Tips for Making Tough Decisions

making tough decisions

Confession: I am not always good at making big decisions.

Many of the answers to the biggest questions I’ve ever asked myself have come to me intuitively, which meant that I really didn’t need to decide, because I just knew.

When I adopted my first pup, I wasn’t looking for a dog. In fact, I’d just said to a coworker the week before, “It’s amazing to me that single people get dogs, because I imagine that they really inhibit your freedom!” I was single. And precisely one week after saying this, I had a dog.

I had been picking up two friends’ dog from doggie daycare when I saw his face on a crumpled up flyer, taped to the front counter. As if the words had come to me from somewhere outside myself, I asked if I could meet him. When I met him, I knew on an intuitive level, long before I knew on a conscious level, that he was my dog. There was no decision - just a deep sense of knowing. When my friends arrived to pick up their dog, there were two dogs, instead of one. My friend just looked at me with a knowing smile.

The same thing happened the day I put in my notice at my job. While I was sitting inside of an office, there was a moment in which I swear I saw the clouds part and a big ray of light shine through, at which point I said, “my last day will be May 1st.” Once again, there was no decision -  just a deep sense of knowing, and the words came out of my mouth from what felt like a source greater than myself.

All of this clouds parting, light shining through, voices from above type of clarity is great, but it means that decisions can be incredibly challenging for me when this isn’t present. In the rhythm of normal work and life, it’s not always possible to wait around for this moment of instant clarity to strike. There are timelines and deadlines and normal life constraints that aren’t always conducive to waiting for an answer to appear.

In these situations, I often use a variety of tools and systems to explore the different possibilities at hand, to help lead me to the best decision based on the information I have at the time. Here are a few of my favorites.

Try on the different options.

Imagine yourself in the different scenarios at hand. For example, if you’re considering whether or not to leave your current job, you might imagine yourself staying in your current job, and leaving your current job. What does each option feel like? What do you see in each of these scenarios? What is happening, and how do you feel? And then, after exploring options A and B, push yourself to think about a third path. Is there another option C that could exist that you might not have thought of before? For example, pursuing your passion as a side hustle while staying in your current job? Or, exploring a role change within your current company? Try each of these on as well and notice what emerges. Pay extra attention to how you feel as you sit with each one.

Write to yourself.

Write out the question you’re currently considering, and write out whatever answers come to you, without filtering or judging the responses.

For example, you might write: “what do I really want?” and then allow yourself to write down whatever comes to you as an answer. Write down whatever comes up, without thinking about it or filtering it or wondering whether it’s real or not - just write it down.

Then, when you’re finished writing, you can go back and revisit what you wrote. What do you notice? What are you surprised to see on paper?

Often we know more than we think we do, if we get quiet and tune in.

Check In with your Future Self.

This is the version of us who is 5, 10, 20, or maybe even 30 years older. This process involves consulting our older self and asking about the questions that are are pondering today. What path did she pick? What advice might she give us knowing what she knows now? What decisions led her to where she is today?

Write out Three Different Life Plans.

Write out three possible paths for your life, in 5-10 year chunks.

  • Path 1: the path you’re on right now.

  • Path 2: a slightly modified version of the path you’re on right now.

  • Path 3: an entirely different option - or the “if anything were possible option.”

Check in with each of these three paths. Which one feels most alive? Which one feels most aligned with your values and goals? Which one gets you most excited?

And, what is one small step that you could take toward the path that speaks to you most?

Decide on a First Small Step.

Often big decisions feel overwhelming. If we are considering whether to leave our job, for example, a number of fears and saboteurs often kick in - What if we don’t find anything better? What about the benefits? What if we realize we made a mistake?

The first decision might not actually be to leave your job. It might simply be to update your resume. What if you start there and take some of the pressure off? Usually the first small step can be done without a lot of disruption and under the umbrella of security and safety of our current context, and is much easier than we think.

