✉️ A Letter to My Younger Self
If I could send one email to myself as I was finishing college, this would be it.
In 2021, I came to a big crossroads in my life. I was 25, had a great career underway, and on a clear path to relative success and comfort. To be clear, this is exceedingly rare and I’m exceptionally lucky to have the privilege to be in this position at this age. It’s important to call that out because many take it for granted.
Professionally, I felt some degree of “imposter syndrome” - being the kid from the state school surrounded by peers from Ivy leagues. I subconsciously believed that I had snuck into big tech, taken the backdoor to success, and if I risked it I would have to rebuild it all from scratch.
In hindsight, I think that lack of confidence was a blessing and a curse. It drove me to push my career very aggressively. This was great for my career, but it didn’t address the root cause of my insecurity. At my core, I didn’t believe in myself. I would use external validation from promotions, praise, and compensation instead of being proud of the work I did. This put a tremendous amount of pressure on me and gave a ton of weight to things I had little control over. I would get a promotion, and immediately start chasing the next one.
Getting Technical Lead was the goal I set out to do when I joined Twilio. But once I achieved it, I wondered what was next? Was this a sustainable path? I would often talk about this nonstop path of level chasing (often known as the Hedonic treadmill). At one point, would I need to become CEO of Twilio? President of the USA? Something needed to change. I needed to start over.
The reason I’m sharing all of this is that I’ve realized that if you don’t believe in yourself, nothing will ever be good enough.
I’m still working on myself, it’s a journey, not a checklist. But after spending years focusing on that goal, I can say I’m in a much better place.
Learning to believe in myself was the prerequisite for the next stage in my life. Without it, I would never be able to fully capture what I’m truly capable of. And that is critical for crafting a vision that’s big enough to dedicate my life towards.
Living an “Intentional Life”
On a flight a few years ago, I picked up this book called Flow: The Psychology of Optimal Experience. It’s long-winded, and the summaries give you most of the lessons (this is true of most self-help books, but reading them forces you to spend a lot of time absorbing said lessons).
“Flow by Mihaly Csikszentmihalyi takes on the problem of how to live a happier life. A meaningful life is one where the person spends his time in a state of optimal experience called Flow. To live a great life, all your goals must be unified in a way that produces the maximum amount of flow.“
One of the biggest takeaways I had from the book is that you do your best work when you are intentional with what you’re doing. I believe you can generalize this to life as a whole. We can live our best life when we are intentional with what we are doing with it.
As an aside, I think it’s important to underscore the ROI of spending time reflecting on one’s goals. If you can spend one weekend completely focused on these ideas, it can potentially save you years going down the wrong path.
Living an intentional life means taking the time to understand what you want out of it. At first, this can be a daunting task. However, by breaking it down and providing flexibility, it becomes a fun exercise. It’s also important to note that things change, and while the goal is for the vision to be directionally accurate, sometimes priorities and desires change. And that’s ok.
In the wise words of Hunter S. Thompson:
“To presume to point a man to the right and ultimate goal—to point with a trembling finger in the RIGHT direction is something only a fool would take upon himself. (...) But a man who procrastinates in his CHOOSING will inevitably have his choice made for him by circumstance.”
- A letter April 1958 from Thompson (age 20) to his friend. Worth a full read.
I think the process I’ve followed roughly looks like this.
1. Learn to believe in myself.
2. Define the values I believe in.
3. Create a vision for the life I want to live that encompasses those values.
4. Work backwards from the vision, and set goals to get there.
Organization
Before diving deeper into this process, I think it’s worthwhile to pause and highlight that this entire practice is ineffective without writing down these thoughts and ideas. Writing demands you to be intentional about what you are thinking. I’ve never considered myself a great writer (and generally dread doing it), however, I think it is absolutely required for this process.
I like using Notion to create organized thoughts around big decisions. I started using it when I was considering leaving my big tech job, and it’s grown to be a central part of how I plan big life things.
Values
Values are the building blocks for who we are. They can be small quirks like “I strive to be punctual” or massive identifiers such as “My family is my most important thing to me.”
