Need advice: fresh start

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Hey everyone not sure where to post this or how to even go about it but it’s this issue I’ve been dealing with for a while now. Basically I’m seeking to start out new somewhere else far away from where I’m at now. I recently came out to the majority of my family and close friends. I’m 28 years old , divorced no kids no major loans or obligations except helping my family. Since my dirvoce (ex wife) I’ve been wanted to be on my own and become dependent and get out there. I came across the fella who happened to work with me who invited me over to Hawaii, just as a trip vacation basically a backpacking trip for two weeks then back to reality here in Chicago , but within the last four months that toned changed to moving out there quitting my two jobs , (bartender and personal trainer) and just going on the adventure. I got pretty much around 2k on me saved and this far myself him and another buddy also joining us out there. What are your thoughts any advice ?

The island where we would be staying is Maui
My buddy knows a couple there willing to help us out for a season with housing, this far I only have a tent and sleeping bag a few clothes and my phone.

I’m not running away from my family , they’ve been very supportive of my decision although mostly everyone I talk to things moving to Hawaii is crazy and don’t think I’ll make it

Any advice would definitely come out handy
 

chesschess

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I've been to Hawaii, loved it so much I wanted to stay. B u t ! - there are a couple of things that immediately come to mind that you need to be aware of: First, it's a very expensive place to live even if you do have some kind of special arrangements - everything has to be flown/shipped in. Second, it is extremely expensive to get back home once you are there - you can't just drive home. An airplane and a boat are your only two options. Those are the two problems I know of. Perhaps others have other - and better - answers.
 

drpumps

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Have a co-worker that moved there a bit ago and just as chess chess said. It is a very expensive place to live. Be careful with your 2K it won't last long there. While it is an amazing place to visit and unless you are able to live in a resort you might want to put back enough to at least get you back to the mainland.
 

EllieP

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I know Dallas and Atlanta have little to compare to Hawaii, but I've visited both of these places when I was much younger, and there was something about each that attracted me to them so much. It was almost like a dream place to be.

And then I moved there. It wasn't two week in Dallas when real life set in, and it was nothing like the demo. I moved less than a year later. Atlanta was pretty much the same thing. I called a friend who lived there to ask her what I should expect if I moved there.

She told me that Atlanta is a huge place, and there's so much to do it's mind boggling. And the sooner I realize that I'll do none of it when I move there the better I will be. And she was right. I spent so much time trying to make a living that I didn't have time for living.

Just manage your expectations and manage your future guests' expectations too. I now live about an hour from Disney and guess where company from out of state wants to go?
 

MisterB

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Be sure to do some research about cost of living in Hawaii; specifically Maui. Two weeks backpacking on Holiday is vastly different than what you'll experience when that portion of your visit is done. Especially as the $$$ starts to dwindle.

With bartending experience, getting a job in such a tourist destination should be no problem. Housing costs are pricey. You may need roommate(s). That's an experience unto itself if you've not experienced that!

Pretty much everything else, from groceries to gasoline costs more than living on the Mainland. That because almost everything is "imported" from elsewhere. Most by ships. Be sure to factor that in as you make plans.

With that in mind, I say, go for it. Life's too short not to be happy. Ask yourself this question: Would you always suffer from "What if" regrets if you don't try this new life adventure?

Just make sure your eyes are wide open and you completely understand that your life as a resident will be vastly different from your time as a tourist. Best Wishes to you!
 

Hairylegs

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Any advise? Sad to throw cold water on the plans, but it's a really, really bad idea. Unless you are planning on going on welfare, $2000. isn't going very far. One ER visit for a messed up knee or leg after swimming, and you are toast. Stay home, nurse your wounds, get a decent job and sock away some money. THEN investigate what you can or cannot do in Hawaii. I tried moving to the Big Island about 10 years ago as a highly paid professional, and my colleagues literally laughed in my face. The weather is great, the scenery spectacular, but the reality is bone crunching. Best of luck. It might not be what you want to hear, but someone had to say it.
 

KuronoB

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tl;dr at bottom.

I came across the fella who happened to work with me who invited me over to Hawaii, just as a trip vacation basically a backpacking trip for two weeks then back to reality here in Chicago , but within the last four months that toned changed to moving out there quitting my two jobs , (bartender and personal trainer) and just going on the adventure. I got pretty much around 2k on me saved and this far myself him and another buddy also joining us out there. What are your thoughts any advice ?

Don't do it, at least not yet. This looks like you're doing something drastic because of your recent divorce, like how people have a midlife crisis or something. Admittedly, you don't have much holding you in Chicago, you're free from a bad marriage, and you're young and adventure-hungry, so you *could* do this. But this is real life, not a movie or TV show, and your finances are pretty bad. Take some time to think about what you want to accomplish. Are you looking for a 2 week vacation like you were initially, or are you really looking for a fresh start like the thread is titled?