These are a few of my favorite strategies to use when instant, intuitive clarity isn’t present. Here are a few additional resources that may come in handy along the way, as well:

Good luck as you ponder the big decisions you may be facing right now. Want some help along the way? Please feel free to reach out to explore how we might work together throughout the process.

“Once you make a decision, the universe conspires to make it happen.” Ralph Waldo Emerson

Following Your Passion When You're Not Quite Sure What Your Passion Is


“Follow Your Passion!”

“Live Your Purpose!”

We’ve all, I’m sure, heard this advice way too many times to count.

While inspiring in some cases, it can feel like slightly unhelpful advice when we’re not sure what our purpose is, or where our passions actually lie.

Discovering these things is not, of course, an overnight process. For some of my clients, the desire to get more clarity in the above two areas is the reason they hire me as a coach. They’ve usually been wildly successful doing something other than their passion or what feels like their purpose, and together we work to discover what a new path forward might look like.

Hiring a coach is a great way to gain some powerful traction on the above questions. That said, there are some small things we can do on our own, as well, to kick start the process. Here are a few of my favorites.

Pay Attention to Curiosities.

“Instructions for living a life. Pay attention. Be astonished. Tell about it.” - Mary Oliver

I see many people put pressure on themselves to figure out the answers to these enormous questions about purpose and passion in one massive epiphany that comes with a bolt of lightening at 2 in the morning. While sometimes the answers come to us this way, often the answers are the result of paying better attention over a period of time.

The first thing we can begin to pay attention to is curiosities.

  • What are you curious about?

  • What are you interested in?

  • What do you find yourself reading about in your free time?

  • What types of books are you drawn to?

  • What do you find yourself researching online, just because you want to know more?

  • What are the themes of conversations you’re having with friends?

  • Who are the people you find yourself following or drawn to - through blogs, articles, or social media?

Pay attention. Write these things down. Make a list and continually add to it. Allow yourself to simply add to it over the course of several weeks. And then, look back to see what you notice.

Track Your Energy.

What are the things, throughout your days, that give you energy? What are the things that deplete your energy?

Pay attention. Write them down. I recommend making a good old fashioned T-Chart with a list of “+” and “-” and adding to this list throughout your days.

Do this exercise at work.

  • When do you feel engaged and energized?

  • What are the projects you feel excited to work on?

  • Which types of conversations energize you?

  • And, on the flip side, when do you feel that you’re drained or depleted?

  • Which projects or tasks do you dread tackling?

Write them all down on your list.

Do this exercise at home.

  • What are you doing when you feel totally energized at home or around the house? Are you working in the garage or tackling a craft project or cooking?

  • What are you doing when you feel depleted or drained at home?

Put all of these things on the list.

Do this process for a week or two and notice, without judging, what emerges. Are there any trends or patterns? Or perhaps any surprises?

This process is not only helpful for informing your passions and purpose, but also for making small tweaks that make everyday life more easeful and joyful. I’ve made several small but game changing tweaks to my everyday workflows and rhythms as a result of my findings from this process.

Go Back In Time.

Think back to when you were young.

  • What did you love to do when you were little?

  • What types of games did you play?

  • What were your favorite types of toys to play with?

  • What did you want to be when you grew up?

Think back to high school and college.

  • When were you happiest?

  • What activities were you part of?

  • When were you having the most fun?

  • When did you feel most engaged in what you were doing?

  • When did you feel the most fulfilled?

Make a list of everything that comes to mind. Dig up some old photos and notice what you were doing.

For most of us, there is at least some thread that relates to our passion and purpose. In my case, for example, I played school almost every day. I had an entire school set-up in my basement: blackboard, overhead projector (the old school kind with the plastic sheets and the wipe-off markers - yes, I was that into playing school), chairs, and supplies. All through high school and college I taught water aerobics to adults and swimming lessons and Spanish for kids. I absolutely loved the process of teaching and learning.

