I recently submitted a guest post on a friend’s site, and he told me something I hadn’t heard in a long time: The article wasn’t good enough. It was quite a shock.

I started out (professionally) as a writer, while dabbling in web development. LifeDev grew exponentially in terms of readership and subscribers, and I found myself on places like the Digg, Delicious and Reddit homepages (back when the first two meant something), as well as other reputable news organizations. I had arrived as a writer—well, a blogger, at least—and it was a great feeling.

But as I grew my talents in design and development, my time spent writing took a nose dive. So much in the past year, in fact, that resurrecting this blog has become a top priority for 2013 (more info here).

When I started this blog, I was reading anything I could get my hands on about the writing process. As the years have gone on and I’d lost interest in the current format of the blog, my writing stagnated. I no longer needed to worry about honing my craft, but rather just pushing something out. (I’ll spare you the analogy I’m thinking of.)

It’s easy to forget how doing something on a regular basis (ie. practice) is vital to keeping your skills sharp. This is a classic case. I’d fallen to the trap of thinking writing was like riding a bike, you can always hop back on. The truth was I’d gotten rusty.

It would have been very easy for my friend to beat around the bush, fix the article himself, or make a myriad of excuses as to why he (rightly) wasn’t going to publish the article. But he gave it to me straight: The article wouldn’t cut the mustard for his site.

This was all the motivation I needed. Time to shake the rust off, to get back to the grind.

I have been given some great opportunities over the past six years. First there’s this blog, which has (somehow) grown steadily over the years, despite my best efforts to abandon it. There’s LifeRemix, a network I co-founded in 2007 that has grown incredibly without any real work on my part and which I’ve sorely neglected. Then there’s Gentlemint, which we started almost exactly a year ago, which has seen millions of people.

And yet…

And yet I’m constantly looking to start new things. (Sometimes getting into a new field or switching things up is a good thing.) This was part of the impetus for starting 6 to 30: instead of looking outward for the Next Big Thing, I’m working hard on the things I already have.

To me the most overlooked aspect of contentment has nothing to do with being satisfied with what you already have, but finding joy with what you already have. This was the real “aha!” moment earlier this year for me. I’m certainly grateful for what I’ve been given, but I hadn’t recently found joy in what I’d been given. Why was I drawn to these projects in the first place? What about them inspired me and, most importantly, what do I need to do to get back to becoming inspired again?

Thanksgiving is traditionally when people pause to gather with family and enjoy each other’s company (while stuffing ourselves with things that will ensure we pass out on the living room floor soon after). The holiday season reminds me of the things that I do have: a beautiful wife and daughter, great families, friends who I truly enjoy their company, and on and on and on.

And I consistently find joy in all of those things.

Early this past October I had the stunning realization that I was going to be 30 in a few months. Six months, to be exact. It wasn’t the number 30 that suprised me—I’ve seen that coming for a while now—but reflection of all that happened in my 20s.

And more importantly, what didn’t happen.

There were still things that I’d promised myself I’d do that never happened. I had a wife and daughter now, and my window for doing some things I’ve dreamed of doing was closing more and more every day.

So I made a list of all the things that I promised myself I’d change or do that I never got around to. I made a great big list of things that I’d hoped to have done before now, and left every single one on there. Some are large, some are small, and some are going to take six months to complete.

See the entire list here

But one thing was for sure: if I was going to be able to finish things that I hadn’t been able to do in the past 10 years, then I needed to make some massive changes to how I did things.

Working backwards

The curious thing about looking at what you want to accomplish and working backwards towards the goal is that you can easily visualize what needs to happen.

How do you tackle a pantload of goals at once? By working a little bit on each one, each day.

Previously my mode of operation has always been a) become inspired and b) work like an obsessed madman until the project is finished or abandoned (usually the latter). This has proved (over and over) to be a bad tactic. It’s not sustainable, and failure is way too easy.

So instead of just going with the ebb and flow of inspiration, I’ve decided to work backwards, with each goal in mind, and firmly schedule timelines and milestones along the way that need to happen.

What I changed to make this work

Unfortunately, when it comes to juggling many things at once, you have to be freaking organized. This, historically, has not been my strong suit. So I made an investment and ponied up for OmniFocus. This was easily the best software purchase I’ve made in a long, long time.

