What makes it worth paying the tax?

Regardless of what we choose to work on and where we choose to do it, we pay a tax.

At big companies, it might be all that time spent planning and coordinating. At smaller firms, it might be the uncertainty of whether things will work out. And, for those at home caring for loved ones, it might be recurring questions about your own relevance.

And, in every one of these situations, there generally is * that * person who seems to make things difficult.

Since there’s no running away from the tax and assuming you like being where you are, the only question, then, is – what makes paying the tax worth it?

Generally, it comes down to one or two things that matter. For example, if you’re designing/building products at a big company, it may be the joy you feel when what you build touches thousands of people at once. And, if that’s what matters, intentionally pick the 1-3 battles you most want to fight for this month that make paying the tax worth it.

It is amazing how much of a difference this little bit of re-framing combined with focus can make – they help move all the energy we’d otherwise waste in complaining to focusing on the things that move the needle – in our work and for ourselves.

Eighteen years later

I realized a week ago that it had been eighteen years since my father passed away. Or, more accurately, chose to pass away.

Reflecting on the experience, I realize I’ve never held his decision to take his life against him. For a few years, I wished he’d explained why. I also wished for guidance during a challenging period in my final year of college. But, there was still no negativity involved – it was his life to take after all.

And, while I might have been disappointed for a while, that experience has undeniably made me a better human being. I accumulated significant scar tissue on taking responsibility, expressing gratitude, love, and care and on not taking this life for granted.

Such scar tissue changes who you are and how you operate. It certainly did for me.

Eighteen years on, my memories of my father are few and far between. I’ve spent significantly more time at a more formative stage without him. So, that’s understandable.

I also chose to not dwell on some of the negative memories leading up to his eventual passing. Instead, the one thing I’ve chosen to remember was his insistence on owning good things. We didn’t have many things at home. But, the things we owned were good. He took a lot of pride in investing in a few, quality, things and experiences. I am very similar in that regard and grateful for that lesson.

There are more lessons I’ve taken away from that experience – perhaps I’ll get to those in next year’s note.

Reflecting on this reminds me of how little control we have on what happens to us. As a family, the aftermath of this event was devastating given it came out of the blue.

But, it also reminds me that we have more control than we think in shaping our future (with help from Lady luck) with the nature of our response.

For those of you who’ve gone through an unexpected bereavement, I hope you’ll take away the fact that, with time, love, and care… it gets better.

The challenge with how we measure our life

One of the biggest challenges with designing a good life for ourselves is that the stuff we measure our days, weeks, and even months with is not how we measure our life as a whole.

The stuff we measure our life with – living with integrity or building a few deep relationships with people we care about for example – come with no awards, no vanity metrics, no promotions, and no recognition. And, just in case that wasn’t hard enough, there are often minimal signs of progress for long periods of time.

On the flip side, most of the stuff that seems to loom large and feature so prominently in the near future (e.g. work/career milestones or fun side projects) seem to matter for the longest time… until they don’t.

It is the classic urgency vs. importance prioritization problem. And, as is the case with most things, it is much easier to talk about thinking long term/balancing the short and long term than it is to actually do it.

PS: This is much like building good products. The foreseeable future seems more important than it is.

All that remains and It’s later than you think

Dr Jessica Brandes and J R Storment were parents of an 8 year old boy who passed away 3 weeks ago. They both penned beautiful posts this week about this very painful experience.

In “All that remains,” Dr Brandes wrote about the fragility of life and pushes us to take the time to spend time with those we love.

And, in “It’s later than you think,” Storment reflected on his regrets and reminds us to be very intentional in how we prioritize our time.

I hope you take the time to read it.

Reminders of the fragility of this life are a gift. And, I’m grateful to Jessica Brandes and J R Storment for sharing their notes with us.

Just one thing this time

I was mulling a new weekend project today. For a change, I shut it down before the thought germinated.

As unexciting as that might sound, it marked an important moment in my learning journey.

Over the past months, I’ve been working hard to simplify my life so I can focus on the two things that I expect will move the needle on my long term happiness – learning and contributing at work and being as good a partner and dad as I possibly can.

There are a list of things I’d like to do more. For instance, I’d like to find time to play more soccer. I’d also like to write more long form posts. But, in reality, for the first time in a decade, I’ve barely played soccer in the past months. And, I haven’t done any long form writing on tech and product management either. So, before I get excited about a new weekend project, it helps to remind myself that there’s an existing backlog for when I have more time.

Of course, I’d like to do more than just focus on working and being there for the family. But, I haven’t found a way to do that without sleeping less and messing with my health – that, in turn, would mean doing a sub par job on the two things that matter at the moment. So, we’re back to square one.

It took a bit of reflection after having our second child last year to arrive at this conclusion. I care deeply about being an engaged member of the family. And, after ~7 years of career finding, I’m finally 2+ years into a role that is a great fit and intend to make the most of the steep learning curve that lies ahead. I’ve come to accept that there’s little time left after embracing these constraints.

