7 ms·

A Forty-Year Career (2019)

149 points by alexzeitler 4y ago

angarg12 4y ago
I really like all of Will Larson content, and this one post is a gold mine. I always recommend to mentees early in their career. I find the sections about Pace and Prestige particularly insightful. Unfortunately during the last decade+ we haven't really talked that much about long careers in tech. Instead it's been mostly about FIRE, or people quitting the industry due to burnout. When instead of thinking how can you make the most money to quit your job the fastest, you think how you can sustain and grow in your job the longest, the whole framing of your career changes. I personally joined the industry because I love tech, and imagine myself working on it on some form for a really long time. At the same time I have been burn out more than once (this is actually and ongoing issue) so more discussion on how to handle career long term is appreciated.
- itronitron 4y ago
  Well, for many people, FIRE means Forced Into Retirement Early so the retire early with financial independence is really the only winning strategy.
  - intelVISA 4y ago
    I'd retire but I don't want to deprive the tech world of my works of art (microsauvice-spaghetti au cloud) /s
- deleted 4y ago
  [deleted]
derekisnt 4y ago
Great post, thanks for sharing Alex!
aschearer 4y ago
Good post. There's an interesting tension in software between the cynical and idealistic. On the one hand, there's the notion that writing software is a craft and that what we're doing has an aesthetic component. On the other hand there's a mercenary attitude; we're guns for hire, here to make our fortune, and our loyalty to the job lasts only as long as the paychecks clear.
- ipaddr 4y ago
  I see it more as realist vs idealist. We need to get this done vs we need the highest quality code base
- owlglass 4y ago
  While loyalty to the craft can have the side effect of generating more value to an employer, I don't think the two notions are antagonists. Get better at your craft and you'll have more opportunity to operate as a mercenary.
  - aschearer 4y ago
    Perhaps you're right. Perhaps I am being to literal in my comparison, but I see tension when I compare craftspeople of the past / other industries with our own. Instead of honing our skills under an expert for many years, we swap jobs and even sub-disciplines frequently. Can we cultivate "craftsmanship" in that manner?
  - intelVISA 4y ago
    A crafts-merc is the ideal, a pure merc won't contribute beautiful code and a pure crafter won't grasp the business value of their elegant monads.
karaterobot 4y ago
> Meeting my new coworkers, they structured their jobs as lottery tickets bought with their lifeblood, trading tips on managing the symptoms of work until the pearly gates of liquidity opened. That's a true statement and a painful insight.
- mynameishere 4y ago
  It's five mixed metaphors is what it is.
  - sdwr 4y ago
    Hey, you can lead a horse to water, but you can't make it switch mid-stream.
    - ggm 4y ago
      "You can lead a whore to culture, but you can't make her think." Dorothy Parker, reputedly.
  - SamvitJ 4y ago
    "Lottery tickets", "lifeblood", "symptoms of work", "pearly gates of liquidity" I count four. Curious, what's the fifth? Your comment made me realize that it's quite an interesting sentence.
    - andrewjl 4y ago
      > structured Probably this
influx 4y ago
Will Larson was one of the favorite people I met at Uber, and when he left, it was much darker.
- dllthomas 4y ago
  I have fond memories of him across the foosball table.
bruce343434 4y ago
> At Digg, one mentor gave me the savvy advice that the fastest path to financial success was working for four years at three different just-about-to-IPO companies. A surefire way to retire by forty. (This is, for the record, pretty good advice.) Why is it good advice? What is the context in which it operates?
- ioblomov 4y ago
  At venture-funded startups, a generous portion of compensation will be equity. And four years typically allows said equity to vest fully.
  - LanceH 4y ago
    Yea, all you have to do is pick three consecutive winners.
    - jfk13 4y ago
      Which is trivial, with hindsight. Less so in the moment. You could equally well pick three failures, and end up with close to nothing.
      - jacobr1 4y ago
        Your odds are much better with 3 companies, that one might succeed. Especially if you are joining late-stage startups. But at the same time, your equity package will be smaller, so the exit won't be as impactful.
    - vvG94KbDUtRa 4y ago
      [dead]
- ggm 4y ago
  Retiring at 40 is not always good. Being able to retire at 40 is of course stress reducing, because you can stop worrying a bit. Actually stopping might not be a good idea: Rates of depression and disease in retired people are not just a function of "being old" -being unoccupied and inactive also play a part.
markus_zhang 4y ago
I think the tip for 40 yr old FIRE is still gold. At 40 I'm mostly bored by work and just want more time for myself. My regret is that I messed up most of my time pre 35 so missed tons of chance. But still cherish what I have right now.
- lotsofpulp 4y ago
  This one? > At Digg, one mentor gave me the savvy advice that the fastest path to financial success was working for four years at three different just-about-to-IPO companies. A surefire way to retire by forty. (This is, for the record, pretty good advice.) I don’t think it has been applicable for many years.
  - markus_zhang 4y ago
    I think timing and connections are important. Very difficult to get right. Anyway I'm pretty far from the "core" of the crowd.
  - ericmcer 4y ago
    It was super applicable just 3 years ago, anyone who hopped into zoom/snowflake/mongodb had a nice few years.
    - lotsofpulp 4y ago
      I thought for the past decade or more now, the “surefire” way to FIRE was to work at a big publicly traded tech company and keep frivolous expenses low, and a few million by 40 would have been nearly guaranteed (since you are earning a couple hundred thousand or more per year). Marry a similar high earner to make it even more guaranteed.
