If you don't design your career, someone else will (2014)
gregmckeown.com280 points by TheAlchemist 7 hours ago
280 points by TheAlchemist 7 hours ago
My favorite lens on this comes from Hamming:
> It is well known the drunken sailor whos taggers to the left or right n independent random steps will, on the average, end up about sqrt(n) steps from the origin. But if there is a pretty girl in one direction, then his steps will tend to go in that direction and he will go a distance proportional to n. In a lifetime of many, many independent choices, small and large, a career with a vision will get you a distance proportional to n, while no vision will get you only the distance sqrt(n). In a sense, the main difference between those who go far and those who do not is some people have a vision and others do not and therefore can only react to the current events as they happen.
Just a tiny bit of bias towards a direction will get you very far very fast.
I once modeled+visualised this with a bit of javascript[1] and it's quite surprising to see the huge difference from even a tiny multiplication factor on each random/probabilistic decision.
Hamming was also writing from a highly privileged position. He was able to work at Bell Labs for the majority of his career. That just doesn’t exist today.
The Art of Doing Science and Engineering is a great book but it needs context. The last edition was released in 1994. Programmers had a lot of labour power back then.
Today though? The median house costs more than a third of the median income. Inflation has raised costs of living to unsustainable levels. And for programmers there have been hundreds of thousands of layoffs since 2023 and a low number of job openings.
I don’t think it’s unreasonable to take what job you can get or stay in a job you don’t care for until the trade winds return.
> Programmers had a lot of labour power back then.
Huh? Back then, there was very little glamor to software engineering. Computing just wasn't serious enough. There was relatively little competition, salaries were unremarkable, and sure, you could land a job for life, but that still exists today. If you are an IT guy for a lumber mill or a local hospital, it's not going to be as cutthroat as Big Tech. It's just that you're not gonna be making millions.
We're pretending that this type of cozy tech jobs don't exist anymore, but they do. They just don't come with IPOs and RSUs.
This is a framing issue. You can't control the times, but good advice is applicable in good and bad times. If Hamming was operating from a "good time", it should be true that his policies are also applicable in the "bad times".
His advice to "work on the worlds hardest problems" was spoken to people who had worked their way past the initial difficulties. General advice to "Move towards important problems", which is precisely the same thing, applies in good and bad times, and is very likely to produce in you a valuable expertise.
It's not about good or bad times. All compasses are broken so any particular direction you believe you are walking deliberately might as well be uniformly random.
"Direction" and "design" are probably the wrong metaphors for careers.
>I don’t think it’s unreasonable to take what job you can get or stay in a job you don’t care for until the trade winds return.
Having a goal does not seem at all at odds with weathering a storm. Your choices can then be what you learn in your free time, or what horizontal moves you make at that job, or which people you get closer to, for example.
> Hamming was also writing from a highly privileged position.
Hamming had a lot of career capital. He was the only person in the world with his track record. If you needed his kind of research/output/teaching/etc, he was the person you needed.
Cal Newport talks a lot about this. Great books.
Have something [unique/valuable] to offer and you'll be surprised how many doors it opens. Yes it takes time to stairstep your way there. A fresh grad has less career capital than a seasoned engineer with a track record of building billion dollar companies.
Is this still a valuable read today (specially taking it into account)? It's been in my reading list for a while now but I'm always postponing :|
I read/skimmed it this year. I don't feel it was worth it. The first few and last few chapters have some nuggets but for the most part it's pretty highly technical stuff that feels not super relevant or interesting for a software engineer today (in my opinion).
That's really nice, but the point where the vision is should move too. You learn as you progress. What you enjoy changes. The entire industry moves. Being focused on the goal you defined 30 years ago is almost certainly wrong for most people.
After ~15 years, I've realized that no good things come to you without sustained focus / attentiveness, and gentle pressure in the direction of attention. What everyone here is saying is "be closed loop", vs the drunkards "open loop". Combined with a bit of progress every day, it's (so far, at least) magical what happens.
Another bit to consider: It took a long time to realize that basically everyone wants basically everyone to succeed, as long as incentives align. It was very easy to imagine I was swimming upstream early in my career - especially my early mentors urging me to specialize to find success. My initial temptation was to "specialize" in hot/attractive topics in an effort to be the "indispensable X authority". But my PhD advisor urged me to "not swim in red water", where the incentives are inherently conflicting - everyone wants to be "the X person".
Much better to find a team working on a good problem somewhat like the ones you want to solve and just push along with them. You can save yourself a lot of energy by slotting yourself into a system that aligns with your preferred direction of travel, even if only a little bit. The current carries you.
I always wondered about that.
Seemed like everyone was doing topics in the “red water” and felt useless to not.
I found my areas of interest were the “red water” of 20 years prior and there was little left and it didn’t solve problems relevant to industry.
Quit PhD and got a job where I was grossly underpaid until the next one.
I literally fell into anti-fraud and email security back in 2012 and spent a totally unexpected chunk of my career around those topics.
The amount of people I've heard of say they want to go into email security is very small.
I think this demostrates a far more important perspective than "have a vision" - which is easy to explain and almost impossible to execute, which is be curious, intentional and open to lots of things. The curious & open part leads you to new oppportunities, and the intentional part helps you figure out how to evaluate & where to go next.
This sounds like much better advice. Trying to plan out a tech career over decades seems like very premature optimizing. Being curious and making sure you keep learning is not only very pleasant, it’s useful. And when the tech changes, fine, no problem. Most of the big features of my life have not been plannable ahead of time.
