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Ben Halpern
Ben Halpern

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What's the best career decision you've ever made?

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Kirk Munro

Deciding that my job would not dictate what I worked on, but instead that what I wanted to work on would dictate my job. Years ago a particular technology really grabbed my attention, so I went all in on that technology outside of my work -- mastering the technology, answering questions about it online, delivering presentations about it, etc.. It took a lot of hard work and hours outside of my regular job, but that single decision led to more career advancement and opportunities than I have ever received by simply following along with whatever my current work wants me to do.

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Charles Reace

Interviewing for a job 6 years ago in northern NJ near NYC, an area I was sure I wouldn't want to move to. I've now been working there for 6 years (and living there for over 5 years -- a very long commute for the first 9 months!) and am glad I didn't let my geographical biases get in the way.

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Kim Arnett 

Exactly. It seems it's a market in our favor, but navigating that is a problem 😓

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Kelly Vaughn
  1. Specialize. I was stretching myself thin, trying to do and learn everything. I found an interest in building specifically for Shopify and jumped on the opportunity to become a Shopify Expert, and the rest is history. Specializing in general allowed me to really hone in on the skills required for the tasks at hand and let somebody else with a stronger interest in other areas excel at those.

  2. Quit my corporate job to do my own thing. I was working for the government as a developer, and there were so.many.hoops to jump through. It took an incredibly long time to get anything done, to explain why I needed specific permissions on my computer to do my job. (For example, I had to complete a 9-page document as to why I needed something other than Notepad for coding.) I waited until I had a solid line of work coming in (in other words, I found myself a retainer client) and then put in my two weeks. It's been a year and a half since I started working 100% for myself and I couldn't be happier with my decision - it came with a significant pay increase, complete freedom over my schedule and selection of projects, and most importantly, really proving to myself that full-time freelancing is a 100% attainable goal.

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Miquel Beltran 👨‍💻

I also think specialization is a key to success! It is really easy in tech to jump from framework to framework, language to another language, but we fail to realize that companies don't need jacks of all trades, they need the best doing their jobs. Since I focused on becoming a great Android developer I never had any problems finding my next job.

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Austin Wehrwein

+1 for Specializing. Not only because expertise usually can lead to growth in your career, but also because specializing hopefully means you are more interested in that area.

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Virgil

Let me provide a counter-argument to 1, because so many people love it: if you specialize, you narrow down your options. So, you're the world's most renowned expert in MUMPS? Congratulations, but almost everybody stopped using it and there are a total of 10 companies you can work for in the entire country, only one in your city. Hope it doesn't go under, or you don't get into a conflict with you boss.
Best Symbian developer in the country? Sorry, Nokia almost went bankrupt, and switched to Windows anyway. What, you thought that'd never happen?

The narrower your specialization field, the more at risk you are that the entire field will be disrupted, and the less jobs are available to you. Better hope that you picked your specialization well! And remember, we all suck at predicting the future. Yes, even you.

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Jeremy Davis

Interesting point - but I'd argue that being a specialist shouldn't mean tying yourself to one technology forever.

I've been working in web content management for sixteen years now, and am on my fourth major CMS. I (and the company I work for) have "specialised" in all of them for a while, but we've been flexible enough to jump ship to different technology when we see one system getting overtaken or when our market's needs change.

I'd also make an argument that demonstrating that "ability to adapt and learn new stuff" skill is a really good thing for your CV alongside "really knowledgeable about something". IT changes fast, and good employers should value people who can understand and adapt their skills to those changes.

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Mark Cassidy

Specialise. Absolutely agree. Narrowing focus down and aiming to be the best I can be in a specialised field of knowledge. Not being ignorant to "everything else", keep an eye on things surely. Like switching to GIT when the time came, keeping up to speed with new major development trends. But always keeping an eye on the ball though.

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Daisy Chubb

This was so great to hear. I'm in a similar boat - currently working 2 government terms and really wanted to specialize in mobile dev & building for Shopify. In my own time I'm torn between so many languages I "should" learn - when really I know what I am leaning towards and enjoying, so I should focus on that for now.