While for a long time I thought all of this meant that I wanted to be a teacher within our school systems, I realized in my adult life that I wanted to create spaces of learning and self discovery and transformation and personal growth - for adults - which is exactly what I’m doing today. Putting these pieces together was not an overnight realization - it came after much reflection, lots of additional education, and plenty of time in the corporate world doing something entirely different.

Do Stuff.

Perhaps most importantly, to discover our passion, we need to do stuff that we are passionate about. To uncover our purpose, we need to take purposeful action.

Generally speaking, we will not discover our purpose solely by sitting at home reading books about purpose. We will not uncover our passion solely by reading inspirational quotes about passion, even if they are written in perfect calligraphy (you know the ones I’m talking about).

Rather, we will discover our purpose and our passion by taking action, with purpose and with passion.

Sign up for a class. Take the workshop. Reach out to that person you worked with 10 years ago who is now doing something super interesting and reconnect. Subscribe to the industry magazine. Volunteer with an organization that sparks your interest.

Try stuff. Dabble. Tinker. Allow yourself to be curious, and unattached to the outcome.

Do stuff just for fun.

In Summary.

To discover our purpose, we need to take purposeful action. Purposeful action does not need to mean quitting your job on a whim and moving into a Westfalia van for the next 3 years (though it certainly could if you feel called to do so) or going on a year-long spirit quest in Bali (though it certainly could if you feel called to do so). Purposeful action can mean making a list; starting your day with intention; paying attention to your curiosities; doing things that bring you joy; and noticing what you discover along the way.

The Pareto Principle


I ordered my green smoothie, minus the chia seeds.

“Just so you know,” he said, “after Friday we’ll no longer be serving smoothies. They generate the smallest amount of our revenue and cause all of our headaches.”

“Have you heard of the Pareto Principle?”

“Yes, I love the Pareto Principle!”

We proceeded to geek out on the Pareto Principle for the next 10 or so minutes, after which I walked out with one of the last remaining green smoothies on the menu.

The Pareto Principle, or the 80/20 rule, states that for many events, 80% of the effects come from 20% of the causes. It is credited to Vilfredo Federico Damaso Pareto, who was born in Italy in 1848. In his case, he noticed that 80% of his pea plants generated 80% of the healthy pea pods, and then went on to discover that 80% of the land in Italy was owned by 20% of the population.

In the case of the restaurant I visited, 80% of their stress, irritation, and time investment tied back to 20% of their menu items (in this case, smoothies and smoothie bowls). And this 80% stress, irritation, and time investment produced under 20% of their revenue.

We can apply this same principle to nearly any type of business, to how we structure our work day, to the way we prioritize our work, and even how we approach our health and fitness.

Like Essentialism, this is one of those things that (for me) feels like common sense, yet takes constant attention and intentionality to apply in everyday life.

Here are a few ways that I like to practice the Pareto Principle.

  • Looking across all the projects I’m currently involved with, which fall in the 20% that create 80% of the positive impact and also feel the most joyful?

  • On the flip side, which projects fall in the 20% that create 80% of the stress and headaches?

  • Looking at the flow of my workday, where can I invest 20% of my time and effort for 80% of the returns? (For me, when doing independent work, the answer always falls in the early hours of the morning.)

  • Looking across my life at the things that aren’t working as well as they could be, where are the 20% of small irritations that are causing 80% of the lack of daily ease? (often, for me, this ties back to some sort of misalignment with my calendar.)

  • Which 20% of clothing items do I wear 80% of the time? (I’ve been working on continuously donating that other 80%, as for me there is a very clear 20%. I tend to wear the exact same few outfits on rotation.)

  • In which 20% of our house do we spend 80% of our time, and how can we maximize that 20% for the way we live?

  • Looking at my list of monthly, weekly, and daily to-dos, which 20% will yield 80% of the results?

The Pareto Principle, or the 80/20 Rule, can help us to focus our time and energy on the things that yield the highest results.

