How to Set Milestones to Progress Towards Your Goal

When you define milestones for yourself, you build a ladder to your goals. The more rungs you add, the easier the climb.

Taking those steps can be challenging. But for those who haven’t done it before, the tougher challenge actually comes first: carving out the steps.

What do appropriate milestones look like, and how are they placed? Let’s start with a definition.

What Are Milestones?

According to Merriam-Webster, “milestone” has two definitions.^[1] The first is literal: a rock used as a milepost. The second, “a significant point in development,” is what most people refer to when they talk about making progress toward a goal.

“A significant point” is what you make of it—if you’re learning to cook, making eggs over easy without breaking the yolks may be significant to you. If you’re a professional chef, making eggs might not even count as a warm-up.

How do you decide what’s significant?

By looking at your larger goal.

To the professional chef, the goal might be to master the full English breakfast so it can be added to the menu. The amateur may simply want to cook himself a quick meal before work.

That’s what makes setting milestones so tricky—you need to understand your start and endpoints to know which markers to set in the middle. And on top of that, you have to plot them on a timeline, stay motivated, track your progress, and learn from your mistakes.

How to Define Milestones for Yourself

Defining milestones for yourself can be a tall order. Here are ways you can do it.

1. Define Your Endpoint

What do you actually want to accomplish? Is it securing a job in your field? Boosting your grade point average above 3.0?

Remember, goals come in many colors. They might be personal, financial, professional, social, emotional, or spiritual. There’s no “wrong” goal, just as long as you know your “why” and are committed to it.

2. Start Where You Are

To set milestones, it’s not enough to know where you want to end up—just as important is where you’re at now.

Looking at yourself objectively is tough. Think about it, and ask others for a gut check. If you’re not sure how your basketball skills stack up to people who eventually go pro, ask a trusted coach or teammate for their opinion.

3. Be ‘SMART’ About it

Once you know where you stand and where you want to be, you’re ready to plot some waypoints for yourself. Define milestones just as you do your big-picture goals—with the “SMART” system.

Milestones should be:

Specific

To be meaningful, milestones need to be carved out precisely.

If you’re trying to get fit, what does that mean to you? Would you like to lose a certain amount of weight? Build muscle? Overhaul your diet?

All of these might be milestones toward your goal.

Again, if you aren’t sure, ask a professional. When I decided to get healthy for my kids, I knew I wasn’t aiming to be an Olympian. For some “normal dude” coaching, I reached out to a friend at IVRY Fitness.

He helped me truly understand what specifically I needed to be my best self. I always tried to just jump on the Whole30 bandwagon or whatever was the hottest fitness goal at the time. He helped me understand that to achieve sustainability in your goals, they need to be targeted for you.

Measurable

To stay on track in my fitness regimen, my checkpoints had to be measurable. In some cases, this was a simple “yes or no”. One of my milestones, for example, was eating a real lunch every day.

In other cases, my milestones were numeric in nature. For the cardiovascular component, I set a daily step goal for myself. To build strength, I needed to gradually increase the amount of weight I was lifting. Making each of these measurable helped me know whether or not I’d met the milestone.

Achievable

Not all measurable and specific milestones make sense. There’s no way I was going to bench press 400 pounds the week after I set my health goals, for example. Trying to do too much too quickly would have discouraged me, not to mention the risk of injury.

For each milestone you’re considering, ask yourself: Is this a “stretch” milestone, an easy one, or a “goldilocks” one? Again, ask someone who knows you well if you’re not sure.

Relevant

Milestones have to make sense in the context of your larger goal to be worth setting. If you can’t explain how your milestone actually gets you closer to that goal, set a different one.

For example, mental health is an important part of fitness. But because I wasn’t depressed, there’s no reason I’d define a milestone for myself like “see a counselor once a week.”

Time-Bounded

When do you expect to reach your milestone? Is it an hour away? A whole year? Any time horizon is fine, so long as it’s factored into the milestone you set. Remember that milestones must be achievable.

4. Take it One at a Time

If setting a dozen milestones at once is too daunting, try setting a new milestone only after achieving the last one. If you’re learning to swim, for instance, you might decide which stroke you want to learn next depending on how difficult you found the last one.

Doesn’t that make achieving your overall goal more difficult? Not necessarily. You just need to know the general arc. With the swimming example, your plan may be to learn a new stroke every other week. The specific strokes don’t matter until it’s time to practice them.

5. Write it Down

When you set a milestone, write it down. Not only does doing so help you further define the milestone — remember the SMART system—but it also makes you more likely to achieve it.

Milestones really are goals nestled within larger goals, and research shows writing down goals makes you 42% more likely to reach them.^[2]

6. Be Flexible

Try as you might, you won’t meet every milestone you set for yourself. Don’t punish yourself. Learn from your mistake, and set another—and hopefully more achievable—milestone.

Do you need to scrap other milestones down the road because you failed to meet one? Not necessarily, but you may need to delay them.

If you didn’t pass your driver’s test, you probably need to push back practicing merging onto the highway. To ace your test, you may need to first reach a new milestone of memorizing road signs.

7. Reward Yourself Along the Way

Rewards aren’t just for reaching your big-picture goals. Motivate yourself to keep setting milestones by giving yourself small gifts along the way.

Be careful, however, that they aren’t too small. Just as you wouldn’t give a friend or client a cheap gift, nor should you give yourself one.

John Ruhlin, a gifting expert I know, recommends this rule:^[3])

Give yourself something you’d never normally buy but would love to own.

Obviously, don’t go out and buy yourself a new car because you hit your step goal. But a high-end, personalized water bottle might be just the ticket.

8. Give Yourself Breaks

Another way people demotivate themselves is by working themselves into the ground just to reach that next milestone. They beat themselves up, for example, because the nice dinner they enjoyed on vacation blew their calorie budget.

Life is bigger than any one milestone. If you have something to celebrate, indulge a little. If life deals you a setback, realize it may take some time to get back on track. What’s important is that you keep a positive attitude.

9. Get an Accountability Partner

If you’re struggling to set and stick to your milestones, don’t give up; get a partner. Make sure it’s someone who will be firm but fair with you, like a family member or a close friend.

Don’t insist that the accountability partner progress through your milestones with you. Everyone has their own goals to achieve. Do, however, ask him or her to hold you accountable. Suggest some light consequences in case you aren’t progressing toward your goal like you’d hoped.

Even if you can’t get an accountability partner, you can use one of your calendar apps to set daily goals that reminds you of each goal. At the end of the week, go through your calendar and track which goals you accomplished.

Final Thoughts

Some people already find goal setting difficult, so what more if they have to set milestones? To define milestones also means to progress toward your larger goals. Defining milestones on your own may not be easy at first, but you can start with these 9 tips until you get used to it.

More Tips on Setting and Achieving Milestones

• How to Set Short Term Goals for a Successful Life
• How Setting Daily Goals Makes You Achieve Big Success
• How to Set Goals and Achieve Them Successfully

Featured photo credit: Ante Hamersmit via unsplash.com