Are We Intentional With Our Lives? Thinking Backwards and Forwards.

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It’s happy hour at a hip Thai restaurant in Fremont, Seattle. I’m seated at a table perched on a platform with a view of the entire restaurant. The appetizers on the table have gone cold and I’m clutching my beer like a security blanket. For the last 15 minutes, I’ve been fumbling through an explanation of what’s been on my mind recently.

It’s a conversation I’ve been dreading for weeks. I have no idea if it’s all making sense. At one point I blurt out,

“It’s not you, it’s me.”

I had just told my boss that I wanted to leave my job. I was less than a year into a dreamy new role at Amazon. I was working on a large new opportunity alongside some of the smartest and most inspirational people I’ve ever met. But here I was, wanting to back out, and with much less of a concrete plan ahead of me.

As we progress through life, one of the oddities I’ve noticed is that with less time left in our lives, the time we have left seems to pass by faster and faster. Not only does time seem to pass quicker, but we often move along life in a kind of default mode, accepting what comes to us, or doing what we think we’re supposed to do. Particularly after 2020, which felt like a lost year of chaos, I thought deeper about whether I was using my time on this planet in the manner I truly wanted.

Am I intentional with my life, or am I playing life on default mode?

If I’m honest, I’ve lived large portions of my life in a default mode. To help me think towards an intentional life, I used two techniques recently: thinking backwards and thinking forwards.

Thinking Backwards

“Did I live a life well lived?”

For all of us, our time in this world will come to an end someday. If I’m lucky enough to live a long life with the opportunity to reflect back on my life, I want to answer the question, “Did I live a life well lived?” with a resounding yes.

What defines a life well lived is unique for each of us. To help me define what it means for me, I thought of two questions I’d ask myself near end of life:

  1. What did I do that was meaningful?
  2. What did I not do that I deeply regret?

For both these questions, I tried to imagine how I would answer towards the end of my life.

What did I do that was meaningful?

‘Meaningful’ is a hazy buzzword, and it’s important to further define what it means for each of us. For much of my career, meaningful accomplishment meant increasing compensation and prestige. Money wasn’t just a means to fund a lifestyle, but was also a scorecard used to validate my worth and status. The higher the score, the more ‘meaningful’ success I was having. Decisions such as what to study in college, what job to take, and what city to live in were all driven by a desire to optimize for my definition of meaningful accomplishment.

Let’s imagine I achieve or surpass my definition of meaningful success – I achieve high levels of monetary wealth and reach enviable career prestige. At end of life, will I be proud to say “I achieved my goals of x dollars and job role of y?” While I enjoy and desire money, at the end of my life, I can safely say that financial accomplishments will not be among the most important accomplishments in my life. Worse, the achievement of financial goals could come at the cost of something higher in meaning for me.

So to answer the first thought question, I have to clearly understand what I believe is meaningful, and place focus on those items. Nowadays, meaningful is defined for me as something that contributes to bettering those around and ahead of me. Contribution to helping others provides me with a deeper and longer lasting sense of joy, accomplishment and pride, and is something I now strive for.

What did I not do that I deeply regret?

Regret is suffering over the past. Regret over something I did not do plagues me with a “what if?” mindset that can painfully linger throughout life. For example, if a health ailment strikes me later in my years, and if the ailment was preventable via regular exercise, I would deeply regret not exercising in my earlier years. I have no control over what ailments may strike me, but I know regular exercise reduces the risk of some serious health ailments from occurring. The regret of not taking action now motivates me to make exercise a priority.

This thought process for regret can be done for actions that move us away from something, such as unwanted health ailments, or towards something. For moving towards something, an example for me would be entrepreneurship. Entrepreneurship was a desire for me, but I worked in large corporate companies, from where the safer confines made entrepreneurship look like a romantic, yet unpractical idea. But if thinking from the lens of what actions I would regret not taking, pursuing entrepreneurship and starting my own business would rank very high. The regret alone was a significant motivator for me to take action towards entrepreneurship, where I quit my job and started a company with a friend and former classmate.

Whatever I can foresee as a possible future regret in the future, is something that needs to be prioritized now.

Thinking Forwards

“Where is my current path taking me?”

We often have a general idea of what we’d like our life to be like in the future, for example we might image a certain family, a house, a job, and so on. But how often do we think about what we truly want, and not just what we’re supposed to want? Furthermore, even if we’ve identified what we truly want, how often do we think further about achieving what we want?

Once I’ve identified what I truly want, I’d think think forwards to help me understand what needs to happen now:

  1. What are the priorities of the items identified? I’ve learned that significant attention is required for me to achieve almost everything I’d like in life. It’s impossible for me to achieve everything, so I have to prioritize given the trade-offs off everything I want. Priorities help me double check how important something is really to me. With an understanding of what’s important, I take stock of the current situation:
  2. Am I on the right path for my desired future? While I have no control over how things ultimately turn out in the future, I can look at my current activities and situation and project out where I could end up if I kept on the current path. For example, if I study Japanese as a daily habit, it’s reasonable to infer that if I keep on the same path, sometime in the future I will be proficient in Japanese. Whatever my desires are in life, I need to check if I’m doing the right activities at this time, to set me up to achieve my desires.


Back at the restaurant, we’ve overextended our stay and begun to walk around the block in the neighborhood.

“So what do you want to do?”

My boss asks me with a part surprised, part curious, and part empathetic tone. I gave a long winded answer about the ideas I have and what I saw as my priorities in life. I even went on a tangent about the meaning of life. But it all boiled down to “I don’t want to be doing this job.”

As I think backwards and forwards with my life, I realize that some of the answers will take experimentation to clarify. Some aspects of life have clarity on importance for me – for example physical and mental well being, family and friends, and a constant state of learning. Career ‘success,’ as I previously defined, is now clearly lower in priority than these categories.

My boss and I agreed on a leave of absence for me. It’d give me a chance to focus in the short term in other areas of my life and some time to explore and experiment with career possibilities.

I have a hard time explaining my decision to most people. The default behavior for us is to strive for ever better jobs. The idea to leave work to focus on personal well being, or to pursue curiosities, doesn’t make sense in our status driven society. I joke with friends that my explanation varies depending on who and the amount of time I have to discuss the topic.

No matter the reasons or the outcome, I know that in the future, I have one less item I won’t regret not doing.

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