Playing to Lose

Hello, everyone.

During my extended absence, I got caught up in a strange ordeal.  While laboring away at my “real” job, I ended up writing copy for a type of client that many independent contractors dread: the backseat driver.  As a professional, I obviously can’t name names.  But I was constantly trying to fight an uphill battle with this client to justify my word choices, getting critiqued every step of the way.  I finally realized what level of hell I was in when they told me that my words were “too upbeat and exciting.”  I was writing a brochure for a vacation resort.

So, to cut the encounter short and keep myself from going insane, I caved.  I wrote what they wanted, and made a mental note to never put myself through that again if I could avoid it.

The experience was so stressful that I decided to take an impromptu break from work, just to get my mind back in the right place.  And I came back here…to do what I love most…:).

Oftentimes, when it comes to careers, we feel forced to choose between pursuing our passions and pursuing a paycheck.  Ultimately, it boils down to a single question:  Where do you get your fulfillment from?

Personally, I became a freelance writer for two reasons:  I love freedom.  And I love to write.

And even though copywriting gets the bills paid, it’s not what gets my blood flowing in the morning.  You know what gets me excited?  Love.  Life.  And this blog.

Playing to Lose

I’ve always prided myself on the fact that Playing to Lose is ad-free, and a lot of my readers have asked me why I’ve never attempted to monetize the site.  I pull in modest numbers(close to 1,000 unique visitors/day, nothing incredible), but I’ve never tried to capitalize on my traffic with ad spaces or affiliate links.   The reason is simple.  I don’t monetize the site because I didn’t start this blog with the intent of turning it into a business venture.  I created it as an escape hatch.

You see, I spend the better part of my day working for clients that want me to write about things that don’t really matter.  My entire copywriting career is littered with vested interests and skewed viewpoints.  And so I created this place as sort of a sanctuary.  There’s nothing corporate here.  Nothing commercial.  Just me, writing about the things that matter to me.

Of course, I’m not leaving out the possibility of one day leaving copywriting behind and dedicating myself exclusively to the world of personal development.  If I could actually make a living exclusively from the work I do here, that would be an amazing dream to achieve.  But in the meantime, it’s nice to have a place that I can escape to when the stresses and pressures of the corporate world grow too large for me to bear.  It’s what keeps my true passion for writing alive while I do what I must to get the bills paid.

To me, Playing to Lose is more than an blog.  It’s an open forum for knowledge…a place where someone like me can share their thoughts with honesty, minus any corporate intervention.  It’s a place for discussion.  Perhaps my words will help someone.  Perhaps they won’t.  But knowing that they might…well, that’s worth more than any paycheck.

So take a good, hard look at your life.  Think about whether you’re pursuing your passions, or a paycheck, and ask yourself that simple question:  “Where am I getting my fulfillment from?”  Because knowing the true source of the joy in your life is what will keep you pursuing the things that you love…and stop you from wasting time on the things that don’t matter.

Thank you for reading, friends.  I’m glad that I could share my thoughts with you today, and I’m glad to have readers as exceptional as yourselves to keep the conversation alive.  Namaste…:).

As I was getting up from my daily meditation this morning and walking to my desk, I spent a little time thinking about how much my meditation room-slash-study has changed over the years.  Right now, the whole place is practically empty.  Bare.  Clean.  And that’s how I like to keep it.  But once upon a time, there were piles of clothes in the corner…stacks of boxes in the closet…a pile of empty water bottles by my chair…and a stack of papers almost a foot high on my desk.

It’s funny to think how all the detritus of our lives can slowly and sneakily add up over the years.  Over the course of almost a decade, I let things carelessly slip and fall to the floor, unmindful of the fact that I was gradually cluttering up my study and my life.  Near the end of those dark days, it felt like every walk through my study was a trip through a museum dedicated entirely to useless things.  And every day it felt just a little bit harder to breathe in there.

The Clutter Monster

I think all of us has a part of our lives that we let fill up with clutter.  Our sanctuaries…our bodies…our minds…they can all fall victim to the ravages of time and carelessness.  It’s just a matter of letting small things slip over and over again.  Letting that empty bottle sit idly on your desk.  Eating that one candy bar before going to sleep.  Putting off that one work assignment until tomorrow.  But small things have a nasty way of adding up.  And soon that soda can multiplies into a veritable in-house landfill.  That candy bar becomes an unsightly belly bulge.  And that work assignment turns into a week of sleepless nights spent trying to catch up on lost time.

Many of the catastrophes in our lives are ones that we create ourselves.  And it’s not because we’re self-destructive.  It’s just that we’re creatures of habit.

It’s easy to put off a small thing like cleaning your dish when you’re done with it, or doing a set of push-ups in the morning.  It’s easy to say you’ll do it tomorrow.  But when you start putting things off on a regular basis, you start to unknowingly set routines for yourself.  And those routines are fraught with bad habits.

So how do you keep yourself from going down that road?  Or, more realistically, if you’re already down that road, how do you get back on the right track?  It’s really not that hard.

All habits, good and bad, are created equal.  That’s the good news.  They’re all equally easy to start, but they’re also equally easy to stop.  It’s just a matter of being mindful and starting small.