Do you use the Pareto Principle? If so, in what ways has it been helpful for you?

Escaping the Endless Cycle of Yes

Escaping the Endless Cycle of Yes

Saying yes too much. Difficulty saying no. Overcommitting. Prioritizing other people’s priorities over your own. Becoming stretched too thin. Taking on the project because other people dropped the ball. Over-serving the committee because none of the other volunteers follow through. Expressing interest in something and then suddenly finding yourself in charge of it. Saying yes to an opportunity because it’s amazing, but then wondering when the heck you’re going to fit it in.

Anyone else struggle with one or more of these things?

If you do, I hear you. I see you. I get you. My natural tendency is to do these things too. I quickly see possibility and potential in any given situation, which means that in my mind I quickly jump from where we are right now to where we could be in the future. It also means that sometimes, in the moment when the opportunity presents itself, I overlook the steps in between - for example, how long it might take to get there or what else I have on my plate. As you can imagine, this has gotten me into trouble on more than one occasion.

It is a constant, daily (sometimes hourly) practice for me to work with my natural tendency (seeing possibility, potential, what’s possible, allowing myself to be excited and enthusiastic about all of this) while also incorporating everyday realities such as time, capacity, and scheduling.

This is not a post about saying no more, or saying yes less. Rather, it is a post about moving from, as Greg McKeown says, the trivial many to the essential few. It is a post about saying yes in a way that aligns with your values and your priorities. And it is a post about remembering that we are the creators of our own life, versus allowing others - or our inboxes or our friends or other on the committee - to control it for us.

Here are some strategies I use in this ongoing pursuit to align my time with my values; my priorities with my calendar; and my decisions with my core purpose in this world.

Wait at least 24 hours before responding to any new opportunities.

First, this provides time to check this opportunity against my values and reflect on the following questions:

  • Is it in line with my values?

  • Would this opportunity be moving me toward my vision?

  • Is it in line with my priorities for the year?

It also allows me time to think about my capacity and bandwidth, and also the tradeoff costs.

  • Do I have time to take this on?

  • If I say yes to this, what will I need to say no to?

  • When will I have time to do this? And is it in line with the timing of the opportunity or event?

  • Do I actually have time, or would I be trying to squeeze it in?

Ask Myself: If this opportunity wouldn’t have come to me from elsewhere, would I have actively pursued it on my own?

This, of course, can be a particularly challenging question as a business owner, and especially for new business owners who are working to build their businesses.

“No but…’s a good opportunity….” But is it a great opportunity? Is it aligned with the work you most want to do in the world and the people you most want to serve?

In the beginning, as new business owners and entrepreneurs, as long as the opportunities are aligned, I tend to recommend being more generous with what you say yes to. This provides an opportunity to try out various things, work with several different types of clients, and learn more about what you like (and what you don’t). And then, as your business grows, you can use these early experiences to shape future decisions and areas of focus.

That said, if the only reason you are saying yes is “to get more business” or “to generate referrals” or something gross like that, I suggest revisiting. It should also be fun, or interesting, or an opportunity to work with fabulous people.

If you are approached about joining a board or a committee, ask the same question. While flattering to receive the invite, is this the cause you care deeply about? Is this the way you want to invest your time and energy? Are the people on the board ‘stunning colleagues’ who you will be excited to gather with each month or each quarter?

Is the opportunity a Hell Yeah?

Is the opportunity a Hell Yeah on its own? If not, what would make it a Hell Yeah? And if you can’t think of anything that would make it a Hell Yeah, is it really worth saying yes to?

As Derek Sivers famously said, “if it’s not a Hell Yeah," it’s a no.”

The way I like to look at this is a Big Yes or a Little Yes. The Big Yes is aligned with our values, our vision, our priorities. The little yes comes from a place of ‘should’ or obligation.

As new opportunities come your way, ask yourself if it’s a Hell Yeah. If you can’t think of any conditions under which it would be a Hell Yeah, if it isn’t already, then you likely have your answer.