I can’t emphasize this enough. Every 5 years or so I reassess what my goals are and refocus my vision on where I want to apply my skills.
Things change fast in our industry so being able to pivot to something nearby is paramount for maintaining a career in this field.
Not everyone has the fortune to spend 15 years at a FAANG or other large corporation. Sometimes you have to build it.
Every five years or so, my wife asks me, "What do you need to learn now for the next five years of your career?"
It's the same as what you do, except I need the reminder...
>>Being focused on the goal you defined 30 years ago is almost certainly wrong for most people.
I think there are certain things that are not likely to change, and must be aimed for. For starters, being healthy, proactively working towards a retirement nest egg, so that you don't end up homeless and starving in case things go south too fast.
There are many such things I hold as things I would want several years from now. Good health, free time and enough money to not need a job to just put food on the table, and a roof above my head.
>> Good health, free time and enough money to not need a job to just put food on the table, and a roof above my head.
Sound like the utility function for a lot of people I would say.
Do people actually perform a random walk though? All terrain - both metaphorically and physically - is not equal, so wouldn't a more accurate description be 1. float on the water and go where the current/tides take you, or 2. decide when you're going to paddle against it towards the lighthouse? or more simply, "most people walk downhill"?
This is a lovely mental model and also makes me feel a host of existential dread. I had a semblance of vision before gen AI and I think that vision needs serious revision
Which is fine. Goals shift and can even completely disappear, forcing you to pick another one. But having and pursuing long term goals at most times is still the ticket for success. My 2c.
It is not something I share very often, because people assume a lot when I do, but von Braun[1] shared a similar idea. Ignoring for a moment his past, one cannot say that he had no achievements further supporting position noted by OP.
https://en.wikipedia.org/wiki/I_Aim_at_the_Stars
> Despite his moral quandaries, von Braun participates in the Nazi's V-2 rocket program during World War II to further his ambitions in rocket engineering. The film carefully depicts his efforts to reconcile his love for scientific exploration with the knowledge that his work is being used for destructive purposes.
I have a similar short story idea where a person of the calibre of Elon Musk who works so hard is made to feel and see his successful moonshot projects being used for destroying and subjugating nations. This would be similar to Oppenheimer. Another twist I can take with the story is Hero "Elon" knows about this outcome but still in the hope of change in institutional ideology over decades hopes for better use for his technology. In the movie Watchmen, Ozymandias feels the pain of millions he is going to kill to save future billions.
Watchmen: Killing millions to save billions
I don't think jus the raw distance (from here) is the metric to necessarily optimize for. It may be more useful to throughly search the nearby area, for example - especially if you feel you're in a good neighborhood already.
https://www.sciencenews.org/article/sharks-use-math-hunt
A new study suggests that some sharks and other marine predators can follow strict mathematical strategies when foraging for dinner. The work, reported online June 9 in Nature, is the latest aiming to show whether animals sometimes move in a pattern called a Lévy walk.
Unlike random motion — in which animals take similar-sized steps in any direction, like a drunk stumbling around — Lévy walks are punctuated by rare, long forays in any direction. Draw a Lévy walk on a graph, and its squiggly pattern echoes a fractal, the mathematical phenomenon whose shape remains similar no matter the viewing scale.
It's a lovely metaphor, but I find myself at odds with the logic. What you sacrifice with vision I think is flexibility to respond to serendipity.
Vision is not a dictator, it's just having half an idea of where you'd love to be in X years.
It can and probably will move as you age and gain experience.
But if you're thinking you'd love to be your own boss and, as you have that vision, you find something much more interesting, you can still re-assess.
This resonates with me.
Three years ago, I left academia after finishing my PhD in Economics, frustrated by how little real-world impact my hard work seemed to have. I moved into IT, wanting to build things that would be more immediately useful and practical. Still, the dream of using science to create positive change never left me.
I was invited to work with AI at a company that develops software for the public sector. It wasn't the dream (I wouldn't be using my academic expertise) but it felt like a step closer. At least I'd be providing tools to support people who directly affect others' lives. From the start, I told my boss that I hoped someday to offer not just AI tools, but real socioeconomic statistical analysis as a service for the public sector. And while I've been happy working with AI, I've always sought out opportunities on projects that were more data-driven.
Three years later, some clients expressed interest in having our AI chatbot provide real-world socioeconomic data analysis. My boss just gave me a promotion to lead both the AI team and this new socioeconomic data initiative.
I was reflecting the other day on how fortunate I am, my dream "chased me." But it wasn't simply luck. I had always stayed attuned to the opportunities that arose.
That's a good point. I find it very hard to find the optimum balance between flexbility / vision.
Don't let optimum be the enemy of good and enjoy the ride.
My entire professional life/career has been a tension between trying new things/opportunities and trying to be intentional in what/where/when/how I make changes. I'll probably be done in about 10 years so I'll let you know how it worked out then.
Great point, and great blog post (as usual).
PS Tangent - FYI there's a typo "Minset" should be "Mindset" in the reference to your book. HTH
I also really treasure that quote. Your visualization really made it hit home again though.
It does make me reflect on this piece I wrote 9(!!) years ago though, which hasn't completely materialized. I think I'm due for a re-alignment of priorities.
