How to Start a Successful Planning Routine
The simple habit of defining your top 5-8 daily goals each morning is the key to your greatest achievements and success. So, this site being about all things success, I’m going to teach you exactly how to start a life-changing daily planning habit. It’s the most important thing you’ll read here at Millennial Success.
If you stick with daily planning, you’ll automatically boost your confidence, erase your negative self-talk, and break out of the habits that have kept you in “little-me” mode. That’s my promise to you. Give it a month.
But first, a little introduction about how I transitioned from a couch-surfing millennial to a coach who makes his living teaching others how to plan.
*Action steps toward the bottom, if you’re in a time crunch.
How I became Dan the Man with the Plan(ner)
My friends and family used to call me “Dan the Man with the Plan.”
Yeah, it rhymed. But they really used it because the nickname was ironically funny—like calling a muscled-up freak Tiny. “Dan” and “Plan” were mutually exclusive. And I was famously unsuccessful because of it.
Knowing then what I do now about planning and success, I could’ve easily predicted that I’d be jobless and sleeping on my Mom’s red-leather sofa by age 23. But I didn’t know. And Mom’s couch is exactly where I found myself when I started to dream.
I’d failed so miserably in relationships and had suffered so much anxiety and depression that, after the last one ended, I promised myself I’d never date again until I had a functional self to offer as a mate—and that I would share the lessons I learned to help other have better relationships too.
So I decided to pursue the writing dream. But that meant I had to get better if I wanted to actually reach people…and if I wanted to get better, I’d have to be—gasp!—consistent. Which meant writing every day.
I avoided the necessity of planning for as long as I could. But after a year of considering myself a writer and having no credit to my name, and no accomplishments, I suddenly became disgusted with my efforts. I wrote once a week at best. So I started jotting down one simple goal every day:
Write one article.
I wrote it out in a blank-paged sketchbook each morning, and I put one little checkbox next to it. Surprise, surprise…I started writing every day. A week passed, then a month; and I had written more in thirty days than the entire year before—all because I was keeping that goal right in front of me, reminding of the action I needed to take.
I grew a sense of pride for my work. And because I was growing my portfolio, I started applying for and landing my first writing jobs. Which meant more planning.
Once I started getting more work (one article a day, two, three, then four on up) that’s when I was forced to plan for a balanced life—which turned me into an expert.
Even though it was a dream to get paid to write, I started fantasizing about smashing my head through my computer screen at the end of the day. My blood sugar starting fluctuating out of control because I wasn’t eating regularly, which lead to headaches, anxiety and insomnia. I didn’t feel happy because I wasn’t taking good care of my body or doing the things I loved.
Things got so bad that I had to take a month-long break just to save my sanity. In that time I regrouped and started figuring out how to plan for everything I needed to be happy and balanced—not just productive. Besides, I couldn’t afford to take a month off every quarter.
Weekly planning sessions
So for 15-30 minutes every Sunday I sat down with my trusty blank-paged planner and designated one page as my weekly planner. I figured out my writing goals in that time. But the majority of the page was allocated to health/fitness goals, fun/self love goals, self-improvement goals, and giving goals. I thought about the things that made me feel amazing plus things I knew I loved doing and made tangible goals for them:
Play beach volleyball twice this week
Meditate every afternoon
Journal every night
Go rock climbing at least once
Get up and move at least five times every day—squats, burpees, sprints, hikes.
Play guitar for 10 minutes a day
Read fiction before bed
Buy my Mom a massage and take her out for lunch
Then every day I’d reflect on these goals while drafting my daily planning page and pick the ones that worked best for that particular day, scheduling the fun and self love and fitness goals right alongside my work goals.
That’s when life really got good. As a bonus, that quality of my life increased the quality of my work: I began contributing at the biggest magazines in the world, and writing for international companies like Fitbit. The increased value in my articles inspired readers to seek me out for personal coaching, which paid more than even my best writing gigs—and at that point I was making thousands per article.
This extra money gave me more time to do what I loved, to become the fittest and healthiest me that I’d ever been, and to pour my energy into the building up my coaching and planning business—all of the things that mattered most to me.
Now I, the twenty-eight year old who slept on his mom’s couch just four years ago, get to teach executives, CEOs, professors, doctors, nurses, students, and moms and dads from around the world how to plan. And that’s my living.
I like to tell stories. But the main point of sharing mine was to show you how incredibly valuable this habit of daily planning is; and that no matter where you come from, or how bad things seem right now, you’re only one consistent habit away from the success and quality of life you’re craving. I’m living proof.
So here’s a quick step-by-step guide to start your own daily planning practice today:
1-You have to purchase a planner
I recommend a blank-paged, hard-backed sketchbook small enough to carry wherever you go. Has to be blank-paged to repeat the planning template I’ll show to you; and it has to be hard-backed for you to carry it around wherever you go. Six by eight inches is perfect.
You can also purchase the Y-Planner, which comes prebuilt with recurring daily goals (exercise, meditation, limiting emails, etc.) and checkboxes for your top eight goals.