    - majormajor 4y ago
      Do you have specifics on size of equity grants and timings and levels? There are lots of recent counter-examples; I have a relative who joined Uber shortly before IPO, he didn't get much. The pre-IPO valuation was already high and there were enough employees that grant sizes were not large. Even joining Zoom/Snowflake/Mongo seems like you would've had to time it very well to make sure you got in before the peak and vested in time to sell before the fall. Some other googling of recent tech IPOs shows a lot of drops: HashiCorp, Confluent, Monday.com, Squarespace... do you retire if you join companies like that just before IPO a few times in a row?
burnte 4y ago
This made me think, I'm 45 right now, and this week is 30 years working in IT for pay, not a hobby. If I'm still in tech (which I don't see that changing too much) I'll have a 40 year career at 55. If I retire at 65, that'll be 50 YEARS in tech. Wild how time both flies and stacks up.
- stcroixx 4y ago
  Do yo see many 55-65 year olds doing technical work at your company? Or any company you’ve been at in the past?
  - mixmastamyk 4y ago
    Why wouldn’t you, other than ageism? How about other professionals like lawyers and doctors?
    - majormajor 4y ago
      In software development the other big elephant in the room is the age of the field itself. If the world thirty years ago needed fewer software developers, then you'd have fewer 20 year old new software developers - and that strongly reduces the odds of having as many 50 year old developers today as 20 year old developers today.
      - mixmastamyk 4y ago
        If your definition is focused on javascript slingers, ok. But it’s been ~eighty years since WWII and the Top Secret Rosies and Bletchley Park. Business and govts got the on board with automation early. Population has vastly increased as well, which affects all professions.
        majormajor 4y ago
        80 years is a very young profession, still. How long have their been lawyers training in university programs? Doctors? The answer is in centuries and so you'd expect a lot more supply/demand equilibrium. How many times has that automation resulted in the business saying "great, things are easier" instead of "great, that's quicker now, let's do more things with the time we freed up?" I've only seen the latter, which just breeds more* need for more automation. You can see it in how much software the average business employee used 40 years ago vs today, even halfway through your timeline.
DubiousPusher 4y ago
IDK. This seems like good advice for a particular kind of person. One who is content for the vast majority of their human experience to revolve around software and technology. All these side gigs add up and this looks like a life with very little time to broaden oneself. Either that or this person has somehow found the golden ticket of a boss that actually considers career development as something they are willing to pay salary for. I would have to do these kind of things on the side and I don't want my whole intellectual inner life and my hobbies to become software. I don't want to write software blogs in the evening. I want to read history books and cook dinner. I don't want to do podcasts on Saturday. I want to tear the drywall off my entryway and frame in a new window. I don't want to do side hustle paperwork on Sunday. I want to teach my kid how to shoot. I don't want to take a day off to go to a developer meetup. I want to go march for Medicare.
- EdgarVerona 4y ago
  Agreed with your concerns, though to me it sounds like this guy in the article is also trying to limit his hours spent on learning and side projects outside of work, which is healthy. But I think the case you bring up is more interesting and prevalent in our field. I used to be the guy who lived in software development. Lived as in spent every waking moment doing something with development, including working stupid hours that in retrospect could not possibly have been productive. I woke up one morning and I was 30 years old, divorced in large part because I lived at work, had developed diabetes because I didn't take care of my body, and almost friendless because I chose my computer over my friendships nearly every time. That wasn't living. When I finally woke up I realized that I had wasted my 20's: I was an addict getting a fix, not some genius reaching enlightenment. Maybe some people are able to do both, but when I had that realization I decided to leave my software endeavors at work unless I knew it was a side project of a very short duration. If I wasn't being paid at my 40 hour a week - and not more than 40 hour a week - job, I needed to actively resist plunging into it as a default rather than vice versa. As a result of this, I know I have become a worse engineer. But I also have a wife and kids, several hobbies, friends I care about who care about me, and while my health will never fully recover from developing diabetes I would say that I am in astonishingly better health than I was at 30. I will take that over my addiction to the software treadmill.
deleted 4y ago
[deleted]
clemailacct1 4y ago
In my experience the biggest challenge isn’t just identifying that pacing is important (because the author’s section on Pace is a complete gold mine of wisdom) - it’s having your direct manager and/or the company culture support that. He correctly states that you should ‘change your situation’ (your job) if you’re not allowed to pace appropriately - but there’s a real tangible risk to getting recruited if your resume paints you to look like a mercenary who leaves every year. Again, it just feels fuzzy and not black and white. Really great read though!
- JohnFen 4y ago
  > there’s a real tangible risk to getting recruited if your resume paints you to look like a mercenary who leaves every year. Yearly would be a bit much, but every 3-5 years isn't really that big of a deal.

