Ask HN: Those who have taken extended time off, any advice?

83 points by deilline ↗ HN
I've been looking to take some longer time off in between my current and next role, on the order of 6 months to a year.

Any advice from those who have done it? Did you get bored? Was it worth it? Was it more expensive? Things you found helpful when preparing?

93 comments

[ 1.7 ms ] story [ 167 ms ] thread
I'm also planning on doing this. I fervently want to live in another country for at least a few months.

I could probably stop working for about 6 months if I pick a cheap country.

In my experience you need to live somewhere for a bit longer to really understand and appreciate it. Takes me about a year to get of the shock and start to settle in. If you can, make it 3 years for a proper taste.
If I can figure out a way to make a decent income I'll do at a year or so.
Bocas Del Toro, Panama is fun, safe (crime but it's only property/opportunity), and cheap island to setup at. Lots of expats, rent starts at $250 , I might even see you there
Any experience working remote there. I imagine if you can earn a six-figure salary as a digital nomad but keep your monthly expenses to less than $1,500 you'd be able to retire within a decade.

I've seen the rat race to the top, but aside from taking some shallow pride in making a lot of money I don't really see the point.

Yes I did work remote there, the maximum internet speed you'll get is 5mpbs/1mps , and it's flaky.

It goes down once a day , you'll want to be setup to work through the down times ( offline documentation, be able to fake connections etc ).

You wont be able to Zoom, but you can get a google number and use a local telephone if that works.

But yeah I'm with you on working less and enjoying life more, that you can definitely do there. There is actually a lot of similarly minded people ( expat Americans and Canadians ), doing the same thing. I love it there, as soon as the Pandemic flushes out I'm going back, though I'm trying to get out of software work.

What if I pick a fast internet county like South Korea ?

I'd also know what's the best thing to do tax wise, I'm working on getting a nomad visa, does Corp to Corp work , should I create an LLC ?

There are many countries in Asia that fit the "decent internet" requirement if you are able to put up with the timezone difference: SKorea, Japan, Taiwan, Thailand, Malaysia (and I'm sure many more). Quite a few of them are also pretty cheap (SKorea would be on the expensive end of the spectrum)

I've been living in Taiwan for ~5 years now and have 1GB/down 40MB/up internet to my apartment that costs around $40USD/month. Total living expenses for a family of 3 are around $2kUSD a month.

Great, how do you file taxes though . That's my main concern, I assume most American employers will be weirded out if you put down a foreign address.

Do you contract Corp To Corp ?

The absolute dream would be to live off 2 or 3k a month , but still pull down 10k or so from a remote job. I want to retire early.

>The absolute dream would be to live off 2 or 3k a month , but still pull down 10k or so from a remote job. I want to retire early.

I've done that for a few years with an even bigger difference between income and expenses :) I'm set to quit working for money this year (see post history for more on that).

>Do you contract Corp To Corp?

I have a foreign corporation and invoice my US clients through that.

It sounds like you're a US citizen so a foreign corporation might not make sense in your case. The IRS is after your worldwide income and a foreign corporation isn't necessarily going to help avoid US taxation given that you'll have to disclose the ultimate beneficiary (you) to your US clients with the W8-BEN-E form.

A US LLC might be a better fit for you. Also look into the Foreign Earned Income Exclusion[0], which allows you to earn ~$100k free from US federal taxes if you spend the majority of the year outside of the US. You'll of course have to pay taxes wherever you reside as well, but it's a bit of a grey area if you don't spend >= 6mo anywhere. In that case, you could likely get away with only paying US federal taxes on the amount above the FEIE limit and pocketing the rest. But do consult professionals, don't trust me!

Good luck!

[0]: https://www.irs.gov/individuals/international-taxpayers/fore...

I'm in the process of establishing a US based LLC.

I figure clients would pay the LLC and then the LLC pays me.

> I've done that for a few years with an even bigger difference between income and expenses :) I'm set to quit working for money this year (see post history for more on that).

Awesome ! I don't have to really work for the rest of the year , but I want to save as much as I can so I can take a good long vacation. If working from overseas doesn't work out I could still live without work for a solid year or so.

Any other tips to share ?

>Any other tips to share ?

The book Vagabonding[0] by Rolf Potts is an excellent read for this sort of thing. Happy travels!

