Now that you see the power of SMART-er milestones, how do you apply it? Map out your personalized milestone path with these steps:Your Northstar is the big dream driving you. It’s your “true north” that you’ll orient all your efforts around over many years.Sure, hitting that huge Northstar vision will be amazing. But true fulfillment comes from embracing the person you become through the pursuit. From finding the magic in the mundane, the meaning in the marathoning.Just because you’ve mapped out SMART-er milestones doesn’t mean your plan is rigid or unchangeable. You must adapt as circumstances inevitably change.

The Northstar Mindset

Consider critical objectives, skills to develop, resources required, and core activities on the way to your Northstar.Each milestone offers a chance to develop as a human being. To watch yourself accomplish feats you once found impossible. To prove your power to shape your reality with devoted effort.


That’s why embracing flexible agility is vital. Regularly assess if milestones are still the best route to your Northstar as life shifts. Your overarching vision guides which milestones you modify or replace.Milestone 1: Establish a morning workout routine 3x per week
Milestone 2: Prep healthy meals on Sundays to eat well all week
Milestone 3: Read 1 leadership book per month
Milestone 4: Have coffee with 1 senior executive per month
Milestone 5: Create a career advancement plan with manager
Milestone 6: Get a high-visibility project and crush it
Milestone 7: Run your first 5k race
Milestone 8: Apply and land that promotion!I call this perspective SMART-er milestones and it will give you a clear path forward, keep you motivated, and ultimately allow you to make consistent progress towards your “Northstar” – that guiding light of where you want to end up.

As you do, pause to appreciate the magic of putting one determined foot in front of the other. Of making the difficult doable through devoted consistency.

Imagine your Northstar is to get in incredible physical shape while also advancing to an executive position at work. Trying to do both of those things at once will be overwhelming.

What are SMART-er Milestones?

By making milestone achievement a habit, you tap into the force of compounding. Like compound interest multiplies money, milestone momentum multiplies your results. You develop the confidence and capability to set bigger milestones. Minor achievements start stacking into major leaps.

  • Specific
  • Measurable
  • Achievable
  • Relevant
  • Time-bound

While those are positive, they lack the greater sense of purpose, clarity, and alignment that SMART-er milestones provide.That’s how you create a life of ever-expanding possibility. By learning to find joy in crafting the smartest little steps that, over time, will take you to the stars.


Without measurable milestones, huge Northstar goals can start feeling discouraging, like you’re not getting anywhere after months of work. But checking off milestones provides consistent reinforcement that you ARE advancing.

  • Align with and make clear progress towards your Northstar
  • Give you a sense of purpose and direction

But a Northstar goal all by itself isn’t actionable. You can’t just say “I want to have an amazing career AND family life” and expect it to happen without a concrete plan.

  1. Build up an emergency fund of 6-months expenses (within 1 year)
  2. Negotiate a flexible schedule to work from home 2 days/wk (within 3 months)
  3. Take an online course to learn high-income skills (within 6 months)
  4. Earn a $5k side income from an enjoyable passion project (within 1 year)
  5. Max out retirement account contributions (before tax deadline)

Lay out a rough timeline from now to the ultimate Northstar destination.The Northstar is your overarching life mission or purpose. It’s the ambitious goal that you’re working towards. Things like “Become an executive while being a fantastic parent and spouse” or “Develop multiple streams of income to become financially independent” or “Be in the best shape of my life while excelling in my career.”

  1. Save some money
  2. Learn something new
  3. Earn more income
  4. Do engaging work

A timeline, calendar, or visual hierarchy all reinforce how each one feeds your purpose. Then, start hitting those milestones! Track progress so you celebrate wins and analyze when you fall short.

The Power of Purposeful Progress

Notice how each milestone is specific, measurable, has a deadline, and is realistically achievable as part of the overall process. More importantly, they all directly feed into the larger goal of financial independence/career satisfaction.Your initial milestone map represents your best thinking NOW. But new realities emerge as you make progress.

SMART-er milestones help reframe goal achievement from a burden to an adventure. They turn your biggest dreams into a step-by-step game you can win one level at a time.The true power of SMART-er milestones comes from the unstoppable momentum of small steps compounded over time. Most people overestimate what they can do in a day, but vastly underestimate what’s possible in a year of focused milestones.Compare that to vaguer, less directed milestones like:

The Added Power of Milestone Tracking

Under “Master productivity” you could set milestones like:Perhaps you get an unexpected job opportunity requiring new milestones. Or you confront a health issue, reshuffling priorities.That’s where Milestones come in. Milestones are the individual steps that, when combined, form the path to your Northstar. They break down that lofty goal into specific, achievable objectives. An important thing to note is that SMART-er milestones do NOT have to be huge, audacious goals in themselves. In fact, I’ve found focusing on concrete, achievable “small win” milestones is often the smartest way to build momentum, especially when getting started.

