Testing The "Impossible": 17 Questions That Changed My Life (#206)

The following is a sample chapter from my new book, Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers. Any page numbers are from the print edition.

Audio version is first, then the full text is below that.

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

Reality is largely negotiable.

If you stress-test the boundaries and experiment with the “impossibles,” you’ll quickly discover that most limitations are a fragile collection of socially reinforced rules you can choose to break at any time.

What follows are 17 questions that have dramatically changed my life. Each one is time-stamped, as they entered the picture at precise moments.

#1 — What if I did the opposite for 48 hours?

In 2000, I was selling mass data storage to CEOs and CTOs in my first job out of college. When I wasn’t driving my mom’s hand-me-down minivan to and from the office in San Jose, California, I was cold calling and cold emailing. “Smiling and dialing” was brutal. For the first few months, I flailed and failed (it didn’t help that my desk was wedged in a fire exit). Then, one day, I realized something: All of the sales guys made their sales calls between 9 a.m. and 5 p.m. Obvious, right? But that’s part one. Part two: I realized that all of the gatekeepers who kept me from the decision makers—CEOs and CTOs—also worked from 9 to 5. What if I did the opposite of all the other sales guys, just for 48 hours? I decided to take a Thursday and Friday and make sales calls only from 7 to 8:30 a.m. and 6 to 7:30 p.m. For the rest of the day, I focused on cold emails. It worked like gangbusters. The big boss often picked up the phone directly, and I began doing more experiments with “What if I did the opposite?”: What if I only asked questions instead of pitching? What if I studied technical material, so I sounded like an engineer instead of a sales guy? What if I ended my emails with “I totally understand if you’re too busy to reply, and thank you for reading this far,” instead of the usual “I look forward to your reply and speaking soon” presumptive BS? The experiments paid off. My last quarter in that job, I outsold the entire L.A. office of our biggest competitor, EMC.

#2 — What do I spend a silly amount of money on? How might I scratch my own itch?

In late 2000 and early 2001, I saw the writing on the wall: The startup I worked for was going to implode. Rounds of layoffs started and weren’t going to end. I wasn’t sure what to do, but I’d been bitten by the startup bug and intoxicated by Silicon Valley. To explore business opportunities, I didn’t do in-depth market research. I started with my credit card statement and asked myself, “What do I spend a silly amount of money on?” Where did I spend a disproportionate amount of my income? Where was I price insensitive? The answer was sports supplements. At the time, I was making less than $40K a year and spending $500 or more per month on supplements. It was insane, but dozens of my male friends were equally overboard. I already knew which ads got me to buy, which stores and websites I used to purchase goods, which bulletin boards I frequented, and all the rest. Could I create a product that would scratch my own itch? What was I currently cobbling together (I had enough science background to be dangerous) that I couldn’t conveniently find at retail? The result was a cognitive enhancer called BrainQUICKEN. Before everyone got fired, I begged my coworkers to each prepay for a bottle, which gave me enough money to hire chemists, a regulatory consultant, and do a tiny manufacturing run. I was off to the races.

#3 — What would I do/have/be if I had $10 million? What’s my real TMI?

In 2004, I was doing better than ever financially, and BrainQUICKEN was distributed in perhaps a dozen countries. The problem? I was running on caffeine, working 15-hour days, and constantly on the verge of meltdown. My girlfriend, who I expected to marry, left me due to the workaholism. Over the next 6 months of treading water and feeling trapped, I realized I had to restructure the business or shut it down—it was literally killing me. This is when I began journaling on a few questions, including “What would I want to do, have, and be if I had $10 million in the bank?” and “What’s my real target monthly income (TMI)?” For the latter, in other words: How much does my dream life—the stuff I’m deferring for “retirement”—really cost if I pay on a monthly basis? (See fourhourworkweek.com/tmi) After running the numbers, most of my fantasies were far more affordable than I’d expected. Perhaps I didn’t need to keep grinding and building? Perhaps I needed more time and mobility, not more income? This made me think that maybe, just maybe, I could afford to be happy and not just “successful.” I decided to take a long overseas trip.

#4 — What are the worst things that could happen? Could I get back here?

These questions, also from 2004, are perhaps the most important of all, so they get their own chapter. (See “fear-setting” on page 463 in Tools of Titans.)

#5 — If I could only work 2 hours per week on my business, what would I do?

