Naomi

@shreyas So nice to read this Shreyas. Thank you for all that you do :)

An update, 3 years into this next chapter of my career: 3 years ago in May 2021 — after nearly 20 years in traditional tech roles as an engineer and a product manager — I left Stripe to start this 2nd chapter of my career. I don’t write often enough about this stuff, so here’s an update both for long-time followers and new followers: - I absolutely love what I do - What do I do? It’s hard to attach a convenient label to what I do now (and I think that is a good thing) - But here’s how I spend my work time: 60% teaching 25% advising founders & execs 10% writing/content [0] 5% speaking engagements - I work all 7 days of the week — but, I have very high flexibility for when I choose to work and how much I choose to work in a given week - This lets me spend more time with my teenager (he is an only child) than I would have been able to if I had continued doing a traditional PM leadership role after Stripe - I chose to start this next chapter of my career in 2021 because my son turned 13 that year and I realized that I only have 5 more years with him in the house — and by that time, I knew that these 5 years are going to go by very fast - The flexibility I had as of 2021 allowed me to work on a big, overdue home remodeling project (my wife & I agree that for us it would have been impossible to tackle this project if both of us were doing our standard corporate jobs) - This flexibility has also allowed me to take on more of the parenting duties from my wife (it was previously 50-50) — this means that over the past 3 years my wife has been able to spend more of her time on her career than she would have otherwise (she had taken a 5 year career break after our son was born, but has otherwise been working at tech companies throughout) - What about FOMO on all the great things going on in tech right now? The FOMO does show up every once in a while, but dissipates quickly as I reconsider the huge life trade-offs I would have to make to take on a fancy new role at a hot company (or to start a venture-funded startup) - Of course, I still love tech, products, and leadership. I just get to express this love in a different way, more on my own terms. Coaching, teaching, speaking to groups within companies, running communities of product people & founders gives me a lot of breadth (way more than before) and my advising work gives me a fair degree of depth too - Running a (small) business is really fun. I enjoy almost all parts of it (except chasing down invoice payments from corporate clients — with a few exceptions, the bigger they are, the more annoying it is — and Coupa’s supplier portal is an abomination of a product 😄) - My principle is to keep the number of people who work with me for my business priorities to a minimum. Given my business revenue, I could hire 5X the number of people I currently work with. But more people to manage means more hassle, and at some point if I have to manage dozens of people, I might as well just go back to a corporate job - Besides flexibility, being able to choose every single person I work with (both for whoever is helping with my business and the clients I take on) is a life-changer - For instance, I choose not to take on certain advising assignments when I get the sense that we are not naturally aligned on principles and working style (the most frequent example is when a founder tells me they want my advice, but I get the sense from our first couple of calls that what they really want is confirmation / validation, not candid advice on what will make their product win) - Even in this next chapter, there are many options for what I could do (angel investing, VC, real estate, etc.) So how do I choose what to focus on? - After some experimentation in 2021 & 2022, I arrived at this rule of thumb which has worked fabulously for me: I will only focus on things at which I am (or I am confident I can be) world-class - So that means I am not going to try to be a full-time angel investor or fund manager or VC, because I know what it takes to be world-class (i.e. top N in the world) at those things and I don’t have it in me - So for the things I do choose to do, I am always operating in my zone of mastery (or in the zone of challenge, on the way to mastery) - Among other things, this means that what I do and what I offer is extremely differentiated — pretty much impossible to find elsewhere. That means that I don’t have to spend most of my time on marketing / sales and instead can largely focus on making “my product” better, which is what I love most - The combination of these factors means that I absolutely love this second chapter of my career, even more than I did the first chapter of my career - What is my advice for others? My main advice is not about whether advising is great or teaching is great or sharing content is great or whatever else. Most of what I shared above on what has worked for me is because of an infinite string of random events over which I personally had zero control (and therefore can take zero credit for). The only thing I really had some control over is to honestly recognize my superpowers, my weaknesses, and my true priorities — and to act in harmony with these things while resisting the grass is greener bias and not worrying about “getting left behind”. To play my own game and to let others play theirs. And so if you are at a stage in your life where you are thinking about what your next chapter might be and are looking to take anything away from this post, I’d suggest not fixating on the specifics of what I did and what works for me. Instead, focus on identifying your superpowers, weaknesses, and authentic priorities, and then summon the courage to act in harmony with whatever that is. ~ [0] While most people may know me via my public writing (and now my videos), a majority of my work is still very much behind the scenes, visible only to the few founders I work with and the people who join my courses. (It turns out this is not too different from when I worked as a product leader in the latter part of my career. I am quite introverted — I don’t enjoy being in the limelight and I love operating behind the scenes, so I have adapted my working style accordingly)

Attended @shreyas's Managing your PM career course and it was all parts eye opening and extremely informative. The framework that he has created to identify what your goal is and how to eventually get there using the available tools is unparalleled. Highly recommend!

This weekend is for #DriveToSurvive

Best news! Let’s go 🏁

How great is this!

This match has fully gone south #Worldcupfinal2023

No ball is going past Warner #WorldcupFinal

Australia is playing so much better than I thought they would. Such good fielding and bowling. #INDvAUS

@otherwarya I have actually not seen any bashing on this on my social media. Am I following the right or wrong people?

And yes I also know about the PR machinery behind this, pata hai yaar the industry is very small and everyone talks

@otherwarya @need2speak1 Same feedback. Would have loved it if it was longer as well

@need2speak1 Thanks! Nothing longer friend am surprised ppl are even reading this much

In which I interviewed and objectified Kareena Kapoor Khan like some kinda creep 🫡 thedirtymagazine.com/articles/karee… 🔪🥩

Or Sunlight, Colaba

@alfred_lua @lennysan Thanks for sharing this! I’ll get in touch with the organiser for next time :)

@NaomiMLobo @lennysan I believe there is! linkedin.com/posts/cai-shuh…

Scene at the Lenny's Newsletter community meetup #nytechweek event right now (I'm not there, hard to get to NY with a new kid, but the community is representing 🔥)

@anmolm_ This is undoubtedly the most correct description

West Delhi bf, South Delhi gf

Oh thank god he is gone

Sachin is such a bad commentator. Ravi Shastri looks visibly bored. Please take that mic away from him. #INDvsPAK

Pakistan’s national anthem is pretty good #IndiaVsPakistan

Holocaust survivor Gabor Maté describes the Israel 🇮🇱 Palestine 🇵🇸 conflict as the longest ethnic cleansing operation of the 20th 21st centuries… Please watch…🔊

@chiaseedpuddin What a great show.

@ragingdas Facts.

It’s weird how I have trust issues with people who turn their read receipts off on WhatsApp 😂