I have generally had strong vision in my career but this year due to external forces at play at work I have been much more reactive to the chaos and generally felt off the whole year, this was a nice mental model to step through, liked the visualization.
I think the beauty of this quote is working more than its content.
Most people, even when they do not sit down and think about it, follow one of the two career paths:
- Some people will actively pursue the next logical progression (senior, lead/manager, head/vp, exec).
- Some will happily stay in their position unless the next one is offered to them.
Being deliberate will always work better compared to being random, but it is not like all people who succeed in their careers deliberately planned to get where they are.
I would even guess that for the vast majority of successful careers, competency and luck played a much bigger role than being deliberate about it.
I never really had a plan for a career but I never settled. I borderline almost did at my last job as it paid enough and I loved the people like family but the move from that job landed me in the most interesting and well paying job I've had yet. Luck totally played a part in most of my jumps and the ones I thought were good were often bad and the ones I wasn't interested in ended up being the most interesting.
> would even guess that for the vast majority of successful careers, competency and luck played a much bigger role than being deliberate about it.
I think this is true. I had a while where my career was doing really well constant steps up, I was learning, getting promoted, was working on great projects and problems that were engaging and led to easy promotions. Then I got a new manager and it was downhill. Then I got a new job and the problems are insignificant and there's no room for growth of any kind. If my latest job was earlier in my career my career would be very different.
Wait, are you saying that for a symmetrical random walk, the expected distance is of the order of sqrt(n), but even for a slightly biased random walk (like 0.5000001 chance to take right) it's of the order of n?
Edit: well of course it is. I was thinking expected position (which should be 0) not distance
yep
"expected distance" is average abs(coordinate), so for biased walk (and big enough time) it's simply abs(bias)*time, and for unbiased it's deviation==sqrt(variance)
The “expected distance” is not what you think here.
For a binomial distribution of probability p and (1-p), after N steps the expectation value of right steps is Np.
The Variance is Np(1-p), so the standard deviation (or Root-Mean-Square) scales as Sqrt(N).
That's basically diffusion versus drift.
But I think it is the wrong view, as generally people do move into the direction they want to go. Take a person doing plumbing but wanting to be in art. The problem is not the direction, the problem is taking the first step.
In general, many people dislike changing jobs, so they don't take steps. The steps are the problem, not the direction.
You don’t know anyone in your life that “talks big game?
Or someone else that “can’t get their stuff together?”
A lot of people never even “move”.
Drift made me think of electron drift under applied voltage or electric field.
The vision doesn't have to be accurate, it just has to be directional
This reminds me of a take on art, that goes something like "you don't need talent, but you do need to have taste". Taste is the same kind of driver as direction in this case.
Probably butchered the quote, can't remember who said it, but the message stuck.
Taken out of context, this line seems like a valid description of our ethos these days lol.
The general sentiment of being aware about your career and decisions is true.
But this reminds me of what I hate about modern corporate “culture” the most. And what is broken about it the most.
Im speaking about the rat race. Tge fact, that you have to waste a noticeable part of your work time, effort and energy to sell your work instead of doing it. To the point where good salesmen make a “career” and become your bosses without any correlation to their work abilities or even management skills. Those are very good at designing their careers.
As a result the more corrupted the company with this style of internal management the more reliable it drowns in a swamp of ineffectiveness.
In a well functioning company or society “building a career” shouldn’t be a goal nor priority. It should be the natural outcome (more or less) of a “job very well done” that is a true priority.
Yes we’re not in a perfect world. But at least we should try to reach our ideals rather than promoting rat race mentality as a norm.
> To the point where good salesmen make a “career” and become your bosses without any correlation to their work abilities or even management skills.
The few times I've seen this actually happen at a company, it was not the kind of company I wanted to work for long-term anyway.
If the company is so broken that the wrong people are being promoted while the right people are being ignored constantly, there will be bigger problems than you simply missing a promotion.
The one startup I worked for that had this problem chronically (combined with some nepotism) did a bee-line run straight for insolvency and then collapsed. Everyone on the ground floor saw it coming. Some people still tried to race for promotions and upward career trajectory there, but the smart ones invested their effort in getting out.
That said, I've also worked at some companies where the right people were getting promoted but there were groups of people with sour grapes he were always upset it wasn't them. It's never something everyone agrees on.
The main thing missing from this IMO is an element of chance or randomness, the ability to incorporate “unknown unknowns” into your life. The most interesting people I’ve come across have had a variety of jobs, many of which they knew absolutely nothing about when starting out. There is a genuine value add when you’ve worked beyond the same white collar profession your entire working career.
In other words, the problem in designing your life is that you’re almost always going to pick things you already know. Maybe that gets you to the peak of your current profession over twenty years…but maybe some other job is actually a lot more fulfilling to you.
I’m not sure how to incorporate this into a young person’s real life experience, but I do think gap years, varied internships, volunteering, etc. are probably a good start.
I recently listened to a podcast with a guy that wrote a book advocating that young people spend 4 years getting a pilot’s license, working on a ranch, becoming an EMT, and various other useful skills/jobs. That seems like a great idea, although I didn’t like the hostility to traditional college he had in offering this plan.
In Quebec we have a sort of college between high school and university where you are forced to take "bullshit classes" along with the stuff you chose to study. Mine included philosophy, Spanish, photography, canoeing, and a few others. At the time it felt like a diversion, but it was a welcome introduction to something other than computer science.