I also re-read David Allen’s Making It All Work. It’s fantastic, and I’d recommend it to anyone.

How the project works

I’ll be using a plan that combines many. Zig Ziglar, GTD, Scott Belsky’s Making Ideas Happen, and other advice I’ve picked up from people within LifeRemix too. If you’re wanting to see the nuts and bolts of how the process works, it’s over on the 6 to 30 project page.

Interestingly, over the years I’ve found that often unrelated goals are more linked than we believe. For example, when I feel like I’m really being smart with finances, etc, I’m also more likely to eat better and exercise more. When I run on a daily basis, I’m more likely to have better perspective on planning and overall vision for my life. I’m less reactive and more proactive. All of these goals are strangely unrelated.

So, I’ll basically just be working on some aspect of each goal, each day. I’ve been testing this for the past month, and it surprisingly works very well. Who knew that a simple, steady approach would work best?

Why this experiment excites me

This approach really excites me for a couple of reasons. One, there’s an end date in mind (April 15, 2013), and all of the goals are doable. (I’ve taken the past month to test the “do-ability” of each one.)

It also makes me more mindful about my life. I’ve noticed that as my life becomes more complicated, time speeds up. Reflection on what I do throughout the day slows it down. This project requires me to be very mindful by tracking everything that I’ve done throughout the day. That helps with the overarching theme of being more present in just about everything I do.

And lastly, I don’t know many people that have taken on such a weighty undertaking. This isn’t a good reason to tackle something, but oddly, it’s a motivator for me. (This is usually a bad sign, but I’d rather fail trying to tackle too much than not try at all.)

Today marks the first day of this undertaking, so I’ll be posting an update on December 15.

Here we go…

Maybe you’ve noticed there’s been a gap in posting frequency on LifeDev. In fact, it’s been almost a year since I’ve written anything here. It hasn’t been for lack of inspiration, being burnt out on writing, or anything of that nature.

It’s purely the fact that I was accidentally surprised by success.

Let me explain.

Gentlemint

About a year ago, my co-worker Brian and I decided to take 12 hours and build a simple but functioning idea. We had previously been working on a hairy, complicated (but awesome) concept of a web application. However, when you leave something unfinished for a couple years without any end in sight, it starts to weigh heavily on you.

So we decided to take a simple idea and crank it out, from start to finish, in 12 hours. The goal was never to have anything to show for it (at least immediately) other than a fun experience to shake things up.

The end product was the worst possible version of a website you’ve ever seen—I can say that because I designed it—but Brian and I started using it and actually liking it. We were so taken with our little project, that we kept working on it in our spare time over a couple of months, and gradually improved it to the point where other people could sign up if they wanted to. We told a couple friends, who told a few friends, and within a week were featured on sites like Mashable, TIME, Fox News, and plenty of deadwood media organizations as well. Gentlemint had somehow taken off, without a single presss release or pitch to any media organization.

We were being labeled as the “Pinterest for Men”, and thousands upon thousands of people were flocking to our website and and signing up for an account. In fact, the site was growing so fast that we had to immediately stop registrations and invite people gradually, as resources became available. In the course of a few weeks, we had people who loved us, we had people who hated us, and a crash course in media management. All from a simple site we’d built in 12 hours.

It was truly bizarre.

Fast-forward to today, and we’ve got the site running smoothly. I completely redesigned the site from the ground up, and the site is growing healthily. We managed to backfill all of those little things that you gloss over when you build a site in 12 hours, and we learned buckets. (I’ll share many of my learnings here in the future.)

What does this mean for LifeDev?

So now that Gentlemint is actually humming along without as much interaction, it means that I can do those things that I had to push aside while the craziness of Gentlemint went on. Like writing here more often. (I missed it more than I thought I would. You guys are a wonderful community.)

I’ll be redoing the branding and design LifeDev, as I feel like it’s lacking in a few ways. I’ve learned so much about how people interact with websites, and I’m excited to make LifeDev a more usable place.

I’m very excited for the future. I’ve got some exciting things to share, and exciting changes to the site coming down the pipe.

Onwards!

I play flag football on Sunday afternoons during the Fall with a group of friends, and it might be one of the most important pieces of my week. Aside from the great camaraderie, my favorite part is how tired I am after the games. Going home physically wasted at the end of the day is one of the greatest feelings, knowing I left every last bit of energy on the field.

