How to Grow Your Luck

How To: Faceplant Your Sales Demo

Back in the spring I had a decent shot at a sales engineering job with a tech firm called Akuity (opens in a new tab). I'd gotten through a few interviews, put together a solution proposal that I thought was stellar, and booked a live presentation to walk the Sales Engineering team through it. I did a dry-run earlier that day and all was well.

Minutes - yes, actually, literally a few minutes - before the meeting, an access token on which my demo depended expired. I didn't realize this until I was sharing my screen with the people I was trying to impress (I either missed or didn't get any notifications about it), at which point I got to spend about half of the already short time scrambling to get the thing working again while they watched. One of them helpfully tried to salvage our time by asking me some hypotheticals while I unexpectedly demonstrated my troubleshooting skill & speed.

This was not helpful.

It was not fun.

I did not get a job offer.

In hindsight, I should have rescheduled, should have rehearsed a backout spiel, but in the heat of the moment it seems I decided the only way out was through.
Every now and then, I guess the obstacle really isn't the path.

¯\_(ツ)_/¯

I told that story in a previous post as one of the reasons I paused looking for a job. I wanted to tell it again, because I've been chewing on a concept for a couple months and that demo going up in flames... okay, well, it's not a great example of it but I can't think of a better one, and, well, it's my blog so I'm processing my traumas whether you read it or not. The concept in question is the luck surface area.

(Don't fear. I manage to beat the example back into submission later on. It'll all come together.)

Luck Surface Area

The Equation

The phrase "luck surface area" has been going around for a while. Jason Roberts (opens in a new tab) seems to have coined it back in 2010:

The amount of serendipity that will occur in your life, your Luck Surface Area, is directly proportional to the degree to which you do something you're passionate about combined with the total number of people to whom this is effectively communicated.

(His post is very short and worth the read to get his whole idea.)

Roberts illustrates luck surface area as a two-dimensional product of these two numbers:

• how many interesting things you do
• how many people you tell about these things

Do interesting things in private and the second number is zero.
Talk constantly but do nothing and the first one is.
Failing to do either produces an area of zero. A square with one side of length 0 has no area.

Do both and you've got a square that can catch luck.

Katrina

I have to shout out Katrina Romulo (opens in a new tab) and her New York travel video for bringing the concept to my awareness. She'd been laid off two months after the proudest project of her career, and in the meantime had developed enough travel anxiety that she was saying no to most things. To break out of her funk, she booked a week in New York - with no plan whatsoever - to see if luck would find her.

The first two nights she didn't sleep at all, was having a gnarly time, and she came pretty close to changing her flight and going home.

But she realized something: she'd been seeing things & going places but she hadn't actually told anybody she was in the city.
Doing, yes. Telling, zero!

So she texted her cousin, and like magic the week filled itself in - museum days, dinner with a print studio she'd taken a workshop with in Manila years earlier, an aunt texting about a Broadway show that night, a print of something she'd drawn on the plane that showed up in the mail weeks later. As she puts it, none of it was earth-shattering, but it was all good. She went home feeling like she'd been living instead of just existing, which is exactly what she'd hoped for.

Okay neat, that's the two numbers forming a square that 🌈luckdrops🌈 can fall on. Look at what her luck landed on, though: a cousin, an aunt, a studio she'd met years before. Everything's a something that existed before she boarded the plane. Whether she realizes it or not, Katrina's cultivated a 🌳🌻substrate🌻🌳 that was fertile and ready to receive the luckdrops.

100 Days of Solitude (or so)

For four straight months after losing my job, I applied for new jobs. Full-time. I paid for access to a few remote job boards, and spent my days writing cover letters, tailoring resumes, researching companies & their platforms, prepping for interviews, getting rejection letter after rejection letter (many identical in wording from wildly different companies), and zero useful feedback from the interviewers.

More than 75 targeted, good-fit applications. Four months.

My brain was oozing out my ears, and I had very little to show for it.