In my first year of university, a senior grabbed me by the shoulders and told me that I _have_ to try an internship or semester abroad. One thing led to another and I have just celebrated 10 years in Germany. It led to my current career, which is not at all what I studied.
To answer your question, I think that it requires a certain curiosity, and an appetite for experimentation. I feel like the system is teaching kids the opposite of that.
I wish cegep, or an interstitial school where you have a year or 2 to just take tons of unrelated courses, was more common. So much focus is put on universities as job training that they lose a part of what historically has long made them special --- learning for the sake or learning.
>The main thing missing from this IMO is an element of chance or randomness, the ability to incorporate “unknown unknowns” into your life.
100% this. When I started working in recruitment, it was literally intended to be a temporary means to an end. I stumbled across Hacker News back in 2010 and accidentally uncovered a niche (tech startups) that has resulted in a career where over the past 15 years has evolved into holding VP level roles at YC startups to now running my own successful recruitment and HR advisory business for startups. I can legitimately attribute that entire path and growth to accidentally stumbling across this website and couldn't possibly have guessed the impact it would ultimately have on my career.
In a society where everything needs to be optimal, randomness is seen as a mistake.
And that’s the tragedy. It should be viewed as a feature, not the bug. Curiosity and willingness to mix it up is where the serious innovation resides. Cross cutting concepts more easily happen when you’ve done/experienced/seen/felt different stuff … period.
I tell my son all the time that I couldn’t predict what I’m doing now … 3 years prior. I didn’t have this insight or awareness but after running the SW/IT marathon for 25 years here we are. Trust your instincts, they weren’t developed in a vacuum. The more you explore, the more insights pop in your mind and every 3 years or so, a change presents itself for you to affirm or deny.
Yeah and even if you’re totally uninterested in “having an interesting life” and just want to maximize income/job prospects, I think you can make the argument that a little bit of randomness is actually the optimal path because it increases your luck surface area.
For example - working in a well-rated fine dining restaurant over a summer while you’re studying computer science seems totally unrelated and not optimal. But maybe that unique experience is what stands out on your resume, and maybe the knowledge about wine or food you acquired there builds a connection with an investor or manager, years down the line.
Another way to put it: don't focus on distance but more on behaving in tune with yourself.
Do you have a link to that podcast? Sounds interesting!
I forget the exact podcast, as I think he did a few different interviews. Might have been this one?
https://www.artofmanliness.com/people/fatherhood/podcast-108...
The book itself is called The Preparation.
If you design your career, you will almost certainly get the same outcome too.
I've managed people for decades and this has been a common pattern. I'd have people come to me with their plans to be in the C-suite in five or ten years, based precisely on self-help advice like that. None of them ended up there. But several of the people who never had a plan did in fact end up as VPs, CTOs, etc.
I don't want to say that thinking about your career doesn't matter. It's definitely easy to self-sabotage it by sticking to your comfort zone for life. But turn-by-turn plans are not useful because a lot of our career paths is a product of chance. In a corporate setting, the best advice is just: get in the habit of solving tough problems for the people who matter, and find low-key ways to let them know about the good work you're doing. The rest, more or less, follows from that.
This advice remains relevant but I think it misses an important nuance about how career design actually works in practice. The metaphor of "design" implies you're building something from scratch with full control, but career development is more like gardening - you can influence conditions but not force outcomes.
The key insight is recognizing the misalignment between your goals and your manager's goals. Your manager optimizes for team output and organizational needs. Your career growth is a secondary concern - important, but not primary. This creates a fundamental principal-agent problem. The solution isn't to become adversarial, it's to be explicit about your goals and negotiate actively rather than hoping they'll be noticed.
Practically, this means: (1) Having quarterly conversations where you explicitly state "I want to work on X technology" or "I'm aiming for senior by Q3" rather than assuming good work will be rewarded automatically. (2) Building skills outside your job scope through side projects, open source, or internal tools that solve real problems. (3) Being willing to change companies when growth stalls - the biggest salary/title jumps come from job changes, not promotions.
The dangerous flip side is over-optimization. I've seen engineers obsess over "career design" to the point where they won't touch any task that doesn't directly ladder to their promotion case. That creates fragile specialists who can't adapt when their niche technology becomes obsolete. Better approach: have a direction, but maintain broad skills and genuine curiosity. The most interesting career paths come from unexpected opportunities you recognized because you had wide exposure, not rigid planning.
I do something similar for development of me as a human being. I ask myself how can I improve, what kind of person do I want to be, how can I help make the world a better place.
My "career" is just a means to an end to put food on the table. Also being in my 30s I think I have mostly maxed it out anyway. Sure I might increase my wage a little bit but all in all as for being an IC it is a good as it gets. Sure there is always room for improvement but I am already constantly the person with the most technical skills in the room so it would not grant me any benefit.
I don't think your "career" needs to be a major focus in your life once you are set up at least. Especially if you don't do any meaningful work that actually helps people like being a doctor or teacher or something.
In the end my work just makes someone else richer, it doesn't have any meaning. It does not make the world a better place. Probably a worse place sometimes. I just do it to not starve.
> In the end my work just makes someone else richer, it doesn't have any meaning.
This is something I struggle with a lot. I left companies before, because the job felt meaningless and making some rich guy richer doesn't sound meaningful to me. I am trying to come up with a business idea I can work on on the side, that actually is supposed to make the world a better place, but I am struggling to find anything I have enough experience in to pursue.
