I don’t have to go to work today. In fact, “work” is now whatever I make it. I’ve gotten some great support, comments, and questions on my Leap of Faith post last week so I wanted to say “Thanks!” and answer some of those questions.

So how is the freelance life turning out for you? It’s not 100% clear to me what you are doing right now and I’m curious :-) - Wouter Groeneveld

I was somewhat intentionally vague in my post - partially because I’m still working out the details, but mostly because I wanted to make it less about me and more about the idea of taking a leap of faith. But now it’s time to get down to brass tacks.

What will I be doing with all of this new-found free time?


I’ve invested a lot of time, sweat, and money (thanks NYC gym membership fees) into getting myself into shape over the first half of this year. At my heaviest I was 38lbs heavier than I am today. That’s a lot for my 5’2” frame. I feel about a million times better than I did then - in terms of energy, confidence, and general health. I have a goal in mind and I’m going to putting some of my time toward achieving it. If you’re looking for a morning (read: after 9AM) workout buddy in NYC, drop me a line!


For the last year or so I’ve been pretty focused on freeing my life of clutter. I found this in an old blog entry:

I’m far less focused on "stuff" and more on “experiences."

That still rings true. Being so busy with work, I’ve lost track of that mindset and am going to spend a few weeks getting back to a more minimalist state. I’m not going as far as Andrew Hyde’s 15 things but I do want to eliminate enough “stuff” from my life so that I can be more free to travel, sublet, and not have the overhead/distraction of clutter. Plus, I don’t need a lot of the junk that I’ve accumulated. A lot of it is slowly making its way to Bondsy, if you’re interested.


This one is slightly more complicated as traveling requires money and I’m putting myself on a pretty tight budget. I think with a combination of spending time in places that have a significantly cheaper cost of living than NYC and paying close attention to airfare deals, I can make it work. I’d like to use this time to see as much of the world as I can. I’m open to suggestions / couches to crash on. Whether it’s Missouri or Montenegro, I’m up for anything.

And the one I'm sure you've been waiting for: Work

I have big plans in this department. Here’s a rough sketch:

I want to be able to combine my love of building amazing products with my love of travel. I want to meet startups from around the country and around the world - get to know the teams, get to know the products, and get to know the unique pieces of their culture and the markets they’re building for. I want to learn. I want to share my knowledge and experiences having been a Product Manager at some pretty amazing companies over the last 5+ years. I want to bring all of that together and work with these companies over the course of a few weeks to a month to iterate on their product and make it the best thing ever. I’m kind of calling it a Product World Tour / Global Product Boot Camp in my head…we’ll see if that sticks.

This is going to take a lot of coordinating and getting out of my comfort zone, but I think that’s what I like best about it. I’d get to share my skills with people from all around the world, work on a bunch of great products in rapid succession, and learn a whole ton along the way.

A few key things need to fall into place for this to happen. Most obviously: getting in touch with awesome startups. If you are part of one or know of one that you think could use some TLC on the Product side, I’d love any leads!

In between all of that, and as I get it all orchestrated, I’ll continue to teach classes at GA and I’ll be doing some freelance webdev work. Possibly from a beach in Thailand or while eating some Pho in Vietnam. We shall see.

That’s the plan for now. I’m open to any advice, suggestions, tips, warnings, or opportunities you guys may know of. I know a lot of you have done something similar in the past or are still living the independent life, so leave your best tips below in the comments!