After removing anxieties about the trip with fear-setting, the next practical step was removing myself as the bottleneck in my business. Alas, “how can I not be a bottleneck in my own business?” isn’t a good question. After reading The E-Myth Revisited by Michael Gerber and The 80/20 Principle by Richard Koch, I decided that extreme questions were the forcing function I needed. The question I found most helpful was, “If I could only work 2 hours per week on my business, what would I do?” Honestly speaking, it was more like, “Yes, I know it’s impossible, but if you had a gun to your head or contracted some horrible disease, and you had to limit work to 2 hours per week, what would you do to keep things afloat?” The 80/20 principle, also known as Pareto’s law, is the primary tool in this case. It dictates that 80% (or more) of your desired outcomes are the result of 20% (or less) of your activities and inputs. Here are two related questions I personally used: “What 20% of customers/products/regions are producing 80% of the profit? What factors or shared characteristics might account for this?” Many such questions later, I began making changes: “firing” my highest-maintenance customers; putting more than 90% of my retail customers on autopilot with simple terms and standardized order processes; and deepening relationships (and increasing order sizes) with my 3 to 5 highest-profit, lowest-headache customers. That all led to . . .

#6 — What if I let them make decisions up to $100? $500? $1,000?

This question allowed me to take my customer service workload from 40 to 60 hours per week to less than 2 hours per week. Until mid-2004, I was the sole decision maker. For instance, if a professional athlete overseas needed our product overnighted with special customs forms, I would get an email or phone call from one of my fulfillment centers: “How should we handle this? What would you like to charge?” These unusual “edge cases” might seem like rare exceptions, but they were a daily occurrence. Dozens per week hit me, on top of everything else. The fix: I sent an email to all of my direct reports along the lines of “From this point forward, please don’t contact for me with questions about A, B, or C. I trust you. If it involves less than $100, please make the decision yourself and take a note (the situation, how you handled it, what it cost) in one document, so we can review and adjust each week. Just focus on making our customers happy.” I expected the worst, and guess what? Everything worked, minus a few expected hiccups here and there. I later increased the threshold to $500, then $1,000, and the “reviews” of decisions went from weekly, to monthly, to quarterly, to—once people were polished—effectively never. This experience underscored two things for me: 1) To get huge, good things done, you need to be okay with letting the small, bad things happen. 2) People’s IQs seem to double as soon as you give them responsibility and indicate that you trust them.

#7 — What’s the least crowded channel?

Fast-forward to December 26, 2006. I’ve finished writing The 4-Hour Workweek, and I sit down after a lovely Christmas to think about the upcoming April launch. What to do? I had no idea, so I tracked down roughly a dozen best-selling authors. I asked each questions like, “What were the biggest wastes of time and money for your last book launch? What would you never do again? What would you do more of? If you had to choose one place to focus $10,000, where would you focus?”

I heard one word repeatedly: blogs. They were apparently both very powerful and under-appreciated. My first question was, “What the hell is a blog?” My next questions were “How are people currently trying to reach bloggers?” and “What’s the least crowded channel?” The people pitching bloggers were generally using email first and phone second. Even though those were my strengths, I decided to experiment with in-person meetings at conferences. Why? Because I felt my odds would be better as one out of five people in a lounge, rather than one email out of 500 emails in an overflowing inbox. I packed my bags and headed to Las Vegas for the Consumer Electronics Show in January, which had more than 150,000 attendees in 2005. It’s like the Super Bowl of technology releases, where all the geeks get to play with new toys. I never even walked in the front door. I parked myself at the offsite Seagate-sponsored BlogHaus lounge, where bloggers were invited to relax, recharge their laptops, and drink free booze. I sipped alcohol, asked a lot of dumb questions, and never overtly pitched. I only mentioned the book if someone asked me why I was there (answer: “I just finished my first book, and I’m really nervous about the launch. I’m here to learn more about blogs and technology”). Famous tech blogger Robert Scoble later described my intricate marketing plan as “get drunk with bloggers.” It worked surprisingly well.

#8 — What if I couldn’t pitch my product directly?

During the 2007 book launch, I quickly found that most media rightly don’t give a rat’s ass about book launches. They care about stories, not announcements, so I asked myself, “What if I couldn’t pitch my product directly? What if I had to sell around the product?” Well, I could showcase people from the book who’ve completely redesigned their lives (human interest); I could write about unrelated crazy experiments, but drive people to my book-focused website (Google “Geek to Freak” to see the result. It was my first-ever viral blog post); I could popularize a new term and aim for pop culture (see “lifestyle design” on page 278 in Tools of Titans); I could go meta and make the launch itself a news item (I also did this with my video “book trailer” for The 4-Hour Body, as well as the BitTorrent partnership for The 4-Hour Chef). People don’t like being sold products, but we all like being told stories. Work on the latter.