I am leaning towards activism now, because that is probably the most achievable thing to do for me. Just building info sites nobody reads, trying to make non tech people aware about how Amazon, Google and so on makes life worse for everyone. Or how anti privacy laws are probably a bad idea.
But that does not feel fruitful either. My everyday life is consumed by the desire of having some kind of impact, making the world better.
> But that does not feel fruitful either. My everyday life is consumed by the desire of having some kind of impact, making the world better.
It nearly impossible to achieve substantial change alone. The key is to be organized with others, to find a community.
Now, I don't mean joining a political party, especially not at first. That can be important work but also very soul crushing
I am talking grassroots-level, local groups that work on a concrete topic, preferable something that concerns you personally. It is important to get into doing things as quickly as possible, be it organizing a small protest or maybe just a get together.
With this you will gain practically experience and you will find other people that share your goals and with whom you will struggle together.
Now, for the long term, you will also need to actually read political theory, you will have to get organized with people that have a more concrete strategy on how to create change but I generally would urge you to avoid analysis paralysis and focus on gaining practical experience first.
Building community is really the key.
I'm trying to avoid community unfortunately. I was never really accepted anywhere, whether is be online spaces or irl and I am not the person to socialize and do stuff with people. Also don't want to rely on people or having people rely on me.
> trying to make non tech people aware about how Amazon, Google and so on makes life worse for everyone. Or how anti privacy laws are probably a bad idea.
I think a majority of people already know this, that's why it feels fruitless. Also more negativity ("these companies are bad because of x, y, z") will also make you feel negative.
Why not make those sites, talk to those non-techy people, but provide _some_ form of thing they can do to make an impact in a tangible way, not just "don't use amazon", links to sites that put together local info for small areas, catagories of smaller online sites that you can use instead of amazon or something.
> My everyday life is consumed by the desire of having some kind of impact, making the world better.
Do you have something tangible you can look back on that you did last week that helped achieve this vision? If not, what small thing can you do this week?
> Do you have something tangible you can look back on that you did last week that helped achieve this vision? If not, what small thing can you do this week?
Not too sure, I am pretty delusional about the impact part. I want to achieve something big but have zero ideas on what I could start with. I have a ton of time and want to use it for something I actually believe in, the difficulty is in finding something I actually believe in...
From the perspective of someone in their late 20s, the timing of this article feels quite off when entering 2026. The reality has become far different from the gist of what is presented here.
Career paths and opportunities have been getting broken and changing so much in recent years that I find it hard to plan anything. I don't even know what kind of "goal" is sustainable, let alone what the path towards it is.
The only sensible career that seems to offer a steady trajectory is medicine. Apart from that, my most successful peers were the ones that followed immediate money and speed-ran into owning some kind of real estate, which is a game changer. Besides that, people try to do as many side hustles as possible and diversify their income to save as much as they can and brace for a possible recession. I find it hard to apply any of these 8 steps in such volatile reality.
Deliberate planning is great but serendipity is important too. Some of the richest people I know made most of their wealth as a consequence of being in a position to act* when opportunities presented themselves.
My guess is that it's important not to be overly focused on the intermediate goals and the more debt you have the less able you feel to take risks.
*it may be more appropriate to say start than act as in the two cases that immediately come to mind they were both 10+ year journeys.
This is a very "live to work" article.
Is it wrong to have your career on autopilot if you are satisfied with your job? Clearly, the author wasn't, switching from law to becoming a teacher/writer. So I guess that the article makes sense in this context.
> This is a very "live to work" article.
That's not the impression I got. It's about wanting a career that's meaningful to you. Whatever that means to you. Maybe your answer to "What would I do in my career if I could do anything?" is working 9-5 without a care in the world. That's totally valid.
I can want a decent work/life balance, but I also want to not be in a dead-end job. I can give some thought to my career (not being on total autopilot), and also have my job in balance with the rest of my life.
I would take it one step up and say if you don't design your life intentionally your career will.
Juniors fall into this pitfall so quick. Our newest hire actually set boundaries early on and I was pleasantly surprised
Disagree. This kind of comment is furtively pulling up the ladder behind you. Do as I say not as I do. Junior is the time to learn as much as possible and take risky bets (and suffer accordingly). When I was in a junior in a factory, the night shift knew me well. Nowadays, I've pared it back to 50 or so hours per week, because I now have a family, which is fine but it came at the cost of basically zero time to learn or do things other than what my manager asks.
This is a correct view point to have.
As you get to the downswing of your career, you should have already worked and made enough mistakes to have most of your experience. You must cruise on that experience when you are older.
When you are old, that is not the time to work and make mistakes.
That is, most of the heavy work must be done as early as you can. Eat that frog.
I agree. When new programmers come from uni they sometimes barely did any programming. So at some time in their life they got to actually put in the time and learn how to be a competent developer. It is obviously great if you can do it on somebody else dime in a 9 to 5 but if you can’t get that you should just put in the time and learn. In the end you can at best get paid for the value you can create and if you are incompetent that is not going to be a lot
So it's the kind of work place where you have to set boundaries? :)
We work in different timezones so it's a mess. Either people give up their morning or they give up their evening time.
I'm at the bottom of the chain here and have no authority to change this. Given that I'm being let go soon there's not much reason for them to care about my mental state either.
But from the time I've been here, yes, you need to set boundaries or they'll do it for you. It seems like most PMs are used to talking to robots, because that's how they talk to us lately.
