Sail the Caribbean or stay at Megacorp

[felizcortez]

My wife and I are 30 and 33.  Currently have $1.1M in assets with no debt and do not own a home.  I have been at the same job for 14 years and make about $240k per year.  I was recently asked if I'd like to interview for my bosses job who just left the company which would probably bump up the pay to about 300k.  A large additional piece of compensation would be stock that would vest in 4 years.

Prior to this chance to interview we were planning to quit in July after a few bonus checks came in, buy a boat and sail the Caribbean for a year or two.  Neither of us really enjoy the location of the US where we currently live.  Sailing the caribbean has been a major dream of ours for the last few years and we have taken a bunch of sailing lessons and talked to a few people who have done it in the past.

Current spending in a HCOL area is $52k per year with $21.5k of that in rent with an additional $6.5k of vacation and lasik surgery (electives that don't have to repeat).

A few thoughts:

• If I took the job I couldn't see doing it for more than 2 years which rules out the stock compensation.  It would be a nice additional padding to the stash as that would cement the stash above the 4% withdraw rate.  In addition, I'm a bit burned out at the moment.
• We both really want to take this sailing trip and getting it in before we potentially have children would definitely make it easier.
• I'm pretty sure I'm falling victim to the OMY trap here since at the asset level we have we should be able to generate $44k per year and by the time we left in July we would have about another 100k saved bumping that up to $48k.  Now assuming we bought a 50k boat (all in with outfitting for the trip max budget) it would generate $46k, but rent expense would basically go away.
• I get hung up on this because we are young and in a very good position financially.  I keep coming back to well the promotion would be a lot more stress and travel and would definitely delay our dream.  I get concerned that we'll never do it if we continue to push out.  I have also tried framing this in my head by asking myself whether I would stay in my current position for 2 more years which would have a very similar impact on the stash.  The answer I keep coming back to is no.
• If we can earn any money (which is a strong possibility in retirement) to decrease the draw on the portfolio then the investment gains overtime will do the work for me so why am I stressing over it so much.
• I'm not averse to going back to work in the future if needed, but it would be very nice to get it all out of the way with the high earning potential that we have currently.  I'm confident I can get another 6 figure job (have had multiple offers) may not be quite as high, but we wouldn't starve.

Thought I would post this up and see what the forums say.

Should I stay or should I go :).

[Jtrey17]

What a great problem to have! Good for you! I would GO!!

[FrugalZony]

...... I have also tried framing this in my head by asking myself whether I would stay in my current position for 2 more years which would have a very similar impact on the stash.  The answer I keep coming back to is no
.............
Thought I would post this up and see what the forums say.

Should I stay or should I go :).

No matter what the forums say, you have given yourself your own answer.....
And I agree with Jtrey17, what a GREAT problem to have ;)
Congratulations to the two of you for getting yourselves in this position!

[Mr_Eric]

Sounds like you already know what to do.

BTW, what job offers that salary level at such a young age?

[jzb11]

If you're burnt out and you have the means, why delay?

Go on the trip and FIRE. It's not worth being miserably or stressed out for extra money that you don't really need.

Worst case scenario you can go back to work after the trip if your finances don't work out, or you can consult as a side gig for some cash here and there when you get back. You're a top performer who has the intangible skills to lead an organization at a high level - you will always be able to find a job and earn an income if that's what you need to do.

[pbkmaine]

Go! And if and when you do go back to work, put the "sabbatical year(s)" right on your resume. It's becoming much more common now, and presented right, can show guts and initiative.

[aspiringnomad]

Listen to your gut (and Enya) and sail away.

[Bateaux]

Work two more years.  Four if you can stand it. Give the economy a chance to recover and get a nicer boat.  The 50k boat will have you doing tons of repairs just to set sail.

[forumname123]

^Yuck to what he said. Go man!

[mxt0133]

Your story reminds me a page of the Dr. Seuss book 'All the places you'll go'.  The page describes a place where everyone is just waiting, waiting for something to happen.  Waiting to make more money, waiting to get just one more promotion, waiting for the perfect time to do something.  All the while life is just passing them by.

