Work as Play?

Have you yet found work that is so delightful that you’d do it for free? I’m talking about work that you could totally lose yourself in; work that felt more like play than work. Is this what you want? I used to think it’s what I wanted.

Yes, it’s possible, and some folks actually find such bliss. Pittsburgh Steelers’ star receiver, Hines Ward, is a great example. Whether he’s hitting or getting hit, he always bounces back up with a big ass smile on his face.

But I have a confession to make.

There is nothing I currently do for money that I would do for free.

Sometimes, I’m almost there. But my most honest answer is no. I would not continue every aspect of the work I do for free.

Which raises this question:

Could the most delightful work possibly be the freedom to not work at all?

I think so. I think it may be easier to create a life of no work, or very little work, than it is to find work that you love so much you’d do it for free. Wouldn’t creating a life with total freedom of choice, lots of free time and the resources to enjoy it be more delightful than being obligated to work?

It all starts with what you want. For your sake, I hope what you want very closely matches what you value. My dearest value is the freedom of self-determination, which is the ability to do (work on) what I want to, when I want to, and with whom I want to. I can’t even imagine working at the whim of someone else. Employment, to me, is akin to slavery.

So I’ve fashioned a life where I enjoy total freedom of self-determination. That’s what I value the most.

But more importantly, why do you work? Before you say “for the money,” dig deeper for your true motivation.

Imagine for a moment that it’s not for the money. Really, why do you work? Is it to serve others? Is it to express who you are? Or is it to create a life of liberty and the pursuit of happiness?

If you’re not working for the money, in some way you must be working for fulfillment and/or freedom. Like me, it may be easier for you to get exactly what you want once you clearly see what you want.

In this post I’ve asked nine penetrating questions that you need to answer if you want to increase your probability of work life freedom. We don’t all have the same desires, and the same methods do not work for all of us. But I’m betting you’ll find that the key to what you want lies behind the answers to these questions. Bet your life on it. Following your own inner wisdom increases the odds in your favor.

Stumble It! Stumble It!


  1. I can’t imagine that being satisfying. I too work for myself. Years ago I burned the renewal for my teaching license (I hated it!) and swore I’d never do anything for money that I didn’t love. And I’ve kept my word. I’m blessed to be able to make a living writing, speaking and counseling. Writing is my total passion. While I write my own books, I also help others write theirs. But I only work on projects that I’ll enjoy doing, no matter how much money they offer.

    For me, the key to loving your work is having faith that’s strong enough to know if you walk away from what you wouldn’t do for free, something better will be there. It’s VERY hard for most people. I’m blessed to have nurtured that kind of faith. And I do what I get paid for, for free–my blog! Love it all!

  2. Thanks Daylle, it’s always good to hear from someone who only does what they would do for free. Damn right it’s hard to only do that kind of work. It’s not as simple as some authors seem to make it. I also had the pleasure of walking away from a well-paying career to do only what I loved to do and things did not work out.

    I don’t say that to discourage anyone. I do believe that every one of us has something we can do that does pay the bills and does seem like play. It’s the getting to that point that requires some eyes-wide-open consciousness to see all the possible options. The harder questions and decisions are what to do in the meantime?

    Is it satisfying to set an objective of work-life freedom in the meantime? Absolutely, it’s better than satisfying. It’s often blissful while I continue to adjust and refine to discover my deeper veins of gold. It would appear that ultimately it depends on what we value. The freedom of self-determination is the value I hold dearest. Being able to call my own shots while I continue to explore all possible paths of bliss is what works well for me right now. I’m very grateful that “different strokes for different folks” is the way the world works. Thanks for your inspiration.

  3. I agree Tom. It took me years of being unhappy to figure out what I loved to do–often the hardest part–and how I could make a living from it. Then to be able to put myself into God’s hands and burn my teaching license renewal form. Living solely from passion driven paths isn’t for the faint of heart. It’s definitely living on the edge at times. But I ALWAYS have enough.

    I just heard from a potential client who wants to chuck her corporate job to do what she loves. The synergy has motivated me to write an article for my blog that addresses this further with a link back to your blog. I’ll post it next week.

  4. Adam Kayce : Monk at Work says:

    Could the most delightful work possibly be the freedom to not work at all?

    I’d say you’ve hit the nail on the head.

    If you do what you love, and have the finances handled so you don’t have to work if you don’t want to, then you’ve got the freedom to do it — or not — at any time.

    It’s one thing to do what you love and have it make you enough to live on; it’s another to unlink the two…

    … and then hey, once you’re free, keep doing what you love, if (and when) you want to. I just think that if you’re chained to something, even if it is something you love doing, it can become a burden.

    (I love what I do, and, I’m working on unhooking my economic engine from it, so I can do other stuff I love to do, too…)

  5. I agree Adam, that being able to do what you love, in and of itself is the best. My writing rarely feels like work except when I’m having to deal with agents or editors who are annoying. 🙂 Otherwise, it’s pleasure. My laptop has accompanied me across Europe and the US.

    I just posted something about this on my blog. I have steps about how to follow your passion for a living that I’ll publish next week. I linked back to your blog several times Tom.

  6. Adam, what a wonderful thought. Deliberately unhooking the work we love to do from our economic engine. That really is having it all, isn’t it? Just doing it because we flat out love to do it.

    Daylle, work as pleasure, thank you, that gives me a little better feel than work as play. My pleasures are usually experienced when I’ve totally relaxed into the moment. Thanks for the links I’ll check out your straightaway.

