What Captain Hindsight can teach you about living a more productive life

Cody McLain
8 min readFeb 3, 2016

It’s a hot summer day and firefighters are battling the flaming inferno — hoping to save those trapped at the top of the nearly consumed apartment building. Things aren’t looking good — and hope is quickly fading.

But then, when the outcome appears its bleakest in the city of South Park, a hero arrives!

Up in the sky — it’s a bird, it’s a plane. No, it’s Captain Hindsight!

The onlookers cheer as the superhero descends to discuss the situation with the fire chief.

What’s going to happen? Is Captain Hindsight going to fly into the burning building and rescue the trapped? Is he going to give the fire chief a brilliant plan that will end the chaos immediately?


Captain Hindsight begins to explain to the onlookers what should have been done differently.

“You see those windows over there? They should have built a fire escape from there.”

“You see up there on the roof? They should have reinforced it so that a helicopter could land up there.”

After finishing with his seemingly useless advice, Captain Hindsight takes off to go tell someone else what they should have done. And those on the street cheers him on — impressed with the hindsight he provided.

Meanwhile, those of us watching South Park chuckle — realizing how ridiculous it is to have a superhero that explains mistakes rather than solves problems.

Afterall, everyone learns from their mistakes. Right?

What we can learn from Captain Hindsight about productivity

We all have annoying friends (or family) that tell us what we should have done differently:

“I told you that guy was a jerk.”

“Didn’t I say your business idea was going to flop?”

“See, I knew we would run out of gas.”

EVERYONE enjoys being a Captain Hindsight, telling us what we already know — after the fact. And it’s annoying.

But despite how annoying Captain Hindsight is, we can actually learn a lot from him — if we implement a process to prevent the same mistake from happening again (something we often forget to do).

When we realize that we seem to run into the same problem over and over, perhaps it’s time to listen to what Captain Hindsight has to say and actually build that fire escape.

How I stopped forgetting things when I travel

Having started offices in both India and the Philippines, in addition to doing business all across the US, I am a frequent traveler.

When I first began to travel regularly, it seemed like I would forget something on every trip! If it wasn’t my computer charger, it was my phone charger. If it wasn’t my belt, it was my workout shoes. After every trip I would make a mental note of what I forgot, but then on the next trip it would be something else entirely.

It was so frustrating!

So finally, after far too long, I decided to do something about it. I took a few minutes and developed my comprehensive traveler checklist. Using Evernote I developed a list of every single item I needed — both for local and for international travel.

Some of my travel gear

This has allowed me to pack the night before a trip and sleep comfortably, knowing that I have everything prepared for my journey.

And of course, over the years this list develops — as I discover additional items I need (or never use). If another item comes to mind while I’m traveling, I simply add a reminder on todoist to update my my travel checklist once I’m home.

This is one of many personal tasks that I’ve developed processes for. Others include having one place for my keys and wallet, several phone chargers where I need them most (at home, in the car, and at the office), etc.

Anytime I realize that I run into the same problem repeatedly, I try to develop a solution to eliminate or minimize the issue.

Start making $1,000 an hour by finding things to automate and outsource at work

Just as I try to improve my personal productivity through the use of prospective hindsight (also referred to as “pre-mortem”), I enjoy finding ways to maximize my business productivity as well.

The two primary ways to increase business productivity are to automate and outsource. As anyone who’s been following my blog for some time knows, I love using apps to maximize my productivity. Additionally, as the CEO of SupportNinja, I’m always finding new ways to gain value from outsourcing.

What I’ve learned over time is that the greatest productivity vacuum is trying to do everything yourself. Entrepreneurs particularly have a difficult time with this for two reasons:

1. Entrepreneurs like to have control over what’s happening.
2. Entrepreneurs have a hard time paying money for something they can do themselves.

But there are some serious issues with this. First, if you have to be in control of every element of your business, it will never scale beyond just you. Second, when you spend your time on trivial tasks, you are literally losing money.

A great article published in Entrepreneur Magazine discussed how to make $1,000 an hour by knowing when to pay someone else to do a task. As the author discussed, if you mow your lawn for an hour, rather than paying the neighbor’s kid to do it — you’re earning $10/hr for that time.

Rather than mowing your lawn, you could be spending the hour finding another client — a potential $100/hr activity. Or, if you hire a salesperson to do that $100/hr project, you can free yourself up to speak at a convention that brings in $1,000 per hour invested!

Sure, if the alternative is watching TV, you may as well mow the lawn to get some exercise. However, if you’d rather spend that time working on a $1000/hr task, by all means — hire the kid!