For most here time is the most precious resource, as we all make enough to keep our selves feed and sheltered.  You waiting another year or two to earn another 100k or so vs delaying something that you and your wife have been planning and preparing for seems risky.  Risky that you will never get to actually go, so many things can happen in two years, your wife can get pregnant, you might get yet another promotion or another job with even more pay, ect.  The good thing is choose to delay doesn't really pose any real risks either, so you delay your trip, or you end up starting a family and be FIRE by the time your kids are 5-7 and then you can go on a life long journey with your family.

You and your wife will never be this young again and the risks of going seems to be minimal to your overall goals.  If you can live on 52k while making 240k, it seems pretty likely that a 1.1 million stash will last you a few years.  Which should be enough time to find a similar position or a even better one. 

But it doesn't have to be all or nothing.  Why don't you try to work out a sabbatical with your employer or at least leave in good enough terms that they would not hesitate on taking you back.  Present it in a manner where this is just a life goal that you and your wife have and that you love your job but you want to do this now before starting a family.  Any manager that has blood running through their veins will understand and would surely hire you back.  Give it a try, you can't get unless you ask.

[felizcortez]

Appreciate all of the comments.

But it doesn't have to be all or nothing.  Why don't you try to work out a sabbatical with your employer or at least leave in good enough terms that they would not hesitate on taking you back.  Present it in a manner where this is just a life goal that you and your wife have and that you love your job but you want to do this now before starting a family.  Any manager that has blood running through their veins will understand and would surely hire you back.  Give it a try, you can't get unless you ask.

If I go after and interview for the new position, it is unlikely that I would be able to work out a sabbatical/Leave of Absence.  The only way I could see that one happening would be if I pass on the current opportunity since the hiring manager would be extending Political capital to put me into the promotion role. 

I am planning to have a conversation regarding the job next week, to get more information on the opportunity and also feel out the management chain.

[Think]

I can see the appeal but also imagine being on a boat will quickly get old.  I wouldn't turn down the offer.  I don't believe you have enough to retire and you'll come to regret it.  I would instead just take a three to four week vacation on a boat.  Then see how you feel about it.  The grass is always greener. 

[felizcortez]

Work two more years.  Four if you can stand it. Give the economy a chance to recover and get a nicer boat.  The 50k boat will have you doing tons of repairs just to set sail.

Depends on the size of the boat and general condition.  We've been looking at the used boat market in the sub 35 ft range.  This is on the smaller side, but with all things boats they are a load of compromises.

Good books that talk about it.

Dragged Aboard - Don Casey
Sensible Cruising - Don Casey
Cost Conscious Cruising - Lin and Larry Pardey

All recommend boats in the sub 35 ft range with simple systems.  The consensus of the books that I've read is that you will always want a larger boat, but go with the one you have now or buy smaller since costs are directly related to length.

[Tabaxus]

I'd be pretty scared about trying to FIRE on $1.1M right now, with the way the market is, especially if you plan to do something that could potentially get very expensive (sailing Caribbean for 2 years).  A major blow to your portfolio early in retirement is one of the things that can really, really screw with calculations; if this does end up being another 2008 or 2000 (or even a milder version, say a 30% drop), does your math tell you that you would be ok, even if we don't end up with another 2008->2014-style runup in the market to ease the pain over?

ETA:  That all being said, this doesn't matter too terribly much if you really are comfortable that you could come back after a few years and get a good job, even if the broader economy is in the doldrums, but you're likely to have put yourself on a much longer path to really being FIRE. 

[felizcortez]

I'd be pretty scared about trying to FIRE on $1.1M right now, with the way the market is, especially if you plan to do something that could potentially get very expensive (sailing Caribbean for 2 years).  A major blow to your portfolio early in retirement is one of the things that can really, really screw with calculations; if this does end up being another 2008 or 2000 (or even a milder version, say a 30% drop), does your math tell you that you would be ok, even if we don't end up with another 2008->2014-style runup in the market to ease the pain over?

