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Here’s why it’s so hard. Because as human, we are outcome-driven. And the thing about questioning and planning is that it is less about outcomes than it is about avoiding mis-steps.

So, the easy-hard part is to make a million dollars. The hard part is to stop after you made a million dollars. And the hard-hard part is to ask why a million dollars will bring you everlasting happiness.


We have seen celebrities like Ellen and many other coming out, gathering millions of fans in the process. 

Our culture has benefited from the courage of people such as Gandhi, Rosa Parks and Nelson Mandela.  

Yet, we are at the dark corner wrestling if we should tell our loved one the truth. Creating multiple threads in our mind, to make sure that we don’t hurt them, and in turn, hurt ourselves. 

Why is vulnerability so difficult, yet so useful?

Because the best kind of vulnerability takes work. The work to accept yourself with all your truth. The work to find and cultivate a tiny group of fellow travellers. The work to earn the privilege to share your story, in a way, that others can relate. The work to see the fear of others, and in return, be seen. 

So no, being vulnerable to your parents (in one sitting) is not a good idea. Sharing your truth that might get you hurt is not either.

There is a stepping stone to being vulnerable. There are skills to learn, trust to build, and courage to gather. You rush it and you’ll slip. 

  • Non-violent communication
  • Telling your story
  • Conflict resolution and issue identification 
  • Giving and asking feedback

Slowly but surely. It begins with accepting that this takes work. And it might be worth it. 


I have no idea what it’s like to be pregnant. 

And for the most part, I have no idea what’s it like to have cancer, or to have my parents die in front of me. 

Perhaps the worst thing we can say to someone in that moment is the truth. Our truth, that “everything is going to be okay.” Because it is not okay, at least not for them. 

In that moment of an instance, our good intentions can cause pain and suffering. And what’s worse? We’ve closed the door to actually allowing  someone to ask for help and making it difficult for us to learn what they might actually need. 

We’re not wired to walk in someone else’s shoes. It’s not our first instinct. So when we extend our heart and our feelings to another, when we imagine what it must be like to be them, we expose ourselves to risk. The risk of feeling bruised, or of losing our ability to see the world from just one certain point of view.

It’s easier to walk on by, to compartmentalise, and to isolate ourselves.

Or we can begin with this… “I’m so sorry. I cannot imagine how it’s like for you and it must be really difficult. I just want to let you know that I’m here. I am here for you.”

Show up with our presence and empathy, keeping our judgement and clever solutions to ourselves. 

Pray that one day they will come to terms with reality, a friend by their side. It’s difficult, but it’s precisely what someone might need from you. 


The thing about coincidence is that human beings love it.

We notice something interesting, then create an explanation, and that becomes part of us.

You found someone who listens to an unknown artist that your grandfather loves, and that you love too. And maybe just maybe, both of you have the exact same birthday.

What are the odds! “This must be him. I’m in love.”

It turns out that if I put 25 people into a room, there is more than a 50% chance that 2 people have the same exact birthday.

What are the odds! Well, 50%.

Here’s why you need to worry about coincidence: human beings want explanations, even for totally random events. So we make up stories, then we believe those stories.

So it’s no secret that scientist doesn’t believe every explanation that is thrown at them. They are skeptic precisely because they know that it’s easy for them to lie to themselves.

Richard Feynman, the scientist of scientists, famously said, “You should never, ever fool anybody and you are the easiest person to fool.”

So they go a step further and try hard to falsify their own theory. And even then, they still get it wrong. Remember the days where we are told to eat more bread?

I begin with this. Coincidences are real, and coincidences don’t matter. Coincidences make a good love story, but it might not be a good reason to sign on the dotted line.


Civil servants are getting their lowest bonus since 2009. And they are not happy. 

Of course, they are not happy. Diligent and smart as they are compared to the previous year (or perhaps more), they are getting a pay cut.  

The message comes through, loud and clear. “No matter how hard I work, it would not move the needle. The organization is too big and my work don’t matter”. 

Perhaps (you think that) anyone should just be happy receiving any bonus at all. But after getting an extra cheque for the last 10 years, it’s easy to get used to it. 

So, it’s not hard to extrapolate that and do the bare minimum. Get paid, go home and get on with life. The life of the “iron rice bowl”.

Consider PayPal Fraud Prevention department. It costs a financial institution a lot of money when fraudulent charges are made, because they often have to eat the cost. So this department works to make the number of fraudulent charges go down at the same time keeping expenses low. Which sounds great until you realise that the easiest way to do this is to flag false positives, and provide little or no fallback when a mistake is made. Stories of good (or great) customers being totally shut down, sometimes to the point of bankruptcy, are legion. There may be people at Paypal who care about this, but the security people don’t. That’s because they’re not measuring the right thing.

