How I Snuck Corporate Planning into my Family Life

I spent years in the corporate world, learning the intricacies of guiding a group of people toward common goals.

As any team leader knows, there's both an art and a science to practices like:

  • Setting goals

  • Communicating them

  • Measuring progress and identifying obstacles

  • Assigning ownership

  • Celebrating victories and learning from failures

Whether leading my team or overseeing an entire goals process as Chief of Staff, the challenge was the same year after year: identify priorities, create a path to achieve goals and maintain focus throughout the year.

Through trial and error, I found out the set of practices that worked for me.


Bringing Work Home, in a Good Way

I realized I wanted similar outcomes outside the office: clarity on vision and direction, a roadmap with trackable steps, and a way to monitor progress.

Because, without them….I was making goals at the beginning of the year and forgetting about them until New Year’s rolled around again.

So, why not apply the same tools and templates I used for team planning at home? My home team may be smaller, but the same practices and principles should work, right?

This realization led to regular "offsites" with my spouse (a sentence that often induces a chuckle or eye roll, along with a bit of curiosity).

So, without shame or hesitation - I’m happy to share my family’s operating rhythm:

Step 1: Create a Shared Big Picture Vision

We get caught up in the weeds of day-to-day life. What’s on the calendar? Who has travel coming up? Did you remember to mail that birthday card?

All these tactical questions are important but can make it hard to step back and focus on where you’re going in a year, two years, or further down the road.

So, the most important (and probably hardest to tackle) step is creating a shared big-picture vision.

Answering: where do you want to be? What matters to you?

Because this is so different from day-to-day breakfast conversation, a framework or tool helps get things going (or a bottle of champagne if you’re doing this on New Year’s like at my house).

Two practices I have used:

Write 10-things lists - start as an individual exercise. Get a sheet of blank paper and write down 10 things you want to be in the future, 10 things you want to do in the future, and 10 things you want to have in the future. Take a whole-life perspective (or narrow it to 5 or 10 years if that is easier).

Once you have your individual lists, compare.

Note where they overlap, and where they diverge. Create a common list of shared family priorities and keep your individual aspirations in view as well.

What do you want life to be like? Choose a timeframe (5 years works well for me) and paint a picture of the life you want to be leading. Ask and answer holistic questions like:

  • Where do we live?

  • What’s happening with the family?

  • How does work fit into the picture?

  • How do we spend non-work time?

  • What’s important to us (values, priorities)?

  • What do we want to avoid?

Think about the specifics - imagine waking up on a winter’s morning in the ski lodge and sipping cocoa together, heading out on your book tour, sending your freshman off to college. Put yourself in that time and place to create a crisp shared vision of the future.

One or both of these should get you to a shared vision for where you’re headed.

Step 2: Make the Future State Tangible

Like at work, vision statements and ideas about the future are fun and exciting. The next critical step is to map out how you get from point A to point B.

At work, this might mean a strategy or roadmapping session. The planning could happen at an offsite.

The key is to take into account where you want to go and make a list of tangible steps that need to happen to get you there. Bring it from a lofty vision into actionable items. Otherwise, the goal will remain just a dream.

Start making a list of all the things that have to be true for each item to come to fruition. Create this master list (you’ll prioritize it later) by documenting everything you can think of.

Questions to consider:

  • Do you need to move or buy property?

  • Do you need a career change?

  • Do you need to invest differently in learning or health?

  • Do you need to save money to reach a goal?

List all the steps needed, think broadly, and don’t shy away from challenging or big tasks.

Create milestones:

Once you have the list, put a timeframe on it (I use one year) and decide what has to happen first.

Select your short-list of actions to take this year to move you toward the vision. Keep the list manageable. Don’t set yourself up for failure by taking on too much. Pick 1-2 things at a time.

This is your list of priorities for the year. A physical reminder helps me focus (I am in favor of a big flip-chart on the wall)

Step 3: Check In Regularly

Keeping the momentum up throughout the year is the final hurdle.

To combat inertia - or the dreaded ‘I set a goal and forgot about it until the next planning period’ - plan to revisit the goals and track progress toward the priorities short-list.

At work, we have weekly team meetings or perhaps monthly business reviews.

Guess what - the same principles work at home.

Find a practice or set of rituals that works for your family - the main point is to keep focus on your goals throughout the year.

When you have the check-in conversation:

  • Discuss progress.

  • Identify barriers and create solutions.

  • When tasks are completed, add new priorities.

  • Celebrate the wins!


Structuring A Family Operating Rhythm

Similar to how I plan the year as a leader, I design a schedule and meetings for our family.

Based on the structure outlined above:

Step 1 and Step 2: These happen around the New Year. We reflect and envision the future leading up to a fresh calendar year, then create a shared vision and break it down into goals on New Year’s Eve (often spilling into New Year’s Day).

Step 3: Quarterly offsites: Every quarter, we push pause and reorient to the big picture, review goals, and discuss what needs attention. These offsites are true offsites, happening at a not-home location, making it a fun, celebratory experience with a nice dinner, a bottle of wine, and big conversations.

Step 3 (part 2): Weekly meetings: In order to manage the busy-ness of day to day life, we also have a weekly touchpoint. These are for discussing tactical business: logistics, to-do items, and task ownership.

All of these practices are built around enjoyable time together - so it feels less like work and more like bonding.

Give it a try! Below are some templates and guides to get you started.



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