ETA:  That all being said, this doesn't matter too terribly much if you really are comfortable that you could come back after a few years and get a good job, even if the broader economy is in the doldrums, but you're likely to have put yourself on a much longer path to really being FIRE.

From an investment perspective, I was planning on having $50k cash available and another $50k for the boat purchase/outfitting.  Anything we can do to save on the boat purchase will help to extend the total amount of time we could do this.  That should help us to ride out any investment volatility for at least 1 year maybe longer depending on total monthly expenses (most cruising blogs I've read are significantly below this amount). 

I've been investigating the sequence of returns risk associated with this and yes the current market situation is giving me pause, but in 2 years I'm sure we'll have another issue with the market as well. 

[AZDude]

If I were you, I would walk out that door TODAY and start shopping for a boat. My former landlord used to sail the Caribbean, using my rent money as part of his living expenses. You have no idea how motivating that was for me to get it together.

Dont take the job. You have enough. You are clearly a talented dude who can find work in the future to supplement your investment income. My family and I live well in a LCOL area for less than $46K a year. Quit in July, buy a boat, take your trip, and then pick a LCOL area to raise your children.

Good luck!

[Nancy]

Listen to your gut (and Enya) and sail away.

Hah! Yes, my vote is go now! Congrats!

[Cookie78]

At first glance it sounds to me like you've done your homework about sailing and saved enough money. I'd say go for it.

[felizcortez]

At first glance it sounds to me like you've done your homework about sailing and saved enough money. I'd say go for it.

Have taken a bunch of classes and actually teach sailing lessons for the club I'm in to get free sailing credits and get out on the water.  This has really lowered the cost of improving our sailing skills.

[felizcortez]

Just as a frame of reference, I recently interviewed with another company in the area of the country where we want to live longer term and turned it down because of the two year commitment.  That would have required a corporate move and likely would have burned the bridge with my contact at that company because he stuck his neck out.  I leveled with him on our plans and he told me to call him when we get back.

The attractive thing about the current opportunity is that we wouldn't have to move to take the position, but the downside is we wouldn't have to move to take the position since we don't like the area of the country we live in.

[Cookie78]

At first glance it sounds to me like you've done your homework about sailing and saved enough money. I'd say go for it.

Have taken a bunch of classes and actually teach sailing lessons for the club I'm in to get free sailing credits and get out on the water.  This has really lowered the cost of improving our sailing skills.

Ya, and in addition to that, it sounds like you've done your research on what it might cost to buy and maintain a boat and sail long term in the Caribbean.

[fattest_foot]

This is my plan for when the wife and I are FIRE (hopefully 2024). So my vote is definitely sail.

There are several good blogs about doing it, if you haven't read them. I read the Laho Wind blog last year and that's what really set my mind to sailing the Caribbean.

Best of luck to you if you decide to do it. I'd love to hear about all the preparations that go into it (learning to sail, buying the boat, etc).

[felizcortez]

This is my plan for when the wife and I are FIRE (hopefully 2024). So my vote is definitely sail.

There are several good blogs about doing it, if you haven't read them. I read the Laho Wind blog last year and that's what really set my mind to sailing the Caribbean.

Best of luck to you if you decide to do it. I'd love to hear about all the preparations that go into it (learning to sail, buying the boat, etc).

Laho Wind is good and we liked this one because they also had a dog.  When laho Wind was selling their boat we thought about putting an offer in on it, but it was a little too early at that point.
Where the Coconuts Grow - Have dogs as well.
It's a Necessity
Wicked Salty - Videos on Youtube
Untie the Lines - Videos on Youtube
Beautiful Crazy Happiness
Sail Loot Podcast

[felizcortez]

If I were you, I would walk out that door TODAY and start shopping for a boat. My former landlord used to sail the Caribbean, using my rent money as part of his living expenses. You have no idea how motivating that was for me to get it together.

Dont take the job. You have enough. You are clearly a talented dude who can find work in the future to supplement your investment income. My family and I live well in a LCOL area for less than $46K a year. Quit in July, buy a boat, take your trip, and then pick a LCOL area to raise your children.

Good luck!

