Tim Ferriss’s 17 Questions to Solve Your Life Problems

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Feeling stuck in life? Asking extreme questions gets you thinking about your life from a different direction. You might find the solution was obvious all along.

Tim Ferriss’s 17 questions are a great start to questioning what you can improve about your life. He discusses them in his best-selling book Tools of Titans (here’s my detailed summary of the book). I humbly share Tim Ferriss’s questions below, adding my own interpretations and thinking exercises to help you apply them.

Since many of these questions relate to owning a business, I’ve purposely broadened the 17 questions to address more people, no matter your occupation.

Accompanying each of Tim Ferriss’s 17 questions is a 2 minute exercise prompting you to reflect on each question and type in your answer. In each form there’s an email field, so you’ll get your responses and hold yourself accountable.

Take just 1 hour working through this page – I guarantee you’ll get insights you can apply immediately to your life.


Question 1: What if I did the opposite 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. He didn’t have much to lose, and this inversion might lead to new insights.

For example, he noticed that salespeople made calls from 9AM to 5PM. The problem was that during these hours, the people he was trying to reach – the CTOs and the CEOs – were guarded by their receptionists, and he could never get through. What if he did the opposite of what everyone else did? So he called his sales targets from 7AM-9AM, and from 6PM-8PM. During this time, the executives were working, but their receptionists weren’t. He got through.

He applied this thinking elsewhere in his role. Instead of being a hard-pushing salesman blabbing about his product, what if he just spent his time asking questions and understanding his target’s problems? Eventually, his inversions boosted him to the top performing salesperson in his region.

Question 1 recalls Charlie Munger’s advice of “Invert, always invert.” Don’t take for granted what the standard wisdom is.


2-minute exercise

So take 2 minutes to reflect on this question.



Sometimes you already know what you need to do – this exercise just gives you the courage to do it, by capping your exposure time to 48 hours.

  • What if instead of biting your tongue and taking a back seat at work, you instead openly spoke your mind for 48 hours?
  • What if instead of obsessing about perfecting your side project before showing it publicly, you released it within 48 hours?

In contrast, sometimes you don’t know what exactly you should do, and this exercise shows you options.

  • What if instead of going out with friends every night, you denied every invitation for 2 days and spent it at home?
  • What if instead of compulsively checking your email or Slack, you shut it off for 6 hours a day, for just 2 days?

By forcing yourself to behave differently, you’ll question the benefit of your original behavior. For checking email, maybe it turns out no email is really that urgent, but you love the focused time you get by turning it off.

I habitually invert to catch my blind spots. What am I missing that can go wrong? Why am I defining success in a certain way?


Question 2: What do I spend a lot of money on? How might I scratch my own itch?

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.

Tim’s story corroborates Paul Graham and Y Combinator’s advice of “solve your own problem.” By solving your own problem, you guarantee that at least ONE customer exists for what you want to build. And given the 7 billion people in the world, chances are that thousands of people face your very problem. If you can attract a small group of intensely loyal users (or 1000 true fans), you’re off to a great start.

I would expand Tim’s questions beyond just money:


2-minute exercise

  • What do you spend a lot of TIME doing that you feel is wasteful?
  • What are small frictions in your life you wish didn’t exist?
  • What kind of solution have you hacked together that isn’t commercially available? Could you turn your hacky solution into a product?



Many great companies were founded this way. Before Sara Blakely started Spanx, she was creating her own form-fitting undergarments by cutting pantyhose. When Drew Houston created Dropbox, he went on a 4-hour long bus ride but forgot his USB drive.


Question 3: What would I do if I had $10 million? What’s my real target monthly income?

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 the questions above. “What would I want to do, have, and be if I had $10 million in the bank?” For the lifestyle he wanted, how much in monthly income did he REALLY need?

After quick calculations, Tim realized his target lifestyle cost far less than he anticipated. The resource he lacked was time and flexibility, not cash. Based on his work since, I imagine Tim’s answer to the $10 million question was to learn esoteric stuff and teach people at scale on how to improve their lives.

There’s a useful variant of this question: How can you spend a little money today to get the lifestyle you want?

You don’t have to postpone your target lifestyle to retirement. You can spend a little money to enjoy it today. If you dream of traveling the world, then plan smaller trips on long weekends. If you want to have a yacht, rent one for a few days. If you want to be an artist, then pay for advanced classes and work on it on the weekends.


2-minute exercise

Engage with any of these questions:

What’s your target lifestyle? What do you wish you could spend your entire day doing, for over a decade?

