Chaos and doubt

Plan Your Next: Letter No. 6

Good morning!

I definitely have my moments of doubt. In fact, my life is filled with them. This was one of those weeks as you’ll soon find out. But, while this email might be shorter—hooray?!—it’s more important to me to find balance in the routine of writing.

Normally, I would never let this see the light of day, but I think it’s better to practice to find ways to talk through it.

So stick with me this week, and know that we all go through some shit that might seem trivial in the big picture. But if you can focus in on the problem and ask questions about what got you there, and how you might get out, the light at the end of the tunnel is waiting.


“The only thing I know is that I know nothing.” — Socrates (supposedly)

Right in the middle of the week, in a moment of weakness, and physically weak in general, I started to let those baby tears fly. It had been building. Busy weeks, busy work, busy everything just came to a tilt.

My eyes don’t sweat often, because honestly, I do my best keeping them at bay. My wife said it had been a year. That was our wedding, so it obviously doesn’t count. And the next time? I can’t remember.

It felt good though, and as I’m sitting in an airport right now waiting to board a red-eye flight, I find myself wishing I did that more often.

The crux of the problem was that for a moment, I had lost confidence in myself. There are moments where I think I bring value, but there are moments where it all goes to shit and I don’t know how to bring more. Sometimes it comes naturally, and other times it’s forced.

It doesn’t mean that it’s not a valid feeling, but it does mean that I should stop and think about what caused that and to ask if I’m looking at it irrationally.

But as I sit here, listening to bad dance music from the empty airport bar, a lot of this came about from insecurity. It comes and goes, and thankfully I don’t suffer from depression, but that imposter syndrome is real, like it or not.

We’re usually traversing the line between order and chaos—the yin and yang—navigating it carefully and hoping to stay grounded in the routines we have set.

Chaos ensues when the order we have set starts to break down, shattering our confidence, and pushing us into the depths of the unknown.

What is familiar, however, is that chaos and order are fundamental to our lived experiences. We have control over some things, and not others. There aren’t exceptions to this reality.

We can’t afford to always look for stability, since order without chaos is also ignoring the balance of life. When we’re looking forward or thinking about what’s next, we’re naturally inviting chaos into the mix.

How I start to find order

  • Acknowledge what is causing this feeling of despair. Talk about this with someone. Talk about the pain out loud.

  • Ask questions about what put you here, and what steps you can do to put life back in order.

  • I usually try and meditate, or at the very least, sit with my own thoughts for a bit and try to look at the problem from a different angle.

Reading this week

  • The Rational Optimist - I am definitely an optimist; maybe too much of one (i.e. Hey wife! Let’s move and figure out the rest later!). But with all of the political craziness and lack of hubris from many of our leaders, if you look back throughout history at a macro level, the world feels like it’s trending in the right direction. This book tries to put that in perspective, and tackles a lot of questions in regards to how we built civilizations by trusting each other through trade and reliance on skills outside of our own. It’s a simplistic synopsis, but it’s been great so far.

  • 12 Rules for Life: An Antidote to Chaos - I just started reading this, but the timing couldn’t have come at a better time. It’s so bizarre that when I’m thinking about a problem, I tend to find insight in the very exact thing I’m reading, usually because I’m desperately looking for an answer. So far so good.

Favorite internet bits

The Stoic Emperor@TheStoicEmperor

Reading is not a chore.

Reading is theft. It is a robbery.

Someone smarter than you has spent 20 years beating their head against the wall trying to solve the problem you're dealing with.

You can steal that hard won knowledge and make it yours.

That is power.

February 24, 2018

My question for you

How do you handle chaotic moments to regain order?

In case you’re wondering, even though the start of the week was tense, getting through the chaos was certainly worth it. I’ve done a complete 180. If you’re feeling stuck or need a creative nudge, I opened up a couple of spots to chat.

Have a great week!


This is Plan Your Next. It’s a conversation about being ready for what’s next. Well, because there is always a next. I’m Nate, designer and conductor of this group.

If you have something to share or add, please hit reply and expect a response!