Can't walk out the door today without leaving some easy money on the table, there are some strategic finance things with regards to vesting stock and bonuses that would pay out which is why July is the target.  If we left sooner, those wouldn't pay out.

[felizcortez]

At first glance it sounds to me like you've done your homework about sailing and saved enough money. I'd say go for it.

Have taken a bunch of classes and actually teach sailing lessons for the club I'm in to get free sailing credits and get out on the water.  This has really lowered the cost of improving our sailing skills.

Ya, and in addition to that, it sounds like you've done your research on what it might cost to buy and maintain a boat and sail long term in the Caribbean.

My wife was on the maintenance crew for a few of the boats in the sailing club.  That was definitely helpful.

[mizzourah2006]

This is my plan for when the wife and I are FIRE (hopefully 2024). So my vote is definitely sail.

There are several good blogs about doing it, if you haven't read them. I read the Laho Wind blog last year and that's what really set my mind to sailing the Caribbean.

Best of luck to you if you decide to do it. I'd love to hear about all the preparations that go into it (learning to sail, buying the boat, etc).

I showed this blog to my wife. I had started from the beginning, but I guess she went to the most recent update post. They used the same photographers for their engagement photos that we used for our engagement and wedding photos, haha, small world.

[Cassie]

I think you and your wife really need to examine what you really want to do. YOu are both young so no matter what you do it will probably be fine.  Personally because I am more risk adverse I would work at that high salary for a few more years. Still does not mean that is what you should do.  Sit quietly with yourself and get in touch with what you really want to do and have your wife do the same and then compare answers.

[NESailor]

That's an impressive income/stash for someone your age (which is basically my age too and I make nowhere near as much:).  I do have a lot of experience sailing, racing, and fixing boats (currently own 3 vessels with another one being built).  Make sure you do some real work with fiberglass and epoxy before you get out.  It's not difficult and it can even be fun.

All that said - if I had a million bucks, no kids, and a wife who likes sailing I'd be packing my bags right after I finish this post. 

[soccerluvof4]

Go! your young.

[SeanMC]

Go watch the first 15 minutes of the Pixar movie "Up" (whether you've already seen it or not).

Then make your choice.

[fa]

That's an impressive income/stash for someone your age (which is basically my age too and I make nowhere near as much:).  I do have a lot of experience sailing, racing, and fixing boats (currently own 3 vessels with another one being built).  Make sure you do some real work with fiberglass and epoxy before you get out.  It's not difficult and it can even be fun.

All that said - if I had a million bucks, no kids, and a wife who likes sailing I'd be packing my bags right after I finish this post.

+1.  Yup.  Me too.  I can already feel the wind in my face.

[Bateaux]

Youtube videos of cruisers keep me inspired.  The boat we want a 40 foot Cat will cost 200k plus.  I hope to live the dream come 2018.  We have over 1 million saved and it is not enough.   Two million will be enough for us.  Our portfolio just dropped from 1.35M to 1.25M so hopefully with some increased investment we will reach our goal by 2018.  Certsinly locked into work till the market hits new highs again.

[GuitarBrian]

As someone who grew up cruising on a sailboat. And I'm sitting at anchor now in Panama... Sailboats if done right are not expensive. Less than rent for sure. I figure 4k a year in maintenance, on average it is less than that.

A few tips I will share.

1. You need to want to, and enjoy fixing things. You need to be able to diagnose problems with the engines and pumps etc. Then get the parts and fix them.

2. Your size range is great. Bigger is not better. We have a 35ft center cockpit w/aft cabin. Was perfect for our family of 4. For week long stints it was OK for up to 8 people. As an owner of a 40 yr old boat, you really want to focus on hull integrity. Any delaminating would be a bad sign. (Please buy a fiberglass boat, 100%) There are lots of option in your price range. Mostly monohulls which are the frugal choice anyway. Only one motor, etc.

3. DON'T get a boat with teak decks. NO TEAK DECKS.

4. On a fiberglass hull. Brightwork does not have to be nice. It is superficial, for looks only. BUT, if you want a perfect gleaming paint job... It can be a lot of work. A REALLY lot of work. In the sun, with chemicals that may cause cancer in California.

