Would You Take A Steep Pay Cut To Live In Paradise?

An interesting thing occurred to me today.  I’m here in Honolulu, Hawaii on vacation and I decided to Google the state manager of a major wealth management company one morning.  As a personal finance blogger, working as a financial advisor for a wealth management firm is about as synergistic a offline/online combo as can be!  Financial Advisers help clients in wealth accumulation, wealth preservation, and wealth transfer strategies through comprehensive financial planning.  The process includes asset allocation, portfolio management, liability management, tax minimization, and asset protection.  Hey, sounds exactly like what I write about on Financial Samurai!

To my surprise, the state branch manager responded the same day and mentioned he’d be happy to meet up over a cup of morning coffee.  I met up with Jack for one full hour and at the end of the conversation he asked me, “So what do you think Sam?  Are you interested in joining the firm?”  Wow, did I just get a job offer after just one hour and meeting someone for the first time? I thought to myself.

I told Jack I had to think things through, but I would love to meet up with him again when I return in late May.  Jack even invited me up to his offices to have a look around and meet his colleagues, but I had to decline due to the one hour parking meter limit!  Jack gave me his card and urged me to contact him to set up lunch when I return.


I love Hawaii, and have been coming here for years.  I’ve written about Hawaii being the best place for online entrepreneurs to live and work, and I’ve always fantasized about one day moving back here myself.  The problem with Hawaii is opportunity and pay.  Furthermore, I don’t have my network of friends in Hawaii as I do in San Francisco.

After surveying five people who moved back to Honolulu from the mainland one night, I discovered that everybody comments on three things: 1) You’ll make 50% less here, but pay 50% more for everything, 2) You won’t be able to do a weekend jaunt to other parts of the country except for other islands, and 3) The lifestyle here truly is fantastic.

I’ve been slowly transitioning my life from the balls-to-the-wall type mentality, to the more balanced lifestyle approach for the past three years.  If you read my About page on Financial Samurai, one of the first things I wrote was no longer seeking to make the most amount of money anymore, but instead, seeking a more enjoyable lifestyle.  In three years, I’ve been able to build up my online properties to the point where I can live off my online income from anywhere in the world.  The income is much less than my day-job income, but nonetheless, it’s enough to survive and be happy.


If I were to take this financial advisory job in Hawaii, I’d be starting at the bottom of the rung again.  The pay is about $50,000 a year, and I have to go through a 3 year training program where only 20% of trainees make it through.  I have full confidence that if I enter the program, I will be one of the 20% to make it.  However, there are no guarantees in life, and I might just get so bored that I’d just quit before making it through.  Worse yet, maybe I won’t be able to get along with my co-workers.

One of my goals is to get my Certified Financial Planner designation (the article shows you how).  Ever since getting my MBA, I’ve come to appreciate the value of education even more.  One of the ways to overcome the fact of having to start all over is by treating the 3 year training program like getting another Master’s Degree, but actually getting paid to do so!  In these three years, I plan to get my CFP license, develop a network of friends on the island, and learn about the company’s various products and services.

If I achieve the company’s asset accumulation and revenue generation targets, Jack said I would make about $120,000 a year and I’d either continue to build my own practice, or get recruited by a senior Financial Advisor to join his/her team.  $120,000 a year sounds damn good for living in Hawaii with no mortgage or rent.  But again, there’s no guarantee I’ll make it through.

It’s hard to leave friends behind, but it’s also exciting to meet new people as well.  I would get on Craigslist and try and join a USTA tennis league team.  Through Craigslist, I’ll also see if there’s an Outdoors Club.  Perhaps I would look into joining a golf club, or a social club of golfers as well.  Everything takes time, and it certainly feels like a lot of work to re-establish a network.


My main goal is to work for myself so I can have as much freedom to do what I want, when I want.  That’s the entire Untemplater mantra.  With the combined passive income (click to see how much) that I spent 13 years developing + my current online income (which stays private), there’s no reason to ever have to work for anybody again.  However, I love the idea of working without having to work!  Grad school was incredibly rewarding because I didn’t have to worry about getting A’s.  I attended class for the pure benefit of learning.