2-Designate a time each morning (or evening) to plan your day ahead.
Having a planner won’t do you any good unless you use it. So carve out five to ten minutes each morning for figuring out your top 5-8 goals and daily habits based on your weekly planner goals. (More on that ahead.) Commit to this time for one month solid.
It’s ideal to place your planning session at the end of your morning routine—gratitude, exercise, etc.—so that you’re mentally prepared to leap headfirst into your goals. But you can also choose to plan the day ahead the night before, after you’ve journaled and gotten new insight on what you need to accomplish for a better tomorrow. Try them both for a week each and see what works best for you.
3-Schedule five planning reminders in your phone
Again, it’s one thing to have a planner, and it’s one thing to have goals, but you have to refer to your goals consistently throughout the day to be reminded of them and to complete them. So, until you’re in the habit of continuously referring to your planner for guidance throughout the day, you need to set reminders in your phone for planner checkins. Five planning reminders from 9-5 works well for all of my clients.
4-Get clarity on your longterm goals
(My longterm goals questionnaire is included at the end of this article. Spend thirty minutes to an hour on it!)
5-Create monthly goals
After you’ve gained clarity on your long-term goals—the template for which is included at the end of this article—you’re going to create a monthly planning page in your journal. (Set a recurring reminder in your phone to do this once every month on a Saturday or Sunday.)
Break the page into quadrants. Then slash a line one and a half inches from the bottom. Top left is daily recurring goals—things you’ll stick with every day. Below that is career goals. Top right is self love/fun goals. Below that is health and fitness goals. And the very bottom row will be giving goals. (For visual reference, the weekly planning template below is almost exactly the same.)
Refer to your longterm goals from above to make relevant and actionable goals for this month. Fill up each box with enough challenges to take up a month. Make sure that your monthly goals are coming from your long-term goals!
6-Establish your weekly goals
Once a week on Sunday, use the same format as above to determine your weekly goals. Refer to this page every morning when you come up with your daily goals. You can use the picture from the Y-Planner below for reference. Create a recurring reminder in your phone (now!) to spend twenty minutes planning out your week every Saturday or Sunday afternoon. Plug that Sunday weekly reminder into your phone, too!
7-Then actually spend five to ten minutes each morning planning out your day
At the end of your morning routine—and before you check any email or messages—spend five to ten minutes planning out the details of your day. You’ll need to have your weekly planner page handy for this: that way you can pick from the goals that you’ve already identified as important to your career, health, fitness, and purpose. (I can’t stress how important it is to actually reflect on your weekly goals when you plan out your day. My clients notice a ten-fold difference in their productivity and focus.)
Use the Y-Planner template below in your own blank journal so that you have your basic habits lined up alongside the goals you come up with from your weekly plan.
Once you commit to this daily planning routine for a month, you’ll be a completely different person. You’ll be organized, focused, and disciplined where you used to be scattered. You’ll be infinitely more accomplished than you were—you’ll be confident, and you’ll be consistent too. You’ll even start to feel more intelligent; because once you start using your planner to make concrete action steps for your smartest decisions, you’ll make smarter decisions out of habit.
So start a good habit today. Get your daily planner. And if you’ve already used a planner but haven’t been consistent, make this your year of consistent daily planning. Last thing: if you want to make this process a ton easier on yourself, purchase the Y-Planner here, prebuilt with the daily, weekly, and monthly templates you need to succeed.
Longterm Goals Questionnaire
Once you purchase a planner, you have to define your long-term goals. You can use the simple template I share with my clients below:
What educational steps do I need to take? What skills do I need to acquire? Do I want to transition into another field? Who do I need to connect with? What would I really love to do, but have been too scared to try? How could I make my current work environment more productive, relaxed, and enjoyable?
Where do you want to be in one year? How will you get there? Do you want to spend more time praying, studying the Bible, or going to church? Do you want to attend spiritual meetings?
What routines will you stick with for the next year that will make you incredibly fit and healthy? What is your ideal picture of health?
Self Love/Self Improvement:
What trips, classes, and adventures do I want to go on this year? What do I really love and want to do more of? What do I need to do more of to be happy? What would I regret not trying, or sticking with? Which fun/enjoyable things can I do regularly each week? Which bigger things would I love to do a couple times a month? And which ones could a plan only a couple times per year?
How many books will I read this year? What successful habits am I committed to for this year?
What social/environmental/spiritual causes do I want to support? Where do I want to volunteer? How can I best help my family and friends? How often will I give? How much will I give?
Which low value habits am I committed to eliminating entirely? Which will I strictly limit throughout the day? For most people, these are social media, texting, email, tv, and hanging around toxic people. Some of these can be foregone—like social media. Others should be limited as much as possible—like texts and emails.
Write down a list of the biggest procrastinations that are making you feel paralyzed. Most people should have at least twenty. Make these procrastinations a priority for your first month of goal setting!