Thoughts & Observations

Maps Not Measuring Sticks


It’s an interesting exercise to sit down and add up all of the things you think you should be doing every day and see how much time doing all of those things would actually take.

I would like to bet that meditating, blogging, journaling, reading, visualizing your day, gratitude-listing, cooking and eating healthy meals, taking your vitamins, exercising, brushing and flossing, handwriting thank you notes, never lunching alone, calling your mom, and oh right, also putting in a full day of work, taking care of family, and getting the 7 to 8 hours of sleep we are supposed to get for most people will simply not fit in a 24-hour time span.

And yet if you read articles like “5 Things Super Successful People Do Before 8 a.m.” you might walk away feeling like there’s something wrong with you if you can’t fit in half of that list before 8 o’clock in the morning.

Every time a new article comes out telling you why writing every day is good for you or that you’ll be happier if you [fill in the blank], it is difficult to not feel compelled to add those things to the list of expectations that you have for yourself and then feel disappointed in yourself when you somehow can’t magically fit 30 hours of activity into 24.

Part of that disappointment comes from the fact that we assume that if other people are sharing this advice with us, they must have somehow figured out a way to follow all of it.

Advice meant as a map to help us on our journey, we end up treating as a measuring stick of our own abilities and potential.

We have been storytelling and map-making for centuries as a way to help the next people after us find their way, getting through their journeys with fewer trials and tribulations.

Without maps we’d spend our days wandering around constantly having to discover and rediscover the same things over and over again, staying longer in the same spot instead of making forward progress.

But a map is most useful when it shows you all of the potential paths, not just one way to go.

The internet has been a boon for the sharing of wisdom, roadmaps, and advice, but it has also created a whole marketplace for the sharing of what appears to be a single correct route to success. Advice on hacking our lives toward better performance and productivity and happiness is the dieting advice of this decade.

And just like dieting advice, it can often feel prescriptive and closed, instead of something that is exploratory and open.

So we have to bring the exploration and openness back to it.

We can shift from seeing an article about how early risers are more successful as a dictatorial decree (no matter how the headline is written) to seeing it is an invitation for us to explore, to keep our own curiosity about ourselves alive, and to check in with ourselves about how intentional we are being about what we do with our time and how our current habits are working for us.

If you find that when you sleep until 8 or 9 a.m. you always wake up feeling behind and feeling that you have to rush through your day, then waking up earlier could be good for you. Not because it checks off the “waking up early” box, but because it could make you feel better.

But only you know that.

All of these suggestions give us an opportunity to check ourselves, to check what we “know,” to check the assumptions we’ve made about what we can and can’t do. If in the back of our minds we’ve always wanted to write but keep telling ourselves we don’t have time, is that really true? How important is that to us? If it’s that important why aren’t we finding even ten minutes a day to do it?

At its best, the wisdom and experience of others leads you to ask yourself important questions that help you, in turn, develop deeper wisdom about yourself.

It is a map with multiple routes. A choose your own adventure with wise hints along the way.



Thoughts & Observations

Updating My Definition

We’re still very young when we start making our first decisions about who we are…and who we aren’t.

In middle school bad asthma meant that I always had a doctor’s note to walk what was supposed to be a nine minute run…and I therefore determined that I wasn’t a runner.

In high school my first ever C+ came in pre-calculus where the teacher concentrated his teaching only on the kids who got it instantly…and I therefore determined that I wasn’t really a math person (or a science person or a computer science person for that matter).

In college and in my early twenties when the only thing I could cook was spaghetti, I determined that I wasn’t a cook.

These definitions – just like saying we are a person who doesn’t like tomatoes, or who likes milk chocolate better than dark chocolate, or who likes jazz better than classical – give us short cuts for how to navigate the world. They mean we don’t have to make decisions from scratch all of the time because we’ve made that choice before and we know what our usual answer is.

But I think we sometimes make the mistake of believing that each of those choices add up to “who we are” at our core. That we are the sum of our preference for jazz over classical and dogs over cats.

The challenge with that is that it doesn’t leave much room for change, or take into account the fact that we are someone from the moment we are born. We have a “who we are” in place from our first seconds here on earth. The “who” does not rely on the definitions we later add of ourselves to exist.

