"...how out of shape are you?!"
I'll tell you: this is clearly the worst shape in which I have ever been.
Growing up, my sister and I were always playing sports. Starting at the ripe old age of four, I dove head first into the AYSO soccer league. When that season was over, I played tee-ball. After a couple years, I added basketball to that list. There really wasn't a season in which I was idle between the ages of four and 20. I have this distinct memory of thinking "Man, I'm chubby", as a result of a little patch of flesh about the size of a roll of dimes, forming just above my belt.
Back then, I was invincible. I could eat garbage any time of day, and any number of times per day, and incur zero impact. Then I graduated high school and went straight into collegiate Track and Field. Such an activity prevented me from ending up like many of my high school teammates and friends....for a while, anyway. Unfortunately, once high school stopped, so did the athletic endeavors, for most of them.
After I completed my Track and Field stint, I so desperately wanted to avoid becoming one of those guys with an endless supply of "I used to be able to..." stories. I made sure to fit in a couple hours'-worth of fitness every single day. That lasted about 10 months and I was in decent shape. Though, as what seems to be the new "story of my life", something got in the way.
In this case, it was school. When school tightens the screws, a good student has no choice but to make it a priority. Lucky for me, I was still young enough to recover quickly. About a month later, I forced myself to get back on the proverbial horse. That's when the real cycle began.
It wasn't long before I was experiencing a one-year period. Six months of being in great shape, then 6 months of slowly falling out of shape. Followed sorely by six months of being in decent shape, then six months of falling further out of shape. Over time, the "in shape" cycle was on par with the "out-of-shape" cycle, and the previous "out-of-shape" cycle was toeing the "fat and lazy" line.
Then finally, in the Spring of 2012, I managed to affect dramatic change. Somehow, I broke free of the declination and whipped myself into pretty darn good shape.

(that's me, about a month before the height of that fitness stint)
I was back at a point where I could eat garbage, any time and the weight just kept falling off. Then I got a girlfriend. By no means am I blaming her, but I once heard the term "Boyfriend 15" (a twist of "Freshman 15", for new college students) and I quickly adopted it. Still a student, I had to quickly re-budget my time. Of course, I'm not going to cut the girlfriend out nor am I going to cut school or work out.... So, I dropped the fitness.
Within six months (no surprise there), I was way out of shape. As usual, it got to the point where I decreed (for the thousandth time) that I was going to "get back into shape!" I found a way to make my fitness work, between my classes, my girlfriend's classes, and our respective jobs. It went so well, she once told me she could tell I was losing weight because she "could get [her] arms around [me] again". Despite it being a compliment, what she said landed pretty hard.
That was right around the middle of April, and (again, as usual) I declared that I would continue on the path I had maintained for the past couple months and just coast, once I got to where I wanted to be. As predicted, Final Exams began shortly thereafter and I had a vacation planned for right after school so I stopped...again. I was fortunate enough to have a Summer Vacation after I graduated and still land a job. The summer was sufficiently lacking in physical activity beyond hours upon hours of Halo.
Sometime around the middle of July, I started going to the gym again (LA Fitness, by this point). I was hitting it five days a week - and really feeling it. But on August 1st, I started my new job - my first-ever "9-to-5 gig". I was dead set on not letting that get in the way of my fitness. Every day after work, I would grit my teeth and drive to the gym. That lasted a cool 5 weeks, before I no longer could muster up the energy or motivation to make that trip. "Eh, I'll skip today..." turned into "A few missed days won't matter".
Before I knew it, I was convinced that "next month, I'll get back into it". By that time, it was Christmas and not only did I put on the usual holiday weight, but I had added the new batch of flesh that resulted from never having been so inactive.
I did what every other American did - I resolved to stop being fat and out of shape. Four days into my new resolution-based fitness, I contracted shingles - on my face.

Needless to say, that took me out of the game for a while. And thanks to my most-extreme inactivity, I just piled on the pounds. When Lent came around, I gave up the most destructive things about my lifestyle; most notably eating out and poor sleep habits. I also vowed to work out every single day between Ash Wednesday and Easter. I was able to maintain that, without any exceptions. But I didn't see the gains I was expecting. I lost a little bit of weight but I was still extremely chunky (to my own eyes, anyway).
That was just a few months ago and since then, it's been a series of seemingly endless false starts. I kept trying to go to sleep at a decent-yet-early time so I could wake easily at 6:45AM and make it to the gym before work. No matter how hard I tried, I couldn't seem to make that stick.
The aforementioned girlfriend and I are no longer together, but we still talk on at least a weekly basis. She's a dear friend of mine and she wants nothing but the best for me. A few months back, she offered up the advice: "[If you're results-driven, you won't get anywhere. You need to find a way to enjoy the process.]" Her words have been bouncing around in my mind every day, since she offered them up - and ever since then, I've been trying to find that golden zone in which the process that will get me into shape will also be one which I will thoroughly enjoy.
I'll continue to experiment with such things but I'm writing this to highlight the fact that I think I may have found it.
It's quite simple. Wake up at around 8:00AM, get on my bike and ride to work. That's a good 25-minute ride up a not-insignificant hill. Do my 9-to-5 thing (and yes, there's a shower at work) then bike home. On Tuesdays and Thursdays, I'll include a 1.5-mile run at lunchtime. I tried that run yesterday and ho-ly-crap. I. Am. Out. Of. Shape. I could only make it about 150 yards before I had to walk and today, I am extremely sore. That has never happened to me, after running. Before today, I only ever experienced soreness as a result of weight lifting.
This newfound degree of anti-fitness is a real wake-up call. And I know I've said this countless times in the past, but.... I absolutely will affect change. Unfortunately, it's so bad that affecting any kind of real change will be a months-long, and slow going process. But I will certainly keep you up to date on how that's going.
In the meantime, wish me luck.