Making Progress Towards Your Goals & Dreams Quarter by Quarter

I’m writing this in September so I’m about three or four months ahead of the barrage of content that typically shows up in early January around “New Year! New You!” 

To be clear, I am not suggesting we ignore annual planning or planning of any kind for that matter. (They probably wouldn’t let me work here if I was anti-planning.) But the concept of new-year-new-you idea of planning brings to mind two ideas I’d like to challenge: 

1. It suggests that planning has to be done on specific days or times of year so if we miss the perfect window we push things off until the next “perfect time.”

2. Often this well-intentioned type of content promotes setting intentions which are important, but which are not real plans. An intention without a plan is just a wish. 

With regard to #1, perhaps we can all just agree that planning should be able to be done at any time of year, on any day of the week? Having a plan in the first place is more valuable than waiting until some next arbitrary window of time, like the new year, opens up and suggests you make one. 

Assuming we’re aligned on that, I’ll move on to #2. 

I want you to dream big, lofty, ambitious dreams. I want you to aim beyond what you think might be possible. And I also want you to not just to hit those goals, and achieve the dreams you had in mind, but do so in such a way that you still feel as much energy at the end of that year as you had at the start. 

When we see a full year stretching out in front of us it can be easy to get caught up in #ICanDoAllTheThings energy. A year feels like plenty of time, so we often overestimate what we can get done (forgetting all the other things that might also happen in that time frame) and then beat ourselves up for our inability to deliver. 

It can be really difficult to connect the dots from what you want to have achieved a year from now with what is on your list today. And without a realistic plan we can push past our own limits only to drag ourselves limping across the finish line — that is, if we don’t give up entirely. 

I’d like you to avoid either scenario. 

Getting Clear on the Steps to Take 

If you’ve been around PF for any amount of time, you’ve likely heard about the five project rule: No More Than Five Active Projects Per Timescale. 

Most people focus on the “five projects” idea (it is the name of the rule after all) but it’s that last part, “per timescale,” that is often instrumental in getting us from stuck to unstuck with a project. And it’s also what can take us from the intention — what we’d like to do — to a realistic plan that moves us into action.

Timescales are simply different chunks of time (think: day, week, month, etc) in which we can get stuff done. I’ve taken to referring to them as time horizons because they represent how far out you are looking. 

Whatever you prefer to call them, what they provide in the planning process is clarity:

when you need clarity of purpose, shift up;

when you need clarity of action steps, shift down.

Going back to our big ambitious yearly goals, if we can shift down and consider what steps need to be taken over the next three months then we’ll have the start of a roadmap that can direct us on how to get where we want to go. 

It’s at that quarter-sized level of project where you can make substantive changes.

For many people, the quarter is the time horizon just beyond what you can easily wrap your mind around — it’s large enough to feel ambitious but small enough where you can picture the broad strokes of the plan. 

Where the year might be a horizon too far out to see, a week or even a month might feel too close in, like you’ve done a bunch of stuff that doesn’t tie together. If your yearly goal is your destination, then just looking at the weeks or months is akin to wandering down random streets and highways without a GPS. You’ll be moving, but you may not be moving in the direction you want to go. 

Creating a 12-week Roadmap

Imagine having a quarterly plan that was strategic enough to make sure you’re focusing on what matters most, concrete enough to guide your months and weeks, and flexible enough to not be obsolete before you finished it.

If you attended any of the Momentum Days we ran from 2020-2022, you’ll recognize where I’m going with this. Creating a 12-week roadmap for a single quarter-size project was the final step of those full-day immersions. At the end of those seven hours, attendees left not only having identified the “best-work” project they’d focus on for the following three months, but had mapped out the actions they’d take to get them across that finish line. 

Our Momentum Day events helped attendees get clear on what was important to them, open up to possibilities they might not have seen before, and get real about what was feasible and realistic to accomplish in three months, so they could take action and build momentum toward their dreams. 

Here’s how you can create your own 12-week roadmap:  

Step 1: Start Your Chunk List. Define the chunks of work that make up your project. 

Step 2: Sort and Link Your Chunks. Join chunks together so that they hang together. 

Step 3: Sequence Your Chunks. Arrange chunks in the order that they need to be done. 

Step 4: Clump Your Chunks. Organize smaller chunks by the larger chunks that contain them. (If chunking was breaking the building blocks apart, clumping is now putting those pieces together into larger linked units, which helps you see the higher-level time perspective.)

Step 5: Upgrade Your Clumps. Consider how much time it will really take to do these activities and as needed upgrade the timescale for your clumps (or your project as a whole).

Step 6: Overlay Your Chunks on a Timeline. Check that the sequence of chunks still appears coherent and logical. (Our 12-Week Roadmap Worksheet is a great tool for this.) 

Step 7: Schedule Your Chunks. Commit to your project by putting your chunks on your schedule. (Try not to schedule too far in advance, as you’ll likely get frustrated when reality doesn’t look like your plans.)

You can find more about this roadmapping process, along with other helpful frameworks and resources to help you with your quarterly planning, in the Start Finishing Field Guide.

Where Big Hearts, Big Dreams, and Big Results Meet

Over the years we hosted nine Momentum Days and saw people plan out projects that would significantly impact their businesses, their organizations, and their lives. 

The challenge (for us and many of our attendees) was that the plan, while only the beginning of a journey, was the ending point for our work together. 

To continue the work at a deeper and more sustained level we moved the core foundations, and best parts of the Momentum Day experience into the Academy. 