#9 — What if I created my own real-world MBA?

This kicked off in 2007 to 2008. See page 250 in Tools of Titans for full details.

#10 — Do I need to make it back the way I lost it?

In 2008, I owned a home in San Jose, California, and its value cratered. More accurately, the bank owned the home and I had an ill-conceived adjustable-rate mortgage. On top of that, I was on the cusp of moving to San Francisco. To sell would have meant a $150,000 loss. Ultimately, I picked up and moved to San Francisco, regardless, leaving my San Jose home empty.

For months, friends pressured me to rent it, emphasizing how I was flushing money down the toilet otherwise. I eventually buckled and followed their advice. Even with a property management company, regular headaches and paperwork ensued. Regret followed. One introspective night, I had some wine and asked myself: “Do I really need to make money back the same way I’m losing it?” If you lose $1,000 at the blackjack table, should you try and recoup it there? Probably not. If I’m “losing” money via the mortgage payments on an empty house, do I really need to cover it by renting the house itself? No, I decided. I could much more easily create income elsewhere (e.g., speaking gigs, consulting, etc.) to put me in the black. Humans are very vulnerable to a cognitive bias called “anchoring,” whether in real estate, stocks, or otherwise. I am no exception. I made a study of this (a lot of good investors like Think Twice by Michael Mauboussin), and shortly thereafter sold my San Jose house at a large loss. Once my attention and mind space was freed up, I quickly made it back elsewhere.

#11 — What if I could only subtract to solve problems?

From 2008 to 2009, I began to ask myself, “What if I could only subtract to solve problems?” when advising startups. Instead of answering, “What should we do?” I tried first to hone in on answering, “What should we simplify?” For instance, I always wanted to tighten the conversion fishing net (the percentage of visitors who sign up or buy) before driving a ton of traffic to one of my portfolio companies. One of the first dozen startups I worked with was named Gyminee. It was rebranded Daily Burn, and at the time, they didn’t have enough manpower to do a complete redesign of the site. Adding new elements would’ve been time-consuming, but removing them wasn’t. As a test, we eliminated roughly 70% of the “above the fold” clickable elements on their homepage, focusing on the single most valuable click. Conversions immediately improved 21.1%. That quick-and-dirty test informed later decisions for much more expensive development. The founders, Andy Smith and Stephen Blankenship, made a lot of great decisions, and the company was acquired by IAC in 2010. I’ve since applied this “What if I could only subtract . . . ?” to my life in many areas, and I sometimes rephrase it as “What should I put on my not-to-do list?”

#12 — What might I put in place to allow me to go off the grid for 4 to 8 weeks, with no phone or email?

Though wordy, I have asked variations of this question many times since 2004. It used to end with, “. . . allow me to go on vacation for 4 to 8 weeks,” but that’s no longer enough. Given the spread of broadband, it’s extremely easy to take a “vacation” to Brazil or Japan and still work nonstop on your business via laptop. This kind of subtle self-deception is a time bomb.

For the last 5 years, I’ve asked myself, in effect, “What can I put in place so that I can go completely off the grid for 4 to 8 weeks?” To entrepreneurs who are feeling burned out, this is also the question I pose most often. Two weeks isn’t enough, as you can let fires erupt and then attempt to repair things when you return. Four to eight weeks (or more) doesn’t allow you to be a firefighter. It forces you to put systems and policies in place, ditch ad-hoc email-based triage, empower other people with rules and tools, separate the critical few from the trivial many, and otherwise create a machine that doesn’t require you behind the driver’s wheel 24/7.

Here’s the most important point: The systems far outlive the vacation, and when you come home, you’ll realize that you’ve taken your business (and life) to the next level. This is only possible if you work on your business instead of in your business, as Michael Gerber might say.

#13 — Am I hunting antelope or field mice?