5. If your desire is to not spend time at the dock. Doing things (fishing/diving/snorkeling etc) get a good dingy. This will make ALL the difference. I would recommend a 12' RIB. If you don't have davits to store it, you will need a more compact storage system. We have seen some many failures (some our own) in this matter.. Our second inflatable is the Achilles SG-124. Still going after 20 years of 6 months a year in the sun and hard use. Pair that with a 15hp, covers water at 22kts. We resupplied for 2 years 40 miles from the closest town. Every week 80 miles round trip. This is the biggest gear related recommendation, I can't stress it enough. You want a dingy that you can stand on the edge and lift water/fuel/groceries without it flexing all over the place. The Achilles has an aluminum locking floor, it doesn't flex. You can't get a wood or inflatable floor to be stable enough to work from. They squish when you walk, don't plane correctly with weight in the boat. I can go on...

6. Keep systems simple. Do you really need that expensive chart plotter? Electronics will fail, get stolen, become outdated...

7. When outfitting the boat. Get ample solar power, maybe a wind generator. They will pay for themselves, you don't want to run the generator/main motor w/alternator 2 hrs a day to keep the batteries up for the refrigerator. Start with 250 watts... maybe add more. You will need to figure out where to mount them, that is the challenge.

8. Go live your dream. Come see me in Panama sometime :)

There is a well built Ingrid? <-- pretty sure on this.. 38 in the bay here. The guy has about 10k in it. He would sell for that, most likely less. It isn't pretty, but a very well built and easy to maintain cruising boat. Boats can be substantially cheaper depending on where they are. If you want a real bargain, look in the South Pacific, or here in Panama... Equador... anywhere that people end up, and are finished. That is the time to be standing there, buying. The east coast of the US can be good as well, there are a LOT of boats to choose from.

[Bateaux]

Some locals have lived their dream for a year.  They refitted a 32 Westsail themselves.  See Sundowner Sails Again on Youtube.  Currently sailing Panama and Columbia.

[dragoncar]

I hear you, especially on the point that while you could always return to work, it's unlikely you will have the same earning potential after too long out of the game.  Maybe we are both being too pessimistic about our chances in the future, but I still think the status quo is always the easiest (I also hate job hunting/interviewing).

On the new job, what area of the country do you live?  Does your wife work?

Where I am, going from $240k to $300k is a $35k bump after taxes.  Nice cash, but nothing to change my life plans over.

I want to tell you to go sail, but I have to admit on my end I've been sticking it out part-time for the high $/hr.  Unfortunately, I will probably end up doing this until something forces my hand.  I'm at the point where I could cover my basic and regular expenses, but there are still so many "what ifs" in my future.

You know what they say... "make hay while the sun shines."  For all we know, there's another 1-2 years of gravy and the economy could tank for another 5 years.  I'd rather lose my job in 2 year and have the extra cash than quit today and angst about paper investment losses while unemployed.

P.S. The dollar being strong now is also a great reason to travel soon... no idea if that will last.

[felizcortez]

As someone who grew up cruising on a sailboat. And I'm sitting at anchor now in Panama... Sailboats if done right are not expensive. Less than rent for sure. I figure 4k a year in maintenance, on average it is less than that.

A few tips I will share.

1. You need to want to, and enjoy fixing things. You need to be able to diagnose problems with the engines and pumps etc. Then get the parts and fix them.

2. Your size range is great. Bigger is not better. We have a 35ft center cockpit w/aft cabin. Was perfect for our family of 4. For week long stints it was OK for up to 8 people. As an owner of a 40 yr old boat, you really want to focus on hull integrity. Any delaminating would be a bad sign. (Please buy a fiberglass boat, 100%) There are lots of option in your price range. Mostly monohulls which are the frugal choice anyway. Only one motor, etc.

3. DON'T get a boat with teak decks. NO TEAK DECKS.

4. On a fiberglass hull. Brightwork does not have to be nice. It is superficial, for looks only. BUT, if you want a perfect gleaming paint job... It can be a lot of work. A REALLY lot of work. In the sun, with chemicals that may cause cancer in California.

