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Outsmart the Hustle

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“Mortality makes it impossible to ignore the absurdity of living solely for the future.” – Oliver Burkeman

I still remember, more than 10 years ago, feeling equally terrified and excited about walking away from a lucrative career and starting a coaching business.

I did it because I was seeking greater freedom, opportunity, and the chance to do more meaningful work.

All these reasons are still relevant today.

But the one that still stands out is the enjoyment I experience from increasing my autonomy (or at least, my perceived sense of autonomy). 😉

It makes sense, of course: no one likes working for a micromanaging boss, or being stuck in circumstances (like traffic, layoffs, nominal raises) that are entirely out of our control.

And yet, one of the great ironies of my own self-employment is that, for so long, I barely took time off.

At the moment when you can theoretically do anything, you choose to …keep working!

And it’s like that for so many of us.

Americans are, in particular, notoriously horrible at unshackling ourselves from our workaholism.

It’s become fashionable to dis hustle culture, but there’s also a dangerous notion floating around that we’re entitled to things we haven’t worked for.

These two ideas represent extreme ends of the entrepreneur spectrum which I believe sets us up for disappointment and failure.

Hustling non-stop isn’t sustainable for most of us. And neither is having your head in the clouds, believing that a magical unicorn will grant you a beautiful business that fulfills your grandest desires.

I was stuck on the hustle side of the spectrum when I started my business.

I went almost a full year without taking a complete weekend off.

The idea of not working for a week seemed literally impossible.

And a month? Well, that felt impossible.

But back in 2019, I had planned a month-long trip to Africa and honestly, I wasn’t sure at the time – between the vast time difference, travel schedule, and wifi/cellular vagaries – how reachable I’d even be.

Volunteering at the Mungere School in Tanzania, Africa

Volunteering at the Mungere School in Tanzania, Africa

The trip became a forcing function to look at my business model and maybe even reset my parasympathetic nervous system a bit.

It wasn’t easy – I gave up revenue (I had several ongoing retainer clients at the time, and I waived the fees for that month).

But I made it work, and it became a kind of north star for what was possible.

(It’s not just for the self-employed: even if you work for an organization where taking a month off isn’t possible, working virtually may well be. A lot more is possible than we think.)

I got inspired again last year when my wife planned a yoga retreat in Croatia.

I used this as another reason to set boundaries and reinforce my core values of adventure, autonomy, and freedom.

I took most of September off to attend the retreat and island hop through the Adriatic Sea.

Looking down at Hvar town from the Hvar Fortica

A few years ago I was working with a client (and now friend), Teresa Torres, to design her business for ‘lifestyle alignment.’

She re-imagined her business to unplug twice per year for a total of 12 weeks. Every single year she takes off 6 weeks in the summer and 6 weeks during the holidays and into the New Year. It’s now a systematized part of her business!

Taking extended breaks doesn’t have to be a rarity, or something we’re finally entitled to at retirement.

It can be …normal.

Even if you don’t want to take a month off, I’ll be honest: taking Friday off every now and then can be enormously rewarding.

There’s business ROI – better ideas, a clearer perspective – and the personal ROI of recognizing that our lives should be more than just rushing from one meeting to the next.

If you had more white space in your calendar, what would you focus on?

A new year’s resolution I hear a lot is a desire to focus – in a smart, strategic way – on how to grow your business.

There are so many fun things we want to do – new paths we could explore.

But we have to get the scheduling barrier out of the way first, and find the white space.

How can we set up smart systems that can unlock more time for us, and give us more autonomy and freedom?

I’ll admit, taking a month off from client work felt impossible …until I did it.

Now I know it’s an option and I’ll be doing it again this year when I head to Greece.

Here’s a challenge I issue to many of my overworked clients:

  • Choose a week in the future – no more than 6 months away.
  • Schedule something fun that gets you out of your normal surroundings.
  • Block the time and book the reservations.
  • You’ll be unreachable during this time.
  • Plan your business accordingly to make it happen.

This simple exercise generates more fear and action than almost any other. And yet, it always lights a fire and creates a healthy friction that produces results.

I invite you to try it and let me know how it goes.

Whether your goal is to take a month off this year, or just a few more weekends, it’s worth exploring ways to make it happen – and I’m cheering you on.

Live bravely,

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