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.
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.
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.
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.
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.
I would take it one step up and say if you don't design your life intentionally your career will.
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’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.
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
Does this apply in chaotic context ? I can't foresee what jobs there will be in 2 years now.
> 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]
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.
Its that time of the year again huh. The times for unfilled news years aspirations.
“Ok Greg”
“I’m not defined by my career Greg”
“Greg see a therapist”
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 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.
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'd more say: if you don't care about your career yourself - someone else with interest conflicts will
This reminds on the sentence of a former boss, who said: "if you do not take care of your money, someone else will do"
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.
“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.
> 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
Here's my two cents: career-driven people are assholes.
You're welcome.
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.
[dead]
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/