5. If your desire is to not spend time at the dock. Doing things (fishing/diving/snorkeling etc) get a good dingy. This will make ALL the difference. I would recommend a 12' RIB. If you don't have davits to store it, you will need a more compact storage system. We have seen some many failures (some our own) in this matter.. Our second inflatable is the Achilles SG-124. Still going after 20 years of 6 months a year in the sun and hard use. Pair that with a 15hp, covers water at 22kts. We resupplied for 2 years 40 miles from the closest town. Every week 80 miles round trip. This is the biggest gear related recommendation, I can't stress it enough. You want a dingy that you can stand on the edge and lift water/fuel/groceries without it flexing all over the place. The Achilles has an aluminum locking floor, it doesn't flex. You can't get a wood or inflatable floor to be stable enough to work from. They squish when you walk, don't plane correctly with weight in the boat. I can go on...

6. Keep systems simple. Do you really need that expensive chart plotter? Electronics will fail, get stolen, become outdated...

7. When outfitting the boat. Get ample solar power, maybe a wind generator. They will pay for themselves, you don't want to run the generator/main motor w/alternator 2 hrs a day to keep the batteries up for the refrigerator. Start with 250 watts... maybe add more. You will need to figure out where to mount them, that is the challenge.

8. Go live your dream. Come see me in Panama sometime :)

There is a well built Ingrid? <-- pretty sure on this.. 38 in the bay here. The guy has about 10k in it. He would sell for that, most likely less. It isn't pretty, but a very well built and easy to maintain cruising boat. Boats can be substantially cheaper depending on where they are. If you want a real bargain, look in the South Pacific, or here in Panama... Equador... anywhere that people end up, and are finished. That is the time to be standing there, buying. The east coast of the US can be good as well, there are a LOT of boats to choose from.

Great Tips.  Thanks for the recommendations.

1.  I enjoy fixing things and diagnosing them.  I do most of the work on our cars.  Change the oil, replace the breaks, change water pumps etc.  Built my own amplifier out of electronics and made my own home theater speakers.  Being able to fix things and work on them isn't an issue.
2.  Fiberglass is the only choice.  Ferrocement, steel, wood, etc. have too many downsides and require way too much maintenance.
3.  Teak is expensive to take care of in terms of time for maintenance and cost to replace.  I'm fine with white fiberglass and grip on the deck.
4.  I'm more concerned about function before form.
5.  The great Dingy debate. I agree that you want one that doesn't flex.  Inflatables are a pain, but are nice from a storage stand point. You have to look at them like they are your car (bicycle for the MMM crowd).
6. What we are debating on is whether refrigeration is necessary or not.  Agree on simple systems.  I can navigate without a GPS.  For a chart plotter, I've seen people use an iPad.  I also get a discount on Garmin products through work currently, but they are still crazy expensive.  Don't need much here.
7. My wife and I definitely want to get solar panels and have been debating Wind generators.  The question I think really boils down to whether you are going to have refrigeration on the boat or not since that would be one of the primary power draws.
8.  We've looked at boats in different sections of the US, but not in other areas of the globe.  I've heard that Panama etc. can be a great place to buy them for less money since there is a huge selection.

Really appreciate the advice/knowledge

[GuitarBrian]

We did a year when I was a kid with just an icebox... We then bought a refrigeration system and converted the icebox. Didn't look back really. Buying ice was more of a pain vs solar/diesel... and running the diesel gets you hot water too :)

We didn't want to look at the boat as camping. We were planning on the long timeframe. Going on 24 years with the boat.

I like the analogy of the dingy to the car debate. Very true... except the norm is backwards. Many people go sailing with only a rowing dingy on deck. You don't know how many times we have been the only boat in the anchorage that was able to go out, even just a few miles, fishing or just exploring.

I was just looking... prices on chart plotters are much lower than they use to be... there are lots of options that are much more reasonable. Less than an iPad it looks like... I might actually retract what I said... Years ago I wanted one, they started at 3k. The times are much different now. If I was planning on doing any serious cruising... I would get a chart plotter in the 300-500 range. It will pay for itself the first unfamiliar anchorage you enter at 2am with 20kts of wind and no moon.

