This article is an excerpt from the Shortform book guide to "Tools of Titans" by Timothy Ferriss. Shortform has the world's best summaries and analyses of books you should be reading.
Like this article? Sign up for a free trial here .
Do you have a question that you ask yourself every day? How can having a set of questions to ask yourself help spur your life in the desired direction?
If you want to build a better life, become more successful, and upgrade your lifestyle, you must constantly challenge your mind, thinking of ways to level up and spot opportunities. To this end, entrepreneur and lifestyle guru Tim Ferriss has a set of 17 questions he regularly asks himself.
Without further ado, here are Tim Ferriss’s questions to ask yourself.
Questions That Will Change Your Life
In his book Tools of Titans, Tim Ferriss stresses the importance of challenging your mind by asking yourself hard questions. He shares 17 of the questions he asks himself to further his goals. Try some of Tim Ferriss’s questions for yourself.
1. What if I do the opposite of what I normally do, for 48 hours?
If you’re stuck and not getting the performance you want, maybe you need to invert what you’re doing. If you try the opposite for just 48 hours, the damage is limited—at worst, you fail and go back to your normal routine. At best, you find a totally new successful way to do things.
As a salesman for a tech product early in his career, Tim wasn’t meeting his sales numbers. At a loss for what to do, he looked at what the other salespeople were doing, and decided to do the opposite. Other people worked 9 to 5; Tim decided to call outside of 9 to 5. He found that he was able to reach executives, who were still working outside normal business hours, and bypass their assistants, who were not.
2. For business ideas: what do I personally spend a lot of money on?
This is a perfect question if you want to start a business but you don’t know what problem to solve. Chances are, you’ve been solving that problem for yourself.
When the dotcom crash happened, Tim Ferriss wanted to start his own company. Instead of doing deep market research, he looked at his credit card statements – he was spending $500 per month on sports supplements on an annual income of $40k. This validated a personal need that he could turn into a business. Even better, as an avid consumer, he knew how the industry worked – which ads worked best, which vendors had the highest reputation. He created a supplement he couldn’t find on the market called BrainQUICKEN, launched a business, and paved the way to the 4-Hour Workweek and beyond.
3. If I had $10 million, what would I be doing differently? Do I really need $10 million to get this lifestyle today?
Are you enduring a crushing career, hoping to one day escape into the nirvana of retirement? Life is short—try to design the life you want today, rather than put it off 20-40 years into the future (when, heaven forbid, a tragic accident or illness might cut it short). Your ideal life might be deceptively easy to achieve.
While building BrainQUICKEN, Tim Ferriss was stretched to his energy limit and felt trapped in his caffeinated, overworked mental state. He stopped and asked himself what kind of lifestyle he really wanted.
After quick calculations, Tim realized his target lifestyle cost far less than he anticipated. The resource he lacked was time and flexibility, not cash. This motivated him to start redesigning his life immediately, before he even had $10 million.
4. What’s the worst that could happen? If it did happen, could I recover?
Anxiety has its roots in the uncertain. You don’t get anxious about turning on your faucet, because you know what’s going to happen. But you get anxious about asking someone on a date, or quitting your job to start a business, because you don’t know what’s going to happen.
This question pushes you to make your fear concrete. By defining your demons, they become easier to fight.
When Tim Ferriss was stressed about BrainQUICKEN, he dreamed of taking a year-long travel sabbatical. The business was running on all cylinders and he was intimately tied to its operations. So his dream remained a dream for 6 months.
Finally, he forced himself to question his assumptions. What was the worst that could possibly happen? Well, his business could grind to a halt and possibly go bankrupt. A quality issue could occur, and he’d get sued. His bank account would plummet, and his belongings would be stolen. Then he might contract malaria on his travels.
So…was that it?
After picturing the worst case scenario, Tim realized it really wasn’t that bad. Even in this worst case, he could recover. Even better, by defining the problems, he could tackle them today. If his business operations would fail in his absence, how could he make them more robust? How could he protect himself from malaria? These problems were easier than he realized.
