For every skill, there is a somewhat generalizable progression of measured ability. There is the first time you do something, when you start to do it more and more and learn to recognize patterns/isolate sub-skills to improve, and when you eventually master it. This includes the ability to learn a new skill itself, to recognize skill gaps (see Debugging soft skill gaps), and to develop a more expansive growth mindset (e.g. learning how to spot skills at something like politics or likability).
‘An amateur practices until they get it right; a professional practices until they can’t get it wrong’
One of my favorite concepts in gaming is that of a skill floor and skill ceiling. For example, in some games/skills there is a high skill floor (difficult to learn), but low skill ceiling (easy to master) – like a Rubik’s Cube. In others there is a low skill floor, but a high skill ceiling – like chess. With a Rubik’s Cube, you are competing against yourself, maybe for time or certain conditions, but with chess you are competing against an opponent. I really enjoyed swimming competitively in school because it involved both competing against yourself (the clock) and an opponent (those in the race) – of which you might lose one but win in the other or vice versa. All of these require an environment of challenge to grow and repetition/practice to expand your capabilities measurably.
How you expect to run with the wolves come night when you spend all day sparring with the puppies? – Omar Little (The Wire)
Another tricky element is that with skills there is theory, practice, and perception. For example, someone might be strong at pattern recognition or logic (ability), but might struggle with test or interview anxiety and therefore be underutilized in their careers. Sometimes too, I see people who are very strong at interviewing, but struggle in roles that require more influence and relationship or reputation building (a skill not always evaluated well in on site interviews or a resume). Or maybe someone is skilled and can have an impact, but struggles getting a sponsor for a project and they need to work on building their reputation (perception). In all cases, there are skills to work on to be able to take advantage of other skills and open up opportunities (e.g. principled risk taking).
But, ironically, focusing on the impending test itself is not the best way to improve your performance on it. Suppose in a few months you were going to be asked to do thirty push-ups. You could concentrate on what to eat the day before the push-up competition, and what shirt to wear that’s not too tight or too loose, and how to give 110% at the time of the challenge. Or you could slowly, over time, increase the number of push-ups you can do each day between now and then so that it would be no effort to pump out thirty push-ups at test time. – The 5 Elements of Effective Thinking
In work, theory/practice/perception all get muddled because past a certain level of achievements, things all become team sports. Maybe your team did amazingly well and you did poorly, or you made heroic contributions to a doomed project. All that can really be added to a resume past a certain point is association and (perceived) input, that you were on a project that succeeded, maybe in leadership, but even then luck might have played more of a factor. One common way to evaluate this is with a counterfactual, i.e. using the ‘alternative universe’ approach of causal inference work.
One cannot judge a performance in any given field by the results, but by the costs of the alternative (i.e. if history played out in a different way). – Nassim Nicholas Taleb (Fooled by Randomness)
Let’s ignore perception for now, and focus on self-created benchmarks. Identifying the right skill gap is a major part of the work, so it’s helpful to have clear feedback or some form of evaluation framework. Your skills and deliberate practice habits are more so something you can control than the environment (including the skill of finding an environment you can thrive in). These need to be organized and have clear boundaries, since in a job value creation is more important than what skill you used with regards to impact on meaningful work.
If you can’t solve a problem, then there is an easier problem you can’t solve: find it. – George Polya
Skills require direct experience to develop, but experience doesn’t necessarily mean those skills improve, especially after a certain amount of experience, and measurement can get trickier over time. Mastery will plateau over time without practice. This is where you have to figure out how well you want to maintain an earned skill, or if you want to rebuild it when you get ‘out of shape,’ or even when you decide you want to continue improving despite diminishing returns as a passion. Sometimes it’s okay to let a skill get rusty because the environment doesn’t require it anymore, when someone can’t do that, I would argue it can reflect a form of trauma (e.g. if someone thinks they need to be in control all the time).
The major mastery benchmark that is commonly known is the ‘10,000 hour rule of greatness’ established by Malcolm Gladwell to be considered ‘elite’ in a field. At a workplace, that comes to about 5 years at a job (40 hours a week x 50 weeks a year x 5 years) – assuming deliberate effort and improvements are possible – maybe in some fields it takes 10 years because half the work is menial or repetitive, and perhaps this is not transferable to other jobs or environments, but you are likely one of the best at that job in that company if you kept working at it and weren’t just ‘spinning your wheels’ or ‘going through the motions.’
