Today is my last day at IBM.

I joined Netrex in February 1999 as a Unix admin

In late 1999 Internet Security Security Systems bought Netrex, largely for its managed services business.

In October 2006, when I was the director of IT, IBM bought ISS largely for its managed services business.

I was given lots of opportunities at IBM. Twice I found myself in the wrong place at the wrong time and was on a list to be let go, but other parts of IBM decided to pick me up. I once resigned to take a job at Deloitte, and at the time my manager told me that didn’t work for anyone and made it worth my while to stay. For many years, I led an incident response function for the strategic outsourcing business, which was later spun off to be what is now Kyndryl. I learned a LOT. I learned so much, in fact, that I decided to start a podcast in 2012, partly to make myself smarter, and partly in hopes that I could help the industry avoid the mistakes I was seeing our clients make on a near daily basis. I have deep scars from all the big security events of the 2010’s - heartbleed, shellshock, wannacry, notpetya, and many others.

In 2019, I was leading an internal practice around cyber regulations (in addition to the IR role) and ended up helping the cloud business out of a sticky situation. Unbeknownst to me, cloud had been looking to replace their CISO, and in March 2020, they offered me the job. My first big test was leading Cloud through Covid.

I had the extreme privilege to lead a team of 184 remarkably talented professionals. We did some cool things, but I regret the long list of things that didn’t get done.

As well published in the news, IBM took a hard line on return to office, particularly for executives. They gave people like me a choice: relocate to a key site (Atlanta was not one of them) and work from the office 3 days a week (with tight attendance tracking), or be let go. I have been working from home full time since shortly after IBM bought ISS in 2006 - nearly 18 years. I spend about 1/3 of my time at my beach place, which I was not willing to part with. Plus, I fundamentally disagree with the return to office approach and with how people have been treated, so I opted to “let it happen”, and so today is the day IBM terminates me.

I’ve saved up enough money that I can take a break for a while. It’s been 32 years since I’ve had more than a week off work, and at least 20 since I’ve had any sort of vacation that wasn’t disrupted by urgent meetings, crises, and so on. I’m going to spend some time with my family, especially my extremely patient wife, in ways that I haven’t been able to.

I have a very long list of things I’ll be doing during this downtime. I intend to get back into podcasting; I am going to write some including maybe a book; I am going to focus more on the fediverse instances I manage to ensure they are enduring; I am going to way too many baseball games with my wife (she is a mega baseball fan); and I am going to take way too many pictures and hopefully find some creative ways to make money with those pics.

TL;DR: today is the end of a long journey for me, and the start of a new one. And it’s a good day.

@jerry
I would like your advice.
I'm currently working with a big company, and I don't agree with the "investors first" method of leadership. Most of my life have been programing and my degree is on business management, so of course I have my own small "company".
Do you regret working so long for others and don't "do your own thing" for so long?
I'm thinking on leaving and making my dream job, but currently paycheck to paycheck so it's almost impossible.
@jerry
I'm still "young" and I talking with my coworkers most of the time I have the feeling they are in the same position as me, wanting to leave but fearing the consequences.
I don't want to be old and regret at least not trying to do my own stuff, but I lack the sustenance and client base to keep it at float by my own. We have good clients today and they very much like our work.
@Andres @jerry Keep building your client base and revenue to the point where you can forecast a growth plan to obtain funding to add resources to build it out without working for another company. Maybe you already have that growth idea but just need the funding. Document it and take it to potential investors or banks. Being young is the best time to make this move. I’m sure you could always land on your feet again if your business does not pan out.
@wdjorth Thanks for your words.
We are currently a handful of people with no so much skill for selling and that's our weakness.
I could have a lot of funding, but sadly that doesn't ensure clients.
@Andres You can hire sales people, but you really need to know and trust the person, and have strong metrics for success in that role, replacing quickly and early if not making the numbers.
@wdjorth
That's the hard part, I can't find "sales people" and the ones that I find usually disappear before bringing the first client.
@Andres Keep looking. It will all come together at the right time