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Aligning Your Calendar With What Matters Most
12 min read

Aligning Your Calendar With What Matters Most

Aligning Your Calendar With What Matters Most
“If you take care of the minutes the years will take care of themselves.”
-Tibetan saying

Let me fill you in on a secret: you have far more control over your calendar and time than you think you do. This is one of the secrets I’ve learned in my first year as a coach.

At the end of 2019, I made a significant career change from institutional VC to coach and angel investor. COVID also upended how I work and live. These two massive shifts forced me to evaluate how I spend my time and what I truly value.

Through this metamorphosis, I became the architect of my life and calendar. Once I began to align my calendar with what I value most, there was a massive shift in my priorities, energy, happiness, and creative output. I began to recognize and realize my full potential as a coach, creator, father, and human.

Despite being a two dimensional tool, our calendars create a three-dimensional tapestry of our lives. What is on our calendars dictates what we focus on and how we spend our  time in the physical world. And if we’re not mindful and deliberate, they can rule our lives and cause us to fall into routines that don’t serve us, changing who we are and even the direction of our lives.

Before I took control of my time, there wasn't much structure, consistency, and rhythm to my days and weeks. I would often become frustrated and mildly depressed each morning when I would review my upcoming day.

Every week was a smattering of back-to-back-to-back coaching sessions, business pitches, and networking meetings. I wasn’t leveraging the optimal time for creative work, and I never blocked large chunks of time for deep, focused work. I rarely made time for the activities and projects that were most important, both personally and professionally. I wasn’t making time to become the person I wanted to become. I didn’t know what to work on or what to say yes to. And I wasn’t conducting any kind of audit of my schedule, that could help me consistently capture learnings and plan for what was coming next.

Here’s what I was doing: I was context switching between roles and projects every day. I was feeling guilty when I wasn’t working. I was using my time in ways that didn’t energize me or move any projects forward. I was more focused on staying “busy” and making other people happy than I was living for what mattered most to me. I was putting other people's priorities before my own. Saying I was reactive, overwhelmed, unfulfilled, and burnt out would be an understatement. Frankly, I didn’t have a great system to manage my life. At the end of each week, I was often drained and left wondering why I hadn’t accomplished much creatively.

This was my calendar in January 2020. Believe it or not, most weeks in 2019 were crazier than this.

Even though I had been working for myself for 6 months, I still felt like I was always working for someone else. I didn’t have the control and freedom that I sought in becoming an entrepreneur and coach in the first place.

I’d had enough. Over the summer, I forced myself to take a step back. I sought to understand whether my time was actually aligned with my mission, values, and goals. I wanted to reorient my calendar toward service, creativity, balance, and personal growth—to get my calendar to work for me rather than the other way around. I

By the end of 2020, I significantly changed how I prioritized and invested my time. This required experimentation, discipline, and hard work. I went from being reactive and busy to focused, productive, and creative. I finally began to say “NO” to the myriad requests flying at me. I finally began to block time. I finally began to treat time as my most precious asset. As a result, I accomplished more than any year before. That’s not by mistake.

This is what my calendar looked like by the end of 2020.

These are the changes I made:

  • Start my day with a morning meditation before my wife and daughter wake up.
  • Take a 20 min walk in nature to get the blood flowing and think about the day.
  • Reserve 8:15-11 am for creative thinking and deep work. This time is sacred.
  • Schedule coaching sessions and meetings between 11-5 pm.
  • Made default meetings 30 min unless a coaching session.
  • Block 5-6 pm on Tuesdays and Thursdays for exercise.
  • Protect 6-7 pm for time with my wife and daughter.

My calendar now reflects my mission and what I value most. When I review the coming day each morning, I now see my whole self. It includes not only professional items but also personal and family. It’s no longer just about work. It captures far more than meetings, pitches, and coaching sessions.

This was more than a transformation of my calendar. It was a transformation of me and my life. I wanted my calendar to reflect who I truly am so I can live more intentionally. I’m now more balanced, creative, productive, focused, and fulfilled. I also feel like I finally have the freedom and control that led me to entrepreneurship.

What to know the best part? If I can do this, so can you.

This is possible for everyone, including yourself. You can have more power over your calendar and time. It no longer has to control you.

You’re in the right place. I’m here to help you take first steps to becoming the architect of your time and calendar.

This process is all about helping you increase awareness and cultivate intentionality.  It’s hard to build a new foundation if you don’t know what you want your house to look like.

So where do we begin?

In order to cultivate awareness and intentionality, I’ll help you determine your values and mission. If you don’t know what’s most important and what your purpose is, then your calendar is unlikely to reflect those.

Once those have been defined, I’ll guide you through a calendar audit. This will help shed light on how you’ve been spending your time and if you’ve been living in congruence with your values and mission. You’ll develop a sense of your habits and tendencies. You’ll also have a better sense of what fills you up and what drains you.