Imagine doing something you enjoy doing without having the stress to do it well in order to make money.  Without this stress, you might very well do your job even better!  Of course, there is a risk you might get lazy and stop making that extra call, or going that extra mile for your client.  However, I bet that people who work because they enjoy the work do far better than those who have to work because they need the money in the long run.

A lot of things can happen in three years.  Perhaps Financial Samurai and the Yakezie Network will grow so big that I’ll need to dedicate my time, full-time.  Or perhaps Google will crush everything I’ve worked so hard for and I’ll be left with nothing.  What I do know is that after 3 years, at least I’ll have my CFP (you not only need to pass the courses, but need many relevant hours of work experience to get the designation) along with my MBA.  Only 20% of Jack’s Financial Advisers have their CFP’s, so it’s not necessary to do a great job in the FA business as many of them are making hundreds of thousands of dollars, if not millions a year.  I just think it’s a worthwhile designation to have anyway.


There’s so much stuff I would have to do to make the move to paradise.  I’d have to sell my house that I just refinanced, engineer my own layoff, say goodbye to all my friends and clients, and get registered for the Series 66 and insurance designation to sell fee based products.  There are many more things I would need to do to make the transition smooth.

Taking a huge pay cut is psychologically difficult thing to overcome and there are no guarantees I will get along with my new co-workers and find a good network of friends to hang out with in Hawaii.  That said, I’m generally always a very optimistic and happy person, so I’m not too worried about not being happy in paradise.

Amazingly enough, I wouldn’t have to do anything as it relates to my online business thanks to the internet.  My recent “Get On The Map” product can be done just as easily here in Honolulu as in San Francisco.  Finally, being closer to close family is also a big bonus.  Ahhh, decisions indecisions.

Can’t Make It To Hawaii But Want Another Great Place To Vacation?

Rent my place in Lake Tahoe! I’ve got a fantastic five diamond rated two bedroom, two bathroom condominium at The Resort At Squaw Creek in Lake Tahoe. There’s ski-in/ski-out, three outdoor hot tubs, three heated pools, a spa, a gym, several gourmet restaurants, fantastic children and family activities, a golf course on site, amazing hiking, kayaking, rafting, fishing, biking, and more! Lake Tahoe is one of the best places to vacation. You can rent book a reservation as a studio (two queens), one bedroom (one king, a pullout queen, fireplace, two TVs, kitchenette, dining table, two rooms), or entire two bedroom unit (studio and one bedroom combined). Click the links for availability and click this post to see pictures and information about it. Prices are ~15% lower than anywhere you’ll find online!

Readers, what would you do if you were me?  Have you ever taken a huge pay cut and uprooted yourself and/or your family for a better lifestyle?  If so, what were your regrets and triumphs?    How much is too large of a pay cut?  If living in Hawaii is the goal, does it really matter how big the pay cut is and starting all over?





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Sam is the founder of Financial Samurai, America's fastest growing personal finance site. We believe in reaching financial independence sooner, rather than later. Slice through money's mysteries!


  1. says

    Though I haven’t done it yet, I am setting myself up to be able to take a 50% pay cut. In a few months, the only debt I will owe is my mortgage.

    It’s interesting how the things that happen on a day to day basis can instantly put our whole worldview and gameplan on the table. Did you just email that guy to get a response?

    • says

      Yep, just emailed him from Google search earlier in the week and he responded same day. Decided to do so after a mango breakfast!

      Lesson learned to reach out and give things a try. One never knows!

  2. Sydney says

    Wow that’s awesome you pretty much got a job offer on the spot like that. Very cool. It does sound like a big decision that will take a fair amount of weighing pros and cons since you’d have a lot of changes all around. The older I get the more I’m realizing that living closer to family is a big benefit, especially as our parents age and need more help. Leaving friends is tough, but it’s fairly easy to stay in touch these days compared to when we didn’t even have the internet (I feel old saying that lol). I’m sure you’d be able to make new friends if you were proactive about it. It just takes time.