The Futility of “The Big Attempt”

Some of us live with our bad habits for so long that we become desensitized to them.  But every so often, we have brief moments of clarity where we realize painfully obvious things like “Man, this room is dirty!”, or “When did I get so fat?”.  And then we try to rectify the problem with one big attempt.  But that never works.  So we end up going back to our old routines the next day, like zombies.

For some reason, these sudden moments of clarity always make us feel like the clutter in our lives is just some humongous thing that just “happened” overnight.  But it’s not.  Clutter is not a single entity.  It’s a thousand tiny bad habits, piled on top of each other.  So if you’re going to unclutter your life, you’re not going to be able to do it all in one go.  You can’t just say, “I’m going to clean my entire house today and keep it clean forever!”  That’s not how it works.

So What Does It Take?

It takes small steps.  It takes repeated effort.  But most of all, it takes the diligence and mindfulness to stop letting your bad habits accumulate.  Because once you can stop the clutter monster from growing, you can finally start cutting it down to size.

Remember how your stack of bad habits got started.  Remember how so many small acts grew into something so powerful.  That’s something I want you to think about as you go on.  Not to make you feel guilty.  But to make you realize that just as the seeds of neglect can grow into a forest of clutter…the seeds of mindfulness can grow into a forest of clarity.  But it’s entirely up to you to choose which seeds you wish to plant.  And with time, I hope that you, too, can finally walk through your uncluttered life, breathing deep and free.

Thank you for reading, friends…may you spend each of your days breathing deep and free.  Namaste.

-Tom

As much as I might love it, the life of a freelancer isn’t always what it’s cracked up to be.  There’s a trade-off that happens when you leave the traditional workforce, the same trade-off that occurs anytime we leave a place of perceived security in pursuit of more freedom.

The price of freedom is that nobody can hold your hand anymore.  When you work for a company, your employer handles all your pertinent government expenses.  But when you work for yourself,  you automatically owe about 30% of your income to the government: 15% for income tax and 15% for self-employment tax(the independent equivalent of social security.)  And that doesn’t even begin to touch on the money that needs to be put aside for retirement or emergencies, which could take anywhere from another 5% to 25%.

For someone who’d been occupationally spoon-fed his entire life, managing my own income was an incredibly daunting task at first.

In looking back, though, I’m glad that nobody warned me.  If I had known about it, I might have hesitated and ended up being far less happy than I am now.

Once I found out what being an independent contractor was all about, I was determined to make the lifestyle work for me.  I had to.  I couldn’t go back to the daily grind, not after I’d had my first sweet taste of freedom.  I was making my stand: liberty or death.  But I had overlooked a couple of crucial weaknesses: my organizational system was crap and I had given carte blanche to my buying impulses.

I had no retirement fund.  I had no emergency fund.  I was constantly coming home with new gadgets or video games that I didn’t need.  And many of these were still laying around my room unopened, because I was so busy making the money to buy them that I wasn’t making the time to play with them.

I was floundering.  Bad.  I had to find a way to stop the impulse buys and put my finances in order.

Then, one fateful day, while I was getting this blog up and running, my girlfriend leaned over my shoulder and said, “I’m pregnant.”  I almost choked on my water and passed out.  It turns out she was kidding.  She just wanted to point out that if she were serious – knock on wood – we’d be up a creek without a paddle.  “What would you do if you found out I was pregnant?” she said.  So that was the day I picked up a copy of David Allen’s Getting Things Done and came up with the idea for the F.B.E.(Fictional Baby Experiment.)

The main idea behind the FBE was that I would pretend that there was a child on the way, a child that I needed to be ready for.  I would implement the experiment for 9 months – partly because it was funny, and partly because there were about 9 months left in the fiscal year.  So I set aside 55-60% of all my income(I based it on the average percentage of child support taken out of paychecks), and established that as an “untouchable” account, because it was “for the baby.”

That fund was then further split into three accounts: “baby food”(tax account), “the college fund”(retirement account), and “diapers”(emergency account…in case any crap were to show up.)  Anything else I had, had to be stretched out and made to last.  This was particularly difficult in the early months, considering how scarce paying gigs were at the time, but it ended up being completely worth it.

I ended up selling all of my unopened games and toys(with many a whimper, I assure you), both to help generate income and to un-clutter some space that I would need “for the baby.”  As a result, I was incredibly prepared when tax time came around and I ended up with a far better benefits program than any of my previous employers had ever offered(yes, even the government of Guam.) After the booming success of the first trial run, my girlfriend and I have decided to have another “baby”, and it’s already in its second trimester, keeping me honest and my spending under control.

So if you’ve got an active imagination, you don’t like overly formal systems,  and you’re finding yourself at odds with your personal finances…maybe you should give this experiment a try.  You might be pleasantly surprised at the results.

Thanks for reading, everyone.  I hope that you continue to grow, learn, and share with each other.  I’ll be back in a couple of days.  Have a great weekend!…:)

Edit – 10/9/10: This article has recently been mentioned in an article by Brad Tuttle over at Time Magazine’s money blog.  I highly suggest you check it out, for further money-saving ideas and inspiration.