Lots of little things keep coming up in my head... We had to rebuild our alternator every year... it was a standard marine AC/Delco. We changed to a CS130 it lasted 8 years. 5 years on the subsequent so far. Much better design with internal fans.

Anyway, good luck!

[Reynold]

You got a job at 19 that now pays $240k?  Nice! 

I'd suggest going now if you two are thinking of having kids.  Otherwise, if you work 2 years, go sailing for a year, look for another job, get it, move there and start a family your wife is 34-35 years old.  Fertility for women does decrease quite measurably in the years post 30, and it is a lot harder to get that back then to get money if you think your skills will continue to be in demand.  While I'm sure there are people sailing around with newborns and/or very young children, it is probably both a lot more work to care for them and a boat with just 2 people, and riskier medically, so you are likely to have some time after your sailing trip where you are settled down and can save again. 

[zephyr911]

Trick question?

[NESailor]

with chemicals that may cause cancer in California.

Hahaha, good one!  I've noticed the warnings on some of the cans that we've used over the years.  I've always found it fascinating that a gorgeous gleaming white racing hull in the water often starts as an ugly duck treated with drills, grinders, and gallons of cancerous chemicals...

[felizcortez]

You got a job at 19 that now pays $240k?  Nice! 

I'd suggest going now if you two are thinking of having kids.  Otherwise, if you work 2 years, go sailing for a year, look for another job, get it, move there and start a family your wife is 34-35 years old.  Fertility for women does decrease quite measurably in the years post 30, and it is a lot harder to get that back then to get money if you think your skills will continue to be in demand.  While I'm sure there are people sailing around with newborns and/or very young children, it is probably both a lot more work to care for them and a boat with just 2 people, and riskier medically, so you are likely to have some time after your sailing trip where you are settled down and can save again.

Yeah I started working for the company before graduating from Undergrad.  Has worked out pretty well so far :).

We've definitely had the kid timeline discussion as well.  Having a newborn on a boat would be difficult, but not impossible.

[LLCoolDave]

I'm in support of you going to sail but I'm wondering about the timeline. If you quit in July, you are looking to buy right in the beginning of hurricane season. If you are going to carry comprehensive insurance they usually require the boat be on the hard during hurricane season. You may need to spend a couple weeks or months getting the boat ready. It is going to be hot and sweaty and difficult working on a boat then.

You should definitely do this before you have kids and maybe after. Once you have sailing/the sea in your blood it's hard to let go. Seems like you have good employment opportunities after a couple years of cruising but it will be hard to return to that lifestyle.

[felizcortez]

I'm in support of you going to sail but I'm wondering about the timeline. If you quit in July, you are looking to buy right in the beginning of hurricane season. If you are going to carry comprehensive insurance they usually require the boat be on the hard during hurricane season. You may need to spend a couple weeks or months getting the boat ready. It is going to be hot and sweaty and difficult working on a boat then.

You should definitely do this before you have kids and maybe after. Once you have sailing/the sea in your blood it's hard to let go. Seems like you have good employment opportunities after a couple years of cruising but it will be hard to return to that lifestyle.

We have researched hurricane season as well.  Leaving in July would give enough time to purchase a boat and do any work on it needed prior to departure in the Dec/Jan timeframe to avoid Hurricane season. 

[felizcortez]

Had a discussion with the hiring manager this morning.  Didn't disclose all my cards, but stated while professionally the job is very interesting, I am being pulled another direction for personal reasons mainly not wanting to stay in the location we currently live.  I also stated we hadn't come to a decision yet and wanted to sink up with him since I feel like we have been playing out scenarios in a vacuum.  Wasn't a surprise to him since he knew that we weren't thrilled about moving to our current location in the first place and I wasn't an immediate yes on the opportunity.

I wanted to clarify both his and my own expectations with regards to time frame in the role.  Sounds like he is looking for about a 3 year commitment which lines up with my 2-3 year expectation going into the discussion.

