Three Outcomes

direction, option, outcome

Recently, I spent some time with friends where we ended up talking about career growth. One of whom was at a standstill of which opportunities to pursue if at all. But another of whom offered advice through a pair of interesting lens. One I felt interesting enough to reshare.

When you pursue a new opportunity, especially one where you have strong agency and potential autonomy to influence business outcomes, there are three possible outcomes during the duration of your role.

  1. Success
  2. Failure
  3. And not succeeding

Do note that failure and not succeeding are not the same thing. Failure is when you aim for something and it ends in a negative outcome. Not succeeding is after doing all you that you do, the outcome is still, give or take, the status quo. You haven’t moved the needle for the better or the worse.

At a smaller company, failure is oftentimes business closure. Not succeeding is either a small outcome or the evolution of a fast-growing startup to a lifestyle business with no noticeable impact on the industry. At a larger organization, failure is actually pretty hard. It could be the closure of a department, a re-organization, and very rarely, a negative inflection point for the business. More often than not, it’s not succeeding, which is just maintaining the status quo. Naturally, success is good regardless of organization size.

Failures are seen more charitably at smaller organizations. Larger organizations magnify the echo chamber and press. But in both worlds, they’re seen as your mark on the world. Evidence that you’ve tried. Not succeeding, on the other hand, is often worse at large organizations. Why? Because your career stalls. The more ambitious you are, the worse your career stalling will impact your career. The longer you stall, the harder it is to earn back the momentum. So unfortunately, the worst outcome an ambitious individual can get is not succeeding at a large organization. Death by a thousand cuts.

And the unfortunate truth is that large organizations have a lot of inertia. “Strategy tax” in the words of Bret Taylor. Or as a very senior allocator who recently left their large organization told me: “Some of these layers (at institutions) are there to sap the courage out of your investment decisions.” And you can easily delete the word “investment” out of that sentence.

If you fail or not succeed (not bad, not good), the liability of it not working is put on you the larger the organization. So you take on the tax, burden, career stall if the bad outcomes happen. If you fail at a smaller institution, no one blames you because you took a risk and tried your best and things didnโ€™t work out, they blame the institution.

Photo by Happy Lee on Unsplash


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The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

#unfiltered #58 The Shortcomings of Resumes

resume, computer, laptop

The goal of any professional in today’s economy is to never have to submit another resume ever again.

I swear this isn’t an original line, yet I can’t recall the person nor the setting in which I was told. Nevertheless, whether this was a lucid moment or not, it has been firmly etched into my pre-frontal cortex for years.

Building in public and growing under public scrutiny – be it on Twitter or a blog or another form of social media – is one of the best ways to build rapport and credibility. It’s a photograph. An imprint. Still, and in many ways, permanent. A record that you and others can revisit and reasonably objectify your personal growth. Those data points tell a story. Either you connect those dots personally, or often times, someone else connects them for you.

“We are all the unreliable narrators of each other’s stories.”

If you’ve been following my blog over the past few months, that line will carry a familiar scent. My favorite and the first line I heard from the best film I watched this year, In and Of Itself. When my buddy DJ recommended it to me, he told me only two things:

  1. It’s about identity.
  2. And, “we are all the unreliable narrators of each other’s stories.”

It’d be a travesty if I spoiled the plot now. The best way to watch it is, like most unforgettable experiences, going in blind. No summary, no trailer. If my word means anything, it’d be my answer to the question: What is the one movie you’d recommend someone who just time travelled 50 years from the past to catch up with the way people in 2021 think?

But I digress.

Street cred is built up not by what you say about yourself, but by what other people say about you. That street cred will benefit you much more than a sheet of paper that summarizes your entire career into a single pager with 12-point font. I wrote a blogpost recently on how a pitch deck fails to summarize the motivations, the story, the wins and the losses behind building a business. So, you should always be fundraising. Always be selling. Always be pitching. And as you build champions around you, they’ll tell your story – by referring you to investors, share your product on social media, and sell you for you to their friends. Analogously, a resume for a job seeker echoes the same shortcomings a pitch deck has for a founder. Job-seeking sucks. Just like how fundraising sucks.

