Will Financial Success Follow You if You Do What You Love?

I read a lot of personal development books—probably at least two a month. Like most books of any kind, each one usually has some things worth learning and some things that aren’t valuable to me.

If there is one common theme to most of these books, it is that “following your passion” – or doing what you love to do—is the most important work we can focus on in life. According to this thinking, work should involve a number of things you really like to do and are really good at, not simply a series of tasks you do to make a living.

So far, so good, right? But sometimes the thinking goes even further. Not only will you feel better about yourself and provide more value to others, you’ll also end up making more money.

Follow your passion, the thinking goes, and the money will follow.

The classic example of the “follow your passion straight to the bank” idea is Oprah Winfrey. Oprah does what she loves, and she’s been enormously well rewarded for it. She was passionate about communicating with women when no one else in broadcasting really cared.

Oprah’s so good at it, in fact, that her salary in 2007 was estimated at $260 million by Forbes. That’s not bad for talking with people on the couch, right?

How to Be the Next Oprah

Not really… you don’t want to be the next Oprah, right? Oprah is cool because she is herself. You want to be the real you. And ideally, you’d like it to help pay some bills along the way.

Here’s how you become the real you and leverage what you’re best at.

1. Get a Unique Selling Proposition (USP). This is absolutely critical. For the four years from 2002 to 2006, my USP was that I lived in the poorest countries in the world and ran a business on the side to support my work. That was pretty cool, and when I spent time with business people in the U.S. or Europe, my introduction usually topped everyone else’s. Now I have a new USP – I’m going to every country in the world and starting my own social movement to encourage the spread of unconventional ideas. This new USP may not be as cool as living in Sierra Leone, but it still gets people’s attention. What’s your USP?

2. Become an expert. The way you become an expert is mostly by saying you are one. The more specific the niche you can nail down, the better, and you can then use that status to extend your expertise to other subjects.

3. Accept that monetization does not mean “selling out.” Just because someone gets paid to do something doesn’t mean they lack principles or integrity. It means that other people value what they do enough that they will pay for it. This is a good thing, not something to be ashamed of.

4. Follow the path of world domination decide to be remarkable, create a vision to change the world, recruit a small army, start doing stuff using the ready, fire, aim method, and eventually scale up.

What the Critics Will Say

As you might expect, your critics will tell you that you can’t make a living doing what you love. Artists don’t make any money, writers are supposed to be poor, and you should spend at least 40 hours a week working at a “real job” to support yourself so that you can have a little fun on the side. If you’ve been living an unconventional life, none of these attitudes will surprise you.

When my wife, Jolie, was a kid, she told everyone that she wanted to be an artist when she grew up. Some people said “OK,” and some people said “That’s nice,” but then someone close to her said that she couldn’t work as an artist because she would starve. When she asked what she should do instead, she was told to go into real estate.

I have a problem with the idea that artists are destined to be unsuccessful.

First of all, many of them are happy with less money, and they aren’t starving. There are real people in the world who really are starving, but most of them don’t read personal development books, and none of them really have the option of going into real estate.

Second, a lot of artists do pretty well for themselves. One of Jolie’s mentors regularly sells his work for in the $65,000-100,000 range—per painting. (He spent thirty years training to get to this level, although I’ve told Jolie I’d be happy with 10% of that rate. She’s working on it.)

Finally, the odds of financial success following you as you follow your passion probably depends to a certain degree on what you love.

A while back I picked up a copy of Guitar Hero for the Nintendo Wii. Let me just say that I’m not half-bad at it. In fact, the first few days I had it, I didn’t do much other than practicing my GNR and Rage Against the Machine riffs. But if playing Guitar Hero became my passion, do you think people would start paying me to pretend to play their favorite 80s rock anthems? It seems a difficult calling to monetize, at best.

If you love staying in bed all day and not doing anything productive, that’s also difficult. Who will pay you to sleep in? How will you create serious income based on a stated goal of being useless to society?

If you love hedge funds, on the other hand, it seems fairly easy to expect financial success to follow you as you follow your passion. I don’t have any hedge fund readers that I know of yet—if you are one, please see this link—but most of us are somewhere in between absolute poverty and extreme wealth. We aren’t aspiring Guitar Hero professionals, but we aren’t hedge fund owners either.

My Personal Story

In the end, I don’t really know if following your passion will produce financial success. It seems that it does for some people, like Oprah, and not always for others, like my friends in Africa, or the guy in Best Buy who plays some amazing Guitar Hero.

For me, the development of this site is a real-world example that tests the thesis. This year I’m spending a lot of time doing what I love—traveling and writing. I do a lot of other things too, but I made the decision last December to focus on writing and travel more than anything else.

I’m not expecting to get rich from it, but I certainly wouldn’t mind if it produced some reliable income at some point in the future. I personally know several bloggers who make more than $100,000 a year, one of them a lot more… but most of them also have their sites cluttered in ads, which I don’t want.

