TLDR: Set goals, but don’t be rigid and inflexible about them. Be honest with yourself to ensure that you’re spending time on what you actually care about. Be intentional about the relationship between your goals your actions. Template tracking doc

I spent a lot of my childhood making fun of my parents and spend a lot of my adult life wondering why I didn’t listen to my parents sooner. There are countless examples of this: staying hydrated, putting things in their place, distinguishing hunger from boredom, etc. but one that I want to talk about today is about setting an intention and making plans. Every year at New Years, Pops would ask us what our New Year Resolutions were and I’d just roll my eyes like dude I barely know what I want to do next week, let alone over the whole year, let’s just take it day by day. Little did I know at the time how helpful this advice was.

One of my all time favorite quotes is by Dwight Eisenhower: “Plans are worthless, but planning is everything.” There’s also a slightly less relevant, but more entertaining, Mike Tyson take on this: “Everybody has a plan until they get punched in the mouth.” Let’s split the two parts of this: the importance of planning and when not to follow a plan.

The Importance of Planning

I’ve always been a planner when it comes to work. This helps to proactively identify roadblocks and bottlenecks before they come up, understand the scope and complexity of a project, and communicate clearly about expectations to make sure everyone’s on the same page. Once I stepped into a leadership role, this was even more important because I needed to make plans for each individual I supported across different time horizons: what’s their plan for the week, what are their expectations for the half, how are they progressing in their career. I also needed to do this for the team so we can communicate with leadership and other teams we work with: what’s our roadmap for the half, what’s our strategy for the year, what’s the north star vision of the team. Lastly, I needed to do this for myself (anyone who says they don’t need to set individual goals because their only goals are the team’s goals is, in my humble opinion, a clown).

I only really started doing the same in my personal life over the past year and I’m amazed at why I didn’t start earlier. Actually setting goals was such an interesting process because my first draft was super idealistic, unmeasurable, and poorly prioritized. What especially stood out was that my goals were so different from what I actually spent my time on. This was striking. I believe that someone should be able to infer what matters to you based on what you spend your time on (and vice versa: someone should be able to infer how you spend your time based on what matters to you). For example, I set a goal to improve my French, but I wasn’t actually spending any time on Duolingo. I wanted to run 365km, but I wasn’t actually running at all.

Lesson #1: Break them down. The first thing I did was to take my yearly goals and break them down into daily/weekly expectations and putting those on my calendar. I didn’t always follow those obviously (as evidenced by my still very mediocre French), but it was still helpful to have a reminder of what my goal was.

Lesson #2: Ruthlessly prioritize. Prioritizing is always a bit uncomfortable because we like to tell ourselves that everything is the top priority, but that’s a recipe to get nothing done. We have limited time so we constantly need to make tradeoffs and effective prioritization is the best way to make principled decisions about what takes precedence over something else.

Lesson #3: Balance action and outcome goals. This is a difference between my work goals and my personal goals. My work goals are entirely outcome based: it doesn’t matter what I need to do to ship a project, my goal is to get it done. My approach to personal goal setting is pretty different, I have a balance of goals about what I want to do and goals about what I want the result to be. For example, I set a running goal (action) and a weight loss goal (outcome). These are meaningfully distinct though because one can easily imagine someone who runs 1km/day but also eats donuts for every meal. A lot of times, we do all the right things to hit a goal, but our understanding of how action maps to outcomes is faulty and that’s a worthwhile lesson, but not necessarily a failure (vs in work, this is generally a failure).

Lesson #4: Measurability matters, but don’t game the metrics. Humans are lazy creatures, or at least I’m a lazy creature and maybe I’m just generalizing, but we’ll often optimize for the metrics instead of the actual goal. This is why it’s so important that what we’re measuring is actually what we care about and not just some easy proxy that’s unimportant. If my goal is to work out 300 days a year, this doesn’t actually do anything if I do 5 push ups and then call it wraps. Measure What Matters by Jon Doerr is a really good book on this and informs a lot of my opinions here. Here’s a quick TLDR.

Lesson #5: Be kind to yourself. It’s really easy to be hard on yourself when you don’t actually hit your goals, but it’s important to be compassionate to yourself when that happens. First, if you’re hitting all your goals, you’re not setting ambitious enough goals, so falling short on a couple is entirely expected. Second, this is inevitable and healthy consequence of effective prioritization so nothing to feel bad about. It’s important to use this as a lesson and a motivator instead of a reason to feel bad about yourself. For example, if I feel guilty about eating something unhealthy, I’m way more likely to eat something unhealthy again, but if I’m kind/compassionate to myself, I’m more effective at course correcting quickly.

When Not to Follow the Plan

As you acquire new information, you should constantly be updating your goals. This is a bit of a trivial example, but my salsa dancing goal was obviously not a goal that I hit in 2020. This is a tricky one to balance because on one hand we want to actually follow through on goals instead of constantly adjusting and resetting, but we also don’t want to get stuck in goals that aren’t actually representative of what we care about.

Imagine a world where over the course of the year you learned absolutely nothing about what matters to you. We all agree that’s probably a pretty shitty year. Now imagine the world where you learn a ton about yourself, but don’t actually act on any of that. I think this is what a lot of people do – they overfit to their initial goals even after they learn that those were the wrong goals.

This applies to every part of the goal setting process too. When I hit my weight loss goal for the year, I didn’t sit back and call it complete, I adjusted the target so I continued progressing towards my longer term goal. When I realized that journaling helped me organize my thoughts, I increased the priority of it and lowered the priority of something else. When I was feeling a bit down from not being able to spend time with friends and loved one, I added a goal as a forcing function for me to actually invest in relationships that matter to me. When I realized how much joy plants brought me, I added a goal around gardening.

Tracking My Goals

I find a weekly cadence here to be pretty helpful and I do my goals tracking and journaling together because they’re usually covering some similar topics. The obvious thing to do is to actually check how you’re progressing on the goals and that’s important, but also this is a good opportunity to sanity check that your goals are the right one. Are my goals too aggressive or too conservative? Are they correctly prioritized? Am I actually measuring the right things?

This is also a good forcing function to look at how you actually spent the last week and see if you’re creating enough space to focus on what matters to you. If you’re working 100 hours in a week, make sure that you actually value your career over everything else that you’re missing out on. On the flip side, if you’re playing Fortnite instead of paying attention in your Zoom classes 👀, make sure that you actually care more about your success in that video game than you do about your education.

Here’s a dummy template of my goals tracking doc if you want to copy this for yourself. Feel free to tweak it and let me know if it’s helpful for you!

Without getting into unnecessary levels of detail, my actual goals this past year focused on simplifying my life, health, mindfulness/resilience, learning, career growth, and miscellaneous adulting (not being able to cook is not a winning strategy during a pandemic). Holla at me if you want me to go in more detail, I’m happy to chat.

Caveat: Privilege

It was really easy for me to set goals in 2020 because I had a stable job, financial security, and was in good health. Obviously this would have been much harder if I wasn’t as incredibly privileged as I am. Any conversation about productivity this year would be incomplete without acknowledging how much of a factor that has to play. My intent in writing this post is not to rub this in someone’s face or to imply that folks who weren’t able to hit their goals should feel bad so I genuinely apologize if that’s how this comes across