You need to set your bounds in every single workplace, because no one workplace can set the right boundaries for everyone.
“Set your own boundaries, or someone else will do it for you”
Turtles all the way down
I think this mostly speaks about setting boundaries with your higher-up, which is revolved around you.
So, I guess it would be "Turtles all the way up"
Statements like this one come for a position of privilege, which is to be expected on a forum like this one targeting techies who are most probably solidly middle-class, but just wanted to point that out. More exactly, most of the (normal) people are NOT in the position of designing their lives, believing otherwise is, again, tainted by said position of privilege.
You either misunderstood or we disagree fundamentally. Everyone can and should design their life. Of course richer people have a lot more choices, and poorer people a lot more constraints, but everyone can make informed choices.
Believing "most of the normal people" have no agency is condescending.
Oh they have agency. They also have bills to pay, families to take care of and many other obligations that folks of privilege do not need to be bothered with. It is immediately obvious how privileged we are compared to many others who are not a liberty of designing their lives or careers.
>They also have bills to pay, families to take care of and many other obligations
I honestly don't get your point. I also have bills to pay and a family to take care of. Almost everyone does. I can't just quit my job and spend my life sunbathing on a sunny island, even though that sounds way better than my office job.
The number of people who have so much that they don't ever need to worry about bills or affording a family is tiny, even among HN users. This is also not what "designing your life" is about.
To be clear, I acknowledge my privilege - I have a relatively high salary (but not US-high, not even 6 USD figures) and don't need to worry about day-to-day survival. I just fundamentally disagree that there is some threshold below which people can't make decisions about their own life or career.
I don't think it's condescending to believe a large number of people mostly cannot design their lives. At best they can try to make it better for their children, if at all.
Why is this condescending? It's not their fault, it's how the system works and their bad luck in not being born into a more privileged position. For people who cannot make ends meet, trying to make ends meet takes most of their available time and energy, there's not much left to ponder about life's choices.
What it is, in my opinion, is terribly unfair. I agree with the GP commenter that us here mostly ignore this reality. And that's OK, clearly TFA is aimed at privileged people like us, not most people.
I never considered that angle because no one ever explained it to me. It feels like this "privilege" concept explains a great deal about society. It is like a master key.
Someone recently told me about Jesus and the fact that he died to cleanse my sins. I never heard that one before either.
This reads a bit like classic self-help, but there's a solid point hiding underneath the platitudes. Most careers do get shaped by inertia: the projects you say yes to, the skills you accidentally accumulate, the expectations other people quietly set for you
I find that's a good reason, other than looking for an increase in salary, to seek out new employment opportunities every few years, while nudging your resume more towards the career you want rather than the career you've experienced.
I’ve spent my career chasing jobs that had kept me employed for over 20 years so I can support a family. Unfortunately I have had to let the ‘system’ take me where I am needed so I can pay my bills. It is life.
In regards to the review part:
What helps me is keeping around my TODO.txt month by month, as well as a lot of screenshots and images of the things I find relevant for sharing in stand ups and meetings and such (as well as presentations).
So if I need to review the past month/year (e.g. when I want to update CV/site or catch up with management), it’s just a matter of going through a bunch of text and images without a lot of unnecessary fluff, like digging through Jira. Maybe if I want to get the approximate time/effort spent on particular stuff, based on the amount of activity there.
Alongside that, it’s also nice to document stuff that was particularly good, or all the ways software broke in (and what broke how often), as well as stuff that pissed me off and made me want to quit (sometimes people/mindsets, sometimes tangible code or practices).
When the default is just going with the flow and not documenting anything and doing no self reflection, every improvement upon that helps.
GPT was actually pretty good for this use case until 5.2 kneecapped its long term memory and now its more aggressive about pruning ( very annoying as wide recall now has to be explicitly invoked ).
Very interesting! Do you organize screenshots and images by day and by topic?
Currently not really, at least not for the weekly status meetings.
Typically I'll have a folder with a bunch of numbered files in the order that I want to talk about them, since it's easier to just quickly share my screen and run through then when I want to let others know what I've done, for example along the lines of:
01-migrate-gulp-grunt-to-vite.png
02-vue-prebuild-script-check-unused-translations.png
03-java-add-compile-memory-limit-ide.png
04-server-update-python-for-ansible.png
...
So a bit of my thoughts + open to suggestions from other folks on HN.
I've been a DevOps/SRE essentially my entire career and almost always in Finance (banks, FinTech startups, multiple hedge funds etc) and most recently in crypto.
It's seemed that for SWEs the path was always something like:
- junior
- team lead
- manager
- manager of managers
- CTO (or VP of Engineering etc)
For SREs/DevOps it always felt a bit fuzzier after manager and most of the manager of managers I know ended up being that role in an "infra" department (e.g. k8s, networking etc).
I would love to know what folks with my background ended up doing later in their careers/age mid 40s and above?
(all of this is even more fuzzy due to LLMs/AI and part of me feels like it's time to start pivoting into some kind of IRL service or manufacturing role given the speed at which things are developing. e.g. maybe I should buy a bakery...)
Open to all kinds of stories and suggestions here as would most likely benefit me and also lots of other folks reading the comments.
> I would love to know what folks with my background ended up doing later in their careers/age mid 40s and above?
I'm 41 now, started working in education but pivoted back to tech quickly (DevOps specifically) since tech is a better match for me.