What are the conditions/terms under which I would love to say yes?

Related to the above, if it isn’t a Hell Yeah, is there anything that would make it worth it?

For example, for new entrepreneurs or business owners, the truth is that every single project might not be a Hell Yeah. And, at the same time, one must eat.

So, for my clients who are navigating this situation (“It isn’t a Hell Yeah, but I need to eat…”) we often come up with a set of criteria that will make the opportunity worth it. This could involve the structure, the timing, the price, or perhaps a combination of the above. It might mean, for example, proposing a fall versus spring timeline to allow more time to prep. Or, it might involve asking for travel reimbursement to cover the cost of driving to another state.

Will my future self (in 1 month, 6 Months, a year) be happy that I said yes to this? What would my future self want me to say?

This can be one of the most game changing questions for me to ask myself. While my current self will enthusiastically say yes, what about my 6-Month-Future self? Will she still be thrilled about the opportunity?

There's a quote that goes something like, “an elephant looks small in the distance.”

This is also the case with things we say yes to. It might not seem like a lot of time at the moment. But will that still be the case in a month, in 6 months, in a year? Carefully consider the thoughts, the energy, the capacity, and the bandwidth of your future self before your present self says yes to anything.

What would my (actual, or metaphorical) board of directors tell me to do?

Do you have a board of directors? If not, I invite you to create one!

This might be an actual, living board of directors. I have a few different informal boards in my life - some girlfriends and soul sisters, some coaches, some strategic advisors and mentors.

Or, it might be a metaphorical board of directors. The idea is to identify a few people who you respect, put them on your metaphorical board of directors, and then ‘consult’ them when thinking about decisions or opportunities.

Sometimes, during a monthly meet-up with my real-life board of directors, I’ll review opportunities and get feedback. For example, a few months back, I was struggling with a decision not to submit a proposal to speak at a certain conference. They helped me see that while it was a great conference, it was not in line with my vision for the future, and my time and energy would be much better spent elsewhere.

I also have a metaphorical board of directors. These are people who I follow, and whose approach to business I deeply respect. For example, Seth Godin is one of the members of my metaphorical board of directors. He just doesn’t know it! Seth is ruthlessly committed to focusing on his most important work in the world. In his case, that means writing and publishing a blog post every single day. He doesn’t take meetings, he’s very mindful about the amount of travel he takes on, and he is committed to delivering value to his community every single day. If ever I am struggling with what to focus on or whether to take on a new project, I’ll consider what advice he might give me if I were to ask him his opinion. This whole process might sound a little weird but is incredibly helpful for me when I use it.

In the End

At the end of the day, this practice isn’t about saying no more, or saying yes less. Ultimately, it’s about making sure we say yes to the things that are aligned with our values and priorities, and no to the things that aren’t.

Sometimes, of course, we need to do things that aren’t aligned as part of our work, or our job responsibilities, or even basic duties we take on at home. But often, we have more opportunity than we think to shift, tweak, or restructure things to create the alignment that we desire.

Resources and Recommended Reading

  • Essentialism by Greg McKeown - the book I read again and again for inspiration on this subject.

  • The One Thing by Gary Keller and Jay Papasan - I especially like their focusing question: “what is the one thing that will make everything else easier or unnecessary?”

  • Better Than Before by Gretchen Rubin - it was in this book that I first learned about the Four Tendencies. As an obliger, the above practices are essential for me, because my natural tendency is to say yes to external requests and no to requests that I make of myself. Obligers make up the largest percentage of the population; if you find yourself struggling with this topic, you may enjoy checking out her work, or at least her free quiz which only takes a couple minutes.

  • The Four Tendencies by Gretchen Rubin - more information on the four tendencies and how to work with each of them. I’ve found that this framework can be transformative not only for how we operate as individuals, but also how we operate in relationships. Fun fact: Gretchen found that obligers and rebels are often in romantic relationships together, and I’ve found her theory to be correct. Many of my rebel clients are married to obligers; many of my obliger clients are either dating or married to rebels.