[0]: https://vagabonding.net

Thanks ! Just brought the book .
Maybe so, but that’s letting perfect get in the way of the good. A week in a new place can be life-changing. 3 months can feel like a year. Don’t need to set “really understand” a place as a requirement if your goal is just to enjoy your life and make it richer.
Try to take 3 months off maximum.

With my paid job I sometimes got overwhelmed and sometimes felt a lack of purpose. At those times I found solace in side projects and would even try to sneak in working on them at my paid job. A few of those projects were successful enough to quit my paid job for a few years.

Since then I've turned to quitting my job first and then trying to start a side project. It's not the same and I haven't succeeded. When you have infinite time you stop to value it. You can always do it tomorrow or next month and the procrastination or perfectionism creep in.

My sister says that if you really want something done, you should give it to the busiest person you know. It seems contradictory, but the busy person values their time and they will get your task done as fast and as efficiently as possible.

> Try to take 3 months off maximum.

This is too strong of a general statement. There are plenty of situations which may require longer than 3 months.

Personally speaking, I’m currently on month 7, and it will probably take a few more months before I’m ready to commit to any sort of formal work arrangement.

I hope your sister is never my manager
My rule is to try and take 3 months off MINIMUM. I find that it's only after three months that the 9-5 work habits fade away, and I become truly free to explore this unstructured time.
I have done it twice. The first time I spent about 3 months riding my bicycle around the US. Then spent a few months looking for a job. It was not a good market. The second time I spent 7 months in New Zealand and Australia. Half the time biking. Took only 2 months to find the job I had before I left. I was trying to get one in a different city.

Make sure you have your health insurance lined up, in case you have a hernia in Australia and get it operated on then... never know.

Have a better 'back to work plan' then what I had.

Have goals and schedules. Have some loose timelines. RE examine your goals, preferably with a trusted friend, to keep you intellectually honest. Do this on a strongly fixed schedule. Be it once a week, once a month, every other month. I would not recommend less often then every 3 months.

My first trip was a burnout fix. My second was because I could.

I would say make a detailed budget, but that depends on your plans and resources. I did not, but I usually have a good sense of what my finances are.

Do not go into debt for this.

There are some important points here. I would add these. 1) have a plan. what are you going to do? This is important as you may find yourself 'done' with whatever it was you were going to do. What is plan B?

2) have a budget. what can you spend per day? What is your current burn rate vs your new one vs liquid assets on hand? Are you OK with the difference?

3) when you start looking again what are your expectations? You now have put a hole in your resume. Remember companies like the idea of you can 'hit the ground running' so have a story for this. From their side of the desk you look like someone who can not get hired. They will use it as a filter. They have 200 resumes to look at and 199 have to go. Any dumb thing they can to kick you off that pile is one they will do.

4) do you have other obligations? For example car payments? Spouse? Parents who need help? etc? These may consume your time/money faster than you think or plan. As they will all say the same thing 'you are not working why dont you ....' Set boundaries.

I personally would not do it again. It was enjoyable enough. But the money anxiety I got was bad. Even not really having any debts or anything to worry about. It was just too much for me personally. I was not bored as I have plenty of projects I like to piddle with.

I did it after my first job. It was a break of about a year and I spent the first 5 months just backpacking around and climbing mountains.

I enjoyed being off grid with even my smartphone mostly off and being used just as a camera. It just felt very relaxing and I was in the best of my mental state then. I got the chance to meet a lot of new people from different backgrounds and just have different experiences in different places.

I didn't regret it a bit but after a while I kind of started missing my computer as well, because I do really enjoy building stuff as well. So after five months, I started working on some ideas I had, sadly they didn't pan out and I joined a new job in some time after doing 2-3 weeks of interview preparation. In total, it was a break of about a year.

Since I mostly used to stay in hostels, tents and was mostly on foot or cycle, it wasn't expensive. But if you are used to a paycheck, it seems weird when you have to take money out of your investments. So, you start thinking about your long term savings after a while.

I am not sure what you meant by preparing, I didn't have an exact plan or budget. I just had some mental estimate of the rough expenditure and how much of my savings I was willing to burn.

It totally depends on you but if I do it again; I would plan it a bit upfront(at least the major checkpoints) and would keep my break between 3-6 months.

