This week I returned to the world of Security after a 2.5 year exploration of very different experiences. I had no idea when I set out on this journey how it would go, how long it would last and what I would learn. Maybe I find something that is what I want to do for the rest of my working life. Maybe I enjoy slowing down. Maybe I don’t.

What did I learn?

I was expecting more insanity, more carnage, a more urgent pace in the startup world. I’d heard a lot about this, about the adjustment I would face leaving Microsoft and heading into this world. There was indeed a change of pace, just not in the direction I expected.

It was slower.

Maybe people don’t realise how crazy paced Microsoft is, maybe Security as a business is different. But we were constantly sprinting and constantly balacing priorities. We grew fast and furious, and so I was attuned to that model. The last couple of years have felt much slower at less capacity. I was often left hunting for that volume, which I suspect was a significant contributor to a couple of missteps.

There was a learning of just how much supporting machinery there is in larger more established environments. Processes, functions, people. In the more nascent environments you’re creating those, and I enjoyed that. Zero to Something is my jam.

I found more people in roles that didn’t have the level of experience I was used to. People in very senior roles who had less experience than even me, and most of them did not have the wherewithall required to know to tap into other people who did have the experiences they were missing.

I misfired on some approaches. I rushed at a few things I should have gone slower, and was slow on a few things that I should have just dug in and got shit done. I own those mistakes.

And I learned that at least at the companies I spent time in, the understanding of what product marketing can be and the value it can offer is sadly missing. One of the primary reasons for returning to the land of security is that I found myself really missing the product strategy and influence aspects and the scale audience engagement, leaving “only” content creation.

Could I have adjusted and been successful. Probably. But I desired more to be happy, and so here we are.

Arriving at a decision

I hadn’t anticipated this change. It began, probably unsurprisingly, with some politics and bullshit. That series of events sent a warning in my brain, and I watched closely. As it became clear how things were playing out, I wiggled a little to see what the reaction would be. It was sadly not what I hoped, and so the message was clear.

I’m not one to hang around and fight a rising tide. I did all I could to ensure things were as good as I could get them, and tried to bow out with as much grace as I could.

I look back on my experiences positively. Things did not always go well, but that’s growth. I messed up a few things and learned some lessons. I achieved some new things and take these with me back into the future.

As that (in)famous saying goes, you win or you learn, never lose.

What to do, what … To … DO …

Figuring out to do was a journey in discovery. I spoke to a lot of people, including recently retired or semi retired people. I did have the option to really slow down and move to fractional roles, maybe some consulting or other self-employed scenarios. I decided that I wasn’t ready for that, I have maybe 5 years left in me of really wanting to be part of something bigger. Who knows maybe there’s more, but that feels like an appropriate milestone for now.

I thought back to the reasons why I left security in the first place, and decided that I had scratched the itches into submission. And so with that decision, it really came down to “where” and “what”. Clearly there has to be a need, and in this world we operate in, there is plenty of that, and once I popped my head up I was fortunate to have a few options to explore. There was a clear winner from my perspective. A company that had that perfect mix of leadership, drive, product, need, opportunity and current state.

I’ve been onboard a week. I can already see my decision is a good one. Time will judge this statement, perhaps we can revisit it in the future, for now, for the first time in 2.5 years, I have a multi-year perspective and plans to enact.

LFG.