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.

[1] https://swizec.com/blog/your-career-needs-a-vision/

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.

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.

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 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.

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.

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.

I would take it one step up and say if you don't design your life intentionally your career will.

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 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

> 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

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.

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.

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 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.

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.

> 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]

[1] https://paulgraham.com/love.html

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.

I just want to be left alone, without doing the corporate dances. I don’t care about your company, your culture, and your unique DNA. The only family I have is back home, so just let me do my work for 8-9 hours a day, and leave me alone.

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.

Also see Feedback Analysis, by Peter Drucker from Managing Oneself - https://hbr.org/2005/01/managing-oneself

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.

Its that time of the year again huh. The times for unfilled news years aspirations.

I tried the exercise. It turned into a mess. I seem to only want to escape employment. Everything I "wanted" to do seemed to be a deflection from the fact that I have anxiety about my job, staying relevant, staying employed, hamstering enough money to clear out my debts when the competition or AI inevitably beat me.

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."

https://www.youtube.com/watch?v=-MofDRVtRec

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 be the only one burnt out on trying to design my career. especially these days when things outside your control just keep making it harder and harder (bad job market).

Reminds me of https://fs.blog/hunter-s-thompson-to-hume-logan/

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.

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.

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

“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.

There is a lot of luck involved too, the conditions we are born, family ,people we are friends with early on and so on, just because there are few outliers does not everyone can follow same.

It's worth mentioning that career conversations with your manager are always bullshit. How could they not be? Your manager's incentives are to keep you around, keep you productive, and keep you inexpensive. It's ridiculous to think that helping you build a successful career, which likely doesn't involve them or your current employer for very long, is something that they would do. Why would you reveal any information about your long term plans to such an adversary?

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".

I understand that and I agree. Though I think the real question is what you would do when you will achieve this goal. What then? Will you be happy? What you will do with the money? Will this amount be enough?

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.

This reminds on the sentence of a former boss, who said: "if you do not take care of your money, someone else will do"

No one else will.

Does this apply in chaotic context ? I can't foresee what jobs there will be in 2 years now.

if you dont live your life, some one will !! if you dont eat your food some one will !!

“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.

I measure success by the number of rabbit holes I step over.

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.

Nope. It is not that black & white. It is always a mix of contextual changes and your decisions that are going define your path. Too much action on your own is also not going to help. In some cases, people who just didn't do a thing in decades, have achieved better that people who did all acrobatics.

Here's my two cents: career-driven people are assholes.

You're welcome.

+++ Non native english speaker, machine-edited text +++

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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Because modern smartphones can do way too much.

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“Since I started using the one‑button phone, I actually know what my friends look like.” - A convinced ex‑smartphone addict

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Because sometimes less is simply… less.

+++

hoped that it adds something ...useful...nor... hahaha!

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