If You Were Independently Wealthy, What Would You Do For A Living?

If you were independently wealthy, what would you choose to do for a living, if anything?

Having a job is a necessary evil for those of us who like to pay their bills and enjoy things in life. Well, I guess that might not be the case if your parents are living amidst piles of cash, but by and large we all need jobs of some sort.

Recently Mrs. Frugal Rules and I were discussing an acquaintance of an acquaintance. This person is well… rich. We don’t know exactly how “rich” they are but know that they’re independently wealthy.

Due to this wealth the person in question is pretty much able to follow most opportunities that come their way. While they have lost money at times, they’ve made buckets of it too. That’s not to say they’re haphazard with their investment decisions just that they can take advantage of most opportunities that come their way. Anywho, one thing led to another and before I knew it Mrs. Frugal Rules and I were in a conversation about what we might do if we were independently wealthy.

Being Independently Wealthy Shouldn’t be an Endless Vacation


I asked a question a year or so ago about whether or not you’d leave your job after winning the lottery. From what I remember about the responses they were largely mixed but definitely pointed to not just flat out quitting working altogether. For myself, I think that would get boring awfully quickly. Sure, if I suddenly fell butt backwards into a huge pile of cash, I’d travel more frequently but an endless vacation wouldn’t become the end result of having more money.

Anyway, getting back to our conversation, it was interesting to discuss what we’d do for a living. True, we might not “need” to make money if we were independently wealthy but we decided we would still like to be somewhat productive members of society. Mrs. Frugal Rules thought about writing for fun (gasp!) not money, or opening her own coffee shop or ad agency. My ideas were a little more scattered.

If I were independently wealthy, the two things I’d likely want to do would be something like being a financial advisor for middle class families or start my own microbrewery. Completely different, I know, but those were the first two things that came to my mind as they both represent interests I’d love to pursue more if I had the resources to do so.

Bringing Reality to The Dream


I know some might say that a discussion over what you’d do for a living if you were independently wealthy is a fruitless one. I would go the other direction though. I’d much rather go through life enjoying what I’m doing and that’s a big part of what I love about being self-employed.

Before I took the plunge, I was mentally trapped in the belief that there wasn’t true and real opportunity out there. Sure, I could apply for a different job or get a promotion but I was still in roles I’d ultimately want to quit. I felt like the opportunities around me were scant and fleeting.

Fast forward a few years and I see there is opportunity all around us – you just need to be on the lookout for it and be wise about what steps you take. Take my financial advisor or microbrewery dream for example. Both would either require extensive testing or a very sizable amount of money to make happen and who knows if I’d even find success.

A few years ago I’d stop at those dead ends and just throw my hands up. Now, not so much.

As Mrs. Frugal Rules and I were discussing our dreams we turned to something I’ve seen as a distinct possibility for the past few years – turning our business into a full-fledged advertising agency.

We have the know how. We’re growing a diverse client base and we’re already doing a lot of the work we’d be doing in one anyway.

This isn’t to say that there wouldn’t be risk involved in something like this, as there very much would be, but we’re seeing that by stepping out of our comfort zone to start our business, fear and trepidation aren’t the first things that come to our minds when we think of potential opportunities. Instead, we see opportunities as they are and work to make them more of a reality and less of a pie-in-the-sky kind of thing.

Being independently wealthy means you'd be able to make your own job opportunities, or do any work you like. What would you do?

Keeping Your Feet on the Ground While Reaching For the Sky


At the risk of telling you to quit your job and follow your passion, I think this question is a relatively good one to think through. No, you may never be “rich”, but life is simply too short to be in something that makes you downright miserable. Yes, you obviously want to be able to pay your bills but you also should be able to find something that’ll make you relatively happy in life. Thinking through what you would do if you didn’t need to do it to make money can shed light on what really makes you happy. You can use that insight to better direct your career aspirations and even help guide which opportunities you seek out with your current employer.

