Forks in the Road

January 13, 2015

Every now and then there comes a time when the momentum of what you’ve been doing has ceased and a variety of different paths open up in front of you. Those moments are chances to reflect on what you have achieved, what’s important to you and what makes you happy.

My last year was pretty eventful: objc.io kept growing, we released Deckset in April, authored a book over the summer and published it in October, and finally we started working on a new project that’s due for release soon.

A little while ago Chris and I got a financially very attractive offer to work for another company. We were tempted, but in the end we declined. Nevertheless, going through this process inspired us to take a step back, to reassess where we stand, and to make a conscious decision of how we want to move forward, instead of just coasting along.

The verdict isn’t out yet, so that’s not the topic of this article. Rather, it’s a way for me personally to lay out a framework that’s the basis for my considerations. And maybe it’s useful for you too.

For me there are two basic dimensions to a decision like this: what I’m working on, and how I’m working on it. Let’s examine the what dimension first.

The first way of looking at what I’m working on is to zoom out — taking a look at my work in the context of my life as a whole. What are my ambitions in life? Where do I want to make a difference in the world? Has my work contributed towards this?

These considerations have become more important to me recently. I could attribute this to getting older, having crossed my mid-thirties. However, I think that’s only an indirect factor by having 15+ adult years under my belt to reflect on. I’ve done quite a lot of different things in my life, and while I don’t mind the change in what I’m doing specifically, the notion of working towards a greater goal in the long run is becoming more and more appealing to me.

Often those bigger questions about finding purpose in life are tough to answer, but I think it’s worthwhile reflecting on them regularly. Otherwise it’s easy to just coast along — jumping on opportunities as they present themselves — without ever steering towards your broader goals and values, or even without thinking about these things at all. Meanwhile, the groove in which your life is progressing gets carved out bit by bit, almost imperceptible, until the cost of changing course is very high.

Once I’m comfortable with the general direction of what I’m working on, I can take a closer look at the details. It’s kind of like the branches of a tree: once you’ve decided among the thicker ones further down, all kinds of smaller branches present themselves. I usually find this the much easier part, since those decisions are more tangible and have more predictable outcomes.

With regard to how I work, there are many factors to consider, but at the end of the day it comes down to a simple question: How much freedom do I want to have? Which freedoms am I willing to give up in pursuit of a goal?

Freedom or the constraint thereof is affected by many factors: time and work place flexibility, responsibility, accountability, and overall stress, to just name a few examples. Those factors depend on many variables: whether you work for yourself or within a team, locally or remotely, with your own money or with investors' money, with or without employees, etc.

I like to look at this aspect in the broader context of what makes me happy in my life other than what I’m working on: for example spending time with my wife, having time to learn and to grow, being able to pursue new interests, and having the flexibility to adjust what I’m doing to what I feel like doing. Those are the things that fill the abstract term freedom with life.

Ideally, there would be a way to maximize satisfaction with both aspects, what I’m working on and how I’m working on it, but one can offset the other to a certain degree. If what I’m working on is really important to me, I’m willing to accept more compromises in my work structure. On the other hand, if I’m very happy with my work structure, I’m willing to make some compromises in what I’m working on.

For me there’s uncertainty involved in all these questions. However, I think that making a conscious decision each time you encounter a fork in the road, will diminish this uncertainty over time. It makes you more conscious of what you’re doing and gives you more control over your own destiny.