How much would it cost to support this lifestyle? How could you achieve that today?

How could you take the major element of your target lifestyle and have it today? Could you buy this with money?



For many of you, the answer to the $10 million question yields an answer of “I want to quit my current job and do X instead.” In many cases, there’s a way to make this work. If it’s another established career path, you might be able to act immediately – for instance, if you’re switching from being a lawyer to an entrepreneur.

In other cases, if you need more stability, then you can approach your goals incrementally. Use the Lean Startup methodology to de-risk your project as quickly as you can.

For the other question (on how to spend money to have your dream life today), you can immediately improve your life by bringing your target goals closer. Even better, you can test out if your retirement goal is really something you want to be doing for 20 years. Maybe you rent a yacht and find out it’s actually pretty boring. Now that you know, you can change your target lifestyle to something that will actually make you happy.


Question 4: What are the worst things that could happen? Could I get back here?

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 super 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. He could sell all his belongings, move into a low cost apartment, and bartend to make a small living. From a scale of 1 to 10, 1 being no impact and 10 being permanently life changing, Tim realized his worst case was a temporary impact of 3.

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.


2-minute exercise

This is a longer but super valuable exercise, so take the time you need.

First, choose something big you really want to do, but are afraid of. Now define your nightmare scenario, the absolute worst-case event that could happen.

Next, picture how you can recover from this worst case scenario.

So what would be the permanent impact of this worst case scenario, from 1 to 10? And how likely is that worst case scenario to happen?

What measures could you take to prevent the worst case scenario from happening?

Finally, what is the best case, permanent impact this could have on your life?



Chances are, the worst case scenario is nowhere near as permanent as you thought. And the best case scenario is awesome and permanently improves your life.

So it’s silly to wait, isn’t it? You’re letting your fear block you from your ideal happiness.

When I left my MDPhD program at Harvard Medical School to start a company, I went through a similar questioning process. In the very worst case, my startup would fail and I’d be embarrassed. I’d go back to the medical school dean, tail tucked between my legs, and beg to be readmitted. My medical training would be delayed by a few years, but I’d get right back on track.

But if I didn’t take this chance to start a company, something I knew I enjoyed a heck of a lot more than medicine, I would regret it forever.


Question 5: If I could only work 2 hours per week on my business, 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?

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.

This type of thinking led him to his famous 4-Hour Workweek concept.


2-minute exercise

If you were forced to work for only 2 hours a week, what could you do to capture as much value as you could?



If you’re like most people, you probably feel overworked and stressed about how long your todo list is.

This question forces you to find the highest-yield components of your time. What 20% of your activity accounts for 80% of your output?

Often, this question highlights activities of especially high leverage. If the greatest output of your time is coming up with ideas, rather than the grunt work, you should spend more time on ideation.

This question is tough in some roles, like service and manual labor – if you work on an assembly line, it’s hard to compress your time. But it doesn’t hurt to think about crazy ideas. Maybe you could hire a cheaper doppelganger to take your place, and you spend 2 hours supervising this person. This can stir a line of thinking that leads you to the idea of rising to management.


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

Tim Ferriss frames this as a management-centered question, but I’ll expand it after his story.

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.

Clearly Tim Ferriss’s situation is rooted in management, but I’ll try to extend this to a general question more people can use. Even if you’re not a manager, you probably have people who depend on you for answers, and asking for your guidance soaks up time.


2-minute exercise

Who are you currently acting as a bottleneck for? Who comes to you for lots of decisions that suck up your time?

What is the worst case scenario if you gave them more autonomy? How could you limit the damage that happens?



If you’re a micromanager, 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.

You’d be surprised how well people do when given more responsibility and trust. As Tim Ferriss says, “people’s IQs seem to double.”


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Question 7: What’s the least crowded channel?

This question prompts you to find undervalued ways to achieve your goals.

When launching his first book, The 4-Hour Workweek, Tim Ferriss asked best-selling authors, “What were the biggest wastes of time in promoting your book? What would you never do again? 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 4hourworkweek blog, which led to his first viral posts.

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?

But for non-entrepreneurs, I’ll extend the question, once again.


2-minute exercise

Who are your direct competitors who have the same goals as you? What are they all spending more of their time doing? What’s the common wisdom?

Now invert. What could you do that’s undervalued and uncrowded, that could help you reach the same goal?



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?