As we grow up we find definitions comforting because they help explain us to ourselves and to the world, and they connect us to a tribe. If you’re introvert wondering why you are experiencing the world in such a seemingly different way, finding the definition of introversion and connecting with others who experience the world in a similar way provides a tremendous sense of relief.

But we can very quickly move to a place where those definitions start pre-defining our future selves and determining how we move through the world.

If introverts aren’t supposed to like or be able to “handle” big, schmoozy parties with strangers for instance, they may find themselves preemptively turning down party invitations, even if they actually feel like hanging out, because going does not fit the definition of themselves they feel compelled to fulfill.

If you decided 15 or 20 years ago that you are not a cook, or not a math person, or not a runner, it impacts how you approach the world now.

And it has been fascinating to discover that I am still carrying around those definitions of myself, even with my asthma long gone, years of organizational financial management on my resume, and consistently satisfied people sitting around our dinner table.

So I’ve decided to start challenging and updating those definitions even further. I’ve asked someone to help me learn to run, someone else to help me learn to code, and I’ve signed up to with a program to help me become a better cook.

My middle school, high school, and college self won’t recognize these new definitions. And that’s a good thing.

Thoughts & Observations

A Lesson from Beans


In the past, I have tended to be a baker and not a cook, following recipes instead of improvising.

For a dinner recently though, I decided to cook Korean-style black beans to go with our dinner, a dish I had never made before.

I followed the recipe as it was written, making sure that when I pulled the beans off the stove, they were neither too hard nor too soft as the recipe noted.

They tasted a bit underdone to me and weren’t as flavorful as I would have liked, but I thought to myself “well, but that’s what the recipe said to do, so they must be ok.”

A quick taste by a friend confirmed that they seemed underdone and needed more seasoning.

I felt torn for a minute because I had followed the recipe and didn’t want to deviate from that and have them come out “wrong.”

But then it occurred to me that it didn’t matter at that point what the recipe said.

If I didn’t like how they tasted – if I thought they were underdone and underseasoned – that was all the evidence I needed.

“Wrong” in this case was determined by having them not taste very good, not whether I had followed the recipe.

The person who wrote the recipe wasn’t going to show up and taste what I did and knock points off for my beans not being by the book.

I put the beans back on the stove and added more soy sauce.

As I ate the much better beans a bit later, I thought about the role that recipes and intuition play in our lives.

It makes sense, in  many cases and especially in the early stages of our life, to follow recipes, instructions, and the advice of others.

When we’re young, those who are older, wiser, and more experienced can often give us invaluable insight that sets us in the right direction.

As we grow older, the challenge then becomes balancing that guidance with listening to our own common sense and intuition.

So much of our lives are built around following rules and having people tell us how to figure things out, that we often come to believe that we do not have the natural capacity for making certain determinations on our own.

But we all innately have intuition and problem solving capacity.

What we really have to do is learn to trust it.

Thoughts & Observations

A Modern Plea from 1817



The slogan “8 Hours Labour, 8 Hours Recreation, 8 Hours Rest” isn’t a modern plea to bring about a more humane work schedule.

It’s a plea from 1817.

A plea almost 200 years old.

At the time, we eventually got what we asked for in the form of a 40-hour work week.

Fast forward a couple hundred years and now technology enables us to work wherever and whenever we want (an advancement that like most others has a light side and a dark side) and we seem to have forgotten the key rule of human functioning: in order to produce our best work, we have to balance that work with rest.

This became a cause worth picketing for in 1817 because people were being asked to work 12 to 16 hour days, six days a week. It was seen as inhumane.

Fascinating how history repeats itself.

And yet this time exactly who are we going to picket?

Yes, sometimes it’s the company you work for who is setting inhumane work expectations.

But more often than not the person you would be picketing is…you.

Thoughts & Observations

The Cost of Doing Business

As we work and build businesses, we are constantly subtly aware of the consistent trade offs we are making.

A late night of emailing means not getting up early and going to the gym.

Running from activity to activity means that we don’t call our parents as often as we should.

Viewed individually these instances seem minor and they come with built in excuses for why the trade off is essential for whatever it is we are are trying to achieve in our grand master plan (it’s ok if we don’t call our parents now because we’re working on something that will make everything better or make us rich and we’ll be able to call them twice or three times a week even instead of just once…as soon as we accomplish this goal…or at least get our inbox to zero).

