Personal goal setting: The Milestone Exercise

A simple exercise for successful personal goal setting and getting clear on your life legacy.

What’s the Milestone Exercise? Grab a sheet of paper and join me for a step by step walk through your last 10 years!

Slumped over on the floor in a pile of loose lead paper. That’s where I found myself at 11 a.m. on New Year’s morning.

It’s not what you think – I didn’t need any help from alcohol to arrive at this desert of despair.

This particular New Year’s morning was a crisp clear day with frost lit-up in the windows like hand-crafted lace doilies. Waking-up bright eyed and early, I decided to start the New Year off right with personal goal setting.

Piles of Shoulds

Taking my cue from traditional goal setting, I started writing down all the personal goal setting ideas a bright, shiny new me could do…

  • I should read the newspaper every day
  • I should have a workout every day
  • I should volunteer once a month

A few sunny hours later I nearly cried staring at great goal ideas strewn across the floor. A few quick calculations demonstrated that my goals were off-the-charts impossible. I would need at least 8 days in the week, maybe more, to succeed. No wonder 80% of Americans give-up on New Year resolutions.

Traditional goal-setting sets unrealistic standards.

That’s right, I said it. Traditional goal-setting makes me feel like an ugly failure. Traditional goal-setting measures our habits and achievements by some platonic ideal of a healthy, purposeful civic leader who also spends hours every week soaking in bubble baths for a glowing skincare regimen after tutoring underprivileged children. Who is this woman?

If the thought of traditional goal-setting makes your stomach queasy, you’re in the right place.

Traditional goal-setting goes somewhat like this:

  1. Think of the areas you’re falling-up short
  2. Make resolutions to do better
  3. Assess our progress by how well we measure-up

So what if I told you there’s a different an approach – an approach that invites you bring your whole person into goal-setting. Not just an idealized version of yourself, but the person who is capable of eating half a pint of ice cream and staying in to watch Netflix when it’s beautiful outside.

What if we flipped the script on personal goal-setting and looked for goals that deeply fit with who we are?

When we align our goals with our primary sources of motivation, something magical happens. Goal-succeeding is not only rewarding but also, dare I say, fun.

More importantly, when we find the right goals, we are confident that we are spending our time and energy wisely. When we look back at the right goals, we think feel pride and confidence. The right goals deeply fit with who we are. They boldly declare our deepest beliefs to the world. They resonate deeply with our values. (Read more about values-based goal setting here and belief-based goal setting here.)

Your job as a human divinely put on this earth is to know your strengths, cultivate your skills, and use your imagination to make a difference. Only you can advocate for your strengths. You need to know your strengths at all times so you can grow them, use them, and demonstrate your fullest potential.

Before you set another goal, get clear on what makes you beam with pride.

When you get clarity on the types of achievements that have deeply mattered to you in the past, you get clarity on what will deeply matter in the future. You can actually imagine that magic eight-ball question, “Ten years from now, what will I wish I had started today?”

Inner fulfillment arises from deep respect for yourself. If you don’t know what achievements make you proudest, you’ll be driving along without a destination.

You only have to do this exercise once every ten years. It has the power to focus every decision you make.

Know where you're going

Instead of focusing on a future, perfect version of yourself, start by looking backwards. Remember where you’ve been, what obstacles you’ve overcome, key accomplishments that brought you to this place. Looking backwards shows you what really matters. Separate the endless lists of potential goals from the vital few that will make a difference. (Read more about prioritizing goals here.)

Your personal goal-setting mission, should you choose to accept it…

Write down your top 10 milestones

Step one: Brainstorm a list of your lifetime achievements from the last ten years, no matter how small. What are my greatest achievements? What obstacles have I overcome? What moments, experiences and projects have been the most life-giving? If you get stuck, making a timeline of where you’ve been helps jog your memory.

Step two: Whittle down the list by circling the 10 things you’re most proud of from the last ten years. Keep this list somewhere special. Ruminate on it. Keep is close when you feel stuck. Evaluate future decisions by asking Will this new project or goal contribute to my next list of top-10 achievements?

Purposeful goals make persistence the default option.

When I first completed the milestone exercise (part of a longer goal-setting exercise by Marie Forleo), I was dumbfounded. Complete with my mouth hanging open in shock. None of my so-called big award or achievements made the list. I wasn’t actually proud of graduating from an ivy league school or advancing into prestigious job titles. (Read more on my goal-setting post about celebrating your little victories.)

What am I proud of? Reading Anna Karenina all the way through – redeeming an otherwise depressing commute. Finding exercise routines that make me smile and laugh through the pain. Learning how to eat without getting hangry. Adopting a consistent prayer practice.

Here’s my question to you:

Now that you know on your greatest life accomplishments to-date, what goals are you inspired to say yes – or no – to going forward?

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