Ask HN: What's the biggest risk you took in your career that paid off? - ruffrey
======
kinai
Quit my "dream job", sold/gave away everything I owned, just hopped on a plane
to a new continent (Wednesday last day at work, Thursday morning flight went)
and see how it goes. First week I sat mostly alone around at some beach,
contemplating about what I had done and whether it was the stupidest thing
ever. It was a personal challenge. Best decision of my life. That was nearly 3
years ago now.

One can only grow if faced with challenges. I learned a lot about myself and
life.

~~~
iamcreasy
Where did you go? Would you mind sharing what you have learned?

~~~
kinai
I learned to be grateful and enjoy the small things in life, to worry less, to
calm my mind (which is still a challenge) and to not overthink everything.

It sounds very generic, but putting in words how your character changed is not
so easy, I figure I'd have to ask family/old friends.

------
foxhop
Deciding to finally start demanding bigger raises from my employers by firing
them and joining new companies.

~~~
Pirate-of-SV
How do you do this exactly? Do you threaten to leave if you dont get X in
salary or is it more implicit that you quit and the next company give you a
salary that is closer to X than the previous?

~~~
foxhop
No, I just leave. In the last 4 years I have tripled my salary.

At a lot of companies there is a a max promotion of like 10-15% - often times
companies will only give 3-5% increases, I deal with that once and then move
on.

I've gotten 30% increases each time I leave.

My mantra has become, "The only way up is out"

That said, I have a "remote only" policy, I don't entertain relocating (I have
two houses in my town) and I have already tried and left both of the local
industries in close proximity after getting "stuck".

Reference: [http://russell.ballestrini.net/career-development-is-a-
game-...](http://russell.ballestrini.net/career-development-is-a-game-of-
chutes-and-ladders/)

~~~
bbcbasic
I am guessing your plan presumbly works when either

1\. Engineer is early in their career so lot of scope of raises in early years
by moving. 2\. Market moves and suddenly you are paid below market rates so
you move to level up 3\. You are upskilling or taking on more responsibility
in the move each time.

~~~
nojvek
I work at a well recognized soft company. First year SDE's get paid more than
me with a fat signing bonus because they come from Stanford. I've been working
for 3 years now. 5 years prior experience. As a L1 you don't have much
negotiation leverage.

------
benjohnson
Raising my rates.

I was too timid to rais rates on old clients, so I gave new clients a higher
rate. After a year or so, about 20% of our customers were paying the higher
rate and that gave me the courage to up the rate on the old clients.

Nobody cared - a few customers told me it was about time I raised my rates.

~~~
tajen
Listen up people, that's exactly how you should raise rates: Test with new
customers, then align older ones.

------
tyre
(In reverse chronological order)

1) Quitting ZenPayroll. Ended up leaving what are now millions of dollars of
(paper money and unsellable) shares on the table, at a time when the company
was clearly taking off. Now building a values-focused, mission driven company
the right way and loving every minute of it.

2) Quitting LivingSocial after 11 months when I realized that they weren't
what they sold me on. The pitch was building back-office tools for SMBs, but
in the end they never did the right thing for SMBs if it wasn't also in their
interest.

3) Dropping out of college as a philosophy major, believing I could learn to
program. Joined LivingSocial as an aspiring engineer, which turned out to be a
great place to start. Great exposure to the Ruby community, experience with
hard things (scale, caching, business problems creeping into the product.)

As you may notice, my biggest fear is regretting wasted time. While I tried to
change each one of those places to be what I knew they could be, until you
start your own company you must (rightfully) defer to what others decide is
"right". I've realized I have an incredibly high bar for making difficult
decisions, which isn't realistic to "manage up."

------
saryant
Right out of college I made the huge mistake of joining one of the big
consulting companies. Six months in I hated it so I just quit.

At the time I was living in Houston, where I didn't have much of a network, so
I packed up my stuff and moved back to San Antonio. I attended college in San
Antonio and at least had some contacts there, mostly revolving around the
coworking center Geekdom.

No job but I had enough savings to float myself for a few months.

A friend of mine from there put me in touch with a startup he had invested
in—they were still in Techstars and he knew they needed an engineer. I
contracted with them for a bit and joined up full time after they graduated
and raised a seed round. Arguably they risk was theirs as their first
engineering hire was a fresh dev who'd never had a full time programming job.
They moved to Boulder after the program and six months later I followed.

Now I'm at Twitter, because I quit a job I hated and bet that my contacts
would pay off.