149 points by alexzeitler 4y ago

I really like all of Will Larson content, and this one post is a gold mine. I always recommend to mentees early in their career. I find the sections about Pace and Prestige particularly insightful. Unfortunately during the last decade+ we haven't really talked that much about long careers in tech. Instead it's been mostly about FIRE, or people quitting the industry due to burnout. When instead of thinking how can you make the most money to quit your job the fastest, you think how you can sustain and grow in your job the longest, the whole framing of your career changes. I personally joined the industry because I love tech, and imagine myself working on it on some form for a really long time. At the same time I have been burn out more than once (this is actually and ongoing issue) so more discussion on how to handle career long term is appreciated.

itronitron 4y ago
Well, for many people, FIRE means Forced Into Retirement Early so the retire early with financial independence is really the only winning strategy.
- intelVISA 4y ago
  I'd retire but I don't want to deprive the tech world of my works of art (microsauvice-spaghetti au cloud) /s
deleted 4y ago
[deleted]

derekisnt 4y ago

Great post, thanks for sharing Alex!

aschearer 4y ago

Good post. There's an interesting tension in software between the cynical and idealistic. On the one hand, there's the notion that writing software is a craft and that what we're doing has an aesthetic component. On the other hand there's a mercenary attitude; we're guns for hire, here to make our fortune, and our loyalty to the job lasts only as long as the paychecks clear.

ipaddr 4y ago
I see it more as realist vs idealist. We need to get this done vs we need the highest quality code base
owlglass 4y ago
While loyalty to the craft can have the side effect of generating more value to an employer, I don't think the two notions are antagonists. Get better at your craft and you'll have more opportunity to operate as a mercenary.
- aschearer 4y ago
  Perhaps you're right. Perhaps I am being to literal in my comparison, but I see tension when I compare craftspeople of the past / other industries with our own. Instead of honing our skills under an expert for many years, we swap jobs and even sub-disciplines frequently. Can we cultivate "craftsmanship" in that manner?
- intelVISA 4y ago
  A crafts-merc is the ideal, a pure merc won't contribute beautiful code and a pure crafter won't grasp the business value of their elegant monads.