There’s no greater feeling than going home, taking a shower afterwards and watching the dirt and grime swirl slowly down into the drain. That’s how I know I had a good, hard Sunday afternoon of football. The amount of dirt in the tub directly correlates to how satisfied I am. The dirtier the tub, the happier I am.

***

The dirt in the drain can translate to other contexts as well. I get (nearly) the same amount of satisfaction from hitting the “publish” button writing for this blog. At work it’s an “a ha!” moment well-executed. It could also be spending hours piecing a design concept together, or finishing that last line of a song’s chorus.

It’s all just like watching the dirt slowly swirl around.

At the end of the day I have to ask myself one thing: am I tired but excited about the things I learned and accomplished? Have I come home with green knees? If not, then it wasn’t a day I’m proud of.

We all need a metric that gives us a signal that we’ve had a day that we’re proud of–one that we can watch go down the drain at the end of a long day.

What’s yours?

I’ve been writing in a journal every morning, and today I realized that I’ve almost made it exactly a year with this habit. Now, this is nothing earth-shattering for many. Many people have been journaling for years. But for me, it’s big. It’s massive.

You see, I’m not very good with sticking with things. I’m generally attracted to shiny things like ideas, concepts, and exiting business ventures. Unfortunately, I’m not one to typically stick with the shiny things very long. I usually abandon them, and only after I’ve promised something. (I’m not proud of this, not one bit.)

This is why something as unsexy as writing in a journal every morning shouldn’t stick with me. It isn’t in my nature. But somehow it has become second nature to me. I’ve gotten to the point where if I don’t write in the morning, I notice it. In fact, it alters my day in a bad, bad way if I don’t.

My writing time gives me perspective on what I need to do for the day. I think about the big things I’m trying to do, and how to break them down. It’s how I distill and choose what I do later in the day. (It’s funny how that simple choice has massive ramifications.)

But here’s where it gets really interesting: This morning I realized that my journal had somewhat become a reference for my last year. Anyone who wanted to see what my life was like last year could, with one book. The birth of my daughter, a new business venture, a trip to the Caribbean, to name a few. Countless fears, countless random thoughts. It’s all there. Perhaps someday–after I’m long gone, of course–my daughter would want to read what I had been thinking and doing in 2010. (I don’t think my life is that interesting, but maybe she would.)

My journal has grown into something bigger than me, and only because I’ve been writing a little bit in it nearly every day. Now the habit is stuck: it’s snowballed into something more important, something that will continue to become harder and harder to break.

This is how the world is changed: not sweeping reform, not huge events. It’s changed in the small things we do every day.

What do you do every day?

Photo by roland

Jonathan has always found a way to push me, and he’s usually the first person I go to with ideas or advice.

In fact, it was but a few months ago that Jonathan convinced me to take a massive step in a direction that scared the living wizz out of me. The conversation went like this:

Three months later, I’ve done just that. I’ve been writing and playing every day. I’ve been learning about the magical world of home recording. I’ve been doing. And I’ll be sharing something with you all soon. (More on that later.)

Jonathan helped me realize that the one thing I’d been holding back on was the thing that I held closest. Why? I was scared of what might happen next. Writing music to me is far different from writing here. It’s intensely personal, and, well… it freaks me out that other people might hear it.

And then there’s the whole “what if I suck!?!?” internal questions. Who doesn’t ask themselves that frequently? Here’s a small sampling of fears that run through the minds of anyone who’s creating something intensely personal:

• “What if people think of me differently?”
• “What if nobody likes it?”
• “What if I’m not as good as I think I am?”
• and the biggest: “What if I’m actually successful?”

Sound like you? It sure sounds like me.

Jonathan addresses all of this in his upcoming book: Uncertainty: Turning Fear and Doubt into Fuel for Brilliance. (Be glad you’re only reading his advice; in person he gives kicks in the pants.)

Seriously though, if you’re creating stuff for a living, you need to stop what you’re doing and pre-order this baby. It’ll change everything. I’ve had the pleasure of reading it, and it is fantastic. But, more than anything, I owe Jonathan like crazy for giving me a much needed splash of cold truth to the face.

***

Some other friends have great write-ups on Uncertainty. Check ‘em out!

• Chris talks about why you should check out Jonathan’s book, plus a nifty video of Jonathan’s keynote at the WDS last summer.
• Danielle talks about how she goes out of her way to add uncertainty to her day.

