Lessons from Sabbatical

I’m on my annual 30 day “sabbatical” and if we’re being honest — it’s hard as f*ck.

If you’re anything like me, working hard is easy; it’s the resting that requires the effort. There is a lot of societal emphasis placed on working hard, grinding it out, “paying your dues.” There isn’t much emphasis placed on knowing when to just go to sleep, turn the laptop (or iPhone) off, and go sit in a park with nothing to do.

For the top 1 percenters (that’s you and me), we don’t need prodded to work more. What we actually need, is a reminder to slow down a bit and think it through.

When I say think “it” through, what am I referring to?

  • Your life
  • Your friends
  • Your direction
  • Your legacy
  • Your time (or the lack thereof)
  • Etcetera

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I’ve spent the better part of a decade now paying my dues and working like my life depended on it. This is fine, I’ve developed a particular appetite towards hard work that invites it.

But last year, I made a decision to push pause for 30 days and figure some things out. If you would’ve asked me in April of last year, “What are you building? Why are you building it? How long will you be building it?” My answer would have been as follows:

I have no idea.

How’s THAT for clarity?

In May 2022 I took my first 30 day break and decided, two days in, I would take more breaks and use my brain more. Too much work with your hands threatens the necessary labor that must be performed by your brain.

There’s an old Jewish lesson that loosely goes like this:

  • If you work primarily with your hands, you rest by using your brain
  • If you work primarily with your brain, you rest by using your hands

Many years ago I built a brand called “Smartest Guys In Marketing.” It’s ironic for two reasons:

1st — to be the smartest, you have to think a lot… and I didn’t think that much… I just worked a lot.

2nd — there are no prizes for being the smartest at anything.

Plenty of smart people are broke because they don’t know how to implement what they’re learning. You should aim to be appropriate – which requires a decent amount of intelligence but it does not require being “the smartest.”

But I digress.

This year, I decided to do another 30 day break, and it’s been just as challenging. After two days off, I am ready to FLY. I want to grind. It’s time to work and to push and to… you know the drill.

We are ADDICTED to the hustle.

Look that’s not a bad thing — as long as you know what you’re hustling for and what direction you should be going in. I’m finally past the 2 week hump and settling in, and getting some good gems to take with me to the second half of 2023 and the end of my first strategic year (first of 10 years, of a strategic 10-year plan to achieve some pretty big things).

On my break last year, I came up with a series of lessons to protect me from wasting time. I thought I’d type up a few that are resonating this month and share them with you.

  • There’s enough time to do anything but not enough energy to do everything.

Time = distance; energy = depth.

Time is worthless if you don’t have the energy to savor it — so guard your energy, not your time.

  • Safe money comes from solving HARD problems.

If you’re not a little bit overwhelmed at the thought of solving the problem – it probably is not a worthy problem to solve. Low hanging fruit is usually low yield fruit… if you can solve it quickly, other people can as well.

  • The scariest position to be in is when you’ve won for too long without losing.

It doesn’t mean you’re good at winning — it means you’ve started avoiding new things. If you can’t try something new and fail at it, you will become complacent and stagnant; and someone else will end up owning your territory.

  • The half-life of a business is the amount of time it takes to build it.

Things that work “quickly,” do not usually work for a long time. Worthy achievement comes from consistently deploying effort against LONG, hard challenges.

  • Adhere to a rigorous set of principles and remove anyone who refuses or deviates from them consistently.

Most people don’t even have a set of principles they live by. The ones that do often deviate and tolerate others who deviate.

  • Playing to win is different than playing not to lose.

Don’t waste your time on anything for which you do not feel a deep drive to win, and win completely.

  • Obligation is an energy and usually comes from PEOPLE, not situations.

When you feel like you “have” to do something, pay attention to who is behind it. A situation only has power over you when some part of your identity or happiness is dependent on a person involved in the situation.

  • You cannot re-purchase a chunk of time from yesterday that you did not enjoy — when it’s gone, it is gone.

Time repeats; moments do not. At the end of your life, if you were given the option to go back and live it all again — what choices would you make differently? Go ahead and make those choices now.

This gem, by the way, is what caused me to re-organize my time so I could be present with my family. At the time, my family consisted of my wife and my daughter.

Now we also have a son, and I have no regrets in choosing to spend more time with them than I used to. Here he is – a strapping 4-month old ready to take over the world.

  • Go all in on people — people OUTRANK opportunities.

Opportunists develop a reputation and it’s not a reputation that you want to have. If you become known for something, become known for being an advocate of people.

Slow down and pick your people well — this means partners, friends, employees, colleagues, connections, all of it. Every person you surround yourself has a ripple effect.

  • You can do 10 times as much as you think you can, but it will probably take you twice as long.

Don’t stop in the middle. Most people end up paying the price and quitting halfway through. They pay half of something, then get nothing for it.

  • Winning doesn’t need to happen quickly, it needs to happen consistently.

It’s easier to go from level 3 to level 300 than it is to go from level 1 to level 3. Mastery takes a lot of time. It’s worth it.

And here’s one from this year’s sabbatical:

  • You get power from what you must go through — not from what you “narrowly avoid.”

Every failure you “narrowly avoid” accrues an interest payment (often in the form of insecurity, guilt, doubt, etc). Failure is not something to fear, you should aim to prevent it by being prudent, disciplined, and strategic. But you should not run from it.

If you develop a bias against failure or worse, a fear of failure — you guarantee long term failure.

Hope you’re enjoying June…

What are your favorites from this list? And do you have any you’d like to add?

Talk soon,


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