I lifted this question around 2012 from former speaker of the U.S. House of Representatives, Newt Gingrich. I read about it in Buck Up, Suck Up . . . and Come Back When You Foul Up: 12 Winning Secrets from the War Room, written by James Carville and Paul Begala, the political strategists behind Bill Clinton’s presidential campaign “war room.” Here’s the excerpt that stuck with me:

Newt Gingrich is one of the most successful political leaders of our time. Yes, we disagreed with virtually everything he did, but this is a book about strategy, not ideology. And we’ve got to give Newt his due. His strategic ability—his relentless focus on capturing the House of Representatives for the Republicans—led to one of the biggest political landslides in American history.

Now that he’s in the private sector, Newt uses a brilliant illustration to explain the need to focus on the big things and let the little stuff slide: the analogy of the field mice and the antelope. A lion is fully capable of capturing, killing, and eating a field mouse. But it turns out that the energy required to do so exceeds the caloric content of the mouse itself. So a lion that spent its day hunting and eating field mice would slowly starve to death. A lion can’t live on field mice. A lion needs antelope. Antelope are big animals. They take more speed and strength to capture and kill, and once killed, they provide a feast for the lion and her pride. A lion can live a long and happy life on a diet of antelope. The distinction is important. Are you spending all your time and exhausting all your energy catching field mice? In the short term it might give you a nice, rewarding feeling. But in the long run you’re going to die. So ask yourself at the end of the day, “Did I spend today chasing mice or hunting antelope?”

Another way I often approach this is to look at my to-do list and ask: “Which one of these, if done, would render all the rest either easier or completely irrelevant?”

#14 — Could it be that everything is fine and complete as is?

Since starting deep work with “plant medicines” in 2013 (see James Fadiman, page 100), I’ve doubled and tripled down on cultivating more daily appreciation and present-state awareness. The above is one of the questions I ask myself. It’s accompanied by complementary tools and rituals like the 5-Minute Journal (page 146), the Jar of Awesome (page 570), and thinking of “daily wins” before bed à la Peter Diamandis (page 373). To reiterate what I’ve said elsewhere in this book, type-A personalities have goal pursuit as default hardwiring. This is excellent for producing achievement, but also anxiety, as you’re constantly future-focused. I’ve personally decided that achievement is no more than a passing grade in life. It’s a C+ that gets you limping along to the next grade. For anything more, and certainly for anything approaching happiness, you have to want what you already have.

#15 — What would this look like if it were easy?

This question and the next both came about in 2015. These days, more than any other question, I’m asking “What would this look like if it were easy?” If I feel stressed, stretched thin, or overwhelmed, it’s usually because I’m overcomplicating something or failing to take the simple/easy path because I feel I should be trying “harder” (old habits die hard).

#16 — How can I throw money at this problem? How can I “waste” money to improve the quality of my life?

This is somewhat self-explanatory. Dan Sullivan is the founder and president of a company called Strategic Coach that has saved the sanity of many serial entrepreneurs I know. One of Dan’s sayings is: “If you’ve got enough money to solve the problem, you don’t have the problem.” In the beginning of your career, you spend time to earn money. Once you hit your stride in any capacity, you should spend money to earn time, as the latter is nonrenewable. It can be hard to make and maintain this gear shift, so the above question is in my regular journaling rotation.

#17 — No hurry, no pause.

This isn’t a question—it’s a fundamental reset. “No hurry, no pause” was introduced to me by Jenny Sauer-Klein (jennysauerklein.com), who, along with Jason Nemer (page 46), co-created AcroYoga. The expression is one of the “9 Principles of Harmony” from Breema, a form of bodywork she studied for many years. I routinely write “No hurry, no pause” at the top of my notebooks as a daily reminder. In effect, it’s shorthand for Derek Sivers’s story of the 45-minute versus 43-minute bike ride (page 190)—you don’t need to go through life huffing and puffing, straining and red-faced. You can get 95% of the results you want by calmly putting one foot in front of the other. One former Navy SEAL friend recently texted me a principle used in their training: “Slow is smooth. Smooth is fast.”

Perhaps I’m just getting old, but my definition of luxury has changed over time. Now, it’s not about owning a lot of stuff. Luxury, to me, is feeling unrushed. No hurry, no pause.

***

So, kids, those are my questions. May you find and create many of your own.

Be sure to look for simple solutions.

If the answer isn’t simple, it’s probably not the right answer.

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Tools of Titans is available at Barnes & Noble, Amazon, Books-A-Million, iBooks, Indiebound, Indigo, and more. If you enjoyed the above, I guarantee you’ll enjoy the whole thing. Thanks for reading!

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