I feel you. I'm a non-24 so regular office hours are often problematic for me. When I was self-employed, I'd just work whenever I would feel like, be it regular hours or weekends, day or night. I'd accomplish a lot more because I would simply be in the right mood for work at that time.

I tried a 9-5 "flexible" job (remote foss work) for a year or so and was often extremely unproductive, sometimes for several weeks. It just clashes with the way I operate.

For most of the past year I've been trying to follow my github streak to maintain the idea of doing a little work every day, no matter how small (https://github.com/jleclanche/). It's been an incredibly productive year and I've never felt unproductive like I did before. I haven't felt the need for holidays because my "work days" are not tiresome. I still take holidays sometimes, as long as I can get one small piece of work done during the day, even if it only takes 15 minutes.

I kinda miss freelancing, although closed-source work makes me itch nowadays.

You might checkout Redhat and Mozilla. I've heard nothing but good things from people working remotely at both orgs, and they have FOSS projects for people to work on.

> with the proportion of the economy accounted for by solitary freelancers expected to rise

Am I the only one absolutely horrified by this?

The gig economy has never, ever interested me. I have no interest in being a freelancer. I want a nice 9-5 office job at an office park in the suburbs with strict boundaries between work time and personal time, a dependable salary, and benefits provided by my employer.

I don't even care about working on interesting things as part of my career; I'd rather work on interesting projects as a side project on my own time for pure fun. I work only because I need some way to pay my bills, because I really don't want to end up homeless. I don't have any desire to mix paying my bills with my personal life or with anything I do for fun.

But I've never really understood Millennials, despite technically being one (born in 1984; Millennials are defined as born 1982-2004). I've always identified more with previous generations. "Millennial culture" has always escaped and mystified me.

Between this comment and things like the article a few weeks ago on how suburban office parks are going away (https://news.ycombinator.com/item?id=10773865), I've lost hope for the future.

No, you're not the only one absolutely horrified by this. But it does mean that tech entrepreneurship is probably not for you, and that's completely okay. I would say it isn't for most people.

I'm still horrified by suburbs regardless, though. :-)

Why? If a suburban neighborhood is full of good people, there are a LOT of social things people do that match or are superior than what hipsters do in gentrified urban areas. Cheaper too. Want to pay 5 dollars a coffee or sit with one of your friends on their back sun room and have the same conversations with 30 cent espresso.

Want to have drinks and watch a game? How about beers and grill out with your neighbors while your kids play in the grass? Want to visit the coolest hacker space ever and scratch that DIY itch? How about help your suburban neighbor rebuild his 1971 camaro in his heated 3 car garage, or get your neighbors help you build that man-cave / craft room in the basement.

You know once the real estate parasites have convinced enough people to live in lofts with cracked 'artisan' concrete, exposed brick and stainless steel counter tops that they will then make their way back to the suburbs and try to make new dollars there a generation later. Millenials have been sold on an image just like the working man and woman were sold on the suburbs in the '50's to '80s.

I've been working from home for about 8 years now as well, as a director of an agency, as a freelance consultant, and as a startup co-founder. Until I put into place some structure around my work hours, I was less productive and enjoyed my life less. Your final sentence seems to ask for more "enlightened" views on an unstructured work environment, but you seem to be displeased with yours; am I reading that correctly?

I'm not necessarily displeased with the very fact per se, though in my particular case it was an extremely - and shortsightedly - solipsistic choice for a (then) 22 year-old extrovert to make.

I agree that structure and routine are essential. However, many people, including myself, ended up in self-employment in part because they can't do 9-to-5 well or consistently for years on end.

> I would think I'm not the only one who doesn't even remember what weekends or holidays are anymore.

I've been also self-employed for 7 years, started as startup co-founder, rented office in the best tech hub in my city, etc. Then we started to cut costs, ditched the office and started remoting and freelancing for several clients. It's been 4 years working from home now and sometimes I hate it, but other times I like it.

I think the authors of that article are spot on. Having the schedule you dreamed about, means nothing if you don't have anyone to share the good moments...

This year probably I'll start travelling. One colleague who is a top-notch SEO, is doing the nomad thing and he seems really happy travelling and living 6-8 months in different places of the world, sharing co-working spaces, meeting new people, etc...

The problem with always-travelling is health insurances. I have found that most international insurances (for example Allianz) insure you "worldwide, with a country of residence" meaning that travels are limited to 3 months. Which seems incredibly inadapted to people from generation Y.

It depends on where you are. In a lot of parts of the world, you're better off paying out of pocket. I would say not just in the developing world -- even out-of-pocket fees for foreigners not covered by social medicine in the EU didn't strike me as being egregious or unaffordable. Then again, perhaps I was comparing them to the insanity in the US.

World Nomads has worked for me. You just buy a new policy when you need to extend the trip.

If you buy one for 6 months it comes out to $80 / month. You must be farther than 100 miles from your home residence at the time of your medical incident.

I believe the catch is, if something happens and you need coverage beyond the end of your current policy, then renewing it doesn't earn you continued coverage for that incident. That would be what they call a pre-existing condition.

So you'll notice when you sign up that the longer you extend your policy, the more it costs per month. E.g. 3 months might be $200 and 6 months $600

After a lot of pressure from parents ("So what time do you get off work tonight?") I came up with a semi-decent metaphor: Us entrepreneur people are on a hunter-gatherer schedule. I can't predict in the morning whether or not I'll be hunted by a sabretooth in the evening. Or whether or not I'll spot some tasty roots and have a lazy meal with friends for three hours during the early afternoon.

Hunter-gatherer. Excellent analogy. I'll reuse it. With non-millenials.

I suspect that have more to do with your unwillingness to set boundaries and limits on both relationships and time. It's as simple as establishing that if you want to be friends with people you also work with that when you are not in a work environment or mode that you not talk about work. Work-life is only fluid if you allow it to become so. Those are all very much choices and lack of choices you are making. There is nothing different about Millennials other than that they have grown up in an environment and society that has not be able to set boundaries in many different ways in a long time.

Same in Academia