Current Life Plans

Over the span of my life my mind shifts in terms of what I think I should be optimizing for. Since moving to New York roughly eight months ago I’ve been looking at what matters to me right now and I’ve decided to write about it for no particular reason.

I don’t really have a motive for making this public other than attempting to take a snapshot of my current thinking for my future self to laugh at. Also, I Tweeted something last night that received more feedback than expected so I promised I’d share my thoughts. I actually have had this post half-written for about two or three weeks now so finally cleaned it up and hit the publish button.

Here are my personal thoughts right now at about ~28.66 years of life.

What matters to me

I have three mediums (oh-ho, see what I did there?) where I jot down thoughts: My written Journal (entries added near-daily), the Notes app on iPhone (a single note I re-read every two weeks at this point) and a Google Doc aptly entitled “Life Plans” which has a few bullet points which I occasionally delete and add to. I fully realize how over-analytic and psychotic this may sound…but has actually helped me make decisions and make sense of myself a lot. Here are the higher level groupings of what matter to me at the moment and what motivates much of what I do:

Being Bold

I only have one note written on my phone. It is about three paragraphs long written when I was going from one city to the next on a long bus ride when I was particularly sad. The second paragraph says: “In looking back, despite the outcome, I’m incredibly proud of myself for taking the initiative and making something happen rather than thinking about it endlessly with no action. I went for it and got somewhere and learned something from it — even if wasn’t exactly what I thought it would be.”

The best things in my life have come from being bold, despite the fact that I was scared shitless in the moment: Starting a company at age 21 by myself, quitting my cushy corporate job to travel the world on my own, dropping everything and moving to NYC not knowing a single person, asking the girl(s) out.

Interestingly and not purposefully: All of these things have happened from a place of being very alone. They were also things that I went with my gut on — despite the objective logic probably advising otherwise.

Personal Relationships

Throughout my life I’ve consistently sucked at conveying how much people matter to me. This holds true across the spectrum: from coworkers I really enjoy to my immediate family. It really comes from operating under the incorrect assumption that the people in my life who matter to me would “just know”.

In the last few years I’ve come to realize that all that really matters in life is people. Jobs come and go. Money comes and goes. Cities come and go. At the end of my life I think I’d be happy to look back and remember my family and friends and the times we had and less so the career / investing / material wins.

Every day I try to be more explicit with this — and its incredibly difficult for me for some reason. Telling a coworker I enjoy that I really like working with them, catching up and staying in contact with distant friends and trying to be better about keeping in touch with my family are things that I’m really focusing hard on at the moment.

Lastly on this point: I’m actually at a pretty good spot for myself in life right now which I’m becoming increasingly aware of. It hasn’t always (or ever?) been this way and I probably have some hard times ahead — life has a tendency to ebb and flow. My hope is that I can support people who need help right now — if for no other reason that I’d like to think people would do the same for me when I inevitably get beaten down by life a bit in the future for a stint.

Saving Voraciously

I was raised to be in the mindset of saving money so this one hasn’t been particularly difficult for me — but lately I’ve been really going full-force on it. In the Google Doc I mentioned above, next to this point was “account for your future family.

At age 23 I can’t imagine thinking of looking ahead five years and anticipating something like this for myself at 28. However, at age 28 looking five years ahead I’d like to think at 33 I’m at a spot where I need to support a family. While money isn’t the be-all end-all in this regard I can imagine it will ease some future woes if I’m able to save now.

Increasing Optionality

Choice is a really wonderful thing. Although you don’t have much of a choice if you only have one option. As a result, optionality is incredibly important to me right now in two realms: living and working. My apartment is actually quite great at the moment but I really cherish the fact that it is month-to-month so that in the event that I need to make a drastic life change for whatever reason I can. (roommates: if you’re reading this — I love each and every one of you and don’t plan on moving anytime soon — its cool.)

Optionality is also important to me in regard to work — which I realize may be taboo to say but I think is the reality of things. I’m always going to be looking for ways to improve, grown and learn — I would love for that to be the case at my current company. Additionally, it is incredibly important for me to experience mutual trust, be respected and feel that my colleagues are giving a damn as much as I force myself to.

Regardless of what company I’m at: I feel more-so these days that I should be objectively evaluating my job as much as my company is objectively evaluating me in my position: which I think happens a lot more than people let on to. If to only reinforce that my current position is the best for me at the moment then I consider the exercise a win.

Being Patient

By nature I’m someone who is excited by what’s next. This works counter-productively a lot of the time where I’m rushing to figure life out (hmmm, should I be writing this post?) and live in the future a bit. I really have two modes of operating: 0% or 100%. I’m really trying to work on finding a better balance and not putting the pedal to the metal all the time.

I’ve tried to slow down my life a lot lately — not planning weekends and walking around the city to take it all in, beginning yoga (sigh, I know…I know…) and not letting long-term gains be impacted by being unwilling to do a short-term sacrifice.


That’s all I’ve got. Have thoughts on the subject? Agree? Disagree? Think I’m missing something huge? I’m curious to see how people think about these things, if at all.