Testing The Impossible: 17 Questions That Changed My Life

The Tim Ferriss Show with Tim Ferriss. First Aired 12/7/2016, (rebroadcast) run time: 51:57

“Whenever you find yourself on the side of the majority, it is time to pause and reflect.” – Mark Twain

Tim Ferriss shares extremely valuable bombs of awesomeness in his latest best-seller, Tools of Titans.

He shares the 17 questions that changed his approach on how he handles life and business.


Question #1: What If I Did The Opposite For 48 Hours?

In the early part of his career, he was doing the same as the other sales reps of his company – cold calling leads between 9 – 5.

It didn’t take long for this process to get boring and unrewarding, so he started making his calls outside of work hours on just Thursday and Friday.

He also asked questions instead of pitching offers.

The result? He often got past the gatekeepers (receptionists) who were off when the clock struck 5 and got in touch with his target leads much faster, and closed more sales than his colleagues.

Question #2: What Do I Spend A Silly Amount Of Money On? How Might I Scratch My Own Itch?

To help with ideas for a business, he looked at what he was spending a lot of money on.

In his example, he found that he was spending a lot of money on brain supplements.

So instead of paying for his supplements, he created his own company, Brain Quicken, as he knew the market well and was a consumer himself.

Question #3: What Would I Do or Be If I Had $10M? What’s My Real Target Monthly Income?

This helps to find clarity in what exactly you need to be doing:

How much do you need to sell, what price points, how many leads do you need every month, and what work needs to be on the priority list.

I’m a huge fan of working backward from a goal and it’s the reason why it can sometimes take me days/weeks/months to start executing a plan – because I’m spending careful time in planning.

Question #4: What Are The Worst Things That Can Happen? Can I Get Back Here?

Fear is everyone’s worst enemy because it’s not circumstances or surroundings that stop us, it’s ourselves.

Fear is debilitating – it’ll stop you in your tracks and all the ideas you have in your head can end up leading to nowhere.

The exercise of creating the worst possible scenario then figuring out the likelihood of it happening (as well as the likelihood of being able to bounce back from it) makes that fear a lot less daunting.

Question #5: If I Can Only Work 2 Hours A Week On My Business, What Would I Do?

This question forces you to analytically find the most important tasks in your business and what tasks you should be delegating to your team.

Sometimes I find myself working on things that don’t serve my company well, tasks that are performed better by others but still fall into my lap for sake of speed.

However, time and time again I’m kicking myself because I’ll spend so much time on the task to produce mediocre work when one of my teammates could’ve handled it so much faster and produced a higher quality result than I ever could have.

Why do we do this to ourselves!?

Question #6: What If I Let Them Make Decisions? ($100, $500, etc.)

“To make huge, good things, you need to be okay with letting the small, bad things happen.”

Trust is a major factor in the growth of any business.

As the boss, founder, CEO, or owner, you must learn to let go.

Trust the people you put in place to get a job done and your people might just surprise you.

The example Tim Ferriss shares is from the early stages of his company, Brain Quicken.

His team was constantly asking him for guidance on decisions that required an abnormal expense to the point it became too much.

So he empowered them all to make decisions that cost less than $100 with the goal of “making the customer happy”.

As you might expect, the results were great.

Customers were happy, teammates thrived, and the business grew.

Question #7: What’s The Least Crowded Channel?

There’s the saying, “don’t try and reinvent the wheel”.

I love that saying as I believe it’s the fastest way to become successful in business without failing time and again by trying innovative methods.

However, there’s also the saying, “there’s more than one way to skin a cat”.

So of all the methods to become successful and of all the business models that work, which one offers the least amount of competition while also delivering lucrative results?

Question #8: What If I Couldn’t Pitch My Product Directly?

Another question that begs you to think creatively about making sales.

Most people don’t like being pitched (unless you’re a weirdo like me), an alternate strategy is to tell stories which indirectly lead to sales.

Example: when promoting The 4-Four Body, Tim Ferriss used a blog article to drive traffic to his site and indirectly lead people to buy his book.

Question #9: What If I Created My Own, Real World MBA?

This topic is elaborated on in detail on page 250 of his book, Tools of Titans, but is built on the idea from Scott Adams (creator of Dilbert) which focuses on systems rather than goals.

If you plan on the development of skills and relationships rather than short-term projects, then you end with valuable intangibles even if the short-term project fails.

Question #10: Do I Need To Make It Back The Way I Lost It?

Let’s use the money to elaborate on this question.

If you lost, $50,000 in a real estate investment, does this mean you have to immediately make up that money through another real estate investment?

Would that be the smartest move given that you just lost in that field?

Or can you reinvest and make that money back through another means, perhaps through a business investment?

A stronger analogy is that of a gambler – if you lose $10,000 while playing blackjack should you still continue playing to make that money back?

Humans have a common tendency to rely too heavily on the first piece of information given (anchoring) and sometimes this tendency can prevent us from seeing opportunity elsewhere.