~~~
wallzz
what is was a huge mistake joining big consulting companies, I am working now
at a "big consulting company", I just want to know your point of view.

~~~
saryant
I realized that it was going to take me 5+ years to get to the point with
consulting where I had any control over my own destiny. Jumping to a startup
let me accelerate that timetable and build far more experience far faster than
would be possible within the Capgemini behemoth.

~~~
wallzz
I feel the same way as you did, I have 2 years in a big consulting company
(Atos) , and I really want to get out of here

------
ColCh
Taking dive into fullstack javascript 2 years before!

I picked express, react (v0.9) and sequelize. Webpack for bundling (it was
undocumented that time) It was my first experience with backend JS and react.
For service I used docker and fig (now it's docker-compose)

Of course, I failed this project after 1.5 years of dev (it was pretty huge,
but this technical debt destroyed all that I have coded). Then I created this
project from scratch on Magento (it was just online shop) in about 4 months.

What I learned? A BUNCH of things related to TDD (system tests, unit tests,
mocking), JS ES6, program architecture at overall, SQL (things like
assotiations, migrations, SQL performance optimizing), about caching
technique... This list is pretty huge, I learned in that time 80% of all I
know!

That was about positive moments. Now about negative. I experienced impostor
syndrome (by the way, I'm feeling it right now and this feeling is not leaving
me). Also I experienced burnout 3 times (apathy, lack of appetite, insomnia).
This thing was really destroying....

I'm happy I've failed this project! I learned a lot of things. Now I really
become full-stack JS engineer. I've got the power :)

And First of all, I started to value my time, my energy and my mental and
physical health. Now I place this things in first place, they really matter!
I'm 21 years old, don't take me like I'm sick or something (Like all people on
20s, I'm filled with energy). I just found the price... the price of myself.

------
20years
Took the plunge and left a captive position to freelance. A year into
freelancing (in 2006), I developed my own SaaS service and grew it to $80k
monthly revenue. Did really well until the market crashed in 2008. Built a few
other SaaS services since then with moderate success.

Also started a small advertising agency in 2013 and grew that to $50k monthly
revenue. After 3 years of doing that, I realized that scaling an ad agency was
really hard. There is a lot of over-head, high churn and I didn't enjoy it.

I am now back to developing a mobile app SaaS service and an educational SaaS
service.

To sum it up - my biggest risk that paid off was starting my own business.

~~~
ggggtez
Software as a service service.

~~~
cheiVia0
I know a lot of people like poke fun at "RAS syndrome" but how would you write
this phrase without using a redundant acronym?

"Built a few other SaaS services since then"

Would it be "Built a few other SaaSes since then"? "Built a few other Software
as a Services since then"? "Built a few other SaaServices since then"? "Built
a few other services following the SaaS model since then"?

I can't think of a way that doesn't sound more contrived than the original.

~~~
20years
I agree with you on this. I sometimes describe it as SaaS products but even
that doesn't really feel right. I guess because when I think of a product I
think of something physical.

------
imaginenore
Changing jobs often. Working at the same place for more than 2 years rarely
pays off, even you get glowing reviews and everyone loves you - it doesn't
convert to the dollars. You might get a 10% raise, but you will not get +40%.
Getting comfortable costs you tens of thousands of dollars.

------
JackMorgan
Two big risks. One, I left middle school teaching career to work as an
admissions counselor at my wife's university so we could score free tuition.
When I got fired from that, I applied for a programming job at the same
university. I shouldn't have gotten that job, I was completely unskilled.
Instead they hired me, and so began the most rewarding work of my life!