So we’ll wait and see. I’ll keep writing, hopefully you’ll keep reading, and at some point we’ll decide on what the next step is.

Which way will it turn out? I really don’t know.


But enough about me.

What is your passion? Are you following it regardless of the money? And if you aren’t making money from it, would you like to change that?

Will you go into real estate instead of painting because you’re worried about starving?

Will you become the next Oprah, or will you become the real you?



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  • Eric Hundin says:

    I found your blog on MSN Search. Nice writing! I will check back to read more.


  • Reese says:

    You know what’s a tough one?
    When you have a LOT of passions, and it’s darn hard to nail down just one 🙂

  • Sara says:

    My passion is, and has been for years, reading and writing. Unfortunately, in high school I did equally well in all subjects, so I chose to go into chemical engineering in college, because that’s where the money is.

    Big mistake. I have hated every single one of my classes relating to that major, and got my first A in college in linguistics, and my second in government. That was a pretty big wake-up that perhaps I wasn’t studying what I wanted to do.

    So a couple of weeks ago, I took the plunge and changed my major to English. I want to be an author, and I intend to follow up on that dream, even if it means working low-income jobs to support myself.

    I love your blog, by the way. It’s eye-opening and makes me reexamine my life, which is definitely needed.

  • Kyle Claypool says:


    I stumbled across your site via one of your comments at BigBrightBulb. Lots of great stuff here…

    I too realized a while back that my professional Guitar Hero aspirations were not meant to be (with the exception of the occasional $5 bet among friends – does that count as semi-pro?).

    I’ve always loved to travel and to work with people. As an aspiring IT consultant and entrepreneur, I get paid to do both. I may not be making millions, but at least I enjoy what I do, and you can’t put a price on that. I don’t think I’d make a very good Oprah anyway…

    Kyle / OnYourBusiness

  • Kathryn says:

    Great post! People call me peculiar because I believe things like what you posted are possible (started a blog all about being peculiar).
    I found you blog as I was looking for links for today about peculiar ideas about working at home. It seems that no matter what you are doing, there are some universal truths that ring true.
    As for the finances, it is possible to live a life without ever making a salary. It takes a budget and some common sense, but it is a life my husband and I would never give up for “real” work again.
    BTW – I’m reading “Success Through a Positive Mental Attitude” again right now! It’s always amazing to me how motivation seems to beget motivation.

  • jblee says:

    You nailed it in number 4: follow the path of world domination – create a vision to change the world.

    Most of the time, our passion is related with our vision. And following this path will reap great economic rewards. Being able to use your passion to change the world is the best vocation which one should pursue

  • Benjamin Bach says:

    Hey Chris
    I found this post when my friend Josiah Mackenzie linked to it. I now need to go thank him 🙂

    Great post. One of my favourite quotes is from Russel Simmons – ‘Stay in your lane. If you’re good enough, people will move to you.’

    Did your wife try Real Estate? It’s interesting you mention it – I am in Real Estate, but not the type that most people are in (selling homes). I work exclusively with investors. Starting out (as a 22yr old who rented), this was tough. But inch by inch, I made progress.

    You persevere, and then you achieve.

    BE Great

  • Debbie M says:

    I’ve gone the conventional route, with a government job and a pension. Unlike many of my friends, I work no more than 40 hours a week, so I do have an above-average amount of free time and vacation time.

    However, by practicing frugality at an unconventional level (in housing, transportation, and clothing especially), I have been able to travel (mostly within the US) and will be able to retire at age 52 with a paid-off house.

    I didn’t figure out my passion until last year. I wanted to be a teacher since I first started school, but I’m not good with large groups. Finally I figured out what I most like to do is work with others developing educational materials. So now I’m looking for a more fun job within my agency (a university) such as re-developing courses to put them online or helping a professor edit an academic journal.

  • Qrystal says:

    I came here thanks to IttyBiz’s twitter about the followup article to this one ..

    and I’m so glad I did. I’m about to leap into the big scary unknown “after university” world, and I’m totally gung ho about pursuing my passion and working from home. I’m just scared about it sometimes, and need to read more reassuring articles like this. I’m commenting mostly so I can receive followups from other people who are inspired by the above article! 🙂

  • Stephanie says:

    I agree with Reese – so many passions, so little time! It’s difficult to know which to put your whole heart into, and which should stay on the side (but still be a part of life!).

  • Nathan says:

    You have a great blog and I really enjoy reading it. This post was especially helpful.

  • Grace says:

    I also agree with Reese and Stephanie — I have so many passions, many in related fields, that it becomes difficult to choose one to fully flesh out and focus on.

    To give you an idea, I am part of an Improv Troupe, am involved occasionally in theatre productions sometimes as actress, sometimes as director, I work on freelance photography projects and graphic design, am very interested in cinematography, and am currently learning Korean. And those are just at the moment. There are many more interests and hobbies added to that list.

    Chris, I’m not sure if you have one already, but I believe us three, and many others, would greatly appreciate an entry related to having many passions!

