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The Difficulty in Career Planning

A while ago, an engineer asked me if I could provide advice and guidance for them in planning their own career. Specifically, they wanted something that could be revisited at a regular cadence—monthly, quarterly, annually—with milestones towards some end-goal for regular calibration. In other words, it’d be a roadmap to a deliberate, determined, and almost systematic climbing of the corporate career ladder.

I didn’t have a good answer.

For one, anything planned out beyond a couple of months is difficult to accurately predict; there’s just too many variables around project and team and status of the business and product itself that create uncertainty. And while a fast-moving startup like Affirm measures drastic change in the currency of months, a bigger company that can draw out years’ worth of stable roadmaps will correspondingly take that much more time to reach those milestones, particularly ones relevant for career progression.

For another, I do not know anybody whose career trajectory consists of perpetually upwards movement. The nature of modern work is that there are tasks that are exactly the right amount of challenging to enable growth, but plenty of other work that’s either too difficult or too simplistic1 to meaningfully contribute to advancement. Career arcs can move up, plateau, or even point down as side-effects of fulfilling business and organizational needs.

On the flip side, the open secret to faster—albeit much more uncertain—career movement is by taking on under-appreciated domains and enabling rapid growth: the proverbial “just get on a rocket ship” strategy by taking a half step back for a giant leap forward. Instinctually however, this chance of leapfrogging rungs on the ladder is rare, and naturally difficult to predict. Most roles don’t end up expanding in scope as quickly or as broadly as you’d want, so a reasonable approach is to like as many swings at-bat as possible, adhering to the adage about making your own luck2.

Reflecting on my own career, for the handful of times it did accelerate, a couple of conditions had to be simultaneously true:

  • Good execution of my current work, establishing good standing and hinted at capacity for more
  • A supportive manager and/or mentor, to be on the lookout for better opportunities
  • A new role, project or challenge, at a scope and scale and complexity that substantially exceeded current responsibilities
  • Plans for handling current work so there’s room to take on something new

The first 3 are pretty obvious, but the 4th condition tends to be under-appreciated. It’s not sufficient to just be excited about jumping onto something bigger; current responsibilities—presuming that they’re still important—need to be chaperoned to some sort of steady state. This can be as simple as putting a system into maintenance mode, or it can be as involved as creating a multi-layered succession plan for your soon-to-be-vacant role. This is how the paradox of working yourself out of a job gets resolved: when something bigger comes along, your best shot at realizing the opportunity requires creating the capacity for focusing on the new challenge.

Also note that of the 4 conditions, only the 3rd one—the timing and nature of new opportunities—is directly out of your control. As above, there is an element of self-created “luck” in improving the chances of growth, in the form of maintaining an environment to seize such opportunities. That said, it is admittedly much easier to attribute success retroactively with the benefit of confirmation bias.

All of that is really to say that fretting about a plan, demarcated by time and how long it takes to get to the next goalpost, is probably not the way to go. Setting up a repeatable environment that enables upward mobility is both more satisfying, and I suspect ends up producing better results in the long run. To use a parallel from the sports world, if you focus on setting up the conditions for winning, The Score Takes Care of Itself.


  1. I.e., you probably did it before, and did a good job last time hence you can be trusted to do it again.

  2. Though via a cursory Google search, there are at least a couple hundred pseudo-famous quotes ascribing luck to hard work.

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