Week 7+8: A plan for a plan

In mid-Feb, I experienced what steady state chill felt like, and was beginning to like it. And I did more of that in weeks 7+8, which I’m still enjoying. Looking back on Feb, though, I think I can see a plan for a plan (for what I’ll call post-sabbatical) beginning to form.

Several threads came (and are still coming) together that cause me to say this. The first one: more conversations with friends and former colleagues who are on a break from their job, or very seriously considering one, resulting in me trying to help them make a plan. Esp. those who knew up front that they were taking fixed duration of time (usually, 4-12 weeks) off, we talked a lot about how to make it count. The summary of this problem solving was that one needs to decide, in that order, where one wants to live, what function/industry/type of role (very broadly) one wants to do, and lastly, the specific company or set of people one wants to engage/ work professionally with. Often the hope is that a sabbatical will prompt one to revisit all three, and seek answers to the “why” more than the “what”.

In my case, the answer is becoming clearer, especially since I’ve gotten time recently to turn the whys over in my head a few times. Location-wise, we quite like London, and have a lot of Europe travel ambitions pending, so that’s where we’ll stay by default [1]. More and more companies are opening up to distributed talent, esp. in new areas like web3, so this location choice definitely feels less constraining that it might have say pre-pandemic. I can work with anyone in the India ←→ New York time zones, which covers a LOT. Function/industry-wise, I know I love thinking tech-product, and like working at the intersection of software tech and building a business. My recent, very nascent attempts at playing an advisor role to smaller companies is helping me realise which of my skills might be transferable and valuable to smaller companies (e.g. problem structuring, solution rigour, org, metrics and process) and what I’ll have to learn/ relearn (e.g. mostly everything else, esp. dealing with severe talent constraints and shipping based on mostly gut). I also had a chance to revive some skills, such as thinking actively about sales and marketing, that I was afraid were getting rusty working in deep-tech, and it felt good to get into back the groove and think on those problems. And lastly, people/company — that one I’m explicitly not trying to nail down too soon. More on that later.

The second thread: I ended up speaking with a few folks who, after successful careers in full-time jobs (10-12 years, not forever), took up freelancing full time. After hearing them talk about the joys and worries of being a freelancer, my summary takeaway was that it is not for me for now - I don’t want to take on the variability, it has limited upside, and I don’t value the freedoms as much. BUT, in the very near term taking on a few consulting gigs might be a good way to get my hands dirty with tech problems, work with new people and assess a potential fit. Oh and also, some money wouldn’t hurt. I’ve missed two paychecks now, and am definitely noticing it. No fuel to BTFD :). So, I’ve decided to be open and deliberate in taking on small time bound projects, as a stepping stone to the aforementioned. It’s a different skill and mindset to price one’s time in days and weeks - much harder than pricing per year, which is the only experience I have. Something new to learn here too.

The third thread is some meetings with seed and early-stage VCs that came about through friendly introductions. These conversations forced me to articulate what kind of team, problem and product I’d want to work on, if I could wave a magic wand. The answer is admittedly still high level (and one of the unknowns I’m exploring in the sabbatical) and I touched on some aspects in thread#1. It also made me start thinking of the question “What idea and team meets the threshold for me to want to raise money to pursue it?” and a corollary “if there already exists something close, will I join?”. On the latter, my exposure is very low, and so I gratefully accepted the offer to sit in on a few deal flow meetings so that I could get a glimpse into what others were building. I’m very keen to make this a fair exchange, by contributing questions, problem-solving help, time and advice as the case may be. I’d have said money, but… remember what I said in the previous thread [2]? ;)

So, that’s where things are at. The “plan for the plan” is to be more deliberate in meeting companies, meet many more of them, very deliberately spend time a few of with them, and then deliberate on the findings [3].

In other happenings since the last update, I’m doodling on a no-code implementation of an idea I had for a B2B tool for real estate agents. Inspired directly by seeing my own agent at work in a recent transaction. If I can help her build something to save time and streamline her work, maybe others will use it too.

And, Niki got a YouTube channel.

Like, Subscribe and Hit the Bell Icon here!

Footnotes:

[1] Never say never, who knows what opportunities may come by!

[2] Also, there is an absolute glut of angel, seed, etc capital floating around. I’d need some serious conviction that I’m investing with an edge if someone’s asking for my money vs. that from professional investing houses.

[3] I got a Wren-and-Martin-esque kick from using one word in three different forms in the same sentence. Couldn’t help myself!?