I think one of the things I have a perpetual obsession with is career optimization. It feels a lot like poker. There is no magic playbook, or a clean meritocratic path to it, at least not anymore.

Luck is taboo, though, and it takes a certain level of maturity to come to terms with it, because it is the variable that never really leaves the equation of career and life.

So instead of learning the next AI tool or chasing the next gig for a 5000% hike, why not focus on improving your odds?

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Do, tell, or both?

I’m a fan of mental models. In a highly unpredictable world, even an NPC needs waypoints and checkpoints to find the most efficient path to the destination.

One mental model I’ve come to really respect ever since I became a manager is doing and telling at a 50:50 split. I’ve seldom seen only talkers or only doers succeed for very long, but a combination of both almost always does.

So if you were to plot “Do” and “Tell” on an X-Y axis, the slope of it is luck: the right amount of doing combined with the right amount of telling. That’s how you create any sort of luck, whether it is getting hired from shitposting on X or LinkedIn, bypassing the snake pit of HRs to talk to hiring managers directly about a job, or getting paying users. The list goes on.

In my world, doing and telling has gotten me some pretty interesting roles to work in. The latest one involves managing a team and helping build a product category. So if I look back at the career bets I made:

• job #1: Series C startup -> founding product marketing team member -> scaled it across India and the US. First touch with enablement, no-code tools, design, and product.
• job #2: IPO company -> started the PLG motion -> scaled it to half a million dollars -> learnt the nuances of scale and company politics.
• job #3: Series A startup -> helping build category -> managing a team -> increasing ACV, win rates, pipeline volume and quality, and founder brand.

The point of telling you this is simple: I’ve never posted much online, but I do a lot of doing and telling internally, and that has helped me get into whispered roles, the kind that don’t really have job postings. So you do not necessarily have to be a social butterfly to increase the slope, or the surface area, of luck in your life.

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What’s after luck?

Destiny.

Luck is inherently probabilistic in nature, but let’s face it: gambling takes a lot of energy, and over time your risk appetite reduces as you grow older. There is a short window to make anything meaningful happen before your destiny becomes clear to yourself and to the market.

So how do you become what you are destined for?

1. To begin with, don’t necessarily job hop for hikes. Or if you’re running a business, don’t make pivots a habit. Asymmetrical bets have asymmetrical rewards, and the common denominator is persistence. Persistence to your craft, to yourself, and then to the company you work for, aka tenure. Become unbelievably good at what you do, create side projects, and make sure you have more than 10 all-weather industry friends. It’s easier to make friends than people think. Ask good questions and make keen observations. That’s one of the fastest ways to earn respect and credibility with senior folks.

2. There is no substitute for action. There is a lot of grey area here, but let me condense it: action is both art and science.

   1. Art, because you have to develop taste, bring polish to your deliverables, avoid bringing one option and instead always present alternatives with trade-offs, follow through without being chased, and spot purple cows, which is just another way of saying spot what others miss.
   2. Science, because the boring questions still decide a lot. Did you do what you said you would do? How do you correct yourself when you’re wrong? Why go with tool X instead of Y? How will you automate this and do it better next time?

Your work ethic is the single biggest lever you can pull that determines your destiny. Work for the love of work, and the rewards will come in due time.

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Work-life balance, not having money, not having access to the right people, and other BS

Here’s what I tell, train, and coach my own team on:

Everyone has constraints. But like players on a sports team, you have to do a lot of painful soul-searching to find your superpower, or your edge. I often ask this in interviews too: “What’s your superpower?” It could be anything, making the best pancakes, knowing exactly how a rotor works, literally anything.

It’s a real signal on obsession, depth, and something a person spends serious self-directed time on. Those are transferable skills.

My team, a designer and a GTM Engineer, are getting quite skilled at adjacent skills because of AI. I wrote about that here. I’m quite big on them building their personal brands and doing a lot of do and tell on the internet. Here’s how I’m coaching them:

• Document every single project you shipped through the lens of the business problem you solved. Context is shared transparently with them, and I weigh managerial and project decisions openly in team calls. Nothing meaningful sits on the other side of the boundary. Everyone is an equitable stakeholder.
• If documenting is a pain because time on weekdays is scarce, literally open drafts in Gmail and write bullet points. Or maintain a brag doc that you update weekly.
• Take real screenshots of what you built, the constraints you encountered using your toolsets across projects, and introspect hard on what worked and what didn’t. Identify patterns over time and take strategic calls every quarter: retire a tool, redefine a process, or establish a different way of communicating with stakeholders.
• The only true way to grow is to compound. All other growth is incremental and linear. Flatlined careers are dead careers. So compounding is easy, at least in theory: self-review and introspection.

You don’t need access to specific people, an executive coach, the right computer, or the right tools. Work-life balance is a great fever dream but with no meaningful implications.

You don’t even need the right curriculum. Lord knows I’ve spent a lot of time curating one for myself over the past decade. But you’re no professor. You’re a doer. It makes more sense to tactfully solve the problem in front of you and learn from it.