Tools I'm Using in the New Year

Tools I'm Using in the New Year

Happy 2019!

With the new year often comes an opportunity to revisit goals, priorities, and intentions for the year ahead; bust out a shiny new planner; or perhaps file away the 2018 notebook and open up a new one for the year ahead.

At any given moment, I typically have a few paper-based tools in rotation for reflection, planning, and capturing notes from meetings and client sessions. In recent weeks, many people have asked for more details about various notebooks, journals, and planners that I’ve mentioned or shared in photos.

So, here is a round-up of the tools I’m using right now.

*Disclaimer: none of these tools are necessary for reflection, visioning, or a happy life. A plain old sheet of paper will also do.

  • The Five Minute Journal - I purchased my first Five Minute Journal several years ago when it first came out. Since, I have purchased many more - for myself, and for others. The idea is simple - 5 minutes per day, to capture a few key aspects of the day. In the morning: gratitude, priorities, and intentions. In the evening: great things that happened throughout the day, and things we could have done differently. The process truly takes only 5 minutes, and I find that this simple practice consistently makes my day better. *Note: many companies have created knock-off versions of this journal, some of which are even called the 5 Minute Journal (talk about things that get my blood boiling!). In these cases, the companies have nearly photocopied the pages of the 5 Minute Journal and created tools that look shockingly similar. If you decide to purchase one, please make sure to get it via the link above, or through the company called Intelligent Change. It is on Amazon, as well - please make sure you get this one (versus the various other knock-off versions that you’ll find when you search - it should be around $24.00, but the price on Amazon has been very funky lately - I would recommend going directly through Intelligent Change if possible).

  • Leuchtturm1917 Notebooks - these notebooks are a bit of an investment, but they are amazing. I previously primarily used Moleskine notebooks, which I still use and love, but the Leuchtturm notebooks are a bit wider, which makes them a perfect fit for someone like me who takes a lot of paper notes and who takes notes that flow all over the page in various, non-linear directions. The company has been around for 100 years, as you may gather from the name, and the details of their notebooks are exceptional - a table of contents at the beginning, numbered pages, and paper that feels oh-so-lovely to write on.

  • Day Designer - this is the paper-based planner I’m using in 2019 and am loving it so far. I still use Google Calendar as my ‘source of truth’ - all of my schedule lives there, and I update it religiously. That said, for the last several years, I’ve found it incredibly helpful and grounding to supplement this with a paper based planner. I use the paper-based planner for morning reflection, to review my morning schedule, and to capture notes and thoughts throughout the day. The Day Designer is intense, and has space to capture most things you could imagine capturing throughout the the day - your schedule, your priorities, and other small things such as gratitude, notes about dinner, or notes about finances. In the past I’ve used the Desire Map Planner, which is also lovely, and decided to switch things up this year.

Okay, those are the 3 main tools in my morning rotation right now! These tools, along with coffee, are my ingredients for a morning that makes me oh-so-happy. For more information on morning routines, you may enjoy checking out these posts:

What about you? Do you incorporate paper-based tools into your daily rhythms?

Manifestation and Action

"Change Your Thinking, Change Your Life."


There’s much in the personal development space about this concept…about the fact that our dream lives are ours to create...about the fact that anything is possible...about hustling, about shining bright, about getting after it, about believing...and about doing all of the other things we see made into nice inspirational quotes, written in calligraphy.

I believe that so much is possible. I believe that changing our thinking and the way we view the world can have a massive impact on how we feel each day. I believe we can create from everything. *And,* I believe that sometimes, in these spaces of motivation and personal development and anything is possible and your dreams are yours to achieve that we sometimes neglect to talk about some of the harder, more complicated parts of this equation. Like the fact that in many ways, even being able to have these conversations and think about these things are privileges themselves.

