> 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.
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.
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.
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 it 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.
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.
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.
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.
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.
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.
The job market and my visa status meant that it's either impossible or I need to make significant sacrifices.
So that's life.
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.
Reminds me of PG's "How To Do What You Love"[1]
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.
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'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.
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.
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.
"If you don't have your own story, you become part of someone else's."
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.
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.
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
Can this ever be enough?
I am not sure. Is this even possible in current feudal corporate structures? I did spoke with some people from my work. One was afraid for his job because of another employee. Other was afraid of reorg and if there will be lay-offs. Another company and the merger there caused one guy to be afraid of loosing his job because system he build will be discontinued. Maybe their current position is not the career they really want and after the setback, they are afraid off, they will be able to advance it further in the direction they are actually aiming for... but what if not? What if they will never will be able to advance it further? What if they will never will be get back up?
At some point the only direction you can go is down. Is this all?
Even if you will be able to build your own company things may go wrong and you may loose it. Economy can change. Market can change. Your company may be bought or taken over. Nothing is truly sure.
Should you not invest in the carrier then? No, this is wrong. If you will not set course for you someone else will. And you may not like the place when you will end up. Setting up your own goals is very good practice.
But I am not sure if this should be your life goal because this is so dependent on so many variables. Variables you have absolutely no impact on. And with that uncertainty comes stress. I think that your life goals should be set to something that depends only, or almost only on you.
If they realize that the company cannot provide what you are looking for then they may not want to invest more resources in keeping you around, or keeping you happy. If they realize that you find some sort of intrinsic reward in certain work, then they might put you last for raises, because the money could help them more when spent on other people.
It's best to selectively reveal only your immediate short-term goals, only at the current company, and only as part of an ask. Always make them pay for information, if you are going to reveal what you want, then they need to reveal whether they intend to help you or hinder you in getting it. Slow answers, non-answers, pushing to next quarter, etc. All signal that they intend to hinder. It's rare to get an honest, fast "no".
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.
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
“I’m not defined by my career Greg”
“Greg see a therapist”
You're welcome.
English Version (clean, correct, humorous) “Whoever ignores success because it doesn’t count as a mistake will make very little progress.”
The “Little Brother” Misassessment Now, bro once said: “If there’s no mistake, then I can’t learn anything from it. Without a mistake, there’s nothing to learn.”
But if his recipe for success - all the right, good, subtle, less noticeable things - isn’t even registered by his mind...
…then isn’t that a problem with the mental template he’s using?
“Fixed points of social polarization”...
Hey bro, before I hug you as the “Hero of Labor” - sincerely, warmly - 2,800 hours of work this year...
Tell me honestly: Did only you earn that praise, or do the employees of high‑performers like you also deserve some recognition?
I probably don’t know them - but I do know you, which is why I’m asking.
Self‑reflection: Learning also comes from questioning routine Keyword: Extremes (Mistake vs. Non‑Mistake)
Thesis: “You only learn from mistakes.” Antithesis: “Then I must be a genius, considering how often I mess things up…” Paradox: “If you never see success, you can’t do anything wrong.”
The “Little Brother” misjudgment is ultimately a cognitive trap. It reduces learning to mistakes and filters out success, cooperation, and quiet contributions.
The Mistake Olympics Gold for the colleague who filled the coffee machine with dish soap. Bronze for the intern - eventually you only learn how to apologize.
Punchline: “I don’t make mistakes - I produce learning material.”
“My success is invisible, boss, because - as I’d like to emphasize - I couldn’t possibly have done anything wrong.”
“Hero of labor? I’m a hero of coffee breaks. Without me, there wouldn’t be any work at all.”
“If mistakes were the only source of learning, my life would count as a Harvard degree.”
Whoever ignores success because it doesn’t count as a mistake will make very little progress.
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hoped that it adds something ...useful...nor... hahaha!