And this department has no incentive to fix this interaction, because ‘annoying’ is not a metric that the bosses have decided to measure. Someone is busy watching one number, but it’s the wrong one.

As any organization grows and industrializes, it’s tempting to simplify things for the whole. Find a goal, make it a number and incentive it until it gets better. 

Here’s an experiment. Write an alternative bonus scheme that measures the things that people can impact with their individual effort. For recruiting, it could be the percentage of offers accepted. For engineering, it could be the percentage of tickets closed. Present the 2 bonus scheme (old and new) for new hires to choose. Measure the difference in productivity – soon the increase in productivity will pay for itself.

Incentives are superpowers. Unless you’re busy rewarding the wrong things – measuring what’s easy to measure as opposed to what’s important. 

(And if you’re working in the organisation where you care, take this article, gather a group and talk about it. Because real change starts only from the people who care, doing work that matters.) 


My 2019 Retrospective

We spent most of our lives making money, and once we have enough, a new chapter of life begins.

“First, you get rich. Then, you get healthy. And lastly, you get peace.”

This year, I arrived at making enough. I found an equilibrium between my income and my desires. Now, I choose the job I want, with people I enjoy, when I want. And the ability to fire clients that I don’t enjoy working with.

This is by no means that I am wealthy or that I am flying business class. But neither do I want to.

“People living far below their means enjoy a freedom that people busy upgrading their lifestyles just can’t fathom."


(Previous retrospective: 2018)

What’s a retrospective?

A retrospective is when you look back on past events to identify what worked…and what didn’t work. A retrospective helps you celebrate your wins and identify your weaknesses. It helps you learn from the past and correct for the future.

How to do your own personal retrospective

To do a personal retrospective, you simply pick a particular project or time period and ask yourself the following questions:

  • What’s working? (“What did I do right? What am I proud of?”)
  • What’s not working? (“What could be improved? What are my biggest opportunities for growth?”)
  • How can I fix what’s not working for a better result? (“What specific things can I focus on next time?”)

Then you spend 15-30 minutes writing about each.

Bryan's 2019 Personal Retrospective


I found my stride in finances (And come to terms with the end state of my animation studio).​

  • I gave up growing Sage Animation. The business fulfilled it’s purpose for me to work remotely and get paid (enough) to explore other things. I learned that to grow the business (financially), the business become worse, losing it’s competitive advantage.
      • Created animation for big brandsOCBC, Epson and DHL.
      • Got on Google page 1 for most relevant keywords
      • 80% of sales are inbound through the web or referrals.
  • I saved my first $100K. And started an investment portfolio (retuning 12% since Feb 19′) using Ray Dalio’s All Weather portfolio.
  • I started contributing to my parents ($500 a month).

I started to explore what is art for myself (and what is the next project to take on).

I put work in searching and deepening relationships that I enjoy (And explored what I want in a romantic relationship).

  • I developed skills to make friends. I read books and took $2,000 online course (People School).
  • I host a monthly Documentary night to connect with friends.
  • I scheduled a giving hour every week where I give back to friends and people who I recently met.
    I explored what I want in a romantic relationship. (In defence of Junk Dating) I went on 35 dates – some didn’t worked and some became friends. I have learnt a lot here and will write more about this soon.
  • I checked-in to family therapy with my parent. We’ve been doing a monthly dinner but it doesn’t seem to move the needle. I’m very hopeful. More on that soon.
  • I fired a co-worker poorly. I reflected and wrote about it different: How to Fire People.

I doubled down on my physical health.

  • I got into the best shape of my adult life, from 86kg 73kg now. I wrote about it here:  Tools for Weight Loss.
    • I kicked the night snacking habit.
    • I prep delicious and healthy food weekly.
    • I kept the weight of 73kg for 3 months now.
  • I (might) have figured out the wrist issue – it’s a auto-immune condition, Spondyloarthritis (which can be keep at bay with modern medicine)
  • I adopted a daily movement practice (The Happy Body). It’s like yoga with weight. I do it every morning (even while traveling), and I feel better, every time.
  • I went on the Happy Body retreat in New York and got to meet the creator of the program, Aniela and Jerzy Gregorek. Bonus: I got to met Tim Ferriss (and passed him a thank-you note).


I need to get better with the relationship with my mum.

As I developed different interests and life philosophy, it diverges from my parents. This has cause us to drift apart, and without the emotional surplus of shared activities. We get into fights over small things. I find myself getting triggered, and am unable to give patience and empathy. 

I need to get to a reliable solution to the back and wrist issue.

The arthritis medication seems to work, but it’s not 100%. I still get wrist or back pain from time to time, which affects plans I made. I also can’t carry weight which hinders the improvement on my flexibility.