As I think about our situation I’m fairly confident that unless buckets of Benjamins start dropping on our lawn I’ll not open a microbrewery. While that dream is one I’ll have to leave for others, that doesn’t mean I have to or should stop dreaming, rather be open to other opportunities as you never know where they might pop up or where they’ll take you.


What would you do for a living if you were independently wealthy? What is one job you’d love to have? Would you ever quit a job because you were miserable and had no job as a backup? How can thinking through this question give you insight into what really makes you happy?



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I'm the founder of Frugal Rules, a Dad, husband and veteran of the financial services industry. I'm passionate about helping people learn from my mistakes so that they can enjoy the freedom that comes from living frugally. I'm also a freelance writer, and regularly contribute to GoBankingRates, Investopedia, Lending Tree and more. If you're wanting to learn how to monetize your blog, check out my blog coaching services to see how I can help you take your site to the next level.


  • Nicola says:

    I’d love to open my own coffee shop/tea room if I could – baking cakes and making other people happy sounds good to me 🙂 a tiny part of me hopes that one day this might come true anyway, but we shall see 🙂

  • “Blog” of course! …

    No really. I’ve given this topic a lot of thought and my ultimate goal is to become a free financial adviser after I’m completely financially free myself.

  • I like the idea of helping others with their money too. As an adviser or coach.

  • Strangely I’ve thought about this before, and it seems fun to think you’d do something completely different,like open a brewery. In reality, I’d probably just keep doing eye exams but I’d do them on my terms and not worry about insurance or how many exam slots I need to fill in a day to make a profit. I would love to work exclusively with veterans and/or elderly people, my two favorite categories, but not the ones that pay the best!

  • Interesting question to think about, that’s for sure! I definitely would not be working at the same job as I am now. It simply doesn’t provide enough freedom/control over my time and schedule as I’d like, and if I was independently wealthy that’s one thing I would desire. I would most likely spend a majority of my time reading, working out, and working on projects. If we are talking Powerball money I think it would be a no-brainer: I’d spend my time looking for startups to invest in.

  • Honestly, I don’t think my life would look too different. I think you’re right about having structure and goals and not living in some kind of endless vacation, it’s nice to have purpose. I might have a little more down time if money were no issue, but otherwise, this is what I’d be doing 🙂

  • I would love to do lots of volunteer work all day long in all aspects of life. Being able to teach people how to cook and improve their reading skills and just about anything else will make me feel rewarded each and every day.

  • I would continue working for now. I enjoy what I do and my kids are still in school. Might as well make as much money as I can! With that being said, I’m not afraid of being bored at all. I have more than enough hobbies to stay busy and fulfilled.

  • I agree that it is a good question to ask ourselves for the sole reason of it might help us figure out what we truly enjoy and seeing if we can turn that into a career.

  • Kathy says:

    I always wanted to have a little clothing boutique but if we are talking super rich…like in the multi hundreds of millions, I’d love to set up a foundation that served military veterans. I’d try to learn what they were good at and then set them up in their own business so when they returned for serving their country, I could serve them.

  • Sarah says:

    Love this post!! If I didn’t have to work, I would still freelance write and blog as I really enjoy both of those things. I would also workout more, cook more and read more. Sounds simple, haha! Eventually I’d like to travel more, but our kids are so young that it’s not always a “vacation” when we do travel.

    My husband and I are getting our real estate licenses this summer and that’s always been one of our dreams! Even if we didn’t need the money, we would still do this 🙂

    • John Schmoll says:

      Thanks Sarah! Simple is good. 🙂

      Very cool on the real estate licenses – that’s a great thing to have on the side, especially when it’s fulfilling a dream.

  • Such a great question. Maybe I’d pick up skateboarding again, if I could get over my neighbors talking trash about that old guy skateboarding around the neighborhood.

  • I would love to spend more time with children. I can’t think of many jobs that I would choose to do if independently wealthy, but crafty activities have always been really engaging. It would be fun to learn some new things.

  • I think I would definitely be outside more instead of at a desk for 9+ hours a day. Things like cut wood for my wood stove, woodworking, spend more time on my blog, teach a personal finance class. The options are endless!

