On Future Goals

You could spend your entire life justifying the logic behind your 9-5 responsibilities. Recruiters are ready to make short work of your wondering. 401ks and mortgages and health benefits are all real concerns and I don’t mention them lightly… but what the hell are you doing in this life if you are ignoring your own answers?

2020 Career Planning Guide

I write this guide every year to wake you up (or blow wind at you, if you are already awake). If you reached for this Career Planning guide, odds are good that you are looking for some movement. And looking for wind is the first step in getting your boat moving…

Career Planning Guide for 2018

Download it, print it, go find a mug of something warm and spend some time figuring out where you’re going. A year is going to pass either way; far better that you have your hands on the wheel!

Beyoncé vs. Ballads (Know Yourself)

  “So what’s #PluckyWomen?” I was standing at the bar, ready to order. I looked up from the drink menu at the dude next to me and in that second a song started playing over the speakers — the song I listen to when I’m writing big SOWs or prepping ambitious new pitches. Maybe it

How to Quit a Job

My son’s beloved preschool teacher unexpectedly quit before Christmas. We live in an expensive area of the country and, understandably, it turns certain industries into revolving doors of employment. Who can live in the Bay Area on small salaries? Not many. Though this is a really logical problem, her departure was a total shock to

Dear Plucky #4: When to Quit

I am starting to seriously doubt my future with the company I currently work for. How do you know it’s time to leave? If it’s not time to leave, how do you make staying seem like a better option? Boy, this is a popular question. I want to start by saying that work and life

Dear Plucky #3: Stuck, but Ambitious

Dear Plucky, I’ve been waiting for a promotion for a long time and keep getting passed up, but my manager says I’m doing great. Should I just ask directly for the promotion? Is this seen as too self-centered? Thank you, Stuck but Ambitious ———– Heya Stuck, I’m picturing you in a holding pattern, like planes

On career path: twists, turns and blind spots

I start every Monday morning at a cafe in Chelsea, where I have breakfast with a few other solo entrepreneurs. We update each other about our weeks, what our focus will be, where our travels are taking us. We teach each other how to use IFTTT; we recommend accounting software; we high-five about clients won