Important, Not Urgent

I have some free time to think this morning and I'm scared I'll waste it.

75 year old Ira, what would you have wished I'd done in my late twenties?

My guess is that Maslow's pyramid would dictate having a very happy nuclear family: wife, kids – a house in a city that I love. This is base and core.

  • I think I want land, and a house that's decently sized. Not too large like a mansion, but well-customized to my needs.
  • I've always assumed that I'd live in luxury, that I'd have nice things of good quality and longevity. But this seems like two separate assumptions, one of achievement, and one of comfort. Odd how these two seem bundled together.
  • So it seems like the first priority is to figure out a plan for what things cost, and maybe work backwards from that goal, to start saving like what my mom did for college.

But also I think that might extend to Irvin, my parents, and last, to my grandparents, in an idealized version of myself. Torso, if you will.

  • I think the key here is to just spend time with them, and rather often too.
  • For example, I have this pipe dream of going to a museum with my grandpa. Would he want to do something like that?
  • * What does it mean to know my grandpa as a person? Realistically, I don't know him. I remember feeling so connected when he shared his life story with me at KST.
  • * Does it make sense to continue lying to him about work? That I've been walking down a non-traditional path for years now? How can I share with him my love for coffee, as an example? Can his heart handle it?

Thinking about family makes me also realize that the Ko's are rather woefully unprepared for retirement.

  • My parents don't have any 401K savings nor an IRA.
  • Most of their assets are in liquid cash or illiquid (the house).
  • Mom and dad are rather healthy right now, but what about medical expenses and lifestyle expenses? After 60 years of saving up and sending us to school, what kind of lifestyle do they want to have? What kind of travel will I want to offer up to them?
  • ** It seems to me that travel seems like an integral part of pinnacle Maslow. Travel opens up minds and makes the world feel smaller than what it really is.
  • What about grandma and grandpa's funeral expenses? Who is thinking about that? Who's going to be most capable of paying these down?
  • And after that, how will I send my own kids to school? Penn's not going to give them a full scholarship, like they gave me.

So much to think about.

In the past, I thought of career in a somewhat linear fashion (even though my slope was higher than that of many of my peers, I didn't make many exponential bets, because at the time, it felt uncommon to do so; everyone was just grinding at their 9-5 jobs). I had the goal of being a PM and making a certain salary. But once that salary was achieved ($200 TC), I sort of just coasted. I had spent years saving up money by living at home and I was ready to capitalize on some of those investments.

  • I lived in SF, lived in Brooklyn, bootstrapped a company, worked in coffee relying solely on my savings.
  • In my early twenties, I spoke about an impending correction. We are in that correction right now, and it's occurred to me that I hadn't deployed any of that dry powder at all, but rather spent it learning about myself, exploring... but not really traveling or seeing the world more.
  • So there's a matter of investment as well. How do I get most of the S&P500 at a time where investor sentiment is considered "bleak"? And yet, we still appear to be at all-time highs, despite "bottoming out" last September '22.

I had thought I'd hit the "top" of what I could achieve, but even now in my mind, I realize I'm self-limiting my expectations (the proverbial glass or bamboo ceiling?).

Basically, what I thought was enough, is not enough.

So it seems now that there are a few buckets to focus on. And it's probably impossible to focus on all of them at once, but they need to be prioritized.

  1. Figuring out what home looks like in the near-term, with a family.
    - What city? What's important about this city? Food, proximity to family, friends (?)
    - What type of home? How much will it cost? What design?
    - Wife, kids?
    This is probably the most important.
  2. Funeral expenses for my grandparents. This is the most urgent.
    - How much does it cost?
    - Who's going to pay it? How much am I responsible for?
  3. Wedding
    - Expensive as shit. What's the best way to think about this realistically?
  4. Mom/Dad Retirement
    - How much do they have in the bank?
    - In the form of assets?
    - What does a holistic picture look like?
  5. Own investments

I guess there's something to be said about my own cost of living as well. Currently, I've reduced most of my spend to live like a new-grad. I don't purchase things from Amazon anymore and I generally stretch my dollar in terms of food and consumables. I've become scrappy again.

  • But I do think about how I want to spend time with Iris, how to make her happy despite not spending wildly on ski vacations and bike trips around France.
  • She's still in her early career right now, but soon she'll be a Sr. Software Engineer and hit a salary bump, along with all her peers, that will increase the lifestyle expectations across the board. She'll feel how I feel now, with friends buying houses and living in luxury apartments.  
  • I should probably open my mind to thinking how I can achieve those things and not considering a cost-oriented mindset, where I'm cutting those out.
  • Life is meant for living! So how do I accomplish that goal? How much money do I actually have to make? And how do I cobble it up together.

The last few years, I've focused on top of pyramid concerns. Entrepreneurship, working for myself, finding purpose. Even now, thinking about what the next project is, "who" I want to serve, what do I want to do. Is that really the way of business? I think not.

SEO is pretty lame from a brand perspective, and it's full of shillers, but companies need marketers, and marketers need this. Companies pay money to grow, and money can be made riding the coattails of this growth.

So maybe the way I can prioritize what I need to do in terms of work is in terms of a backwards model. What lifestyle do I want to have and then work backwards to achieve the amount of money I need to make to live that lifestyle.

Status doesn't actually matter, especially if it's a trap for working long hours and trading time for it (i.e. a PM job at a sexy startup / Stripe equivalent in '17-'18). It doesn't actually make sense to grind like I used to in terms of hours, unless it's applied productively, and it compounds. Meetings for the sake of meeting are generally useless (operation / task-orientated meetings should just be an email).

Looking for new friends (through work) also doesn't really matter, unless they're friends that 1) are genuinely good people 2) stretch the way you view the world and 3) make you more money. I think these are the types of people I want to be doing business with anyway. I think this of the Spencer Mains, Joel Jewitts, and Dan Buckstaffs of the world. The Ian Burys, Kyle Halversons. Smart, easy to work with, trustworthy.


  • Scope out costs for big ticket items
  • Add them to the expenses spreadsheet

here are the items:

  • improve standard of living: curtains, furniture, clothes that have longevity, pieces that are versatile  
  • travel: cost of buying a home, buying land, exploring places for this purpose
  • grandparents funeral
  • parents retirement
  • ring, wedding
  • buying a home