Last November, I attended a seminar presented by HabitStack founder Scott Ward in which he explained the difference between two types of work. According to Scott, work that is urgent has a deadline and a perceived risk of loss, whereas transformative work has the potential to permanently raise the business to a new level. Neither urgent nor transformative work is necessarily more important than the other. However, for a variety of sociological and biological reasons we have a natural propensity for favouring work which is urgent.

Scott argues that trying to circumvent our natural bias towards urgent work in favour of transformative work is a lost cause. The mental energy and discipline required to consciously choose transformative over urgent work is too high of a toll for our lizard brains. As such, the solution to the problem of how to focus on transformative work is to make it urgent.

Yearly Goals

This past January, I did something I had never done before: I set goals for what I want to achieve professionally by the end of the year. They are:

• Reach $300,000 in design revenue at Brewhouse
• Add 1 product designer to our team
• Attend 1 leadership conference
• Attend 1 design conference

I set these goals because they all speak to what I hope to accomplish here at Brewhouse: to build the city’s best product design team. To do this, I need to continue growing as a leader and set goals to grow and improve the team.

I set this year’s revenue goal based on what we were able to achieve last year — $121,500 in design revenue from May to December 2015 which, extrapolated for the time I wasn’t here, works out to $182,250/yr. Because our design team doubled part way through the year, our capacity to generate revenue through design doubled as well. Therefore, $300k in design revenue for a year is absolutely an achievable goal. This goal also sets us up to achieve my second goal of adding another product designer to the team. $300k will pay for 2 salaries for the first two or three quarters as we build our nest egg.

The latter two goals are geared more toward my own professional development, in the hopes that by improving my knowledge and understanding of both design and leadership, I’ll be better positioned to achieve the primary goals.

Of course, setting goals for the year doesn’t solve the problem of turning transformative work into urgent work, and that’s where goal-chaining comes into play.

Breaking it Down

During the seminar, Scott recommended setting quarterly and monthly goals which together form the habits that will help us achieve our yearly goals. This is where I believe I fell short.

For Q1, I set the following quarterly goals:

• 19 design iterations
• 2 design sprints
• Research conferences for Q2–Q4

And the following monthly goals:

• Meet with 1 less experienced designer in the community
• Meet with 1 more experienced designer in the community
• Write and publish 1 blog post to brewhouse.io

As you can see from the following screenshot, I did not do very well at following through with my quarterly and monthly goals:

See all of those red lines? Those are goals I failed to achieve. That’s right, I missed almost every single one. I believe there are two key reasons why this is:

1. The connections I drew between my monthly, quarterly, and yearly goals were tenuous at best. Some yearly goals aren’t represented at all in any of these lists.
2. In an effort to set appropriate expectations, I believe I failed to set enough goals to ensure I gained and maintained momentum.

Because there were so few monthly goals, I found I wasn’t checking in on my Trello board as often as I should have. Because I wasn’t engaging with the list of goals, I wasn’t considering them to be urgent.

Now What?

The first question I asked myself when planning for Q2 was whether or not I needed to adjust my yearly goals. Can I still reach $300k in design revenue this year? Will I be able to hire another product designer by the end of the year? Or, am I completely fucked?

After a great discussion about this with Adam Saint, I realized that I could still make this work. It would require some rethinking and refactoring of my strategy, but overall I believe I can still achieve the goals I set for myself this year. It won’t be easy, and will require more planning and discipline than I exhibited during Q1, but it is possible.

To start, I’ve added more monthly goals. “More monthly goals?” you ask? “But, you couldn’t even accomplish the three monthly goals you set last quarter!“ You’re right, I didn’t. However, the hope is that by adding more goals, I’ll be more diligent in checking in on my monthly progress and thus more engaged with what I hope to achieve. And, should I be successful in completing these new objectives, I should increase the likelihood of achieving my quarterly and yearly goals.

Also, I plan to reach out to Scott Ward as soon as I publish this post to get his feedback and also secure his coaching services to improve my goal setting process and to have someone outside of Brewhouse I can be accountable to.

And with that, I am off to write that email.

Update — Apr 7, 2016

After reading this post, Scott offered the following response:

I think your analysis is almost right. You did have too few goals, but I wouldn’t recommend adding more monthlies. To finish off the goal chains, I’d recommend adding weekly goals that contribute to your monthlies. Those short deadlines give you the urgency.

I totally understand what Scott is saying here. By setting weekly goals, you not only create an even greater sense of urgency, you also get the satisfaction of constant small wins. My friend Shawn wrote about this last year:

When we see that we are making progress — even small victories — then it strengthens our emotional and motivated state. We are happier and more motivated at work. And [therefore], we are more likely to be productive and creative.

He then asks us to consider the inverse, where we begin to feel like cogs in a machine. As much as I love working at Brewhouse, there are days where this rings true. Not all the time, thanks in large part to our constant, iterative product design and development process. But, when I’m not dedicated to a project and am spinning a lot of plates, I can sometimes feel like I’m playing a neverending game of whack-a-mole.

Scott and I plan to chat about this over coffee tomorrow; I am sure I’ll have lots more to share over the next week.

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