On Structured Goal Setting (and Tracking)

Last Thursday, I wrote about ADHD and how it’s shaped me as a person, parent, and leader. The antidote—for me, at least—is rigorous organization. Which, luckily, comes naturally when you pair ADHD with a healthy dose of OCD.

This is the first in a three-part series on the tools I use to keep my life organized.

Part One: The EOS Family Plan (Personal V/TO)

When I was with UTees, our EOS Implementer introduced me to the Family Plan—also known as the Personal V/TO—and it stuck with me so deeply that I still use it today.

The Family Plan is a personal adaptation of the Vision/Traction Organizer (V/TO) that leadership teams use to run their businesses. The DNA is the same: it’s a framework for bringing clarity, alignment, and structure to your life.

It starts big-picture with your Core Vision, Core Focus, Passion, and Purpose. From there, it moves into long-term direction—your 10-year, 3-year, and 1-year visions and plans—before drilling down into the tactical: Rocks (90-day goals).

I’ll share how I use it in a moment, but first, a reminder: this is a tool, not a rulebook. Keep what works for you, skip what doesn’t. If it feels like too much for your current season of life, that’s okay.

I’ve even customized mine. Because I look at my Personal V/TO most days, review it every 30, and reset it every 90, I wanted it to also carry a constant “big picture” reminder. So I added the #1 regret of the dying, as captured by palliative care nurse Bronnie Ware:

“I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

My family is my compass. They’re the reason I left the traditional workforce—and the reason I keep this reminder front and center. The best way to be true to them is to be true to myself. That truth keeps me grounded, and it’s why, even in moments of uncertainty, I can find peace: my choices align with what matters most.

What Defines You?

While the lower portion of the Personal V/TO changes with the seasons of life, the Core Values and Core Focus rarely do. I make it a point to revisit these as often as possible. I even keep a challenge coin in my pocket at all times that represent the values below.

Core Values:

  • Present. Patient. Proactive.

  • Always do the right thing – Summum Bonum (the highest good).

  • Focus on what you can control, ignore what you can’t.

  • Love your fate – Amor Fati.

  • Remember that you will die – Momento Mori

Core Focus:

  • Personal: Lead a meaningful life through consistency in my most important roles: husband, father, friend.

  • Business: Help visionary owners bring structure, accountability, and execution to their leadership teams and high performers.

Next, I work through the 10-Year Picture, 3-Year Picture, and 1-Year Plan. I write them in the past tense, as if they’ve already happened, and get as detailed as possible. More on that below but it could be monetary/income goals, health and fitness, marriage milestones, dream purchase, anything. I’ll explain more below.

Rocks: Turning Vision into Action

If you’re not familiar, Rocks are how EOS keeps teams grounded in execution, not just theory.

Rocks are your 3–7 most important priorities for the next 90 days – the projects that will actually move your business (or life) forward. The name comes from Stephen Covey’s classic analogy: if you fill your jar with sand and pebbles first (all the small, urgent stuff), there’s no room for the big rocks (your real priorities). Put the rocks in first, and everything else can fit around them.

In EOS, you check in on them weekly, and at the end of the quarter, they’re either Done or Not Done. No partial credit.

For a Personal or Family V/TO, Rocks might look like:

  • Complete the kitchen renovation by June 30

  • Plan and book our summer trip

  • Run a total of 50 miles in September

While my family doesn’t necessarily ‘run’ on this, we use Cozi Calendar and TickTick (next week’s post) for that, this is my North Star. It’s great because it’s moldable and fluid, meaning you can change or delete it completely. And that’s okay! The worst thing you can do is to have ‘Run 50 Miles in September’ staring at you each day when you know you won’t complete it. Delete or re-write. Done. Likely no one will see this but you and your partner anyway.

That’s not to say we should lower our goals just to be able to call them DONE, but we should absolutely be realistic. As a parent of three, I know that even the best plans can be jostled by an injury, missed nap, or bout with the common cold. It happens.

Another example, just last night my neighbor challenged me to run, ruck, or hike 100 miles in September for Project Recover. I said yes, so I’ll add it to my sheet.

So, Where to Start?

My boss at UTees used to ask me to write our sales reports for the ‘snorkelers and scuba-divers’, so I’ll try to do that here too.

If you just want to snorkel, I’d start with Rocks. Look at the next 90 days of your life, personal, professional, or both, and write out what success would look like. Imagine it’s 90 days from now and you’re looking back and reminiscing about how you crushed it. What was true? What did you accomplish? Those are your Rocks for the next 90 days.

Write it down and tape it to your desk or mirror, or put them in your favorite to-do app, like I do. Revisit it each morning or on a weekly basis. DONE.

If you want to go all-in, here’s how I’d do it…

First, I’d get out of my usual environment and hit my favorite local coffee shop. I’d order my favorite drink, pop in my headphones (likely Two Step – Live at Wrigley) on repeat, and I’d get after it.

Research indicates that working in a coffee shop can enhance creativity. A study published in the Journal of Consumer Research found that a moderate level of ambient noise, such as that found in coffee shops, can improve creative performance.

You can start from either end, high-level or Rocks – that’s up to you. I do think starting with Rocks is beneficial because they’re real, tactical, and because it’s highly motivating to make progress on something quickly. From there, I’d reverse engineer the 1, 3, and 10 year picture. Give yourself a couple hours. Really think about it. Get as detailed as you’d like. Maybe you’ve always dreamt of wintering in Florida by the age of 50. Write it down. Working towards a promotion or a career change? Maybe you want to run a marathon or write a book or average 10k steps per day. Anything goes.

This isn’t unlike a vision board. And again, do your best to picture yourself 1, 3, or 10 years out. You’ve just accomplished the goals you’re writing today and you’re saying it out loud.

For example (this is completely made up):

“Today is my 50th birthday. My family is thriving! We are the house their friends want to be at. I’m working my dream job and have financial freedom. I work out most days and make art on the weekends. I’ve run four marathons. I’m still close with my best friends and spend as much time as I can with my aging parents. And we just purchased our dream home in Montana.”

The next part is so important: once you set your Rocks and make them SMART (specific, measurable, attainable, relevant, time-bound), take action on them within 48 hours.

If your goal is to write the first 10 chapter of your novel, write chapter one. If it’s to plan a family vacation, send a text and get input on dates. Something. Anything. Do it now. You’ll thank yourself later for the forward trajectory.

Finally, set a calendar invite or recurring to-do to revisit the Personal V/TO every 30-days and reset it every 90. I do it in late December, March, June, and September.

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