I was asked a question once, probably months ago, about whether or not I would consider myself to be the most successful of my siblings.

The implication, of course, is that me working in the Bay Area at a large tech company somehow makes me more successful.

I really detest that implication, and I couldn't fully answer why at the moment beyond that it felt offensive and wrong to me. After some thought, this is the answer I came up with, and how I think of success.

Do mind, this is a hard post for me to write, as it's been the result of me thinking for months on the past five to ten years of my life.

Who are my siblings?

To start with, I have three siblings, all younger.

My First Brother

My first brother is currently in medical school working towards likely ophthalmology with a masters in psychology. He's happily married and has a great group of friends, and spends time mentoring kids going through school in his spare time. He has a heart for those who are neurodiverse and will frequently spend time researching to try and learn more.

Not only is he actively making a difference in the lives of young men in his community, he's actively involved in research to help make the world a better place.

He's built a community around medicine and his faith that helps those around him grow.

My Sister

My sister is currently teaching elementary and working on a master's degree. She's also happily married with a great group of friends around her. Her heart is in teaching kids and helping them grow, planning events, and creating a sense of belonging with those around her.

She's the social one by far. Whereas my brother builds small intimate communities she builds across families, states, and anything else to bring people together.

My Second Brother

My youngest brother, well, he's just now a teenager. Given that, certainly not married. In many ways he reminds me of myself when I was younger, except that he fully knows he's autistic (asperger's syndrome) and can get the support he needs. A sharp wit, a love for art and music, and a potential for quite a future ahead of him.

Myself

As for myself, I'm a senior software engineer working as a Ruby language architect. I speak at conferences, write, and several other things that aren't necessarily relevant to this post.

The Question

What is relevant though is a question that underlies this:

Which one of us is the most successful?

What Do You Mean By Success?

Now how does one define success? What metric are we gauging by? What KPIs and OKRs can we check off on the grand game of life to prove beyond a shadow of a doubt that we were successful?

I'd read a book once on the nature of mastery, and in it there was a very simple truth. There is no real destination, no mark by which you can objectively say you're a master.

The road to success, mastery, and much of anything in life takes many paths. None of which have an end, and that's either staunchly terrifying or thrilling. To me it's both, and perhaps a bit liberating.

Happily Married?

Now with the exception of my youngest brother, the rest of my siblings are married.

One could fairly say that, from the perspective of the midwest, I've failed in this aspect. Most people back home are married some time before they turn 25, and I'm certainly not that young anymore.

Do I define my success by whether or not I'm married or dating someone? At one point I did, and that type of thinking can wreck a person. It's not healthy and can lead to some very bad decisions very quickly.

One can become desperate to be married to the exclusion of everything else, good judgement included. Tying my success to this metric led to a lot of misery.

As I've grown I've become okay with being single and living my life as I will, exploring my passions and what makes me me. Being married, in a way, was running away from myself.

Now that's not to say there's anything wrong with marriage, I'm happy for my siblings in this but it's not where I am in life and that's perfectly ok.

Wealth?

Living in the Bay Area there's a substantial amount of wealth. In many ways, a truly disgusting amount of it, especially considering what it does to those that are the most vulnerable among us.

Despite that it's become a game, a rat race to the top of the ladder. We'd only be happy if we could make 200k a year. Well, maybe 300k. 400, 500, 600? A million?

At what point of wealth does one stop and say they have enough, that they're a success?

Making this a metric of success is one of the most dangerous things one can do in life. Money can consume a person, strip them of their empathy and humanity, and destroy the foundations of the world around them.

Sometimes I feel like we trade everything that makes us human just to get to that next level. It's an evil thing.

Does the work that I do change the world? Is it worth hundreds of thousands of dollars a year? At the end of the day I just move money around more effectively.

My sister makes a difference in the lives of a significant number of children, gives them hope for a brighter future, and helps them on their way there. Her students may be engineers, doctors, teachers, or who knows what else. Our future is in our education and our children, and in the teachers who get them there.

Given that, her salary ends up being a fraction of mine despite this. Am I more valuable than one that makes such a difference in so many lives?

I would contend not at all, and if anything I think teachers are substantially more valuable. It's unconscionable to me how little they're paid for the difference they make while some in this world make their salaries in mere seconds.

No, wealth is a corrupt metric, and one of the fastest ways to lose yourself in the process.

Generosity?

Is our success defined by our generosity? In how much we give?

For me I'd tied a metric of success in wealth to how much I could give back. My climb up the ladder was driven entirely by wanting to be able to make those significant donations that could shape the world, and quite frankly it was horribly arrogant.

I grew up Christian, and in many ways I remember this story:

Jesus sat down opposite the place where the offerings were put and watched the crowd putting their money into the temple treasury. Many rich people threw in large amounts. But a poor widow came and put in two very small copper coins, worth only a few cents.

Calling his disciples to him, Jesus said, “Truly I tell you, this poor widow has put more into the treasury than all the others. They all gave out of their wealth; but she, out of her poverty, put in everything—all she had to live on.”

Mark 12:41-44 (NIV)

Now I don't advocate for giving all one has to the church, I certainly have opinions on that, but that's not quite the point of this parable. The point is that those who were rich put in large amounts to show their great wealth and to be praised for their generosity.

They did it for show, and their hearts weren't fully behind their actions. I often question if I've done the same, if I only donate to glorify myself and prove what a good person I am, to show how successful I am without being "consumed by wealth".

...but is that really the case? Because it sounds quite a bit like I am in a way, and that's something I still struggle with.

Why do we give? There's always more that can be done, more that can be given, an extra step, an extra mile. Are we so attached to our possessions and our wealth that we cannot give back?

Defining success by generosity feels, to me, a fast way to self-gratification. Generosity should be done from the heart, from research, and towards the betterment of the world. Not self-gratification.

I still struggle with this one, and honestly don't know what to think of it.

Metrics are Broken

As with KPIs, OKRs, and other metrics they can all be gamed. We become more obsessed with hitting an arbitrary metric than with actually improving and continuing on our journeys to become truly successful.

Gaming a metric will leave you feeling empty because there's always another arbitrary metric to meet, another game to play, and all the while it's far too easy to destroy people along the way in the pursuit of them.

So What is Success?

I don't know, and I doubt I ever will, and that's ok.

My definition of success changes frequently, and could be any number of things.

In the mean time I can only seek to be a better person, to improve the lives of those around me, and to work on my mission of improving education.

My goal is to leave behind a better world for those who come after me, for a generation I'll never see or know, because I want to believe in a brighter future. I'll consider every step towards that goal a success, and I'll continue learning as I go how to become better at it.

If I had to distill what it means to me today to one phrase, it would be making the world a better place through education.

Which Sibling is Most Successful?

All of us are, in our own ways, in our own time, and on our own paths.

We grow, we learn, we laugh, we love. Success, to me, is making the world a better place and I believe all of us are working towards that in our own ways.

What's Your Success?

What does success mean to you? What drives you? There are as many different answers as there are people, and that's ok. Some define it as bringing joy, others as serving, and so many more are out there.

The secret? It takes all of us together to really change things and make the world a better place.