What can it look like to hold both?

The possibility, and also the reality of what is happening around us?

The invitation to manifest, alongside a commitment to action?

Being positive and optimistic, while not turning a blind eye to the things that are deeply painful in our country and our world right now?

These are questions that don't have quick and easy answers...questions that I feel committed to examining and exploring and that I’ve been leaning into.

What do you think?



How do you prevent the minutia from taking over in everyday life? The laundry to fold, the groceries to pick up, the dog poop in the back yard, the package to drop off at the post office. The schedules to coordinate, the dog sitter to book, the bills to update on auto-pay, the scuffs on the wall to touch up with paint. These things can take over our time, our thoughts, and our conversations if we let them.

I know that these details are part of everyday life. Our life is made up of the moments, after all.

However, as an ENFP, I hate the minutia. I dislike talking about and thinking about logistics. I don’t want to dwell on details.

Instead, I want to dream big. I want to think about projects and possibilities. I want to tap into inspiration and the things that move me. I want to reflect on how we might put a dent in some of the big problems we face  in our world.

And yet, the details exist. The minutia remains. In many cases, we need the details in order to do the projects and have the space and capacity to create from.

What can it look like to have the details taken care of, while creating time and space for dreaming big, thinking ahead to the future, and solving real and important problems? What can it look like to accept and honor the place of the details, but in a way that doesn’t take over? How can we prevent the details and the minutia and the mechanics of everyday life from taking over conversations and thoughts and romances? What can it look like to tap into spirit while still getting the laundry done? To dream big and still empty the dishwasher? To put a positive dent in the world while still picking up the dog poop in the backyard?

This is an ever-present balance I’m trying to hold. I don’t always succeed. And, here are a few things I’m trying.

  • Create time each morning for the big stuff - writing, thinking, reflecting, and dreaming big. While this is something I’ve always done since starting my business, it feels increasingly important as there are more and more logistics than ever with this whole thing that we can summarize as #adulting.

  • Put the logistics into a specific container - a daily scrum, which houses all things that are logistical in nature. Logistics are reserved for the scrum and the scrum only, except in cases of high urgency that require discussion sooner.

  • Outsource. While outsourcing often involves hiring someone to help with the logistical components of life or business, it can also involve doing a trade, or other creative options. Clients have shared creative ways they’ve structured trades for childcare; other friends trade services such as help with yard work in exchange for help with painting. *Note: I recognize that this bullet, in particular, assumes some level of privilege - whether hiring someone, or doing a trade. It assumes that we have some level of discretion with our money and our time.

  • Hold the logistics lightly. It’s easy to let the logistics and the minutia take over if we let them. And, at the end of the day, there’s fluidity with most of them. It doesn’t really matter all that much if we empty the dishwasher at night or in the morning; if we get all of the laundry done before we leave the house or if we save some for later; if the package gets to the post office on Friday rather than today.

What about you? What are some of the ways that you allow the details and the logistics and the minutia to be taken care of, without taking over entirely? I’d love to hear your thoughts.

The Calendar Habits that are Currently Changing My Life

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A Simpler Time. Simplifying. Simplicity.

Themes of conversations I’ve been having a lot of with clients and friends over the past couple weeks. As we are building successful businesses and making more money and having more impact and growing in our careers, how can we stop and remember…

What’s it all about?

What really matters?

How can we go through our days and our weeks and our lives feeling free?

How can we simplify?

While I’m all for some life-changing magic of tidying up, I find that my own feelings of simplicity and freedom have more to do with my calendar and how I’m spending my time than how I’m folding my sweaters. For me, when my calendar feels out of control, my life feels out of control. And when my calendar feels aligned, my life feels more aligned.

As a result, my relationship with my calendar has been a constant work in progress. Since starting my business, I find myself unintentionally repeating some of the habits I learned in the corporate world - back to back meetings, double and triple booking myself, and packing my day with commitments from 7 am until 6 pm. Changing these habits is still a work in progress for me, even after running my business for over five years.