    Personally I’m a big beach lover so island lifestyle sounds really nice! If you can find ways to sort through all the various transitions it would take, it could be a great lifestyle change for you. And if things don’t work out the way you hoped you could always move back, try a different home base, or give the digital nomad lifestyle a try. :) Best of luck!

  3. says

    Sounds like a good time, so why not? Seems as though you’d like to ditch the day job anyway for something new. You’ve sold yourself on it, so it’s time to take the leap. At least you’re dropping down in Hawaii where it’s warm and sunny.

    My only reservation would be how difficult it is to be a financial adviser. Starting somewhere fresh, without the same network, would make for a heck of a challenge. It’s one thing to meet new people, and another to get them to trust you with their life from 62-65 and on. It seems like too much work if you’re really looking to tone down on your commitments.

    CFP seems like a waste if you don’t need it and you’re compensation is derived entirely from commissions. You get what you earn with commissions – and you’re not going to get the ax if you don’t have some kind of education. You will get the ax if you don’t sell. Truthfully, do clients even know what a CFP is?

    • says

      It’s weird. The more education I get, the more I want because I enjoy learning and getting the piece of paper as an accomplishment. I’m discovering why some of my friends are sti in school getting their post doctorates!

      I find a CFP will help if I were to ever start my own fee based practice. Like going to grad school in Hawaii and getting paid $150,000-$250,000 over those 3 years to get a CFP. Not bad right? And can still work online.

      • says

        IDK, guess I figure there isn’t much to learn with a CFP relative to investment. I know I have a lot to learn about insurance – if the CFP covers that in-depth, it seems like a good way to fill in the gaps. Insurance is a wacky product, especially with riders and what-not for most any other derivative or coverage that you want.

        Dude, Sam, seriously – I’m jealous as all get out. I mean, I never really appreciated the retail investing world. Institutional is more fun, bigger numbers, and a more logical approach. But all things considered, Manhattan doesn’t have ANYTHING on the beaches of Hawaii. I’d take that position and run with it. I know you’ve run into plenty of investment bankers who are just drooling over the simple beauty of a good night’s sleep. Heck, even the MDs at any given bank are drooling over the deal that the major shareholder founder will see from the pitchbook on their desk. Manhattan may hide under the image of working hard and playing hard, but why not work less, play more. You’ve got that opportunity right here.

        Nevermind that this is an opportunity where you get paid to be the Samurai in real life. Someone wants a Roth? Time to bust out your calculators to show the truth! A client still wants Roth? Devise a whole-life insurance contract that provides for the same Roth-style taxation scheme well past $5k in annual contributions. That’s a gig practically made for your contrarian leanings.

        The whole “wealth management” keyword practically says that you’ll be working with the high income, high net worth clientele – the people that have everything to gain from the cold, dark corners of tax law and investment strategy often ignored by the mainstream. I’m sure the intellectual stimulation would be incredible, as no two clients would ever be the same.

        I honestly don’t know why you wouldn’t do it. All that I can say is that you’d be crazy not to do it. And of course remember those college kids who will be graduating soon – they’ll need a firm to call home, especially if its in sunny Hawaii. 😉 Who couldn’t call the beaches home?

        I don’t think you’d ever regret giving it a whirl. I do think that if you passed it up, you’d always question, for as long as you lived, how things might be different if you just picked it up and ran with it.

        • says

          You’ve touched upon something that is very true, in that perspectives changes as you get older. I hope you don’t have the perspective of downshifting already, and that you still want to live and work in Manhattan and bust your ass to get ahead! It’s a great experience.

          It’s all perspective. I can say I’ll be working a relatively low paying job at the bottom of the totem pole. Or, I can say I’m going to take a 3 year training program to learn and get a CFP and make $200,000. Funny how that is huh?

          The most fun grind still gets tiring after a while. I’ll see how lunch goes in May.

  4. eemusings says

    Impressive! You must have made a huge impression on him.