From there, I’ll help you begin to determine which habits you’d like to ditch and behavior changes you’d like to implement.

I invite you to step fully into this process. This won’t be easy and it’s not a panacea. Here’s what I can assure you: you’ll have a much better sense of who you are, what’s most important, and how you want to design your days and weeks.

Values

When you live by your core values, you can design a schedule that gives you energy and is in alignment with who you are and who you want to become.  

Values aren’t woo woo. They are core to who we are. They show us what is most important, what drives us, what lights us up, and what we’d like more of. They show us what we can refuse to tolerate.

When we know what we value, we tap into who we truly are. We feel energized and powerful. When we don’t tap into our values, we are out of alignment. We feel sluggish, drained, and unmotivated.

I recommend asking yourself these questions every twelve to eighteen months, because our values shift and evolve as our lives and circumstances change.

Here are some prompts to help you identify your core values:

  • What are 5-10 words that describe what’s most important to you?
  • What was a peak experience in your life? What happened? How did you feel?
  • What makes you angry, frustrated, or upset?
  • What energizes you and fills you up?
  • What gives meaning to your life?
  • When were you happiest, most fulfilled, and most satisfied? What were you doing?
  • How would 3-5 family members or closest friends describe your values?

Now it’s time to synthesize what you wrote into 3-5 core values. What patterns do you notice? Are there any themes? What’s the essence? Where is there tension? You can refer to this list of core values from James Clear if you’d like some help.

Remember to take your time. This process can take one to two hours. Don’t rush it. Your values should become the foundation of everything you do.

Mission

You might think about 'missions' mostly when it comes to startups. But I believe everyone should have a clean mission statement that they can refer to when they're not sure how to proceed. It's a north star, a guiding light. It can be as long as a manifesto or as short as a mantra.

If you can’t connect how you spend your time to an overarching purpose, then you could work 60 hours a week but be running in the wrong direction. In other words, you could be the hardest working and most productive person in the world, but be focused on the wrong activities. For many years, I scheduled meetings without being intentional. That’s how my calendar became filled with meetings and activities that didn’t energize me.

By having a clear mission statement, you can determine how you choose to spend your time and what goals to focus on. Every time you’re prompted to allocate time to a task, project, or even job, you’ll begin to ask yourself: does this align with my mission? You will have an easier time identifying what opportunities, meetings,activities, and paths you should say yes or no to.

A mission statement can be personal, professional, or incorporate both domains. For some people, defining a personal mission statement is more important than professional; for others it’s the reverse. I believe it depends on the stage of life and what values you’re prioritizing.

For example, my mission statement is to help the creators of tomorrow realize their full potential as humans and leaders. I achieve this through coaching, investing, and writing. As you can see, this is largely professional. I do intend to add a second sentence to incorporate my personal life and I look forward to sharing it with you when I do!

I’m here to help you figure out your mission and north star. How do I know what they are?

A good mission statement should incorporate your values, passions, dreams, goals, aspirations, personality traits, and skills. It should incorporate what you hope to accomplish, who you become, and what the impact will be.

Here are some prompts to help you identify your mission:

  • What are some nouns to describe who you are? (e.g. father, coach, blogger, etc.)
  • What is the world you want to create?
  • What do I view as my purpose?
  • What do I want to be remembered by?
  • How do I want to spend my time?
  • What am I passionate about?
  • What drives me?
  • What do I believe in?

Once you’ve answered those questions, begin to note patterns and organize them by theme. What begins to emerge? What’s the essence of what you’ve captured? Now try to distill it into one or two sentences.

A good mission statement requires time and effort to create. I’d allocate at least two hours to this process. While they might seem simple, capturing the essence of your purpose is not an easy task.

Once you have defined your mission, make it visible. Put it in your office. I have mine on a sticky note on my computer. I also have it as part of my Twitter bio. Share it with the world. Make it visible so you can begin to incorporate it into how you design and spend your days.

Calendar Audit

Understanding how you’ve spent your time uncovers habits, tendencies, priorities, and more. Awareness leads to change. That’s why I recommend conducting a calendar audit.

Here’s where to start. Review your calendar from the past three months and make a list of the activities you performed in the course of doing your job. I also suggest doing this for non-work related items as well. Be specific (e.g. weekly team meeting, networking with Jane Smith, prep pitch deck, filed expense report, etc.). Then put an arrow next to each activity indicating energy level (up, neutral, down). Did it energize or drain you?

This process will help you begin to see what activities bring you in or out of alignment.