After a few years, fell upwards into management then pivoted into Technical Program Management roles where I've remained since. Love this since I get to interact with teams of people working in my program(s) but don't have the responsibilities of a people manager.
Personally, my roles focus on infrastructure and things at least loosely related to my DevOps background. Worked at two blockchain companies (I've been into blockchain tech since 2012) but considering moving into green energy somehow.
I think in most cases including yours: choose roles based both on interest and total compensation. And it's a lot easier to get roles (especially TPM roles) if you're already technically competent in that particular field (in your case FinTech and crypto).
> We have a sense of what we would most love to do but we immediately push it aside. Why? Typically because “it is not realistic” which is code for, “I can’t make money doing this.”
Reminds me of PG's "How To Do What You Love"[1]
Yeah totally. Someone should totally have designed their career in marketing pre AI and not change course. They are in control. There are no outside forces.
I worked very hard for the first 5 or 6 years of my career - hit senior dev pretty quick, managed to double my pay moving into consultancy, and back on product dev in a smaller company nowadays.
Honestly? I don't feel a massive need to grow beyond where I am. I earn in the top 5% in my country. I live a comfortable and flexible life. I continue to learn like any dev with a passion for technology does - but i'm not constructing my life around an endless climb. If my role naturally transitions upwardly, great. If I stay where I am, steadily taking on more responsibility,that's also totally fine. The diminishing returns of chasing a CTO title or another arbritrarily large sum of money just doesn't seem worth it.
I can’t say I’ve ever had “5 year plans” and even I did, facts on the ground change so fast, my plans would change.
I’ve been working since 1996. But without going into ancient history, in 2008, I had spent the last 9 years at my second job, became an expert beginner, been divorced for two years, and had 5 mortgages between my home and two rental properties that were underwater by about a $250K.
I was also teaching fitness classes part time to make up the gap - that was suppose just be a hobby.
Then my plan was to get out from under all of that mess. I didn’t know how or have a timeline. But it started with getting a job where I could get exposed to modern development practices (done after 3 months and a lot of prep work), stopped teaching so much (just kept my favorite classes where my friends were), and walked away from five mortgages and wrecked my credit (everyone was doing “strategic defaults” back then).
One thing I didn’t “plan” for was to meet and marry my future wife and become a father to pre-teens by 2013. I’m still married, boys are grown. That by itself changed my goals.
By 2013, I was still about 25% under paid even for an enterprise “senior” [sic] dev in Atlanta and still digging myself out of my financial mess while supporting a family.
My goal by then was to develop the soft skills and hard skills to be a team lead - again no timeline.
Then in 2016, my goal was for us to move and work for a much better paying tech company after 2020 when my youngest graduated from high school. Even that changed to I would rather just not move and get into customer facing cloud consulting (not staff aug) after 2020 when I thought I would have to travel a lot (who could have predicted a worldwide pandemic??).
Well both fell into my lap in mid 2020 - customer facing cloud consulting and BigTech and I didn’t have to move when I got a job at AWS working in Professional Services. I didn’t even know the department existed. Again not planned.
2020 my plan was to work for Amazon for four years, pay off debt, save some money and work for a smaller consulting firm. I knew three months after I got there that I definitely didn’t have the stomach for BigTech long term. This was the only 5 year plan that worked out more or less as I wanted (staff consultant for a reputable mid sized company).
Even then, I never thought in 5 years, we would decide to sell our house in the burbs, downsize and move to state tax free, much better weather Florida
I planned to get out of my current company and stop wasting my life two years ago.
The job market and my visa status meant that it's either impossible or I need to make significant sacrifices.
So that's life.
Wondering if working as a contractor is any different. you won't stay longer than 6-12 months on a project and you can safely say goodbye without having to explain a gap in your resume
Why didn’t you make the significant sacrifices?
This is one of those areas where family starts to influence decisions. My wife and I had kids between 24 and 28. From that point forward, 'supporting the family' took priority over personal fulfillment.
Now that our kids are grown and self-supporting, it's wild how much simpler the risk calculation is. But at 52 with engineering manager being the dominant role in my CV, not particularly appealing to the small companies making big moves that I'm interested in.
I have a really hard time designing my career in tech because I believe that people already have more options than they need or can afford.
What people need aren't more options. What they need is MONEY; which is the ability to obtain the options which exist. And the only way to give people more money is through political means. This is why I was interested in crypto; it seemed to get straight to the point...
I later quit crypto due to too much corruption in the space and launched a mainstream startup with a co-founder centered around helping people find 'the perfect job' but I quit as co-founder because the idea of it almost makes me want to vomit now.
The system is firing people en masse. The system itself doesn't want people to have jobs... So me, trying to work against the system by offering a solution that operates within the system feels futile and like gaslighting users and myself. It's selling a dream. There is no perfect job. Reality is our socio-economic system doesn't even have a shitty job for you... Let alone a perfect job... And most jobs seem like bullshit jobs anyway.
It's extremely hard to find an idea that's both truly useful and profitable these days. That's a shame because that's exactly what I want to do with my life but I feel like this does not align with what is possible within the current system. I cannot find any such opportunities in the tech sector.
Someone told me I should get into politics but again if I think about what the typical politician does, I feel nauseous. The only kind of politician I could possibly be is the honest kind that gets assassinated... And of course I don't want that. Besides, nobody would fund me... My hitman would probably have an easier time raising funding to 'take me out' of politics than I would raising funding to get into it.
