This one has been in the back of mind for a while now, and it’s something that all of us will face at some point in time. How to manage the inevitable point in time when “working” begins to mean something different.

Beyond the very last stop in life, this is perhaps the most signficant moment in the corporate capitalist career timeline. On the assumption that you reach finanical freedom, and for many that is not a foregone conclusion so let’s capture the appropriate acknowledgment, when and how to do this is quite a puzzle to solve. This post explores my approach thus far, learnings along the way, and what might happen next.

Let’s start at the beginning of this journey for me. June 2021. This was the timeframe that I made the decision to finish up a 15 year stint of working in Big Tech. I worked with my LT on succession and transition and exited in September. It is hard to capture just how fulfilling, challenging, mindblowing and humbling it is to work in a position of leadership at companies like Microsoft and Google. The global stage, sheer scale, and a lifetime of learning every day. Sure there were ups and downs, but in the twilight revisionist history view of rose tinted glasses, it sure does leave a case of warm fuzzies and happiness.

But like many things, that ran it’s course, I was tired, no that’s wrong, I was deeply fatigued. And I wanted to do “something more” and leverage all those years of experience, learning and execution to good effect. There’s a sometimes undervalued reality that people who successfully live in those kinds of environments are immersed in decades of business success, iterating and improving, measuring and winning. Taking all of that and implementing the best bits in smaller, growing or just different companies is wildy fun. Think about it … all the knowledge on what to do and how to do it, none of the org chart bullshit and politics, and a group of people thirsty to leverage and adopt. In the correct places, that is something that brings joy to me.

And so since then I’ve lived some lives. Got some right, got some very wrong, but always at least in my head, I do this because I want to, I enjoy the feeling of not needing or desiring “career growth” and that brings an incredible aura of positive ambivalence. It really doesn’t worry me if scope changes, roll with it and do what’s needed. I bask in the glow of seeing others succeed and be promoted, I had my time, I fought those battles, and I peaked, and I am so very comfortable with that. As it always should have been, but it never feels that way at the time, other people’s success is not a weight on my own. And oh boy is it fulfilling to help others, offer guidance and coaching, not because I need them to do that, but because it will help them … there’s something different in tone maybe, or because there’s no hidden intent or agenda because of the freedom of just wanting to work on fun stuff and solve hard problems, but the engagement of helping others is far better now than it’s ever been, and gets better every day.

An important sidebar here, none of this is to say I’m not driven or lack desire to succeed. I am 100% here to win, make no mistake. But the role I play, the value I offer, is that I will bring every ounce of experience and knowledge I have to bear on every problem and do whatever is needed as one cog in the machine.

Which leads us to today, and eventually tomorrow.

After a couple of years out wandering in the wilderness, it has indeed been very good to be back in the local rodeo of security for coming on a year now. There’s just something about the insanity and rough n tumble of this world that works for me. Geeky topic, hard problems, complexity, competitive, adversarial in nature. And as a geek who likes telling stories, there’s a lot of geek and a lot of stories to tell!

But at some point this will come to an end. It won’t be today, it won’t be tomorrow, hell it’s quite probably 5 years away. Unless shit goes sideways and the balance of fun to bullshit tilts too far the wrong way, at that point, I have a side gig ticking away here, and another revenue generating one in the waiting, so the vNext roadmap is laid out as a gravel trail over which I will roll. Or someone will say “hey, you have something we could use some help with, wanna come play in this pool for a bit” … then who knows. Life’s box of chocolates is nothing if not varied, and as someone who has had what the cool kids are now calling a “Portfolio Career”, my 30 years and incredibly varied career allows me the luxury of choice.

But let’s look into the crystal ball … what happens in x years time. It definitely will not be a hard stop. A good friend gave me the coaching that that was a very hard road, shifting from a busy schedule driven lifestyle to … nothing … sounds amazing, but in reality quickly leads to boredom and annoyance. Rather he coached, first slow down, then change pace, and then taper off.

I’m in the pre-slow-down phase. I’m not slowing down, but I sure as hell am not accelerating. The slow down begins with vNext, and then tapering off will look like side gigs, part-time (I can’t bring myself to say Fractional without cringe just yet) and then … real retirement.

It’s both a sobering and also exciting time of life to be thinking this way.

Be awesome. And nice.