Beware the professional path. There be dragons here

So, there I was talking to some people and I talked about focus of my career not being the same as longevity in my job. You see, long before the gig economy I started moving between jobs and looking for challenges to fix things. I wasn’t just interested in time clock check ins and moving through the day. There are some early formative moments in my life that created my career track. I get pretty consistent requests to mentor people. I have had more than a few people ask how they could have a career like mine, mistaking result for path, and I wonder if it is my job in life to be a warning to others.

I’m not a Zuckerberg or some other scion of the pantheon of silicon billionaires. I graduate from High School lucky they let me with a solid 1.7 or so GPA. I was a distinct product of a principle called tracking in public education that said I’d never go to college. I did not learn to write or do math in high school. I learned to weld, do engine mechanics, electronic and television repair, and how to mix a great margarita. I’ve ended up a pudgy, graying, middle manager at a moderate sized company with a great culture. When I was a young man, a junior in high school, a guy named Tom talked me into joining the Washington State Army National Guard. Off I went to basic training and to learn to drive tanks. When I got home from basic training to finish my senior year in High School I sat down with my fervent vodka swilling father one night. He said, “You are off to a good start to be just like me.” The next day I went down and inter-service transferred to the United States Marine Corps. You will not find a lot of people who went Army to Marines. Adaptability means sometimes taking the road others fear to tread.

I admit it up front and in front of all as my witness. I was not a good Marine. I didn’t shine in dress blue uniform, never owned the uniform, but I enjoyed my time in the Marines. I trained hard but was fat and slow. I shot like a demon on the range but never deployed to a combat zone. A short stint in the Marines, a pretty significant injury off the base, and on the street again. You have to have a plan when you didn’t have a plan.

Short stints at places that need help are personally rewarding even if they are not normal career paths. A stint as a reserve police officer for a tribe, a stint as a corrections officer at two different sheriff’s departments, and a lot of learning. Learning about people, stress, and a calibration of risk. The tribe needed good people in a bad way but had no money, the first sheriff’s department had just finished a jail, the second sheriff’s department had just gone through a huge investigation of corruption. These are the jobs that others pass on and give great experience. Flexibility is enhanced when you actually need it.

In 1993 I started a half decade of pain. I would do just about anything that was mostly legal to make money. I sold photographs, wrote in the pay on publication market, worked in the yachting industry installing electronics, crewed on race boats, delivered information security solutions, worked in a family business, and I even worked with different government agencies as a contractor. I did a lot of security work because I knew it, but not because it paid well. Meanwhile I was also a full-time student. I worked 80 hours or more a week on multiple jobs across wildly different industries. You can’t have adventure without adversity.

A career is not so much a path as it is a lengthy period of discovery resulting in a snail trail of results. I am warning the young professional about the lack of focus and the adversity of a career like mine. Don’t be like me with the pain and misery of broken marriages, always moving, having plans with a dozen forks and options. Constantly strategizing and never having a firm base to work from. Divorces are painful, they bring on many changes, but when they are done they are done.

In 1999 based on my experience in the military, my experience in information technology integration across numerous customers, and a newly minted masters degree in computer science. I was offered a senior position at a telecom running their Y2K project. Nobody else wanted the job. You know that highly critical failure prone and massive problem other people had been working on for almost a decade? I could point out the Y2K failures the insta-pundits never understood to show how critical the problem. How did I get the job? It wasn’t my stunning personality, or my good looks that got me the job. My lacking personality and infamous hound dog on Quaalude’s looks have limited my career far more than I care to admit. When it came to companies in distress, I wasn’t the first person they called, but I was the last person they called. Sometimes challenge and opportunity are based on the rest of the world not being willing to put up with the misery of long days and high stress.

I worked for another company as an integrator with some of the biggest companies in information technology. I showed up for work, I worked hard, took the phone calls at 2AM, and slept in my car when I was too tired to drive home. Adversity, abnormal discipline, and a penchant for self-loathing go a long way towards keeping a job and moving forward. Always have a plan with a lot of options and an optimized path toward a goal. Which means you have to have some desired end state, some goal, and be willing to deal with unhappy or less than the desired end state. I see in the pop-happiness life coach sphere of influence lots of people talking about not having goals, and very much a buddha approach to being in the moment. I looked into the bleary eyes of my vodka fueled father and saw the epitome of that just be happy approach to life. There is nothing wrong with being a ditch digger unless you’re a ditch digger.

Sitting in a diner in Albuquerque New Mexico a friend leaned across the table and looked me in the eyes. I had been riding my motorcycle and not got to where I really wanted to be that day. He noted the exhausted and hang dog look that was pretty much my normal look. This friend blithely said go get into academia. My in-laws were both academics. I had known many academics. I would find out that I am the antithesis of an academic. A rage aimed, caffeine fueled, damn the torpedoes, ugly, fat, freak who can’t write is not a good candidate for a tenure position. I put out four CV’s (starting with what the hell is a CV?) and got four interviews and three job offers. Only one was as faculty and near a body of water. How did I do in academia? Early tenure, elected to the faculty senate, and then elected to be the chair of the faculty senate, and all in the midst of a recession and some of the worst problems to beset academia in history.  An organization in distress will welcome any beacon of hope for direction. Being where the pain point is will drive opportunity if you can handle the stress, and chance of disaster.