If you can’t explain it, you don’t understand it. – The 5 Elements of Effective Thinking
Another common benchmark is the first 90 days of getting established at a new role. I usually say for tech jobs it takes about 3 months to ramp up to a new job (feel competent with the product, data, etc), 6 months to become more confident (which is a thousand hours give or take), a year to say ‘okay I got this’ and two years to really feel strong and start looking for more challenges. Typically I’ve found that every two years things tend to change, whether it’s a new job, a new perspective, leadership or team changes, or just changing focus (e.g. to go from DS to more MLE or PM skills). Even years into a role however, you can still learn a lot from seeing the consequences of major decisions from the past.
For more immediate feedback, I’ve recently developed my own benchmark that I’ll call the ‘6 times in 2 months rule’ where after six hour-long practice sessions (about one per week) over 2 months I start to see noticeable improvements in my skill level (whether new or getting ‘back in shape’). Specifically this came for me from rock climbing with a friend where things suddenly started to click and had the grip strength to be able to utilize skills I had developed elsewhere (e.g. non-grip related strength). Let’s call this the ‘inflection point in the skill curve’ for me, where the improvement starts to compound and practice gets really fun. Less than six practice sessions over two months and I never reach a critical mass – I keep starting over. Six sessions in a few weeks and I don’t really digest the learnings or recover fully and I start to burn out and give up (unless I have little else going on, nothing else to balance, or am extremely motivated). This benchmark also works for me with getting ‘back into shape’ for interviews or case studies after years of being out of practice.
This is probably different for everyone and varies by skills, etc – but the ‘magic moment’ framework is a helpful concept for motivation as something to work towards that is not so immediate as ‘today’ or ‘this week’ and not so distant as ‘10,000 hours’. More of a ‘Once a week, for 3 out of 4 weeks for 2 months and then things will start getting fun’ moment.
EDIT: Three followup stories about plateaus (which could be re-branded as growth mindset stories):
1. The progression of Tetris world records (17 min): https://youtu.be/GuJ5UuknsHU?si=ZywserQA8xGE7VGX
2. Success disease…. When you reach a large goal, or finally get to the top, the distractions and new assumptions can be dizzying. First comes heightened confidence, followed quickly by overconfidence, arrogance and a sense that ‘we’ve mastered it, we’ve figured it out, we’re golden.’ But the gold can tarnish quickly. Mastery requires endless remastery. In fact, I don’t believe there is ever true mastery. It is a process, not a destination. That’s what few winners realize and explains to some degree why repeating is so difficult. Having triumphed, winners come to believe that the process of mastery is concluded and that they are its proud new owners. Success disease makes people begin to forgo to different degrees the effort, focus, discipline, teaching, teamwork, learning, and attention to detail that brought mastery and its progeny, success. The hunger is diminished, even removed in some people….. and an assumption that you can win at will, turn it on when it counts. The time to turn it on and leave it on is before it counts.
– The Score Takes Care of Itself by Bill Walsh
3. Dara Torres. I believe she is the greatest Olympic athlete in the past 100+ years. I swam competitively in high school/college and followed a lot of swimmers and was a huge fan of Dara Torres since she swam the same event as me (50m freestyle). She made it to 3 olympics (’84, ’88, ’92) and set a few world records before retiring from swimming at age 25. She then took a break for SEVEN years and made a comeback at 33 in 2000 – not only qualifying for the Olympics, but earning 5 medals! This is the swim equivalent of breaking the 4 minute mile in running (and IMO puts her in the same league of Michael Jordan, Muhammed Ali, Tiger Woods in terms of comebacks). Keep in mind, almost no one ever made it past a few years out of college in the history of competitive swimming. Without Torres, Michael Phelps retires after the 2008 Beijing Olympics (around age 23) and doesn’t earn 12 of his 28 medals (because why would he keep competing?) – he never becomes the most decorated Olympic athlete of all time. BUT SHE AINT DONE YET. In 2008 at age 41 (2 years after giving birth to her first child) she qualifies for her FIFTH Olympics and ends up with the silver medal in the 50M free by 0.01 seconds (the smallest measured margin in a race) – ending her career with 12 Olympics medals over 24 years. Lowkey even crazier, she actually almost makes it again in the 2012 US Olympic trials where she got 4th place at age 45 (top 2 qualify). TL:DR; In the competitive swimming world, Dara Torres broke the age equivalent of the 4 minute mile in running… TWICE. She completely changed the landscape of Olympic careers (swimming or otherwise). Impact: she made me believe I could keep getting better at things long after I previously thought I would peak.
Daeus Jorento 