This question might be hard to get answers purely from introspection. Ask experienced people who have already accomplished your goals – what were the biggest wastes of time in your growth? What would you never do again? What would you do more of?


Question 8: What if I couldn’t pitch my product directly?

People don’t like announcements or being sold products. They like hearing narratives.

When promoting The 4-Hour Workweek, Tim Ferriss couldn’t get 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.

This reflects a broader psychological bias toward accepting reasons for doing things. A famous experiment showed how giving a nonsensical reason could excuse your behavior. Here’s how it worked:

A researcher would see someone waiting at the copy machine. The researcher would then ask the person one of the following questions:

Version 1: “Excuse me, I have 5 pages. May I use the Xerox machine?”
Version 2: “Excuse me, I have 5 pages. May I use the xerox machine, because I’m in a rush?”
Version 3: “Excuse me, I have 5 pages. May I use the xerox machine, because I have to make copies?”

Version 2 and 3 gave a reason, but Version 3 gave a nonsensical reason – everyone is there to make copies!

For each version, what percentage of people would you predict let the researcher cut in front? Here are the results:

Version 1: 60 percent
Version 2: 94 percent
Version 3: 93 percent

Astoundingly, the nonsensical reason worked just as well in convincing the other person.

Granted, this effect may be enriched for a small favor like this, whereas a larger deliberate decision would be subject to more scrutiny (“I have to buy an aircraft carrier because we want to patrol the seas!”). But the general point stands – people like having reasons for acting. Tim Ferriss couldn’t promote his book directly, but people did want to share unusual stories surrounding the book.


2-minute exercise

Where are you having a hard time being persuasive?

How can you craft a narrative that justifies your point of view?



Giving reasons for things makes your pitch more effective.

Want to get a raise? Don’t just ask for it. Articulate your proven value to the company and compare to market rates you could achieve elsewhere. Also, tie it to an emotional reason for the boss to care – maybe you want to work toward a down payment on your house, or you need extra savings to take care of a family member.

And if you’re afraid of following through, use the fear exercise steps above to tease out why you’re anxious.


Question 9: What if I created my own real-world MBA?

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.

Tim’s viewpoint can be applied to all graduate degrees, training programs, or even college. The actual monetary cost is often huge – MBAs can total $160k, including all expenses. Insidiously, the opportunity cost is huge, because when you’re in school, you’re not earning salary. MBAs could be giving up $200k in income during that time.


2-minute exercise

What large educational investment are you planning to make soon? What are the goals of this investment?

How much does it cost in total – including all cash, loans, and the salary you’re giving up?

Could you take all of this cost, totally spend it, and achieve your goals?



Academic degrees are the traditional, structured path of learning things. But if you’re self-driven and resourceful, you can exceed the benefits of the degree with the same cost.

For instance, if you want to get an MFA in Writing, this can cost $30k. You might also be giving up income of $50k. That $80k can go a huge way.

For instance, you could sign up for master classes with the best writer in your area, paying $500/hr for custom feedback and mentorship. You could fund group dinners with aspiring writers as a way to network – even $500 per dinner can help you make 10 valuable connections. You could hire an agent to shop your work around. This could push the value well beyond the cost of the MFA.

Granted, in some professions, the degree is basically a prerequisite. You can’t become a doctor without an MD; usually can’t become an academic professor without a PhD. But you should still articulate your goals for getting the degree. If the degree isn’t CRITICAL for what you want to do, then strongly consider building a different path. If you’re getting a PhD to go into consulting, strongly consider becoming a consultant right away and using your extra cash to build your network and gain access to science.


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Question 10: Do I need to make it back the way I lose it?

Have you lost something recently? Your natural instinct is to make it back the same way you lost it. But this ignores the value of your time and could be inefficient.

In 2008, Tim Ferriss owned a house in San Jose and lost money in the recession. Selling then would mean a $150,000 loss. His friends counseled him to rent the house until the value could rebound. Tim followed the advice and was miserable from all the property management headaches that followed.

Instead, he realized the valuable asset here was his time, not cash. By babysitting his house, he might be able to recoup the $150,000 over 5 years. But using the same time and energy, he might be able to grow his brand and business by $500,000.

Tim decided to sell the house.

We’re all subject to similar thoughts as Tim. In this case, sunk cost fallacy, loss aversion, and anchoring all make him try to recover the loss. Since his first investment in the house, Tim continued to obsess about the value of his house. All rent, mortgage, and time considerations were confined to the scope of the house problem.