I retired at 32 and its been about 5 years. Its pretty fucking cool. One thing is everyone else looks super retarded. I missed out on all this Me-Too and covid and social justice insanity, so thats cool. But man, it really makes everyone look really insane if you are not a part of it.

I don't think I could go back at this point. Also, I tend to give less of a shit about social pressures if you are not always worried your boss or whoever might see something to say or type.

Overall I feel bad for people that have to live the life of working.

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The most surprising thing I discovered was that it took me 3 months to lose a jittery “I.SHOULD.DO.SOMETHING.NOW” feeling. Only after 3 months did I feel truly relaxed to pursue whatever interest-driven nerding project and at the same time letting go of a sense of achievement or progress. 2021 was supposed to be a “me” year until an interesting project came along. I said yes. Taking time off is hard.
Taking time off is a skill! I think the 3mo threshold is common. It takes a long time to start to "let go" as you say. Pre-tech career I worked seasonally and for years had 4-5 months off a year. It let me build up a different, more positive understanding of myself, decoupled from the anxieties and pressures of work.
My wife and I retired in 1998 and moved to the mountains (Sedona AZ). Since then I have worked onsite at Google and Capital One, otherwise did occasional consulting gigs remotely and worked briefly for two companies remotely. I feel like I have had large extended time off periods, except I am always writing a book (BTW, shameless plug: I just published my "Practical Artificial Intelligence Programming with Clojure" book today - grab a free copy from my web site https://markwatson.com)

I haven't been bored for too long since boredom is a trigger for getting some work. We are in a relatively inexpensive area to live which helps financially.

I would rather leave some money on the table and have more free time.

It wasn't boring. I made my 4th and 5th kids, grew a big garden, maintained procps, added features to Tux Paint, and messed with reusing CVS's silly single-use video camera.

Maybe it was worth it. It definitely was expensive, despite living cheaply. I didn't prepare at all, aside from my normal habit of living below my means.

Took 3 months off. Amazing stay-cation, I already have a laundry list of things that I wanted to do, so I did not have too much time to get board. Great for mental health, as I was getting close to burnout after a number of person live issues.

Now I am just going to be working part time, as I loved the balance that doing non-computer related work gave me. With proper budgeting, and a decent industry you will be surprised how little work one needs to do to live a happy and humble life.

I've done it several times.

Yes, totally worth it.

Yes, totally got bored. That's a good thing, it's the polar opposite of creativity and we need to live there some of the time or we lose track of the value of creativity and come to think of it as the day-to-day grind instead of the fun adventure it can be.

It was not more expensive. With all that time I could make my own food and minimize the monetary friction of convenience to save time. Everything went much slower and more thoughtful.

Helpful prep? Have ideas for a project, something to accomplish on a day to day habit kind of process and another long term. Not stressful projects, nor necessarily productive projects. Maybe learning? Maybe more physicality? Me, I did more yoga and took classes at a local maker space. Worst thing you can do is leave all your time open and free. You won't value it. Well, 2nd worst thing is to expect you can do too much and kick yourself for not living up to your potential.

Relax.

Took 9 months off after I quit my first job. I was working on a startup, pitched it around town, and it failed pretty miserably. Even so, it was probably the happiest time of my life.

The immense focus, waking up and working on my thing. No pointless meetings, standups, or sucking up to people. I feel that I got a taste of what people that are financially independent always rave about. I started frequenting a local coffee shop, got to meet a ton of people from all walks of life.

Totally worth it.

I took a three month leave of absence at the end of a six year run of 7x24 days in the dot com era, totally burned out. I extended it another three months as I entered the initial last month as I didn't feel "ready" to return.

I think the experience completely broke my willingness to return to a "normal" tech role again and I've bounced between short bursts of employment and long bursts of not working or semi–employment as a consultant.

I think it also saved my life.

Mistakes I made:

  I didn't have a plan to structure my time off.
  I didn't have any goals to accomplish in my time off.
  I didn't arrange ahead of time for a role to return to.
What I did do: learned basic Mandarin, established a relationship that has lasted 20+ years, read many non CS / non-technical books, focused on getting healthier and fitter.

Specific advice: structure your time off, set goals, try to accomplish them but don't punish yourself if you fail. Arrange ahead of time for a role to return to, even if it's time limited or isn't what you "really want to do".

I wrote longer about this previously but can't find it in my first few pages of comments.

