The Daily Wins Checklist: An Accountability System for Your Most Important Priorities

Here’s something you already know: Doing new things is hard.

Whether your priority is to get in shape, build a meditation habit, or find a new job…

• Fear will prevent you from taking action.
• Depleted motivation will test your willpower.
• Impatience will cause you to feel frustration.

In my journey to make Mindful Ambition the best it can be, I rely on one philosophy to do my best work:

If you focus on the right things, do them consistently, and stay patient, it’ll all work out.

Although it’s simple to understand, in practice this is difficult:

1. How do you know what habits are right to focus on?
2. How do you stay disciplined and focused to do them consistently?
3. How do you stay motivated to be patient and keep working?

I made it my mission to design a tool to help overcome these challenges.

I experimented with this tool for 5 months before publishing this article. And since then, I’ve continued to update and refine it as my priorities have changed. I’m excited to share the tool with you here.

Introducing the Daily Wins Checklist (DWC)

The Daily Wins Checklist is a powerful tool that supports both discipline and appreciation to build and maintain habits.

• Discipline is important to overcome the resistance that prevents you from taking action. (e.g. Distraction, forgetfulness, procrastination, etc.)
• Appreciation is important to stay motivated and build satisfaction in your work as you go.

There’s one rule that separates a Daily Wins Checklist from your typical to-do list: A DWC only includes behaviors that align with your priorities and values.

That’s the first part of my core philosophy: focusing on the right things.

In your life as a whole, that means spending time on things that matter to you. (Aligned with your priorities and values.)

In a more specific area of life (business, fitness, …) that means spending time on high-impact activities. Things that get you more “bang for your buck”.

“But tracking seems like a lot of work…do I really need to do this? What’s so good about a checklist?”

I’m glad you asked. 🙂

5 Surprising Benefits of Checklists

I created my first Daily Wins Checklist by following my instincts.

I thought to myself…“If I want to do these things every day, maybe a checklist would help me stay accountable!”

Since then, I’ve decided the checklist structure is here to stay. Here are 5 reasons why.

1. Checklists Emphasize Behavior, Not Outcomes

End-goals emphasize the outcomes of your actions, which are out of your control.

On the other hand, checklists emphasize the actions themselves, which are in your control.

James Clear has a nice way of describing the value of focusing on behavior:

“If you completely ignored your goals and focused only on your system, would you still get results? For example, if you were a basketball coach and you ignored your goal to win a championship and focused only on what your team does at practice each day, would you still get results? I think you would.”

In the end, your actions are all that matter, as they determine whether you make progress.

2. Checklists Remind You When You Forget

Half of the challenge of mindfulness is remembering to stay present. The same goes for remembering to perform any habit or behavior!

Every habit has a “trigger” of some kind that reminds you to take action. Then, a reward of some kind reinforces the habit in your brain.

Looking at your checklist serves as an additional trigger to take action when you might forget otherwise.

3. Celebrating Small Wins Makes You Feel Good

Focusing too much on the destination of where you want to go cultivates dissatisfaction. Every day you aren’t at your goal, you’re bummed. Satisfaction only comes upon reaching the goal.

On the flip side, sourcing satisfaction from the journey instead of the destination gives every day a shot at being a great day.

It’s easy to go through a day and not realize all of the progress you’ve made. A checklist helps you appreciate the daily steps you’re taking to live well.

4. Checklists Create a Virtuous Cycle

The first steps of doing something new are always the hardest. But after a bit of consistency, you build up momentum. It feels easier to keep the streak going!

There’s something very motivating about keeping a streak alive. A checklist is a visual manifestation of your consistency.

5. Checklists Foster Greater Self-Awareness

A 2008 study by Kaiser Permanente revealed that dieters who kept a “food diary” lost twice as much weight as those who didn’t track what they ate.

The simple act of writing things down keeps you aware of your behavior. This awareness makes it easier to behave in a way that aligns with your priorities and intentions.

How to Create Your Daily Wins Checklist

OK, enough background information, it’s time to get started!

Let’s walk through the steps for you to create your own Daily Wins Checklist.

Step 1: Identify Your Priorities

What are your current priorities in life? When you’re living your best life, what are you focused on?

These are big questions. Take your time here. Trust your gut.

If you haven’t taken time to consider this deeply, I recommend starting with the 20-Minute Life Checkup. It’s an exercise to assess how your current behavior aligns with what you care about.

To give you an example, my main priorities are:

• My physical and mental health
• Helping people live well (My work through Mindful Ambition.)
• Cultivating meaningful relationships with people I care about
• Learning and growing

There’s no “right” mix here. It’s different for everyone, and should be specific to you and your life!

