Financial Freedom… Now What?


While working last week I met a couple who had achieved financial freedom. They had started their own business and now were millionaires several times over who were Hawaii locals. They said they’d really never left Hawaii, but did have some desire to travel before they got too old. They’ve spent their whole lives building their business and working 60-80 hours a week and they’ve finally reached the point where they can do whatever they want. But what should they do?

Money really isn’t an issue, but they also don’t have any employees for their business so they’d have to hire one to manage it while they’re gone or to give them full freedom of time. Having grown up and not really traveled out of the area they’re not too sure where they’d like to go since they’re not really used to going anywhere.

I told them about my blog and thought it’d be interesting to hear reader’s responses so I’m curious what you guys would do in their scenario.

If you were in your 50’s and had enough money and time to do whatever you wanted (within reason) what would you do? Your budget would be about $150,000 a year.

Feel free to share your responses below. Also share any stories if you know anyone in a similar situation and what they do.

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34 Comments on "Financial Freedom… Now What?"

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That is the penaly for success. You will get bored, once you made it. I would volunteer and give to the poor. Serve people
.-= Moneymonk´s last blog ..Friday Quote =-.

Simple in France
Well, first of all, I would have stopped working long ago. I don’t need 150K per year to be financially independent. Hah! I like the idea of slowly touring the world–you could rent a place in a country you want to visit, spend a few months learning the language, take a few trips to different places within the country etc. I’d get rid of the business unless running it brought me some kind of serious joy. You know what else might be fun–if they’re feeling entrepreneurial, they could adopt a village or region in a country they love by creating… Read more »
Worsted Knitt

First I’d travel around the world, but not by plane, but train, ships, walking! I’d take at least a year to do this. After that I might volunteer in a social or environmental project in some interesting country I fell in love with while I was travelling the world. And then I think I’d come back home and see what’s changed there, and enjoy my family and the places I know.
.-= Worsted Knitt´s last blog ..What I knit while travelling in Japan =-.

Houseswap! If they live in hawaii there are a bunch of people who would love to swap houses with them. There is this site called that i’ve used. I’m swapping with someone who lives in downtown San Fran. Soo cool. Go live in a big city for a week or so. New York City, catch some broadway shows, play tourist. Also just to throw something crazy out there, I’d recommend Kilimanjaro. Like the tallest peak in Africa. It is not a technical climb. It’s basically an extended hike for 5-7 days. They have porters that carry your supplies up,… Read more »
Little House

I’m a history buff, so if I were in their position I’d spend a summer traveling around Europe (in style!) I’d want to spend enough time in each country, so I think I’d rent a nice flat, borrow some bikes, and spend a few weeks in each city: Paris, Rome, London, Munich, Barcelona, and Athens. This is just the start!

I’m guessing, however, that they may not be able to take off a few months since they run their own business. Maybe just a few weeks in Europe would do :).
.-= Little House´s last blog ..Inexpensive, Simple Pleasures =-.

Moon Hussain

Hawaii sounds delicious. I’d definitely travel to other places. Take a good year to do that. I don’t know how they’d go about planning it.. do they have family that would love to get involved in the business?

If so, train him/her, ask for weekly updates as they travel. Hawaii does sound heavenly. *sigh*
.-= Moon Hussain´s last blog ..Fun Friday Round-Up: Delicious Blog Chowder! =-.

LenciB: Falling Into favor

I’m with the majority: I’d travel the world. I’ve sell the business after saving a ton of money. I’d give a bunch of it away…giving brings me joy. And I’d spend my life painting (something i enjoy doing) and seeing the world and helping others: volunteering. 🙂
.-= LenciB: Falling Into favor´s last blog ..His Gifts to all Alike =-.

Roshawn @ Watson Inc

I am also with the majority. I would travel both abroad and locally. I would also try to go to some movie premieres and c.d. release parties. I would also build my dream home if it wasn’t already done. I don’t think I would sell the business though.
.-= Roshawn @ Watson Inc´s last blog ..It’s Tax Time, Are You Ready? =-.