> What I did do: learned basic Mandarin, established a relationship that has lasted 20+ years, read many non CS / non-technical books, focused on getting healthier and fitter.

Would imposing a structure and setting goals for your time off have helped or interfered with these (admittedly admirable) results?

I think it would have helped with re–entering a normal work environment, I don't think it would have interfered with the results.

Honestly (and this is ~20+ years in the past now) getting some sort of therapy after spending five years in the dot com craziness would helped as well. Sometimes it's difficult to realize you’re in a toxic environment until you’re well removed from that environment.

Copy pasting my comment from a previous thread:

In 2016, I quit my job working at a small software firm in Chicago. I didn't think I would do it, I was afraid I would keep putting it off, so one day in the middle of the workday I just abruptly opened AirBnB and booked an apartment for two months in Paris, just like that, non-refundable, plus a flight, also non-refundable. It was 7 months in advance, to give myself plenty of time, but also to put a definitive date on the matter. I had never been outside the US at the time. I left at the end of July and spent all of August, September, and October in Europe, living off savings and just enjoying the sights, alone.

I have a mixture of extremely good and sad memories. I do not regret it in any way and am extremely glad I did it.

My place in Paris was lovely, right by Les Gobelins in the heart of the city. The weather was beautiful and I would just spend days walking the streets, visiting every museum and cathedral and café and restaurant. The best thing is that under such circumstances you aren't pressed to fit everything into a few days-- you have the freedom to do something every day or every few days, whatever pace you feel like. So you never end up feeling hassled or pressured.

I would pass whole afternoons sitting in the window of the bookshop across from Notre-Dame Cathedral, listening to the churchbells and reading books. I would spend many evenings walking the river. If I felt like it, I would take a train out of the city to a random village in the countryside and visit castle ruins. I did this many times. It's amazing what you can find sitting around in Europe, hundreds or thousands of years old decaying in a field. So much history there.

I rented a car and drove to Normandy, and to the south, and saw many more things. Eventually I flew to Italy, and then to Croatia. Croatia was the best part of the whole trip-- it's an unbelievably gorgeous country. It's not so well known as Italy and Greece and France, but it's as good or better.

A lot of this time was spent playing video games on my laptop in my airbnb room, being a little sad that I was on my own. That's the other side of it. Some friends flew out and spent time with me there, totalling two weeks, but the other eight weeks was just me in a land where I could only speak the language well enough to get by, but not well enough to get to know anyone meaningfully. It was lonely. And all the while I knew I had to go back and figure out what to do next.

I think it depends. You have to know yourself. Money can take away some causes of unhappiness, but it can't give happiness, only freedom, which isn't the same thing. Purpose is happiness, someone said to me recently, and I agree with them. Traveling on my own, I had freedom, but no purpose beyond seeing beautiful and ancient things that I'd never seen before. It was lovely, and I'll do it again soon. But I wasn't as happy as the times when I knew I was where I was meant to be, with people who needed me there and wanted me there.

I don't have a tidy conclusion. It's just food for thought I guess. My personal answer to OP's question. For what it's worth, the whole 3 months cost me <$6000. Staying in one airbnb for an extended block of time and buying groceries instead of eating out 3x a day makes a big difference, plus the trains are cheap in Europe.

At may last gig, I was super burnt out, it got to the point where I'd go into the office, but spend my time mostly dicking about. Maybe doing an hour of work in a day. After six months of that (and having no one actually notice, that was probably the worst part) I decided I couldn't take it and quit without a plan.

The first few weeks I did absolutely nothing but workout, read books, play video games, or just lay out in a hammock. But as soon as the stress started wearing off, I started feeling the itch to make things again. Because I didn't have anywhere to share what I was making, I ended up organizing a local meetup for Rust, which ended up getting me my current job doing shit that I love. Though when I accepted the offer I made my start date a few weeks out just to round my time off up to three months off. That was the happiest time of my life. I fully intend to take at least that much time off if I ever leave this job too. (Though I might even see if I can swing a three month long vacation/sabbatical without leaving once my project is released.)

My only advice: do it.

I did basically the same thing as you.

> The first few weeks I did absolutely nothing but workout, read books, play video games, or just lay out in a hammock.

But I did this for 3 years, never tired of it, and only got a job when I had 6 months of expenses left in easily accessible cash (could’ve held out longer if I had sold off stocks but didn’t want to do that).