If only life were simple

Every person has a story. If not multiple stories. We are each a product of more than one storyline. A narrative in hindsight, when we willingly choose to ignore 99% of the other facts.

One of my favorite internet writers, Max Nussenbaum, recently wrote something quite profound. “We tell ourselves stories in order to live, but our lives arenโ€™t actually stories. If they were, theyโ€™d be poorly written ones: just a bunch of stuff that happens, with no coherent structure or consistent thematic underlines.”

There’d be far fewer cases of self-doubt and depression, if life was as straightforward as a movie script. But it’s not. And neither should it be. It’s messy. But that’s great. Because we can connect the dots however we want.

There are many ways to tell a story. And the best stories are told by others.

And yes, the goal of any professional in today’s economy is to never have to submit another resume ever again. Frankly, after a certain threshold of rapport, you won’t need to.

Photo by Glenn Carstens-Peters on Unsplash


#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. Itโ€™s not designed to go down smoothly like the best cup of cappuccino youโ€™ve ever had (although hereโ€˜s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.


Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

#unfiltered #22 The Lesson I Learned from Purposefully Replying to Spam Emails – Persistence, The Attention Allocation, and a Little Hack I Use

phone booth, spam emails, communication, cold emails

A few days ago, I watched Yes Theory‘s recent heartwarming and inspiring video, Creating a Subscriber’s Viral Job Application. And if you have a spare 20, I highly recommend checking it out. Yesterday, I chatted with a friend about the influx of spam calls these days. So, I thought; now that’s a start of a #unfiltered blogpost.

As a warning, this post is slightly more eccentric than, admittedly, my average #unfiltered blog post.

Prefacing with spam

I used to write this newsletter, Friday Morning Coffee Break, back in college for one of the clubs I helped lead. (Now that I think about it, coffee seems to be the theme for my content drops.) So if any of you subscribers then are reading this post now, this anecdote will be a momentary skip down memory lane.

So, you see, I’m a huge fan of comedy. And 3 years back, when I first learned about James Veitch, I just had to try it out myself. Replying to spam emails. From Nigerian princes. Cold emails from ‘celebrities’. Confirmation emails that require replying to unsubscribe.

If you’re curious as to how he pulls it off, you can check out his Hilarious (yes with a capital ‘H’) TED talks: here, here, and here.

What I did

When I received:

Subject: Save a 80% Off meds delivered discretely to your door

Don’t miss this once in a lifetime chance to get 80% off of a lifetime supply of Viagra!
GotBanq

… my keyboard was ready.

Continue reading “#unfiltered #22 The Lesson I Learned from Purposefully Replying to Spam Emails – Persistence, The Attention Allocation, and a Little Hack I Use”

#unfiltered #19 The Goal of Job-seeking

job seeking

Last night, I caught up with an old friend who has a few more miles on his career odometer than I have. And he shared something quite profound.

“The goal of job-seeking is to never have to submit another resume again.”

In frankness, I’ve never thought about job-seeking in that context. But it makes complete sense. You perform so well in each position that your (former) co-workers start spreading the word about you. “If you need help with [insert subject matter], you have to work with [you].” Effectively, you’re building virality around you through each ‘customer’ interaction being amazing.

And the more I thought about it last night, the more parallels I found. For founders…

The goal of an entrepreneur is to never have to pitch to investors again.

For investors…

The goal of an investor is to never have to pitch how awesome or founder-friendly their firm is to LPs or a potential investment.

And taking a step back, looking at this through macro-lens…

The goal of any professional is to never have to sell again.

You may neither be a startup founder nor a salesperson, but I believe any of us could appreciate the contextualization of our own efforts. What is your endgame? And how can you pave the the most scalable road to your success?

There’s a saying that luck only gets better with success. I’d like to believe that after you reach critical mass and word-of-mouth, you manufacture your own luck.

Photo by Avel Chuklanov on Unsplash


#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. Itโ€™s not designed to go down smoothly like the best cup of cappuccino youโ€™ve ever had (although hereโ€˜s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.


Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!