But by stepping above this, Tim saw that cash and time were fungible assets that could be shuffled between projects. And his ROI for cash and time were higher in other projects than in saving this house.

If you lose $1,000 at the blackjack table, is this where you should try to recoup it? Probably not.

An interesting take on this question is to expand beyond just cash, as you’ll see next.


2-minute exercise

Where have you had a recent loss? This can be in terms of cash, emotion, social standing, or however you interpret it.

How can you regain the value of that loss through a totally different means?



When you’re stressed about a loss, you tend to obsess about it over and over, thinking about how to regain what you lost. But you have to poke your head above the weeds and find other routes.

Do you feel like you’ve lost ground in an argument? Maybe you don’t have to regain footing in that very argument. Cut your losses, admit your fault, and think about how to do better next time.

Have you lost the favor of your boss? Maybe you don’t regain it by repeating what got you there in the first place. Use your strengths and carve out another path to demonstrate your value. Hell, maybe even regaining stature in the current company isn’t the right approach, and it’s now time to join a new company.

Lost a romantic partner for good? Stop thinking about how to win that person back. Spend your energy on bettering yourself to attract other partners.

In business, some projects work, and some don’t. Don’t throw good money after bad, and try to see how you can eke out another 5% from a project. You’re probably missing a 500% gain elsewhere.


Question 11: What if I could only subtract to solve problems?

Removing things is often easier than adding things. What can you simplify to achieve growth?

This is counterintuitive, because it seems like more motion in more areas should lead to more progress. But your different activities have different ROI. And you should focus your energy on those.

Tim already showed subtraction when running BrainQUICKEN – how could he reduce his customer support time? How could he reduce the number of decisions he had to make? This prompted automation of order fulfillment and giving his employees more autonomy.

This applies to small tactical items too, like your product design or website. Removing the number of distracting items can improve conversion rate.


2-minute exercise

Picture an area of your life with a lot of complexity and motion. What should you cut out that’s not valuable? What should you put on your not-to-do list?

Now some items remain. Would doubling your effort on these remaining items lead to greater value?



With countless distractions and frivolities available to you, focus is hard. To appear like a team player, you take on more responsibilities than you should handle. Because of FOMO (fear of missing out), you drag yourself to more social events than you actually enjoy.

Focusing is a common thread in Tools of Titans. Look here for my favorite excerpts on this subject [tk https://allencheng.wpengine.com/tools-of-titans-summary-tim-ferriss/#You_Need_to_Focus]

Some of my favorites:
– If it’s not a “hell, yes!” it’s a “no.” Only accept things you’re really excited about, because life is short.
– “Being busy is a form of laziness – lazy thinking and indiscriminate action. Being busy is most often used as a guise for avoiding the few critically important but uncomfortable actions.” – Tim Ferriss


Question 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?

If you’re feeling burned out, some time away will help you regain clarity. Making sure your business or work runs smoothly while you’re gone will reveal optimizations you can implement today. This question is useful even if you don’t plan on taking any time off.

Tim Ferriss poses the question with two specific wordings:

  • you specifically have to go “off the grid” – it’s not just a vacation. During this time, you cannot check your email.
  • you also are away for 4 to 8 weeks. Taking off 2 weeks is too short – people will just let small issues pile up, knowing you’re back in 2 weeks. When they know you’re gone for 8 weeks, they have to solve the issues themselves.

Answering this question will reveal the ways in which you’re being a firefighter and not spending your time on the big picture. If you’re going away for 8 weeks, you have to entrust people with authority, clarify their goals, implement automated systems that streamline processes, and more.

This will allow operation of your business or work without your continuous presence, which in turn will reduce stress and help you focus on the big picture.


2-minute exercise

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

Could I implement those practices now, without actually going away?



When considering this question, most likely you’re picturing the little stressful fires that somehow come to you to deal with. If you’re gone for 8 weeks, then no one has any idea how to handle them, and your business or work will collapse. This means a lot of decisions in the company bottleneck on you.

This is where Tim’s Question #6 helps – “What if I let them make decisions up to $100? $500? $1,000?” You’d be surprised how well people handle responsibilities they don’t seem absolutely ready for yet. If you’ve hired the right people, they will often rise to the task. I know this is scary. Experiment with incremental steps to build your confidence.

Another common fear with going totally off the grid is that your colleagues will fly off the rails without your masterful guidance. This probably means you’re a micromanager. If your team will work on wasteful projects without your presence, then their long-term goals aren’t clear to them. You probably don’t have clear ways to measure their progress – otherwise they could use those metrics to guide their own work.