In recent months, I’ve been looking more closely than ever at the calendar habits that create more simplicity in my the practices that make me feel more free...and that ultimately allow me to have more positive impact by focusing on the things that matter most. Here they are.

Do a 2-Week Look Ahead, Each Week.

This has been the most transformative process I’ve implemented recently (credit for this practice goes to Jake). Each Sunday or Monday, Jake and I sit down with our calendars, and look out at the next two weeks. What do we have going on? What shared commitments do we have? What logistical considerations do we need to think about for the weeks ahead? And what shared time do we want to block off to hang out, have dinner with friends, or take the pup to the dog park?

While I’ve been in a solid rhythm of doing my own weekly review for the past several months (which I also love), the process of the shared look-ahead has not only made my life feel simpler, but it’s helped to create shared accountability for non-work-related things that we want to prioritize. I can’t recommend this process enough.

Create White Space.

Schedule at least 30 minutes of white space (ideally more, when possible) each day to “zoom up” from the whirlwind and think critically about the things that matter most. To increase your odds of maximizing this time, make a note about what you want to focus on. For example - do you want to use this time to identify key priorities for the week ahead? Do you want to use it to connect with a client who you haven’t talked to in awhile? Or do you want to use it for quiet thinking and reflection? Schedule the block on your calendar, along with a note about its purpose.

Schedule Meeting-Free Time.

Reserve a half-day free of meetings once per week, to focus on strategic work and big picture projects. If you are part of a team, I recommend implementing this practice as a team. Collectively identify a block each week that could be free of internal meetings, and create an agreement to preserve that block.

Several of my clients have done this by creating a block of time each week that is free from internal meetings, and it has increased both the happiness and the overall impact of the team, by giving each team member a sacred block of time for heads down work each week.

Be Specific.

Be as specific as possible about what is happening within each calendar block, to increase the likelihood of it happening. For example, instead of relying on a recurring calendar hold that says “focus time,” add specific details about how you want to use your focus time during your 2-week look ahead. Otherwise, it’s very easy to allow this time to be overtaken by meetings or lower impact work.

Look Critically at Meetings.

Think critically about which meetings you need to be a part of. Ask, “what specific impact can I have in this meeting?” If you’re not sure, have a conversation about whether it really makes sense to attend. If you lead or manage others, have this conversation with your team members. How does the team feel about the effectiveness and relevance of weekly and monthly meetings? Are the meetings serving the overall purpose of the team, and the organization? Are there any changes that need to be made? The 2015 State of Enterprise Work Survey found that “wasteful meetings” were employees’ top obstacle to getting work done. Improve your approach to meetings as a way to improve your overall outcomes.

Be Realistic.

Schedule buffer time after meetings that often run long. If there are certain client conversations that always take longer than the scheduled hour-long block, add a 30-minute block to your calendar after each of these meetings so you can plan for the overage. Plan ahead so that you can feel prepared, rather than feeling as though you’re constantly running behind.

Add commute time and meeting transition time to your calendar - and base this on the “worst possible scenario” (lots of traffic, lots of red lights, seeing several colleagues in the hallway) versus “best possible scenario” (no traffic, all green lights, and seeing no other humans on the way).

Schedule Personal Commitments.

Add personal items - even small ones, like going to the grocery store - to your calendar so that you can plan for them as part of your day, rather than trying to “squeeze them in” to an already-packed calendar. As part of your 2-week look ahead, think about all of the priorities in your life - especially the priorities that span beyond work and client commitments - and the ways that you want to honor these priorities over the course of the upcoming two weeks.

Peter Drucker once said, “what gets measured gets managed.” For many of us, our calendar is a measure of how we spend our time. Being intentional about our calendar allows us to be intentional about our days, our weeks, and our lives.

“How we spend our days is how we spend our lives.” - Annie Dillard