Nights, Weekends & 3 Phases Of Success


Finance twitter has been buzzing this week about what it takes to be successful. Work 80 hours a week in your 20s? Work nights and weekends? Yes and yes. Successful people push all the time, 25/8/366. Let’s not pretend this is bad or that everyone must do it. Let’s also clarify what we mean by success.

[25/8 is a segment we use to discuss workaholism, entrepreneurship, and possible salvation.]


Career success is primarily based on metrics like money, expertise, and credibility. Life success is different, and those metrics are much more personal.

But career and life success are interwoven. So here’s my take:

Career success requires at least 10 years of being on call nights and weekends on top of a normal work schedule. This will win you above average rankings on money, expertise, credibility, or all three.

This isn’t a bad thing for those with outsized ambitions.

Not everyone has outsized ambitions, so not everyone must do it. It’s just what many envision for ourselves.

If you have the stamina to put in 10+ years at this pace, it’ll play out in three phases:

1. You’ll taste career success through some combination of money, expertise, or credibility.

2. You’ll gear down career success ambition and gear up life success ambition.

3. You’ll pursue phase 2 to define life success, then settle on a blend of 1 and 2.

I’ve recently entered phase 3.


I’m 20+ years into a career of being on call nights and weekends. Four years ago I started making peace with some life goals I’d achieved with my wife.

Happy family, happy/healthy child, living in two places we love the most.

I started working less to enjoy family, rethink corporate soldier-ism, and define life success.

It didn’t last long though. Approximately 2 years.

Then my career success ambitions took over again, but this time informed by life success ambitions.

What if I could sustain this life success achieved so far by transitioning career success from corporate soldier to entrepreneur?

What’s happened to me as an entrepreneur is no surprise: I went back to being on call nights and weekends.

But it’s been different so far, for two reasons:

1. Ironically, working nonstandard hours lets me control my schedule.

I spend time with my kid during his hours. I have time to attend to my stupid health problems. My wife and I work where we want (including our 2019 London summer experiment to test this theory*). And I make time to research and write about my work, instead of just being a taskmaster.

2. I can access clients on their time.

All C-Level executives and senior mangers work nights and weekends. Weekdays are mostly for selling, building, servicing, managing, and putting out fires. But nights and weekends are when most of us think and make big decisions.


Note the language I’ve been using: Being On Call Nights and Weekends.

Here’s 3 critical differences between being on call vs. working nights and weekends:

1. A ‘working nights and weekends’ mindset is servile to some outside force like a boss or client. Overly servile folks are rarely liked by colleagues and most burn out.

2. ‘Being on call nights and weekends’ means openly admitting your ambition and acknowledging your blended lifestyle. Doing so makes you less moody when after hours work arises.

3. Being on call doesn’t mean you always work. In fact, if you approach it openly enough, you can be better rested when it matters most.

My wife is great at this. When needed on nights or weekends, she’ll pause to focus and finish some work task without any mood change. Then her head is clear for life stuff.

I guarantee that anyone you admire most — in work or life — is getting shit done nights and weekends.

And they all share 2 traits:

– They’re on call 25/8/366.

– They’ve been at it for years.

But don’t let this long game overwhelm your 2020 planning.

Instead, remember what Bill Gates famously said:

We overestimate what we can do in a year and underestimate what we can do in 10 years.

Good luck with your work and life ambitions this year.

And hit me up with your stories!

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3 Ways To ‘Crush It’ Without Being An Asshole

Watch me smash this 4am smoothie. Then watch me crush this 25 hour day.

– *My wife has a global job that enables/requires her to work anywhere. She’d been waiting years for me to be in a position to do the same. Our London summer was the first major experiment to both work successfully from anywhere. Admittedly, it was very difficult for me to manage time zones with mostly U.S. customers. More on this in a future 25/8 installment.




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