~~~
msdos
Also genuine question...

How does one get a job when they're completely unskilled?

~~~
csa
Not OP, but I can answer this one.

1\. Many jobs are acquired based on things other than one's skill set. Some
that I've seen: friend, family, lives in the area, internal candidate (so less
process), spouse of current employee, minimally viable candidate that avoids a
public job announcement, need a butt in the seat ASAP or the seat is lost, no
skilled candidate will actually apply for the job (e.g., lower salary, bad
reputation, etc.)... the list could go on and on.

2\. The people doing the hiring might not have had the skill set required to
know that he was unqualified.

3\. He may be sandbagging his own skills. A lot of times the hard part of a
job is problem solving. The tech part, even if he did not know it at the time,
is learnable. The problem-solving part is less easy to teach.

4\. Due to various unofficial policies that exist at places like universities,
there may have been a requirement to find a new place for him when he was
"fired". This could be for a number of reasons. Maybe he was actually laid off
(e.g., reduced budget for that department and he was junior). Maybe he fits a
certain profile that they want to keep at the university (e.g., he's connected
to someone important). Maybe they wanted to avoid a potential lawsuit for
wrongful dismissal.

Having seen a lot of odd stuff happen at well-known universities, I have to
say that my curiosity has been piqued. I hope more of the story is told...

------
alasdair_
Leaving a stable job and many friendships and moving to a new city without
knowing more than one person.

I did this when I moved to London (from Scotland) and then to Seattle and then
the the Bay area.

It was worth it every time but it's scary too, especially when there was no
backup plan - if things didn't work out in London, I had no ability to get
back to Scotland.

------
dhruvkar
Not the biggest risk (as I didn't have much to lose), but right after my
undergrad I took a job in China with a young, 3rd party Quality Control
service company, getting paid about $1200/month + food/housing. I learned the
ins and outs of factory work in China, over a vast number of industries. The
owner invested in his foreign employees learning Mandarin. This year and half
experience paid off since my work now involves buying from China heavily, and
I have insight into this process.

~~~
testpass
Did you graduate from an non-Chinese university, and then move to China? Or
always had an in?

------
trevmckendrick
Quit my job as an accountant at a big firm with no next job or prospects lined
up. Ended up creating a successful iPhone Bible app.

~~~
netskrill
Now you have to deliver on the "accounting for freelancers" course you said
you were going to deliver last year

------
MWil
Graduating law school at peak of last recession - worst employment prospects
in generations, not even close to top of class, only had one summer's worth
experience with public sector (1 month each w/ state DOJ and legislature).

Spent last year in school designing something akin to Casetext, then they came
out of Summer '13 batch while I was studying for the bar. Decided to cheer
them on rather than continue to build my application since I just recently
began self-teaching JS (they're currently like 85/90% parity with my idea, was
closer to 60% when they first came out - go Casetext!)

Joined up with AmeriCorps for 12k/year providing free legal assistance to
homeless/disabled vets (VA bens, discharge upgrades, clearing criminal
records). Had applied to legislature job paying 60k. Fell in love with my vet
work. Legislature job calls me up 4 months later into my AmeriCorps service to
interview (I'm 90% sure I had this in the bag based on the previous summer's
final evaluation).

Turned down interview, stuck it out with low pay for another 6 months and then
got hired on for (still lower than Legislature) salaried position.

1.5 years later - for my org, I'm in charge of all vet work for the whole
state (4th largest vet population in US), I supervise the veteran law program
at a top 15 lawschool. I'm "unofficially" in charge of whole state bar
association of vet law attorneys (we just recently formed as an entity with
100+ members).

I get to work my own hours, I get to choose my own cases. I didn't even know
this was an area of the law I could make a career out of - not a vet myself.

Job satisfaction > pay (plus it'll come in due time)

------
gk1
Quitting a stable job seems to be a recurring theme here.

I, too, quit a cushy and stable engineering job with the Government to join a
marketing agency. Then I quit that a year later, with nothing else lined up.

My only plan was to "consult," but I didn't know exactly what I would consult
on and how I would find clients.

I went through all of my savings and maxed out a credit card (0% introductory
rate) when, in the nick of time, things started falling into place.

It's three years later now. I'm very happy with my career and the lifestyle
I'm able to afford thanks to my income, which is 2x greater than my Gov't and
agency salaries _combined_.

Wasn't easy, though. I wrote about this at greater length here:
[http://www.gkogan.co/blog/how-i-learned-to-get-consulting-
le...](http://www.gkogan.co/blog/how-i-learned-to-get-consulting-leads/)

------
fnaticshank
Just after my undergrad college I joined a startup hoping to learn and grow
exponentially as a developer. The first day of work my girlfriend came to drop
me off and she said, "you are changing your job in next 6 months". And 2
months working in I realized she was right, it was a dying startup with no
future. I kept working hoping I would induce a change and inspire the team.
Six months in I hated it so much and I got so frustrated that I quit.

The first week after quiting I just spent time questioning my decision. But
next couple of weeks I spent time with myself and gained a better perspective
about life and career.

Its been 2.5 months now since I quit. I have saved enough to keep me floating.
And now I am preparing to get into Amazon. Let's see if I nail it.

It was a rightful decision that I took. One thing I did learn is "How not to
run a startup".