Scott Barron
I’ve always wanted to follow my roots back to County Cork Ireland and figure out why we ever left. It would be fun to locate and meet the Barron’s of the world. I would still need something job/work related to keep my sanity. The joy of owning an online business is that we can take it anywhere that has internet connections. I always feel my best when researching and learning. Truthfully, the 50’s are not that far away for me. Even on a 150K budget, I’d still want something to do & feel proud of. I’m too much of a… Read more »
I’d wish I thought about what to do a bit sooner. It’s great they have options, but they can’t get the time back… Of course they may have loved setting up this business and working 60-80 hours, I’m not commenting on them specifically. The good news is I had a wake up call on this when I sold out for a modest sum of a start-up I founded, and took a couple of months off. Suffice to say it told me I don’t like doing nothing. Have a plan people, have a plan. 🙂 The bad news is I don’t… Read more »
Jarrod@ Optimistic Journey

I’d rent a Yacht, (I could buy one but since the budgets $150,000 I think I’ll play it smart) and travel. Invest some into stocks and give some away to charity.

Very encouraging post Ryan!
.-= Jarrod@ Optimistic Journey´s last blog ..Six Phrases To Eliminate From Your Vocabulary =-.


What a tricky question! For me, it is a pity that this couple have spent their whole life getting millionaires without “getting what they wanted”. Now, according to your point of view they “can do whatever they want”…
I think this is not true. We always can do whatever we REALLY want.
What would I do if I were millionaire? I would follow my passion, as I am diong it right now… The only difference is that I could afford some expensive toys…
All the best,
.-= Boris´s last blog ..Three ways to stay detached from the immediate result =-.

Money Reasons

This is one of my dreams, if I even get enough money to travel…
.-= Money Reasons´s last blog ..Dr. Phil Drops the Ball on Bad Kids in School =-.

Ricardo Villalba
I am 36 years old and I am struggling financially, but I have travel to many places, lived on a beach, NYC, and all over Washington, DC. When I was 19 I was working 3 jobs had my own place, had money to party, and I was parting. Until I got pull over and arrested for drug possession. The judge wanted to teach me a lesson and send me away for three months. During those three months I realized how beautiful and wonderful my freedom was and that I had it all wrong, it wasn’t about the money. While in… Read more »

I would travel all around the world. If you could do it for years on end, then I would probably spend 3 months in each country and really lap up the culture in each area I traveled too. I would also collect wonderful pieces from each company, like home-wares, antiques, nick-nacks etc

Lucky them 🙂
.-= Simone´s last blog ..What I learnt from starting an online business that I was not passionate about. =-.

Austin @
Austin @

I’m with the majority — I would travel too. There’s so much to see around the world!
.-= Austin @´s last blog ..How To Identify The Right Reason Before Buying a House =-.


[…] Dollars asks what to do once you’ve achieved financial freedom in Financial Freedom…Now What? I’m still working on becoming financially free, however, I see this couple’s dilemma  […]

Daniel Johnston
I totally understand this situation. It’s very typical for successful, hard working people to not know how to take breaks, or even want to take them. That’s why so many doctors and business owners never retire. I totally understand that. Once you’ve retired, you are not really contributing to the better of society. What you’re doing is rewarded yourself for all the years you’ve been working, which is great; everyone needs to be rewarded. However, you’re rewarding yourself when you aren’t going to help the world anymore, so it’s kind of self-indulgent. I don’t know if I’ll ever be able… Read more »
Daniel Johnston
I have always found it hard to take a break. I am very successful, and I know many other successful people feel this way, as well. I think the reason why this is because most of the people who are successful really enjoy their work, and don’t see a point to life if they’re not doing something the helps society. I feel completely that way, and know I just wouldn’t be able to take a long vacation like that. When you’re successful, you’re able to see that your work has the effect on people other than themselves, but is very… Read more »
Bradley Gauthier

Sell everything, buy a boat and learn to sail…
.-= Bradley Gauthier´s last blog ..Networking 101: What To Do with Those Business Cards =-.


