Fifteen is for Freedom

A year before I left Google, I crafted an 18 month plan to set me up for what came next. 12 months into it, I realised I should stop waiting for the rest of my life to start and handed in my notice.

I had many good experiences at Google, even if some… weren’t so good. I learned a lot, even if some of the things I learned were about what not to do. But equally, I spent 3 and a half years working on other people’s ideas, other people’s priorities. Don’t get me wrong – much of that time was on things I believed in and that I’m proud to have contributed to.

When I left, I could see the path that diverged in front of me. The most obvious was another job – there are some great companies out there, doing interesting things. One of the things that made me reticent is that my experience has broadly reflected the data on what women experience in the technology industry, and I was afraid it would be no better elsewhere – but unless I explored, I would never know. The other path was less clear, and included exploring independence, making my own ideas, doing some consulting.

I never really got around to looking for jobs, I was too busy travelling, and speaking, and making. Also, I am terrified of interviewing. But I did follow all the way through with one company. I think this is down to them being incredibly nice, incredibly Canadian, and having an interview process that was just not that terrifying. Each interview I did, I felt like I had learned something, and I just wanted to keep on having those conversations. I made it all the way through to the end, and was shocked to get an offer. Probably because my strategy for dealing with the terror is to focus on the moment, assume it won’t happen, and not get attached to anything.

Like I said, they are really nice, and they let me take some time to think. And so I threw myself into the “what if I am independent” because that was the path less travelled, the one where I had no idea what it looked like. Some days I just freakin’ loved it. Others I felt overwhelmed by the lack of structure. Sometimes I was discouraged. And so I kept thinking, “what if I move to Toronto… I bet that guy is a great manager… wouldn’t it be nice to work on a team again.”

And some days I reminded myself that it took a year for me to leave my last job. Told myself that this time I should interview at more than one place. Didn’t. Fired up XCode and wrote code instead.

I’d always taken for granted that I would not stay in the UK. But some family health problems (everyone is fine now, thankfully) made me wonder if I would be okay to take off to another continent again.

I’ve learned a lot over the last couple of months. But here’s a big one: I don’t think you can be an entrepreneur whilst playing one foot in and one foot out. I think you have to bet on yourself. When you have a good option on the table, it’s easy to take each discouragement as a sign that is the option to take. Maybe it is – but not for that reason.

Decision time came. And I realised that when it came down to it, option 1 was a job that I was afraid to miss out on. Option 2 was the terrifying unknown, the freedom painfully bought that I would regret forever if I did not explore.

I chose freedom. It means I can spend more time this year (all of it, if I want) closer to my family which is important right now. It means I can get some of the ideas that have been bugging me for a long time out of my head and out into the world.

I think the way you set expectations is important. I can think of acceptable reasons to give up this experiment (e.g. it makes me miserable). But I want to set the expectation with myself that 2015 will be spent exploring the road not taken.

Things I want to learn:

• Can I actually run a business? The answer to this is quite possibly no, but I don’t think there is any other way to find out than to try.
• Could I work fully remote? This will shape what kind of jobs I’m open to in 2016.

For 2015 I chose the word “ship”. I laid a lot of groundwork in 2014 for things that will come out in 2015, and this is my reminder and commitment to myself to keep pushing things out there.

This year I’m available for:

• Limited consulting on mobile + mobile technical strategy. I’ve been helping some non-technical founders understand the technical aspects of their business which has been super rewarding.
• Very limited diversity consulting (50% allocated for 2015 already).
• Speaking.

If there is something I can help you with, please get in touch – catehuston AT gmail DOT COM.