While Momentum Days were always included in membership to the Academy, our private community of motivated professionals looking to thrive in their work, teams, businesses, and lives — MDs used to be an added benefit as opposed to a feature and focus of the larger experience. At the start of 2023 we decided to build the content, coaching, and curriculum around the quarterly planning process versus having it tacked on.

As a coach in the Academy it’s been incredibly satisfying to be able to be a part of the journey and see the continued progress of our members quarter-over-quarter; but the true magic has been in very real and tangible results our members are seeing because of it.

At the end of each quarter we now host two Quarterly Planning sessions and we always start them the same way, with celebrations. There are multiple reasons to start with a celebration, but the main one is that by stopping to reflect on the quarter that was, we can see how the actions of those days, weeks, and months came together to form something greater than the sum of its parts.  

Here are just a few examples of the wins we’ve celebrated with our members this year:

• We identified where our cash flow issues were coming from, which helped us figure out what needed to be prioritized and what needed to be pushed off. We were able to build a scaffolding that wasn’t there before to support what’s coming next.

• I used Q1 as a fallow period (a “slowbatical”), and it opened up space for work I’d been wanting to do for a long time. I ended up launching on Substack (something I’ve wanted to do for years), and I had two pieces accepted for an art show. Things are growing in fallow soil. I think they just needed the space.

• I sold out not one but two retreats — something I tried as an experiment last year is now a core of my business model.

• I led a webinar for over 600 attendees. It was so fun, we could have stayed there all day in Q&A!

• Because of the work my team did (work I couldn’t have done on my own) we’re seeing more and more people share their stories online and gained a thousand new followers in the last quarter!

Revamped & Elaborated Roadmaps Inside the Academy

In the Academy we’ve been able to build upon the solid foundations set during Momentum Day to create something even better. I’ll start first with what remains and these appropriately align with the starting points we’d begin each Momentum Day with:

• You belong here. We’re all here for one main reason — to do what we call “best work,” that thing that we are uniquely called to do.

• You are already more than enough. In the Academy (and all of PF for that matter) we invite you to come as you are — there is no need to feel like you need to be anyone other than who you are. It’s why we often refer to our sessions in the Academy as “adult study hall” because we’re all here learning, growing, and figuring it out together. 

• You matter; your work matters. Only you can do the work you do in the way you do it. Your best work serves you, serves those around you, and often has a ripple into the broader world that we may or may not see. 

• You are in great company; you are great company. Our members may come from diverse backgrounds and fields but all bring with them big hearts, lots of smarts, and a penchant for changing the world through #GoodTrouble. 

• The past need not be your future. We’ve all had setbacks and challenges along the way but we look at the past not as an indicator of what will be but rather as something we can learn to help unlock what can be . 

So how have we improved upon the experience? Earlier I shared how we’ve restructured the experience in the Academy around our quarterly planning process. Here are four main ways we’ve improved upon the Momentum Day experience in the Academy:

• Sustained progress, continued support. Momentum Days required an intense focus for a full day but were limited to just that, a day together. But in the Academy we’re able to extend our support throughout the quarter (and year) via our weekly events like Office Hours and workshops designed to help you take aligned action towards your goals. 

• A built-in success pack. While we came together in community on Momentum Day it often felt like an individual activity. In the Academy you’re working alongside your fellow members encouraging, supporting, and holding one another accountable throughout the journey. 

• No more confusing the project with the result. The biggest and probably the most impactful change we’ve made is a shift to using a version of the OKR (Objectives & Key Results) framework — or as we refer to it, OKPs (Objectives, Key Results, & Projects). Our members set their sights on where they want to go (objective), identify the route markers they’ll look for to make sure they're heading in the right direction (key results), and then determine what vehicle will get them there (projects). This new approach has helped our members stay on track to reach their goals without getting target-locked on the how. 

• You have many dreams and they all matter. Because of time constraints during Momentum Days we would have attendees focus on just one project to plan out during the day. But because in the Academy we can continue the conversation all year long, we encourage members to use the two-hour Quarterly Planning sessions to name three objectives each with three key results for the quarter. This three-by-three approach serves two purposes: 1) It allows members to think about different aspects of their lives or businesses they want to move forward  and 2) Looking at a more encompassing vision for the quarter ahead often reveals constraints that allow them to set their sites on a point on the horizon that’s neither overly-ambitious nor so easy they’ll have no motivation to get started.

Driven By What’s Possible

If you’ve here and reading this (thank you!) then chances are that you too are someone who dreams big, sees what can be, and is driven to bring what is possible to life. If that’s the case, hi friend! 

As I shared at the start, I'm writing this in September, which means we’re gearing up for our next set of Quarterly Planning sessions at the end of this month — and which makes now a great time to join the Academy.  

At the end of each quarter we facilitate two of these two-hour sessions — one focused on planning for teams and the other focused on entrepreneurial and creative endeavors. Members can choose to join one or both sessions, and many choose to attend both, because life is multifaceted after all!

Then in October we’ll kick off the quarter with Office Hours, where members can ask any and all questions, including how to refine or streamline their OKRs, how to gain alignment with their team (whatever team means for them), or how to pick or plot out a project to help them reach those OKRs. 

And if you happen to be reading this sometime in the future, then it’s still a great time to join! Because going back to the very first point in this post — there is no “right” time to start planning. Our open enrollment means you can join at any time and the library of resources we offer to members means you can start your quarterly planning at any point of the year. 

So what do you say? Want to find out if the Academy is the right place for you? Fill out this short form and book your discovery call today!

And if you want to read more about the community, resources, and all the benefits of being a member of the Academy you can find out more here.