ADVERTISING Now let’s compare that to the typical approach of setting disconnected goals that may or may not get you closer to your ideal life situation. We’ve all wasted months or years on unfocused objectives that don’t synergistically contribute to a greater whole.I’m going to share a powerful strategy for breaking down your biggest goals into concrete, achievable steps. You’re likely already familiar with the idea of milestones – those major markers of progress towards an objective. What I’ve found is that by thinking about milestones a little differently, you can make them exponentially more effective for achieving your grandest visions and your overall life direction.

Creating Your Customized Milestone Map

What’s your huge, long-term life vision? Dream big here – no limits when identifying your Northstar purpose.

2. Brainstorm the major steps to achieve that vision.

The problem is that these huge, life-changing objectives can feel so daunting and far off that we don’t even know where to start.

3. Organize steps into a logical milestone sequence, filling in any gaps.

A final note – pursuing audacious goals is ultimately about the meaning and growth gained DURING the journey, not just reaching a finish line.The biggest benefit of SMART-er milestones is they keep you laser-focused on consistently moving towards your North Star vision. There’s no wasted effort or distractions on irrelevant tasks.

  • Master productivity/time management to “make time”
  • Advance career to a flexible, high-income level
  • Strengthen marriage with regular quality time
  • Be an involved, supportive parent as kids grow
  • Continuously grow in parenting/relationship skills
ADVERTISING For example, let’s say your Northstar is “become financially independent while doing work I love and having great work/life balance.” Some SMART-er milestones could be:Even more importantly, tracking reveals when you’re NOT hitting milestones, so you can analyze, learn, and adapt your approach proactively. Milestones give you built-in points to assess and pivot before getting too far off-course.
  • Read 3 top books on productivity in next 6 months
  • Implement a morning routine to start days intentionally within 30 days
  • Establish “9 to 5” work hours, shutting down electronics after (start Monday)
5. Map out milestones visually to see alignment to your Northstar.

By setting milestones purposely linked to your ultimate goal, you avoid the common trap of chasing arbitrary objectives that don’t add up to the life you really want. Imagine spending years advancing a career only to realize it doesn’t align with your true priorities.

Maintaining Agility Along the Way

This patient consistency of small wins, purposefully aligned, unleashes exponential progress. Each milestone builds on previous ones, accelerating growth.

Each milestone is a concrete step along the path to your Northstar vision. And as you achieve milestones, you make steady progress closer to your ultimate goal.So in addition to being specific, measurable, achievable, relevant, and time-bound, SMART-er milestones must also:

ADVERTISING Many people are familiar with the SMART criteria for setting effective goals:

The Exponential Impact of Incremental Progress

But you CAN get there one reasonably-sized milestone at a time:We all have big dreams and ambitious goals we’d love to accomplish, like getting that major promotion while still having quality family time, getting fit and healthy despite a crazy busy schedule, or saving up enough to retire early and pursue our passions.

These victories, even minor ones, provide motivational fuel as you see efforts tangibly paying off over time. It’s incredibly satisfying to look back and appreciate how far you’ve come, one step at a time.

4. Set specific, achievable milestones in each category.

With purposeful SMART-er milestones, you stay on the most direct route to success, minimizing detours and maximizing progress. You transform into what Stephen Covey calls a “meaningful specific” instead of a “wandering generality.”Say your Northstar is to have a thriving career AND deeply fulfilling family life. High-level milestone categories could include:

ADVERTISING SMART-er milestones act like a compass, providing a clear “true north” to orient all your efforts. You identify the very next milestone on the path and pour your energy into achieving that step. Then once you reach it and get a motivating boost of progress, you’re compelled to tackle the next milestone. And the next. Each one takes you closer to your Northstar.The “er” means Aligned with your Greater Purpose. It adds an extra dimension by tying each milestone back to your overall Northstar mission.You don’t need to postpone pride and fulfillment until you reach the end of the rainbow. Every milestone is its own pot of gold if you recognize it.SMART is a solid start, but I’ve found even more success by modifying it for milestones oriented around a Northstar goal. I call these SMART-er milestones.By channeling all your energy into achieving one milestone at a time, you avoid getting overwhelmed by the distance to your Northstar. You just aim at the next target. Then the next.
ADVERTISING So dream huge. Reverse engineer that Northstar into concrete steps. Then pour yourself into achieving them one at a time.Another advantage of SMART-er milestones is the built-in ability to track progress. Each milestone achieved represents a clear “win” on your way to the Northstar, whether big or small.SMART-er milestones are designed to infuse a sense of purpose, progress, and fulfillment into the process itself. Not to defer happiness until you finally achieve the Northstar.So don’t get discouraged by Northstar goals that seem out of reach right now. With a tailored milestone map and relentless commitment, you’ll be shocked by how far you travel over time.

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