WTF am I doing? #1

I'm a 41-year-old father of two very young kids, who has left NYC, moved across the world to follow a dream of a better life for my family and to build my own company. Each one of those things; middle age, parenthood, entrepreneurship, relocation - is in itself potentially overwhelming. Combined they leave me asking myself WTF am I doing? So I thought why not document it and maybe I'll find some answers, talking things through always makes things easier - so this weekly personal note was born.

There are realities to the situation I find myself in that are often not really explored. Most of the conversation around entrepreneurship is built around success and failure, lessons you can take away - but the majority focusses on the business or management aspect. This is not about that. This note is a much more personal take on the impact of entrepreneurship, global living and parenting.

I can guarantee there will also be talk of surfing, sorry not sorry.

I'm writing this from our new home in Portugal, the wind is currently wild, howling onshore and the waves out front are 20-25ft - it's absolutely unmanageable at any of the spots here. My boards have been stuck in the rack for days while we wait for this to end. As I look at the ocean out of the window, it makes me realize that being out in those waves right now would probably feel pretty similar to building an early stage company. You're going to take a pounding, you're not really ever going to get a wave and it's highly likely you'll be dumped back on the beach feeling like you're about to puke.

The thing is, in surfing you can wait for the good conditions, I don't go out unless I know it'll be decent. I check all the spots, see what's working best, select the right board for the conditions, then the right fins. But in entrepreneurship you don't really have that luxury, you have to get in there and try anyway when the conditions are inhospitable, knowing that the odds are against you and you're about to take a flogging.

And it turns out there will be moments when you definitely will feel physically sick, actually quite a few.

So this note will be a journey of the highs and lows of that experience, how it impacts you personally and more than likely the odd introspective exploration of what led me here. I can't promise many lessons, but at least you'll know what I am doing - even if I never quite work it out.