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Ask HN: What's the biggest risk you took in your career that paid off?
96 points by ruffrey on May 28, 2016 | hide | past | web | favorite | 81 comments

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.

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

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.

If you don't mind me asking, what are you doing now? Are you back to work or are you still traveling?

Make a blog post, i'm interested... Similar story by https://levels.io/ here https://levels.io/reset-your-life/ ( i actually loved the post)

PS. He's a fellow HN'er also :)

Very similar story yes, nearly identical actually, I also had issues with anxiety and depression before I left, it was one of the reasons.

what are you doing now ? where did you go ? what was your work ? could you please share your story

I am still traveling (usually switch country every 1-3 months) and freelancing/RemoteWork earning 3 times what I made before and enjoying being my own boss :) And no, I am not a coder/programmer, but IT field, which makes this remote work thing obviously much more easy.

What does 'IT' in this case mean? Remote configuring servers and administering user accounts? I have very little experience of Big Orgs so I have no idea if that's the scope or something more.

Cloud Engineer fancy modern title

I'd like to talk to you more about this. Care to exchange email?

In about two months I'll quit my job, I'll start a business with a friend, we'll see how it goes. I'm really interested on how it went for you.

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

Here's to switching jobs to fight pay compression.


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?

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-...

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.

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.

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.

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

(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."

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.

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.

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.

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

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.

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.

I started freelancing and definitely think more about a self sustainable paid service, and have more time to work on it too. I'm trying to improve myself as a consultant but think I'd prefer to concentrate on a product. But a bit short on the ideas. Would love to hear some examples you'd think was not a stupid idea to work on.

Tap into a smaller sector that you can develop software for. Something that will automate things for them or software that will make them money or save them money.

I would suggest starting with the clients you are freelancing for. My first SaaS came about from a freelance gig.

How are you getting and validating your ideas? Are you just trying to scratch your own itch?

I pay really close attention to trends and try to tap into things that aren't overly competitive.

I also run ads to an MVP before investing too much time into it. Don't get me wrong, not everything I have launched made money. I have lost my fair share too ;). I tend to shut a service down fairly quickly though if it's losing money.

Most of the advice I read about always says to solve your own problems, so it's really interesting to see somebody with a different approach.

Are you just paying attention to trends in your area of expertise or are you following trends in multiple areas, how do you keep up with them.

Maybe you can tell more about your previous Saas products, because I'm really interested in your approach.


I wish I could make money solving my own problems ;)

I look outside of my own areas of interest or expertise. I follow a lot of industries/small businesses outside of tech. I also pay attention to what my son and his friends are into and have launched a couple of content sites based on that.

For the SaaS products: 2 were niche Real Estate products one of which is still running and profitable, 1 was a Facebook apps when Facebook pages were hot, 1 was a Twitter app during the early days of Twitter, 1 was catered towards solar companies. All at their height made over $10k monthly rev, some more than others. I launched others though that were bad bets that I lost money on. I hate losing money though so if I don't see something turning a profit within a few months, I move on.

I have also launched niche content sites around popular games, tv shows, etc., one of which I grew to $20k monthly rev at its height and grew the opt in list on another to 300k+. These niche content sites don't last very long though because once that game, tv show, hot topic, etc. is no longer hot, you stop making money. They are fun to run while they last.

Lastly, I would probably consider myself a better marketer than programmer. Programming for me is a means to build out a product. I don't love it but I don't hate it either. I view it as a tool to accomplish what I need to do. I am pretty good however at advertising and knowing how to reach a target audience. I also try and track as much as possible so I can make educated decisions based on data. I am not much of a risk taker. I heavily rely on data to make decisions.

Resonates a lot with me, would you mind sharing any resources you have found useful to develop these practical skills in marketing? i.e. maybe Moz for SEO

I generally do not start out with SEO or worry much about organic rankings. Depending on the target, I start with Google & Bing PPC, Facebook Ads, Reddit Ads, LinkedIn Ads, Pinterest Ads, Twitter Ads.

This does take some investment upfront but allows me to gather data and test conversions quickly. Based on the data/conversions/feedback from these sources, I fine tune and tweak.

After a few weeks, you will have a ton of keyword and search data from your PPC ads and Google Webmaster tools. If I see some low hanging fruit search terms from that data, I will then invest in trying to get them ranked organically.

Make sure and setup a Google & Bing webmaster account and analytics. I have also developed my own software that I use on all my sites that captures a ton of other data that I want to see. Google Analytics isn't always accurate and doesn't always give me exactly what I want to see to make educated decisions.

Thanks for this thorough response!

Stuff that brings money is mostly not "solving your own problems".

It's one of the lies that became "truth" in some parts of the Internet.

Software as a service service.

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.

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.

*Software-as-a-Service service.

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.

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!

Genuine question...

How does one get fired as an admissions counselor? Was it just a lay off, or was it something else?

Regardless, congrats on the programming job.

I'm sorry, but how is applying for a job you're unqualified for a big risk?

I assume it didn't take more from you than an hour to apply at the most and you got lucky by landing it.

If that's the case, people take dozens of bigger risks every year.

Also genuine question...

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

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...

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.

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.

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

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.

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

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)

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...

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".

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 :)

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.

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.

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.

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.

Really interesting project. Mind if I contact you?

Please feel free to contact me. Mention this post.

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.

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.

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

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

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...

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.

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.

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.

Interesting, which company it is?

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.

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 ?

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.

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.

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

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

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.

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


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.

Saying no to joining an arms and weapons producer.

2 months later I got hired by a AAA firm.

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