  7. Well, THIS has me thinking. At one point I needed to earn a hearty six-figure salary in order to keep my head above water. Then I bought an old car, moved into an inexpensive apartment, and cut many expenses so that I could focus on doing what I wanted (not what I had) to do. I struggled for the first couple of years and incurred debt. But finally things clicked and now I only do the kind of work I like to do (and it is very varied, which is one thing I love). Does that mean I love what I’m doing most of the time? No. No matter what you’re doing, there is going to be time when it’s drudgery. Dayelle, you say you love to write, but there must be times when the writing or editing is just not fun, but you know you have to do it. The main thing is to not show up every day for a job that you don’t enjoy doing, working with or for people you don’t appreciate, to make money for an organization you don’t care about. The funny thing for me is that MOST of the things I thought I wanted to do, I DON’T! I thought I wanted to be a big time manager with a big staff – but I really don’t like most of the hassles of managing people. I thought I’d want to be a stand-up comic, but I really don’t like telling the same jokes over and over, and I get very stressed out before and during a performance. Etc., etc. My career is a little like a rolling stone; if I don’t keep finding new things to do, eventually I resent doing the same thing over and over. Luckily, having faith, as Dayelle mentions, was something I didn’t give up on (although it was close). {I also have to say that Deah Schwartz was my first (5th grade) girlfriend, and the only girl I ever went steady with and today she looks remarkably like Dayelle – so that’s weird. (They are not the same person.)} I think the trick is to combine a healthy dose of doing the kind of work you enjoy, with people you like, ideally for a cause or organization you really care about (or for yourself). If I didn’t have that, I’d be working with Tom or someone like him to get myself there.

  8. Tom, I am always uplighted just by seeing that smile on Hines Ward’s face, even when the play was a flop. As I observe myself and others in working in ways that bring joy, I notice that a person’s natural gifts lead them to “tinker” at certain things for hours without minding. Some people tinker with music, others with comedy. I tinker with words, whether I’m getting paid for it or not. Most of us don’t have the freedom to separate work from pay, but many of us can choose work that caters to this “tinker factor.” I know I’m most fulfilled when I do this.

  9. Bill, I laughed out loud when you said that many of the things you thought you wanted, you really don’t. I’ve had the same experience, repeatedly. Like you, I love variety and I’m not fresh without many different paths to follow. I have to be self-employed. How else could I possibly make so many mistakes and still be smiling?

    Bonnie, yep Hines is a wonderful role model. His vigor and enthusiasm is contagious. I liked reading about your “tinker factor.” I guess mine is pioneering different business methods that allow me to be myself. To pioneer is a value leave well enough alone, ever. 🙂 Thank you both for sharing so much of yourself in this delicious discussion.

  10. Steve Shapiro says:

    Hi Tom,

    Great post, great questions, and great comments.

    You pose an interesting thought: Could the most delightful work possibly be the freedom to not work at all?

    I guess it depends on how you define the word “work.” I have a career with a nice income. But I certainly don’t think of it as work. The more I make, the more I pump back into the business. Why? Because I love what I do. And the more I invest in it, the more I get to do it. I would love to do more speeches in front of more audiences in more countries around the world (I am a professional speaker and author).

    I admit, I am a bit lucky having stumbled on something that is a true passion. And it is interesting how what I am doing brings me back full circle to what I enjoyed doing as a kid: being on stage (playing the sax). At one stage in my life I wanted to be a TV game show host. Although I’m not sure that is still my calling, I am working on a TV show that has elements of a live audience and that level of excitement. Sometimes you can discover you “calling” by looking at your childhood dreams.

    I always say, focus on your passion, skills, value. Find what you love to do, what you are good at, and what the world values. You can never go wrong with that. I then outsource everything else (to designers, agents, managers, assistants, etc).

    I have an article on “Compass Driven Strategic Planning” on my website that might be relevant to this discussion.

    Tom, thanks for the great work and for spreading a much needed message.

  11. Steve Shapiro says:

    Tom, thanks for the very kind words. Here is the link to my article on Compass Driven Strategic Planning:

    My most recent entry may also be of interest. It is a 5 minute reading from my book “Goal-Free Living.” In it I discuss that maybe the key to happiness (in work and in life) is “wanting what you have.” There is a story of a prostitute that might resonate with people who are working in dissatisfying jobs.

    All the best.

  12. Steve, thank you for your insightful comment. Will you please respond to this comment with a link to the article you referenced? I looked around on your website and couldn’t find it.

    Yes even the word work can be interesting. Some see it as exertion or toil but the definition I like is productive activity. God bless you for the wonderful example you’ve shown us. Obviously your “work” is play for you and you’ve found your natural calling.

    Many others have not yet for a multitude of reasons. That’s why I write this blog. Can you imagine the majority of folks loving their work as much as you do? That would be such an enthusiastic world to live in. Thanks very much for your support.

  13. Ricardo Semler (author of ‘Maverick’) sums it up well with this quote:

    “Work is the arch enemy of Free Time” – taken from another of his books, ‘The Seven Day Weekend’.

    A great read.

    mark mcclure

    Mark McClures last blog post..Be Careful What You Wish For – Start Now!

  14. I agree that we can create a life of freedom where we can choose to work or not to work. In my opinion, building passive income is a good way to achieve that. Building passive income takes time, but once it’s done the freedom is yours.


  1. […] and others feel that some of it needs to be like work. That’s what I examined in this post, Work as Play? I keep changing my mind on that one but that’s not what I want to address in this post. Or do […]

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