Taking 2 weeks to backpack is fine if you just want a vacation. But the point of a fresh start is to set yourself up for future success. In what way would moving to Maui help make you more successful in the future? Is Hawaii a better place to live or work? The weather is nicer than Chicago's winter cold, but cost of living is a lot higher (60% higher if you compare Chicago to Honolulu on bankrate.com), and it isn't clear that you'd earn 60% more as a bartender and personal trainer there. Yes, you think you can get housing for a little while, but then what? Some people have wound up homeless because they moved far away on a whim, their housing situation falls through for an unforeseen reason, and they can't support themselves. Maybe it will turn out that the couple your buddy knows doesn't really like the idea of strangers staying with them. $2000 in savings can quickly run out. It doesn't sound like you've looked into lining up a job in Hawaii yet. This fresh start is looking precarious. Your family seems supportive, but are supportive enough to buy you a plane ticket home and help you get back on your feet if things go badly?

tl;dr
Don't do it yet. Pause, think about what you want to achieve, and then decide if you need a vacation or fresh start. If you want a fresh start, plan out what you need in order to be successful, and then decide on Hawaii or other places based on those criteria. Saving up 3 months of living expenses couldn't hurt either.
 
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Go on a reconnaissance trip and figure out exactly what you'll need to do to move out there. You sound like you need a holiday at least. Obviously, if it was easy, everybody would do it, but that doesn't mean it's not possible.
 

Phil Ayesho

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if you want to change your life dramatically- do it NOW.
At 28- with no kids, no mortgage, no car payment, and hopefully not a lot of debt to service, you will never again have a situation where you CAN live as cheaply as you do now.


Yes- its expensive- and yet folks are born there and manage to live there every generation... And coming from Chicago- it won't seem all THAT expensive. Like- Pineapple and fresh fish are drastically cheaper in hawaii than in chicago.

Maui is undoubtedly the most expensive place to live in Hawaii- but there are several islands and resorts that might hire a bartender and trainer on all of them. Travel among the islands is affordable.

Expect to live in mean circumstances, with roomates, especially if you plan to live near any water or bigger city.
It will take time to acclimate to the costs- and the limitations.
But the best way to make such a transplant while young before your career is set and your costs and debts have risen to match your income.

Over time you will make connections... professionally and personally, and thru them get a better lay of the land and find out how to live there within your means. Once there a few years you will be more in the know when an affordable house or flat comes up- have friends willing to donate a used fridge or couch, and be able to craft an island life that is comfortable.

If you want a change- the time to do it is when you have the least to lose. The least to pay. and the freedom to earn shit wages and still survive.
 

F_Man

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Also, would you be moving there with the idea that you are dependent on a (possibly shallow) friendship or relationship, and that the housing for you would be on a friendly basis with no payment etc? These are all big IFs, that can turn an adventure into a hell. If you don't really know the people whom you are about to trust making these big decisions, I'd get to know the situation and the people better first. Murphy's law is strange, it can bring loads of fun, but also shit. Arrangements that provide your housing on a friend's word would really need to be written, as if contracts, stating all the necessary basics, rules, expectations, finances etc. Unless you are an adventurer in your heart and can take it all, including the possible misadventures that crooked or unreliable or changing situations can bring. 2 K of money does not a wide margin for Murphy's law provide.
 
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deleted875903

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I live on Maui. The resorts are always looking for experienced bartenders. I’ve worked 17 years at one of the most popular ones at the Kaanapali Resort Area. I won’t name the resort because they don’t pay me for promoting.

Anyway the yearly pay for the senior bartenders at XYZ resort is right at $90,000.00. That’s tips and hourly combined. Bring a resume with you.

Did I mention Little Beach, it’s a nude beach on the south side of the island. That’s my hangout on my days off. Hope you have fun.
 
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stustu

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All good advise. The ends and outs of making a major change are mind boggling.
I would add. You're a good looking young man (assuming you are the avatar).
Go with a nice pair of slacks (crotch forward) and a dress shirt. Resumes and
letter of recommendation from previous employers and professionals in your
area. Plan to hit the pavement asap and get a job bartending or waiting tables.
Use your good looks and be the best server ever.
If you don't go now - you never will.
I had an opportunity to go to Australia when I was 22.
I did not go - regretted it for 47 years.
(Australian men are HOT)
Good luck,
 
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someperson

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Hey everyone not sure where to post this or how to even go about it but it’s this issue I’ve been dealing with for a while now. Basically I’m seeking to start out new somewhere else far away from where I’m at now. I recently came out to the majority of my family and close friends. I’m 28 years old , divorced no kids no major loans or obligations except helping my family. Since my dirvoce (ex wife) I’ve been wanted to be on my own and become dependent and get out there. I came across the fella who happened to work with me who invited me over to Hawaii, just as a trip vacation basically a backpacking trip for two weeks then back to reality here in Chicago , but within the last four months that toned changed to moving out there quitting my two jobs , (bartender and personal trainer) and just going on the adventure. I got pretty much around 2k on me saved and this far myself him and another buddy also joining us out there. What are your thoughts any advice ?

The island where we would be staying is Maui
My buddy knows a couple there willing to help us out for a season with housing, this far I only have a tent and sleeping bag a few clothes and my phone.

I’m not running away from my family , they’ve been very supportive of my decision although mostly everyone I talk to things moving to Hawaii is crazy and don’t think I’ll make it

Any advice would definitely come out handy
2,000 will not even buy a plane ticket