I resonate so much with you. I'm in the middle of getting my product out for people to use and naively kept thinking that a good product means people are interested.
I need to integrate with tools that prematurely deny me because I'm not a big company. I basically already lost, despite my tool being much more reasonable and maintainable (I've worked at the competitors and it was a mess).
The world doesn't care about good products, they just care about how it looks. Big companies look good, you don't. It got me demotivated early on. You really need thick skin to start selling a product.
Your last paragraph is an interesting way to frame it.
I also think it's true; what appeals to people is something superficial. The product has to be highly optimized to generate an initial 'wow' factor. But it's almost impossible to create such 'wow' factor without sacrificing something fundamental about the product.
The goal is to make such a good first impression that people will pay for your product and then will keep convincing themselves and their friends that your product is great... When it's not because actually there are many better alternatives out there which are higher quality and provide more flexibility.
Among financially successful products, I see a lot of rigid, inflexible, low-quality products. They create a 'wow' factor by removing complexity; also removing flexibility... Targeting a specific psychological bias... These products seem 'easy' and magical at first but what makes them easy also makes them inflexible and fundamentally useless. Because flexibility is what gives a competitive edge... But flexibility also scares people away.
I have also fallen in this trap by thinking that a good product that addresses the needs of users would make it wanted. But coming so far with no traction to show I seriously doubt my prospects of bridging the gap between from the needs to the wants.
Great feedback. Many of us are on auto-pilot and taking a little bit of time to reflect, can shape a better version of that auto-pilot.
Another useful input is what are other people telling you? This shaped my career early on by either taking on the work others didn't want to do, or hearing others mention what they felt was important and focusing on this.
An underappreciated factor for building one's career is also building a safety net, because that allows for risk. Having that safety net means you can't be taken hostage in a salary negotiation, and it means that you can entertain riskier career moves. That safety net contains financial and (demonstrable) human capital.
A lot of us live our lives according to the expectations of others (our parents, society, etc) because this is all we know how to do at first and what the "system" reinforces through school, career, etc. and this difference between what we want to do and what we actually end up doing can end up causing lots of suffering to ourselves (and to others).
I've seen fear as the primary obstacle to trying something different when the current route is not working. It's really hard to step outside the comfort zone in those situations.
My 2c as someone who has ended up in a non-traditional career track, mostly doing my own thing and getting paid for it.
While you definitely need a higher than average tolerance for uncertainty, the big thing is just not seeing all the options. Many choices are occluded by the options presented to you by employers, the educational system, etc. The spectrum of careers, which is a continuous higher-dimensional blob of "things you can do to make money", is systematized in such a way that while there are paths to unusual career outcomes, most of those paths can not be expressed.
You may on some level want to reach some career or lifestyle goal, but often the path to that destination isn't obvious, and it's definitely never presented to you as an option among the things you can choose, and more than likely you'll have few if any role models or people to ask for guidance if you find yourself on that track.
Not just fear of failure, but fear of disappointing people, losing status, or admitting (to yourself and others) that the plan you’ve been following isn't actually working
Its that time of the year again huh. The times for unfilled news years aspirations.
I don't think the random sailor analogy is a perfect fit.
If you guide your own direction too strictly you will both risk moving yourself into a dead end, but also miss out on unexpected opportunities.
But your opportunities depend partially on what you can actually do. In other words, optmize for your strengths, refine what works, remove what doesn't. Opportunities will come, but if you are not prepared based on your own predispositions, they are wasted on you anyway. Direction of the sailor of the sailor is but one factor in this.
I'd more say: if you don't care about your career yourself - someone else with interest conflicts will
Kinda reminds me of an interesting scene from the Netflix series "Castlevania"
"If you don't have your own story, you become part of someone else's."
I enjoyed this article and think it's good advice, and I also think that the punchline (title + last sentence) is wrong. Not that it makes a big difference, I just treasure texts more that I feel the author thought through to the last detail.
If you don't design your career, in most cases I guess no one will. In the comments are good examples, like the random walk of the drunken sailor. The cases in which you could use the phrase "someone else designed it for me" in a meaningful way seem rather rare to me.
Does this apply in chaotic context ? I can't foresee what jobs there will be in 2 years now.
“The crime which bankrupts men and nations is that of turning aside from one’s main purpose to serve a job here and there.”
As a former career contractor who took probably 7 commercial jobs I didn’t care about for every 1 creative job I wanted to do but for which I was underpaid, this feels deeply true.
This reminds on the sentence of a former boss, who said: "if you do not take care of your money, someone else will do"
> Many years ago I followed this process and, without exaggeration, it changed the course of my life. The insight I gained led me to quit law school, leave England and move to America and start down the path as a teacher and author. You’re reading this because of that choice. It remains the single most important career decision of my life
That "decision" required a safety net most will never have
Designing your career isn’t about self introspection, it’s about leverage
And leverage is stolen from the invisible hands that keep your world running while you journal
The problem isn't individual, but systemic: why is the freedom to choose rationed so narrowly?
For a lot of people, work isn't a career to design, it's survival math
“Ok Greg”
“I’m not defined by my career Greg”
“Greg see a therapist”
When I buy clothes, I always “choose” the outfit the mannequin is already wearing.
Also see Feedback Analysis, by Peter Drucker from Managing Oneself - https://hbr.org/2005/01/managing-oneself
No one else will.
Here's my two cents: career-driven people are assholes.
You're welcome.
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