Two Steps Forward, One Step Back — My 2013 Yearly Review

When we usually hear the phrase “Two steps forward, one step back,” it’s in the context of lost productivity. That is, we’re undoing some of our progress through mistakes. There’s another way of conceptualizing this phrase that’s been bouncing around in my mind the last few weeks, though. What if we the change the connotation of “one step back” from being a reverse movement in productivity to being a reflectionary distancing from the day-to-day shuffling?Two Steps Forward.jpeg

When creating something, whether it’s a blog, a piece of software, a musical composition, or your life’s path, you’re not going to move through the creation process swiftly and effortlessly. Creating something of quality requires more than moving forward — it requires reflection. And with reflection comes a refined definition of “forward.” This is the real “one step back.”

Today, I’m taking a step back. I’ve adopted David Allen’s Getting Things Done (GTD) system this year, and one of my favorite components of this system is the weekly review. Every week, I schedule half an hour to an hour to review all of my projects, my inboxes, my Asana tasks, my Workflowy lists, my meeting notes, and my sketches and scribbles. I wrap my arms around my life’s action items, and I can sleep soundly knowing that I have everything documented and organized. I’d like to apply this review process to my life at a higher level — I’d like to perform a yearly review.

I’ve been plowing forward a lot this year. It feels like I’ve taken about a hundred steps forward since I last took one of these steps back for reflection. I think the last time I really reflected on the big picture stuff in my life was shortly after I started working. I started to feel a bit trapped and confused by the fact that, for the first time in my life, the stereotypical next step wasn’t clear. I felt like Brad Pitt in Fight Club, sitting in the tub and recounting his life’s path to Edward Norton:  “Now I’m 25, make my yearly call again.  I say ‘Dad, now what?’ He says, ‘I don’t know, get married.'”  I didn’t want to get married (still don’t), so I was stuck. Where was the next stepping stone?

I didn’t really get over that feeling, but I was able to suppress it in part due to my acquired ability to manage emotions and in part due to working and studying long hours. As I’m revisiting this conundrum, I’m a bit surprised that the emotions of fear and melancholy aren’t re-surfacing… It doesn’t seem like I’ve done anything in the last year to solve this problem — I’m seemingly further and further away from the marriage/kids/golden retriever lifestyle every year and I still don’t know how I want my career to progress — so why do I feel so calm right now?

Side note: I just glanced out the plane’s window in a reflexive search for answers, and I can see the plane’s wing wobbling. Seriously, why am I calm? How the hell is this thing in the air right now? Physics is cool.

Anyways, I’m realizing that a big part of the reason I’m not panicking about my life is that I’m getting better about embracing uncertainty. I was pretty awful at this in high school, and I grew drastically in this department by being in the Raikes School in college. On top of the shock of a new culture and living on my own, the Raikes School shook me to my core by challenging me in ways I had never been challenged. I was far from the most intelligent or knowledgeable student there, and I had just enough self-confidence and tenacity to claw my way through. Because I knew I wasn’t the smartest, I didn’t get caught up in the IQ pissing contest, and almost all of my high school arrogance was washed away. I emerged from that program not only a much more talented and confident individual, but also a better person.

In many ways, I feel as though I’ve regressed since graduating. Outside of my coding skills atrophying, I’m no longer in an environment that pushes me to be great. Allstate is a great place to work in many ways, but it doesn’t push me the way that the Raikes School did. It doesn’t throw me in over my head nearly enough, and the career progression has a beaurocratic feel to it (you get a raise at x months and get promoted at y months). However, because my environment hasn’t satiated my hunger, I’ve had to push myself. I get in early and I stay late. I dig deeper and look into more things. I strive for quality and efficiency. “Good enough” doesn’t feel good enough for me. I’m sure that at some point in my career, I’ll acquire the apathy that masquerades as wisdom and prioritization, and I’ll lose the edge from this need to get better. But I’m still a 23 year old kid, and the corporate world hasn’t beaten that out of me quite yet.

Because I’m working so feverishly, two significant, opposing forces are emerging. One is that, because I’m constantly pushing to move more things forward faster, I’m not reflecting as much. I’ve made huge progressions in project management, prioritization, organization, communication, politics, efficiency, statistical and mathematical skills, and Excel shortcuts over the last year, but these progressions have come without a master plan. There’s no Life Task or Purpose that’s driving these advancements or pointing them in the right direction. When trying to answer whether I should learn SAS or start studying for my next actuarial exam in my free time, there’s no overarching plan that can guide my decision. This is worrisome, but I have less urgency to solve this lack of Life Purpose now than I did a year ago.

The reason for this lack of urgency is rooted in an increasing comfort with uncertainty. This is one area in which I most certainly have not regressed since graduating. I’ve sensed that letting my hunger guide me will eventually translate into a crystallized sense of direction. Or at least, that theory has been circling in my mind for several years. But it wasn’t until about five months ago when I read an excerpt from Robert Greene’s Mastery about Paul Graham and the hacker model of learning and progressing that I fully invested in this approach. Greene put into words the theory that my mind had been trying to make sense of. Here is what he wrote:

“The model goes like this: You want to learn as many skills as possible, following the direction that circumstances lead you to, but only if they are related to your deepest interests. Like a hacker, you value the process of self-discovery and making things that are of the highest quality. You avoid the trap of following one set career path. You are not sure where this will all lead, but you are taking full advantage of the openness of information, all of the knowledge about skills now at our disposal. You see what kind of work suits you and what you want to avoid at all cost. You move by trial and error. This is how you pass your twenties. You are the programmer of this wide-ranging apprenticeship, within the loose constraints of your personal interests.”

“You are not wandering about because you are afraid of commitment, but because you are expanding your skill base and your possibilities. At a certain point, when you are ready to settle on something, ideas and opportunities will inevitably present themselves to you. When that happens, all of the skills you have accumulated will prove invaluable. You will be the Master at combining them in ways that are unique and suited to your individuality. You may settle on this one place or idea for several years, accumulating in the process even more sills, then move in a slightly different direction when the time is appropriate. In this new age, those who follow a rigid, singular path in their youth often find themselves in a career dead end in their forties, or overwhelmed with boredom. The wide-ranging apprenticeship of your twenties will yield the opposite — expanding possibilities as you get older.”

Nothing that I’ve read this year and no idea that I’ve encountered has affected me as profoundly as that passage. Suddenly, I’m free. I don’t need to know what my career plan is — more than that, I don’t even need to know what my next step is. I just need to focus on acquiring the skills that I’m passionate about and position myself in a manner that will maximize my opportunities to learn. A side benefit of applying this principle is that I’ve lost a great deal of the attachment to the status quo: If all I’m trying to do is learn and get better and I’m not on a rigid career path, why would I stay where I am if I can grow more elsewhere? Inertia loses its power.

I directly applied this philosophy over the last few weeks and took another position that I feel will provide me with a tremendous opportunity to learn so many of the things that I couldn’t learn in my current position. When the thought of transitioning first surfaced, inertia did its best to hold me in place: “Have you really learned all you could in your current position? You realize you’ll have to learn just about everything from scratch, right? You’ll have to start all over…” But this hacker philosophy set me free from these thoughts. And it’s set me free from the nagging fears that I’m stumbling two steps in the wrong direction. For now, I’m ok with stumbling without direction, as long as I’m stumbling towards things I love and I remember to take one step back every once in awhile…

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