At the organizational level too, we tend to view these types of things in their silos and not as part of a bigger picture.

You see the fact that you, as the CEO of a company, never take vacation, as a single, individual decision, not as a decision that impacts how the entire organization views the importance of vacation.

You see the fact that your employees will sleep at their desks for you while they pull all-nighters to get a project done as a sign of loyalty, not as the sign of a problem.

Viewed as individual instances, all of the trade offs seem minor and time-limited.

But when we view them collectively across time, we begin to see patterns of collateral damage emerge.

For individuals, that collateral damage often takes the shape of physical and mental health problems and lost or damaged relationships.

For companies, that collateral damage can be seen internally in high turnover, low engagement, low productivity, and often miserable employees.

We have accepted much of this collateral damage as the cost of doing business.

We resign ourselves to the fact that this is how it must be.

And while we can individually make different personal choices, we won’t see deeper systemic change until we start asking companies to take on some of the responsibility for setting a new standard, for deciding that the collateral damage isn’t worth it.

I see one of the biggest business challenges of our time as answering the question of how we can achieve our full potential and achieve success both as individuals and as businesses without leaving so much collateral damage in our wake. 

Thoughts & Observations

Time Problem or Mind Problem?


We often confuse mind problems with time problems.

When we skip meditating in the morning or skip going to the gym, we say it’s because we didn’t have time.

When we don’t get started on the big project because we were busy rearranging our files, we say it’s because we didn’t time.

What we are really saying is that something else was more important or felt better to us in the moment.

The little dopamine hit we got from checking emails was more important.

The slight relief from our “fear of missing out” anxiety we got from checking Facebook was more important.

We don’t always feel like we’re tricking ourselves because we have been unconsciously working to prove our own time problem: we spend time on lots to things to ensure that we don’t have time to do the things we are avoiding doing for one reason or another.

We can choose to make time for just about anything, and if we’re wondering why we never seem to be able to make time for the things we say matter most to us, it might be time to stop looking at the clock for answers.

99% of the time we don’t have a time problem, we have a mind problem.

Thoughts & Observations

External Optimist Internal Pessimist


Researcher and author Martin Seligman has years of experience gauging whether someone is an optimist or a pessimist based on their word choice. He has done this with everyone from politicians giving campaign trail speeches to baseball players explaining a win or a loss.

And while a trained researcher can clearly detect the difference between the speech of an optimist and the speech of a pessimist, there are many people who have learned the art of seeming hopeful and optimistic on the outside, but being incredible pessimists on the inside.

They fall into the category I call “external optimist internal pessimist.”

When something goes wrong for someone else, the external optimist internal pessimist might comfort them by saying things like: “It’s not your fault.” “When one door closes, another one opens.” “You are amazing. You will totally pull through this.”

But when it comes to how they talk to themselves, they don’t use such supportive, optimistic language at all.

When something goes wrong for the external optimist internal pessimist, they explain it to themselves using language that is, using Seligman’s terminology, personal, pervasive, and permanent: “You’re so weak. You can’t finish anything.” “You never reach the goals you set for yourself.” “You’re horrible at sales. Other people could do this so much better than you. You’re never going to be successful at this.”

External optimist internal pessimists can even trick themselves into thinking that they have a completely optimistic worldview because they constantly hear themselves saying positive things to others.

But they are often not so carefully listening to what they say to themselves.

And while what we say to others and what others say to us is important, the voice that we hear most frequently inside our heads is our own. If that voice is one of constant pessimistic berating, we are more likely to become depressed, withdraw, and even shorten our lives.

The answer isn’t to adopt a stance of false optimism. If you are a pessimist, it means you are also usually a realist, so tricking yourself into feeling positive by reciting “I am wonderful”-style affirmations in front of a mirror probably won’t work.

But what Seligman and others have found does work is listening to yourself more, catching yourself when you slip into pessimistic explanations, and challenging yourself to find alternative explanations. Instead of taking one missed sale as an indication that you are a bad sales person, could it be that the client simply wasn’t the right fit? Or maybe you were tired and didn’t give the pitch fully? Or maybe the way you talk about the product needs to be updated?

Walk through it the way you would with a person you love and care about, except this time that person is you.