Anyways, I'm late to the game but early in my experience, so I know I have a lot more to learn! Just good to know that I can sit down and focus on something, even if it's not related to my job at the moment. Spoiler: really not enjoying my co-op placement.

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❄ Sean P. Floyd ❄
  1. Disagree about specializing. Sure, you need to dive deep in some areas, but a generalist will always get jobs, no matter where the industry is moving. And most of the big companies have realized that it's more effective to hire generalists.

  2. Freelancing is a great way to get around and learn a lot. I did it for 10 years. But eventually, the experience I gathered that way helped me land good corporate jobs, and I'm now very happy at your favorite Seattle-based eCommerce giant, getting a decent salary and with a nice career laid out in front of me. Corporate doesn't have to suck. If it does, you're in the wrong company (or just department). That said, perhaps I'll freelance again in 5 or 10 years. Who knows.

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edA‑qa mort‑ora‑y

Interesting, I've done pretty much the opposite of specialization to find my success. Isn't specialization in too much danger of becoming obsolete?

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Claire Pollard

1) Apply for that job. I almost didn't apply for my current job because I thought I wasn't qualified. I'd made an assumption without even trying. My fiancee persuaded me to in the end. Turns out I've found a great team and manager who has helped me grow into the job I have.
2) Don't feel limited to the job title you're given. If you get employed as a Software Dev and want to help with something else in the company, pitch it to your team/manager. I do not regret asking to help the marketing team with their work, and it has given me new ideas about how to approach both my development and how to help promote the work my company does from a technical standpoint.

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A.D.

"If IE is brave enough to ask to be your default browser, go apply for that job"

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Kyle Carter

Whole heartily agree with the second point! That's how I got to my current position in my company, found a niche I like, helped where I could, and then my manager asked me if I wanted to do that particular work more. Has pushed me to grow a lot faster than I would have otherwise.

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Chiara DeLucia

Mine may be trivial, but right now it has been the absolute best decision I've made: I decided to become a developer! And then I stuck with it, and stuck with it, and stuck with it...always when I thought I wasn't smart enough or I that I couldn't go on.

I'm still really new to web development -- I haven't even gotten my first job as a developer -- but after all the hard work I've put in to this transition I'm starting to actually see myself as a developer. And every time I think of myself like that, I know that making this transition has been the best career decision I've ever made.

I can't wait for all the future decisions surrounding this career!

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George Offley

That's not trivial. I'm in the same boat. Looking for a developer gig and working on my personal projects. Good luck to you!

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Kim Arnett 

1) to go into mobile development
2) to not stop looking for my career until I found a supportive manager and team. I found myself in a few poisonous positions that were taking a mental toll on me. I'm on my 3rd company in 4 years, but I'm very happy now. :)

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Jessica Bell

Quitting a terrible job after only 6 months. It just WASN'T working, I was unhappy, bored, angry, and I didn't really see it changing. I got A LOT of shit from people saying I was just a millennial jumping jobs whenever something hard came along, but no, it was really not a good fit and it was best for both parties. Now I am at a place that fits my career goals, my interests, and my lifestyle.

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Ben Halpern

Anybody giving you shit for leaving a job that was clearly not working out for anyone is an idiot. Congrats on finding a place you're happy with!

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Jessica Bell

Hard not to be happy at Washington Post :P

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Tashas[E]v

Actually really joining the tech community(ies) for areas I am interested in. And by really joining I meant I started by attending regularly and often, then offering to help, then organizing and running my own events. There's no better way to become immersed in the thing you are trying to learn, meeting people who are really smart, networking, and staying current on trends. Also, you make great friends and jobs start looking for you, as opposed to the normal way of things :)

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Miquel Beltran 👨‍💻

+1 being an active part of the local community it totally changed the way I see development. It took me 15 years (if you include also university) to realize how fun and rewarding tech events are.

