The Art of Working Alone

Systems I'm using to keep myself directed and motivated in the face of unemployment

A few months ago I met someone who was on what she referred to as a “radical sabbatical”, and we bonded together over the thrill of self-direction. Until I realized that—as best I could tell—her sabbatical involved traveling the world and partying while living off her savings. It sounded like a blast, but I couldn’t help the judgment creeping in the side of my brain.

“Oh, she’s calling her thing a sabbatical but really she’s just taking a vacation. My sabbatical is going to be so much different. In my sabbatical I’ll actually learn and accomplish things.”


Accomplish what, exactly? The problem with not having anything to do is… well, that you don’t have anything to do. Or maybe more accurately you have anything to do. Anything and everything is on the table. How do you pluck a task out of the wide open space of future possibility? How do you allocate an hour in the seemingly infinite expanse of time before you? It can be a bit paralyzing.

Fortunately I have a good amount of experience getting things done from my professional days. So what I know—or at least what I believe—is that it’s the structure that’s critical. The creation of a system by which you can put in ideas, apply a sprinkle of reflection and prioritization, and pop out useful output on the other side. Having the right systems in place is like riding a train - you just have to stay on the rails and you’ll make continual progress towards your destination.

“Startup success can be engineered by following the right process, which means it can be learned, which means it can be taught.” Eric Ries, The Lean Startup

My Systems

Here are some of the systems I’m going to be trying during my six month experiment. They represent a distillation of the productivity lessons I’ve learned over the past ten years applied to my current situation and goals.

  1. Set and achieve goals constantly
  2. Log time relentlessly
  3. Ship something every week
  4. Retrospect regularly
  5. Write publicly and regularly
  6. Make time for learning (but not too much)

I’ll say a bit about each of these below.

Constant Goal-setting

I decided that my primary unit of work would be a week, so I’m using weekly goals, set every Monday, to try and keep myself on track. I’m also using daily goals - set first thing in the morning before I do anything else - to try and direct each day.

I keep my goals in a simple Google doc. My weekly goals sit on the top of the doc, and my daily goals go right below them. Here’s what it looks like:

Goals as of April 6

Yes, I’m playing with something MailChimp related

With this format I can see quickly how my daily goals are working towards my weekly ones and make sure I’m not getting off course. I can also easily how I’m doing on the day’s goals.

If I don’t accomplish a goal on a given day I have to manually bring it up to the next day, or decide to drop it—which I’ve found to be a useful exercise to go through each morning. I’ve built weekly goal reviews into a retrospective process I’m doing every week which I’ll talk more about in a bit.

I’ve found so far that regularly setting and thinking about goals has been useful in directing my time and keep me from going down rabbit holes.

Relentless Time Logging

I’ve long been a huge believer in tracking my time and have done it professionally for many, many years (first by policy and now by choice). I believe that diligent time logging will be key to ensuring I spend my time well - creating visibility and accountability into my schedule. Like goals, I’m building timespend review into my weekly retro process which lets me course correct or reflect when my time goes differently than I expected.

Week 2 time breakdown

How I spent time in my second week

Shipping Weekly

With something so open-ended as my sabbatical, I know there is a high risk of “analysis paralysis” - the state of over-analyzing a situation so that no decision or action is never taken.

To help overcome this I have a broader goal to ship something every week. It doesn’t have to be anything fancy - I’m currently counting polished blog posts, though that will hopefully change - the idea is just to put something out into the world on a regular basis as a forcing function to prevent churning on things until they are perfect. This fits in well with the weekly goals, which, presumably should always include shipping something.

Regular Retrospectives

Professionally I’ve always found retrospectives to be super useful and yet often observed that they are rarely done unless built into a process. Why look to the past when we can do the stuff that’s in front of us?

I already mentioned this, but I’ve decided to do weekly retrospectives to reflect on the week, see how I did with my goals, look at my timespend, and assess my overall emotional state (can’t forget about that!). Here’s an example one from my first week.

Writing Publicly

Another tactic I’m trying is writing regularly, and I have the goal of publishing everything I write. I’m doing this for a few reasons.

Writing helps clarify my own thinking

I actually started this post on the first day of my sabbatical, because I wanted to map out what the structure of my days and weeks would be like. In writing it down, I was able to solidify the process and better understand why I’m doing the things I am.

Writing publicly helps me get input and feedback

So far, just by writing about things publicly I’ve already had people reach out and 1) give me great advice, 2) give me frank feedback on my ideas (spoiler: they’re mostly bad), and 3) pitch me things.

Having this community has already helped me with one of the pitfalls I was worried about going into this: the isolation of working alone.

Just write poorly. Continue to write poorly, in public, until you can write better. I believe that everyone should write in public.” Seth Godin, Talker’s block

Writing is an interesting avenue for experimentation

Not knowing what I’ll be doing yet, I have the opportunity to test based on people’s interest (or lack thereof) what topics I can write about in an engaging way. This might help inform what type of market or audience I should target down the road.

Writing creates some accountability

Finally, I’m hoping that by writing about the sabbatical I will actually be forced to follow through on it. It would be much easier to keep quiet about what I’m doing, and then if I never accomplish anything worthwhile I can say I just took six months off. While that would be nice—and quite frankly a lot easier and less anxiety-inducing—it’s not aligned with my goals for this period of my life.

Making Time for Learning

One of my biggest goals for this period was to learn a lot and I suspect that most of the learning I have will be in the process of working on things. Everything I’ve built so far has used at least one or two technologies new to me. I’m trying to get better at front-end design. And of course I’m trying to improve my writing abilities.

However, even though I’ve always been a proponent of the learning-by-doing style, I also know that every time I take the time to actually study something I almost always find it super valuable (and usually complete the experience feeling like I should have studied that thing ages ago).

So in addition to learning through my work I’m explicitly blocking out time each week for pure learning - things like reading books and blogs, taking online courses, or watching instructional videos. For this I’m hoping to set both a minimum time (so I don’t forget to do it) and a maximum (so I don’t get so consumed by reading that I forget to produce). The current sweet spot I’m targeting is 2-5 hours a week.

Going back to the bigger picture

So having made some headway on some of the peripherals about how I’m going to work I still don’t have a clear sense how I’ll actually chose what to work on. When the “thinking and talking about how to do work” turns into the actual doing of work—how will I know that I’m doing the right thing? How can I be confident that my weekly progress is actually working towards a bigger picture?

The short answer is that I don’t really know yet. I’m mostly hoping that will fall out from working within these systems—much like these systems fell out from my first goal being “define a rough shape of my day-to-day working structure”.

I’m on the rails now so let’s see where this train is going!


If you made it this far thanks so much for reading! If you’d like to keep following along my journey you should subscribe to receive updates below.

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