    Hawaii in that sense sounds a lot like NZ. Don’t envy your decision (though I think I can guess).

    • says

      What do you think my choice will be and why? I am far from making a choice as this just happened today.

      Seems one can really get a head in a more laid back culture because the competition is more laid back.

      • Sydney says

        That’s a good point about having an advantage being used to fast paced work where everybody else is slower!

  5. says

    I took a pay cut to become a teacher. I love what I do about 95% of the time. When I retire, I will ahve a pension and medical for life. I guess it was worth it to do what I like to do. My savings accumulation helps a great deal.

    I know you like Hawaii probably because of the sunny warm weather which is inconsistent in San Francisco. Do you really want another job?

    • says

      Loving what you do 95% of the time is incredible. I’m probably closer to 65-70%, and fading, hence, the look for something new.

      That is the question… do I really want another job? No. Do I want to learn and be in a new environment and meet new people and eat different food, yes.

  6. Kris says

    As someone who grew up in Hawaii, moved away for school, moved back 10 years later and just moved away again, I have to say that you should think about your personal future as well as financial future. If we hadn’t had kids, living there would have been fine. But when we started realizing the cost to our children it became unmanageable. Most people in Hawaii prefer not to send their kids to public schools, and private costs $20k per year. Add that to the cost of a house to fit your family (at least $550k for a small 2 bed) and you’ve effectively talked yourself out of retirement.
    If kids aren’t on your agenda, as much as you say you love being in Hawaii, it would probably be worth it to you as long as you factor in costs. Maybe I’d wait until you got your CFP license and then be good to go. It’s an amazing pace to live, but reality for us meant we had to move away. Maybe when we have more money and no kids education we’ll move back. As my husband says, the middle class is being priced out of Hawaii, and only those who are willing to live with their family in multi-generational homes or those people who are millionaires can afford it. We have a friend who is a stockbroker who makes $150-200k per year who lived with his parents until he was 34 in order to buy a house, is trying to raise his kids and send them to school without parental help, and cannot afford to send his kids to private school. He plans on sending them for high school.
    But again, if kids aren’t on the agenda, I’d say you could do it and be very happy. We do miss the beach!

    • says

      Hi Kris, thanks for your thoughts. Did I miss the post where you guys decided to move back to the mainland? If so, I gotta go check it out.

      That’s pretty nutty about your friend who made $150-200K/year and stayed w/ his parents until 34! Does he at least have a sweet house?

      I wouldn’t mind spending the $17-20K/year to send the kids to Punahou or Illiani. The good thing about coming from SF is that everywhere else is the same or cheaper. Also, I have property in Hawaii that’s paid off, so the rent/mortgage thing is zero, just maintenance and utilities. With this in mind, still a bad move to go?

  7. says

    I did it … seriously, I’m originally from So. Cal and went through the same transition many (many!) years ago when I moved to Maui. I’ve now officially lived here longer than I lived on the mainland! Every once in awhile I get hot to move back for a variety of reasons. The problem is – even with the trade-offs, you get spoiled after awhile. The weather, it’s safer and more relaxed, people are friendly, can’t beat the view, etc. There’s a good chance that one day I will finally make the move, if nothing else to be closer to family – but I don’t for a minute regret making the decision to move here. Good luck whatever you decide!

  8. says

    It sounds very tempting, and so cool that you got a job offer so soon! Giving up a paycheck is tough, but if you can cover your expenses it’s not so bad. Such a lifestyle tempts me too, but I still have to think about whether I want to do the master’s, and it would be much more affordable for me to do that where I live. Also, the GF is super happy where she works. Maybe one day we do move on to something else, though.

  9. says

    Great post Sam.
    I’m unsure if I’d take on a job to live in paradise. There is the upside of it, you’re away from the hustle and bustle and for the most part more in control. Less is more is what I’m thinking. However, I known a lot of people who went to work at resorts, cruise ships etc only to get back to their roots eventually. And when they did get back, they were so out of touch with reality. Just my my two cents.

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