  • Jen says:

    Hi Chris,

    Two of my favorite bloggers mentioned you (Zenhabits and Scott H Young), will have to thank them. While I’m a bit skeptical about some of your ideas (would be boring otherwise anyway) I liked your entry about Ohrid. Well, you want non-conformity: Last year I tried to drive by car (from Vienna) there for a few days, but the car broke down half way in Belgrad. So I stayed there for some days and on my way back stayed another night in Budapest right during the Red Bull Flight Show on the Danube. (I will try again Ohrid again, but by another route)
    And monetizing your passions? Like above, I have many things I would like doing. Good things is, they can be combined (including living in some other countries, eg Kazakhstan or Madagaskar).

  • Janice Cartier says:

    Founding a social movement? This should be a fun ride…I paint. I found you through Naomi and Leo. Love your writing, applaud your passion and will give you a standing ovation if you manage to move your ideas into mainstream America. 🙂

    When I read Friedman’s The World is Flat, I liked his premise and the facts he backed it up with. At the same time I hoped he did not mean that the world would also be homogenized. Having also lived out of this country, there is a dual respect in my heart. I adore exploring diverse cultures, and I adore being an American. If we can think a bit more spherically, a bit more creatively, perhaps there is an incredible richness and texture available to us all.

  • tippy says:

    I always had this question in my life. I really wanted to pursue art but then my dad wanted me to get a business course back in college. I ended up joining business organizations throughout college working as an artist, cartoonist & a magazine editor. I eventually landed in a series of marketing/marketing-related jobs which combines art & business. After a number of years though, I ended up having a sideline in graphic arts. I’m not starving so far. From my experiences so far, I guess you just have to follow your passion. For the ‘getting there’ part, it’s not gonna be rational and there will definitely be a lot of self-doubt and black hatting but the journey’s worth it! 🙂

  • Melanie S says:

    WOW! Amazing that I found your article at this particular time in my life. I was recently laid off (last week; b/c of the economic issues) and decided that I’d rather follow my passion of teaching art classes rather than going ‘back into the field…engineering”. The only problem is convincing my DH.

    So I am now here reading your words (which I found from someone following on Twitter). I’d like to think of it as a sign; reassurance that I MUST follow my passions. Who would want to go through life sitting inside an office while the world goes by?

    Thanks for your encouragement.

  • Monique Van Dijk says:

    Another great post…

    It is true that your ability to make money from your passions is related to the nature of what you love doing – some passions typically present easier opportunities to make a profit than others.

    However, while it may not be easy to make money in the exact form of doing what you love, there are usually plenty of opportunities to make money in some related way, especially thanks now to the accessibility of the internet. If your an artist or a creative type, sometimes the money-making opportunities surrounding your passion may not be immediately inherent so it can work well to team up with someone who works in marketing or sales to have a brainstorming session about how you can monetize your passion. (doing this is their passion – and they’ll be better at it than you). The reality is that making $$$ from your art can require an investment of your time + money into sales + marketing activities plus some business savvy. (if that sounds like your idea of hell, why not partner up with someone who IS passionate about sales + marketing and share in the profits – that way you can devote your time soley to doing what you love)

    Just like everything else, I believe that the decision and commitment to follow your passion takes persistence, dedication and hardwork… but the rewards are definitely worth it.

    Don’t give up the dream and follow the path that you think you should – the path of least resistance, 9-5 desk jobs, and 30-year mortgages… chasing money isn’t likely to lead to fulfillment and happiness but the reverse can often be true.

  • Osman Safdar says:

    Great ideas flowing out in this article, ones which I’ve been thinking about too. However, I feel there is a deeper underlying question that needs to be addressed:

    Does following our passions always lead to success? That’s what self-help authors would want us to believe. But I’ve met people who are very successful and satisfied with their lives, even though they didn’t BEGIN with the “I need to follow my passion in order to be successful” mindset. They didn’t consciously decide to follow only what they were good at. Rather they embraced the pathways life showed them.

    So, my question, and one which I think you’d be able to answer, is this:

    “Does success really depend on our choice to follow our passions and/or embracing the options life gives us? Or does success depend on our ability to overcome challenges irrespective of whether we follow our passions or not? ”

    Osman Safdar

  • Fizz says:

    #3 resonates – I definitely won’t consider myself sold out when my writing and art starts to make money. To be paid to do what you love? That sounds phenomenal.

    Just need to finally start up that Beastie Boys tribute project that has been in the works. Would any one go see that?

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    میلگرد، به فولادی که در بتن برای جبران مقاومت کششی پایین آن مورد استفاده گفته می شود .نام دیگر میلگرد آرماتور می باشد.از آنجایی که فولاد به کار رفته در سازه های بتن آرمه به شکل سیم یا آرماتور می‌باشد، با آن فولاد میلگرد گفته می شود.

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    It was only that his body did not fall forward because Degas was holding it.

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