5. If I capped my working time to 2 hours per week, what would I do?
How do you get the most out of your time? If someone pointed a gun at your head and forced you to work for only 2 hours a week, how could you maximize your chances of not getting fired? Use the 80/20 rule to find the best outputs of your time.
This question is especially good for managers. But even if you’re not a manager, it can also yield insights into your own work.
Tim Ferriss used this question to make his year-long sabbatical from BrainQUICKEN a reality. He focused on the concentrated products and customers that provided the most profits, and fired his highest-maintenance customers. He automated order handling to streamline operations.
6. Delegation: What if I give complete freedom for decisions up to $100? $500?
If you tend to micromanage, you’re limiting your output. You’re clearly proud of your work and you want to limit the number of mistakes, but you’re probably also overestimating the error rate of other people. This dramatically shortens your leverage, since you’re working on low-impact items other people should be taking care of.
When managing BrainQUICKEN, Ferriss spent 40 hours a week on customer service, fighting fires and answering questions. He’d get interrupted with special product requests or customs forms. He felt responsible for making the calls.
So (as per Question 1), he did the opposite—he gave power to his customer service agents. “If it involves less than $100, please make the decision yourself,” he emailed. To combat abuse, he reviewed these scenarios once a week with his staff.
Surprisingly, few catastrophes happened, and he gradually raised the threshold to $500 and then $1,000. Reviews went from weekly to monthly to never. Consequently, he reduced his personal customer service time spend from 40 hours/week to 2 hours/week.
7. What’s an underrated channel for marketing or promotion?
If you’re selling a product or service, this question more literally applies to you. How can you reach people in a way most competitors are ignoring?
When launching his first book, The 4-Hour Workweek, Tim Ferriss asked best-selling authors, “When promoting your book, what absolutely didn’t work? What would you do more of?”
Consistently, he heard about blogging. Without knowing much about blogging, he went to a trade show and hung around bloggers, eavesdropping on conversations and asking questions. This prompted him to start his 4-Hour Workweek blog, which led to his first viral posts.
(Shortform note: Even if you’re not selling a product, you may find ways to create value that go outside standard practice.
For example, if you’re an attorney, your competition is trying to make partner by billing a ton of hours. What if you looked the other direction, and you focused on getting new clients in?
If you’re trying to create a new Youtube channel (Youtube being an established, very crowded network), what new, up-and-coming channel could you establish yourself on first?)
8. Marketing: What if I don’t pitch my product directly?
People don’t like announcements or being sold products. They like hearing narratives.
When promoting his book The 4-Hour Workweek, Tim Ferriss couldn’t persuade journalists to introduce his book. But he fashioned engaging stories around concepts in the book. He showcased success stories from the book, people who redesigned their lifestyles. He wrote about his own personal body transformations, like in Geek to Freak. He released The 4-Hour Chef on audiobook for free on BitTorrent. These were stories worth spreading, and by extension his books got more publicity.
9. Education: Instead of a formal degree, what if I made my own degree?
Any graduate program or trained course costs a lot of cash and opportunity cost. Instead of attending the program, could you take all that money and get equivalent or better training?
Early in his career, Tim Ferriss thought an MBA might be useful for developing new skills, developing a better network, or having it look good on his resume.
Eventually he realized he could tie all three goals together in startup investing. Estimating the cost of an MBA at $120k over 2 years, he set aside $120k to make small $10k-20k investments in companies.
Importantly, Tim was prepared to lose it all—much as he would have lost the tuition to business school. This prompted him to actually take action rather than being scared. Even if his investments failed, he saw the experience and the added network as well worth the $120k. By learning from dozens of founders and investors, he created his own investment rules and made a few investments. His investments eventually panned out, making back double what he invested.
———End of Preview———
Like what you just read? Read the rest of the world's best book summary and analysis of Timothy Ferriss's "Tools of Titans" at Shortform .
Here's what you'll find in our full Tools of Titans summary :
- The habits and beliefs of 101 people at the top of their game
- Tim Ferriss' list of 17 questions you should ask yourself to challenge your thinking
- How emulating the habits of successful people you look up to can make you successful as well