So, I gave up tenure. After staying at a job longer than I had ever intended or ever expected I gave up the golden ticket. I thought I’d stay, maybe camp out, but off to another institution for a variety of reasons I went. Like I owed the government a year of service. My academic institution owed me a sabbatical. I should have been able to go do my service, then return, but that was not to be. So, I quit. I was still in my doctoral classes and would soon graduate with a doctoral degree in technology which most people are clueless what that means. Still off to another institution which also was being stressed. The same recession driving a stake into land grant universities was being reflected as sequestration and massive lay-offs in the military university system.

I was told unequivocally I could stay when the military university was under stress but only if I told them who would need to go. I flip-flopped back to my previous public university system at a different campus. A few years there and the “we don’t like you” petty faculty wars had me flop back into government as an agencies CISO.

Yes, I gave up tenure a second time. Those who know anything about tenure likely figure rightly I am nuts. There is a time when you look at the people around you, and you know that it is time to move on. Either the mission, the values, or perhaps the day to day churn just don’t reflect your core beliefs. It takes a special person to work for substandard pay, with the long hours, and super human intellectual requirements to stay in academia. This drives a culture of knife fights over nothing. The table stakes are meaningless. The petty objectives of many academics are hollow. True intelligence requires introspection into your own biases. If you are in a bitter feud and fighting for something it should mean more than nothing.

As a CISO I was unremarkable. That is the fate of every first CISO at an organization that has never had one. Every requirement is new, every suggestion met with skepticism, and every result near arcane black magic. The CIO was a great guy but destined to leave. The organization had really cool technology. The responsibility was immense. Once again moving an organization off the dime of paperwork whipped security to real security burned good grace and likely credibility to the ground. Every event pointed out the errors and omissions in a system wrapped in the papyrus structures of risk. I exited the organization after less than a year. This is not abnormal for a CISO, and the fact that I was not replaced by the new CIO is a warning for the organization he just joined to lead. I exited with my reputation intact, and a few good friends.

After hours and hours, and late and very late nights, and damning problems with no good solution. In the haze of pain, and in the mind-numbing choice between bad and worse situations. It is quite obvious I had dropped back into the fire filled river of chaos. My oars aflame I tried to bring the best results possible from good idea fairy whacking to realized results, all while rowing like a mad man. I ended up working for the DHS.

The 2014 Federal Employee View Point Survey rated the DHS, Headquarters unit Intelligence & Analysis, Intelligence Operations, and Cyber Division as among the worst, of the worst, of the worst, of the worst places to work in the federal government to work. Employee turnover, morale, and productivity all were in the dumpster fire of careers. This sounds like a great opportunity for me to go make a difference said nobody ever. So, I joined the intelligence community, worked as a subject matter expert, and ended up running that dispossessed little fulcrum of pain known as cyber division. Where we turned around the productivity and morale issues, ended the high rate of turn over, and did so much more. I sacrificed my career in front of CNN, pissed off a sitting president, and ultimately, they took the division I turned around away from me.

I got promoted to the deputy undersecretaries staff. In some ways I would point the incongruity of the results to put it into perspective. My evaluations were stellar, my results off the charts successful, the capabilities and strategies worked out of the box. I was given a huge pay increase, and I was given a massive bonus. Yet, I was moved out of cyber to work critical infrastructure. This likely had nothing to do with me saying the Russian were hacking the 2016 election.

Sometimes the tea leaves are about as hard to read as the results of the FEVS when you want to know why people hate their job. On the surface the ocean may be calm, but the currents are swift, and the water filled with things that will eat you. Fish or cut bait?

The intelligence community takes care of its own, but I looked up from the disaster of being right in front of the cameras and looked for a new horizon. I was a tourist in the intelligence community and burden if I remained. The president said nobody good worked in government, so I got out. I ended up in my current job. Working for a great company, having a great time, and looking back trying to figure out what happened. Sometimes it is your lot in life to represent what is only possible for a passing idiot to do and maybe be the Peter principle in action. Nobody ever thinks that of themselves, but those who can imagine it and fight against the result move further than those who never reflect. Each job, whether more or less responsibility, is a test and challenge of your capability. When you succeed you may be seen as a failure. When you do the right thing you may be called wrong. When you act with honor you may be called evil. When you charge into the chaos and unknown you have to have the will and vigor to pull yourself out of that pain. History is a poor template for success but a great pattern for failure.

Every job, career change, challenge, and goal I have experienced was a path shared by friends and foes alike. I have broken bread with senior leaders who will never remember me, and people just joining the work force I will never remember. Admitting to not remembering everybody you ever meet may seem harsh, but I admit that I can’t even call my dog by the right name regularly. Having met, ate dinner with, shared stages with, and socialized with a lot of senior leaders over the years I think I can safely say they are people too. I have also thanks to other jobs played chess with murderers and rapists. These are people too with a unique bend to what it means to be civilized. All of that experience can be an indicator of why I am less than impressed with the self-importance of others, but I realize that most people who don’t recognize seniority haven’t attained it. There is a certain hubris in being well reasoned on results of your efforts.

I can’t imagine why anybody would want to have a career like mine. Why anybody would seek me out for mentorship. One back breaking, mind bending, torturous task after another, and a life filled with the desperation of fleeting success. These are not the paths to a career, but they may result in good stories. In the fiction of my own mind I am the antagonist challenging my success. I’m not sure I’d change what I’ve done, but I’m pretty sure there were lots of places where the right decision might have been other than the direction I chose. The path from where you are, to where you want to go, and the stepping stones of that path. It is not short, easy, or safe. It is filled with the hobbling shards of life and pain surrounded by hard work and effort. Short cuts are for the movies.