Its interesting to see 3 months coming up a lot. I think it sounds like a lot of time but growing up I got 3 months off from school every year for summer break. We really torture our selves to work.
- "Try to take 3 months off maximum"

- "structure your time off"

- "Have goals and schedules"

- "Arrange ahead of time for a role to return to"

You are getting a very American perspective in this thread so far (possibly due to the time of day). I will counterbalance it.

Advice: You're overthinking it already. If you feel like a long break in between roles, take one. Book a one way ticket to a place you've always wanted to visit, and figure out your next steps once you get there. Many/most places in the world (including within the US) are very cheap to live if you don't need to live close to work.

Maybe you end up getting bored and returning to work in a few months, maybe you run out of money, maybe you love it and travel for a year or more, working hospitality jobs to get by. All of these are great outcomes, and you will learn something about yourself that would have been impossible to discover while heads down working full time employment.

COVID is a bit of hassle right now, but places are already opening up, and come summer you should have many more options.

If he's American he should take into account that we have no safety net, so he has to be careful how he does this.
Ah yes the standard vacationed too long safety net.

There's unemployment and welfare for those who need it, not SWEs that don't want to work.

Don't work safety nets into your plans, they are for people in need, you are taking away finite resources from people who need them if you use social programs when you are able to work.

It depends what you mean by safety net. Certainly most folks on HN have the safety net of being able to return to work fairly easily whenever they might choose to, including finding remote work.

If you mean "individual healthcare in the US is expensive", I absolutely agree. Assuming you are otherwise healthy, catastrophic health insurance might be worth looking into (I have never tried it myself). Another option would be to travel internationally, because travel insurance (or even the cost of private care) in most other countries is going to be much cheaper than a domestic health plan.

On the other hand he can actually take off and go wherever he wants thanks to his American passport.
Ah yes, the world's 45th most powerful passport.

[0]: https://www.passportindex.org/byRank.php

This is a pretty dishonest way to present this IMO.

I've been traveling for the last 10 years and my American Passport never got in my way, and in exceptionally few cases would anything have been any easier with the passport from the #1 country on the list. Yes a few times I had to fill out some extra paperwork.

America has a VERY STRONG passport. This is a bimodal distribution where most of the passports in each of the groups are equivalent to each other and the US is in group A.

LOL at United Arab Emirates passport being preferable to the USA.
It seems like this is hugely effected by covid ban right now. A large % of countries that are just enter - italy as an example - are counted as Red given the covid ban.
Yes, OP is thinking about leaving now.
This right here. Seriously. Take the time off you need. If you need less its easy to go back to work. If you need more, its great that you took time off.

And remember, time off means time off. Dare to do unproductive stuff. Everything don't have to further your career, or even your life.

I second this advice, having done it. I flew one-way from Seattle to Dublin in 2010 with no plan beyond the first week. 25ish cities and 4.5 months later, I flew back. You'll figure it out as you go.

But, a warning from experience: when you fly one-way to another country where you'll go through immigration, always pre-book travel OUT of that country as well, and have printed (on paper!) proof to show border control. Fortunately this doesn't apply between most European countries due to the Shengen area. Immigration is not the part of the trip where you want to wing it. Always make sure you understand the visa and border crossing rules in advance.

Agreed on the one way flight and immigration. Just book a separate fully refundable flight out of the country, within the required time frame (most countries it's 90 days). You pay extra for fully refundable, but you're not going to use it so it doesn't matter.

Luckily, the most skeptical country to enter as a "traveller with no plans" is the US, so if you're starting here you don't have anything to worry about. Many countries you can go through immigration without even talking to an officer these days (assuming you have proof of onward travel).

Requires a passport from a developed country though :(

I've tried the kiosks in the U.S. and Mexico and always get sent to an officer.

I don't recommend that people do this without a high risk tolerance, but I've talked to dozens of immigration officers without proof of onward travel (I managed to fill all the regular stamp pages on my last passport). Probably half of them didn't even ask, and most of the rest of them immediately accepted that I was going to buy some ticket out in a week or two. Maybe I got lucky, but I think "American software developer" just doesn't look like a real high risk to them, and I probably don't present myself as a backpacker who might run out of money while I'm there. I have brought printouts of savings and retirement account balances and such, but I've never had to show them. I would have been willing to buy a ticket out on the spot if necessary as well.