It is lovely to experience this sort of focus for the first time. I don’t spend any time on weekdays or weekends wondering when I can squeeze a bit of time to do this or that. I can just be – assured in the knowledge that there’s nothing else more important.

For many years, I gave lip service to the idea of fewer things done better. I’ve written plenty about prioritization over the years and did a passable job at it. My answer in the past was always to find some way to fit as much as I could in. But, as I realized in the second half of 2018, that approach doesn’t work with hard constraints.

One of my favorite ideas in the realm of prioritization is that saying no to things that don’t matter enables us to say yes to things that do. I’ve shared this many times over as a wishful note to self.

It is only now that I am beginning to draw clear boundaries, embrace trade-offs, and say yes to things that matter.

I’m hoping I’ll be able to make more progress down that road in the coming months – both at home and at work.

Reflections on The Algebra of Happiness

I listened to “The Algebra of Happiness” by Scott Galloway recently. There wasn’t much that was new as it was a compilation of posts from his weekly blog – “No Mercy, No Malice” that I’ve enjoyed reading over the past months.

I’ve shared a few of his posts from time to time as I find his writing a nice mix of interesting, provocative, and heart warming. Amidst notes with strong points of view and occasional humble bragging, there is plenty about the struggles he’s faced and continues to face. The struggle to be a better son, father, friend, teacher, and citizen.

It is that struggle that makes life interesting and challenging all at once. And, I’m glad he shares that. Those are the sorts of notes that help put things in perspective.

My notes from the book are sparse. But, as I look back on what I’ve taken away, there are three notes that resonated.

First, Prof Galloway observes that hard work and a lack of balance early in a career has a disproportionate impact later. In the early years, speed helps. There’s no right way to do this – only we can decide what trade offs make sense for us.

Second, the ratio of how much we sweat to watching others sweat is a leading indicator of success.

And, third, the most important decision we make is who we marry – if we decide to do so.

Drafting a will

On May 25th, Seth shared a post on his blog about finishing well.

If you start a book, you will do better if you have a plan for finishing your book.

If you take the time and spend the money to go to college, it’s worth considering graduating as well.

Aretha Franklin died without a clearly stated will. As a result, her heirs will waste time, money and frustration, because Franklin was both naive (a will doesn’t make it more likely that you will die) and selfish.

If you’re born, it pays to plan on dying.

Every year, millions of people needlessly suffer in old age because they didn’t spend twenty minutes on a health care proxy.

If you’re going to take a job, everyone will benefit if you think about how you’re going to leave that job.

And if you start a company, you should realize that you’re probably going to either sell it or fold it one day, and neither has to be a catastrophe or a failure.

Beginning is magical. So is finishing. We can embrace both.

This post resonated deeply as my wife and I had spoken about creating a will after having our first child. We’d spoken in the past about a health care proxy as well – however, we never got around to doing it.

So, after reading this post, I made a note on my list of priorities during my week off in July to get it done. And, so, today, after a bit of research, we purchased Quick Willmaker Plus (there’s a 40% discount this week on account of Independence Day) and drafted our wills and health care proxies. It took us about an hour and we intend to sign it front of two of our friends to complete the process in the coming days.

It was time well spent. If you haven’t done it yet, I hope you will consider it.

Getting good at things you don’t want to do

I came across a thought provoking tweet recently – “Be careful about getting good at things you don’t want to do.”

As obvious as that sounds, it is fairly easy to fall into that trap if we are solving for extrinsic measures of success – more money, prestigious roles, better titles, etc. And, extrinsic measures tend to be a natural outcome if all we solve for is “what should I do next?”

A better approach tends to be to to invest in solving who we want to be instead of what we want to do.

It is more upfront investment to understand our motives and values. But, once we do the legwork, solving what we want to do in a way that actually helps us get good at things we want to do turns out to be surprisingly tractable.


I was reflecting on the sudden death of a young friend yesterday and was reminded of just how transient this life is.

It is so easy to get caught up in the all consuming puzzle/issue/tiff/ego battle of the moment. It is easy to forget that these things can change in an instant.

Reminders of our mortality are powerful reminders to keep perspective. This was one of them. It also reminded me of a lovely quote I once read – “Be kind to each other. The world will roll on without you.”


Societal success and scale

It strikes me that one of the biggest challenges we face is reconciling our desire to be successful by societal definitions while not giving up on being successful by our definition.

The challenge lies in the fact that extrinsic measures tend to be breadth focused (e.g. number of customers/successful exits/employees) while the stuff that make us feel intrinsically successful tend to be depth focused (e.g. deep relationships, immersive experiences).

Anyone who has built products or services has faced this in their work. It is much easier to move vanity metrics than it to create meaningful impact.

The answer, in work and in life, isn’t to shun extrinsic measures and breadth. We need some of it to ensure it doesn’t get in the way of us getting to the intrinsic stuff.

The challenge, however, is not being so sucked in by the allure of breadth and scale that we forget that its main purpose is to enable the depth we really seek.

Put differently, the optimal strategy tends to be to do things that scale easily so we can then spend more of our time doing things that don’t scale.