectacularly … or not (hopefully).



26 Responses to “My Career Story gets interesting …”

  1. Jason Seiden said

    Amy, you’ll do great, I have no doubt. Here’s to this next, shiny, and useful chapter in your story!

  2. Amy, I agree with Jason. And like Meg, I will sorely miss you and TalentedApps has lost a wonderful contributor. However, just to show there are no hard feelings, we’ve added you to our Blogroll! (over on the right ==>>, I wish there was a way to bold it or something.)

    Here’s to your Hero’s Journey!

  3. Meg Bear said

    Team Amy is looking forward to watching your story unfold.


  4. Debra Garcia said

    Amy, I think that Raggedy Ann doll is more afraid of you than you were of that red haired beast. I think there is a metaphor there. I’m watching you take your radical leap and missing you already. YOU GO GIRL.

  5. Amy,
    This is good news. Congratulations, and welcome to the analyst world. Look forward to catching up.

  6. Amy,
    This is super exciting and smart! Just like you. You have so much experience and talent to draw from, you’ll do great. Congratulations!

    Laurie & John

  7. Vivian Wong said

    Amy -Congratulations!! I am so very excited for you. While we already miss you terribly over here, we KNOW you will do great and look forward to lots of shiny and useful posts from you!


  8. Anne Marvin said

    Wow Amy… this is SO exciting! If anyone can pull it off, it’s you Missy. I’m ready to hear more!!!

  9. Jyoti said


    There are some individuals with charismatic personalities who succeed and excel in anything they do. You are one of them and will do wonders in what you do next.

    Best wishes,


  10. We’re all behind you, girl! And although this is a great, inspiring post I’m sidetracked by what a cute baby were. But I’ve got babies on the brain…

    I love it when people I know do great things. Best, best, best of luck!

  11. James Hua said

    Confucius said success depends upon previous preparation, and without such preparation there is sure to be failure.

    Congratualtions on your new endeavor. You have been well prepared for your new journey.. through your education at Cornell, your work experiences at Peoplesoft and Oracle, and your life expereinces. I can only see success for you in this venture!

  12. Chuck Scheller said

    Great news that you are on your own in the HCM world! I’m certain you are leveraging all your experiences to get a great start and I’m sure our path’s will cross again.

    Best wishes,

  13. Jim Riley said

    Best of luck, Amy! I know you do great out there…we’ll continue to look to you for sound, pragmatic advice (with a touch of your patent pending humor and wisdom thrown in). Enjoy the journey!

    • Amy Wilson said

      Thank you Jim! My real goal is to meet with you again 🙂 Let me know what research I can do to make that happen! You are such a great friend.

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