Weirdly, it's the land crossing to Canada that has always been most difficult for me. Once, after getting pulled aside to chat with an officer for 15 minutes or so, he eventually said, "so what you're telling me is that you're rich enough that you're not coming here to work in the oil field?" "Yes, exactly."

Yeah, you can get lucky. But if you actually get denied entry and put on the next flight back, you'll wish you'd printed that flight receipt. All it takes is one officer having a bad day. (Or one who doesn't like [insert part of your identity here].)
You’re right. In my experience, proof of onward travel is usually required by the airline for you to even board the flight, not by immigration officers. I don’t think I have ever had an actual immigration officer ask to see proof of onward travel.
Yeah...this advice isn't really helpful for people who can't just take off for months (parents, people taking care of sick family members, etc.).

I think it's less about getting away physically, and more about getting away psychologically. Traveling is one way to do that, but there are also many ways to do that without skipping town.

No, getting away physically definitely has an impact that can’t be achieved without physically leaving.
Of course it does, you're physically leaving. My point is that not everyone can do that. Fundamentally "time off" is a psychological thing. Traveling is one way to detach psychologically, but it's definitely not the best way for a lot of people.
> this advice isn't really helpful for people who can't just take off for months (parents, people taking care of sick family members)

Parents can absolutely do this. Slightly more preparation is required, but much less than most people think.

> I think it's less about getting away physically, and more about getting away psychologically

Was not specified by OP. Getting away physically is by far the most effective way to get away psychologically. If it's not an option (taking care of sick family members etc), then sure - work within your constraints.

Mostly agree with this.

The one think you didn't mention was why you want to or need to take a break. If you are coming from a stressful environment, then your solution might be different. I went through some ecotherapy to destress and recover. If you just have enough money saved up to travel and want to have a fun adventurous time, that is totally different break :)

Whatever you do, have fun at it

What specifically makes this an "American perspective" and not a Canadian one or a Japanese one or a Fijian one?
Those other countries know how to relax in their time off?
Yep. Took a year off.

I can't advise you because I don't know your circumstances. I would do it again, but I cannot well articulate the advantages. I'm more deeply calm. I know my priorities. I learnt to play ukulele.

I was never bored, because before I got to that state I began working on a project. When I got bored with that one I worked on another

It cost me a year's income, but I keep my expenses low and live within my means, so it wasn't a terrible burden. To prepare, I kept my expenses to 25% of my income for over a year.

I’m about 5 months into my first big break (after 10 years without one) and I didn’t really start to recover until about 3 months in. I’m still not quite recovered but have recently started coding again, which I think is great progress.

Doing this during Covid sucks because it limits everything, but, I wouldn’t have done it otherwise too so I am a bit thankful.

I think the one biggest thing that’s been helpful is to set aside free time every day with nothing planned. Just let yourself get bored for a bit! It’s amazing!

Took 1.5 years off. As others have said -- got bored, was expensive, was worth it. I would take stock of your finances before you take time off and play out a few scenarios of how long you can afford to not work. I would also advise getting a therapist or another specific life-advisor person with whom you can have scheduled time to dish -- I found it invaluable to have someone with whom I could process the disconnect that came from being unemployed when most of my friends were still on the grind. I would also advise finding time-locked habits to ground you -- e.g., always going to a farmer's market on specific days, always going to a certain gym class or other meetup. Things that you commit to doing, which are somewhat social, where the schedule is out of your control.

I did not have many goal-style plans and have some regrets about things not done, but (shrug) I think that's all of life. In my mind it's not so important to have specific goals as to have broader intentions -- e.g., following your gut, or heart, or pursuing something that's been in the back of your mind for a while.

Good luck!

I took a 5 1/2 month break to recover from burnout and find a job I didn't hate. After a couple of months or so, my brain stopped associating my skills to my previous job, and I was able to learn some new stuff that paid off later on. They key to recovery for me was finding that sweet spot where I was being productive again without putting too much pressure on myself.
If you have the funds and you're certain you don't want to be at your current role, I couldn't recommend it more. It was perhaps the best thing I've ever done for myself. I came out of that period not only with a plethora of new skills, but with a greater understanding of my resilience and capability, a more refined understanding of what I wanted out of life that enabled me to choose a job rather than take whatever would put food on my table, and I also ended up with a deepened relationship with my loved ones.

