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Recently, I have been given an opportunity to think about how to be successful. Strangely enough, that is not a question I have thought about very often because, over my life, I basically just bumbled from one opportunity to another, without giving it much thought. This probably explains why, after 37 years in the field and counting, I am still a nobody who mostly plays with computers a lot. I haven’t done badly, which is more down to luck than to good planning. But, to quote a friend: “I’d rather be lucky, than good”...
Interestingly enough, another friend, Todd Underwood (not this one, but this one), ex-Google, ex-OpenAI, and ex-Anthropic, wrote about career success in a LinkedIn post recently where he summarized his career and concluded with this wisdom: “When early career folks ask me for advice, I’m genuinely stumped. “Be lucky” is probably top of my list. That’s really not that helpful. I’m sorry.”
I do a lot of career coaching and my first question typically is why people studied computer science in the first place. Over the years I have heard phenomenal as well as heartbreaking answers to this question, like the following ones:
“The first time I saw a computer I had a religious experience…” (this also holds for me).
“I wanted to study medicine, but in my country, people of my race are not allowed to become doctors, so I studied computer science instead.”
“My father gave me three choices: Doctor, lawyer, software engineer, and I cannot stand blood and the law seemed boring”
“I wanted to study something else, but for that I had to leave town and my parents demanded I stay local, and locally there was only a technical university and computer science seemed the least technical subject.”
I ask this question because it goes to motivation. It is hard to be successful if you are not intrinsically motivated to do whatever it is you are doing. I am not saying that there is anything wrong with studying computer science out of something other than a passion for the field, but you might want to take this into account when figuring out where in this beautiful and large field you want to be going.
The next question I ask is if my “client” actually wants a career. The typical answer, after some hesitation, is affirmative, and people often wonder if this is a trick question. It is not, and I usually follow up by asking what a career is and why they would want one. More often than not, people then look at me completely bewildered. Of course they want a career, they always say, everyone does, who doesn’t? But that answer is then relentlessly picked apart by me if it turns out, as it often does, that my client has no idea what a career actually is or has only the vaguest notion.
I am not upset or surprised about this. I certainly never thought about it, and I basically always just took the fun job that was right in front of me, without worrying much about the path of my working life. Like I said, I haven’t done badly at all, but there was a substantial amount of luck involved and as a general rule it is not advisable to rely on luck too much.
Movie tip: Intacto by Spanish writer and director Juan Carlos Fresnadillo. Per Wikipedia: “the film depicts an underground trade in luck, where fortune flows from those who have less to those who have more; the premise purports that luck can be amassed and transferred as any other commodity. The story follows several participants as they engage in literal games of chance, each one more risky than the last, to eliminate the unlucky.”
A career, for the interested, is “the long-term path of your working life, the sequence of roles, skills, accomplishments, and relationships you build over time around a theme” (thank you ChatGPT, for this definition). A career builds towards a goal, and typically you advance to more senior, more advanced, more influential, and better paying jobs. Obviously, that is not going to happen without a plan that helps you plot your moves to bring about that goal. Each move you make needs to be a step on your career ladder and it needs to be the right move, to the right place, at the right time. It also needs to be a move to a position where you think you can be successful, which brings me back to the original point that I wanted to make in this Wednesday Wisdom.
Generally speaking, before attempting any endeavor, it makes sense to figure out if it is something you can be successful at, what success actually looks like, how to recognize if you are being successful, and what to do if you figure out that you are not. You would be a fool if you jumped into something without considering these questions. Using that yardstick, I have mostly been a fool in my life. Fortunately for you, the purpose of my life is to serve as a warning for others 🙂…
A large part of success in the context of employment is meeting the expectations that your employer has for you. Realizing that, it stands to reason that you need to know beforehand what these expectations are, preferably before you sign on to a new job or join another team or project. This is especially important as you get a bit more senior, because senior engineers are often hired to solve some specific problem, such realizing a change in the technical architecture, nursing a suboptimal team back to performance, or rolling out a security program in order to get ready for a certification like FedRamp. To be successful, you need to know what they want you to do and then be laser focused on doing exactly that. If your prospective employer does not have a project that they want you to work on, you should maybe wonder if you are perhaps an ornament rather than an instrument and realize that it is hard to be successful as an ornament, especially if you, like me, are not particularly beautiful.
If your new employer or manager cannot give you a good idea of what the defining goal of your stint should be, this will be the first thing to figure out once you start.
The second thing to wonder about is if the conditions for success are in place. This starts with your own qualifications and you should certainly ask yourself if you have what it takes to achieve the desired outcome. If you don’t, maybe do not sign on, because you will obviously be setting yourself up for failure. On the other hand, do not be too modest, because if you only take on roles that you know you can comfortably achieve, where and when is the growth going to happen? The trick is to find things to do that are challenging and for which you need to stretch yourself, but that are still in reach.
As my dear old mother used to say: False modesty is worse than vanity.
An equally important condition for success is whether all the organizational prerequisites for success are there. In other words: Does the organization really want this? How willing are they to put their money where their mouth is? Will they make sure that all the support you are going to need will be there? No complicated project is a one man show; there are very few projects you can pull off all by yourself. As a general rule, you can only be successful if the people you work with want you to be successful and will give you support in the form of time, help, headcount, budget, advocacy, and office space. Ask yourself this: Is all of that available? Often the only way you will get all the help you need is if you are going to work on a project that is vital for the business in some way. You will typically not be very successful on someone’s vanity project that nobody really cares about
The next thing to do is to make an exit plan. That sounds a bit counterintuitive because why would you think about the exit when you haven’t even started yet, but it is absolutely vital to make an exit plan for everything you are going to endeavor, be it a startup, a project, or a new job.
Or a romantic relationship, for that matter 🙂
The exit plan should contain an observability section that monitors your progress: The milestones you want to reach and the materialization of the support you need. If you are struggling to reach the milestones or if promised support does not appear, you need to stop wasting your time, pull the parachute, and exit the plane.
The exit plan is there to stop you from wasting your time when there is no way you are going to be successful because the conditions for success are just not there (or maybe: Just not there anymore). Maybe you were bamboozled during hiring, maybe company priorities changed, maybe your executive sponsor resigned and moved on. As the Cirrus aircraft marketing slogan goes: Chute happens, and if that is the case, stop wasting your time because if you don’t, nothing good will come out of it. In fact, leaving at the right time might be the only way to turn this dud into something of a personal success.
The reason I am bringing all of this up in terms of your career is that your career is a succession of jobs or projects, each of which is a stepping stone to the next one. Only successful jobs/projects help you move forward, so it is important to make each one of them count and to be as successful at them as possible.
That said, please also realize, there is more to life than being a VP of engineering at age 35, which goes back to my career coaching question: “Do you want a career and why?” I might not amount to much, career wise, but I am having a hell of a good time. You have only one life to live and as far as I am concerned, your only mission should be to live it well, which for you might not mean climbing the corporate ladder or chasing someone else’s definition of success. The real wisdom that I want to impart on you this week, is to be in charge of your own destiny and define success for yourself.
With that in mind: Happy Holidays!