  • I think I’d be doing exactly what i’m doing now with the exception of doing videos for other people. I’d make documentaries, write for myself, maybe do some community outreach and speaking. I guess that last part I’m not doing right now, but mainly because I do have to earn income somehow right now. 🙂

  • Janeen says:

    I’d like to think that I’d do something generous. Support an orphanage or something. I admit that it would be tempting to spend a bit more lavishly with such a supply of money on hand. Wouldn’t it be wonderful to do little acts of kindness for people? Paying for meals at restaurants, sending people through FPU at no charge. As for career, I’d do what I am now, just with more traveling!

    • John Schmoll says:

      “Wouldn’t it be wonderful to do little acts of kindness for people?” — LOVE it! We’d definitely be looking to do stuff like that…and the traveling of course. 🙂

  • Michelle says:

    Love this post! I really do believe that I would be doing something very similar to what I’m doing now. Life is great!

  • Revanche says:

    Oh yes, I have plans for being independently wealthy, indeed! It just depends on how wealthy we’re talking. I’d like to work in animal rescue and rehab, and if I were wealthy enough, I’d start my own or fund a branch of an existing rescue that I respected.

    I also want to continue helping people with their finances, and pick up gardening again. Traveling would absolutely be on the list, depending on other projects.

    I used to joke that a friend of mine was busier in retirement than when she worked, but apparently I would find myself doing the same 🙂

    • John Schmoll says:

      Yea, the person in question is someone who has helped produce major motion pictures, music, etc. Let’s just say they’re not hurting for money.

      I love your ideas, especially the animal rescue and helping with finances. I think we’d be the same way – life is too short to not fill it with enjoyable things that also allow us to give back.

  • While I can’t say with 100% certainty, my guess is when you are on an endless vacation, it probably grows tiresome after awhile. Hard to imagine for us working folk, but as much as I like travel, I need more than that too. If I was independently wealthy, I would definitely still work but solely on projects that interest me. Financial literacy would remain a passion and I could do more without worrying about cost or profit. I like your dream of being a financial advisor and owning a microbrewery. You could hold financial education seminars at your brewery because free beer will ensure a full room, although maybe not lucid decisions. 🙂

  • We recently wrote that we’d want to be basecamp managers on Himalayan climbing expeditions, but then the Nepal earthquake gave us a reality check (if there is such a thing in hypothetical exercises). In the realm of more realistic pursuits, we have a lot of friends who own their own businesses and need help here and there with things we are good at (marketing, etc.), and we’d love to be able to help them out for cheap/free. We think that could keep us pretty busy, doing little projects to help our friends’ businesses succeed.

  • I have always wanted to be either a broadcaster for major league baseball, or a DJ for an oldies radio station. Of course when I was a DJ in college, they weren’t called oldies then!

  • Jason Butler says:

    I would get into real estate if I was independently wealthy. I would purchase a couple of quads and rent them out to young professionals who needed a place to stay for the time being. To answer the 2nd question where you asked “Would you quit a miserable job without a back up?”, I have done that before. Honestly it was one of the best decisions I’ve ever made in my life.

  • I’d LOVE to see you guys open your own agency! I know you could do it and succeed. As for us, hands down we’d minister full time. Sharing the gospel is something we LOVE to do.

  • A lot more travel. I always liked the idea of teaching / coaching as well. High school or maybe college.

  • I would love to teach for free, volunteer a lot, open a business based off giving back somehow, while charging lower than average prices for customers. Brewery sounds like a lot of fun. Sneaker store for me would be a dream.

  • Dean Dinh says:

    I’m a simple man, my definition of independently wealthy would be +$2.5million in assets. I would try grow that $2.5 million by 5% a year through either real estate rental properties or dividend growth stocks. If given the opportunity and if I did my due diligence, I would try to open a business of my own. I would quit my corporate day job in a heart beat. It’s all about enjoying life, why would you want to continue being a slave to a company?

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