Crafting your values requires deep introspection. I had trouble doing this on my own, so I spent some time with a trusted friend crafting ours together.
I defined my values by asking myself “What am I great at?” If I consider myself great at something, then I must value or enjoy it. From there, I try to understand what I would describe myself in this way. For example: “I am patient. I don’t mind waiting for things to work as long as we keep making progress.”
Notice that these are positive values. They embody the things about myself that I am most proud of. These values are constructive, and help me prioritize my strengths and passions. Negative values start with “I am not ...”, and they aren’t helpful in this process. I wanted to define myself by who I am, not who I am not.
Vision
After spending time understanding my values. I worked to define my vision. A vision to me is a general mission statement for my life. I tried to focus more on the feelings I wanted to feel as it allows much more flexibility in the vision. “I want to feel empowered to take vacations as needed” is much more flexible than “I want to be rich enough to take a vacation whenever I want”.
The vision I crafted for myself has three parts:
What I Want To Have - What does my ideal life look like in 30 years? Who am I surrounded by?
Who I Want To Be - If I met myself in 30 years, how would I describe that person?
How I Want To Do It - What is my ideal path to get there? Not necessarily a step-by-step plan, but what’s the ideal path.
Remember, this is all high level. It’s about setting the direction for our goals that we’ll craft. These don’t need to be perfect, but the statements should resonate within you. When I read mine, they feel very authentically me.
Goals
When I was 18, I set some very high-level goals for the next seven years.
1. Graduate college.
2. Make six figures by working in tech
3. Marry my girlfriend
4. Become a CTO
This was a rudimentary and short-term version of the process I’m describing today, but it played out pretty well (I ended up accomplishing 3/4). I didn’t even want to be a software engineer or a founder when I started on these goals, I thought I was going to be a sysadmin. It’s crazy how when you set ambitious goals on a long time horizon, things still work out.
Goal setting has been something I’ve played with for a while now. I started writing consistent, high-level, yearly goals in 2016. These goals were very high level, and sometimes hard to measure.
We can work backwards from our vision to craft goals. If you could accomplish one thing in the next year to get you closer to your vision, what would that be? That’s a great start. Our vision is big, and sometimes we may need to accomplish multiple goals to make progress. If your goal is to “love yourself” that might require some work on your mental health, physical health, and relationships. You can go down a rabbit hole here.
If you have no idea where to start, that can be a goal too! I’ve always made an effort to meet people who are living the vision I want and attempt to understand their path. This is one of the reasons I love reading biographies.
Goal setting is a continuous process. It’s worth evaluating them regularly and tweaking them as needed. Goals also require reflection. After some time has passed, it’s worth writing about the progress you’ve made on your goals, the lessons you learned, and what goals you want to focus on next.
Even though we’re almost halfway done with the year, I’m still changing them! As I said, it’s a continuous process.
In Summary
Taking all of this in at once can be overwhelming. Some may look at this process and wonder if I’ve let go of all spontaneity and fate in my life. That’s a fair criticism, and I think some implementations of this system can result in much less freedom. Alternatively, by living intentionally, you’re able to prioritize much more effectively, resulting in more freedom overall.
Sometimes you will have to overcome short-term pain/adversity to accomplish your goals. I’ve found that the best weapon against this adversity is to embrace it. In Viktor Frankl’s book Man’s Search for Meaning, he writes about his experience surviving a concentration camp. He found that the ones who were able to survive the horrible conditions were the people who had “will to meaning” - the desire to live a meaningful life.
“Everything can be taken from a man but one thing: the last of the human freedoms—to choose one’s attitude in any given set of circumstances, to choose one’s own way.” (Frankl)
The secret to this whole thing is that it isn’t really about how you accomplish your goals, but how you set them. Once you set meaningful goals derived from your vision that align with your values, you’ll automatically gravitate towards accomplishing them.
Our time on this earth is limited. We don’t get to choose how much of it we have, but we do get to choose what we do with it. That’s why I believe it’s worth living intentionally.