karaterobot 4y ago

> Meeting my new coworkers, they structured their jobs as lottery tickets bought with their lifeblood, trading tips on managing the symptoms of work until the pearly gates of liquidity opened. That's a true statement and a painful insight.

mynameishere 4y ago
It's five mixed metaphors is what it is.
- sdwr 4y ago
  Hey, you can lead a horse to water, but you can't make it switch mid-stream.
  - ggm 4y ago
    "You can lead a whore to culture, but you can't make her think." Dorothy Parker, reputedly.
- SamvitJ 4y ago
  "Lottery tickets", "lifeblood", "symptoms of work", "pearly gates of liquidity" I count four. Curious, what's the fifth? Your comment made me realize that it's quite an interesting sentence.
  - andrewjl 4y ago
    > structured Probably this

influx 4y ago

Will Larson was one of the favorite people I met at Uber, and when he left, it was much darker.

dllthomas 4y ago
I have fond memories of him across the foosball table.

bruce343434 4y ago

> At Digg, one mentor gave me the savvy advice that the fastest path to financial success was working for four years at three different just-about-to-IPO companies. A surefire way to retire by forty. (This is, for the record, pretty good advice.) Why is it good advice? What is the context in which it operates?

ioblomov 4y ago
At venture-funded startups, a generous portion of compensation will be equity. And four years typically allows said equity to vest fully.
- LanceH 4y ago
  Yea, all you have to do is pick three consecutive winners.
  - jfk13 4y ago
    Which is trivial, with hindsight. Less so in the moment. You could equally well pick three failures, and end up with close to nothing.
    - jacobr1 4y ago
      Your odds are much better with 3 companies, that one might succeed. Especially if you are joining late-stage startups. But at the same time, your equity package will be smaller, so the exit won't be as impactful.
  - vvG94KbDUtRa 4y ago
    [dead]
ggm 4y ago
Retiring at 40 is not always good. Being able to retire at 40 is of course stress reducing, because you can stop worrying a bit. Actually stopping might not be a good idea: Rates of depression and disease in retired people are not just a function of "being old" -being unoccupied and inactive also play a part.

markus_zhang 4y ago

I think the tip for 40 yr old FIRE is still gold. At 40 I'm mostly bored by work and just want more time for myself. My regret is that I messed up most of my time pre 35 so missed tons of chance. But still cherish what I have right now.

lotsofpulp 4y ago
This one? > At Digg, one mentor gave me the savvy advice that the fastest path to financial success was working for four years at three different just-about-to-IPO companies. A surefire way to retire by forty. (This is, for the record, pretty good advice.) I don’t think it has been applicable for many years.
- markus_zhang 4y ago
  I think timing and connections are important. Very difficult to get right. Anyway I'm pretty far from the "core" of the crowd.
- ericmcer 4y ago
  It was super applicable just 3 years ago, anyone who hopped into zoom/snowflake/mongodb had a nice few years.
  - lotsofpulp 4y ago
    I thought for the past decade or more now, the “surefire” way to FIRE was to work at a big publicly traded tech company and keep frivolous expenses low, and a few million by 40 would have been nearly guaranteed (since you are earning a couple hundred thousand or more per year). Marry a similar high earner to make it even more guaranteed.
  - majormajor 4y ago
    Do you have specifics on size of equity grants and timings and levels? There are lots of recent counter-examples; I have a relative who joined Uber shortly before IPO, he didn't get much. The pre-IPO valuation was already high and there were enough employees that grant sizes were not large. Even joining Zoom/Snowflake/Mongo seems like you would've had to time it very well to make sure you got in before the peak and vested in time to sell before the fall. Some other googling of recent tech IPOs shows a lot of drops: HashiCorp, Confluent, Monday.com, Squarespace... do you retire if you join companies like that just before IPO a few times in a row?

