What a $10,000 day looks like

There’s a hard path. And there’s an easy path.

Let’s take a peek into the world of finance, where this path can be approximated with a number, known as The Sharpe Ratio.

The Sharpe Ratio is calculated as follows: Investment Return divided by Investment Volatility.

(Finance geeks, please allow me to take some liberties in the nuance of the calculation)

The ratio is best illustrated with a few simple graphs. Here’s a $100 investment turning into $146 over 5 years. You’ll notice that the path is very volatile. (Or as my 3 year old would say, “That’s a lot of ziggy-zaggy.“)

This investment would have a very low Sharpe ratio.

Here’s a different investment that also yields $146 over the same period. With a very little ziggy-zaggy.

This investment would have a very high Sharpe ratio.

Though they both land in the same place, it becomes quite evident which investment you would prefer.

The first one is a bit of a cluster-f*ck. Its highs and lows mess with your emotions. One’s monkey mind could lead you to sell at just the wrong moment. Just looking at the chart is exhausting.

The second investment is like riding a Tesla. It’s smooth, effortless, and outright enjoyable. (Plus, that Whoopie cushion feature!) You look forward getting inside. And once inside, you never actually feel like you’re driving.

Here’s the bad news: In the world of investing, the second investment is somewhat imaginary. In general, as the returns go up, the effort (or volatility) must also go up. The market is efficient and rarely allows for a free lunch.

But what about in your career? Is it possible to maximize your career while preserving that Tesla-like ease and flow?

Please meet two of our friends. On the right, you’ve got Ten Dollar Tim and on the left 10K Tina. They’re both in their late 30s.

Tim’s a Manager at Deloitte and Tina runs sales at a small design agency. Both are hard working and well-rounded professionals who are seeing their careers accrue with success.

Let’s take a look at a typical Tuesday for each of them.

Tuesday early morning

Ten Dollar Tim starts the day a bit groggy. His heavy pour of the Monday night Pinot had him up a few times in the middle of the night tossing and turning. On one of those bathroom visits he mischievously pulled up an email from his client in Japan, which set his set his mind off to the races.

His alarm goes off at 6 am, but he’s going to skip home workout today – opting instead for two huge mugs of coffee to jumpstart his brain. His youngest wants him to color with him for a few minutes, but he shushes her away. He’s furiously bouncing between emails, his Twitter timeline and his low-grade headache.

$10K Tina on the other hand, wakes up at 5:30 am naturally. It’s been years since she’s used an alarm and her body just wakes up after 8 hours of sleep. She heads over to the love seat in her bedroom to do a quick 10 minutes of meditation then with her running gear neatly laid out by the door (ahem, Keystone habit), she goes for a quick run. (Her phone – still on airplane mode – prevents her from checking both the news and Slack.)

Showered and back at home, Tina sips her hot tea as her son regales her with a dream about flying dragons and sorcerers. Tina does this crazy thing where she only drinks coffee every other day – her husband thinks she’s nuts.

At 9 o’clock, both Tim and Tina head to their home offices to kick off their days.

The day begins

Ten Dollar Tim has been responding to emails on his phone from the minute he got out of bed. He’s obsessed with “being responsive” and Inbox Zero (aka other people’s priorities) defines how he plans his day.

He’s got a big sales presentation deliver to a client on Friday. Feeling a bit behind, he hops on a quick Zoom check-in with his analyst. But the agenda-less meeting doesn’t actually advance the project. No one knows what the next actions are, and who’s responsible for them.

Tim scribbles some notes on the back of an envelope and sends himself an email to remember a pertinent statistic. (His analyst, rolls his eyes as soon as he hangs up. He expects Tim to call back frantically in 4 hours looking for that statistic.)


As the call ends, Tim sees an email from his accountant that he needed to get all his W-2s and 1099 tax forms submitted by last Friday. “There goes my morning,” he whispers under his breath.

It’s barely 11am, and he feels the day running away from him.

Meanwhile, $10K Tina opens her laptop (and checks her messages for the first time) at 9:30. She confirms a few meetings and conducts a 10 minute Slack stand-up with her team.

Tina’s got a tidy Moleskine notebook, where she quickly scans her morning’s tasks grouped into two categories: High-Leverage and Low-Leverage. She aims to complete two $10k tasks before lunch: Update the onboarding manual for her new hire and pitch their upcoming launch to the Wall Street Journal.

She does a quick scan of Slack, and turns off her laptop’s WiFi. And she fires off her 25-minute Pomodoro timer to keep herself accountable.

The post-lunch slog

By 1pm, Ten Dollar Tim has finally sent all his paperwork to his accountant. His analyst wonders why he hasn’t heard from him; their Friday deadline is quickly approaching and they haven’t even sent the first draft to their big boss.

Tim aims to reboot the day with an Americano, but he can’t get himself to focus. He sits down to prepare the outline for the presentation, but somehow ends up arguing on Twitter with a high school friend about why Gamestop stock is overvalued. (He did buy some put options on Robin Hood after all.)

As the day winds down, Tim comforts himself by celebrating one of the day’s wins: he did hit Inbox Zero (for, a few hot minutes.)

Tim remembers he owes his analyst a response and fires him a quick email “Let’s catch up tomorrow on the presentation.”

(The analyst hears “Get ready for a fire-drill on Thursday night.” Thankfully, remote work has made interviewing easier – he’ll be gone within the next two months.)

Meanwhile, $10k Tina finishes lunch with her 7-year old son. One of the unexpected perks of online learning is these shared moments throughout the day.

(To be clear though, Tina won’t miss homeschooling once the vaccine gets here.)

She goes for a short walk around the block to clear her head and buckles down the rest of the day.

Tina tries design her day according to her energy level. As a morning person, she knows she has to get her high-leverage work done by noon and then saves her afternoon for Zoom calls and low energy tasks.

She’s batched 3 of her one-on-ones with her direct reports to begin at 1:30. Before each one, she flips open her task manager and filters by each of their tags to identify what’s outstanding.

After the 1:1s, she’s wiped. For the next hour, she responds to Slacks and emails and has time for one other low-leverage task. She pulls up her task manager again: prepare tax forms.

The wind-down

Ten dollar Tim heads home (aka his living room) exhausted and quietly embarrassed about how he spent his day. (“Damn tax forms!”) His daughter greets him with puppy dog enthusiasm, but he feigns interest.

“Tomorrow, I’ll be more present for her” Tim reassures himself. He rifles out a few more emails, to hold the line on Inbox Zero. He opens the fridge to get a seltzer and there he sees it: a delicious IPA to punctuate the day.

Meanwhile, $10K Tina heads to the living room to join the fam. But before she does that she does a quick brain dump to close any open loops. She jots into her notebook a few miscellaneous tasks and flags her two $10k tasks for Wednesday.

There’s one outstanding item that she’s waiting on that may require her attention in the evening – but since she doesn’t have Slack on her phone, her colleagues know that they can text Tina for a quick sign off. As she hears the boys roughhousing downstairs, she shuts her laptop for one last time. She’s overcome with a deep sense of satisfaction and gratitude.

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