~~~
testpass
If you don't mind commenting, what factors made you realize that you hated it
2 months in?

I'm in a similar boat, going to a startup (50~ people, 2.5 years), so this
would be useful :)

------
hijinks
my biggest by far was my first job out of college. I had a lot of Linux
experience and applied for a giant ISP. This was in 2001 so after the dotcom
bust.

I interviewed there on a Friday. The manager comes in last and tells me
everyone liked me and he was going to offer me a role as a mid-level Solaris
admin. I'd skip over the whole route of help desk->jr admin route and go right
into a mid-level role. The only catch was he told me the company was filing
for chapter 11 bankruptcy on Monday.

I took the job hoping I could last there a year. I somehow made it through 2
rounds of layoffs and was there a year where I moved to another small company
as like the whole IT shop that took me to the next level.

------
rfc
I have two: quitting college at the height of the recession (08') and
switching jobs a couple of times in a few years to increase my paycheck 4x.

I hustled my ass off, worked super manual jobs during the day, focused on
networking and skill building at night. Landed a job in tech and continued to
study anything and everything I could. Few years later, in a upper management
role. Best decision ever. I'm learning so much, getting to work on bleeding
edge tech, and getting compensated well. That said, a couple sentences
explaining this path doesn't due justice to how hard it was to get where I'm
at. I didn't get lucky and this path isn't for everyone.

------
guybrushT
Quit a highly paid job with a big company (my decision). Joined a smaller
company (my decision). Found great people to work with (luck) who are humble,
smart and willing to teach - these days I tap dance to work.

------
bjelkeman-again
Quit my job in a company I was co-owner of, which wasn't going anywhere
interesting. Moved country. Took a sabbatical. Studied environmental science
at the university. Met a great person at a conference. Started an open source
organisation together. Now running open source based data services in more
than a dozen African and Asian countries tracking critical infrastructure,
among other things.

~~~
asimuvPR
Really interesting project. Mind if I contact you?

~~~
bjelkeman-again
Please feel free to contact me. Mention this post.

------
aprdm
I've quit a promising career in embedded systems (senior engineer at one of
the biggest companies with all perks), rented my flat and travelled across the
globe to work in a startup as a junior web dev with python 2 years ago.

Changed my life in all aspects. Today I am in yet another country and enjoying
my career so much more.

