Lessons learned from feeling stupid

For a period in my life, I spent a lot of time in close proximity with folks who generally left me feeling… stupid.

Maya Angelou once said that people don’t remember what you say or do but remember how you made them feel. As I think back to that time, I do remember many of the things that were said and done. But, I have incredibly vivid memories of how I felt.

The interesting thing about that time is that the more I felt stupid, the more likely I was to make stupid mistakes. And I did make more than a few. It was a self-perpetuating cycle.

I learned three lessons from those times.

First, I learnt to pay close attention to how I felt after I experienced people or things. There are times when some experiences don’t feel right. And, when it doesn’t, I ignore any and all attempts at logical thought and stay away. Feelings – especially those that originate in our gut – matter.

Second, I learnt to value people who appreciate what’s good about me over my flaws. Their feedback consistently focused on helping me improve my strengths while ensuring my flaws didn’t get in the way. It was generally constructive. In my experience, that is the most useful kind of feedback.

That is not to say critical people aren’t helpful or caring. In many cases, they might be one or both of those. That said, every once a while, these relationships just end up perpetuating a bully-victim cycle. In some cases, these critics inspire tremendous wealth/power/fame by virtue of ensuring we operate with a consistent sense of insecurity and a chip on our shoulder that never goes away.

That may be an acceptable trade-off for some. But, it isn’t for me.

Third, as a result of paying attention to feelings and valuing constructive, I have gravitated to environments where people I respect operate intensely to make a positive impact on the world – in the presence of safety and belonging.

That safety and belonging, in turn, inspires the kind of confidence that enables us to operate from a place of wholeness instead of our wounds. And, in places where people operate from wholeness, people leave feeling better about themselves than before more often than not.

They may (and likely will) often be faced with the realization that they have a lot to learn. They may not want to do so and might decide to leave.

But, they’ll never be made to feel consistently stupid.

And, that’s an outcome that matters a lot to me.

Executive communication – meetings, speaking, and writing

In conversations about executive communication, being invited to and then getting air/speaking time in meetings is consistently overrated.

And, on the flip side, writing insightful documents/updates and being responsive + concise over email is consistently underrated.

Talking provides more instant gratification than writing. But, often with significantly lesser long term impact. :-)

I’m not as…

It’s easy to get caught up in self-talk along the lines of – “I’m not as smart/articulate/strategic/insert-your-favorite-aspirational-word as <insert benchmark>.”

This post isn’t about avoiding comparisons however.

If you can, you should definitely do so.

It just isn’t easy.

Another approach to tackling this problem is to just habitually add a line every time we hear ourselves saying so. In this version, we’d say – “I’m not as brilliant as person X. But, I’m me. And I’m enough.”

That turns out to be true 100% of the time.

Stoic notes – part II

In Stoic notes – part I, I shared 3 themes and accompanying reflections from my experience reading stoic philosophy.

I took another pass at synthesizing it recently. My hope was to bring the longer set of notes down to a list of 3-5 notes I could read at the start of every day. Below is that list.


1. Think about 3 amazing things you have that you will sorely miss. Remember the awesome power of luck in your life and don’t underestimate its ability to take what it has given. 

Then, give thanks for the riches you have – the riches that come from having enough.

2. Don’t chase fame or wealth. Both are fickle and move us further away from tranquility. Focus instead on virtues that matter to you and the game you are playing. Success – as you define it – ensues. 

3. Focus on what you control – keep laser focused on direction and process over short-term outcomes. Macro patience, micro speed.

4. Welcome minor discomforts – cold, hunger, and the pain that comes from stretching mentally or physically. Reach for those discomforts everyday by spending time in depth, exercising, reading, listening, and eating right.

5. You never know if a good day is a good day. It’s never as good or bad as it seems. The universe is unfolding as it should and we’re existential specks anyway. So, keep a sense of humor and keep plugging away.


To me, these get to the heart of stoicism – the ability to remove negative responses while enjoying the positive. I’m hopeful the act of recommitting to them every day will help me get better at living them.

In time.

Stoic notes – part I

In the first 3 months of the year, I read 3.5 books on stoic philosophy. After “A Guide to the Good Life” by William Irvine (Stoicism 101), I made my way through Seneca’s “Letter from a Stoic” and Marcus Aurelius’ “Meditations.” I read about half of Epictetus’ “Enchiridon” before stopping – it didn’t work for me.

As I was reading these books, I wrote down a series of reflections. On some occasions, they were directly from the books. On others, the books reminded me of a note from elsewhere (often from Stephen Covey’s “7 Habits”).

I then synthesized it into 3 themes that represented what stoicism stood for in my mind.


I. Let perspective and joy flow from hyper gratitude
The poor person isn’t the one who has little. It is the one who craves the most.
Spend no time today contemplating what you don’t have. Think instead of the amazing things you do have.. and imagine how bad it might be if those were taken away.

Remember that we’re living a life that our ancestors could only dream of.. and that you dreamt of. There’s magic around us!

Cities and civilizations take years to build and moments to fall. Fortune and nature have their way in the end. Remember the awesome power of luck in your life and don’t underestimate its ability to take what it has given.

“When I look upon the tombs of the great, every emotion of envy dies in me; when I read the epitaphs of the beautiful, every inordinate desire goes out; when I meet with the grief of parents upon a tombstone, my heart melts with compassion; when I see the tombs of the parents themselves, I consider the vanity of grieving for those whom we must quickly follow; when I see kings lying by those who deposed them, when I consider rival wits placed side by side, or the men that divided the world with their contests and disputes, I reflect with sorrow and astonishment on the little competitions, factions, and debates of mankind.”