I told him the last thing I want to do is jump into a role where I'm not 100% committed to sticking out that time frame.  He agreed the worst thing that could happen would be that if we got 6 months in and I decided I was out.   I have worked for him in the past and stated that is not how I want to do business nor would I want to put him in that position.

My wife and I are still discussing, but this conversation pushes us more towards the just go camp.  Concerns around total dollars etc. is something we are still working through, but this one has definitely driven quite a few discussions.

We are going to a boat show this weekend so I'm anticipating that applying some more of a push towards the just go camp as well:)

[Kaminoge]

Another vote for go! The more information you add the more it seems to make sense.

I've got no interest in sailing myself but there's a book I love called "An embarrassment of mangoes". A Canadian couple who took the plunge and sailed the Caribbean for 2 years. If you enjoy reading check it out (disclaimer: I have no idea how the book would read to people who are actually in to sailing but I really enjoyed the way they describe their experiences and the local connections they made as well as with other cruisers)

[kimmarg]

We have researched hurricane season as well.  Leaving in July would give enough time to purchase a boat and do any work on it needed prior to departure in the Dec/Jan timeframe to avoid Hurricane season.

Whats "hurricane season" for insurance purposes?  National Hurricane Center was issuing advisories for Alex, first named storm of 2016 a few days ago. (which hasn't happened since the 1950s- hurricane in North Atlantic in January)

[Think]

You got a job at 19 that now pays $240k?  Nice! 

I'd suggest going now if you two are thinking of having kids.  Otherwise, if you work 2 years, go sailing for a year, look for another job, get it, move there and start a family your wife is 34-35 years old.  Fertility for women does decrease quite measurably in the years post 30, and it is a lot harder to get that back then to get money if you think your skills will continue to be in demand.  While I'm sure there are people sailing around with newborns and/or very young children, it is probably both a lot more work to care for them and a boat with just 2 people, and riskier medically, so you are likely to have some time after your sailing trip where you are settled down and can save again.

Yeah I started working for the company before graduating from Undergrad.  Has worked out pretty well so far :).

We've definitely had the kid timeline discussion as well.  Having a newborn on a boat would be difficult, but not impossible.

Easy for you to say having a newborn would be easy on a boat.  Giving birth on a boat sounds horrific.   

[faramund]

To be quantitative, at 4%, your 1.1M gives you 44000 a year. You OP implies that your base spending is 52-21.5 =30K.

So can you, for 14000 a year, cover your boating/rent/surgery/vacation money?

[TomTX]

To be quantitative, at 4%, your 1.1M gives you 44000 a year. You OP implies that your base spending is 52-21.5 =30K.

So can you, for 14000 a year, cover your boating/rent/surgery/vacation money?

Should be very doable for them. Especially with the bonuses/vesting/etc in July.

Go on the boat. Talk to the HR guy and go on Sabbatical for a year or two. If they won't make it an official Sabbatical, make it an unofficial one.

[aperture]

Congratulations on your savings and accomplishments.  I read this whole thread and initially, I was on the fence leaning towards an additional 2+ years for megacorp.  BUT - your responses to various questions and comments led me to realize that you have done your homework on the sailing, and you probably are just in the ambivalence of OMY.

I will give a  +1 to the notion that if you come back and want to work for megacorp or a sister org, you probably can.  A few years ago, I was in the position of interviewing candidates for a 6 figure job.  One of them had taken 6 - 12 months off from her prior job to travel China and SE Asia.  She answered questions unapologetically about the time away from work.   We all were a bit envious, but I do not think any of the hiring managers saw her time away from work as a strike against her.

Also +1 for the timeline of sail now because you will be better positioned to start a family while your wife is <35.  (Thirty five is a threshold age for high risk pregnancy - which sounds scarier than it probably is for 99% of women).

Regret is bullshit - do not do anything now because you will regret not having done it when you are older.  You will always live in the NOW, and if you find yourself living with regrets, it is time to facepunch your ass back into the NOW.  Learn mindfulness, meditate. Be here, NOW. 

Again congrats. Ap.

PS - keep us posted on your progress.  Thanks.