Once you start looking at each activity and how much it would cost to automate or outsource, you may discover that much of your day is spent doing $10/hr tasks that hinder your business growth. Find ways to maximize your productivity, and you will be well on your way to turning that “hobby” into a million dollar business.

If it happens 3 times, find a permanent solution

My personal philosophy is “if it happens 3 times, find a permanent solution”. If something becomes an inconvenience once, it’s a fluke. If I’m inconvenienced twice, it’s coincidence. However, once the same thing happens three times, it’s become a routine — and I don’t want to waste my time on unhealthy, stressful routines.

As Daniel Levitin shares in this fantastic TED talk, you’re not at your best when you’re stressed. When annoying things happen that throw off your groove, it can have a negative impact on your entire day, health and success.

Levitin suggests that the solution is to develop a “pre-mortem” plan. If you’ve watched one of the countless CSI shows over the years, you know that a “post-mortem” is the examination of a dead body to determine the cause of death.

Essentially, you are determining the cause of the event after it has happened.

Meanwhile, with a pre-mortem you are seeking to determine the cause of a negative event (hopefully not your death) before it happens — and then taking preemptive steps to prevent it or reduce its negative effects.

While you can’t prepare for every little thing that might happen, you can make intelligent decisions based on past experiences. If you get stuck on the highway once because of an accident, that’s a fluke. However, if you discover that your commute always takes 30 minutes longer during rush hour, maybe you should consider heading to work earlier or finding another route.

By planning ahead for negative outcomes, we can reduce our stress levels and have a more enjoyable life all-around.

The three steps to removing repetitive stress

From my experiences, I’ve come up with a three-step process for removing repetitive stress from my life. If you find yourself overwhelmed by worries, consider following this strategy to help ease the worry.

1. Be mindful of when something bad happens or could happen

One study revealed that, while optimistic people are happier and have less stress overall, when an optimistic person also maintains realistic expectations, they are even more successful.

According to Sophia Chou, the facilitator of the study, realistic optimists are able to plan ahead and prepare for what may happen, while still assuming that the best case scenario will occur. These individuals have a plan A, plan B, and plan C — meaning that they can maintain a positive attitude because, if plan A doesn’t work out, it is very likely that plan B or C will.

When we assume the best, while preparing for the worst, we are able to keep a positive attitude AND succeed.

So, although you want to keep a positive attitude, make sure that you spend time analyzing things that have, or could, go wrong — and prepare for them in the future.

In regards to your daily activities, start taking note of when something negative or annoying happens. Did you spend longer on a project than anticipated? Mark down why and what could have made it run smoother. Did a date flop? Mentally walk through the night and determine where things went bad.

Once you start taking note of when, how, and where negative things happen, you are well on your way to minimizing your stress and increasing your happiness level.

2. Create a plan to prepare for next time

As you start tracking where things go wrong, you will begin observing patterns.

When the same issue comes up time and time again, it’s time to create a strategy to prevent it from being an issue in the future.

Perhaps you need to buy a product, hire a team member, take a course, or develop a mental note of what to do next time.

If you keep getting shafted by tolls or parking meters, go out and buy something like this coin organizer so you’ll always have coins in the car. When you realize that half of your day is spent on technical support, hire a tech specialist to manage those tasks so you can spend your time on sales. If you find yourself struggling to make conversation when meeting new people, memorize a list of conversation topics and plan ahead before going to a party.

As you begin to create solutions for the habitual stresses you face, you’ll see your time free up and your stresses diminish.

3. Apply this mindset to every part of your life

Too many people spend their entire day putting out fires rather than making big wins. By taking 30 minutes to prepare ahead of time you can save yourself hours, days, and weeks in the long-term.

So allot some time every week to solving one big problem in life. What is one annoyance that is perpetually bothering you — and how can you minimize it’s impact on your life?

Create post-mortems and use introspective hindsight to slowly eliminate life’s problems — one at a time.

What issues are you stuck solving over and over again?

Most of us have a plethora of stressors that consume our time on a regular basis. We never stop to determine how we can solve these issues. Instead, we keep putting bandages on an open wound that really needs a few stitches.

Take a moment to think about the last few issues that have made your life more difficult. What could you do right now to prevent these issues from happening in the future? Is there someone you could hire, something you could purchase, or a plan you could develop?

Try developing a plan to eliminate one challenge every week. Then, once you’ve solved it, share the solution with others! Who knows, maybe you’ll become as much of a hero as Captain Hindsight.



Cody McLain

Founder of $12m SupportNinja, Author of From Foster Care to Millionaire book, Host of MindHack.com Podcast