My father in-law has been painting for decades. When my wife and I moved over the summer, he graciously helped us paint our new home.

I’d never really painted a room (or house) start to finish, so this was my first exposure to how much work goes into painting that doesn’t even require a paintbrush.

First, there’s sanding the wall of the previous paint, then filling cracks and holes with putty, then taping off the trim, windows and doors so there’s no running onto other surfaces. You’ll also have to wipe the dust that you created in the beginning with all of your sanding. THEN, and only then, are you ready to paint.

After commenting on how much prep work goes into painting a room, my father-in-law simply replied that most people don’t understand that painting is 90% prep work that doesn’t even require a brush.

That got me to thinking about other areas of life. I’ve come to realize that recording a demo is so much more than writing lyrics and finding melodies. I’ve spent hours reading books on recording techniques, learning how to use gear, and become familiar with recording jargon. It’s more tedious and harder than I ever thought it would be. I think it’s safe to say that 90% of the work thus far has nothing to do with music.

I think about my friends who are writing books, and all the time they spend writing book proposals, finding agents, shopping their book, editing and rewriting. Once the book is done they’ll have to spend tons of time and energy promoting their book with tours, speaking engagements, book signings and interviews.

It’s easy to romanticize the 10% of what we love. It’s easy to forget that the other 90% is the mind-numbing prep work; the sanding, the emails, the editing.

The people who really love what they do love almost everything related to the process. Or they can at least overlook some of the drudgery for getting to do what it is they absolutely love to do.

Anyway, just some thoughts to chew on. I’d love to hear your take on how you handle the prep work that comes with creating what it is you create.

If a restaurant waiting list is hours long, odds are there’s a good reason. Why else would people waste time and stand in line if the food wasn’t great?

The online version of social proof is a bit more nuanced. There are tons of ways to attract and showcase proof that people actually appreciate your stuff. And the larger the number, the better. These could be numbers of….

• likes
• stumbles
• number of comments
• votes
• +1′s
• fans
• favorites
• saves
• shares
• forwards
• subscribers
• followers
• retweets
• clips
• views
• thumbs up
• sales
• stars
• watches

All of these combine to show the visitor how great other people think your stuff is.

But here’s the kicker:

So often we worry about how we can collect these shards of social approval before starting. (I’m guilty of this probably more than anyone reading this.)

But it’s also been my firsthand experience that anything that goes viral isn’t usually planned. It’s carefully created first, and everything else falls into place. People go out of their way to show their approval if it resonates.

So let’s get started, shall we?

“Do I contradict myself?
Very well then I contradict myself,
(I am large, I contain multitudes.)”

~ Walt Whitman, “Song of Myself”

My brother’s incredible Walt Whitman tattoo.

This month marks the five year anniversary of this blog and this Walt Whitman quote is one of my favorites of all time. It explains this site and myself perfectly.

If you dug through the underbelly archives of this site, you’d see that there are some posts that are totally contradictory to what this site is about. When I started LifeDev in August of 2006, it was a productivity blog (like every other blog at the time). Then I switched to writing about creativity, and I still try to stick to that topic, but really now I just write about whatever tickles my fancy.

There is no ’5 Year Plan’ for this site, no real underlying theme and definitely no grand scheme to make pantloads of money. In fact the only thing that has remained the same around here is that I do the writing (for better or worse).

The problem with writing for five years across different topics is that at some point, you’re going to contradict yourself. I’ve done it many times here. I’ve changed–hopefully for the better–as a person and a writer over the past five years.

It’s taken me a long time to realize that the biggest benefit I get from this site isn’t money, or opportunities, or a microphone. The best part about writing here is that it’s a release for me.

I love writing in it. I have no set editorial schedule, I have no topics that I have to cover, and I stopped letting other people write here (with a few very rare exceptions). This site has helped me grow as a person more than anything, and I’m ecstatic that anyone else reads it and finds value from it.

So when someone calls me out for contradicting myself, I have to agree with them. I have contradicted myself many times.

Someone who sings the same tune every day for the rest of their life isn’t growing and learning.

Oh, and I can’t tell you how privileged I am to have the readers I do. Thank you. So here’s to five more years of flip-flopping and contradicting myself in such a way that would make Mr. Whitman proud.