Let molehills be molehills. If it isn’t going to matter in 5 years, don’t let it take much of your attention.

What if we died today? How would that change how we did the small things?

Celebrate the life of those who’ve passed. Don’t let that take away focus from those around you.

II. With perspective, replace negative emotions with grace

Blame is pointless.

Keep a sense of humor – especially when you feel you are insulted or offended or provoked.

Keep counsel in silence when you are angry. Don’t fight fire with fire. Remember the fire department only uses water.

To be able to bear a perceived misfortune is good fortune. Our misfortunes aren’t worth dwelling on. The world will move on without us. Time will move on…

Wish for events to unfold as they’re unfolding – and not as you desire it. And you’ll never feel you don’t have enough. :)

What counts is not the fall. It is the bounce back.

III. Focus on the process by playing the infinite game

Focus on what you control – keep laser focused on process over outcomes.

Macro patience, micro speed. Today matters.

Let our velocity show in the conversations we say yes to and the comments we choose to make. Let it not show in our hurry to get a word in.

Be a light, not a judge. Let your actions speak. We are what we do.

Do not fear mistakes. Fear only the absence of a creative, constructive, and corrective response.

Welcome minor discomforts – cold, hunger, and the pain that comes from stretching mentally or physically.

Spend time with people who help you learn and provide you positive energy.

Treat everyone how you’d treat your bosses.

Spend time in depth. Instead of reaching for a feed, reach for a book.

Meditate/reflect about the day at the end of the day. Think about whether you lived as you intended and about what you learnt.

You never know if a good day is a good day. It’s never as good or bad as it seems. The universe is unfolding as it should.

Don’t chase fame or wealth. Both are fickle and move us further away from tranquility. Focus instead on virtues that matter to you and the game you are playing. Success – as you define it – ensues.


For a few weeks, I read all these notes every morning as a daily reminder. But, this list turned out to be too long. So, I sought to synthesize all of this into 3-5 notes that I could could read and commit to everyday.

I will follow up with that list in tomorrow’s post.

Silenzio Bruno

There’s a scene in Pixar’s most recent movie – Luca – where Luca’s best friend attempts to convince him to take a leap of faith.

See the source image

Alberto – the friend – explains to Luca that he’s got a “Bruno” in his head. Bruno is that nagging voice that tells him he can’t do it.

So, he asks Luca to scream “Silenzio Bruno.” (Shut up, Bruno!)

A few Silenzio Bruno’s later, Luca musters enough confidence to take the leap.

It is a fun scene and one that led to a conversation with our kids about taking action despite our fears. We agreed to try Silenzio Bruno the next time we’re faced with a scary slide, for example.

I look forward to trying it out as well and doing a better job of “firing the crow.”

Skechers and shoe hacks

For years, I had a routine every time I bought a shoe. I would spend a bit of time upfront tying my laces to meet 2 objectives. It had to be (a) tight enough so it wouldn’t come off and (b) loose enough so I could just slip my feet in and out.

Once this was done right, those laces would stay that way for months – sometimes years.

Then, a few years ago, my wife introduced me to Skechers. Skechers shoes are built on exactly that premise – no laces, slip in and slip out easily.

It was a magical experience. One of those “Where have you been all my life?” situations.

See the source image

I think about that moment when I slip into my Skechers from time to time. We often hack together solutions to solve problems. And, it is always magical when we find a product that is designed to solve that exact problem.

Finding those problems is simultaneously the most important and hardest part of anyone seeking to build products for a living.

Being constructive

Early in our marriage, we put up a list of 3 family values on a whiteboard. The third value on the list was “be constructive.”

We’ve moved homes a few times since and evolved our thinking on values (preferring virtues instead). But, that idea – “be constructive” – is one we’ve talked about many times over the years.

It happened again recently. As we were reflecting on reactions to a few recent decisions that we’d shared with folks we knew, we found ourselves – once again – appreciating the power of being constructive.

To be constructive means to build up. Folks who learn to be constructive focus on the facts at hand and work on building the most positive reality they can. And, as optimism is a self-fulfilling prophecy, their energy often helps in creating that reality.

It is the equivalent of the “Yes and” rule in improv. There is no time for “buts” as we construct the next scene.

We aren’t born with the ability to be constructive. It is a skill. And, like all skills, it is result of training our muscles and building in the habit into how we operate.

I hope to train these muscles a lot more in the coming months.

Potential for remote work

The McKinsey Global Institute shared an interesting chart analyzing the potential for remote work within various economies.

As with such analyses, the absolute numbers matter less than the trend.

In the US, MGI estimates ~40% of work can be done hybrid or fully remote. Software/technology, for example, falls squarely within this 40%.

We are still in day 1 of figuring out what the office looks like post COVID-19. Most technology companies are expected to share updated guidance for what they expect over the summer.

A couple weeks ago, I polled about 50 colleagues on one day about how often they expect to be in the office. Nearly every one of them said either 2 or 3 to meet colleagues in person. No one expected to be back 5 days a week again.

For industries like technology, I expect some form of hybrid work to be the norm. Once a few big companies make it the norm, it will be hard for others to require employees to come in 5 days a week.

There will always be exceptions. More companies will be remote than before.

But, if this pandemic results in a change in the default from on-site work to hybrid work, that will be a meaningful change indeed.