On career evolution & exploration

Last Friday, I resigned from my job as Design Director at Redstar. While I believe in what Redstar is doing and while I enjoyed the people and the environment very much, it had become very clear to me over the past year that it was not where I belonged, and as a result of that feeling, I was struggling in my work. I mean really struggling.

It’s not easy for me to come in, put in my hours, and collect a paycheck. I care far too much about what I do, and my midwestern worth ethic doesn’t jive with that kind of mindset at all. And let me tell you, when you work in startups, there is nowhere to hide. You can’t feign interest in a company where you’re one of a handful of employees, where everyone else is highly engaged, not to mention busting their ass to make it a success. You simply can’t half-ass it. It is just not possible. And because of my inability to half-ass anything, I have chosen to work in startups for the past 16 years.

But I am tired. Really tired. And it was affecting both my performance and my happiness, and the more unhappy I became, the more my performance suffered. Further, I found myself involved with companies that, while fun and interesting, weren’t in sync anymore with what I was excited about on a personal level. So, with a heavy heart and a clear conscience, I resigned.

The more interesting part of the story, of course, is how I got to this place where I was leaping off a cliff (because that’s what I’m doing — I’m not going to another job), and feeling only a little bit freaked out about it.

It started with RISD. When I began teaching, it was like a whole world opened up for me. I was engaged with my students and my curriculum, finding joy in the most mundane of tasks, and experiencing a resurgence in my own creativity and natural curiosity about the world around me. I was literally seeing things differently. And I was a student myself — a novice, learning to teach. I read books and articles on education. I studied the curriculum of other design programs. I took a teaching workshop. I spoke to other professors and started following some educators I admire on Twitter. I networked. I asked questions. I wrote notes to myself. I asked for feedback. I made mistakes and I learned to correct them. And slowly I became a teacher — and a good one, if the student work and evaluations tell the truth.

I love being a teacher. And I love learning. That was lesson one.

The other tipping point came when Tanja and I started GIVEGIVE. I hadn’t realized that I was capable of half of the things that I do on a day-to-day basis, just trying to get that company off the ground. I don’t have entrepreneurial parents. I don’t have an MBA. I don’t even sew that well (GIVEGIVE is a fair trade fashion brand with a social mission). But I have worked in e-commerce for a long time, worked in startups, and worked in fashion. With Tanja by my side, we decided that we would help each other through the tough spots and ask for outside help when we needed it along the way. And you know what? Our friends and mentors have been more than willing to help us because they support what we’re doing, because they want to see us succeed, and because they love us, or at least they like us enough to spend an hour telling us what we’re doing wrong… and how to fix it, which is terrific.

So, lesson two was that I’m not alone in wanting to create my own company — one with a social mission to create something that elevates women in societies where they are marginalized. Lesson two was about creating something bigger than myself, and that it wasn’t just a desire, but a necessity. Lesson two was about enabling hope to live where it currently has little chance. Lesson two is about giving, not receiving. Lesson two is about taking all of the opportunities I’ve had and applying it to give others a fighting chance.

Note: You can read more about our travels to Nepal and why we’re doing this on our blog, or you can see what we’re up to on Facebook & Twitter

Honestly, I can’t believe how long it took to get to this place where I am ready to let go and take a chance. It is in my nature to dream big for other people, but not for myself. I’m not sure why that is, but it’s something I’m finally allowing myself to do, and it is hard. But being uncomfortable is part of growth, so I’m trying to let go of the lines, drift away from the shore, and see where the winds & the current take me, because it could be someplace wonderful and unexpected.

There’s a quote that I love from Grace Murray Hopper (and if you don’t know who she is, then holy cow, please read up on her. What an inspiring woman.):

A ship in port is safe; but that is not what ships are built for. Sail out to sea and do new things.

I never thought I would be an explorer, but I am learning to be one.


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  1. Stephanie Quilao says:

    Good for you! I did a similar thing when I moved to Phoenix. I basically just showed up with no plan. I just had an internal knowing that something great would happen as long as I stayed open. And it did!

    It takes bravery to leap into the unknown but so worth fighting for your happiness :-)

    • Annalisa says:

      Thank you so much, Stephanie. I keep reminding myself that it’s okay to be scared. And that if you’re not scared, you’re not really evolving. :)

  2. Max Daniels says:

    I am busting with excitement for you! I can’t wait to see what happens next. May it be a atraight-up pageant of wonder.

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