Looking Back On My Last 20+ Years In Tech

I would be remiss if I did not ultimately reflect back on the nearly 25 year IT career that has brought me to this point in life. I am not really going to thank any one company for “all they have done for me”. The reality is every company I worked for since I started in IT, first and foremost, provided a paycheck. Yes, each step in my career resulted in new opportunities to do public speaking, learn technologies, and become a subject matter expert in one or another for a period of time. I have met some great people along the way and those relationships will remain close, and if you know who you are….you know. I mean fuck me, Jon Hildebrand and I built a datacenter in the back of a fucking truck….in 8 weeks…..practically by ourselves (Michael Jang and Brian Paulson were there too), so I did some cool things with some really cool people over these years and that list goes on and on from my past, but now let’s be honest….

I mean let’s get BRUTALLY honest. Working in technology used to be fun. There was a time when things were great at the start of it all. I was even reminded of this from a message and twitter post just today.

Yes, sorry Elon it will always be twitter to many of us. The running joke for the last few years we trying to capture me at a trade show with a smile. As you can see it used to happen but it was well over a decade ago. Thank you Duncan for that post by the way, but I digress.

Every job I have had throughout my IT and Tech career also took years off my life. Figuratively of course, but at the end of the day I spent just as much time enjoying life as I have been being utterly disgusted at things I’ve seen as well as just outright angry sometimes. I was told a couple years ago by one of my favorite leaders “You don’t suffer fools”, which was accurate. He also told me “You expect more out of people because you always give 110%, and when people don’t step up you get frustrated”. Also a very true statement. At the end of the day, yeah, I have always expected the team around me to put in as much as I did. Hell, I expect that out of my new team working the food truck with me. The same leader said many times, “I am always willing to jump in the foxhole with anyone that needs it”. You are starting to see why I got along with this person so well. If you ever played on a team sport, or truly worked with a team that “rowed in the same direction” you get it. The problem is too many people don’t get it.

While I say often that “I just don’t give a fuck”, the truth is I gave way too many fucks there are to give over the years about too many things that I didn’t need to really give a fuck about. Go listen to The Subtle Art of Not Giving a Fuck, and you will get it. I expected way more from some people, groups and entire organizations than I got, and I learned the hard way that being a tech industry employee wears you down in a way that changes you. I mean not like my friends that are vets that saw active combat changes you, but it is still life changing in my world. For every good week I lived in my roles over the years, there was probably a also bad day to match. Here are a few sad examples I have never been able to forget in my life one for each company I’ve worked for that just added fuel to my fire over time. You can’t make this shit up either…

• Had a manager verbally abuse me in front of the team for being late to see my dying grandfather. He said I inconvenienced him from his daughter’s visit and had to come in to cover for me, even though I called him and we talked the night before.
• Was told I looked unprofessional and customers would not like it when I first shaved my head (and I worked in a call center never saw customers).
• Been worked out of a role as a scapegoat for speaking up about changes many people were not happy about, even got no equity even as a “principal” for the last 2 years in the role, when the rest of the team got some.
• Had a manager tell me I could not change roles because “he would not get a replacement headcount” (Like that was my problem?).
• Nearly got divorced and was bordering alcoholism because I only saw my wife 2 days a week for 18 months straight (same manager as the previous bullet for the record). Only a few people ever even knew about this until now.
• Gotten the “you’ve all been let go” Email on a Monday morning only to get the “oh sorry we actually want you to stay” an hour later. Nothing like an emotional mind fuck on a Monday.
• Investigated for expense report issues because a random person, somewhere, just “suggested it” in a conversation with no basis at all. That person was never held accountable for a baseless acusation either.
• Was suggested by HR to “take more connecting flights so I was not sitting so long on flights” which was killing my back and knees vs allowing me to upgrade to extra legroom seats. I even had medical letters.
• Was told I would never excel in my career for being so outspoken and honest. I think this one played out nicely in the end right? I did pretty well for myself.

There are probably more, but clearly those struck such a chord I can never forget them. What I can say is each time something stressful happened it made me realize it was time to start thinking about how to get out. Let’s face it, when you hit the end of the rope all you can do is….let go and hope the rest of the fall doesn’t kill you.

People in our industry talk about burnout all the time. Hell one of the best VMworld sessions I ever did was about burnout, but this goes beyond that for me. I am just kinda, sorta, done with the bullshit, the lies, the half truths, and promises “things will get better after they first get worse”. I am tired of Minimum Viable Pieces of crap that get way over marketed compared to what they actually do, under meh, “those other things are coming next year”, and then never actually do. I am tired of trying to be one of the only voices of logic, reason, or critical thought process only to be ignored, and ultimately have to say “I hate to say I told you so but….” when the shit hits the fan. I am tired of watching shops think they are running things like an enterprise, but then cut every corner they can to save a buck and wonder why nothing ever gets done. Jon used to call me the Chief Reality Officer and it really should be a role that is as important as HR.

At this point you may be like…”holy shit he’s going scorched earth!”. No, I am not even close in my mind to burning bridges. This industry gave me good income and in turn gave me huge headaches. I’m not naming names, exposing people, or telling you where the bodies are buried, but trust me, over the years I know where a lot of those holes are in the desert. It makes no real point to dig them up, and that is not the point I am trying to make here. The point is it’s been a long career that has hurt me mentally, physically, and emotionally. Someone asked me if I would ever go back , and right now probably not. Now if I lose my house and the food truck fails miserably…we all do what we have to do to survive, but today, at this moment, no.

I will state this again without remorse, the companies and jobs I’ve hate provided a stable paycheck in return for service rendered and benefits which has allowed me to get to this point. For that fact, I am thankful to all those companies that offered me “a job” so I could work, learn, and save some of that money to make this possibly, crazy and utterly stupid move. The difference is I think I will be happy with crazy and stupid, at least for a while. Today I control my life and my destiny, not someone four levels up that doesn’t’ even know my name or what I do. If you are wondering too…I will just tell you I walked away from about a $260k a year salary to basically be poor and run a food truck. When you decide it’s just not about the money anymore….give me a call maybe I can help you figure out your own way to stop being a Maze Runner. I can also tell you I am having fun again using technology to support my new small business. It’s given me a renewed interest in how I can use it to help ME and MY business, which is much more fun again.