If this is true, you’ll find the concepts in High Output Management useful. This will train you to be a more hands-off manager while encouraging even more productivity.

You can implement your ideas from this question without even going on vacation. The result – a more stress-free, non-firefighting role that lets you focus on big important questions.


Question 13: Am I hunting antelope or field mice?

Do you spend your days tackling the most important items, or minor details?

The analogy comes from James Carville’s book:

“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.”

“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?”

Don’t chase all the small details. If you get the big picture items right, everything else will fall into place.

One of my favorite metaphors from Tools of Titans comes from Kaskade. Imagine you have a glass jar, and next to it big rocks, pebbles, and sand. If you put the sand and pebbles in first, they take up the space, and you can’t fit the big rocks in. But if you add the big rocks, then the pebbles, then the sand, everything fits.


2-minute exercise

Picture your to-do list. Which single item, if done, would make the rest easier or irrelevant?



Many of us are addicted to the feeling of being busy. Having lots of obligations makes us feel needed by society. Importantly, it also signals to your friends that you’re so busy and important.

Another favorite quote from Tools of Titans from Tim Kreider: People are “addicted to busyness and dread what they might have to face in its absence.” Being busy is an “existential reassurance, a hedge against emptiness: Obviously your life cannot possibly be silly or trivial or meaningless if you are so busy, completely booked, in demand every hour of the day.”

In the absence of busyness, people have to confront the idea that their motion and existence may not actually matter.

This doesn’t have to plunge into nihilism. Your life probably does mean a lot of value, however you define it. But likely many of the items you’re busy with aren’t actually contributing to your main goals.

If you could use help on goal setting and figuring out your most important items, check out the Goal Hierarchy concept from Grit.

You spend 5 minutes figuring out where you want to eat for dinner for 1.5 hours. If you spent that 5% of time on your career, this would be 2 full working years, just spent on figuring out how to live your life.


Question 14: Could it be that everything is fine and complete as is?

You may be hard-wired to seek achievement, to being perpetually happy being unhappy.

What if you can be happy with what you currently have?

Tim Ferriss found that expressing gratitude for his past and present has made him substantially happier. In his daily morning journal, he thanks 3 things that make him happy – like a good cup of tea or a friend he saw a year ago.

Take a few minutes to do the same.


2-minute exercise

Name 3 things you’re grateful for. Instead of generic items like your health, consider:

  • An old relationship that really helped you
  • An opportunity you have today
  • Something great that happened yesterday that happened to you or that you saw
  • Something simple near you or within sight



Do you feel any happier?

If you’re like me, you tend to be perpetually unhappy with yourself. There’s always something you can improve, and there’s always a goal just out of grasp. This future focus blocks out much else that’s great in your life.

If you continue expressing gratitude, you can ground yourself in all the things that already make your life great.

Some tactics here include:

  • at the end of each day before bed, thinking of “daily wins”
  • keeping a Jar of Awesome. When something cool happens, write it down on a slip of paper and throw it in. When you need an emotional boost, read through your old entries

Read more about gratitude tactics from Tools of Titans.


Question 15: What would this look like if it were easy?

People tend to overcomplicate routes to success. Again, the feeling of struggle and being perpetually stressed makes what you’re working on seem so important.

What if it didn’t have to be this way? What if there was a way to apply your skills to a much bigger problem, where growth was easier to find?

Reid Hoffman suggests “part of business strategy is to solve the simplest, easiest, and most valuable problem.”

In Tools of Titans, Seth Godin tells a story of designer Lynn Gordon, who had trouble getting business for her toy designs. Seth told Lynn that toy companies didn’t work that way – they didn’t accept pitches from outsiders. He counseled her to switch to the book business, where publishers were hungry for new ideas. She quickly got a hit with her 52 Activity card deck series.

Don’t overcomplicate things or feel like you need to struggle. Like above, simplify for the greatest efficiency. Look for a way to roll a rock downhill.


2-minute exercise

What would this look like if it were easy?

Where could you apply your skills to a much bigger, easier market?

Instead of improving things by 5%, where can you get a 5x improvement?



I interpret this question as trying to strip away all the added layers of complexity to find the true north.

In business, the most important thing is to create something people want. All the other little layers – social media promotion, office perks, accounting – make far less of a dent than creating something people want.

