~/diary/Open Waters
Updated Jan 25, 2022

🖊 Open Waters Tuesday, Jan 18, 2022

This entry is an exercise in clarifying my goals for the year and the longer-term trajectory for my career. If you are reading this, keep in mind I am writing for myself. Publishing the result helps me keep myself accountable.

At the start of my sabbatical year, I made a public declaration of my intentions for the year. In retrospect, I am really glad I did! Those goals served as a guiding light throughout the year, when facing choices like “should I learn _?” Or “should I start project _?”. They gave me focus, removed some options, and decreased the amount of self-doubt ("Is _ a waste of time? No. Practicing this is one of the objectives of the year!").

2021 has been a year-long experiment in working for myself. I quite a few doubts at the start of the year:

After a year of experimentation the answer is a resounding yes.

I enjoy having a diverse set of opportunities available. I enjoy creating my own mixture of multiple involvements, roles, projects. I enjoy having more control over my schedule, more freedom to set direction and proceed as I see fit, on my own path. Strangely enough, I enjoy making less money, because every dollar it’s more valuable, and I enjoy it more!

The path ahead of me is clear: I don’t want to go back to being an employee for now. The 10 years in big tech were great, but I want the next 10 years to be different. (Credit where it’s due: I am where I am with the luxury of a career change, thanks to those 10 years in Silicon Valley).

So why leave the safe harbor of Silicon Valley, the home of my industry? In 2021, I got a taste of leaving the shore and exploring some open waters. 2022 is the year I start venturing out in deep, blue waters on my own.

I’m scared of going off on my own like I’m scared to jump into deep seawater. I know it’s mostly irrational, but it’s very real.

I just need to jump in.

Here are my guiding principles for the year 2022.


… worrying about money

I am very lucky, my craft is in demand. Work opportunities are plenty, and they pay well. If ever need work, I will find some in about 5 minutes. I can afford to be picky, even if choose contracts and projects based on personal preference rather than salary, I will still make good money.

… being a small cog in a giant machine

For years, it felt great to contribute (in small part) to world-renown products. But lately, the magic was gone, it just felt like I was helping a giant corporation become even more gigantic. On the other side, seeing my little tacky projects and experiments used and appreciated has made me truly happy. I should optimize for happiness, get better at building small cute things end-to-end.

… trying to start a big project

I tried for all of 2021 to start a serious/large project, from my rotating wishlist of projects. I couldn’t. While working for others as a freelance is easy, working truly for myself is hard. Something is amiss, I haven’t quite figured myself out, but it’s not going to happen overnight. Let’s pause this for this year. In 2022, focus on doing a good job with the existing commitments. They are diverse and interesting. I will learn a great deal. Only little and toy projects allowed, and hackathons.


… Balancing of work and play

I don’t miss being ‘on the clock’ 9-5 Monday to Friday. However, the upside of that was a well-defined boundary between work and not work. Today that line blurry. Gradually I found a new equilibrium where I can work more or less when I feel like it. It is way more than 40 hours a week, but almost all of it is enjoyable because I’m choosing to work. I have the freedom to spend time with family and friends whenever I feel like it. The non-working hours give me the energy and desire to be more effective during working hours. I should continue liberally allocating time (both planned and unplanned) to enjoy life, whatever that means in context.

… Making space for serendipity

Consistently, the moments where I was further away and disconnected from my computer, were the moments that yielded the most light-bulb ideas, the most profound realizations, the most surprising ah-ah moments. Similarly, exploration in the digital world – going down rabbit holes not immediately related to my projects – yielded invaluable treasures. I should continue giving myself the freedom to be fully present in the moment, and explore serendipitously.

… Building my social network

In 2021, I’ve had 1:1 over 100 virtual meetings with people I had never met before. It takes work, energy, time to make these encounters happen. And it’s absolutely worth it. 100 out of 100 were inspiring and positive, 100 out of 100 made me walk away feeling enriched, inspired, or learned. I should continue setting up impromptu meetings with people I find interesting, whenever there’s a good occasion. Continue with a balance of new internet friends, and old IRL friends.


… Being more selective with my involvement

I ended 2021 oversubscribed on projects/collaborations/engagements. Biting more than I can chew is not good for anyone. Stress reduces my efficacy, and sooner or later I need to drop something. I should start being more selective, keep a clear list of active projects, and not add anything willy-nilly. I need to start passing up on more opportunities and being ok with it. Don’t let FOMO make edits to the list. A corollary is: be honest and clear with yourself and with others regarding how much time you can dedicate to something.

… Better define priorities

I often feel like I spent too much time on something that was not important at all. Often is due to detours, yak shaving, procrastination, distractions. I think the first step is better priorities: recognizing that something is not worth the time I’m giving to it. I want to get better at prioritizing and planning so that fewer hours are wasted.

Other goals

Things I’d like to level up over the next year.

Skill: graphical interfaces, front-end development

In ~20 programming, I have almost zero experience with front-end and user interfaces. This holds me back: the only thing I can make are for other developers (libraries, APIs, infrastructure, …). Going forward, I want to build things usable and useful to a wider set of people, not just developers. To do this, I need to start learning some UI tools, technologies, and methods.

Skill: non-computer

In large teams, specialization and deep narrow focus is a strength. But out here, I’d like to level up a broad set of skills I’ve never really used before. Such as:

Skill: Scrappy development and Hacking

In large-scale systems and infrastructure, a technical mistake can cost the company millions of dollars per hour. Every decision has ramifications, dependencies, side effects. Issues are multi-dimensional, and tradeoffs are non-linear. So for 10+ years I’ve learned to tread carefully.

With the kind of project I work on these days, the result is I think too much before doing. This kills scrappy projects and ideas because I get stuck in the overthinking phase. I am gradually becoming more effective at hacking things together. I am having a great deal of fun, and falling back in love with programming. More small/just-for-fun/throwaway/fun projects are the key to getting better at this.

p.s. the same applies to writing – way too much editorializing, where I should just throw down whatever comes to mind, then make it better iteratively, or next time.

Skill: Deep focus

I’ve gotten better at working in full focus on a particular task (a.k.a. being in the zone, flow state, etc). I could do better: getting there sooner, staying there longer, or more reliably, giving focus to diverse projects, etc. I should keep observing what works, and try things to make it better.

Goal: Find a technical mentor

Good mentoring is equally valuable to both people. I would like to find a mentor willing and happy to spend time with me regularly (even if it’s just for an hour a month). Who am I looking for? 20+ years of industry experience, ranging from employee to funder. Background in systems engineering (or digital art, architect, applied scientist).

Other principles

Invest in learning

Even if the subject is not of direct practical use. If you have the interest/energy to learn about something, go for it! In practice: take online classes on things you don’t know, read books you normally wouldn’t, go to conferences and meetups.

Prioritize good for the world over profitable for me

This goes by many names like (golden rule, karma, …), and it is the base for any decision. Focus on helping others with pure intentions, this makes the path ahead clear, full of joy and treasures. The ‘pure’ bit is important. I should be vigilant and recognize if my intentions are less than pure. If this is a transaction and not a gift, be honest and transparent about it.

Look ahead

3-year target
5-years target
10-years target