I left a job of roughly 5 years with nothing lined up because the workplace was abusive and devastated my mental and physical health, and I felt I couldn't wait any more.

I was overconfident at how quickly I'd find another role and anticipated a max of 3 months unemployed. I quit shortly before the economic impact of the pandemic, so I wound up being off for 9 months between my old job and my current job.

The downsides were that I had to worry about my finances more, that my self-confidence took a temporary hit (I realized I tied my sense of self-worth to my employment), and that I constantly felt like I should be doing more.

The best preparation I made for myself, which echoes other comments here, was imposing the discipline of structure on myself, and giving myself actionable, manageable weekly goals to keep my forward sense of momentum going, even if that was something like "cook a dish I've never cooked before."

Edit: I would also add that it's important to manage your expectations. If you have a role to return to after, or if you know with certainty you will, this is less of a factor. If you don't, even in a great tech labor market, you should anticipate the possibility of not immediately landing the role you want and plan for that accordingly.

I have done this 3 times previously (~1.5 years) and am 7 months into my current stint. It can be very monotonous and requires a great deal of self-discipline. I am fortunate that my spouse earns enough for our needs.

-- My Story --

For my first two times, I had my next role lined up but took 2-3 months before starting. I spent this time travelling and learning/researching.

For my third time, I took a year long sabbatical offered by my employer. I pursued my own research and spent a lot of time with my child.

Right now, I am 7 months into a 2? year stint to pursue my own research and augment my child's learning.

-- Some Advice --

0. Honestly ask yourself if this is for you. If you have issues with self-actualizing, budgeting, socializing, etc, then maybe this isn't the right time in your life for this.

1. Try to be clear about why you want to do this. The time goes by quickly and it can be helpful to periodically reorient towards what is meaningful.

2. Don't expect too much from yourself. The time goes by quickly and you will make yourself miserable if you have some perfect dream of what this time should look like.

3. Be prepared for boredom and loneliness. Your friends are likely still working and there is going to be a huge disparity between your free time versus theirs.

I've been privileged enough to take several extended times off between things and they've always been very important and meaningful for me. I wrote about one period like this when I switched from a technology to a psychotherapy career: http://glench.com/WhyIQuitTechAndBecameATherapist/

I think having the time and space to decompress, heal, and explore is really important and our culture doesn't really appreciate that fully. Whenever I told people I was taking time off they'd always say "oh, are you going to travel? what are you going to do?" and I always had to tell them — no, I didn't have a plan but I knew it was what I needed.

In terms of advice I'd say you should expect a period of at least a few weeks of decompression — laying around, watching TV, socializing with friends, not doing much of anything. This is something that they talk about in the homeschooling/unschooling communities after a child leaves school — it seems to take a bit of doing "nothing" to shake off some of the conditioning of schooling, and I've found the same to be true for jobs and careers and other transitions.

After that initial decompression, I'd say that many people struggle structuring their time when not in a setting that structures their time for them. This makes a lot of sense since most people have almost never had unstructured time. So I'd start trying to find ways to structure your time.

Good luck!

I am approaching one year off right now, and will probably take all of 2021 off. I really love it, but I'm also very introverted. I am working on a dream project, basically before I die I want to build something cool, that's important to me.

I think the most important thing is keep an eye on your runway, and if/when you need to get back into the work force, make sure you're still on top of whatever it is you do. For me, building this project has enabled me to stay in touch with tech trends in my field.

We are getting our health insurance through the US marketplace. If you are also American, the recent covid relief bill dropped the prices of plans by a good deal. Our premium is now 30% cheaper.

I’m in a similar boat, have a dream project I want to accomplish or atleast give it a serious go before I die, so I quit my job moved to a third world country and am basically rebuilding my toolset in ml to see if it can be used to tackle that problem
I took a year off after my first job. I got bored after six month and tried to start a company with friends. That did not go well.

Make sure your finances are in order and that you have enough money to go for significantly longer than you intent to (in case of a bad job market, difficulty finding a job, unexpected emergency, etc.). I had two years worth of living expenses covered and had a plan to go for up to five years if needed at reduced spending. Don't forget account for health insurance in your budget since you'll need to either buy your own or pay the full COBRA amount.