As you review your calendar, consider these questions:

  • How would you categorize the time spent (e.g. projects, coaching, investing, health, family, etc.)?
  • What meetings or activities energized me or drained me?
  • How does your personal life appear in your calendar, or not?
  • What was time well spent?
  • What time do I wish I could get back?
  • Where is there waste or inefficiencies?
  • Have I been focused on the right activities?
  • How much time am I giving myself for deep work?
  • How do appointments make their way to my calendar?
  • How much time do I have for rest, recovery, and play?
  • What recurring meetings do I have weekly, monthly, quarterly?
  • How does my calendar reflect my values and mission?

This exercise usually takes an hour. Once you’ve answered those questions you should  begin to see how you’ve been spending your time and how those activities make you feel. Again, our goal here is to create more awareness. With more awareness, the more power and choice you’ll have.

Habits and Rituals

By understanding your tendencies, you can begin to see your ingrained behaviors and patterns that lead to meetings and other commitments that don’t give you energy or that otherwise actively work against you. By making the unconscious conscious, you can start to change.

Many of us, myself included, are on autopilot most days. That’s why assessing habits and rituals is an important step in aligning your calendar with who you truly are. Some habits are positive, some are negative and counterproductive.

  • What habits are healthy and productive?
  • What habits are limiting and holding you back?
  • What habits do you want to implement but haven't yet?
  • What habits—negative and positive—have you had in the past that you don't have now?

The point with this exercise isn’t to create overwhelm by listing all of your bad habits and all of the changes you should make. It’s to create awareness so you can decide where you want to start. Our goal here is intentionality. Change always begins with awareness and small steps.

Moving Forward

It’s now time to turn contemplation into action. This is where the rubber meets the road.

For me, the first change I made was blocking 8:30-11am for deep work each morning. Rather than try to change five things at once, I decided that one change was most important. I viewed this as a small experiment for 30 days.

Once I built that into a daily habit, I introduced other changes one at a time. Eventually, I removed non-essential recurring meetings, set my default meeting time to 30 minutes, and added personal items to my calendar. My calendar evolved over six months. It didn’t happen overnight—as much as I wish it did. But the best method is to identify something specific and achievable to get the ball rolling and see how much you’re capable of.

So for your calendar update, choose what makes the most sense for you and aligns with who you are and who you want to become.

Here are some:

  • Adding personal items to your calendar
  • Blocking time for exercise, meditation, etc.
  • Prioritizing deep work
  • Scheduling breaks to recharge
  • Removing recurring meetings
  • Negotiating new meeting formats with colleagues (like replacing some Zooms with walking meetings over the phone)
  • Prioritizing time for side projects, creative pursuits, and learning
  • Restructuring how and when you process email
  • Deciding how meetings or activities make it to the calendar
  • Taking morning walks
  • Restructuring your day
  • Finding an assistant or use a scheduling tool like Calendly
  • Calling family & friends

These are just a sample of possible changes you can make. There are many more.

Here’s my challenge to you: what deliberate shift—small or large—you can make to begin to align your calendar with what you value most? Don’t pick five or even three. Just one.

What change are you willing to make? On a scale of 1-10, how likely are you to do this? What might get in the way? What have you already accomplished that will make the change possible?

View this as an experiment. Don’t get too attached to the results. Optimize for learning. Get curious and present. See what works and sticks. Commit for a week and measure your progress.

At the end of the first week, ask yourself if you need to make any tweaks. Rinse and repeat this for a month. Really focus on creating one new habit, behavior, or ritual. Most important, don’t forget to celebrate your wins every day. Reward yourself for making progress, no matter how big or small the steps might be.

After a month or two, you should begin to see a shift. At that point, you can consider adding new habits, rituals, and routines to your calendar. Maybe one at a time.  When you compound this over months, your calendar will start to reflect your mission, your values, who you are at the core, and who you want to become.

This is the beginning. Be easy on yourself and enjoy the process.

Closing

Your calendar can be your ally rather than your master. Getting it to align with what’s most important can be a massive unlock. This is not just about getting more done.

As I hope you’ve seen, this process has radically changed my relationship with time and how I spend my days. I can assure you from experience that it’s not easy, but it is possible, and the rewards are boundless. I’m more productive, happier, focused, creative, and balanced. Most importantly, I’m living a life that’s mission-driven and intentional. I’m being true to who I am as a dad, husband, coach, angel investor, and human being.

The biggest reward? I now reserve time every weeknight to spend with my daughter and wife. No distractions. This time is priceless. I’m able to show up for them with more presence and intention. Best of all, I no longer feel guilty about the time I spend not working. This has been a highly conscious choice.

I’ve realized something else, too. If you don’t create the time to listen to yourself, take care of yourself, you can’t really be there for others. The rest of my calendar is now designed to keep me healthy enough to be the best dad and the best partner I can be.

I’d love to hear how this process goes for you and what you learn along the way. You can always email me at steve@highoutput.co. Good luck!

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