Making Progress Towards Your Goals & Dreams Quarter by Quarter

Consider steps needed over the next three months to get to where you want to go.

Writing this in September, 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 Projects 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.

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Get Support for Your Quarterly Planning with a Pro Subscription

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 true magic is in the very real and tangible results our members see because of these coaching sessions.

The core of what we covered in those Momentum Days of the past are now part of the Quarterly Planning sessions we offer our Productive Flourishing Pro subscribers.

When we do a Quarterly Planning session we like to start with a celebration. The main reason for that is to pause to reflect on how the quarter was, so 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:

• 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!

In addition to the Quarterly Planning sessions, PF Pro members have access to our Monthly Community Coaching Calls, which offer:

• Sustained progress, continued support. Use these monthly calls to get answers to the questions that help keep you on track, navigate around roadblocks, and improve your results.

• A built-in success pack. See what your fellow members are doing on their quarterly projects, and encourage, support, and hold one another accountable throughout your journeys. 

Going back to the very first point in this post: there is no “right” time to start planning. Your quarter can begin whenever you need it to.

Upgrade to PF Pro at any time and with your annual subscription get access to all four quarterly planning sessions for the year; all of the monthly coaching calls; instant access to our current library of planners, worksheets, tools, and courses; and all the latest offerings we’re publishing each month.