Step 2: Pick Your Daily Behaviors

What behaviors do you want to perform every day to make progress on your priorities?

The behaviors on my Daily Wins Checklist relate to sleep, nutrition, movement, work productivity/creativity, learning, and social activity. Each one directly supports my priorities.

A good friend of mine uses the “Health, Wealth, Love, and Happiness” framework for his most important habits. I like that framework because each category supports a different element of your wellbeing.

For example, if you used the HWLH framework, you might identify these habits:

• Health: No eating foods with added sugar.
• Wealth: Send 5 sales emails.
• Love: Take time for morning coffee with your spouse/partner.
• Happiness: Meditate each morning.

Step 3: Picking Other Regular Behaviors

What non-daily behaviors are important to you living your best life?

Not every action that supports your wellbeing is best completed every day. You may have some bi-weekly, weekly, or monthly practices.

My Daily Wins Checklist includes a “weekly” category with things like:

• Calling family/friends to maintain important relationships
• Exposing myself to a new experience of some kind
• Going for a long walk

I don’t need to do these things every day. But I’m showing up at my highest when they’re a part of my life.

Step 4: Formatting Your Daily Wins Checklist

Now that you’ve identified a range of behaviors to include in your DWC, you’re ready to make draft #1!

Below are 3 different formats you can consider using.

Your DWC may look completely different from mine, or a friend’s. After all, it’s rooted in your priorities, goals, and values. Take time to tailor it to what you need most!

Format 1: The “Extreme Focus” DWC

What it’s best for: You have one main priority. It’s far-and-away the most important thing for you to focus on.

What it looks like: A month-long calendar. Each day is a big checkbox.

How to make it:

1. At the top, write an intention of your behavior: “I intend to _______, __ times per week.” (Stating in advance when and where you will take a specific action may double your chances of success.)
2. Display the checklist prominently where you’ll see it each day.

Alternate option: To add an element of social accountability, make your checklist a shared Google Doc. Share the doc with a friend or two to help you stay accountable. The downside of this is that you’ll have to mark it twice if you want the benefits of a physical checklist.

Format 2: The “Well-Rounded” DWC

What it’s best for: A well-rounded approach to support multiple dimensions of your wellbeing.

What it looks like: A weekly format, where each day includes ~5-7 primary behaviors.

How to make it:

1. At the top, add this week’s dates.
2. Add your behaviors to the left-hand column, in the general order that you’ll perform them each day.
3. Add weekly behaviors in a separate category on the bottom of the page.
4. Keep the checklist handy to refer to throughout the day.

Format 3: The “All-Inclusive” DWC

What it’s best for: Celebrating more daily wins.

What it looks like: A weekly format, where each day includes ~20 behaviors.

How to make it:

1. At the top, add this week’s dates.
2. Add your behaviors to the left-hand column, in the general order that you’ll perform them each day.
3. Add weekly behaviors in a separate category on the bottom of the page.
4. Keep the checklist handy to refer to throughout the day.

Note: This is the DWC format that I used at the time of writing this article. I first started with a more focused approach (like format 2.) Following that, I was inspired by Dustin Watten’s articles on “The List“, and expanded my checklist to include all of my daily habits.

Putting the Daily Wins Checklist to Work: Consistency, Not Perfection

Using your checklist is a straightforward process:

1. In the morning, take a quick scan of your DWC.
2. Mark your progress as you move throughout the day.
   • Use check-marks to indicate a completed behavior.
   • If the behavior is in multiple parts (e.g. Take 3 mindful breaks each day), use tally marks to track your progress.
3. Revisit your DWC at daily “milestones” (e.g. Lunch, dinner, before bed.) This helps prevent honest forgetfulness by keeping habits top of mind and reminding you to check off completed behaviors.
4. When you fail to complete something as intended, don’t fret. Use your awareness of this lapse to re-commit to your original intention.
5. When you notice a pattern of slip-ups, take time to reconsider your approach. Examine the resistance you’re feeling, or what obstacles are preventing you from completing that behavior.

The Daily Wins Checklist isn’t about making you perfectly disciplined with your habits. That’s just unrealistic.

Instead, think of it as a tool to make more consistent progress on the things that matter to you in life.

I don’t think I’ve had a “perfect” week since I started this. But my hit rate is significantly higher than it would have been otherwise.

And when you’re making consistent progress on things that matter to you, what more can you ask for?

I wish you well. 🙂