------
bobwaycott
One morning, I woke up with the realization I hated everything about what I
was doing with my life. I tossed on a pair of jeans, a white t-shirt, and flip
flops, then went into work to quit (I had been in sales for 3.5 years). As
soon as my boss saw me, he knew what was up. We sat and talked for a bit, but
it was mostly a formality.

I had no plan. I had no replacement job lined up. I had little in savings. I
struggled for the next year. I fucked up and lost a lot. But I forcibly put
myself on a path to do something I loved, and invest the time necessary be
good at it. This opened up a world in which I don't hate my work or life,
rarely have a bad day, and typically work no more than half the year.

It was the best decision I ever made, and I've never been happier.

------
vox_mollis
Dropped out of college in order to pursue my own company.

~~~
navaru
same here, tho' I failed 2 times, closing 2 companies, with the accumulated
experience and knowledge the 3rd one is a success so far

~~~
k__
how come you didn't end up with a staggering amount of dept?

I know a few people who had failed companies and all of them hadnt enough
money left to do anything afterwards...

~~~
navaru
All companies were making money, but at some point, because of bad management,
operational costs were too high and we started to lose profits so I decided to
close early to minimise losses.

For example you build a car wash, first year is doing good, then you start to
patch broken things not reinvest in new equipment, clients are not happy, they
leave, you don't care, second year operational costs are almost the same as
income, so you decide you don't want to own a car wash and you close.

------
Bahamut
Leaving a job I liked in DC and a lot of friends in the area for the world of
Bay Area startups and moving to the Valley. Two years later, I am now a much
better developer, and happier person with a lot more control over my future.

------
Walkman
Learned Python in a country where it's not very popular at all. Now I get good
salary for the same reason :) and I have literally no competition when
applying for a job.

~~~
avinassh
Interesting, which company it is?

------
tajen
I left from Europe to Australia because I drank before going to work (Java
dev). Came back 3 years later not only with 7x savings because the startup had
a successful exit, but also with a lifetime more of experience, I've learnt
how startups worked (and Scala and product marketing and open source and HN,
Howdy HN!) and I came back to successfully create mine, and I now own my job.
Oh and it's a good step towards product management which I love.

~~~
wallzz
I am interested in hearing more about your story if you don't mind, from where
did you go ? why did you left ? what your startup is about ?

~~~
tajen
I can't speak much. My Australian startup had this kind of sweeping
confidential agreement (for example customers aren't allowed to talk about the
performance of the products, and I can't tell for employees). Not very clever
on their part in any case, but I prefer not to develop, sorry.

------
snarfy
I relocated to a tech centric part of the country. The cost of living is
higher, but so are salaries and also the quality of life.

~~~
velox_io
Very true, my biggest regret is not doing this sooner!

------
sly010
I would also like to know what was the biggest risk you took in your career
that you ended up regretting?

~~~
karmajunkie
I dropped out of the workforce in 2003 for about a year, after I got laid off
from a startup while I was working remotely from Austin. It was a tough time
to be a somewhat junior developer in Austin, and after a couple of really bad
experiences freelancing (I was pretty bad at a number of important skills you
need to be freelance at the time) I decided to go back to school and pursue
med school. I got a few worthwhile experiences out of going back to school,
but a degree wasn't one them; I took a "break" to help a friend out with a
short term contract for programming project which turned into full time work,
and I never went back. I'm probably making pretty close to what I would have
as a GP (assuming I would have been accepted to med school, which is hardly a
foregone conclusion) with a lot more self direction.

It's not like my life would be drastically different had I stuck out the
recession, but I would have no student loans to pay off and would have
probably gotten my career on track five or six years sooner than I did.

------
spatten
I wrote this a while ago answering the exact same question:

[http://scottpatten.ca/2012/04/no-
excuses.html](http://scottpatten.ca/2012/04/no-excuses.html)

------
velox_io
While it hasn't 'paid off', yet. I'm much happier working on a startup than I
was consulting. Don't underestimate fulfilment over money.

------
unixhero
Saying no to joining an arms and weapons producer.

2 months later I got hired by a AAA firm.

