What are you working on?

How are you going to get it done?

When we talk about the things we want to accomplish it’s easy to get caught up in the dream, the aspiration, the shiny end product that we aspire to. But it’s much harder to come up with the plan that is going to get you there, and harder still to stick to that plan and execute on it. Most of us spend way more time thinking about the goal and not much time thinking about the journey that it will take to reach it. Without a plan we rarely make any real progress toward the things that we want to accomplish. And that means we’re left sitting and thinking about what we want to do, without taking any steps toward accomplishing it.

In Ego is the Enemy Ryan Holiday talks about how our brains are rewarded with positive feedback and feel-good chemical reactions when we think about our goals - and if we do it long enough our brains start to feel like we’ve already accomplished those things, even if we’re still sitting on square one. I know I’ve fallen into this trap many times and I’m betting you have too. This quirk of human nature means that we can practically convince ourselves we’re making progress and achieving our goals while in reality we’re sitting on the couch not getting anything done. Our ego literally gets fed through our thoughts and dreams, and if the ego is happy we’re not likely do do anything else. So how do we overcome our own limitations and actually make progress on these things we want to do? From my point of view it’s about planning and execution.

The planning phase is where you set your goals, set your framework, and imagine how things will look and feel when you accomplish the things you want to accomplish. But you can’t stop there - effective planning has to include the steps along the way. You start with the end in mind (more on that here) but you have to break those goals down into manageable pieces, and benchmarks along the way toward your final destination. The goals you set need to inspire you, they should compel you forward, and motivate you to do the work that will be required to achieve them. You should be able to reverse-engineer your end goals into chunks of work that you can accomplish - benchmarks to hit along the way toward your big exciting end goals. There are countless books, articles, and videos that can talk to you about goal setting and planning, but I find this framework works well for me:

• The big inspirational goals are on a four-year timeline. Meaning I’m projecting where I’d like to be and what I’d like to accomplish four years from now. This is far enough away that there is plenty of time to achieve these things, but not so far away that we can’t wrap our mind around it. I try and capture these goals in as much detail as possible, with a focus on the pieces that really inspire me and push me to want to accomplish them.
• From that four-year timeline I can begin to break down my goals into one-year chunks of work. I start from wherever I am right now and consider what needs to change, what needs to be built, and what I will need to develop (both personally and professionally) to achieve the goal. Putting these concepts into a yearly timeline allows me to say “I want to accomplish X, Y, and Z, but I can’t do those things until I’ve done A, B and C. So this year I’m going to tackle A, B and C, because it’s moving me closer to where I need to be.” That relieves the pressure that so many of us feel to get everything done at once, or jump to the final end goal in as few moves as possible. Thinking that you can or should do everything right now is a trap that leads to a lack of progress and a feeling of overwhelm. The reality is we can’t just leap to our end goals without building a foundation and doing the work along the way.
• Once I have a sense of what my yearly milestones are I can look at the year ahead of me and break those pieces down into quarterly goals. Again, this step means I’m taking a measured approach to my goals and making incremental progress. Having a dedicated place to capture and record these goals - big picture, yearly, etc is also an important part of this process. But there is no reason to try and find the “perfect” system. Whatever system works for you - pen and paper, digital or otherwise, choose one and stick with it. The specifics don’t matter as much as having something that you can see and refer to easily to help keep on track.
• Each quarterly goals breaks down further into monthly and weekly goals, giving me something tangible to put on my calendar and check off my list when it is done. The process of moving a task from “in progress” to “done” gives the brain that little hit of dopamine that it craves, a reward for seeing something through. And it helps keep momentum and keep me on track toward my bigger goals. This process helps me know I’m moving forward, and I can see the direct connections between the work I’m doing and the things I want to accomplish - that is absolutely priceless.

So there you have it - the basic outline of how I think about planning and execution. There is a quote from Dwight D. Eisenhower that I love that says “In preparing for battle, I have always found that plans are useless, but planning is indispensable.” I have always taken that to mean that the process of planning is far more important than the specifics of the plan - the specifics can and will change, there will be bumps in the road and detours along the way. But having a plan means we know where we’re going and how we’re going to get there. It provides direction and guidance for when things get tough. And it’s always easier to adapt a plan than try and build a new one from scratch. So starting with something is always better than the alternative.

Funnily enough I’m writing this knowing that my plan for last week didn’t happen the way I wanted it to, I didn’t publish anything new and never even really made time to write. I didn’t plan my time or my week well enough to make that happen, so I had to reflect on that and find the lesson in it. And that is another reason I really enjoy this exercise in writing - I’m sorting through all of this as best I can and hoping that it resonates with anyone out there as well. I will say that I’ve built out a plan for next week and if my execution matches up I’ll have a new post for you next Friday.

“Plan your work for today and every day. Then work your plan.” - Margaret Thatcher