Reassessing My Definition of Success

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Definition of success (Green-Wood Cemetery lake)

In 2010, we moved into a new office a few blocks away from the Flatiron District in Manhattan. Coming from a small, dark room at a co-working space, the new office felt like a dream come true. We had a conference room, a private office for me and my Barrel co-founder Sei-Wook to share, and an open area for about six employees.

Barrel office circa 2010

A shot of our Barrel office on 27th street, which felt at the time like it would be a long-time home for us.

I distinctly remember talking to Sei-Wook after our move and saying, “This place is amazing, we’ll probably be here for the next ten years.” We had two employees at that point and I couldn’t imagine getting much larger than that. Business was humming along, at least versus the earlier days of hardly any activity, and the future felt full of possibilities. I felt like I had achieved a measure of success and was on the path for more.

In less than 18 months, we outgrew the space and moved to a larger office downtown. We would outgrow that space not too long afterwards and move again. We had a few years of what felt like exponential growth. We had more work than we knew what to do with and was constantly hiring new people.

Funny thing is, through those years of rapid growth, expanding headcount, and ever more impressive client names, I can’t recall ever feeling successful. If anything, I felt like I was struggling more than ever and farther and farther from achieving what felt like success.

The expectations grew just as rapidly as the business if not at an even faster pace. I never took a moment to take a step back and ask myself what I was working towards. All I knew was that “success” meant continually growing and to have ever more things to brag about to peers, friends, and parents.

There was no ah-ha moment when I suddenly realized that I needed to reassess my definition of success. I experienced slow drips of realization through reading, writing, and just living life. Additionally, experiencing my fair share of down years, when things went sideways in the business, helped to give me perspective. What was I working towards? What did success mean to me?

For much of my life, the idea of success was closely associated with achievement, especially marked by money, credentials, and recognition. As my discontentment grew through up and down years at Barrel, I wondered if perhaps there was more to life than trying to achieve.

I began to spot different variations of success in my life:

  • The way my Dad brimmed with energy in pursuing a wide range of interests from foraging mushrooms, studying Nietzsche, and practicing Chinese calligraphy. His lifelong curiosity and insatiability when it came to learning was inspiring. Regardless of where he was financially, he did what he wanted to and brought both intensity and focus.
  • Seeing my in-laws surrounded by six (soon to be seven) grandchildren, proud and grateful that their adult children have all built happy lives with healthy families.
  • The relationship with my Barrel partners – the strength, resiliency, and depth of trust we’ve built with each other. To come to work every day and be happy and energized to see my partners, I realized, was not something to take for granted. We worked hard at it and it’s a form of success that many would more than willingly trade for.

As I thought about revising my definition of success, I began to more broadly explore the question: what kind of life do I want to live?

What became clear was that a life of striving for achievement and external validation, while good for the occasional high and ego-boost, was ultimately dissatisfying and eventually unsustainable.

I continue to explore the question posed above on a regular basis. It’s not one that I think has a definitive answer but has facets that express themselves more strongly than others depending on my life situation.

For example, writing today, the kind of life I want to live–one that I can deem as successful–include the following conditions and behaviors:

  • Pursuit of excellence: getting better, learning more, and going deeper into my various career and personal interests. Rather than seeking external validation, it’s about having an inner scorecard and pushing myself to test my own limits. The byproducts of pursuing excellence can range from increasing personal wealth, building deep knowledge, being a good parent, and a number of other things, but they are not the motivating factors.
  • Discipline and self-control: continually building the ability to better control my emotions, to maintain healthy routines, to avoid unnecessary or harmful distractions. Through discipline and self-control comes the energy and confidence that can help me show up as the best version of myself.
  • Practicing gratitude: never losing sight of all that I’ve been privileged to have in life even through tough and unfortunate moments, to feel lucky and blessed that everything in life I “get to” vs. “have to”. Embracing the concept of “enough” and using gratitude to fuel my desire to serve others.

When I look back on my writing over the past few years, these themes repeat themselves and show up over and over again. My Four Things to Consider for My Forties” and Lessons from Stillness is the Key by Ryan Holiday” are a couple of posts where I go into these points in greater depth.

For me, there’s been a sense of clarity and peace that’s come with reassessing my definition of success. It wasn’t long ago that I was wracked by anxieties from comparing myself to the perceived success of others on social media (see my post “Dark Moments & Counters”). These days, the first emotion is usually of respect and then followed by curiosity – what can I learn from them to help on my own journey? Any feelings of inadequacy or envy, of which there used to be a lot, are just no longer there. It’s taken work to get my mind here, and it’s been well worth the effort.

Make no mistake, I consider myself ambitious. I believe life is filled with amazing potential and creative possibilities. I have high standards for myself, and I truly believe that I am an important part of building something special and worthwhile, in both business and my personal life. What matters to me more is not so much “When will I get there?” and “What does it look like?” but instead, it’s all about “How will I conduct myself on my way there?”


  1. Mungrovy says

    Love it and saying I “get to” vs “have to” is a great reframe I’ve tried adopting myself. Congrats and cheers to the journey!

  2. Your journey from an initial, externally focused understanding of success to a more introspective and self-determined one resonates – albeit I’ve never had a bunch of employees.
    I think many of us can relate to your earlier years of constantly chasing growth, financial achievement, and external recognition. But, as you aptly pointed out, these milestones often leave us feeling empty or constantly striving for more without taking the time to appreciate how far we’ve come.

    Your redefined notion of success – focusing on personal growth, self-control, gratitude, and the journey rather than the destination – is a refreshing perspective. Particularly, your mention of the concept of ‘enough’ and gratitude acting as a motivation.

    Your insights have provoked some deep introspection to a powerful reminder that success is not a one-size-fits-all concept but rather a deeply personal construct that evolves with our life experiences and changing priorities.

    Thank you for sharing your journey and inspiring me and undoubtedly many others to redefine our understanding of success.

    I look forward to reading more about your journey and the insights you glean along the way.

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