Question #11: What If I Could Subtract To Solve Problems?

Addition by subtraction comes to mind here because we’re typically wired to solve problems by adding.

Alternatively, we should avoid the question “What can I change?” to “What can I simplify?”

A marketing principle that encourages action is limiting choices for our customer.

Grocery stores often have so many brands, shapes, and sizes of the ketchup while Costco only sells one – extra large Heinz.

That’s because Costco understands that too many choices can cause paralysis among its customers and instead focuses on making the buying decision simple as either Yes or No to the big bottle of Heinz ketchup.

Question #12: What Might I Put In Place To Allow Me To Go Off The Grid For 4-8 Weeks Without Phone Or Email?

This forces you to simplify and systematize business.

If you need to be completely off the grid, meaning that you can’t be called upon to fight the fires at work, you’ll need to put some preventative measures in place and more importantly the counteractive procedures to ensure business keeps going.

Empower the right people to take command, have some guidelines for your team to continue moving forward in case of unexpected occurrences and reward yourself with mini-retirements.

The result will be a business that continues to move forward without needing you to sit behind the driver seat.

Question #13: Am I Hunting Antelope Or Field Mice?

A lion has enough speed and agility to hunt field mice, obviously.

The amount of energy expelled versus the tiny amount of energy consumed, however, would mean that a lion would eventually starve to death if it only ever hunted mice.

Hunting antelope, on the other hand, allows the lion to feed not just itself, but the rest of the pride for days.

Remember: there’s many fish in the sea but significantly fewer whales in the ocean.

Not all customers are created equal and while it does require more work to land the giant whales, the benefits of one big haul outweigh the work that comes with securing the small fries.

Question #14: Could It Be That Everything Is Fine And Complete As Is?

Sometimes we look to make improvements that aren’t there or aren’t even necessary.

Good is usually good enough.

Question #15: What Would This Look Like If This Was Easy?

This question is partnered with the next question, as the easiest solution typically involves the help of others which also typically involves money.

Question #16: How Can I Throw Money At This Problem? How Can I “Waste” Money To Improve My Quality Of Life?

Dan Sullivan says, “If you’ve got enough money to solve the problem, you don’t have a problem”.

Instead of stressing out on figuring out and creating a solution on your own, throwing money at the problem is the easiest and quickest solution ALL the time.

An extreme example:

How can you get from San Diego, CA to New York City if you needed to get there in a day?

Let’s simplify this by giving ourselves just 3 options: walk, drive: or fly.

At first glance, the obvious answer is to fly because by foot is impossible (unless you’re the Flash) and driving will take too long.

So of course, spending money on a much more expensive plane ticket is the best answer.

But let’s use a business goal as a new example:

How can you gain more leads to your business through online marketing methods?

Let’s simply this by giving ourselves 3 options: you can learn the methods on your own, send a current employee through a training course, or hire an already capable agency to do this for you.

It’s not so simple anymore as it depends on the business owner.

All have their positives and negatives but to the cash-strapped small business, they’ll likely opt for option a or b while the bigger dogs will opt for option c.

At the beginning of your career, you’ll spend the time to make money.

Once you start hitting your stride though and you start to make more money, you’ll need to start spending money to earn more time, as the latter is non-renewable.


Question #17: “No Hurry, No Pause” – Jenny Sauer-Klein

This isn’t a question but more of a mantra that was adopted from the “9 Principles Of Harmony” from Breema.

“When you rush, time shrinks. When you’re relaxed, time expands. This is true even though it’s very hard for the mind to get. When you’re relaxed and doing something willingly, you’re participating in life.” – Jon Schreiber

A struggle for most entrepreneurs, including myself – we strive to achieve great things and with that typically comes an increased workload.

If you’re an entrepreneur then you know exactly how your To-Do List can get full of tasks and how the fuel on the fire can be so intense that you’re working non-stop for what seems to be like your entire day.

Of course, this pace is hard to maintain, and eventually, we all end up at the stage of burnout.

I liken this to how most people start a new fitness routine or new diet.

They go into it guns blazing, super motivated and excited to get results but 9 out of 10 times will end up right where they started.

A more appropriate method would be to instead make small, incremental lifestyle changes to enjoy a long-term benefit.

Don’t rush excellence, greatness takes time – “Slow is smooth, smooth is fast”.


Who Is Tim Ferriss?

  • Renown life hacker and the man behind “The Tim Ferris Effect”
  • Described as our generation’s self-help guru and one of Fast Company’s “Most Innovative Business People of 2007”
  • Author of The 4-Hour Workweek and The 4-Hour Body (2 out of the 10 Most Highlighted books on Amazon)
  • Also wrote The 4-Hour Chef, and now, his latest and most anticipated creation, Tools of Titans

Jay Magpantay Administrator
Author, Entrepreneur, & Good-Vibes Distributor
Easygoin’ bhiz-nerd who’s got a thing for sci-fi & tacos — Join my free workshop to find out how I grew my business by writing a single book.
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