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Knowing When It’s Time to Move On (medium.com/lessons-learned)
66 points by dohertyjf on Aug 18, 2013 | hide | past | favorite | 21 comments


I hope someone writes a "I've decided to move on from 'finding myself' and get a nice job at a big prestigious software company" article, as a way to close the loop.


It's an interesting thought and I wonder how many of us who make money on the Internet and spend our days working for smaller companies will actually end up working for corporations. But, we should also note that you can keep working on side projects while working for a big corporation. This also is not the end of the world, depending on who you are. Some, that will kill their soul. For others, it's a great way to have stability and also get to work on what you love.

That said, it's not the end of the world. A big company can afford many things - incredible monetary backing to ship new things, a large support ring, and also stability. I've often railed on the choices of our parents to live in suburbia, but the older I get I realize that I could see myself living in a decent sized house with some land.

Thanks to Ryan for writing the post and getting this discussion started.


I always thought to some extent, that working at a large company (under very particular circumstances) could provide you with the resources and connections necessary to work on a side project/future startup at your leisure, without having to deal with the pressure of rapidly-draining funding or extraordinary levels of stress before you're ready.

Some big tech companies even provide support for people who want to do this (of course, under certain constraints, and to a certain extent).

Then again, if you're comfortable at a big company and working on something as a hobby or side project, the impetus to get it done and move quickly isn't there as well. Plus, a steady, large income produces a sort of complacency and tendency towards a more expensive lifestyle that would be hard to sustain once you leave again. So I guess it's a double-edged sword.

Also, if you do this, it has to be at a company where the environment and the work you do isn't toxic, but rather something you enjoy. While I was at another company doing work I really didn't like, I thought to myself that I'd compensate by working on a side project. I was only fooling myself, because when I got home I was so bored, tired, and frustrated that I had no energy to do anything technical. Different personality types might cope differently, though.


> Also, if you do this, it has to be at a company where the environment and the work you do isn't toxic, but rather something you enjoy. While I was at another company doing work I really didn't like, I thought to myself that I'd compensate by working on a side project. I was only fooling myself, because when I got home I was so bored, tired, and frustrated that I had no energy to do anything technical. Different personality types might cope differently, though.

Absolutely. I stayed too long at a defense contractor where the environment was a slow-drip toxin that eventually sapped my will to do anything outside work not related to history or wargaming. Throw in anxiety and personal issues I refused to seek help for due to the stigma of psychological treatment in a secure environment, and I was a mess. I'm in a better place now, but still recovering from the low point.


You make some good points, Austinz. I start with the thought of "What kind of life do I want to live?" and then go from there to figure out how much I need to make to make it happen. Then, any money made above that goes into savings or investing or back into a side project. The goal, for me, is to get to the place I want to be and then I will never go out on my own without the business to support it.

I think what you say about toxicity is really interesting. If it's not toxic, it depends on the person if they want to put up with it.

I'm slowly learning which one I am. I think I can put up with it, but I don't want to.


Big companies get a lot of flack from us startup geeks when in reality, they can provide the best learning and mentorship for continued growth. As with everything, it all depends on the company and your personal preference.


I hope that when it does get written, they don't make so many narcissistic allusions to "As you know from reading my prior body of work..."


Would this be a bad thing? I'm considering this.


I don't think it would be a bad thing. It would definitely bring balance and another perspective, which would be in my opinion much more helpful to someone contemplating their life direction.


I hope to write that essay in the coming weeks (although I'm looking at smaller startups).


This one, and yesterday's Google one. Honestly, I'm not sure I understand these posts...

* "I'm leaving my job because I'm underpaid." = I get it

* "I'm leaving my job because my boss is an ass." = I get it

* "I'm leaving my job for a more prestigious company." = I get it

* "I'm leaving my job because I lost passion and am not learning." = ???

If you want passion, try volunteering or get a hobby. If you want to learn, there are plenty of opportunities to do so outside of work. These are problems that can be solved without jeopardizing your ability to put food on the table.

Introspection is great for its own sake, but to me it's a little weird to mix it all up with your employment. Work is a financial transaction/relationship. You trade your labor for compensation. When did it become something we have to love and wrap up so much of our self-image into?


> When did it become something we have to love and wrap up so much of our self-image into?

When we started spending 50, 60 hours a week at work. Even at 40 hours a week, it's exhausting to try to find any real time to devote to hobbies and "extracurricular" learning outside of work. If you feel like you're stagnating, feeling like you're wasting those 40 hours of life every week, why stay, just because "work is a financial transaction" ?


This is absolutely it. When you're happy and engaged, it's easy to burn through 60 hour weeks, year after year. But when that passion starts to fade 12 hour days are an express ticket to burnout.


I'll call bull.

No matter how much passion, 60 hours a week year after year will destroy your personal/social life, and most likely your health as well.

Happy or sad, 12 hours a day is not sustainable and specially not something we should look forward to just because 'I love my job' crap


You're absolutely right that hobbies and activities outside of work can be incredibly rewarding. But to dedicate a large portion of your life to something you're not passion about, is truly sad.

I made the decision to leave pragmatically and like Ellen who shared her story leaving Google, it wasn't rushed. I'm fortunate to be in a position where I can willingly leave and I realize many others don't have that opportunity.


Every single article has a story similar to the one in this one of the guy working at 2AM trying to ship the product.

When you work 80 hours a week you're going to burn out. It doesn't matter how good of a programmer you are, it doesn't matter how dedicated you are, it doesn't matter how motivated you are. It's not sustainable.

The most talented people know how to budget out their time so they don't burn themselves out.


My stepfather had the same attitude. I stopped talking with him.


Mobile gaming start-ups - creating a more optimized Skinner Box one derivative app at a time. Run and Don't look back.


I feel his pain... unfortunately, I've got a family to feed. 15-20 years earlier, knowing what I know now, I wouldn't give it a 2nd thought.


Sorry to go OT, but does anyone have any tips for making Medium tolerable? It can't be just me. Half the time nothing shows up. When it does, it takes 10 seconds. What is so tricky about black text on a white background? I'm genuinely interested.


persistence my friend is the most important asset you can count on.




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