I’m not sure, but I’ll let you know when I get there!



[…] Planting Dollars says Financial Freedom… Now What? […]

Noah Rainey

If I made 150k a year I’d probably put it in a compound interest bank account. Or at least put half of it in each year. This way I keep 75k each year and multiply it every year. The money I would make through bank account would go towards investments.
.-= Noah Rainey´s last blog ..Nofollow or Follow Links? =-.


I’d ask lots of questions – What do I love to do so much that I talk about it all day and not get tired doing it. What are my passions and how can I express it? What have I always loved to do, especially when I was a kid? If life were ideal, what does that life look like?

Maybe spend some quiet time asking some questions, and they may get the answers that are tailored to their wants and desires. Good luck! 🙂

I am grateful to live at the halfway point along the Appalachian Trail. Folks start in Georgia and start to pass through the National Park here around June. I make it a point to speak to many of these adventurous souls and more than a few are on their personal ‘walkabout’. Some confide that they are Financially Independent and took this journey for a unique life experience while others just hung it all up and are doing it on a shoestring. In both cases the sentiment at the halfway point is “What the hell was I thinking” mixed with anticipation.… Read more »

I think if I made 150K a year, not only would I be stashing at LEAST half & putting it in a compound interest account…but I certainly wouldn’t be in the financial situation I am in currently! 🙂 Investments after debt-free status is achieved (thanks Noah!) Thanks for the story!

Budgeting in the Fun Stuff
This is exactly what we are planning for…retiring in 25 years (we’ll be 52) and having enough money to do whatever we want within reason. We’re planning on taking at least 2 cruises a year. We’ll also travel around for Bonspiels (Curling tournaments…they’re even fun for spectators like me since the Curlers not on the ice are a fun group to hang out with). I’m planning to volunteer a minimum of 20 hours a week with Meals on Wheels and the Houston SPCA when we’re in town (I already volunteer when I can on the weekends, but the week is… Read more »

I’d travel, spending 1-3 months in each place. And of course spend time with my family, paint, volunteer, and work on my business. Pretty much the same thing I do now except more of it 😉
.-= Jackie´s last blog ..Do You Have a Financial Role Model? =-.

Kevin M
I’d probably buy a small farm and see if I could make money either selling the stuff I grew or through agri-tainment (letting people come visit or work on the farm for a small fee). First we’d probably travel to Europe since my wife really wants to go and I’ve only been to UK. Maybe live there temporarily, I think exposing our kids to another culture could be a benefit. Most of all, I’d start doing all those things I want to do now but get pushed aside – like building a piece of furniture, learning how to work on… Read more »
While helping out in Biloxi after the flood I met a wonderful couple. He was a master electrician and she a special ed teacher. They were retired and lived in an RV. They traveled the country looking for places that could use their skills and stayed there until the needs were met. There was a reservation they visited yearly and the rest of the year they went wherever. I think the couple you mention would be bored out of their skulls just traveling to be entertained. But there are plenty of places that could use people with obvious business skills.… Read more »
the single best thing i’ve ever done to get to know the world.

Aury (Thunderdrake)
Traveling the world is usually a given for the financially abundant. My financial freedom requirements are pretty low. Other than having my presence on the internet, basic expenses, and the ability to travel and access those that I love, my financial demands aren’t too great. If I did wind up in a vast degree of financial freedom, I’d use those funds to either work out an invention, a high quality toy, or something that would be incredibly productive to society at large. I’ll need a way to get tax breaks anyway. Hah! .-= Aury (Thunderdrake)´s last blog ..The Hoarding Dragon… Read more »
Roman Soluk

I would try to make my family happy. I would live only for them. I would give them everything!

Briefly speaking – it’s my FAMILY, they would feel this freedom first of all.
.-= Roman Soluk´s last blog ..Music and its impact on our life =-.

Personal Finance

I think traveling can be a good way of spending some of your money. It’s one of the best ways to meet new people with different culture. That would be interesting.
.-= Personal Finance´s last blog ..Sincere Millions Caused To Suffer Needlessly – A Naive Look =-.