burnte 4y ago

This made me think, I'm 45 right now, and this week is 30 years working in IT for pay, not a hobby. If I'm still in tech (which I don't see that changing too much) I'll have a 40 year career at 55. If I retire at 65, that'll be 50 YEARS in tech. Wild how time both flies and stacks up.

stcroixx 4y ago
Do yo see many 55-65 year olds doing technical work at your company? Or any company you’ve been at in the past?
- mixmastamyk 4y ago
  Why wouldn’t you, other than ageism? How about other professionals like lawyers and doctors?
  - majormajor 4y ago
    In software development the other big elephant in the room is the age of the field itself. If the world thirty years ago needed fewer software developers, then you'd have fewer 20 year old new software developers - and that strongly reduces the odds of having as many 50 year old developers today as 20 year old developers today.
    - mixmastamyk 4y ago
      If your definition is focused on javascript slingers, ok. But it’s been ~eighty years since WWII and the Top Secret Rosies and Bletchley Park. Business and govts got the on board with automation early. Population has vastly increased as well, which affects all professions.
      - majormajor 4y ago
        80 years is a very young profession, still. How long have their been lawyers training in university programs? Doctors? The answer is in centuries and so you'd expect a lot more supply/demand equilibrium. How many times has that automation resulted in the business saying "great, things are easier" instead of "great, that's quicker now, let's do more things with the time we freed up?" I've only seen the latter, which just breeds more* need for more automation. You can see it in how much software the average business employee used 40 years ago vs today, even halfway through your timeline.

DubiousPusher 4y ago

IDK. This seems like good advice for a particular kind of person. One who is content for the vast majority of their human experience to revolve around software and technology. All these side gigs add up and this looks like a life with very little time to broaden oneself. Either that or this person has somehow found the golden ticket of a boss that actually considers career development as something they are willing to pay salary for. I would have to do these kind of things on the side and I don't want my whole intellectual inner life and my hobbies to become software. I don't want to write software blogs in the evening. I want to read history books and cook dinner. I don't want to do podcasts on Saturday. I want to tear the drywall off my entryway and frame in a new window. I don't want to do side hustle paperwork on Sunday. I want to teach my kid how to shoot. I don't want to take a day off to go to a developer meetup. I want to go march for Medicare.

EdgarVerona 4y ago
Agreed with your concerns, though to me it sounds like this guy in the article is also trying to limit his hours spent on learning and side projects outside of work, which is healthy. But I think the case you bring up is more interesting and prevalent in our field. I used to be the guy who lived in software development. Lived as in spent every waking moment doing something with development, including working stupid hours that in retrospect could not possibly have been productive. I woke up one morning and I was 30 years old, divorced in large part because I lived at work, had developed diabetes because I didn't take care of my body, and almost friendless because I chose my computer over my friendships nearly every time. That wasn't living. When I finally woke up I realized that I had wasted my 20's: I was an addict getting a fix, not some genius reaching enlightenment. Maybe some people are able to do both, but when I had that realization I decided to leave my software endeavors at work unless I knew it was a side project of a very short duration. If I wasn't being paid at my 40 hour a week - and not more than 40 hour a week - job, I needed to actively resist plunging into it as a default rather than vice versa. As a result of this, I know I have become a worse engineer. But I also have a wife and kids, several hobbies, friends I care about who care about me, and while my health will never fully recover from developing diabetes I would say that I am in astonishingly better health than I was at 30. I will take that over my addiction to the software treadmill.

deleted 4y ago

[deleted]

clemailacct1 4y ago

In my experience the biggest challenge isn’t just identifying that pacing is important (because the author’s section on Pace is a complete gold mine of wisdom) - it’s having your direct manager and/or the company culture support that. He correctly states that you should ‘change your situation’ (your job) if you’re not allowed to pace appropriately - but there’s a real tangible risk to getting recruited if your resume paints you to look like a mercenary who leaves every year. Again, it just feels fuzzy and not black and white. Really great read though!

JohnFen 4y ago
> there’s a real tangible risk to getting recruited if your resume paints you to look like a mercenary who leaves every year. Yearly would be a bit much, but every 3-5 years isn't really that big of a deal.