TL;DR: Stick exclusively with people who can be trusted with your professional well-being.

A strategy that focuses on personal growth

Murphy’s Law is an adage stating that “if anything can go wrong, it will”. The uninitiated tend to read that as a drier variant of “life sucks”. But for us engineers, the phrase means something quite different: “for an outcome to occur reliably, it has to be driven directly, rather than as a side effect”.

My livelihood is building organizations out of people, technologies and culture. Like a lot of people out there, I tend to measure my career growth via the efficacy of my practice of my art day-to-day and the improvement of my skills over the years. Here, I’d like to present my thoughts on how to drive personal growth in a principled manner.

My core strategy is simple: I try never to “work for an organization”, but rather “partner with specific stakeholders”. I give my partners everything I’ve got and more; I expect in return that they have a positive impact on my professional well-being. If such an impact does not happen, whether through lack of ability, lack of opportunities, neglect or one side outgrowing the other, I move on. The End.

Some examples on what it means to partner with me

To avoid just dabbling in theory, I wanted to provide a specific example of what I expect from my partners in crime:

  1. Communicating, committing and adhering to a joint vision. Positive example: figuring out what new tech needs to be addressed over the next 9 months and splitting up the subtasks needed to making the high-value outcomes happen. Negative example: having a discussion with some bottom line, and then getting a surprised pikachu when I present the conclusions to a wider team.

  2. Trying to figure out how to fix longer-term operational/workflow issues when I’m down in the weeds (which I’m prone to), so that I won’t have to spend the bulk of my time fighting bushfires.

  3. Being attentive to my inputs and investing emotional labor into remediating matters that are not working well; “us” should be important.

  4. Giving me specific and timely feedback, whether it is on shared interractions or my execution style.

The big question: when’s the right time to move on?

While I am a big proponent of being decisive when moving, by no means do I mean that jumping ship should be taken lightly. In fact I strongly believe in trying to persevere for a while before giving up. How long of a bad spell is “enough” to decide that I’m no longer in the right company? My rule of thumb is a year.

Professional growth is akin to developing a strategic investment portfolio: any single choice involves a high risk of failure to grow; the investor needs to diversify and accommodate for multiple failures over the course of a career. Considering the fact that a “good run” is about 2 years and ends up with a bad run, giving 1 year for bad runs is about as much as possible without letting the downside dominate one’s career.

Lack of individual well-being is a reliable indicator of an organizational failure

Let’s consider a different take on the matter: what’s the right thing for the organization, as opposed to just me? Under benign circumstances, my desire to grow aligns with the good of the organization; for example, each of the four examples I gave above translates into the organization getting much more without a lot of downside. This leads me to a key observation: if nobody is accountable for me, as a high-ability hands-on executor – then it is likely that good execution is no longer a priority of the organization at all.

This observation actually applies to much more than the high performers. Teams that further an important area of business tend to develop a style of leadership that tries to improve work efficiency, and in particular develops expertise in carving out complex tasks into bits that are appropriate for all kinds of contributors. The major mode of attrition for a well-run team would be burnout or exhaustion; if the team is managed well, it can be a nurturing professional home for most team members for many years. A team in which people are unwell due to being misapplied is counterfactual to the above – which means it contradicts the assumption that execution is important to the organization.

A well known property of capable employees is that they recognize not being considered important, and respond by plotting their ways out at their own chosen speeds. At some point it becomes common knowledge that there’s nobody relevant anymore at the helm. By then, only a very competent and determined salvage effort can save whoever’s left from whithering away while causing cascading damage elsewhere in the organization.

Assuming that management is rational, the neglect of a certain domain represent a lack of belief that execution in that domain is important to outcomes at their level, when compared to the other things going on at the moment. This kind of a disregard arises from ongoing shifts in values, and is almost never a deliverate choice. The following situations are fairly typical, in my experience.

  • The leadership may just have had its attention temporarily diverted by crises elsewhere.
  • The execution might have been good enough for everybody to assume that it just works - until that stops to be the case.
  • There might still be major value in other adjacent lines of work for an evolved team, for example doing maintenance or operations.

While understandable and fairly common, all of these are noticeable organizational challenges that will become major risks if unaddressed.

The things I lose by putting bounds on perseverance

Most organizations are dysfunctional in some way or other, and a lot of them come up with the strategy of awarding perks to employees in exchange to putting up with dysfunction. My focus on growth means losing such perks. Here are some examples:

  • I cannot commit to a mission, however appealing it may be to others, if there’s no one watching out for me in it. This alone hinders a considerable majority of opportunities I have access to.
  • Since different organizations deal with different tech stacks, I do not specialize in a specific set of technologies. I won’t be “the algorithmic maven” or “the data guy” or “the security guru”, although I can be and am highly proficient in all of these areas. This means also giving up on the career path of a super-expert, which is a great strategy practiced by a lot of people out there.
  • I cannot stick with the majority of outstanding peers I meet along the road - even if they focus on growth in the same sense that I do, it is too likely that their growth goals would be different from mine.
  • I’m giving up up-front on long-term benefits, like the “recharge month” they give out at Facebook/Meta after 5 years of employment or the extremely generous government retirement plan that’s only available after 25 years of service.
  • I haven’t developed skills for office politics or desirable optics, which is a huge impediment if I should ever have to stay in quite a lot of organizations out there.

Wrap-up: no man is an island

There’s an untrivial assumption in the strategy proposed above: that there’s at least somebody decent willing to invest into your professional well-being. A lot of people can’t come up with even one such person!

However, one thing I did notice during my own personal journey is that there are far more people whom I could team up with than the obvious choices; it’s just that I tended to become aware of them too late.

What I realized, along the lines of the Murphy philosophy, is that the search for the right people to team up with should be seen as a stream running continuously through one’s life; thus it is only through continuously connecting to others one can find their place as a part of the whole. Whether for this reason or any other, I wanted to conclude this post by wishing that you’d find the people necessary for your growth, and sooner rather than later!