Job applications are doing with the telling switched off. One recruiter sees it, maybe a hiring manager, and then it goes in the forever box. Nobody outside that loop can see any of it, so nothing outside that loop can land on it. Four months of full-time effort with a surface area of roughly one.

And then the sales engineering interview. That was luck landing a hit on a small surface, but there was nothing to catch that luckdrop, hold it, nurture it, until it could bear fruit.

Let's abuse a metaphor!

I wrote this on an index card a while back:

putting in the work does two things. It increases the surface area for luck to land on, and it prepares a substrate that will catch, hold, and grow the spark when it hits.

Right, substrate, ok. Here's a metaphor: Seeds land everywhere when they're released. Some will land on concrete, some on rocky ground, and some will land on good soil. The seeds' success is strongly related to the soil quality. This is obviously not a novel idea (opens in a new tab).

Let's now whip the metaphor into our service: We're farmers and we want to grow crops. Cash crops, food crops, balloon crops (opens in a new tab), whatever - we want crops that sprout, grow, and produce a harvest. In our metaphor, seeds fall randomly from the sky like rain, and will grow into crops given good soil and care. But! The seeds produced by crops are themselves unable to sprout & grow. If they could, this whole thought experiment falls over. Look, the metaphor's crying now, poor thing.

We could consider our luck surface area as the amount of land we own as a farmer: if we want a larger surface area, we buy or seize or embezzle more land. More land means more seeds will fall on our holdings, which means more harvest in a given season. That's as far as Jason Roberts' luck surface area definition goes - more area means more luck.

I think there's more to it, though.

My sales demo had plenty of surface area. It didn't have a good substrate: in this specific case, some combination of safety fallbacks that would have had a better chance at saving the broken demo and ultimately my candidacy. Good loamy soil that would have held the seed of luck through stormy weather: backup slides and screenshots, a rehearsed "the demo is broken, here are our options right now" script, confidence in rescheduling the demo, &c. Any one of those and the exact same luck would have stuck. I'm not beating myself up over this, mind you. These are things I didn't know, or at least didn't think of. I'd never done a sales demo before, never considered its exigencies & responses. Now I've learned, and next time a demo fails I'll handle it better. Thus have I cultivated the substrate.

The Third Dimension

This is my contribution to the luck surface area idea: A third dimension of substrate. Here are three different luck surface areas, each the same size, knocked over onto their backs to show their substrates from the side view. Each can catch, hold, protect, and nurture a different amount of seeds.

Your luck surface area is only as good as its substrate. Cultivate a good one.

Short Commentary: Tradr's Luck Surface

On August 27 I posted (opens in a new tab) about Tradr (opens in a new tab) on LinkedIn. I had 264 followers at the time and never a post with more than a few hundred impressions.
The post got 141,000 impressions and reached 96,000 people. 968 of those people clicked through to my profile, and 24 followed my account. By any measure, that post was a good luck hit.

The substrate caught a good chunk of that. Anyone who clicked got the live app, a working registration page, a docs site, a public repo, and a release pipeline that shipped a fix 5 days later. The first bug report came in within a day, and got fixed because I have a tight development cycle that lets me deploy quickly with reasonable safety assurances. I spent a lot of time and effort on my development loop, delivery staging, CI/CD pipelines, visibility/monitoring, etc. to make sure I could properly manage the application stack and supporting infrastructure from day one.

The substrate dropped a lot too. Tradr has 26 new users. 96,000 people saw the post, and they ultimately converted to a Tradr account at a rate of 0.027%. Yikes. I also didn't do much to cross-pollinate this website into the Tradr visibility, and I hadn't set up the newsletter yet.

The Tradr-specific substrate was in good shape and did some work. The personal branding audience-building substrate wasn't ready, and sure enough it didn't catch anything.

More and Smaller Bets

We can't pick which surface the luck lands on, which is why another one of my cards says more and smaller bets: I don't know which ideas will work until I try them! So, I'm trying to do as much as I can. The outer world will tell me which ones work (by them working), and my inner world will also give me feedback about what's working for me.

What's landed on you this year that you weren't ready for? Reply if you're reading this in your inbox - I respond to every human.