I need to develop a better framework for choosing projects.

As I’ve decided to stop growing the animation studio, it has freed up a lot of time. I came up with many options & ideas, but instead of picking one, I am stuck with the paradox of choice.


Action steps #1: visit a family therapist

Rationale: I’ve already tried to schedule in monthly dinner to hash out difficult topics. But the result are subpar. Two things, I think it’s the problem with the  messenger (me), not the message and I don’t know the process enough to lead. 

Action steps #2: track the days of the wrist pain (and find correlation)

Rationale: I can’t remember things accurately. And creating hypnosis out from bad data will cost more time than investing in a set of accurate data.

Action steps #3: create a decision matrix to evaluate projects

Rationale: Usually, I pick the project that I’m most excited about in the moment. This strategy leave me with many unfinished projects, as I hop from one to the other. A decision matrix would help in choosing, committing and finishing projects.

Well, that’s mine 2019. Now, what about you? What do you think is your biggest accomplishment last year? And what are areas that you would like to get better?

Send me a link if you ever got down to it. 

Work as hard as you can. Even though who you work with and what you work on are more important than how hard you work.


Thank you, Nate Green for inspiring the post.

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If you want my latest articles, announcements and personal learnings that I never post publicly, get on my private email list, here:


Michelle Florendo, is a coach for Type-A professionals and executives. She has served on the inaugural coaching team for Seth Godin’s altMBA, guest-taught on Stanford’s famous Design Your Life course, and is a founding member of the Forbes Coaches Council. Michelle is also a mother of 2, admits these achievements.

Her coaching philosophy is a blend of decision engineering, design thinking, and lean startup principles.

Michelle holds a bachelor from Stanford University, and an MBA from UC Berkeley.

In this conversation, we spoke about:

  • Michelle’s evolution as a coach
  • What is travel roulette?
  • Hard truth about being a coach
  • and much more!

If you’ve only got 2 minutes, here’s a short video 

Links Mentioned

Connect with Michelle Florendo:
Website | Linkedin 

Question to consider before to be a coach (Google doc)
Ask A Decision Engineer Podcast
Del Monte Food
Thinking in Bets by Annie Duke
Designing Your Life by
by Bill Burnett and Dave Evans 
Man’s Search for Meaning by Victor Franklin
Akimbo Workshop
Forward Link

Thanks for stopping by and listening!

Stay updated

If you want my latest articles, announcements and personal learnings that I never post publicly, get on my private email list, here:


Words are dangerous. Hiding in plain sight, they are so familiar that we have become flippant with our use of them.

When we are little, we knew the power of words. The word “no” could stop us from doing almost anything. And we can use it to stop almost anything to be done to us.

But as we grew, we stop paying close attention.

Last month, I wrote about Junk Dating. Although catchy, it is not entirely accurate. I could named it bulk dating, or dating by numbers, but I didn't. And it turned out that some of my past dates (who became dear friends) read the article and believe they are junk. Because after all, I didn’t put a ring on their finger.

The whole “sticks and stones” metaphor can be dangerous. When a stone can bruise, you will heal from it. But when a torrent of words undermines your view of what’s possible, you might never recover.

While I carelessly throw away my own words, my dates also carelessly hoard those words.

Words matter. They can hurt, injure and be mean. Or they can open doors, light a path and make a difference. Your choice.

(P.s. None of my past dates are junk. Junk Dating is merely a process of finding out what I want, and what works for me.)


Is it when you’re 9 years old, 19 years old, or 69 years old?

Think about that for a minute.

If common sense is really common then everyone should know it. But you don’t actually expect a toddler to do the things you do. Or expect a grandmother to see the world as you see it.

We can get angry at common sense and blame others for not knowing.

Or see it as an opportunity to make a connection, show possibilities and bring up the people around you.

Because what’s the point of getting mad when common sense is never really common in the first place.


It only works once.

No amount of money can buy back that moment of awe and inspiration. That same book, song, painting [fill in the blank] will never be the same again.

It changes you. For that very first time. It is the dish at that restaurant, tears rolling as you watched that film and arriving at that special city. You can't un-see, what you've seen.

The magic is the connection between the art and the viewer, seeing it for the very first time.

That how the Mona Lisa ended up selling for $100 million.

The alternative is expert craftsmen in the village of Dafen, China painting replicas. Their paintings are priced by size. Day in, day out, doing what’ve done before, no emotional labour involved. You can’t fail.

If you are one of the lucky ones to be peddling in magic, the work is to lean in, do things that might not work, make a statement and connect the dots. And once you found the thing that resonates with the culture, show it to the world, and pen your style.

And perhaps after the glitz and the glamour, it’s time to get back to the work. To try and to fail. To try and try again. Until the next magic comes about. The work of an artist.


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