If you’re currently employed but strained by your current environment, where could you take your skills where they’re much more appreciated and rewarded? For instance, if you’re a lawyer and ground down by big law, what if you go in-house to a company like Google?

It’d be interesting to apply this to incredibly complicated fields like healthcare or politics. What would healthcare redesign look like if it were easy?


Question 16: How can I throw money at this problem? How can I waste money to improve the quality of my life?

The motivation here: the one limited resource affecting every person on Earth is time. If you can buy more time with money, this is often well worth it.

Tim Ferriss suggests, “in the beginning of your career, you spend time to earn money. Once you hit your stride, you should spend money to earn time.”


2-minute exercise

Imagine a stranger comes up to you and says, “I want to buy an hour of your time. How much will that cost?”

This is your non-work hourly rate.

Think about where you’re spending time every day. Where could you spend this money to buy back time at this hourly rate?

For example, let’s say your rate is $20/hr. In an effort to gain $100 on credit card rewards, you do 20 hours of research over a year. Clearly this isn’t worthwhile for you.



This is an underappreciated problem, because many people are prone to being penny-wise and pound foolish, especially if you didn’t grow up with much money. I think about this a lot.

Here are common examples that come to mind.

  • Transit: taking public transit and walking might cost you $3 and take an hour. Taking UberPool would cost $5 and take 20 minutes.
  • Cleaning: if you don’t enjoy cleaning and laundry, consider finding a housekeeper. In a city, you can buy $100 of cleaning that will save you 5 hours a month, and you end up with a cleaner house.
  • Cooking: cooking periodically can be a huge drain on time – a meal that would otherwise cost $20 might take 3 hours to prepare. If you don’t enjoy cooking, consider other ways of getting nourishment. I often recommend Soylent to those who don’t care about taste. If you want to be healthy, find a healthy restaurant and order a large amount of takeout to eat down over a week.
  • Discounts: going out of your way to get small discounts may not be worth your time. If you’re spending 2 hours researching flights over a few weeks to save $40, it may fall under your hourly rate.
  • Games: many games use in-game currencies (like gems or coins) to drive more playing. You can often buy these points or earn them through play. If you’re hooked primarily by this mechanic, consider how low the rate may be – possibly lower than $1 per hour of play. Once you buy some in-game currency, you may realize how manipulative the game is, and stop playing altogether.
  • Exercise: if you want to see more results in your training, hiring a personal trainer to set good habits in you might save you time in the long run. For instance, spending $200 for 4 hours of personal training time may help you save 50 hours of frustrated work in the future.

In doing all this, you might spend $200-300 per month to buy back dozens of hours of time. And these are just small everyday examples. If your hourly rate is high enough, you start opening avenues like hiring an accountant or a personal assistant.

You can then use this time to create make yourself happier. This can be time spent on hobbies or pure relaxation. Or you can use the time in higher-leverage ways, like reading books to make you more personally effective.

As an employee, consider that learning skills during your free time for 10 hours a week. This might ultimately lead to additional raises of $20k over 5 years, increasing your lifetime value by hundreds of thousands of dollars. A much better deal than saving $3 on commuting each day.

Another favorite quote from Tools of Titans: “If you’ve got enough money to solve the problem, you don’t have the problem.”


Question 17: No hurry, no pause.

In Tools of Titans, Derek Sivers gives the story of a 25-mile bike ride near his house. He’d push as hard as he could, sweating and huffing, and it’d take 43 minutes.

This was stressful, so he decided to take it easy one day. He’ll go at less than his normal pace and enjoy the ride, admiring the blue sky and the birds. When he finished the ride, he found the ride took 45 minutes.

So he endured extreme stress for just an extra 2 minutes.

The point being: You don’t need to go through life huffing and puffing. You’ll get nearly all the way there by putting one foot in front of the other, continuously. Thus “no hurry, no pause.”


2-minute exercise

Where in your life do you feel constantly at 100% of capacity? What would happen if you reduced it to 90% capacity?



When you’re constantly stressed, you risk burnout and lower productivity. Having to take breaks then lowers your overall output. A train can travel faster than a car, but the train has to take stops at multiple stations while the car can keep coasting at a lower speed.

I think about this often when driving. Going 80 mph on the highway, vs 60 mph, causes much more stress. You have to weave between lanes and you increase your risk of accidents. And on a 20 mile trip, going 80 mph saves you a measly 5 minutes.

“Slow is smooth. Smooth is fast.”


Tim Ferriss’s 17 Questions to Solve Your Life Problems

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