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Ben Halpern

Personally, I'll say: Sticking in the entrepreneurial side of things. I almost jumped to a bigger company a couple years ago. Looking back on it, I am really glad I stuck to what we are doing.

The money, had I left, would have been better than anything I am currently earning, but I have learned that I really have to be navigating my own path. I am confident, with hindsight, that I would have been frustrated and ultimately burned out at a large organization like that. It's just not my thing. If I ever join a large organization, I want it to be for particular project where I'll definitely get to be creative and have agency. Being a cog in the wheel is not my thing.

I'd guess the opposite is true for many others. Stability and career ladders have never been my thing. I'm 28, though, and I might have a different perspective in a few years.

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Daisy Chubb

Thanks for your POV, Ben. I am also 28 and reeling against the corporate career ladder that so many people are preaching to me. I don't know if it's wrong or right, but I know I have worked my whole life up until now just to scrape by and pay the bills. If I can pay the bills AND enjoy the hustle - that is value on life investment (for me)!

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Zack Hall⚡

I find myself to be more entrepreneurial – I've started side projects and companies in high school, college, and now doing freelancing on the side. None of them home runs or ventures that generated fuck-you money, but non-trivial. But my day job and my primary income comes from working at a larger company.

I'm feeling that burnout and the frustration that I can't navigate my own path or trust my own judgement.

But despite having earned several thousand last year, I don't have the confidence to do it full-time yet. That it can provide a stable income for me to live on and save up for large goals, like a house, marriage, etc. How did you get started on your entrepreneurial tech journey?

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Jeff Lindsay

I was originally going to say my best decision was to not specialize. By always learning by always doing new things, my opportunities and capabilities continue to increase. At some point, you see enough that everything starts to become similar, making it even easier. Then at some point, you look back and realize, "Huh, I feel like I could do anything I wanted."

However, more importantly, I think my best decision was and is to always follow my interests. For some this might lead to specializing, for others, generalizing. Maybe for me it was a little of both. However, if I didn't do this, I would not be motivated to learn and try new things. I would not be driven to finding the edge of some area, putting me in the right time and place to be there for major innovations, in some cases making them myself.

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Liza Shulyayeva
  • Applying for positions even if I didn't tick all the requirement bullet points for them. I didn't really think about this one much at the time and thought everyone did this, until after a few years in my industry I kept hearing this sentiment of people being afraid to apply for jobs just because they don't 100% fit all the criteria. I figure if you don't blatantly lie and claim to know something you don't, the company will do its job of weeding out an applicant if they're underqualified to do the work.

  • Learn in your own time. I've always had my own projects going ever since we got our first computer after moving from Ukraine to the US. The ability to learn quickly on my own helped me greatly as someone without a CS degree to fall back on.

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Charles Reace

All those requirements are their ideal wish list; but any smart employer worth working for should be more interested in you and what you can bring to the team, as opposed to whether or not you can successfully check off every one of those items.

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Ben Halpern

Yes!

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Jhon Paredes

Showing my side project to the CTO.

Originally I was in Marketing as a Web Developer, but was fiddling around with React and Elector during my spare time. I managed to patch together a simplified version of one of our product features using our API. It was a fun side project while I learned new tech. I showed it to our CTO and he offered to switch me to Engineering. Great career move, great support from my company, and it wouldn't have happened if I didn't do show him anything.

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Kathryn Grayson Nanz

Making the career switch from design to development. When I was first out of college, every other designer I talked to warned me not to start learning code because once an employer found out I could code, I would never be assigned design work again. Nobody ever encouraged me to try it out or see how I liked it, and it was years before I got there on my own and discovered it was actually a much better fit for me than design ever was.

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Chrissy Wainwright

Switching Jobs.

At the time, I was working from home and happy with my job. But my husband knew I had the potential to earn more money, and encouraged me to find a new job. I have been with my current company for 9 years now, have grown so much as a developer (moved from front-end to back-end), have gotten to do some traveling, and have been involved in a world-wide open source community.